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New roof fall 2026! Exceptional custom-built estate offering unparalleled security, efficiency and peace of mind on two expansive lots in the heart of Winter Park. This split-plan three-bedroom and 2.5-bath home has over 4,880 total square feet in the main home and 1,944 total square feet in the detached in-law/office unit under roof. Constructed with solid poured concrete block and 1-inch insulation, this remarkable residence was designed to withstand the test of time while delivering modern luxury and comfort. A rare feature, the home includes two reinforced safe rooms built with rebar-reinforced solid poured concrete walls and 12-inch concrete ceilings, along with a built-in, concrete-bolted safe. Additional security enhancements include a full alarm system and security spotlights. Designed for everyday living and entertaining, the property is equipped with a full-house 22-kilowatt generator, a buried 500-gallon propane tank, propane gas range and outdoor grill, two tankless water heaters, whole-house water softening and filtration systems, EV charging capability and energy-efficient construction resulting in remarkably low utility costs. The well-appointed kitchen features a solid wood cabinetry, quartz countertops, a kitchen, butler pantry, coffee bar and laundry room, Verona gas range, Frigidaire Professional French-door refrigerator, KitchenAid dishwasher, convenient under-counter outlets and the kitchen island has lighted shelves. Additional highlights include plantation shutters throughout, wine cellar, climate-controlled storage attic, granite in baths, custom garage cabinetry, epoxy-finished garage floors, hurricane-impact windows in the office/apartment, Pet Turf in the entire backyard with no maintenance necessary and a striking 35-foot flagpole. Combining superior craftsmanship, advanced infrastructure and thoughtful upgrades rarely found in today's market, this extraordinary property presents a unique opportunity to own a one-of-a-kind residence. Total heated square footage includes heated/cooled space to use as garage, workshop, and/or utility room in the detached structure.

4 Beds ⋅ 4 Baths ⋅ Temple Terrace Annex SubDv. ⋅ 32792 Zip Code

New roof fall 2026! Exceptional custom-built estate offering unparalleled security, efficiency and peace of mind on two expansive lots in the heart of Winter Park. This split-plan three-bedroom and 2.5-bath home has over 4,880 total square feet in the main home and 1,944 total square feet in the detached in-law/office unit under roof. Constructed with solid poured concrete block and 1-inch insulation, this remarkable residence was designed to withstand the test of time while delivering modern luxury and comfort. A rare feature, the home includes two reinforced safe rooms built with rebar-reinforced solid poured concrete walls and 12-inch concrete ceilings, along with a built-in, concrete-bolted safe. Additional security enhancements include a full alarm system and security spotlights. Designed for everyday living and entertaining, the property is equipped with a full-house 22-kilowatt generator, a buried 500-gallon propane tank, propane gas range and outdoor grill, two tankless water heaters, whole-house water softening and filtration systems, EV charging capability and energy-efficient construction resulting in remarkably low utility costs. The well-appointed kitchen features a solid wood cabinetry, quartz countertops, a kitchen, butler pantry, coffee bar and laundry room, Verona gas range, Frigidaire Professional French-door refrigerator, KitchenAid dishwasher, convenient under-counter outlets and the kitchen island has lighted shelves. Additional highlights include plantation shutters throughout, wine cellar, climate-controlled storage attic, granite in baths, custom garage cabinetry, epoxy-finished garage floors, hurricane-impact windows in the office/apartment, Pet Turf in the entire backyard with no maintenance necessary and a striking 35-foot flagpole. Combining superior craftsmanship, advanced infrastructure and thoughtful upgrades rarely found in today's market, this extraordinary property presents a unique opportunity to own a one-of-a-kind residence. Total heated square footage includes heated/cooled space to use as garage, workshop, and/or utility room in the detached structure.

1940 Magnolia Avenue, Winter Park

$1,175,000

English cottage–inspired architecture, enchanting gardens and a setting directly across from Lake Sylvan introduce this exquisitely renovated Winter Park residence. Set among distinguished residences and substantial lakefront estates, the home occupies a corner lot along a charming brick street and offers three bedrooms, three full bathrooms and approximately 2,096 square feet of living space. Extensive improvements in recent years bring together exceptional finishes, thoughtful craftsmanship and substantial updates behind the walls. With interior design by New York City–based Paulette Pascarella, traditional architectural details find fresh expression through sophisticated materials and beautifully considered modern appointments. Expansive windows welcome natural light, while polished marble flooring in warm ivory tones extends throughout much of both levels. The kitchen features solid wood cabinetry, quartz countertops and a full-height backsplash, complemented by a Bertazzoni refrigerator, Bosch 800 Series gas range and Miele dishwasher. A separate study and sitting room has wood flooring and custom built-ins. With a full bathroom immediately adjacent, this versatile space presents potential for conversion into a fourth bedroom with an en-suite bath. Carefully selected details include Visual Comfort and Currey lighting, Buster + Punch and Baldwin hardware, and custom window treatments incorporating designer textiles and motorized shades from The Shade Store. Nine Marvin Ultimate windows with wood interiors, a VELUX skylight and a mahogany Craftsman front door further distinguish the renovation. A custom stair railing by Boris Petkoff Iron Works and millwork by Dunning Custom Carpentry add distinctive craftsmanship. All three bedrooms are upstairs, where the primary suite features soaring ceilings, treetop outlooks and an extensively fitted California Closets walk-in dressing room with custom cabinetry and soft-close dovetail drawers. Its beautifully appointed bathroom features Perrin + Rowe Georgian Era vanity and shower fixtures, reflecting the caliber of fittings selected throughout the home. Two additional bedrooms, one with an en-suite bathroom, provide flexibility for guests or a home office. Upstairs views of Lake Sylvan connect the interiors to their picturesque surroundings. Substantial improvements include whole-house repiping, electrical upgrades, a Rinnai tankless water heater and a whole-house water treatment system. The roof was replaced in August 2023. Outside, cottage gardens frame a welcoming entrance, while an intimate brick patio nestled within the garden and a quiet garden corner offer peaceful places for morning coffee or an afternoon outdoors. A private parking pad adds convenience. Beyond the garden, oak-shaded brick streets invite leisurely walks past beautiful homes and scenic views of Lakes Sylvan and Osceola. A small lakeside green space lies just down Harris Circle, with Crosby Wellness Center, AdventHealth and Park Avenue’s dining, boutiques and cultural attractions conveniently nearby. An inviting choice for a primary residence or Winter Park retreat.

3 Beds ⋅ 3 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

English cottage–inspired architecture, enchanting gardens and a setting directly across from Lake Sylvan introduce this exquisitely renovated Winter Park residence. Set among distinguished residences and substantial lakefront estates, the home occupies a corner lot along a charming brick street and offers three bedrooms, three full bathrooms and approximately 2,096 square feet of living space. Extensive improvements in recent years bring together exceptional finishes, thoughtful craftsmanship and substantial updates behind the walls. With interior design by New York City–based Paulette Pascarella, traditional architectural details find fresh expression through sophisticated materials and beautifully considered modern appointments. Expansive windows welcome natural light, while polished marble flooring in warm ivory tones extends throughout much of both levels. The kitchen features solid wood cabinetry, quartz countertops and a full-height backsplash, complemented by a Bertazzoni refrigerator, Bosch 800 Series gas range and Miele dishwasher. A separate study and sitting room has wood flooring and custom built-ins. With a full bathroom immediately adjacent, this versatile space presents potential for conversion into a fourth bedroom with an en-suite bath. Carefully selected details include Visual Comfort and Currey lighting, Buster + Punch and Baldwin hardware, and custom window treatments incorporating designer textiles and motorized shades from The Shade Store. Nine Marvin Ultimate windows with wood interiors, a VELUX skylight and a mahogany Craftsman front door further distinguish the renovation. A custom stair railing by Boris Petkoff Iron Works and millwork by Dunning Custom Carpentry add distinctive craftsmanship. All three bedrooms are upstairs, where the primary suite features soaring ceilings, treetop outlooks and an extensively fitted California Closets walk-in dressing room with custom cabinetry and soft-close dovetail drawers. Its beautifully appointed bathroom features Perrin + Rowe Georgian Era vanity and shower fixtures, reflecting the caliber of fittings selected throughout the home. Two additional bedrooms, one with an en-suite bathroom, provide flexibility for guests or a home office. Upstairs views of Lake Sylvan connect the interiors to their picturesque surroundings. Substantial improvements include whole-house repiping, electrical upgrades, a Rinnai tankless water heater and a whole-house water treatment system. The roof was replaced in August 2023. Outside, cottage gardens frame a welcoming entrance, while an intimate brick patio nestled within the garden and a quiet garden corner offer peaceful places for morning coffee or an afternoon outdoors. A private parking pad adds convenience. Beyond the garden, oak-shaded brick streets invite leisurely walks past beautiful homes and scenic views of Lakes Sylvan and Osceola. A small lakeside green space lies just down Harris Circle, with Crosby Wellness Center, AdventHealth and Park Avenue’s dining, boutiques and cultural attractions conveniently nearby. An inviting choice for a primary residence or Winter Park retreat.

1500 Harris Circle, Winter Park

$1,175,000

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 230 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable homesite with private lake access and the ability to build your own dock.

3 Beds ⋅ 3 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 230 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable homesite with private lake access and the ability to build your own dock.

240 Killarney Drive, Winter Park

$1,150,000

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 240 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable corner homesite with private lake access and the ability to build your own dock.

4 Beds ⋅ 1 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 240 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable corner homesite with private lake access and the ability to build your own dock.

