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1562 Arbor Park Drive, Winter Park
$775,000
4 Beds ⋅ 3 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code
Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-bath residence tucked along a charming brick street in the heart of Winter Park. This move-in-ready home combines elevated finishes, abundant natural light, a flexible split-bedroom floor plan, and an exceptional location near the shopping, dining, and cultural attractions that make Winter Park one of Central Florida’s most desirable communities. At the center of the home is a completely redesigned kitchen that is both stylish and highly functional. New cabinetry, quartz countertops, stainless steel appliances, generous storage, and an oversized island with bar seating create an inviting setting for everyday meals and entertaining. A beautiful picture window frames views of the lush backyard and fills the kitchen with natural light. The open living spaces flow seamlessly together over wood-look tile flooring, while fresh interior paint, updated fixtures, and an electric fireplace add warmth and a polished contemporary feel. Privately positioned on one side of the home, the expansive primary suite feels like a retreat of its own. The suite includes a custom designed walk-in closet and a beautifully designed bathroom with separate vanities, a freestanding soaking tub, an oversized walk-in shower, and a private water closet. Three additional bedrooms are located on the opposite side of the home, providing separation and flexibility for family members or overnight guests. The outdoor setting is equally impressive. The enormous, fully fenced backyard has been lovingly maintained and features mature greenery, privacy, and plenty of room for entertaining, recreation, gardening, pets, or a future outdoor living retreat. Bonus: there is additional parking on the west side of the home that is accessible from the backyard - perfect for hosting or entertaining! A cobblestone driveway enhances the home’s curb appeal, while notable improvements include replacement of the HVAC system and ductwork in 2016, numerous plumbing updates, and extensive interior renovations. Enjoy a location that places the best of Winter Park within easy reach. The home is conveniently located near the Winter Park YMCA, Lakemont Elementary School, Phelps Park, Rollins College, and the Winter Park Chain of Lakes -  not to mention all of the boutiques, restaurants, museums, & cafés, and community events of historic Park Avenue. Baldwin Park, Winter Park Village, and Audubon Park are also just minutes away, offering even more options for dining, shopping, entertainment, and outdoor recreation. This is an exceptional opportunity to enjoy a gorgeous, fully updated home in the highly desirable in-town Winter Park address. Schedule your private showing and experience the lifestyle, location, and thoughtful design of 1562 Arbor Park Drive.

1562 Arbor Park Drive, Winter Park

2410 Sherbrooke Road, Winter Park
$769,000
4 Beds ⋅ 3 Baths ⋅ Sherbrooke SubDv. ⋅ 32792 Zip Code
Welcome to 2410 Sherbrooke Rd in Winter Park! This spacious single-story home offers 2,141 sq ft of living space with 4 bedrooms, 2.5 bathrooms, and an attached two-car garage, all in a convenient location within walking distance of Winter Park High School. 10 minutes to Full Sail University, Rollins College, or Downtown Winter Park. Step inside to find generous living and family spaces filled with natural light, beautiful hardwood flooring, and a flexible layout designed for both everyday living and entertaining. The upgraded kitchen features granite countertops, abundant wood cabinetry, stainless steel appliances, recessed lighting, a center island, and a breakfast bar overlooking the family room. The spacious primary suite features new vinyl flooring and an updated en-suite bathroom with dual vanities and a large walk-in shower. Three additional bedrooms provide plenty of flexibility for guests, home office space, or other needs. An additional full bathroom, half bath, and dedicated laundry room complete the interior. French doors lead to the screened patio, offering a comfortable space for outdoor dining and relaxing. Beyond the patio is an exceptionally large backyard surrounded by mature trees and landscaping, with plenty of room for gardening, recreation, entertaining, or creating your own outdoor retreat. Major improvements include a ROOF REPLACED IN 2022 and A/C REPLACED IN 2022, giving the next owner added peace of mind. With its upgraded kitchen and bathrooms, spacious floor plan, beautiful flooring, huge backyard, screened patio, two-car garage, and recently replaced major systems, this Winter Park home offers an outstanding combination of space, comfort, and location. Schedule your private showing today and discover everything this home has to offer!

2410 Sherbrooke Road, Winter Park

1003 Golfside Drive, Winter Park
$759,900
3 Beds ⋅ 3 Baths ⋅ Golfside Sec 02 SubDv. ⋅ 32792 Zip Code
Welcome to 1003 Golfside, a fully reimagined single-story pool home in the Winter Park area, set beneath a mature oak canopy on a beautifully landscaped lot. Major updates include a NEW ROOF (2025) and a RENOVATED POOL (2025). Inside, the open-concept layout features high-gloss marble-look porcelain tile, recessed lighting, designer ceiling fans and built-in ceiling speakers. The chef's kitchen offers high-gloss cabinetry, quartz countertops with a full-height quartz backsplash, built-in wall oven and microwave, induction cooktop and a large quartz island with bar seating. The living area showcases a custom accent wall, a brick fireplace and French doors to the pool. Bathrooms are updated with quartz vanities, vessel sinks, frameless glass showers and marble-look tile. The spacious primary bedroom offers plantation shutters and room for a sitting or office area. Outside, enjoy a private fenced backyard with the renovated pool, composite decking and an L-shaped outdoor kitchen with sink and grill. Just minutes from Baldwin Park, where you can enjoy the 2.5-mile Lake Baldwin Trail, Lake Baldwin Park with its dog beach, playground and boat ramp, the Cady Way Trail, and the Village Center's restaurants, shops and community events. Schedule your private showing today!

