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$1,377,500

Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next chapter. Spanning over 3,500 square feet, this 4-bedroom, 3.5-bath residence offers a formal, well-appointed layout with soaring high ceilings, rich crown molding, and a thoughtful floor plan designed for both comfortable daily living and effortless entertaining. A dedicated first-floor office provides the ideal work-from-home space, while the separate formal dining room adds an air of sophistication perfect for hosting family and friends. The gourmet kitchen is the heart of the home, featuring granite countertops, premium Thermador appliances, and bartop seating — a space equally suited for casual mornings and lively gatherings. The living room opens through French doors to a generous wrap-around screened patio, seamlessly blending indoor and outdoor living in true Florida fashion. The first-floor primary suite is a private retreat, complete with French door access to the patio, a spacious walk-in closet, and a well-appointed en suite bath featuring a double sink vanity, a separate soaking tub, and a walk-in shower. Upstairs, three generously sized guest bedrooms share a hall bath, and a large bonus room and landing offer flexible space for a playroom, media room, or additional lounge area. A large upstairs utility room and additional walk-in storage beneath the stairs ensure that function is never sacrificed. The home is served by two HVAC units, both dated 2017. Beyond the front door, the Windsong community is nothing short of exceptional. Residents enjoy access to two resort-style pools, a splash pad for the little ones, scenic parks, a fishing dock, and coveted chain-of-lakes access complete with use of a community boat — a lifestyle that truly sets Windsong apart. Zoned for A-rated schools and ideally situated just minutes from the vibrant energy of Baldwin Park, Audubon Park, the Mills District, Downtown Orlando, and all that Winter Park has to offer, this address places you at the center of everything. Whether you're drawn to its classic architecture, its unmatched community amenities, or the incredible opportunity to update and truly make it your own, 1421 Chapman Circle is a rare find in one of Central Florida's most beloved neighborhoods.

4 Beds ⋅ 4 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code

Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next chapter. Spanning over 3,500 square feet, this 4-bedroom, 3.5-bath residence offers a formal, well-appointed layout with soaring high ceilings, rich crown molding, and a thoughtful floor plan designed for both comfortable daily living and effortless entertaining. A dedicated first-floor office provides the ideal work-from-home space, while the separate formal dining room adds an air of sophistication perfect for hosting family and friends. The gourmet kitchen is the heart of the home, featuring granite countertops, premium Thermador appliances, and bartop seating — a space equally suited for casual mornings and lively gatherings. The living room opens through French doors to a generous wrap-around screened patio, seamlessly blending indoor and outdoor living in true Florida fashion. The first-floor primary suite is a private retreat, complete with French door access to the patio, a spacious walk-in closet, and a well-appointed en suite bath featuring a double sink vanity, a separate soaking tub, and a walk-in shower. Upstairs, three generously sized guest bedrooms share a hall bath, and a large bonus room and landing offer flexible space for a playroom, media room, or additional lounge area. A large upstairs utility room and additional walk-in storage beneath the stairs ensure that function is never sacrificed. The home is served by two HVAC units, both dated 2017. Beyond the front door, the Windsong community is nothing short of exceptional. Residents enjoy access to two resort-style pools, a splash pad for the little ones, scenic parks, a fishing dock, and coveted chain-of-lakes access complete with use of a community boat — a lifestyle that truly sets Windsong apart. Zoned for A-rated schools and ideally situated just minutes from the vibrant energy of Baldwin Park, Audubon Park, the Mills District, Downtown Orlando, and all that Winter Park has to offer, this address places you at the center of everything. Whether you're drawn to its classic architecture, its unmatched community amenities, or the incredible opportunity to update and truly make it your own, 1421 Chapman Circle is a rare find in one of Central Florida's most beloved neighborhoods.

1421 Chapman Circle, Winter Park

$1,350,000

Modern Winter Park living meets exceptional convenience at this beautifully designed 2023 residence, ideally positioned near Park Avenue and just minutes from Downtown Orlando. Offering nearly 3,000 square feet of thoughtfully designed living space, this 4-bedroom, 4-bath home combines contemporary architecture, abundant natural light, and elevated finishes in one of Central Florida’s most sought-after locations. Oversized windows and an open-concept layout create a bright, seamless connection between the living, dining, and kitchen spaces—equally suited for everyday living and entertaining. At the heart of the home, the gourmet kitchen features premium stainless steel appliances, custom cabinetry, designer backsplash and lighting, and an oversized island with dramatic waterfall-edge quartz countertops and generous seating. The thoughtfully designed floor plan includes a first-floor guest suite and full bath, providing privacy and flexibility for overnight guests, multigenerational living, or a private home office. Upstairs, the spacious primary retreat features a spa-inspired bath with dual vanities, soaking tub, oversized walk-in shower, and a generous walk-in closet enhanced with a custom organization system. Two additional bedroom suites complete the second level. Outside, the fully fenced backyard and covered lanai with summer kitchen create an inviting extension of the home’s living space—perfect for outdoor dining and entertaining year-round. Additional highlights include designer LED lighting, abundant storage, a two-car garage, manicured landscaping, and no HOA. Located near shopping, dining, highly rated schools, Park Avenue, and the best of Winter Park and Orlando, 1320 Orchid Avenue offers the rare opportunity to enjoy newer construction, modern design, and an exceptional location without sacrificing space or privacy. Schedule your private showing today.

4 Beds ⋅ 4 Baths ⋅ Elizabeth Heights Sub SubDv. ⋅ 32789 Zip Code

Modern Winter Park living meets exceptional convenience at this beautifully designed 2023 residence, ideally positioned near Park Avenue and just minutes from Downtown Orlando. Offering nearly 3,000 square feet of thoughtfully designed living space, this 4-bedroom, 4-bath home combines contemporary architecture, abundant natural light, and elevated finishes in one of Central Florida’s most sought-after locations. Oversized windows and an open-concept layout create a bright, seamless connection between the living, dining, and kitchen spaces—equally suited for everyday living and entertaining. At the heart of the home, the gourmet kitchen features premium stainless steel appliances, custom cabinetry, designer backsplash and lighting, and an oversized island with dramatic waterfall-edge quartz countertops and generous seating. The thoughtfully designed floor plan includes a first-floor guest suite and full bath, providing privacy and flexibility for overnight guests, multigenerational living, or a private home office. Upstairs, the spacious primary retreat features a spa-inspired bath with dual vanities, soaking tub, oversized walk-in shower, and a generous walk-in closet enhanced with a custom organization system. Two additional bedroom suites complete the second level. Outside, the fully fenced backyard and covered lanai with summer kitchen create an inviting extension of the home’s living space—perfect for outdoor dining and entertaining year-round. Additional highlights include designer LED lighting, abundant storage, a two-car garage, manicured landscaping, and no HOA. Located near shopping, dining, highly rated schools, Park Avenue, and the best of Winter Park and Orlando, 1320 Orchid Avenue offers the rare opportunity to enjoy newer construction, modern design, and an exceptional location without sacrificing space or privacy. Schedule your private showing today.