230 Killarney Drive, Winter Park

$1,095,000

WELCOME TO CONTEMPORARY LUXURY IN THE HEART OF WINTER PARK! This stunning two-story pool residence has been beautifully remodeled from top to bottom and offers high end design, high-end finishes and an exceptional lifestyle location near East End Market, Baldwin Park, Audubon Park and all of Winter Parks charm. Behind the private gated courtyard and modern fencing, discover a thoughtfully designed home featuring custom built-ins, designer finishes, porcelain tile, custom wood-plank stairs and a dramatic modern glass railing. The beautifully appointed kitchen is designed for both entertaining and everyday living and features premium Wolf gas cooking appliances with range hood, Sub-Zero refrigerator, stainless steel wine refrigerator, microwave, stainless farmhouse sink, pantry and stylish pendant lighting. The open living areas provide a wonderful setting for gathering and entertaining. The downstairs primary suite offers convenience, privacy and direct access to the spectacular outdoor pool living area. The luxurious en-suite bath features dual vanities, custom cabinetry and mirrors, high-end designer fixtures, beautiful tile work and a spacious glass-enclosed shower. Upstairs, you will find generously sized bedrooms, custom closet spaces and a beautifully finished bonus room offers exceptional flexibility for a home office, fitness room, exercise space, storage or additional flex space. Additional features include a dedicated first floor laundry room and powder room, upstairs linen closet, designer lighting through out and a two-car garage. Step outside to your own private retreat! The covered lanai flows seamlessly to the beautiful custom pool and outdoor entertaining area featuring a gas fire pit. Mature bamboo landscaping, a fenced yard and contemporary entrance fencing create a private and inviting setting. LOCATION, LOCATION, LOCATION! Enjoy the highly desirable Winter Park lifestyle with convenient access to East End Market, local coffee shops, exceptional restaurants, specialty shopping, markets and community events. Nearby destinations include Leu Gardens, Baldwin Park, Park Avenue and Downtown Winter Park. Zoned for Audubon Park School (K-8) and Winter Park High School; buyers should verify school assignments and enrollment eligibility. This exceptional move-in-ready home combines contemporary luxury, resort-style outdoor living and one of Central Florida’s most desirable lifestyle locations!

3 Beds ⋅ 3 Baths ⋅ Edgewood Sub SubDv. ⋅ 32789 Zip Code

WELCOME TO CONTEMPORARY LUXURY IN THE HEART OF WINTER PARK! This stunning two-story pool residence has been beautifully remodeled from top to bottom and offers high end design, high-end finishes and an exceptional lifestyle location near East End Market, Baldwin Park, Audubon Park and all of Winter Parks charm. Behind the private gated courtyard and modern fencing, discover a thoughtfully designed home featuring custom built-ins, designer finishes, porcelain tile, custom wood-plank stairs and a dramatic modern glass railing. The beautifully appointed kitchen is designed for both entertaining and everyday living and features premium Wolf gas cooking appliances with range hood, Sub-Zero refrigerator, stainless steel wine refrigerator, microwave, stainless farmhouse sink, pantry and stylish pendant lighting. The open living areas provide a wonderful setting for gathering and entertaining. The downstairs primary suite offers convenience, privacy and direct access to the spectacular outdoor pool living area. The luxurious en-suite bath features dual vanities, custom cabinetry and mirrors, high-end designer fixtures, beautiful tile work and a spacious glass-enclosed shower. Upstairs, you will find generously sized bedrooms, custom closet spaces and a beautifully finished bonus room offers exceptional flexibility for a home office, fitness room, exercise space, storage or additional flex space. Additional features include a dedicated first floor laundry room and powder room, upstairs linen closet, designer lighting through out and a two-car garage. Step outside to your own private retreat! The covered lanai flows seamlessly to the beautiful custom pool and outdoor entertaining area featuring a gas fire pit. Mature bamboo landscaping, a fenced yard and contemporary entrance fencing create a private and inviting setting. LOCATION, LOCATION, LOCATION! Enjoy the highly desirable Winter Park lifestyle with convenient access to East End Market, local coffee shops, exceptional restaurants, specialty shopping, markets and community events. Nearby destinations include Leu Gardens, Baldwin Park, Park Avenue and Downtown Winter Park. Zoned for Audubon Park School (K-8) and Winter Park High School; buyers should verify school assignments and enrollment eligibility. This exceptional move-in-ready home combines contemporary luxury, resort-style outdoor living and one of Central Florida’s most desirable lifestyle locations!

1922 Hammerlin Avenue, Winter Park

$1,050,000

Beautifully maintained Winter Park pool home with a 2026 whole-home repipe, 2019 roof, and 2022 A/C in the desirable Waterbridge neighborhood. Discover the charm of established Winter Park living in this inviting single-story home, situated on a beautifully landscaped 0.36-acre lot in the sought-after 32789 ZIP code. Spacious living areas, abundant natural light, and two inviting fireplaces, including a fireplace in the living room and a distinctive stone fireplace in the primary suite, create a warm and welcoming atmosphere. Step outside to your private swimming pool, surrounded by mature landscaping, offering the perfect setting for relaxing or entertaining. Additional features include a tankless water heater, updated pool equipment, and access to Waterbridge neighborhood tennis courts. An exceptional Winter Park location. Enjoy convenient proximity to AdventHealth Winter Park Hospital, the Winter Park VA Clinic, and Winter Park High School, along with easy access to downtown Winter Park's iconic Park Avenue, renowned restaurants, boutique shopping, Rollins College, Mead Botanical Garden, and downtown Orlando. Combining valuable improvements, single-story convenience, private pool living, and an established neighborhood setting, 1735 Demetree Drive offers the character, comfort, and lifestyle that make Winter Park, Florida, such a desirable place to call home.

4 Beds ⋅ 3 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code

Beautifully maintained Winter Park pool home with a 2026 whole-home repipe, 2019 roof, and 2022 A/C in the desirable Waterbridge neighborhood. Discover the charm of established Winter Park living in this inviting single-story home, situated on a beautifully landscaped 0.36-acre lot in the sought-after 32789 ZIP code. Spacious living areas, abundant natural light, and two inviting fireplaces, including a fireplace in the living room and a distinctive stone fireplace in the primary suite, create a warm and welcoming atmosphere. Step outside to your private swimming pool, surrounded by mature landscaping, offering the perfect setting for relaxing or entertaining. Additional features include a tankless water heater, updated pool equipment, and access to Waterbridge neighborhood tennis courts. An exceptional Winter Park location. Enjoy convenient proximity to AdventHealth Winter Park Hospital, the Winter Park VA Clinic, and Winter Park High School, along with easy access to downtown Winter Park's iconic Park Avenue, renowned restaurants, boutique shopping, Rollins College, Mead Botanical Garden, and downtown Orlando. Combining valuable improvements, single-story convenience, private pool living, and an established neighborhood setting, 1735 Demetree Drive offers the character, comfort, and lifestyle that make Winter Park, Florida, such a desirable place to call home.

1735 Demetree Drive, Winter Park

$1,049,900

Located in an intimate gated community of just 28 homes and minutes from Downtown Winter Park, this exceptional former K. Hovnanian model home features over $200,000 in builder and custom upgrades. Ideally located just 2 miles from Target and Costco, near the 417, and next to highly regarded private schools including Trinity Preparatory School, this home offers luxury and convenience in an unbeatable location. The stunning Michelson floorplan features an open-concept design with beautiful wood-look tile flooring, a private office, formal dining room, built-in speakers, and designer finishes throughout. The gourmet kitchen showcases quartz countertops, 42” cabinetry, stainless steel appliances, gas cooktop, oversized island, butler’s pantry with wine fridge, and a custom walk-in pantry. Massive 12-foot triple sliding doors open to a resort-style backyard with a pool, custom fire pit, pergola seating, and pre-wire for a gas grill. The first floor includes a private guest suite with pool access, full bath, mudroom, half bath, and oversized three-car tandem garage with overhead storage. Upstairs features an expansive loft and bonus room, spacious bedrooms with walk-in closets, Jack-and-Jill bath, additional full bath, large laundry room, and a luxurious owner’s retreat with tray ceilings, coffee bar, spa-inspired bath, oversized shower, and enormous walk-in closet. Residents also enjoy a private community dock for kayaking, paddleboarding, or sunset views. Additional highlights include a brand-new A/C and countless high-end finishes. TAX SAVINGS! Buyers who qualify for Florida Homestead may also benefit from a proposed 2026 constitutional amendment that could increase the homestead exemption to $150,000 in 2027 and $250,000 in 2028 on non-school property taxes if approved by voters. Buyers should verify eligibility and potential savings with the Seminole County Property Appraiser. A rare combination of luxury, location, privacy, and potential tax benefits—this meticulously maintained home is a must-see!

5 Beds ⋅ 5 Baths ⋅ Lake Florence Preserve SubDv. ⋅ 32792 Zip Code

Located in an intimate gated community of just 28 homes and minutes from Downtown Winter Park, this exceptional former K. Hovnanian model home features over $200,000 in builder and custom upgrades. Ideally located just 2 miles from Target and Costco, near the 417, and next to highly regarded private schools including Trinity Preparatory School, this home offers luxury and convenience in an unbeatable location. The stunning Michelson floorplan features an open-concept design with beautiful wood-look tile flooring, a private office, formal dining room, built-in speakers, and designer finishes throughout. The gourmet kitchen showcases quartz countertops, 42” cabinetry, stainless steel appliances, gas cooktop, oversized island, butler’s pantry with wine fridge, and a custom walk-in pantry. Massive 12-foot triple sliding doors open to a resort-style backyard with a pool, custom fire pit, pergola seating, and pre-wire for a gas grill. The first floor includes a private guest suite with pool access, full bath, mudroom, half bath, and oversized three-car tandem garage with overhead storage. Upstairs features an expansive loft and bonus room, spacious bedrooms with walk-in closets, Jack-and-Jill bath, additional full bath, large laundry room, and a luxurious owner’s retreat with tray ceilings, coffee bar, spa-inspired bath, oversized shower, and enormous walk-in closet. Residents also enjoy a private community dock for kayaking, paddleboarding, or sunset views. Additional highlights include a brand-new A/C and countless high-end finishes. TAX SAVINGS! Buyers who qualify for Florida Homestead may also benefit from a proposed 2026 constitutional amendment that could increase the homestead exemption to $150,000 in 2027 and $250,000 in 2028 on non-school property taxes if approved by voters. Buyers should verify eligibility and potential savings with the Seminole County Property Appraiser. A rare combination of luxury, location, privacy, and potential tax benefits—this meticulously maintained home is a must-see!