1003 Golfside Drive, Winter Park

8061 Pleasant Pine Circle, Winter Park
$750,000
5 Beds ⋅ 4 Baths ⋅ Enclave At Aloma SubDv. ⋅ 32792 Zip Code
Welcome to this great 5 bedroom, 3 and a half bathroom almost 3500 square foot Winter Park home! The home not only has these spaces but also is in excellent condition with; new interior paint, new carpet, 2 heating and cooling systems replaced in 2024! The open concept center island kitchen has upgraded counters, 42" cabinets and a double convection oven! Downstairs there is a formal living and dining room, an open concept kitchen, nice warm low maintenance ceramic tile, a convenient downstairs bedroom that would also be a great office/craft/game/guest room!! Upstairs are the other private bedrooms and a huge bonus theater/media/entertainment space.. The oversized primary bedroom is upstairs for complete privacy and has a well appointed bathroom as well as two walk in closets!! Come home and relax in your fenced back yard that has a peaceful forest behind it, set up a hammock and.... This fine gated community is located so close to so much, The University of Central Florida, Winter Park, Downtown Orlando, Trinity Preparatory Academy, The Masters Academy, The Geneva School, the Space Coast, Cocoa Beach and more!!

8061 Pleasant Pine Circle, Winter Park

4039 Cool Water Court, Winter Park
$739,777
4 Beds ⋅ 2 Baths ⋅ Lake Waunatta Woods SubDv. ⋅ 32792 Zip Code
Welcome to Lake Waunatta Woods, where neighbors become family. It is rare to find an exclusive, tight-knit community where neighbors look out for one another, and friendships feel more like family. This charming enclave of homes is a sanctuary of warmth, connection, and tranquility in a well-established Winter Park neighborhood. At the heart of this exceptional community is a beautifully renovated one-story residence, thoughtfully designed and built by its owners with a modern flair. From the moment you arrive, you are greeted by an elegant neutral palette, charming architectural windows and a beautifully pavered driveway leading to the stately four-pane glass front door. Step inside to soaring ceilings, art niches, elegant and an abundance of natural light that creates a warm and inviting atmosphere. To the right of the entry, the formal living room offers versatility and could easily serve as a home office, library, or additional gathering space. The heart of the home is the extraordinary chef's kitchen, beautifully appointed with custom Dovetail Gray cabinetry, oak cabinetry accented with ebony pulls, stacked white subway tile backsplash, farmhouse sink, wine cooler, state-of-the-art appliance package and a spectacular 10-foot island topped with luxurious white quartzite accented by subtle veining. This stunning kitchen flows effortlessly into the family room, creating an ideal space for everyday living and entertaining. Luxury plank flooring, neutral earth tones, and a dramatic wood-burning fireplace surrounded by natural floor-to-ceiling stone add warmth and character, while the abundance of natural light brings the beauty of the outdoors inside. The primary suite is a private retreat styled in a calming ivory palette, with wood floors, beautifully dressed windows and double doors opening directly to the poolside. The primary bath offers a distinctive custom vanity with a charming wooden treasure-chest design and a luxurious walk-in shower finished with stacked white subway tile, sitting bench and multiple shower heads for the ultimate in comfort and relaxation. Each bedroom is thoughtfully equipped with a California Closet system. Two additional generously sized bedrooms and a beautifully updated shared bath complete the one-story floor plan, offering flexibility for every lifestyle. This home has been lovingly maintained and thoughtfully refreshed, with major systems and improvements recently completed, including Andersen windows in 2024, roof in 2024, renovated baths in 2023, blown attic insulation in 2023, water heater in 2025, pool resurfacing in 2021, new salt system in 2026, and a Trane variable-speed air-conditioning system with UV light purification. The fully fenced PVC backyard provides a private setting surrounded by peaceful wooded views and beautifully landscaped grounds featuring Blue Bamboo, Foxtail trees, flower beds, and decorative river rock. Step outside to your own private backyard retreat, complete with a sparkling saltwater swimming pool and generous space for outdoor entertaining, relaxing, and enjoying the Florida lifestyle. A separate detached office/den adds exceptional versatility, featuring electricity, soundproofing and internet connectivity, making it ideal for a private home office, gym, playroom, studio, or creative space. The European-style pergola is equipped with power for lighting and a unique roof and gutter removal system and was thoughtfully designed for outdoor living space.

4039 Cool Water Court, Winter Park

1287 Verdant Glade Place, Winter Park
$735,000
4 Beds ⋅ 4 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code
Virtually Staged. Gated Community | Dual Primary Suites | Main-Level Living | Located in Winter Park’s gated Hawks Crest community, this two-story home pairs a spacious open floor plan with a private backyard setting and a layout that offers exceptional versatility. The main level includes the primary suite, dedicated study, laundry room, kitchen, and principal living areas, making day-to-day living possible without the need for stairs. The gourmet kitchen features quartz countertops and 42-inch cabinetry, while 8-foot interior doors add height and proportion throughout. Large sliding glass doors open to an oversized screened and covered patio with eastern exposure, morning sun, and no rear neighbors. Built in 2020, the home also offers the advantages of newer construction, complemented by a tile roof. Upstairs, the 4-bedroom, 3.5-bath floor plan includes three bedrooms, one serving as a second primary suite, along with a large bonus room and separate loft. Hawks Crest is set along Lake Howell and offers a clubhouse, fitness center, community pool, splash pad, parks, walking trails, grilling and picnic areas, and a pier with lake access. Park Avenue, shopping, dining, recreation, and major roadways are all within convenient reach.