1320 Orchid Avenue, Winter Park

$1,350,000

Virtually Staged. Welcome to your dream home in the highly sought-after Lakeside Estates neighborhood in Winter Park! This elegant 6-bedroom, 5-bathroom, 2 laundry rooms residence offers a perfect blend of modern comfort and timeless sophistication for the whole family. From the moment you enter, you will be captivated by the open concept design, high ceilings, an abundance of natural light. The gourmet kitchen features new quartz countertops, stainless steel appliances, and a spacious island that opens to the family and kitchen nook rooms for entertaining. New paint throughout. New garage coating on the floor. There are 2 primary suites, one on each level, that offers a peaceful retreat with a spa-inspired bath and walk in closets. After a long day, step outside to your private oasis complete with a covered lanai and fully screened-in sparkling pool and spa for hosting gatherings. With its beautifully design and prime location, this home is situated in a gated community, with easy access to top rated schools, boutique shopping, restaurants, and all the charm of Winter Park. Ready to call home!!

6 Beds ⋅ 6 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code

Virtually Staged. Welcome to your dream home in the highly sought-after Lakeside Estates neighborhood in Winter Park! This elegant 6-bedroom, 5-bathroom, 2 laundry rooms residence offers a perfect blend of modern comfort and timeless sophistication for the whole family. From the moment you enter, you will be captivated by the open concept design, high ceilings, an abundance of natural light. The gourmet kitchen features new quartz countertops, stainless steel appliances, and a spacious island that opens to the family and kitchen nook rooms for entertaining. New paint throughout. New garage coating on the floor. There are 2 primary suites, one on each level, that offers a peaceful retreat with a spa-inspired bath and walk in closets. After a long day, step outside to your private oasis complete with a covered lanai and fully screened-in sparkling pool and spa for hosting gatherings. With its beautifully design and prime location, this home is situated in a gated community, with easy access to top rated schools, boutique shopping, restaurants, and all the charm of Winter Park. Ready to call home!!

1445 Via Sangro Place, Winter Park

$1,350,000

Welcome to 720 Pansy Ave, a distinctive three-story Winter Park home thoughtfully designed for both everyday living and flexible use. Fully remodeled in 2017, the residence offers a clean, contemporary interior with LVP and tile flooring, recessed lighting, crisp finishes, and an open flow through the main living spaces. The first floor includes a spacious living room, dining area, and a separate office/study/den, providing plenty of room to work, gather, and unwind. At the heart of the home, the modern kitchen features sleek white cabinetry, stainless steel appliances, generous storage, and a wide pass-through that keeps the kitchen connected to the dining and living areas. The first-floor primary suite offers the convenience of main-level living, complete with a walk-in closet and a beautifully finished primary bath featuring a steam shower. Large windows bring natural light into the home, while the neutral finishes create an easy backdrop for a variety of styles. Upstairs, two additional bedrooms are joined by flexible spaces that add to the home’s functionality, including a dedicated storage room on the second floor. Continue to the third level to find an expansive bonus space that can easily serve as a media room, game room, creative studio, home gym, or additional lounge. Practical features include a durable metal roof and a whole-house generator designed to keep the home powered during storms and unexpected outages, providing added comfort and peace of mind. Outside, the private backyard extends the living space with decking, a hot tub, landscaped green space, mature trees, and a gazebo for relaxing or entertaining. The location completes the package, placing you in the heart of the Winter Park lifestyle with convenient access to Park Avenue, known for its boutiques, restaurants, cultural attractions, and community events, as well as nearby Rollins College. Enjoy the character and charm of an established Winter Park neighborhood while remaining close to the shopping, dining, arts, and everyday conveniences that make this area such a desirable place to call home.

3 Beds ⋅ 4 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code

Welcome to 720 Pansy Ave, a distinctive three-story Winter Park home thoughtfully designed for both everyday living and flexible use. Fully remodeled in 2017, the residence offers a clean, contemporary interior with LVP and tile flooring, recessed lighting, crisp finishes, and an open flow through the main living spaces. The first floor includes a spacious living room, dining area, and a separate office/study/den, providing plenty of room to work, gather, and unwind. At the heart of the home, the modern kitchen features sleek white cabinetry, stainless steel appliances, generous storage, and a wide pass-through that keeps the kitchen connected to the dining and living areas. The first-floor primary suite offers the convenience of main-level living, complete with a walk-in closet and a beautifully finished primary bath featuring a steam shower. Large windows bring natural light into the home, while the neutral finishes create an easy backdrop for a variety of styles. Upstairs, two additional bedrooms are joined by flexible spaces that add to the home’s functionality, including a dedicated storage room on the second floor. Continue to the third level to find an expansive bonus space that can easily serve as a media room, game room, creative studio, home gym, or additional lounge. Practical features include a durable metal roof and a whole-house generator designed to keep the home powered during storms and unexpected outages, providing added comfort and peace of mind. Outside, the private backyard extends the living space with decking, a hot tub, landscaped green space, mature trees, and a gazebo for relaxing or entertaining. The location completes the package, placing you in the heart of the Winter Park lifestyle with convenient access to Park Avenue, known for its boutiques, restaurants, cultural attractions, and community events, as well as nearby Rollins College. Enjoy the character and charm of an established Winter Park neighborhood while remaining close to the shopping, dining, arts, and everyday conveniences that make this area such a desirable place to call home.

720 Pansy Avenue, Winter Park

$1,350,000

Lakefront home on over 1 acre in Winter Park with direct frontage on Lake Spier. Positioned on a private, spring-fed lake, this property presents a rare opportunity to build a brand-new luxury residence or thoughtfully renovate the existing home into a refined lakefront retreat. The expansive lot, tranquil water views, and ownership extending into the lake create a setting defined by privacy, nature, and long-term value. Located in one of Winter Park’s most established areas, just minutes from Park Avenue, top-rated schools, and everyday conveniences, this is a unique canvas for those looking to create something truly exceptional. No HOA. No CDD.

3 Beds ⋅ 2 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code

Lakefront home on over 1 acre in Winter Park with direct frontage on Lake Spier. Positioned on a private, spring-fed lake, this property presents a rare opportunity to build a brand-new luxury residence or thoughtfully renovate the existing home into a refined lakefront retreat. The expansive lot, tranquil water views, and ownership extending into the lake create a setting defined by privacy, nature, and long-term value. Located in one of Winter Park’s most established areas, just minutes from Park Avenue, top-rated schools, and everyday conveniences, this is a unique canvas for those looking to create something truly exceptional. No HOA. No CDD.