1448 Lake Florence Way, Winter Park

$1,049,000

Some houses impress you. This one welcomes you. A fully remodeled Victorian in Winter Park, reimagined from top to bottom and minutes from Park Avenue shopping and dining. The kitchen is the heart of it all, wrapped in Calacatta Viola quartz with a full height backsplash, cabinet lighting that glows after dark, and all new Bosch appliances. The open first floor flows naturally from kitchen to dining to living, anchored by a fireplace made for slow evenings, and new engineered hardwood flooring runs throughout the entire house. All 3.5 baths are completely redone with marble floors, designer tile, and brass fixtures, including a first floor half bath with wall paneling and a one of a kind vanity that stops people mid tour. This remodel went beyond the pretty parts. A brand new roof covers the entire house and detached garage, all outlets and switches were replaced throughout, and the plumbing was redone for the kitchen and all bathrooms. The water heater is new, and the laundry room has a new stacked washer and dryer too. You move in and live, nothing to fix, nothing to update. Upstairs and down, every bedroom is spacious and has custom built in closet systems, and the stairway shows off custom oak newels and handrails with black metal balusters. Outside, the charm continues with a herringbone brick-tile front porch, balconies and back porch made for morning coffee, fresh paint inside and out, new landscaping, a new paver driveway, and a detached two car garage with a newly stained concrete floor. This is not a quick flip. Every finish was chosen with intention, and every detail was completed with care. 4 bedrooms, 3.5 baths, 2,135 sq ft of living space on a 7,151 sq ft lot, in one of Winter Park's most loved pockets. This is a home you will feel from the first moment you walk in.

4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

Some houses impress you. This one welcomes you. A fully remodeled Victorian in Winter Park, reimagined from top to bottom and minutes from Park Avenue shopping and dining. The kitchen is the heart of it all, wrapped in Calacatta Viola quartz with a full height backsplash, cabinet lighting that glows after dark, and all new Bosch appliances. The open first floor flows naturally from kitchen to dining to living, anchored by a fireplace made for slow evenings, and new engineered hardwood flooring runs throughout the entire house. All 3.5 baths are completely redone with marble floors, designer tile, and brass fixtures, including a first floor half bath with wall paneling and a one of a kind vanity that stops people mid tour. This remodel went beyond the pretty parts. A brand new roof covers the entire house and detached garage, all outlets and switches were replaced throughout, and the plumbing was redone for the kitchen and all bathrooms. The water heater is new, and the laundry room has a new stacked washer and dryer too. You move in and live, nothing to fix, nothing to update. Upstairs and down, every bedroom is spacious and has custom built in closet systems, and the stairway shows off custom oak newels and handrails with black metal balusters. Outside, the charm continues with a herringbone brick-tile front porch, balconies and back porch made for morning coffee, fresh paint inside and out, new landscaping, a new paver driveway, and a detached two car garage with a newly stained concrete floor. This is not a quick flip. Every finish was chosen with intention, and every detail was completed with care. 4 bedrooms, 3.5 baths, 2,135 sq ft of living space on a 7,151 sq ft lot, in one of Winter Park's most loved pockets. This is a home you will feel from the first moment you walk in.

1517 Harmon Avenue, Winter Park

$999,000

A truly special property in Winter Park’s 32789 zip code, this renovated 1925 Craftsman is filled with character and charm. Set on an oversized 0.36-acre lot just one home from Lake Killarney, the property is 2803sf, with a 3/2 main residence (approximately 2200sf) plus a detached 1/1 guest cottage (approximately 600sf). Beautiful curb appeal and a glass-enclosed front porch with beadboard ceiling welcome you into the home. The original piano, which has been in the house since it was built, adds to its rich history and charm. Great layout for entertaining, with multiple sitting areas and an open floor plan with a dining room that flows to the family room and kitchen, all flooded with natural light and numerous windows and French doors. The kitchen offers bar seating, granite countertops, custom cabinetry and storage, stainless steel appliances, a natural-gas cooktop, glass tile backsplash, and tall ceilings. Glass French doors open to a brick patio and a walkway leading to the guest cottage. The two back bedrooms share a Jack-and-Jill bathroom, and the front bedroom with an adjacent hall bath connects to the enclosed sunroom, perfect for a nursery, office, or den. Additional details include original oak floors, crown molding, glass doorknobs, designer lighting, interior laundry with a new washer and dryer, and an upgraded security system. The expansive backyard features mature landscaping and ample space for outdoor enjoyment, with potential for a future pool. The metal-roofed carport includes a ceiling fan and string lights, and Lake Killarney is visible from several areas of the property. The guest cottage includes one bedroom, one bathroom, a living room, and a full kitchen—ideal for guests, extended family, a home office, or as a potential income-producing property. Recent improvements include the main-house roof in 2020; guest-cottage roof in 2022; two new guest-cottage A/C units installed in March 2023; security system in 2023; PVC water line and irrigation pump in 2024; main-house washer and dryer in June 2026; and exterior paint in August 2026. Additional updates include kitchen appliances, lighting and hardware, landscaping and irrigation system with well, interior paint, and a transferable termite bond. Conveniently located within easy walking distance of Hillstone, Trader Joe’s, numerous shops and restaurants, and quick access to I-4. All room dimensions, home & guest cottage square footage, and land square footage are approximate. Buyer to verify.

4 Beds ⋅ 3 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

A truly special property in Winter Park’s 32789 zip code, this renovated 1925 Craftsman is filled with character and charm. Set on an oversized 0.36-acre lot just one home from Lake Killarney, the property is 2803sf, with a 3/2 main residence (approximately 2200sf) plus a detached 1/1 guest cottage (approximately 600sf). Beautiful curb appeal and a glass-enclosed front porch with beadboard ceiling welcome you into the home. The original piano, which has been in the house since it was built, adds to its rich history and charm. Great layout for entertaining, with multiple sitting areas and an open floor plan with a dining room that flows to the family room and kitchen, all flooded with natural light and numerous windows and French doors. The kitchen offers bar seating, granite countertops, custom cabinetry and storage, stainless steel appliances, a natural-gas cooktop, glass tile backsplash, and tall ceilings. Glass French doors open to a brick patio and a walkway leading to the guest cottage. The two back bedrooms share a Jack-and-Jill bathroom, and the front bedroom with an adjacent hall bath connects to the enclosed sunroom, perfect for a nursery, office, or den. Additional details include original oak floors, crown molding, glass doorknobs, designer lighting, interior laundry with a new washer and dryer, and an upgraded security system. The expansive backyard features mature landscaping and ample space for outdoor enjoyment, with potential for a future pool. The metal-roofed carport includes a ceiling fan and string lights, and Lake Killarney is visible from several areas of the property. The guest cottage includes one bedroom, one bathroom, a living room, and a full kitchen—ideal for guests, extended family, a home office, or as a potential income-producing property. Recent improvements include the main-house roof in 2020; guest-cottage roof in 2022; two new guest-cottage A/C units installed in March 2023; security system in 2023; PVC water line and irrigation pump in 2024; main-house washer and dryer in June 2026; and exterior paint in August 2026. Additional updates include kitchen appliances, lighting and hardware, landscaping and irrigation system with well, interior paint, and a transferable termite bond. Conveniently located within easy walking distance of Hillstone, Trader Joe’s, numerous shops and restaurants, and quick access to I-4. All room dimensions, home & guest cottage square footage, and land square footage are approximate. Buyer to verify.

443 Broadview Avenue, Winter Park

$999,000

Welcome to your fully reimagined Florida home. Among tree-canopied streets in the desired Kenilworth Shores neighborhood, this mid-century modern ranch home was completely transformed in 2005. The redesign added substantial square footage and created a completely unique, functional floor plan that separates it from any other home in the area. Spanning 2,638 square feet of seamless indoor-outdoor living, the property features four bedrooms, 4.5 baths, including three complete en-suite setups that offer maximum privacy for family or guests, plus a dedicated 130-square-foot office. Key property features include elegant design. Step onto gorgeous, rich Brazilian cherry wood flooring that flows beautifully through the open living spaces. Work from home where a dedicated, quiet office space provides an environment for remote work, study or creative projects. Spacious kitchen allows you to enjoy an open-concept floor plan, an eating space in the kitchen, solid wood cabinetry, Silestone countertops and coordinating GE Profile appliances, including a convection oven microwave, giving the kitchen dual oven capacity. Indoor laundry room is a convenient, separate indoor laundry room that keeps household chores organized, quiet and out of sight. Private saltwater oasis allows you to relax in your fully fenced, private backyard featuring an in-ground saltwater pool with spa jets and solar heat. Turnkey infrastructure where peace of mind comes built-in with a new roof (2022), fresh exterior paint and trim (2022), and an updated 200-amp electrical panel. Smart home and systems, equipped with an app-controlled smart security system covering all doors and windows, an EcoBee thermostat and energy-efficient LED recessed lighting. Location and lifestyle benefits include top-tier education, zoned for premier Orange County schools, including Brookshire Elementary, Glenridge Middle School and Winter Park High School (home to a globally recognized International Baccalaureate program). Active recreation to Cady Way Park to enjoy the community pool, playground, sports fields and extensive bike trails. Unbeatable convenience just minutes away from Winter Park Pines Golf Course, two Publix grocery stores, and the upscale dining, boutique shopping, and museums of Park Avenue and Baldwin Park Town Center. This exceptional property blends classic Winter Park lifestyle with the modern infrastructure you demand.

4 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 04 SubDv. ⋅ 32792 Zip Code

Welcome to your fully reimagined Florida home. Among tree-canopied streets in the desired Kenilworth Shores neighborhood, this mid-century modern ranch home was completely transformed in 2005. The redesign added substantial square footage and created a completely unique, functional floor plan that separates it from any other home in the area. Spanning 2,638 square feet of seamless indoor-outdoor living, the property features four bedrooms, 4.5 baths, including three complete en-suite setups that offer maximum privacy for family or guests, plus a dedicated 130-square-foot office. Key property features include elegant design. Step onto gorgeous, rich Brazilian cherry wood flooring that flows beautifully through the open living spaces. Work from home where a dedicated, quiet office space provides an environment for remote work, study or creative projects. Spacious kitchen allows you to enjoy an open-concept floor plan, an eating space in the kitchen, solid wood cabinetry, Silestone countertops and coordinating GE Profile appliances, including a convection oven microwave, giving the kitchen dual oven capacity. Indoor laundry room is a convenient, separate indoor laundry room that keeps household chores organized, quiet and out of sight. Private saltwater oasis allows you to relax in your fully fenced, private backyard featuring an in-ground saltwater pool with spa jets and solar heat. Turnkey infrastructure where peace of mind comes built-in with a new roof (2022), fresh exterior paint and trim (2022), and an updated 200-amp electrical panel. Smart home and systems, equipped with an app-controlled smart security system covering all doors and windows, an EcoBee thermostat and energy-efficient LED recessed lighting. Location and lifestyle benefits include top-tier education, zoned for premier Orange County schools, including Brookshire Elementary, Glenridge Middle School and Winter Park High School (home to a globally recognized International Baccalaureate program). Active recreation to Cady Way Park to enjoy the community pool, playground, sports fields and extensive bike trails. Unbeatable convenience just minutes away from Winter Park Pines Golf Course, two Publix grocery stores, and the upscale dining, boutique shopping, and museums of Park Avenue and Baldwin Park Town Center. This exceptional property blends classic Winter Park lifestyle with the modern infrastructure you demand.