1287 Verdant Glade Place, Winter Park

1316 Blue Stem Lane, Winter Park
$725,000
4 Beds ⋅ 3 Baths ⋅ Landings At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to this stunning Taylor Morrison Boca model in the highly desirable Hawks Crest gated community. This beautifully maintained 4-bedroom, 2.5-bath home offers an exceptional blend of luxury, comfort, and modern convenience. Upon entry, you're greeted by a dramatic two-story foyer with soaring 20-foot ceilings and abundant natural light. The open-concept living spaces feature luxury vinyl plank flooring throughout, plantation shutters, and corner sliding glass doors that seamlessly connect indoor and outdoor living. Enjoy breathtaking west-facing water views, a picturesque fountain and bridge backdrop, and spectacular sunset views from your private backyard. One of the home's standout features is its generously sized, aluminum-fenced backyard, offering ample space for outdoor entertaining, play, pets, gardening, or even a future pool while still enjoying tranquil waterfront views. Thoughtful smart-home upgrades include electric curtains on the sliding doors, Eufy security cameras, smart door locks, and a MyQ-enabled garage door. The oversized two-car garage also features convenient touchpad access. Residents of Hawks Crest enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, and scenic walking trails. Outdoor enthusiasts will appreciate direct access to Lake Howell for kayaking and canoeing. HOA dues include professional landscaping maintenance, allowing homeowners to enjoy a beautifully maintained property with less upkeep. This move-in-ready home offers the perfect combination of elegant design, premium upgrades, abundant outdoor space, low-maintenance living, and an unbeatable waterfront lifestyle.

1316 Blue Stem Lane, Winter Park

266 N Ranger Boulevard, Winter Park
$724,900
4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
FULLY RENOVATED Winter Park Pines Home with Mother-in-Law Suite, NO HOA & Prime Location! Welcome to this beautifully transformed Winter Park Pines residence, where modern design, thoughtful upgrades, and flexible living spaces come together in one exceptional home. Ideally located adjacent to the Cady Way Trail, with NO HOA, this property offers the lifestyle and convenience of Winter Park with the flexibility today’s buyers are looking for. Upon entering, you’re greeted by a dramatic custom charcoal accent wall with geometric detailing, creating a distinctive architectural focal point and setting the tone for the home’s contemporary design. Inside, the open and inviting floor plan features Luxury Vinyl Plank flooring throughout, recessed LED lighting, all-new interior doors, and a stylish LED fireplace that adds warmth and ambiance to the main living area. The completely renovated kitchen is designed for both everyday living and entertaining, featuring new Shaker-style cabinetry, Quartz countertops, a large center island, luxury backsplash, stainless-steel appliances, and a dedicated coffee bar with wine refrigerator. The open layout provides an ideal gathering space for family and guests. The home also features a private Mother-in-Law Suite with its own entry and outside walkway, offering exceptional flexibility for extended family, overnight guests, a home office, or a private living area. The suite includes its own beautifully renovated bathroom with a rain shower, enclosed by a ceiling-to-threshold glass pane, and an illuminated LED mirror. The primary suite bathroom has been upgraded to a luxurious, contemporary retreat, featuring a smart toilet, dual vanities, illuminated LED mirror, and an executive-style stand-up rain shower. The shower incorporates a thoughtfully designed inclined floor that directs water into a rectangular drain, along with a striking floor-to-ceiling glass enclosure, creating a clean, open, and refined feel without the need for a traditional shower curtain. Additional major improvements include a new Carrier HVAC system, tankless water heater, updated double-pane windows, complete re-plumbing, re-wiring with an updated electrical panel, and a new roof installed 7/17/2023. Step outside and enjoy the home’s inviting outdoor spaces, including a covered front porch with dusk lighting, screened rear porch, spacious backyard, and oversized driveway. A series of cement slab walkways, separated by polished, large river stones, leads from the garage to the front door, with matching paths continuing along the rear of the home. Solar security lighting and decorative LED lighting add both functionality and evening ambiance. Ideally situated in Winter Park Pines and directly adjacent to the Cady Way Trail, the home offers convenient access to major roadways, hospitals, golf courses, colleges, shopping, dining, and highly regarded private schools—all within a short drive. With an extensive renovation, three beautifully updated bathrooms, a private Mother-in-Law Suite, modern kitchen, tankless water heater, new roof, updated electrical and plumbing, NO HOA, and an outstanding Winter Park location, this home offers a rare combination of style, functionality, and convenience. Come experience the renovation, thoughtful details, and flexible floor plan in person. Schedule your private showing today!

266 N Ranger Boulevard, Winter Park

1884 Jessica Court, Winter Park
$699,900
3 Beds ⋅ 2 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code
Enjoy bright, inviting living and your own screened pool retreat in Winter Park! This 3-bedroom, 2-bath home offers 1,666 square feet with vaulted ceilings, abundant natural light, and plantation shutters. The spacious family room features laminate flooring and a wood-burning fireplace, creating a welcoming place to gather. The updated kitchen offers stainless steel appliances, ample drawer storage, a pullout pantry, and a sunny dinette with sliding doors to the outdoor living area. Multiple access points throughout the home connect to the screened pool enclosure, where a recently resurfaced pool and covered patio provide space for relaxing and entertaining. The primary suite features a walk-in closet and an en-suite bath with dual sinks and a separate shower. Two additional bedrooms offer flexibility for guests or a home office, while the second full bath includes a bathtub. An attached two-car garage provides laundry space, extensive cabinetry, and pull-down attic access. All appliances are included, adding convenience to this inviting Winter Park home.