1881 Lake Spier Drive, Winter Park

$1,325,000

Welcome to an exceptional opportunity in Waters Edge at Hawks Crest, one of Winter Park's premier gated, resort-style communities. Positioned on a desirable premium lot with beautiful water views, this impressive Kerrville II by Meritage Homes combines sophisticated design, generous living spaces, and an incredible outdoor lifestyle. Offering 6 bedrooms, 4.5 bathrooms, and a 3-car garage, this thoughtfully designed residence provides the flexibility today's buyers are looking for. The light-filled interior features an open and inviting layout with upgraded finishes throughout, creating the perfect setting for both everyday living and entertaining. At the center of the home, the gourmet kitchen is designed to impress with premium cabinetry, quartz countertops, a large center island, and high-end appliances. The kitchen opens seamlessly to the main living and dining spaces, making it easy to gather with family and friends. The outdoor living area truly sets this home apart. Step through to the extended lanai and enjoy your own private Florida retreat featuring a heated saltwater, self-cleaning pool and spa, outdoor kitchen, and an impressive screened enclosure enhanced with color-changing lighting for a dramatic evening atmosphere. Solar panels add an additional energy-efficient benefit to the home. The first floor offers exceptional versatility with formal living and dining spaces along with a private guest suite featuring its own en-suite bathroom and convenient access toward the pool area—ideal for guests, extended family, or multi-generational living. Upstairs, the owner's retreat provides a peaceful escape with views overlooking the pool and water. The spa-inspired primary bathroom, upscale finishes, and generous walk-in closets complete the space. Additional bedrooms and flexible living areas offer endless possibilities for a media room, home office, fitness space, playroom, or additional guest accommodations. The 3-car garage includes convenient overhead storage shelving, providing even more functionality and organization. Residents of Hawks Crest enjoy access to outstanding amenities, including a resort-style community pool, clubhouse, fitness center, playground, putting green, and a private dock on Lake Howell. Spend your weekends kayaking, canoeing, paddleboarding, fishing, or simply enjoying the lakefront setting. Ideally located in Winter Park with convenient access to Park Avenue, shopping, dining, entertainment, and cultural attractions, this home offers the perfect combination of luxury, lifestyle, location, and flexibility. Schedule your private showing today and experience everything this exceptional Hawks Crest residence has to offer.

6 Beds ⋅ 4 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to an exceptional opportunity in Waters Edge at Hawks Crest, one of Winter Park's premier gated, resort-style communities. Positioned on a desirable premium lot with beautiful water views, this impressive Kerrville II by Meritage Homes combines sophisticated design, generous living spaces, and an incredible outdoor lifestyle. Offering 6 bedrooms, 4.5 bathrooms, and a 3-car garage, this thoughtfully designed residence provides the flexibility today's buyers are looking for. The light-filled interior features an open and inviting layout with upgraded finishes throughout, creating the perfect setting for both everyday living and entertaining. At the center of the home, the gourmet kitchen is designed to impress with premium cabinetry, quartz countertops, a large center island, and high-end appliances. The kitchen opens seamlessly to the main living and dining spaces, making it easy to gather with family and friends. The outdoor living area truly sets this home apart. Step through to the extended lanai and enjoy your own private Florida retreat featuring a heated saltwater, self-cleaning pool and spa, outdoor kitchen, and an impressive screened enclosure enhanced with color-changing lighting for a dramatic evening atmosphere. Solar panels add an additional energy-efficient benefit to the home. The first floor offers exceptional versatility with formal living and dining spaces along with a private guest suite featuring its own en-suite bathroom and convenient access toward the pool area—ideal for guests, extended family, or multi-generational living. Upstairs, the owner's retreat provides a peaceful escape with views overlooking the pool and water. The spa-inspired primary bathroom, upscale finishes, and generous walk-in closets complete the space. Additional bedrooms and flexible living areas offer endless possibilities for a media room, home office, fitness space, playroom, or additional guest accommodations. The 3-car garage includes convenient overhead storage shelving, providing even more functionality and organization. Residents of Hawks Crest enjoy access to outstanding amenities, including a resort-style community pool, clubhouse, fitness center, playground, putting green, and a private dock on Lake Howell. Spend your weekends kayaking, canoeing, paddleboarding, fishing, or simply enjoying the lakefront setting. Ideally located in Winter Park with convenient access to Park Avenue, shopping, dining, entertainment, and cultural attractions, this home offers the perfect combination of luxury, lifestyle, location, and flexibility. Schedule your private showing today and experience everything this exceptional Hawks Crest residence has to offer.

1117 Wading Waters Circle, Winter Park

$1,319,950

Virtually Staged. Brand new Roof and HVAC systems in 2025 and all new windows 2026. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 4-bathroom home exudes warmth and sophistication, creating an inviting haven for discerning buyers. Sunlight floods every room, highlighting the home’s refined details and creating a luminous, welcoming atmosphere. Step inside to find luxurious plank flooring flowing through the entryway, family room, and guest bedrooms, complemented by polished marble in the formal living room and opulent primary suite. The interior showcases meticulous craftsmanship with recessed lighting, custom cabinetry, and coffered ceilings that add architectural charm. The heart of the home is a gourmet chef’s kitchen, a culinary dream featuring sleek custom cabinetry, a stylish farmhouse sink, a practical pot filler, and top-of-the-line appliances, perfect for both everyday meals and grand entertaining. Outside, a covered lanai invites relaxation. The sparkling pool, featuring a tranquil waterfall, soothing hot tub, and private pool bath creates a private oasis perfect for unwinding or hosting gatherings. The meticulously landscaped backyard, framed by lush greenery, offers a serene retreat for outdoor enjoyment. Soaring vaulted ceilings enhance the airy, open feel throughout the home. Located near the esteemed Rollins College and vibrant Park Avenue, this property is nestled in a charming neighborhood, offering both prestige and access to Winter Park’s finest dining, shopping, and cultural attractions. With a paved parking area, a two-car garage, and dual-zone AC for year-round comfort, this exquisite home is as practical as it is beautiful. Don’t miss the opportunity to own this Winter Park masterpiece, where timeless elegance meets modern luxury. Schedule a showing today and step into a lifestyle of comfort, sophistication, and unparalleled charm at 952 Moss Ln; this true gem is ready to become your forever home.

4 Beds ⋅ 5 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. Brand new Roof and HVAC systems in 2025 and all new windows 2026. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 4-bathroom home exudes warmth and sophistication, creating an inviting haven for discerning buyers. Sunlight floods every room, highlighting the home’s refined details and creating a luminous, welcoming atmosphere. Step inside to find luxurious plank flooring flowing through the entryway, family room, and guest bedrooms, complemented by polished marble in the formal living room and opulent primary suite. The interior showcases meticulous craftsmanship with recessed lighting, custom cabinetry, and coffered ceilings that add architectural charm. The heart of the home is a gourmet chef’s kitchen, a culinary dream featuring sleek custom cabinetry, a stylish farmhouse sink, a practical pot filler, and top-of-the-line appliances, perfect for both everyday meals and grand entertaining. Outside, a covered lanai invites relaxation. The sparkling pool, featuring a tranquil waterfall, soothing hot tub, and private pool bath creates a private oasis perfect for unwinding or hosting gatherings. The meticulously landscaped backyard, framed by lush greenery, offers a serene retreat for outdoor enjoyment. Soaring vaulted ceilings enhance the airy, open feel throughout the home. Located near the esteemed Rollins College and vibrant Park Avenue, this property is nestled in a charming neighborhood, offering both prestige and access to Winter Park’s finest dining, shopping, and cultural attractions. With a paved parking area, a two-car garage, and dual-zone AC for year-round comfort, this exquisite home is as practical as it is beautiful. Don’t miss the opportunity to own this Winter Park masterpiece, where timeless elegance meets modern luxury. Schedule a showing today and step into a lifestyle of comfort, sophistication, and unparalleled charm at 952 Moss Ln; this true gem is ready to become your forever home.