616 Brechin Drive, Winter Park

$998,000

Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed builder Odin Homes. Showcasing over two years of gentle ownership, this exceptional home lives like new and offers a rare opportunity to own a move-in-ready custom home without the wait of new construction. Designed with sophistication and functionality in mind, this 4-bedroom, 4-bath residence features spacious living areas, designer finishes, soaring ceilings, and an open-concept floor plan ideal for both everyday living and entertaining. Every detail reflects Odin Homes' renowned craftsmanship, quality construction, and attention to detail. Perfectly situated on a beautiful homesite in one of Winter Park's most desirable neighborhoods, residents enjoy access to top-rated schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. The location offers exceptional convenience just minutes from Park Avenue's renowned dining and shopping, downtown Orlando, Winter Park Village, major employers, and area attractions. Whether you're searching for a primary residence or simply want the benefits of newer construction without the construction timeline, this exceptional custom home delivers luxury, location, and lifestyle in one of Central Florida's most sought-after communities.

4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed builder Odin Homes. Showcasing over two years of gentle ownership, this exceptional home lives like new and offers a rare opportunity to own a move-in-ready custom home without the wait of new construction. Designed with sophistication and functionality in mind, this 4-bedroom, 4-bath residence features spacious living areas, designer finishes, soaring ceilings, and an open-concept floor plan ideal for both everyday living and entertaining. Every detail reflects Odin Homes' renowned craftsmanship, quality construction, and attention to detail. Perfectly situated on a beautiful homesite in one of Winter Park's most desirable neighborhoods, residents enjoy access to top-rated schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. The location offers exceptional convenience just minutes from Park Avenue's renowned dining and shopping, downtown Orlando, Winter Park Village, major employers, and area attractions. Whether you're searching for a primary residence or simply want the benefits of newer construction without the construction timeline, this exceptional custom home delivers luxury, location, and lifestyle in one of Central Florida's most sought-after communities.

1404 Border Drive, Winter Park

$985,000

Expect to be impressed by this stunning, renovated 5-bedroom, 3-bathroom home in desirable Winter Park, where modern elegance meets timeless charm. Thoughtfully redesigned from top to bottom, this exceptional residence offers a bright, open feel with multiple living spaces perfect for everyday living and entertaining. The light-filled kitchen features quartz countertops, stainless steel appliances, and a custom backsplash, creating a stylish and functional space for cooking and gathering. Spacious family and game rooms provide plenty of room to relax and entertain, while a sun-filled bonus room offers endless possibilities as a home office, playroom, fitness room, or creative space. Two bedrooms on the first floor provide flexibility for guests, a private office, or multigenerational living. Upstairs, the beautifully redesigned primary suite serves as a private retreat, complete with a gorgeous en-suite bathroom featuring a walk-in shower and soaking tub. Two additional bedrooms and a full bathroom complete the second floor, offering comfortable accommodations and room for everyone. Step outside to enjoy the expansive 0.34-acre lot tucked away on a peaceful cul-de-sac, with plenty of space for outdoor entertaining, play, and relaxation. The oversized detached garage offers 500+ additional square feet of versatile space, ideal for hobbies, projects, a workshop, or extra storage. With no HOA restrictions, you’ll have the freedom to make the property your own. The location is just as impressive, with Lake Killarney just steps away and Park Avenue and Winter Park Village only a short drive away for premier shopping, dining, and entertainment. Convenient access to I-4 makes commuting and exploring Central Florida a breeze. Combining thoughtful renovations, flexible living spaces, an oversized lot, and an unbeatable Winter Park location, this home is a rare opportunity to enjoy the best of Florida living. Schedule your private showing today!

5 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

Expect to be impressed by this stunning, renovated 5-bedroom, 3-bathroom home in desirable Winter Park, where modern elegance meets timeless charm. Thoughtfully redesigned from top to bottom, this exceptional residence offers a bright, open feel with multiple living spaces perfect for everyday living and entertaining. The light-filled kitchen features quartz countertops, stainless steel appliances, and a custom backsplash, creating a stylish and functional space for cooking and gathering. Spacious family and game rooms provide plenty of room to relax and entertain, while a sun-filled bonus room offers endless possibilities as a home office, playroom, fitness room, or creative space. Two bedrooms on the first floor provide flexibility for guests, a private office, or multigenerational living. Upstairs, the beautifully redesigned primary suite serves as a private retreat, complete with a gorgeous en-suite bathroom featuring a walk-in shower and soaking tub. Two additional bedrooms and a full bathroom complete the second floor, offering comfortable accommodations and room for everyone. Step outside to enjoy the expansive 0.34-acre lot tucked away on a peaceful cul-de-sac, with plenty of space for outdoor entertaining, play, and relaxation. The oversized detached garage offers 500+ additional square feet of versatile space, ideal for hobbies, projects, a workshop, or extra storage. With no HOA restrictions, you’ll have the freedom to make the property your own. The location is just as impressive, with Lake Killarney just steps away and Park Avenue and Winter Park Village only a short drive away for premier shopping, dining, and entertainment. Convenient access to I-4 makes commuting and exploring Central Florida a breeze. Combining thoughtful renovations, flexible living spaces, an oversized lot, and an unbeatable Winter Park location, this home is a rare opportunity to enjoy the best of Florida living. Schedule your private showing today!

2330 Westminster Ct., Winter Park

$985,000

Located on one of Winter Park's beautiful oak-lined brick streets, 1611 Chestnut Avenue is an extensively renovated and expanded 4-bedroom, 4-bath residence offering nearly 3,000 square feet of thoughtfully designed living space in the highly desirable 32789 ZIP code. Far beyond cosmetic updates, this home has undergone a substantial transformation, including major additions to the rear and second floor, creating a spacious, versatile layout with high-quality finishes and modern comforts throughout. The result is a home that combines the established character of its surroundings with the space and functionality of a contemporary residence. The beautifully redesigned kitchen features quartz countertops, stainless steel appliances, a generous island, farmhouse sink, and adjoining pantry, opening to inviting living and dining areas. Whether preparing a quiet dinner or hosting a gathering, the kitchen's generous workspace and connection to the surrounding rooms make it a natural center of daily life. A separate, expansive family room showcases a stone wood-burning fireplace and custom built-ins, providing another comfortable setting for relaxing or entertaining. Engineered hardwood and luxury vinyl flooring, designer tilework, upgraded fixtures, and beautifully appointed bathrooms reflect the attention and investment devoted to this home. The thoughtful separation of living spaces gives everyone room to enjoy the home in their own way without sacrificing the ease of gathering together. The impressive upstairs primary retreat provides exceptional privacy, featuring a spacious en-suite bathroom with freestanding soaking tub, double vanity, walk-in closet, and dedicated built-in office alcove. Occupying its own upper-level space, this generously proportioned suite feels like a retreat within the home, with room for both a restful bedroom setting and a practical workspace. Three additional bedrooms are located downstairs, including two with en-suite bathrooms. One enjoys an adjoining sitting room with sliding doors opening to the backyard, creating an ideal arrangement for extended family, guests, or multigenerational living. This flexible layout is equally appealing for those seeking a private guest area, a home office, or separate spaces for different daily routines. Additional improvements include an updated roof, newer AC system, a dedicated laundry room, attached two-car garage, and a private fenced backyard surrounded by mature landscaping. The outdoor setting provides space to unwind, enjoy fresh air, or create a welcoming area for casual get-togethers, while the mature trees and greenery reinforce the charm of this established neighborhood. Situated in Winter Park's established Lake Knowles Terrace neighborhood, the property is surrounded by charming residences, beautifully renovated homes, and impressive newer custom construction. Here, brick-paved streets and a canopy of mature oaks create a distinctive streetscape that is increasingly difficult to find. Enjoy convenient access to the Winter Park Chain of Lakes, Winter Park Golf Course, Phelps Park, the YMCA, and the renowned shopping, dining, and cultural attractions of Park Avenue. From neighborhood walks beneath the oaks to an afternoon along Park Avenue, this address places many of Winter Park's most loved destinations close to home. An exceptional combination of extensive improvements, generous living space, flexible accommodations, and a highly sought-after Winter Park location.

4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Located on one of Winter Park's beautiful oak-lined brick streets, 1611 Chestnut Avenue is an extensively renovated and expanded 4-bedroom, 4-bath residence offering nearly 3,000 square feet of thoughtfully designed living space in the highly desirable 32789 ZIP code. Far beyond cosmetic updates, this home has undergone a substantial transformation, including major additions to the rear and second floor, creating a spacious, versatile layout with high-quality finishes and modern comforts throughout. The result is a home that combines the established character of its surroundings with the space and functionality of a contemporary residence. The beautifully redesigned kitchen features quartz countertops, stainless steel appliances, a generous island, farmhouse sink, and adjoining pantry, opening to inviting living and dining areas. Whether preparing a quiet dinner or hosting a gathering, the kitchen's generous workspace and connection to the surrounding rooms make it a natural center of daily life. A separate, expansive family room showcases a stone wood-burning fireplace and custom built-ins, providing another comfortable setting for relaxing or entertaining. Engineered hardwood and luxury vinyl flooring, designer tilework, upgraded fixtures, and beautifully appointed bathrooms reflect the attention and investment devoted to this home. The thoughtful separation of living spaces gives everyone room to enjoy the home in their own way without sacrificing the ease of gathering together. The impressive upstairs primary retreat provides exceptional privacy, featuring a spacious en-suite bathroom with freestanding soaking tub, double vanity, walk-in closet, and dedicated built-in office alcove. Occupying its own upper-level space, this generously proportioned suite feels like a retreat within the home, with room for both a restful bedroom setting and a practical workspace. Three additional bedrooms are located downstairs, including two with en-suite bathrooms. One enjoys an adjoining sitting room with sliding doors opening to the backyard, creating an ideal arrangement for extended family, guests, or multigenerational living. This flexible layout is equally appealing for those seeking a private guest area, a home office, or separate spaces for different daily routines. Additional improvements include an updated roof, newer AC system, a dedicated laundry room, attached two-car garage, and a private fenced backyard surrounded by mature landscaping. The outdoor setting provides space to unwind, enjoy fresh air, or create a welcoming area for casual get-togethers, while the mature trees and greenery reinforce the charm of this established neighborhood. Situated in Winter Park's established Lake Knowles Terrace neighborhood, the property is surrounded by charming residences, beautifully renovated homes, and impressive newer custom construction. Here, brick-paved streets and a canopy of mature oaks create a distinctive streetscape that is increasingly difficult to find. Enjoy convenient access to the Winter Park Chain of Lakes, Winter Park Golf Course, Phelps Park, the YMCA, and the renowned shopping, dining, and cultural attractions of Park Avenue. From neighborhood walks beneath the oaks to an afternoon along Park Avenue, this address places many of Winter Park's most loved destinations close to home. An exceptional combination of extensive improvements, generous living space, flexible accommodations, and a highly sought-after Winter Park location.