1884 Jessica Court, Winter Park

1418 Lone Feather Trail, Winter Park
$699,500
4 Beds ⋅ 3 Baths ⋅ Landings At Hawks Crest SubDv. ⋅ 32792 Zip Code
Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,000 in luxurious builder upgrades, blending timeless design, modern comfort, and effortless Florida Living. This stunning home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes and a thoughtfully designed open-concept floor plan create a seamless flow throughout the home. Luxurious white ceramic tile spans the entire first floor, enhancing the home's bright and airy feel while providing both beauty and durability. The gourmet kitchen serves as the centerpiece of the home, featuring upgraded cabinetry, quartz countertops, stainless steel appliances, abundant storage and an expansive peninsula with bar seating. Spacious living areas and generously sized bedrooms provide comfort and flexibility for a variety of lifestyles. Upstairs, plush carpeting creates a warm and inviting retreat, while the primary suite offers a private sanctuary complete with a large walk-in closet and a spa-inspired bath. Additional bedrooms provide ample space for family, guests, a home office or a fitness room. Sliding glass doors extend the living space to a covered lanai, creating an inviting setting for outdoor dining, morning coffee or relaxed evenings enjoying Florida's year-round climate. Residents of Hawks Crest enjoy an exceptional collection of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, playgrounds, dog park, scenic trails and private access to Lake Howell. The community is also conveniently located near local favorites, including Kelly's Ice Cream, Foxtail Coffee and Park Maitland Preschool. Ideally situated just minutes from Park Avenue, downtown Maitland, major highways, and top-rated schools, this exceptional home offers effortless access to Central Florida's finest shopping, dining and cultural attractions. Despite its convenient location, the community maintains a sense of privacy and tranquility.

1418 Lone Feather Trail, Winter Park

1850 Bryan Avenue, Winter Park
$699,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code
Tucked beneath mature oak trees, 1850 Bryan Avenue is a well-maintained home offering comfortable single-story living in Winter Park. Natural light and warm wood floors flow through the inviting living and dining spaces, while a flexible bonus room is well suited for a home office, den or creative space. The kitchen features wood cabinetry and ample counter space. The spacious primary suite offers a private retreat. Additional features include an indoor laundry room and an attached two-car garage. Outside, the fenced yard provides a peaceful setting for gardening, entertaining or relaxing beneath the trees. With shopping, dining, parks and other Winter Park amenities nearby, this home brings together character, comfort and a desirable location.

1850 Bryan Avenue, Winter Park

715 S Ranger Boulevard, Winter Park
$695,000
4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Welcome to your dream home in the highly sought-after community of Winter Park Pines! This beautifully maintained 4-bedroom, 3-bathroom residence offers 2,312 square feet of comfortable and stylish living space ideally designed for modern and multigenerational lifestyles. The recently remodeled primary suite is a true retreat, featuring new carpeting and tile flooring, dual granite vanities, an oversized walk-in shower with modern, upgraded fixtures, a new water closet, and thoughtful contemporary finishes throughout. Inside, you’ll find timeless architectural charm which includes a formal dining room, three spacious living areas, louvered window shutters, and elegant hardwood flooring. One of the living spaces is highlighted by a stunning brick fireplace overlooking the beautiful private pool area and fully fenced backyard — creating the perfect setting for entertaining, family gatherings, or simply unwinding in your own backyard oasis. In addition, this spectacular residence also boasts tasteful landscaping touches for exceptional curb appeal, a large two-car garage with electric opener, a newer shingle roof replaced in late 2023, and fresh interior paint throughout the home. Ideally located near Winter Park Pines Golf Club, Cady Way Trail, Ward Park, Showalter Field, tennis and pickleball courts, top-rated schools, and the many shopping and dining destinations of Park Avenue and historic downtown Winter Park. Don’t miss this rare opportunity to own a true Winter Park gem — schedule your private showing today!

715 S Ranger Boulevard, Winter Park

2260 Coldstream Drive, Winter Park
$675,000
4 Beds ⋅ 2 Baths ⋅ Brookshire Heights SubDv. ⋅ 32792 Zip Code
Virtually Staged. Zoned for Fantastic Winter Park Schools, this 4 bed, 2 bath recently renovated abode is waiting for you. Located on a quiet, tree-lined street, you can walk to highly rated Brookshire Elem and Winter Park High. The open-plan living space has beautiful travertine tile floors flowing through the kitchen, dining room, and living room. Renovated in 2026, the kitchen offers quartz counter tops, new appliances, under cabinet lighting, custom tile backsplash, and pendant lights. Flowing from the kitchen to the dining room and through to the living room, this open floor plan is sure to please. Double French doors open from the sunny living room to the spacious backyard. The oversized two-car garage and laundry room are just off the kitchen. Travertine continues down the hall, while all 4 bedrooms have newly installed wood flooring (2024). The primary bedroom has a renovated ensuite (2026) with enlarged walk-in shower, custom tile, new fixtures, and new quartz topped vanity. All 4 bedrooms have window shutters and new ceiling fans, and the renovated hall bath (2025) offers new quartz topped double sink vanity, new mirrors, and tub/shower tile surround. Out back, the grassy backyard with new fencing and St Augustine sod (2025) offers plenty of room for kids and pets to play or even a future pool addition. Located just 3 miles to Rollins College and the Park Ave shopping and dining district, this prime location offers other, even closer, benefits. Cady Way Park is 2 blocks away with a community pool, pickleball courts, tennis courts, picnic tables, and access to the Cady Way Bike Trail. NEW HVAC 2024, Roof 2015, updated electrical box 2014, and house re-piped with CPVC 2009. Come check out this charming move-in ready Winter Park house and make it your own home.