952 Moss Lane, Winter Park

$1,300,000

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

$1,299,000

Step into elevated Florida living with this stunning brand-new residence, where modern design meets lasting quality. Constructed with solid block and steel framing for superior durability, this home is quietly nestled on a cul-de-sac in one of Winter Park’s most up-and-coming areas—without the restrictions of an HOA. Just moments from Interlachen Country Club and the charming Lakemont Heights neighborhood, the location offers both prestige and convenience. From the moment you enter through the impressive double doors, you’re welcomed by a light-filled, open-concept design. Soaring 10-foot ceilings and elegant 8-foot doors create an airy, expansive feel, while abundant natural light highlights the home’s sleek, contemporary finishes. At the heart of the home, the chef-inspired kitchen truly shines. Outfitted with luxurious quartz countertops, stainless steel appliances, and a custom LED-lit wine display, it’s designed to impress. The seamless flow into the living and dining spaces—along with views of the backyard—makes it perfect for entertaining or everyday connection. The primary suite is a private sanctuary, offering a spa-like escape with dual vanities, a spacious dual-entry shower, and a freestanding soaking tub designed for relaxation. With three additional bedrooms, a dedicated office, and 3.5 beautifully appointed bathrooms, this thoughtfully designed single-story home provides nearly 2,500 square feet of flexible living space. Outdoors, your personal retreat awaits. Enjoy year-round Florida living on the covered lanai, complete with a built-in summer kitchen and a custom-designed pool—ideal for hosting or unwinding. The fully fenced yard features new vinyl fencing, fresh sod, and an automated sprinkler system for effortless maintenance. Perfectly positioned near Phelps Park, the Winter Park YMCA, Lakemont Elementary, and an array of top-tier shopping and dining destinations, this home delivers the ideal blend of privacy, craftsmanship, and everyday luxury.

4 Beds ⋅ 4 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code

Step into elevated Florida living with this stunning brand-new residence, where modern design meets lasting quality. Constructed with solid block and steel framing for superior durability, this home is quietly nestled on a cul-de-sac in one of Winter Park’s most up-and-coming areas—without the restrictions of an HOA. Just moments from Interlachen Country Club and the charming Lakemont Heights neighborhood, the location offers both prestige and convenience. From the moment you enter through the impressive double doors, you’re welcomed by a light-filled, open-concept design. Soaring 10-foot ceilings and elegant 8-foot doors create an airy, expansive feel, while abundant natural light highlights the home’s sleek, contemporary finishes. At the heart of the home, the chef-inspired kitchen truly shines. Outfitted with luxurious quartz countertops, stainless steel appliances, and a custom LED-lit wine display, it’s designed to impress. The seamless flow into the living and dining spaces—along with views of the backyard—makes it perfect for entertaining or everyday connection. The primary suite is a private sanctuary, offering a spa-like escape with dual vanities, a spacious dual-entry shower, and a freestanding soaking tub designed for relaxation. With three additional bedrooms, a dedicated office, and 3.5 beautifully appointed bathrooms, this thoughtfully designed single-story home provides nearly 2,500 square feet of flexible living space. Outdoors, your personal retreat awaits. Enjoy year-round Florida living on the covered lanai, complete with a built-in summer kitchen and a custom-designed pool—ideal for hosting or unwinding. The fully fenced yard features new vinyl fencing, fresh sod, and an automated sprinkler system for effortless maintenance. Perfectly positioned near Phelps Park, the Winter Park YMCA, Lakemont Elementary, and an array of top-tier shopping and dining destinations, this home delivers the ideal blend of privacy, craftsmanship, and everyday luxury.

102 Bell Place, Winter Park

$1,275,000

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

$1,262,500

Welcome to one of Winter Park's most impressive move-in-ready homes, where luxury, comfort, and location come together seamlessly. Completely reimagined and renovated, this stunning 4-bedroom, 4-bath residence offers the rare combination of modern construction quality and an established Winter Park location just minutes from Baldwin Park, Park Avenue, Rollins College, and top-rated schools. From the moment you arrive, the circular driveway, modern architecture, and professional landscaping create a memorable first impression. Inside, soaring natural light and oversized porcelain tile floors lead you through an open-concept floor plan designed for both everyday living and entertaining. The heart of the home is an extraordinary chef's kitchen featuring premium Bosch appliances, an oversized quartz island, custom cabinetry, a walk-in pantry, and a stylish wet bar. Whether hosting holiday gatherings or enjoying a quiet morning coffee, this space was designed to bring family together. The private owner's retreat feels like a luxury resort, offering direct pool access, a spa-inspired bathroom, soaking tub, oversized walk-in shower, custom closet, and a private beverage station for added convenience. Step outside and discover what truly sets this property apart. The backyard was designed for Florida living at its finest, featuring a sparkling pool, expansive covered lanai, outdoor dining area, and a fully equipped summer kitchen complete with grill, refrigeration, storage, and sink. It's the perfect setting for family gatherings, weekend entertaining, or relaxing after a long day. A dedicated office, versatile flex room, pool bath, and guest suite provide the flexibility today's buyers demand for work, fitness, hobbies, multigenerational living, or media space. Beyond the home itself, you'll enjoy a lifestyle few locations can match. Walk or bike to nearby parks and trails, spend evenings dining on Park Avenue, explore Baldwin Park's restaurants and shops, and enjoy quick access to Downtown Orlando and Orlando International Airport. With luxury finishes, smart-home upgrades, resort-style outdoor living, and a premier Winter Park address, this is more than a home—it's a lifestyle opportunity rarely available in Kenilworth Shores. Schedule your private showing today and experience the difference for yourself.

4 Beds ⋅ 4 Baths ⋅ Kenilworth Shores Sec 07 SubDv. ⋅ 32792 Zip Code

Welcome to one of Winter Park's most impressive move-in-ready homes, where luxury, comfort, and location come together seamlessly. Completely reimagined and renovated, this stunning 4-bedroom, 4-bath residence offers the rare combination of modern construction quality and an established Winter Park location just minutes from Baldwin Park, Park Avenue, Rollins College, and top-rated schools. From the moment you arrive, the circular driveway, modern architecture, and professional landscaping create a memorable first impression. Inside, soaring natural light and oversized porcelain tile floors lead you through an open-concept floor plan designed for both everyday living and entertaining. The heart of the home is an extraordinary chef's kitchen featuring premium Bosch appliances, an oversized quartz island, custom cabinetry, a walk-in pantry, and a stylish wet bar. Whether hosting holiday gatherings or enjoying a quiet morning coffee, this space was designed to bring family together. The private owner's retreat feels like a luxury resort, offering direct pool access, a spa-inspired bathroom, soaking tub, oversized walk-in shower, custom closet, and a private beverage station for added convenience. Step outside and discover what truly sets this property apart. The backyard was designed for Florida living at its finest, featuring a sparkling pool, expansive covered lanai, outdoor dining area, and a fully equipped summer kitchen complete with grill, refrigeration, storage, and sink. It's the perfect setting for family gatherings, weekend entertaining, or relaxing after a long day. A dedicated office, versatile flex room, pool bath, and guest suite provide the flexibility today's buyers demand for work, fitness, hobbies, multigenerational living, or media space. Beyond the home itself, you'll enjoy a lifestyle few locations can match. Walk or bike to nearby parks and trails, spend evenings dining on Park Avenue, explore Baldwin Park's restaurants and shops, and enjoy quick access to Downtown Orlando and Orlando International Airport. With luxury finishes, smart-home upgrades, resort-style outdoor living, and a premier Winter Park address, this is more than a home—it's a lifestyle opportunity rarely available in Kenilworth Shores. Schedule your private showing today and experience the difference for yourself.