1611 Chestnut Avenue, Winter Park

$950,000

Experience the charm of Winter Park living in this beautifully renovated Orwin Manor residence, where more than $41,000 in luxurious upgrades complement timeless character, sophisticated interiors and exceptional outdoor living in one of the area’s most desirable settings. Nestled along a tree-lined street and surrounded by mature landscaping, this 1,947-square-foot home offers two bedrooms, two baths and a versatile floor plan that can be easily converted back to its original three-bedroom configuration, providing flexibility for a home office, guest room or additional bedroom. Inside, rich hardwood flooring, crown molding, plantation shutters and a wood-burning fireplace lend warmth and character to the home, while French doors and abundant windows invite natural light throughout. The kitchen serves as an elegant centerpiece with custom cabinetry, Carrara marble countertops, a gas range and oven, stainless steel appliances, a breakfast bar and generous workspace. A tankless water heater adds modern efficiency and convenience. Multiple living and dining areas create an effortless flow for entertaining, while the expansive primary suite offers a private retreat with ample space for a sitting area. Beyond the interiors, the backyard creates a private resort-style setting rarely found so close to the heart of Winter Park. Fresh landscaping surrounds a saltwater pool, putting green, and expansive paver patio. A covered outdoor living and dining area provides an inviting backdrop for year-round entertaining. Mature trees, manicured hedges and multiple seating areas enhance the sense of privacy, creating a serene escape equally suited for quiet mornings, afternoons by the pool and evenings with guests. A paver driveway and charming covered entry complement the home’s classic architecture, while a Tesla charger adds the convenience of at-home EV charging. Ideally positioned in Orwin Manor, the residence is just minutes from I-4 access and AdventHealth, with convenient proximity to Park Avenue’s renowned boutiques, dining and cafés, as well as College Park and Downtown Orlando. Zoned for Killarney Elementary School, College Park Middle School and Edgewater High School, this distinctive residence presents an exceptional opportunity to enjoy the best of the Winter Park lifestyle.

2 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster SubDv. ⋅ 32789 Zip Code

Experience the charm of Winter Park living in this beautifully renovated Orwin Manor residence, where more than $41,000 in luxurious upgrades complement timeless character, sophisticated interiors and exceptional outdoor living in one of the area’s most desirable settings. Nestled along a tree-lined street and surrounded by mature landscaping, this 1,947-square-foot home offers two bedrooms, two baths and a versatile floor plan that can be easily converted back to its original three-bedroom configuration, providing flexibility for a home office, guest room or additional bedroom. Inside, rich hardwood flooring, crown molding, plantation shutters and a wood-burning fireplace lend warmth and character to the home, while French doors and abundant windows invite natural light throughout. The kitchen serves as an elegant centerpiece with custom cabinetry, Carrara marble countertops, a gas range and oven, stainless steel appliances, a breakfast bar and generous workspace. A tankless water heater adds modern efficiency and convenience. Multiple living and dining areas create an effortless flow for entertaining, while the expansive primary suite offers a private retreat with ample space for a sitting area. Beyond the interiors, the backyard creates a private resort-style setting rarely found so close to the heart of Winter Park. Fresh landscaping surrounds a saltwater pool, putting green, and expansive paver patio. A covered outdoor living and dining area provides an inviting backdrop for year-round entertaining. Mature trees, manicured hedges and multiple seating areas enhance the sense of privacy, creating a serene escape equally suited for quiet mornings, afternoons by the pool and evenings with guests. A paver driveway and charming covered entry complement the home’s classic architecture, while a Tesla charger adds the convenience of at-home EV charging. Ideally positioned in Orwin Manor, the residence is just minutes from I-4 access and AdventHealth, with convenient proximity to Park Avenue’s renowned boutiques, dining and cafés, as well as College Park and Downtown Orlando. Zoned for Killarney Elementary School, College Park Middle School and Edgewater High School, this distinctive residence presents an exceptional opportunity to enjoy the best of the Winter Park lifestyle.

1411 Devon Road, Winter Park

$950,000

913 Moss Lane is in the Vias of Winter Park, on a tree-lined street in Maitland Shores. Neighborhood access to the Winter Park chain of lakes is a block away. Winter Park Racquet Club is a short walk. Park Avenue is a short drive. The home is zoned for Dommerich Elementary, Maitland Middle, and Winter Park High. The house is a 1953 split-level with 3 bedrooms, 2 baths, about 1,887 square feet, and a two-car garage. The main floor has the living room, dining area, kitchen, and Florida room. The bedrooms are upstairs. The 2023 renovation added new flooring, interior and exterior paint, a kitchen with white cabinetry, stone counters, and stainless appliances, and an updated bath with a walk-in glass shower. The backyard is fenced and has a patio. There is no homeowners association. This is a renovated three-bedroom in the Vias. See it for the street, the schools, and the lakes.

3 Beds ⋅ 2 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

913 Moss Lane is in the Vias of Winter Park, on a tree-lined street in Maitland Shores. Neighborhood access to the Winter Park chain of lakes is a block away. Winter Park Racquet Club is a short walk. Park Avenue is a short drive. The home is zoned for Dommerich Elementary, Maitland Middle, and Winter Park High. The house is a 1953 split-level with 3 bedrooms, 2 baths, about 1,887 square feet, and a two-car garage. The main floor has the living room, dining area, kitchen, and Florida room. The bedrooms are upstairs. The 2023 renovation added new flooring, interior and exterior paint, a kitchen with white cabinetry, stone counters, and stainless appliances, and an updated bath with a walk-in glass shower. The backyard is fenced and has a patio. There is no homeowners association. This is a renovated three-bedroom in the Vias. See it for the street, the schools, and the lakes.

913 Moss Lane, Winter Park

$950,000

A RARE WINTER PARK RENOVATION OPPORTUNITY DIRECTLY ACROSS FROM HOWELL BRANCH PRESERVE! Situated on an approximately 0.23-acre lot, this distinctive 3-bedroom, 2-bath home offers an exceptional opportunity for an investor, renovator, or buyer seeking to complete and personalize a property in one of Central Florida’s most desirable communities. Renovations have already begun, providing the next owner with a valuable head start. The home features a spacious open-concept living, dining, and kitchen area; original hardwood flooring in several bedrooms; updated flooring in other areas; renovated bathroom elements; a large walk-in shower; generous flex and storage space; and an expansive driveway and garage area. Some improvements and finish work remain, allowing the buyer to complete the renovation according to their own vision. The approximately 10,219-square-foot lot is directly across from the 10.38-acre Howell Branch Preserve, which offers a playground, fitness trail with exercise stations, picnic pavilion, boardwalk, observation deck, restrooms, open lawn, and protected natural surroundings. Property is offered strictly AS IS. Public records reflect approximately 1,487 square feet of heated living area. Additional areas, measurements, permitted improvements, and intended uses must be independently verified by the buyer. The seller will not complete repairs. Bring your contractor and imagination to explore the possibilities offered by this unique Winter Park property.

3 Beds ⋅ 2 Baths ⋅ Lake Maitland SubDv. ⋅ 32789 Zip Code

A RARE WINTER PARK RENOVATION OPPORTUNITY DIRECTLY ACROSS FROM HOWELL BRANCH PRESERVE! Situated on an approximately 0.23-acre lot, this distinctive 3-bedroom, 2-bath home offers an exceptional opportunity for an investor, renovator, or buyer seeking to complete and personalize a property in one of Central Florida’s most desirable communities. Renovations have already begun, providing the next owner with a valuable head start. The home features a spacious open-concept living, dining, and kitchen area; original hardwood flooring in several bedrooms; updated flooring in other areas; renovated bathroom elements; a large walk-in shower; generous flex and storage space; and an expansive driveway and garage area. Some improvements and finish work remain, allowing the buyer to complete the renovation according to their own vision. The approximately 10,219-square-foot lot is directly across from the 10.38-acre Howell Branch Preserve, which offers a playground, fitness trail with exercise stations, picnic pavilion, boardwalk, observation deck, restrooms, open lawn, and protected natural surroundings. Property is offered strictly AS IS. Public records reflect approximately 1,487 square feet of heated living area. Additional areas, measurements, permitted improvements, and intended uses must be independently verified by the buyer. The seller will not complete repairs. Bring your contractor and imagination to explore the possibilities offered by this unique Winter Park property.

1220 Howell Branch Road, Winter Park

$925,000

Exceptional Winter Park Opportunity with In-Law Suite & Income Potential. THIS HOUSE IS AVAILABLE FOR LEASING OPTION. Discover the opportunity to own a versatile property in one of Central Florida’s most desirable locations. 471 Holt Ave. in Winter Park offers buyers something increasingly valuable: flexibility. With a private in-law suite, this property presents an exciting opportunity for multigenerational living, a guest suite, home office, or potential rental income. For homeowners, the additional living space provides the freedom to accommodate family members or guests while maintaining privacy and separation. For investors, the configuration creates the potential to generate supplemental income, subject to applicable local regulations and requirements. The property’s location adds to its appeal, placing you near Winter Park’s renowned dining, shopping, parks, cultural attractions, and vibrant community amenities. Also, just a walking distance to Rollins College! Whether you’re looking to offset your mortgage, create an additional income stream, or simply secure a property with adaptable living options, this home offers a compelling combination of lifestyle and investment potential. Opportunities with this level of flexibility are hard to find. Live in the main residence, utilize the suite for family or guests, or explore its income-producing potential. 471 Holt Ave. offers the versatility today’s buyers are looking for and the potential long-term value investors appreciate. Don’t miss the opportunity to make this flexible Winter Park property your next home or investment.