2260 Coldstream Drive, Winter Park

1122 Wildmeadow Run, Winter Park
$660,000
4 Beds ⋅ 3 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to a premier opportunity in the the coveted Winter Park. This beautifully maintained 4-bedroom, 2.5-bathroom home is located in The Meadows – an alcove in the gated Hawks Crest community – and offers buyers a turn-key opportunity to crack into the Winter Park market. With 1,770 square feet of thoughtfully designed living space, this home strikes the perfect balance between functionality and flow, featuring a living/dining combination anchored by the kitchen in the heart of the home. The central dining configuration is equally suited for quiet evenings or effortless entertaining, while the living room offers versatility as a spacious indoor retreat, or an indoor-outdoor oasis, complimented by the glass sliders. Before entering the primary suite, find three secondary rooms - two guest bedrooms and an office - along with a full guest bathroom and a powder bath, making every day living hassle-free and providing ample privacy. In the primary en-suite, unwind and enjoy the pleasures of a spacious retreat featuring an over-sized walk-in shower. This home is only 4 years young, so newer appliances and core components provide peace of mind, and an upgraded Tesla level 2 charger makes it fully equipped to suit every homeowner's needs. This home is just a short walk to the community amenities which include a clubhouse, pool, fitness center, turf lawn with a putting green, playground, dog park, and a private community dock on to Lake Howell. The 24-hour gated community provides peace of mind, all within easy reach of A-rated Seminole County schools (Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High), major employment corridors, the Orlando International Airport, and everything that Orlando has to offer. This is the kind of opportunity that doesn't come along often. Contact us to schedule your private tour today!

1122 Wildmeadow Run, Winter Park

900 Carver Street, Winter Park
$659,000
3 Beds ⋅ 3 Baths ⋅ Magnolia Gardens Sub SubDv. ⋅ 32789 Zip Code
Completely Renovated | Move-In Ready | Single-Story Living. A comprehensive renovation brings modern finishes and functionality to this Winter Park home, with a redesigned kitchen that opens to the main living area. The kitchen features 42-inch shaker cabinetry, Calacatta quartz countertops, stainless steel appliances, a center island, and pantry storage. Luxury vinyl flooring extends through the main living areas, complemented by recessed LED lighting and updated fixtures. A complete interior renovation and landscaping updates were completed in 2026, complementing major improvements from 2019, including a new roof, HVAC system, and double-pane windows. The three-bedroom, three-bathroom layout includes two spacious en-suite bedrooms, with all bathrooms completely remodeled. Additional features include an interior laundry closet and a fully fenced backyard. Outside, paver walkways, manicured lawns, and refreshed landscaping complement the home's updated exterior. Located in Magnolia Gardens with no HOA, the property offers convenient access to Park Avenue's restaurants, boutiques, and farmers market, as well as Lake Lily, Maitland City Centre, and I-4.

900 Carver Street, Winter Park

5303 Pine Lily Circle, Winter Park
$654,000
3 Beds ⋅ 2 Baths ⋅ Sanctuary At Aloma SubDv. ⋅ 32792 Zip Code
POOL HOME IN WINTER PARK! Beautifully maintained 2015-built one-story in the quiet, gated community of Sanctuary at Aloma, offering 2,265 sq ft with 3 spacious bedrooms, a dedicated den/flex/home office, and a separate formal dining room, all on one level with no stairs. The open-concept great room flows into a light-filled kitchen featuring a large center island, stone countertops, a sleek backsplash, and abundant cabinetry, perfect for entertaining. The private primary suite is a true retreat with a separate soaking tub and shower plus plenty of storage. Secondary bedrooms are well sized with great closet space. Step outside to your screen-enclosed in-ground pool, added in 2020, with a covered sitting area and a fully fenced, beautifully landscaped backyard, privacy rarely found at this price point. Additional features include tile and laminate flooring, an owned security system, an attached 2-car garage, public water and sewer, and excellent curb appeal with stucco exterior and carriage-style garage door. Low quarterly HOA and NO CDD. Minutes from SR-417 at Aloma Ave, placing UCF, Research Park, Oviedo, and downtown Orlando within an easy commute. Close to Winter Park Village, historic Park Avenue, Full Sail, Rollins College, and Orlando International Airport. All information deemed reliable but not guaranteed; buyer and buyer's agent to verify all measurements and features. Schedule your private showing today!