2015 Summerfield Road, Winter Park

$1,250,000

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

$1,250,000

Rare lakefront opportunity on the beautiful pristine Lake Killarney in the heart of Winter Park! Build your dream home on this coveted corner lot graced by original brick streets. Lake Killarney is a crystal-clear, spring-fed private lake — motorized boats welcome, yet no public boat ramp ensures a peaceful, exclusive experience. Enjoy sweeping 1-mile sunset views from one of only three homes on a quiet dead-end street. Walk to Hillstone, Trader Joe's, and 20+ world-class restaurants. An additional 40 X 65 ft from rear lot line is available to purchase to extend the footprint of your dream home. This extended lot size will create approx 10,075 sf lot to apply the City of Winter Park floor area ratio. This is Florida lakefront living at its finest — don't miss it! Adding additional lot square footage brings price to $1,450,000. TOTAL LOT SQUARE FOOTAGE IS CLOSER TO 11,000 SQUARE FEET WHEN LAKEFRONT PORTION OF LOT IS ADDED IN WITH BUILDABLE SF AT 10,0075. ADDITIONALLY SELLER OWNS THE SMALL COTTAGE HOUSE NEXT DOOR AND IS OPEN TO SUBDIVIDING THAT LOT WHICH WOULD ADD 30 X 155 TO CORNER LOT CREATING A 14,725 SQ FT LOT. PRICE WILL GO UP FOR THIS ADDITIONAL PARCEL.

3 Beds ⋅ 2 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code

Rare lakefront opportunity on the beautiful pristine Lake Killarney in the heart of Winter Park! Build your dream home on this coveted corner lot graced by original brick streets. Lake Killarney is a crystal-clear, spring-fed private lake — motorized boats welcome, yet no public boat ramp ensures a peaceful, exclusive experience. Enjoy sweeping 1-mile sunset views from one of only three homes on a quiet dead-end street. Walk to Hillstone, Trader Joe's, and 20+ world-class restaurants. An additional 40 X 65 ft from rear lot line is available to purchase to extend the footprint of your dream home. This extended lot size will create approx 10,075 sf lot to apply the City of Winter Park floor area ratio. This is Florida lakefront living at its finest — don't miss it! Adding additional lot square footage brings price to $1,450,000. TOTAL LOT SQUARE FOOTAGE IS CLOSER TO 11,000 SQUARE FEET WHEN LAKEFRONT PORTION OF LOT IS ADDED IN WITH BUILDABLE SF AT 10,0075. ADDITIONALLY SELLER OWNS THE SMALL COTTAGE HOUSE NEXT DOOR AND IS OPEN TO SUBDIVIDING THAT LOT WHICH WOULD ADD 30 X 155 TO CORNER LOT CREATING A 14,725 SQ FT LOT. PRICE WILL GO UP FOR THIS ADDITIONAL PARCEL.

120 Broadview Avenue, Winter Park

$1,250,000

Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction, MJS Designers, and Collins & Co. From concept to completion, every detail is thoughtfully orchestrated, allowing the future owner to tailor finishes, layout, and architectural style to match their vision. Ideally positioned just minutes from Park Avenue’s renowned dining, boutique shopping, and vibrant lifestyle, the property also offers convenient access to I-4, College Park, and Downtown Orlando—delivering both prestige and connectivity. The proposed residence spans approximately 2,500 square feet and is designed with intentional flow, abundant natural light, and refined modern finishes. The layout allows for elevated indoor-outdoor living, with the option to incorporate a private pool and outdoor entertaining space. Located within close proximity to major medical centers, including AdventHealth Winter Park (approximately 2.5 miles), AdventHealth Orlando (approximately 4 miles), and Orlando Health Orlando Regional Medical Center (approximately 5 miles), this location offers both lifestyle and practical convenience for medical professionals and those seeking proximity to top-tier healthcare. Opportunities like this are increasingly limited in Winter Park—secure your homesite and begin designing a one-of-a-kind residence in one of Central Florida’s most desirable zip codes.

4 Beds ⋅ 4 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction, MJS Designers, and Collins & Co. From concept to completion, every detail is thoughtfully orchestrated, allowing the future owner to tailor finishes, layout, and architectural style to match their vision. Ideally positioned just minutes from Park Avenue’s renowned dining, boutique shopping, and vibrant lifestyle, the property also offers convenient access to I-4, College Park, and Downtown Orlando—delivering both prestige and connectivity. The proposed residence spans approximately 2,500 square feet and is designed with intentional flow, abundant natural light, and refined modern finishes. The layout allows for elevated indoor-outdoor living, with the option to incorporate a private pool and outdoor entertaining space. Located within close proximity to major medical centers, including AdventHealth Winter Park (approximately 2.5 miles), AdventHealth Orlando (approximately 4 miles), and Orlando Health Orlando Regional Medical Center (approximately 5 miles), this location offers both lifestyle and practical convenience for medical professionals and those seeking proximity to top-tier healthcare. Opportunities like this are increasingly limited in Winter Park—secure your homesite and begin designing a one-of-a-kind residence in one of Central Florida’s most desirable zip codes.

1870 Staunton Avenue, Winter Park

$1,249,900

Pre-Construction. To be built. NEW CONSTRUCTION! Introducing an exquisite new construction home in Winter Park Grove, Winter Park's newest community! This residence is carefully curated by SGC Development, a highly respected local builder known for their dedication to quality and craftsmanship. This residence combines luxury living with the utmost convenience, located within walking distance to Publix and a variety of restaurants, and just minutes from vibrant Park Avenue. This light-filled, open-concept design showcases high-end finishes throughout. The chef’s kitchen is a true centerpiece, featuring premium Bosch appliances, a 36-inch gas range, a built-in coffee bar, and a spacious island with ample storage, creating a perfect culinary haven. The main level includes an ensuite bedroom, ideal for guests or a home office. Upstairs, discover two additional guest bedrooms, along with a luxurious primary suite that boasts a large walk-in closet and a spa-inspired bathroom. A versatile media/bonus room completes the upper level, perfect for entertainment or relaxation. Don’t miss this rare opportunity to own a thoughtfully designed home in Winter Park Grove, where modern elegance meets an unbeatable location. Schedule your private showing today! The pictures are of a model home with similar features- you can still customize to suit your needs!

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

Pre-Construction. To be built. NEW CONSTRUCTION! Introducing an exquisite new construction home in Winter Park Grove, Winter Park's newest community! This residence is carefully curated by SGC Development, a highly respected local builder known for their dedication to quality and craftsmanship. This residence combines luxury living with the utmost convenience, located within walking distance to Publix and a variety of restaurants, and just minutes from vibrant Park Avenue. This light-filled, open-concept design showcases high-end finishes throughout. The chef’s kitchen is a true centerpiece, featuring premium Bosch appliances, a 36-inch gas range, a built-in coffee bar, and a spacious island with ample storage, creating a perfect culinary haven. The main level includes an ensuite bedroom, ideal for guests or a home office. Upstairs, discover two additional guest bedrooms, along with a luxurious primary suite that boasts a large walk-in closet and a spa-inspired bathroom. A versatile media/bonus room completes the upper level, perfect for entertainment or relaxation. Don’t miss this rare opportunity to own a thoughtfully designed home in Winter Park Grove, where modern elegance meets an unbeatable location. Schedule your private showing today! The pictures are of a model home with similar features- you can still customize to suit your needs!