4 Beds ⋅ 3 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Exceptional Winter Park Opportunity with In-Law Suite & Income Potential. THIS HOUSE IS AVAILABLE FOR LEASING OPTION. Discover the opportunity to own a versatile property in one of Central Florida’s most desirable locations. 471 Holt Ave. in Winter Park offers buyers something increasingly valuable: flexibility. With a private in-law suite, this property presents an exciting opportunity for multigenerational living, a guest suite, home office, or potential rental income. For homeowners, the additional living space provides the freedom to accommodate family members or guests while maintaining privacy and separation. For investors, the configuration creates the potential to generate supplemental income, subject to applicable local regulations and requirements. The property’s location adds to its appeal, placing you near Winter Park’s renowned dining, shopping, parks, cultural attractions, and vibrant community amenities. Also, just a walking distance to Rollins College! Whether you’re looking to offset your mortgage, create an additional income stream, or simply secure a property with adaptable living options, this home offers a compelling combination of lifestyle and investment potential. Opportunities with this level of flexibility are hard to find. Live in the main residence, utilize the suite for family or guests, or explore its income-producing potential. 471 Holt Ave. offers the versatility today’s buyers are looking for and the potential long-term value investors appreciate. Don’t miss the opportunity to make this flexible Winter Park property your next home or investment.

471 Holt Avenue, Winter Park

$899,900

Welcome to this warm and inviting home in the desirable Brookshire Heights neighborhood, ideally positioned on a corner lot along a beautiful street in a sought-after community. Offering more than 2,500 square feet of living space, this spacious residence features four bedrooms and two-and-a-half baths, with an open, comfortable layout designed for both everyday living and entertaining. The home has been thoughtfully updated and maintained over the years, blending timeless character with modern conveniences. The kitchen was beautifully remodeled in 2021 with new cabinetry, appliances, flooring and countertops, while the family room was enhanced with additional air-conditioning ducts and vents for added comfort. The second full bath was also remodeled in 2021 and the downstairs powder room received a stylish update in 2025.Significant improvements include new wood flooring downstairs and refinished and stained upstairs floors in 2019, a new HVAC system with an additional upstairs unit and complete ductwork replacement in 2020 and a customized primary closet in 2022. The primary suite continues to impress with a new porch door and a private balcony railing added in 2026. A new water heater was installed in 2023, while the main sewer line exiting the home was replaced in 2024. The garage is air-cooled. Outdoor living has been equally well considered, with a screened porch enclosure, a covered side patio, new fencing and refreshed landscaping creating inviting spaces to relax and entertain. Beyond the home itself, the location is exceptional, conveniently situated in a wonderful community with Cady Way pool and Cady Way trail, which spans 7.2 miles and connects to the Seminole Trail outdoor recreation. Highly regarded schools and easy access to the area’s everyday amenities. With its generous living spaces, extensive updates, inviting outdoor areas and prime corner-lot setting, this Brookshire Heights home offers an exceptional opportunity to enjoy a beautifully cared-for residence in a highly desirable location.

4 Beds ⋅ 3 Baths ⋅ Brookshire Heights 2nd Add SubDv. ⋅ 32792 Zip Code

Welcome to this warm and inviting home in the desirable Brookshire Heights neighborhood, ideally positioned on a corner lot along a beautiful street in a sought-after community. Offering more than 2,500 square feet of living space, this spacious residence features four bedrooms and two-and-a-half baths, with an open, comfortable layout designed for both everyday living and entertaining. The home has been thoughtfully updated and maintained over the years, blending timeless character with modern conveniences. The kitchen was beautifully remodeled in 2021 with new cabinetry, appliances, flooring and countertops, while the family room was enhanced with additional air-conditioning ducts and vents for added comfort. The second full bath was also remodeled in 2021 and the downstairs powder room received a stylish update in 2025.Significant improvements include new wood flooring downstairs and refinished and stained upstairs floors in 2019, a new HVAC system with an additional upstairs unit and complete ductwork replacement in 2020 and a customized primary closet in 2022. The primary suite continues to impress with a new porch door and a private balcony railing added in 2026. A new water heater was installed in 2023, while the main sewer line exiting the home was replaced in 2024. The garage is air-cooled. Outdoor living has been equally well considered, with a screened porch enclosure, a covered side patio, new fencing and refreshed landscaping creating inviting spaces to relax and entertain. Beyond the home itself, the location is exceptional, conveniently situated in a wonderful community with Cady Way pool and Cady Way trail, which spans 7.2 miles and connects to the Seminole Trail outdoor recreation. Highly regarded schools and easy access to the area’s everyday amenities. With its generous living spaces, extensive updates, inviting outdoor areas and prime corner-lot setting, this Brookshire Heights home offers an exceptional opportunity to enjoy a beautifully cared-for residence in a highly desirable location.

2572 Fifeshire Drive, Winter Park

$899,000

Reinvented from the ground up for modern living while honoring its 1953 mid-century modern roots, this 4-bedroom, 3-bath Winter Park home blends authentic MCM character with all-new finishes and systems. An open living, dining, and kitchen core opens to a light-filled sitting area, with white oak floors and designer lighting and ceiling fans throughout. The kitchen stuns with Taj Mahal quartzite counters and KitchenAid stainless appliances. Out back, an expanded patio overlooks a private, fenced yard built for gathering. Everything is new: roof, windows, 200-amp electrical, plumbing with new water heater, HVAC ductwork, and Nest thermostat. Best of all, you can live it on foot: walk to East End Market, Kelly's Homemade Ice Cream, Redlight Redlight, Sushi Lola's, and top-rated Audubon Park K-8. Zoned for Winter Park High, and minutes to Park Avenue and Rollins College. A turnkey classic in one of Winter Park's most established, walkable neighborhoods.

4 Beds ⋅ 3 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

Reinvented from the ground up for modern living while honoring its 1953 mid-century modern roots, this 4-bedroom, 3-bath Winter Park home blends authentic MCM character with all-new finishes and systems. An open living, dining, and kitchen core opens to a light-filled sitting area, with white oak floors and designer lighting and ceiling fans throughout. The kitchen stuns with Taj Mahal quartzite counters and KitchenAid stainless appliances. Out back, an expanded patio overlooks a private, fenced yard built for gathering. Everything is new: roof, windows, 200-amp electrical, plumbing with new water heater, HVAC ductwork, and Nest thermostat. Best of all, you can live it on foot: walk to East End Market, Kelly's Homemade Ice Cream, Redlight Redlight, Sushi Lola's, and top-rated Audubon Park K-8. Zoned for Winter Park High, and minutes to Park Avenue and Rollins College. A turnkey classic in one of Winter Park's most established, walkable neighborhoods.

3006 Northwood Boulevard, Winter Park

$875,000

Virtually Staged. FULLY RENOVATED 4-BEDROOM, 3-BATH POOL HOME IN THE HEART OF WINTER PARK! this beautifully updated home sits on a spacious 9,915-square-foot lot surrounded by mature trees and charming streets. Thoughtfully renovated from top to bottom, this move-in-ready property offers modern finishes, major system upgrades, and the Florida lifestyle you've been looking for! Step inside to discover a bright, inviting interior featuring NEW FLOORING THROUGHOUT, NEW WINDOWS, AND FRESH INTERIOR AND EXTERIOR PAINT. The completely remodeled kitchen showcases NEW CABINETRY, NEW APPLIANCES, AND UPDATED FINISHES, creating a stylish and functional space for everyday living and entertaining. Enjoy added peace of mind with a NEW ROOF (2025), NEW AC SYSTEM (2025), AND NEW WATER HEATER.Step outside to your private backyard retreat featuring a FULLY RESURFACED POOL and a spacious, fenced yard perfect for relaxing, entertaining, and enjoying Florida's beautiful weather year-round. The property also features a 2-CAR GARAGE AND AN OVERSIZED DRIVEWAY, providing plenty of additional parking. Washer and dryer are included! Ideally located just minutes from **CADY WAY TRAIL, PARK AVENUE, ROLLINS COLLEGE, AND WINTER PARK PINES GOLF CLUB, with convenient access to shopping, dining, parks, and major roadways. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School. Enjoy the charm of an established Winter Park neighborhood with the convenience of a fully updated home. ALL THE MAJOR UPDATES HAVE BEEN DONE—JUST MOVE IN AND ENJOY! Some photos have been virtually staged.

4 Beds ⋅ 3 Baths ⋅ Brookshire Heights 4th Add SubDv. ⋅ 32792 Zip Code

Virtually Staged. FULLY RENOVATED 4-BEDROOM, 3-BATH POOL HOME IN THE HEART OF WINTER PARK! this beautifully updated home sits on a spacious 9,915-square-foot lot surrounded by mature trees and charming streets. Thoughtfully renovated from top to bottom, this move-in-ready property offers modern finishes, major system upgrades, and the Florida lifestyle you've been looking for! Step inside to discover a bright, inviting interior featuring NEW FLOORING THROUGHOUT, NEW WINDOWS, AND FRESH INTERIOR AND EXTERIOR PAINT. The completely remodeled kitchen showcases NEW CABINETRY, NEW APPLIANCES, AND UPDATED FINISHES, creating a stylish and functional space for everyday living and entertaining. Enjoy added peace of mind with a NEW ROOF (2025), NEW AC SYSTEM (2025), AND NEW WATER HEATER.Step outside to your private backyard retreat featuring a FULLY RESURFACED POOL and a spacious, fenced yard perfect for relaxing, entertaining, and enjoying Florida's beautiful weather year-round. The property also features a 2-CAR GARAGE AND AN OVERSIZED DRIVEWAY, providing plenty of additional parking. Washer and dryer are included! Ideally located just minutes from **CADY WAY TRAIL, PARK AVENUE, ROLLINS COLLEGE, AND WINTER PARK PINES GOLF CLUB, with convenient access to shopping, dining, parks, and major roadways. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School. Enjoy the charm of an established Winter Park neighborhood with the convenience of a fully updated home. ALL THE MAJOR UPDATES HAVE BEEN DONE—JUST MOVE IN AND ENJOY! Some photos have been virtually staged.