5303 Pine Lily Circle, Winter Park

2322 Woodcrest Drive, Winter Park
$650,000
4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code
Set on a quiet, landscaped, quarter-acre lot, this 4-bedroom, 2-bath POOL HOME offers a rare combination of privacy, space and neighborhood charm - all within the Kenilworth Shores neighborhood of Winter Park. Step inside to find an open and inviting great room filled with natural light and framed by sliding doors overlooking the pool and backyard. At the center of the home, the fully remodeled kitchen features shaker-style cabinetry with a built-in pantry, granite countertops, stainless steel appliances and a large breakfast bar with plenty of space for casual dining and entertaining. Step outside to the screened porch and pool, creating a wonderful extension of the living space for year-round Florida living. The landscaped yard includes an irrigation system and plenty of outdoor space. The primary suite features a walk-in closet and fully updated ensuite bathroom showcasing a beautiful granite topped vanity, updated fixtures and new shower. The renovated hall bath features a granite topped vanity with dual sinks, tile and fixtures. Major updates include a BRAND NEW HVAC system installed in 2026, NEWER ROOF and water heater, insulated DOUBLE PANE WINDOWS, and a new septic drainage field in 2024. The oversized two-car garage and large driveway provide plenty of parking and storage. The location puts you close to so much of what makes Winter Park desirable. WINTER PARK HIGH SCHOOL is within walking distance, with Brookshire Elementary and Glenridge Middle also nearby. Park Avenue is a 10 minute drive, while Baldwin Park and the Lake Baldwin trail and dog park are a five minute walk from the home. Enjoy easy access to Full Sail University, UCF, Valencia College, major transportation routes and Orlando International Airport. With its extensive updates, private pool and convenient Winter Park location, this home is truly move-in ready—schedule your private showing today and come see everything 2322 Woodcrest Drive has to offer!

2322 Woodcrest Drive, Winter Park

518 Gilbert Road, Winter Park
$649,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Welcome to 518 Gilbert Road, a beautifully updated 3-bedroom, 2-bath pool home offering 1,573 square feet of single-story living in the desirable Winter Park Pines neighborhood - with no HOA. Freshly installed front yard sod and mulch, mature palms, and distinctive stone accents create an inviting first impression. Inside, the home is light and bright with original terrazzo flooring and spacious living and dining areas. The living room features a wood-burning fireplace and architectural ceiling detail that adds character to the space. The beautifully updated kitchen offers white cabinetry, granite countertops, stainless steel appliances, a gas cooktop, convection oven, subway tile backsplash, modern lighting, and a large peninsula with bar seating. Both bathrooms have been renovated, including the primary bath with a walk-in shower and an updated guest/pool bath with convenient direct access to the backyard. Step outside to a private screened pool and an expansive pool deck, recently resurfaced in May 2026, providing plenty of room for outdoor dining, entertaining, and relaxing. Fully paid solar pool-heating panels extend the enjoyment of the pool, while the fully fenced PVC backyard adds privacy. A spacious two-car garage and outdoor storage provide additional room for everyday needs. Additional improvements include updated windows and sliding doors, replumbing, a newer HVAC system with gas/propane furnace, gas line, and partial updated ductwork. Enjoy an exceptional Winter Park location close to Cady Way Trail, Winter Park Pines Golf Club, Cady Way Park and its recreational amenities, Baldwin Park, and Downtown Winter Park. AdventHealth Winter Park, Rollins College, Full Sail University, UCF, shopping, dining, and everyday conveniences are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School, this move-in-ready pool home combines classic Winter Park character, thoughtful updates, and an outstanding location.

518 Gilbert Road, Winter Park

2215 Woodcrest Drive, Winter Park
$637,500
4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code
PRICE JUST REDUCED!! Nestled on a tranquil, tree-lined street in the vibrant heart of Winter Park, this reimagined 1960s mid-century modern pool residence beautifully harmonizes timeless architectural soul with stylized contemporary updates. Bathed in glorious natural sunlight, the open-concept interior unfolds beneath soaring vaulted ceilings, where durable wood-look flooring flows seamlessly across expansive living and dining spaces. At the center of it all lies a true chef’s haven—an exquisitely updated kitchen equipped with solid wood cabinetry, rich granite countertops, a sprawling prep island, sleek stainless steel appliances, and a bold over-range hood. Thoughtfully arranged along a private bedroom wing, the four spacious bedrooms blend exceptional comfort with versatile living spaces. The fourth bedroom is framed by views of the sun-drenched pool deck—an inspiring backdrop for a home office, creative sanctuary, or private gym. The primary retreat serves as a peaceful haven, complete with an elegant ensuite bath showcasing custom tile work and a glowing vanity mirror. Step through the doors into your own fully fenced tropical oasis, where quintessential Florida living takes center stage. Spend your afternoons lounging beside the sparkling swimming pool, entertaining guests from the custom Tiki bar, or relaxing with a cool drink under the shade of the gazebo surrounded by fresh, plush, mature landscaping and fresh sod. Modern convenience and major infrastructure upgrades ensure total peace of mind, featuring updated plumbing, electrical, and windows, along with a brand-new 2026 HVAC heat pump system (complete with a 10-year warranty) and a 2026 water heater. Complete with a two-car carport, dual storage rooms, indoor laundry, and a well-water irrigation system, every practical detail has been addressed. All of this is situated within top-tier school zones (Brookshire, Glenridge, and Winter Park High), just moments from the boutique shopping and dining on Park Avenue, Rollins College, Baldwin Park, Cady Way Trail, medical hubs, and the energy of downtown Orlando. Don't miss out on one of the lowest priced homes in Winter Park School district!!

2215 Woodcrest Drive, Winter Park

2758 Banchory Road, Winter Park
$619,500
3 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
FULLY PAID SOLAR PANELS INCLUDED — NO SOLAR LOAN TO ASSUME! A rare added value for the next owner: enjoy the benefits of solar energy with the system included in the sale and no remaining solar panel balance. Welcome to 2758 Banchory Rd, a beautifully maintained 3-bedroom, 2-bath pool home in desirable Winter Park Pines. This charming ranch-style home offers a bright open layout, mature landscaping, a fully fenced backyard, private swimming pool, covered outdoor living space, storage shed, and no HOA. Located just steps from the Cady Way Trail and minutes from Cady Way Park, Winter Pines Golf Club, Baldwin Park, AdventHealth Winter Park, Full Sail University, Downtown Winter Park and Park Avenue. Enjoy the privacy of a quiet street with convenient access to shopping, dining, recreation and major roadways. PRIVATE POOL + PAID-OFF SOLAR + NO HOA + PRIME WINTER PARK LOCATION. An exceptional combination of lifestyle, location and long-term value. Schedule your private showing today.