Winter Park

$1,150,000

Welcome to this charming 3 bedroom, 2 bath home located in the highly desirable area of Winter Park. Situated on an oversized lot, this property offers both comfort and space with a layout designed for everyday living and entertaining. The home features a inviting living area along with a unique sunken sunroom just off the two-car garage; perfect for a relaxing sitting room, home office, or play space. The well-appointed kitchen and dining areas flow easily into the main living spaces, creating a warm and functional environment for family and guests. Step outside to your private backyard retreat where you’ll find a sparkling pool and hot tub surrounded by a huge yard, offering plenty of room for outdoor gatherings, gardening, or simply enjoying Florida living. With its generous lot size, thoughtful layout, and prime Winter Park location close to shopping, dining, and top-rated schools, this home is a wonderful opportunity for anyone looking to enjoy the best of Central Florida living.

3 Beds ⋅ 2 Baths ⋅ Banks Colonial Estates SubDv. ⋅ 32789 Zip Code

Welcome to this charming 3 bedroom, 2 bath home located in the highly desirable area of Winter Park. Situated on an oversized lot, this property offers both comfort and space with a layout designed for everyday living and entertaining. The home features a inviting living area along with a unique sunken sunroom just off the two-car garage; perfect for a relaxing sitting room, home office, or play space. The well-appointed kitchen and dining areas flow easily into the main living spaces, creating a warm and functional environment for family and guests. Step outside to your private backyard retreat where you’ll find a sparkling pool and hot tub surrounded by a huge yard, offering plenty of room for outdoor gatherings, gardening, or simply enjoying Florida living. With its generous lot size, thoughtful layout, and prime Winter Park location close to shopping, dining, and top-rated schools, this home is a wonderful opportunity for anyone looking to enjoy the best of Central Florida living.

1600 S Pennsylvania Avenue, Winter Park

$1,105,000

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

$1,100,000

A rare corner lot in one of Winter Park's most established, increasingly in-demand Lake Forest Park neighborhood. This mid-century home has been meticulously maintained. With beautiful hardwood floors and updated systems throughout, there's nothing left to do but move in. The lot is the story here. A stunning mature oak anchors the front yard, and the corner position with no north-facing neighbor gives you privacy that's hard to find this close to town. Out back, a covered porch overlooks Lake Forest, plus a private sauna and a large shed built for a workshop, storage, or a future ADU. Quiet, shaded, genuinely peaceful. The kind of backyard people forget exists in-town. The street is whisper-quiet and made for evening walks, with Lake Forest views most homes in the area can't touch. Move in as-is and enjoy a home that's already been cared for the right way. Or use the lot and elevation to add a second story and expand the lake views, or build new entirely. Lake Forest is in the middle of a real transformation, with new luxury construction going up throughout the neighborhood. This lot puts you ahead of that curve - schedule your private viewing today.

3 Beds ⋅ 3 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

A rare corner lot in one of Winter Park's most established, increasingly in-demand Lake Forest Park neighborhood. This mid-century home has been meticulously maintained. With beautiful hardwood floors and updated systems throughout, there's nothing left to do but move in. The lot is the story here. A stunning mature oak anchors the front yard, and the corner position with no north-facing neighbor gives you privacy that's hard to find this close to town. Out back, a covered porch overlooks Lake Forest, plus a private sauna and a large shed built for a workshop, storage, or a future ADU. Quiet, shaded, genuinely peaceful. The kind of backyard people forget exists in-town. The street is whisper-quiet and made for evening walks, with Lake Forest views most homes in the area can't touch. Move in as-is and enjoy a home that's already been cared for the right way. Or use the lot and elevation to add a second story and expand the lake views, or build new entirely. Lake Forest is in the middle of a real transformation, with new luxury construction going up throughout the neighborhood. This lot puts you ahead of that curve - schedule your private viewing today.

2227 Howard Drive, Winter Park

$1,075,000

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

$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

Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace that anchors the main living space. The renovated kitchen is thoughtfully designed with both everyday living and entertaining in mind, flowing seamlessly into the dining and living areas. A dedicated office provides the perfect work from home setup or quiet retreat, while the flexible layout offers plenty of room for guests, growing families, or multi generational living. Outside, enjoy a private backyard with a charming fire pit and rock gathering are deal for relaxing evenings or hosting friends. The oversized lot also offers ample space to add a pool and create your own backyard oasis. Additional highlights include a 2-car garage, roof replaced in 2018, home repiped in 2019, and updated AC for peace of mind. This is a rare opportunity to own a move-in ready home in one of Winter Park’s most sought after neighborhoods, walking distance to the Audubon Park Garden District with amazing dining, and shopping.

5 Beds ⋅ 3 Baths ⋅ Parklando SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace that anchors the main living space. The renovated kitchen is thoughtfully designed with both everyday living and entertaining in mind, flowing seamlessly into the dining and living areas. A dedicated office provides the perfect work from home setup or quiet retreat, while the flexible layout offers plenty of room for guests, growing families, or multi generational living. Outside, enjoy a private backyard with a charming fire pit and rock gathering are deal for relaxing evenings or hosting friends. The oversized lot also offers ample space to add a pool and create your own backyard oasis. Additional highlights include a 2-car garage, roof replaced in 2018, home repiped in 2019, and updated AC for peace of mind. This is a rare opportunity to own a move-in ready home in one of Winter Park’s most sought after neighborhoods, walking distance to the Audubon Park Garden District with amazing dining, and shopping.

2702 Parkland Drive, Winter Park

$1,025,000

Curated with intention and finished without compromise, 1120 Wisconsin Avenue is a rare opportunity to own a bespoke Winter Park residence where elevated design meets effortless everyday living. Every detail of this 2,213-square-foot, three-bedroom, three-and-a-half-bath home has been thoughtfully considered — from the custom Pella® multi-point entry door that welcomes you into a light-filled, open-concept gathering room, to the chef's kitchen anchored by a dramatic waterfall island and ZLINE commercial-style gas range with soft-close cabinetry and curated high-end appliances throughout. A private courtyard entry sets a serene tone before you've even stepped inside. The seamless indoor-outdoor connection continues through Pella® wood-clad sliding glass doors to a covered BBQ kitchen lanai — your own tranquil outdoor retreat. The primary suite is a true sanctuary: a generous walk-in closet, a sitting area, linen storage, and a spa-caliber bathroom with a double-sink vanity and oversized walk-in shower. Upstairs, two spacious en-suite bedrooms and a versatile loft with built-in storage offer flexibility for guests, family, or a refined home office. Finished with stunning hardwood floors, soaring ceilings, custom window treatments, spray foam insulation, and dual-zone climate control, this home is as quietly practical as it is undeniably beautiful. Whether you're entertaining or simply unwinding, 1120 Wisconsin Avenue offers the ease and elegance of a true lock-and-leave lifestyle in one of Winter Park's most sought-after neighborhoods.