618 Blairshire Circle, Winter Park

$860,000

Virtually Staged. Set on nearly an acre in Winter Park, this stately two-story home offers five bedrooms and three and a half bathrooms across more than 3,200 square feet of elegant living space. A dramatic two-story foyer with a sweeping staircase welcomes you into light-filled formal and casual living areas, including a spacious great room anchored by a fireplace. The gourmet island kitchen features rich cabinetry, stainless steel appliances, and generous counter space, flowing effortlessly to the surrounding living and dining spaces finished with wood-look flooring. The expansive primary suite provides a spa-like bath with a soaking tub and a separate glass-enclosed shower, while four additional bedrooms offer ample room for rest or a home office. Outside, a screened, in-ground pool and spa are framed by a paver deck and a large fully fenced yard, complemented by a covered patio and an oversized three-car garage. A rare offering of space and comfort on a generous, secluded lot. Included 100-Day Home Warranty with buyer activation

5 Beds ⋅ 4 Baths ⋅ Lake Ann Estates Unit 3 SubDv. ⋅ 32792 Zip Code

Virtually Staged. Set on nearly an acre in Winter Park, this stately two-story home offers five bedrooms and three and a half bathrooms across more than 3,200 square feet of elegant living space. A dramatic two-story foyer with a sweeping staircase welcomes you into light-filled formal and casual living areas, including a spacious great room anchored by a fireplace. The gourmet island kitchen features rich cabinetry, stainless steel appliances, and generous counter space, flowing effortlessly to the surrounding living and dining spaces finished with wood-look flooring. The expansive primary suite provides a spa-like bath with a soaking tub and a separate glass-enclosed shower, while four additional bedrooms offer ample room for rest or a home office. Outside, a screened, in-ground pool and spa are framed by a paver deck and a large fully fenced yard, complemented by a covered patio and an oversized three-car garage. A rare offering of space and comfort on a generous, secluded lot. Included 100-Day Home Warranty with buyer activation

120 Longbranch Road, Winter Park

$849,900

Under Construction. Welcome to your NEW Home! This residence to-be-built is a rare single story home. This bright open floor-plan features a large great room open to the kitchen. Enjoy dining at the island and plenty of space to entertain, featuring stainless appliances, and an extra large walk-in pantry (6.8 x 7 ft) to meet all your storage needs. The Primary bedroom is located off of the main living with a spacious (10x 6.5 ft) walk in closet. The primary bath features double sinks and a separate shower and soaking tub as well as a private toilet room. All of the secondary bedrooms are generously sized with signifcant built-in closet space. The extra large laundry space gives ample additional storage. 2 Car garage. Summer Kitchen with a grill available to add-on. Don't wait, take this opportunity to make this pre-construction residence you perfect place to call home.

4 Beds ⋅ 3 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

Under Construction. Welcome to your NEW Home! This residence to-be-built is a rare single story home. This bright open floor-plan features a large great room open to the kitchen. Enjoy dining at the island and plenty of space to entertain, featuring stainless appliances, and an extra large walk-in pantry (6.8 x 7 ft) to meet all your storage needs. The Primary bedroom is located off of the main living with a spacious (10x 6.5 ft) walk in closet. The primary bath features double sinks and a separate shower and soaking tub as well as a private toilet room. All of the secondary bedrooms are generously sized with signifcant built-in closet space. The extra large laundry space gives ample additional storage. 2 Car garage. Summer Kitchen with a grill available to add-on. Don't wait, take this opportunity to make this pre-construction residence you perfect place to call home.

2011 Harmon Avenue, Winter Park

$849,000

Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’ Market, and the Chain of Lakes, all just moments from your front door. Built in 2017 by David Weekley, this thoughtfully designed home combines modern luxury with effortless everyday living. Soaring ceilings, oversized windows, and an open-concept floor plan fill the home with natural light and create an inviting atmosphere throughout. The first-floor primary suite offers a private retreat complete with a spa-inspired bath and spacious walk-in closet, while two additional bedrooms, a full bath, and a dedicated laundry room provide flexibility and convenience. Upstairs, the expansive living and entertaining space serves as the heart of the home. The chef’s kitchen is outfitted with custom cabinetry, granite countertops, premium stainless-steel appliances, a large center island, and a natural gas cooktop—perfect for everything from weeknight dinners to hosting friends and family. Sliding glass doors lead to a spacious balcony with new Trex decking, creating the ideal setting for morning coffee, outdoor dining, or evening cocktails overlooking the neighborhood. With professional landscaping maintained by the HOA, this home offers the ultimate low-maintenance, lock-and-leave lifestyle without sacrificing location or luxury. Opportunities to own in such a highly walkable, centrally located Winter Park setting are exceptionally rare. Experience the convenience, charm, and energy of Park Avenue living while enjoying the privacy and comfort of a beautifully appointed residence. This is Winter Park at its finest.

3 Beds ⋅ 3 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code

Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’ Market, and the Chain of Lakes, all just moments from your front door. Built in 2017 by David Weekley, this thoughtfully designed home combines modern luxury with effortless everyday living. Soaring ceilings, oversized windows, and an open-concept floor plan fill the home with natural light and create an inviting atmosphere throughout. The first-floor primary suite offers a private retreat complete with a spa-inspired bath and spacious walk-in closet, while two additional bedrooms, a full bath, and a dedicated laundry room provide flexibility and convenience. Upstairs, the expansive living and entertaining space serves as the heart of the home. The chef’s kitchen is outfitted with custom cabinetry, granite countertops, premium stainless-steel appliances, a large center island, and a natural gas cooktop—perfect for everything from weeknight dinners to hosting friends and family. Sliding glass doors lead to a spacious balcony with new Trex decking, creating the ideal setting for morning coffee, outdoor dining, or evening cocktails overlooking the neighborhood. With professional landscaping maintained by the HOA, this home offers the ultimate low-maintenance, lock-and-leave lifestyle without sacrificing location or luxury. Opportunities to own in such a highly walkable, centrally located Winter Park setting are exceptionally rare. Experience the convenience, charm, and energy of Park Avenue living while enjoying the privacy and comfort of a beautifully appointed residence. This is Winter Park at its finest.

437 N Capen Avenue, Winter Park

$849,000

Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.

2 Beds ⋅ 2 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.

560 Ololu Drive, Winter Park

$845,000

Welcome to 1621 Chestnut Avenue, ideally situated in the heart of Winter Park's coveted "Tree Streets" neighborhood. Offered at $879,000, this single-story block home sits on a generous 50x150' lot and offers 2,022 square feet of living space with 3 bedrooms and 2.5 baths. Whether you envision a thoughtful remodel or a ground-up new build, this property presents outstanding potential in one of Winter Park's most desirable pockets, where similar transformations are already reshaping the streetscape. Inside, tile flooring flows through the main living areas, complementing a versatile layout that includes a formal living room, a combined kitchen and dining area, and a separate den with pocket doors perfect for a home office or media room. The oversized bedrooms offer generous space throughout, including a primary suite with a private en suite bath. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, ideal for family or guests. At the rear of the home, an enclosed sunroom provides a peaceful retreat overlooking the well-manicured backyard, a tranquil spot to relax and unwind. With its prime location, solid bones, and abundant possibilities, 1621 Chestnut Avenue is ready for its next owner to make it their own.

3 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Welcome to 1621 Chestnut Avenue, ideally situated in the heart of Winter Park's coveted "Tree Streets" neighborhood. Offered at $879,000, this single-story block home sits on a generous 50x150' lot and offers 2,022 square feet of living space with 3 bedrooms and 2.5 baths. Whether you envision a thoughtful remodel or a ground-up new build, this property presents outstanding potential in one of Winter Park's most desirable pockets, where similar transformations are already reshaping the streetscape. Inside, tile flooring flows through the main living areas, complementing a versatile layout that includes a formal living room, a combined kitchen and dining area, and a separate den with pocket doors perfect for a home office or media room. The oversized bedrooms offer generous space throughout, including a primary suite with a private en suite bath. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, ideal for family or guests. At the rear of the home, an enclosed sunroom provides a peaceful retreat overlooking the well-manicured backyard, a tranquil spot to relax and unwind. With its prime location, solid bones, and abundant possibilities, 1621 Chestnut Avenue is ready for its next owner to make it their own.

1621 Chestnut Avenue, Winter Park

$836,000

Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Century Modern home nestled in the heart of Winter Park. Designed with character and functionality in mind, this unique residence features abundant natural light, clean architectural lines, and a striking pass-through fireplace that creates the perfect ambiance between living spaces. Enjoy true Florida living with a private backyard pool, ideal for relaxing or entertaining year-round. The home also includes deeded access to a private dock and boat ramp, making boating on beautiful Lake Killarney just steps from your door. Perfectly positioned for convenience and lifestyle, this property is just a 6-minute drive to the upscale shopping and dining of Park Avenue, only 10 minutes from Downtown Orlando and Camping World Stadium, and approximately 35 minutes from Walt Disney World. Whether you're seeking a stylish primary residence or a one-of-a-kind Central Florida retreat, this home delivers the perfect blend of location, design, and lifestyle. Now offering $10,000 Seller Credit! Call to schedule your showing today!

3 Beds ⋅ 3 Baths ⋅ Flamingo Shores SubDv. ⋅ 32789 Zip Code

Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Century Modern home nestled in the heart of Winter Park. Designed with character and functionality in mind, this unique residence features abundant natural light, clean architectural lines, and a striking pass-through fireplace that creates the perfect ambiance between living spaces. Enjoy true Florida living with a private backyard pool, ideal for relaxing or entertaining year-round. The home also includes deeded access to a private dock and boat ramp, making boating on beautiful Lake Killarney just steps from your door. Perfectly positioned for convenience and lifestyle, this property is just a 6-minute drive to the upscale shopping and dining of Park Avenue, only 10 minutes from Downtown Orlando and Camping World Stadium, and approximately 35 minutes from Walt Disney World. Whether you're seeking a stylish primary residence or a one-of-a-kind Central Florida retreat, this home delivers the perfect blend of location, design, and lifestyle. Now offering $10,000 Seller Credit! Call to schedule your showing today!

338 Blue Heron Drive, Winter Park

$829,500

A unique opportunity with two separate structures on one parcel! The main home provides comfortable living, while the second building was previously licensed and used as a daycare and still has many of the necessary features in place. The additional space could also be used for multigenerational living, an in-law suite, guesthouse, home office, potential ADU, or future daycare operation. The property is not currently licensed as a daycare, but it offers plenty of possibilities for the next owner. All future uses are subject to applicable approvals. Showings by appointment only.