2758 Banchory Road, Winter Park

508 Brechin Drive, Winter Park
$599,000
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code
Renovated and move-in ready, this updated Winter Park home offers a fresh, modern interior without the hassle of renovations. The brand-new kitchen features new cabinetry, quartz countertops and all new appliances, while both bathrooms have been fully renovated with new finishes and fixtures. New luxury vinyl plank flooring runs throughout the home, complemented by fresh interior paint. The roof was replaced in April 2022, providing added peace of mind for today's buyer. With 3 bedrooms, 2 bathrooms and approximately 1,785 square feet of living space, this home offers a comfortable and functional floor plan in an established Winter Park location. The spacious yard offers plenty of room for outdoor enjoyment and the opportunity to create your own ideal landscaping. Enjoy easy access to Cady Way Park and the Cady Way Trail, perfect for walking, biking and recreation. Just minutes from the restaurants, shopping and charm of Park Avenue, as well as the popular Baldwin Park area. Conveniently located near AdventHealth Winter Park and numerous dining, shopping and recreational options. Agent owned property.

508 Brechin Drive, Winter Park

4026 Tenita Drive, Winter Park
$599,000
3 Beds ⋅ 2 Baths ⋅ Lake Waunatta Wods SubDv. ⋅ 32792 Zip Code
MOVE IN READY! New roof, new bathrooms, new kitchen, new floors, new electrical panels and more. Located in the beautiful lake community of Lake Waunatta Woods. Large private lot on greenbelt. 3 bedroom, 2 bath POOL home with 2 masters and split floor plan. The second master has outside entrance for option to use as a mother-in-law suite or rental. Spacious living room/dining room, family room, laundry room and 2 car garage. Beautiful pool area with screened porch and two patios. Just minutes to UCF and Full Sail University. Easy access to 417 and 15 minutes to downtown Winter Park, walk to Publix and Target. Fast closing available. Don't miss this gem, pack your bags and live life in this mini retreat that you will call home!

4026 Tenita Drive, Winter Park

4260 Bear Gully Road, Winter Park
$585,000
4 Beds ⋅ 4 Baths ⋅ Bear Gully Forest SubDv. ⋅ 32792 Zip Code
RENOVATED 4 BED / 3.5 BATH ON AN OVERSIZED 0.57-ACRE LOT | GOURMET KITCHEN | SCREENED LANAI | FENCED YARD | ROOF 2018 | FLOOD ZONE X | LOW HOA. Welcome to 4260 Bear Gully Road, a move-in-ready two-story home on nearly 25,000 sq ft of land, with space for a pool, garden or play area (buyer to verify). The gourmet kitchen was fully remodeled two years ago with upscale cabinetry and modern appliances, and luxury vinyl flooring gives the home a clean, low-maintenance look. The primary suite is on the first floor with a walk-in closet, and four bedrooms and three and a half baths give everyone room for family, guests or a home office. Ceiling fans, a two-car garage with opener, and concrete block and stucco construction add comfort and peace of mind. Relax on the screened lanai overlooking the large fenced backyard. Near Publix-anchored shopping and dining on Aloma Avenue, AdventHealth Winter Park, the Cross Seminole Trail and SR 417, with Winter Park Village and Park Avenue a short drive away. Seminole County schools: Eastbrook Elementary, Tuskawilla Middle and Lake Howell High (buyer to verify). Schedule your showing today!

4260 Bear Gully Road, Winter Park

1399 Aloma Avenue, Winter Park
$575,000
3 Beds ⋅ 2 Baths ⋅ Galloway Place Rep SubDv. ⋅ 32789 Zip Code
Charming 1948 home with Winter Park Chain of Lakes access offers a great opportunity for buyers looking to renovate or explore new construction in an established Winter Park location. Conveniently located near Rollins College, Park Avenue, and Winter Park Hospital, with access to Lake Osceola just a short walk away to launch a paddleboard or canoe. The 3-bedroom, 2-bath character home offers a split floor plan with original hardwood floors, arched doorways, plantation shutters, and a formal living room with a gas fireplace and built-ins. The updated kitchen features Carrara quartz countertops, stainless appliances, and wood cabinetry, and opens to the dining and sunrooms. French doors from the sunroom lead to a covered patio and backyard with mature landscaping, paver walkways, and a tranquil cabana perfect for relaxing. Additional features include an attached one-car garage with washer/dryer, walk-in closets, and a circular driveway for additional parking. Improvements include new PEX water supply lines (2025) and partial drain-line replacement, recent interior painting, and updated bathrooms with a 2019 renovation featuring marble shower and floors. With its original character, thoughtful improvements, and convenient Winter Park location, this home offers an opportunity for its next owner to make it their own.