3 Beds ⋅ 4 Baths ⋅ Henkel Add SubDv. ⋅ 32789 Zip Code

Curated with intention and finished without compromise, 1120 Wisconsin Avenue is a rare opportunity to own a bespoke Winter Park residence where elevated design meets effortless everyday living. Every detail of this 2,213-square-foot, three-bedroom, three-and-a-half-bath home has been thoughtfully considered — from the custom Pella® multi-point entry door that welcomes you into a light-filled, open-concept gathering room, to the chef's kitchen anchored by a dramatic waterfall island and ZLINE commercial-style gas range with soft-close cabinetry and curated high-end appliances throughout. A private courtyard entry sets a serene tone before you've even stepped inside. The seamless indoor-outdoor connection continues through Pella® wood-clad sliding glass doors to a covered BBQ kitchen lanai — your own tranquil outdoor retreat. The primary suite is a true sanctuary: a generous walk-in closet, a sitting area, linen storage, and a spa-caliber bathroom with a double-sink vanity and oversized walk-in shower. Upstairs, two spacious en-suite bedrooms and a versatile loft with built-in storage offer flexibility for guests, family, or a refined home office. Finished with stunning hardwood floors, soaring ceilings, custom window treatments, spray foam insulation, and dual-zone climate control, this home is as quietly practical as it is undeniably beautiful. Whether you're entertaining or simply unwinding, 1120 Wisconsin Avenue offers the ease and elegance of a true lock-and-leave lifestyle in one of Winter Park's most sought-after neighborhoods.

1120 Wisconsin Avenue, Winter Park

$999,000

Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. Updated TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!

3 Beds ⋅ 3 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. Updated TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!

1138 S Pennsylvania 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

$995,999

Exceptional Winter Park Opportunity with In-Law Suite & Income Potential 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 short 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 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 short 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

$995,000

HUGE PRICE IMPROVEMENT!!Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood, unique charm and character, and the bones of new construction. Gutted to the studs and rebuilt with intention, every major system is new — every step of this rennovation was completed with quality and permanence in mind. With elevated finishes, like designer tile and quartz countertops, beautifully reimagined kitchen and baths. A second-floor addition adds a sprawling 21 x 24 foot private primary suite and home office, one of the many reasons this an ideal setup for MULTIGENERATIONAL families and those who work from home. A welcoming fireplace, lush mature landscaping, butler's pantry, numerous built ins, custom tile work, and an address minutes from Park Avenue make this one of Winter Park's most compelling offerings. Come imagine the possibilities.

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

HUGE PRICE IMPROVEMENT!!Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood, unique charm and character, and the bones of new construction. Gutted to the studs and rebuilt with intention, every major system is new — every step of this rennovation was completed with quality and permanence in mind. With elevated finishes, like designer tile and quartz countertops, beautifully reimagined kitchen and baths. A second-floor addition adds a sprawling 21 x 24 foot private primary suite and home office, one of the many reasons this an ideal setup for MULTIGENERATIONAL families and those who work from home. A welcoming fireplace, lush mature landscaping, butler's pantry, numerous built ins, custom tile work, and an address minutes from Park Avenue make this one of Winter Park's most compelling offerings. Come imagine the possibilities.

1611 Chestnut Avenue, Winter Park

$989,500

Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine dining, boutique shopping, the Morse Museum, Rollins College, and the scenic Chain of Lakes. Whether you’re downsizing, escaping winter months or seeking a refined second home, this residence delivers the perfect blend of luxury, simplicity, and prestige. Designed for comfort and ease, the home welcomes you with a bright, open living space enhanced by crown molding, warm natural light, and a seamless flow ideal for both quiet escapes and intimate entertaining. The primary suite features a generous walk-in closet, while the kitchen offers modern functionality with quality appliances and thoughtful storage. This unit offers its own washer/dryer combo unit, large exterior storage closet, assigned parking space under canopy and extra open parking spaces. Please note rentals are not allowed and no pets except for Service Animals.

1 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code

Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine dining, boutique shopping, the Morse Museum, Rollins College, and the scenic Chain of Lakes. Whether you’re downsizing, escaping winter months or seeking a refined second home, this residence delivers the perfect blend of luxury, simplicity, and prestige. Designed for comfort and ease, the home welcomes you with a bright, open living space enhanced by crown molding, warm natural light, and a seamless flow ideal for both quiet escapes and intimate entertaining. The primary suite features a generous walk-in closet, while the kitchen offers modern functionality with quality appliances and thoughtful storage. This unit offers its own washer/dryer combo unit, large exterior storage closet, assigned parking space under canopy and extra open parking spaces. Please note rentals are not allowed and no pets except for Service Animals.

269 E Canton Avenue Unit 269, Winter Park

$985,000

A MUST SEE BEAUTIFUL WELL MAINTAINED POOL HOME by ORIGINAL OWNERS in SOUGHT AFTER WINTER PARK ZIPCODE & SCHOOLS. PICTURES PROVIDE a GREAT PORTRAYAL of the FLOORPLAN but THERE ARE MANY FEATURES TO POINT OUT - THIS 2868 SQFT HOME has a 3-WAY SPLIT with 4 BEDROOMS, 3 FULL BATHROOMS, plus BONUS ROOM & OFFICE. YOU WILL NOT BELIEVE ALL THE STORAGE, STORAGE, STORAGE UNDER AIR! The BONUS ROOM (12.4 X 11.7) OFF PRIMARY BEDROOM COULD BE a NURSERY, OFFICE, EXERCISE ROOM, or OWNERS RETREAT. There is an ADDITIONAL OFFICE (13.6 X 11.6 ) with BUILT N DESK & STORAGE CABINETS MAKING a GREAT HOMESCHOOL ROOM, CRAFT AREA, or HOME OFFICE WHERE a PRIVATE EXTERIOR ENTRY DOOR is NEEDED. ONE BEDROOM could be USED as an IN-LAW SUITE with IT’S ENSUITE BATHROOM with SHOWER. The SPACIOUS GARAGE has NEW SHARK FLOORING (7/26), NEW PAINT, NEW ELECTRIC CAR CHARGING OUTLET (6/26), NEW INSULATED GARAGE DOOR & A MINI SPLIT AC – LOTS OF POSSIBILITIES! MANY FUN MEMORIES can be ENJOYED with FAMILY & FRIENDS AROUND the BEAUTIFUL SCREENED POOL & LARGE COVERED LANAI & DECK ( RESURFACED 9/25 ) The NEW OWNER of this LOVELY HOME will APPRECIATE all the UPDATES that have BEEN DONE over LAST FEW YEARS – NEW $29K LENOX UPGRADED AC (3/26), NEW FRONT DOOR (4/26), NEW GOOGLE NEST DOORBELL (3/26), NEW INSULATION in ATTIC & ON GARAGE DOOR (6/26), NEW PAVER DRIVEWAY (5/26 ) NEW UPGRADED FLASHING AROUND CHIMNEY (5/26), GAS TANKLESS WATER HEATER W RECIRCULATING FEATURE(2023), NEW DUCT WORK (2019) NEW WINDOWS (2020), WHOLE HOUSE REPLUMBED (2020), ROOF (2016), STAINLESS APPLIANCES (2019), WHOLE HOUSE WATER SOFTNER & DOUBLE OSMOSIS SYSTEM for DRINKING WATER, SELLER WILL CONSIDER CARPET ALLOWANCE WITH ACCEPTABLE OFFER. ****** THIS HOME IS WORTH SEEING ******