4 Beds ⋅ 2 Baths ⋅ 32792 Zip Code

A unique opportunity with two separate structures on one parcel! The main home provides comfortable living, while the second building was previously licensed and used as a daycare and still has many of the necessary features in place. The additional space could also be used for multigenerational living, an in-law suite, guesthouse, home office, potential ADU, or future daycare operation. The property is not currently licensed as a daycare, but it offers plenty of possibilities for the next owner. All future uses are subject to applicable approvals. Showings by appointment only.

1521 Heron Wood Place, Winter Park

$825,000

Welcome to this beautiful Winter Park home where a flagstone, ivy-lined entry sets the tone for the inviting spaces found within. Tucked away on a private .21-acre lot, this 3-bedroom, 3-bathroom home offers 2,488 square feet of thoughtfully designed living space with vaulted ceilings, multiple living areas, and an effortless flow that makes everyday living and entertaining feel natural. From the moment you arrive, the lush new landscaping and charming entry create a warm first impression, while the spacious interior offers plenty of room for family and friends to gather, relax, and enjoy time together. Inside, the home's multiple living areas provide exceptional flexibility, creating inviting spaces for entertaining, casual gatherings, or simply relaxing with family. The kitchen serves as a natural gathering point, featuring white shaker cabinetry, granite countertops, brand-new stainless-steel appliances, a convenient coffee/wine bar, and a breakfast bar with seating for four. Whether hosting friends for dinner or enjoying a quiet morning together, the layout offers space for every occasion. The primary suite, thoughtfully added in 2017, is a private retreat designed for both comfort and relaxation. A dedicated sitting room or office provides additional flexibility, while the spacious walk-in closet offers abundant storage. The expansive ensuite bathroom delivers a true spa-like experience, featuring a large tiled shower with multiple shower heads and a frameless glass enclosure, creating a luxurious place to unwind at the end of the day. A dual vanity with elegant marble countertops and a separate water closet complete this serene retreat. A secondary bedroom with its own ensuite bathroom provides additional comfort and privacy for guests or family members. All bathrooms have been updated, and the bedrooms feature brand-new carpet, while recessed lighting and ceiling fans throughout add to the home's comfort. Step outside to enjoy the privacy of the fully fenced backyard, with fencing replaced in 2025, a brand-new deck, and beautiful new landscaping. The outdoor space offers another inviting setting for relaxing, entertaining, or enjoying Florida's year-round lifestyle. Beyond the home, the location places you just steps from Brookshire Elementary and close to the Cady Way pool, playground, beach volleyball, tennis and pickleball courts, Cady Way Trail, and Winter Park Pines Golf Course. You'll also enjoy convenient access to UCF, Rollins College, Full Sail University, AdventHealth Winter Park, and Crosby Wellness Center, with Orlando International Airport approximately 25 minutes away. With its welcoming entry, versatile living spaces, spa-inspired primary retreat, private setting, and exceptional Winter Park location, this home offers an ideal backdrop for gathering, relaxing, and making memories with family and friends. ROOF(S) - Main - 2022, Family Room - 2019, Primary Suite - 2017 HVAC - 2021 MINI-SPLIT - 2026

3 Beds ⋅ 3 Baths ⋅ Brookshire Heights SubDv. ⋅ 32792 Zip Code

Welcome to this beautiful Winter Park home where a flagstone, ivy-lined entry sets the tone for the inviting spaces found within. Tucked away on a private .21-acre lot, this 3-bedroom, 3-bathroom home offers 2,488 square feet of thoughtfully designed living space with vaulted ceilings, multiple living areas, and an effortless flow that makes everyday living and entertaining feel natural. From the moment you arrive, the lush new landscaping and charming entry create a warm first impression, while the spacious interior offers plenty of room for family and friends to gather, relax, and enjoy time together. Inside, the home's multiple living areas provide exceptional flexibility, creating inviting spaces for entertaining, casual gatherings, or simply relaxing with family. The kitchen serves as a natural gathering point, featuring white shaker cabinetry, granite countertops, brand-new stainless-steel appliances, a convenient coffee/wine bar, and a breakfast bar with seating for four. Whether hosting friends for dinner or enjoying a quiet morning together, the layout offers space for every occasion. The primary suite, thoughtfully added in 2017, is a private retreat designed for both comfort and relaxation. A dedicated sitting room or office provides additional flexibility, while the spacious walk-in closet offers abundant storage. The expansive ensuite bathroom delivers a true spa-like experience, featuring a large tiled shower with multiple shower heads and a frameless glass enclosure, creating a luxurious place to unwind at the end of the day. A dual vanity with elegant marble countertops and a separate water closet complete this serene retreat. A secondary bedroom with its own ensuite bathroom provides additional comfort and privacy for guests or family members. All bathrooms have been updated, and the bedrooms feature brand-new carpet, while recessed lighting and ceiling fans throughout add to the home's comfort. Step outside to enjoy the privacy of the fully fenced backyard, with fencing replaced in 2025, a brand-new deck, and beautiful new landscaping. The outdoor space offers another inviting setting for relaxing, entertaining, or enjoying Florida's year-round lifestyle. Beyond the home, the location places you just steps from Brookshire Elementary and close to the Cady Way pool, playground, beach volleyball, tennis and pickleball courts, Cady Way Trail, and Winter Park Pines Golf Course. You'll also enjoy convenient access to UCF, Rollins College, Full Sail University, AdventHealth Winter Park, and Crosby Wellness Center, with Orlando International Airport approximately 25 minutes away. With its welcoming entry, versatile living spaces, spa-inspired primary retreat, private setting, and exceptional Winter Park location, this home offers an ideal backdrop for gathering, relaxing, and making memories with family and friends. ROOF(S) - Main - 2022, Family Room - 2019, Primary Suite - 2017 HVAC - 2021 MINI-SPLIT - 2026

2345 Brookshire Avenue, Winter Park

$825,000

Winter Park - Located in the gated community of Hawks Crest, this 4-bedroom, 3.5-bath home offers 2,589 square feet of well-designed living space on a premium pond-view lot. Built in 2020, the home features a downstairs primary suite, open-concept living area, and a versatile upstairs loft. Additional highlights include a tile roof, modern finishes, a screened-in patio for outdoor living, and access to community amenities. This home combines location, layout, and value in a beautiful Winter Park gated communities.

4 Beds ⋅ 4 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code

Winter Park - Located in the gated community of Hawks Crest, this 4-bedroom, 3.5-bath home offers 2,589 square feet of well-designed living space on a premium pond-view lot. Built in 2020, the home features a downstairs primary suite, open-concept living area, and a versatile upstairs loft. Additional highlights include a tile roof, modern finishes, a screened-in patio for outdoor living, and access to community amenities. This home combines location, layout, and value in a beautiful Winter Park gated communities.

1131 Wildmeadow Run, Winter Park

$799,999

Welcome to this beautifully maintained 1960s home nestled in one of Winter Park’s desirable neighborhoods, where classic charm meets thoughtful modern updates. Set along picturesque brick streets shaded by mature trees, this inviting home offers a warm, light-filled interior and a private backyard oasis. From the moment you enter, you’ll notice the abundance of natural light and the large windows that frame the living spaces. The spacious living room flows seamlessly into a bright, functional kitchen featuring newer appliances and a large window overlooking the front yard. Just off the kitchen, an indoor laundry room adds everyday convenience. A beautiful sunroom overlooks the private, landscaped backyard and offers a versatile space that could easily serve as a home office, reading room, or additional sitting area. Down the hallway, the spacious primary suite features an en-suite bathroom, ample closet space, and abundant natural light with peaceful views of the backyard. The second bedroom is generously sized and includes a walk-in closet. Step outside to discover a true gardener’s paradise. The lush, private backyard features a beautiful paved patio, winding paved pathway, mature landscaping, and plenty of space to relax, entertain, or enjoy the outdoors. The location is hard to beat, walking distance to the beautiful Lake Knowles and Lake Wilbar, just minutes from Park Avenue, the Winter Park YMCA, AdventHealth Winter Park, Rollins College, the Winter Park Chain of Lakes, golf courses, and an abundance of exceptional dining and shopping. The home also offers access to top-rated Orange County schools. Important updates include a complete remodel and added square footage (2009), a newer roof (2022), regularly maintained HVAC system (2020), hot water heater (2024), updated bathrooms (2025), kitchen appliance updates (2026), and a regularly maintained irrigation system. This special home offers the perfect blend of classic Winter Park character, modern updates, beautiful outdoor living, and an unbeatable location.

2 Beds ⋅ 2 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully maintained 1960s home nestled in one of Winter Park’s desirable neighborhoods, where classic charm meets thoughtful modern updates. Set along picturesque brick streets shaded by mature trees, this inviting home offers a warm, light-filled interior and a private backyard oasis. From the moment you enter, you’ll notice the abundance of natural light and the large windows that frame the living spaces. The spacious living room flows seamlessly into a bright, functional kitchen featuring newer appliances and a large window overlooking the front yard. Just off the kitchen, an indoor laundry room adds everyday convenience. A beautiful sunroom overlooks the private, landscaped backyard and offers a versatile space that could easily serve as a home office, reading room, or additional sitting area. Down the hallway, the spacious primary suite features an en-suite bathroom, ample closet space, and abundant natural light with peaceful views of the backyard. The second bedroom is generously sized and includes a walk-in closet. Step outside to discover a true gardener’s paradise. The lush, private backyard features a beautiful paved patio, winding paved pathway, mature landscaping, and plenty of space to relax, entertain, or enjoy the outdoors. The location is hard to beat, walking distance to the beautiful Lake Knowles and Lake Wilbar, just minutes from Park Avenue, the Winter Park YMCA, AdventHealth Winter Park, Rollins College, the Winter Park Chain of Lakes, golf courses, and an abundance of exceptional dining and shopping. The home also offers access to top-rated Orange County schools. Important updates include a complete remodel and added square footage (2009), a newer roof (2022), regularly maintained HVAC system (2020), hot water heater (2024), updated bathrooms (2025), kitchen appliance updates (2026), and a regularly maintained irrigation system. This special home offers the perfect blend of classic Winter Park character, modern updates, beautiful outdoor living, and an unbeatable location.

1431 Palm Avenue, Winter Park

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