4 Beds ⋅ 3 Baths ⋅ Park Pointe Rep SubDv. ⋅ 32789 Zip Code

A MUST SEE BEAUTIFUL WELL MAINTAINED POOL HOME by ORIGINAL OWNERS in SOUGHT AFTER WINTER PARK ZIPCODE & SCHOOLS. PICTURES PROVIDE a GREAT PORTRAYAL of the FLOORPLAN but THERE ARE MANY FEATURES TO POINT OUT - THIS 2868 SQFT HOME has a 3-WAY SPLIT with 4 BEDROOMS, 3 FULL BATHROOMS, plus BONUS ROOM & OFFICE. YOU WILL NOT BELIEVE ALL THE STORAGE, STORAGE, STORAGE UNDER AIR! The BONUS ROOM (12.4 X 11.7) OFF PRIMARY BEDROOM COULD BE a NURSERY, OFFICE, EXERCISE ROOM, or OWNERS RETREAT. There is an ADDITIONAL OFFICE (13.6 X 11.6 ) with BUILT N DESK & STORAGE CABINETS MAKING a GREAT HOMESCHOOL ROOM, CRAFT AREA, or HOME OFFICE WHERE a PRIVATE EXTERIOR ENTRY DOOR is NEEDED. ONE BEDROOM could be USED as an IN-LAW SUITE with IT’S ENSUITE BATHROOM with SHOWER. The SPACIOUS GARAGE has NEW SHARK FLOORING (7/26), NEW PAINT, NEW ELECTRIC CAR CHARGING OUTLET (6/26), NEW INSULATED GARAGE DOOR & A MINI SPLIT AC – LOTS OF POSSIBILITIES! MANY FUN MEMORIES can be ENJOYED with FAMILY & FRIENDS AROUND the BEAUTIFUL SCREENED POOL & LARGE COVERED LANAI & DECK ( RESURFACED 9/25 ) The NEW OWNER of this LOVELY HOME will APPRECIATE all the UPDATES that have BEEN DONE over LAST FEW YEARS – NEW $29K LENOX UPGRADED AC (3/26), NEW FRONT DOOR (4/26), NEW GOOGLE NEST DOORBELL (3/26), NEW INSULATION in ATTIC & ON GARAGE DOOR (6/26), NEW PAVER DRIVEWAY (5/26 ) NEW UPGRADED FLASHING AROUND CHIMNEY (5/26), GAS TANKLESS WATER HEATER W RECIRCULATING FEATURE(2023), NEW DUCT WORK (2019) NEW WINDOWS (2020), WHOLE HOUSE REPLUMBED (2020), ROOF (2016), STAINLESS APPLIANCES (2019), WHOLE HOUSE WATER SOFTNER & DOUBLE OSMOSIS SYSTEM for DRINKING WATER, SELLER WILL CONSIDER CARPET ALLOWANCE WITH ACCEPTABLE OFFER. ****** THIS HOME IS WORTH SEEING ******

2667 Cochise Trail, Winter Park

$975,000

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

$925,000

Welcome to Lake Spier Crossing with NO CDD and low HOA fees, an exclusive boutique lakefront community built by Winter Park's premier builder, Meridian Homes. Nestled between the peaceful shores of Lake Spier and Lake Compton, this intimate enclave of just 10 luxury townhomes offers architecturally distinctive modern contemporary design and low maintenance living in one of Winter Park's most desirable locations. Residents enjoy private access to three community docks on Lake Spier, perfect for paddleboarding, kayaking, fishing, or simply relaxing by the water. Built in 2023, this stunning residence showcases soaring ceilings, abundant natural light, wide plank hardwood flooring, designer lighting, custom cabinetry, stone countertops, premium Café appliances, and an open concept floor plan designed for both everyday living and entertaining. Every detail was thoughtfully selected to create a timeless aesthetic, blending luxury finishes with modern functionality. Since purchasing the home, the owner has thoughtfully enhanced the property with motorized electronic shades throughout the first floor, retractable roll away screens that seamlessly extend the indoor and outdoor living experience, and a custom built Murphy bed in the guest bedroom, creating a versatile space that easily functions as both a home office and comfortable guest suite. The spacious primary suite offers a luxurious retreat, while the additional bedrooms provide flexibility for family, guests, or remote work. An upstairs laundry room and attached two car garage complete the home's thoughtfully designed layout. Step outside to enjoy your private fenced backyard with premium wrought iron fencing overlooking a peaceful, wooded lake view setting, providing both privacy and a beautiful natural backdrop. Beyond the community, you'll love the unbeatable location. Walk or bike to Downtown Baldwin Park's popular restaurants, shops, parks, and weekly events, enjoy the nearby Cady Way Trail and Lake Baldwin Dog Park, and take a short drive to Park Avenue, Rollins College, Winter Park Village, AdventHealth Winter Park, and Downtown Orlando. Combining architecturally distinctive modern contemporary design, luxury finishes, thoughtful owner upgrades, exclusive lake access, and an exceptional Winter Park location, this remarkable residence offers the perfect blend of elegance, convenience, and the lock and leave lifestyle today's buyers are searching for.

3 Beds ⋅ 4 Baths ⋅ Lake Spier Xing SubDv. ⋅ 32792 Zip Code

Welcome to Lake Spier Crossing with NO CDD and low HOA fees, an exclusive boutique lakefront community built by Winter Park's premier builder, Meridian Homes. Nestled between the peaceful shores of Lake Spier and Lake Compton, this intimate enclave of just 10 luxury townhomes offers architecturally distinctive modern contemporary design and low maintenance living in one of Winter Park's most desirable locations. Residents enjoy private access to three community docks on Lake Spier, perfect for paddleboarding, kayaking, fishing, or simply relaxing by the water. Built in 2023, this stunning residence showcases soaring ceilings, abundant natural light, wide plank hardwood flooring, designer lighting, custom cabinetry, stone countertops, premium Café appliances, and an open concept floor plan designed for both everyday living and entertaining. Every detail was thoughtfully selected to create a timeless aesthetic, blending luxury finishes with modern functionality. Since purchasing the home, the owner has thoughtfully enhanced the property with motorized electronic shades throughout the first floor, retractable roll away screens that seamlessly extend the indoor and outdoor living experience, and a custom built Murphy bed in the guest bedroom, creating a versatile space that easily functions as both a home office and comfortable guest suite. The spacious primary suite offers a luxurious retreat, while the additional bedrooms provide flexibility for family, guests, or remote work. An upstairs laundry room and attached two car garage complete the home's thoughtfully designed layout. Step outside to enjoy your private fenced backyard with premium wrought iron fencing overlooking a peaceful, wooded lake view setting, providing both privacy and a beautiful natural backdrop. Beyond the community, you'll love the unbeatable location. Walk or bike to Downtown Baldwin Park's popular restaurants, shops, parks, and weekly events, enjoy the nearby Cady Way Trail and Lake Baldwin Dog Park, and take a short drive to Park Avenue, Rollins College, Winter Park Village, AdventHealth Winter Park, and Downtown Orlando. Combining architecturally distinctive modern contemporary design, luxury finishes, thoughtful owner upgrades, exclusive lake access, and an exceptional Winter Park location, this remarkable residence offers the perfect blend of elegance, convenience, and the lock and leave lifestyle today's buyers are searching for.

1927 S Lakemont Avenue, Winter Park

Zen Home Group

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