1399 Aloma Avenue, Winter Park

2228 King Charles Court, Winter Park
$575,000
4 Beds ⋅ 3 Baths ⋅ Winter Woods Unit 03 SubDv. ⋅ 32792 Zip Code
Virtually Staged. PRICED TO SELL, 25K UNDER APPRAISED VALUE!! Come check out this GORGEOUS, SOLID 4/5 BR, 3 BA, 2,500+ sqft home in Winter Park with everything you need. This exceptional concrete block home was built to last, and major systems are current, updated, and documented. This home is MOVE-IN READY! Step inside and you’ll FEEL the difference. Fresh, neutral paint throughout and new vinyl flooring in both living areas create a light, welcoming backdrop. The kitchen, remodeled in 2023, shines with gleaming quartz counters, backsplash, shaker cabinets, and a breakfast bar. Upstairs, the HUGE master bedroom features a fireplace and balcony overlooking a large backyard—your personal private retreat! The bottom level offers GREAT flexibility—configure it as an IN-LAW SUITE with its own private bath and patio with French doors, or as a second living room and Florida room. Out back is where you’ll actually WANT to spend time with family and friends! Enjoy a naturally shaded deck every morning and evening. The oversized garage has a FAST EV charger. The property also comes with a large storage building with electricity AND a smaller shed. Major systems and structural upgrades include: HURRICANE-RATED double-pane windows and exterior doors opening to 4 feet! (2024), full home replumb (PEX-A), roof (5 years), electrical brought to current code (2025), water heater (2025), attic insulation with SOLAR FAN and sealed opening, and a high-efficiency Lennox AC (5-ton, 16 SEER) maintained yearly. Energy monitoring system included. Located in Seminole County’s top-rated school district, it is 15 minutes from Full Sail, 20 minutes from Rollins, and 30 minutes to UCF. This is the home that checks off all the boxes! MOTIVATED SELLER!!

2228 King Charles Court, Winter Park

112 Bell Place, Winter Park
$575,000
3 Beds ⋅ 2 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code
Welcome to 112 Bell Place, a spacious 3-bedroom, 2-bath home offering 2,253 square feet in an established Winter Park neighborhood. Tucked away on a quiet cul-de-sac with a large lot and minimal through traffic, this home offers a great opportunity for buyers looking to move right in and make updates over time, or for an investor looking for a property with great bones and plenty of potential. Inside, you’ll find generous living spaces including a living room with laminate wood flooring and vaulted ceiling, plus a large family room featuring a brick accent wall. The kitchen offers solid wood cabinetry, cooktop, oven and microwave with plenty of opportunity to update and make it your own. All three bedrooms feature built-in closets, while the primary suite includes wood-look laminate flooring and a private bath with shower. The guest bath offers a tub and tile flooring. Additional features include a one-car garage, exterior laundry area, and a hall closet already plumbed for a washer and dryer should the new owner prefer to bring the laundry indoors. With its spacious floor plan, large lot and solid foundation for future improvements, this home has so much potential. Conveniently located in Winter Park and currently zoned for Lakemont Elementary, Maitland Middle and Winter Park High School, this is a great opportunity to get into a sought-after area and add your own style over time. Move in now, renovate at your own pace, and make this Winter Park home your own! Buyer to independently verify school zoning.

112 Bell Place, Winter Park

2141 Lake Drive, Winter Park
$569,900
3 Beds ⋅ 2 Baths ⋅ Killarney Point SubDv. ⋅ 32789 Zip Code
Rare opportunity in Winter Park’s highly desirable 32789 ZIP code! Situated on Lake Drive directly across from Lake Killarney, this 3-bedroom, 2-bath pool home sits on an expansive .33-acre lot surrounded by multi-million-dollar lakefront residences and impressive new luxury construction. Offering 1,824 square feet of living space, the home is move-in ready with distinctive architectural character, vaulted wood ceilings, a wood-burning fireplace, and inviting living areas. Step outside to a private swimming pool and spacious backyard with exceptional room to enjoy Florida living. The true value lies in the possibilities: enjoy the home as it is, renovate, expand, or build a custom luxury residence exceeding 5,000 square feet. With potential views of Lake Killarney and significant new construction transforming the surrounding neighborhood, this property offers a compelling combination of location, lot size, and long-term potential. Live in it, reimagine it, or build your dream home in one of Winter Park's most sought-after areas!

2141 Lake Drive, Winter Park

257 Lincolnshire Road, Winter Park
$550,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Welcome to 257 Lincolnshire Road, a 3-bedroom, 2-bath home offering 1,610 square feet of living space in the established Winter Park Pines neighborhood. Situated at the end of a cul-de-sac street, this single-story home sits on an expansive 0.58-acre lot, providing an inviting setting with room to bring your vision to life. Inside, a spacious living and dining layout features multiple gathering areas, large windows that welcome natural light, and a distinctive brick fireplace with wood-paneled detailing. The kitchen offers generous cabinet storage, a breakfast bar, and an open connection to the main living area. An attached two-car garage adds everyday convenience. Sliding glass doors open to a covered, screened-in patio overlooking the oversized backyard. With over 200 feet of rear property line, this expansive outdoor space offers remarkable flexibility for entertaining, gardening, recreation, or designing your own outdoor retreat. Mature trees and natural greenery create a welcoming backdrop with plenty of room to enjoy. Whether you envision renovating and personalizing the existing home or starting fresh by removing the current structure and building a new residence, this expansive property offers the flexibility to explore a variety of possibilities. Enjoy the appeal of an established neighborhood with the golf course just down the street and convenient access to Aloma Avenue. With its generous lot, cul-de-sac setting, and Winter Park location, this property is ready for your ideas.

257 Lincolnshire Road, Winter Park

7525 Lodge Pole Trail, Winter Park
$550,000
4 Beds ⋅ 2 Baths ⋅ Arrowhead Cove SubDv. ⋅ 32792 Zip Code
WOW! Now offered at $25,000 less, this fully renovated Winter Park POOL home pairs move-in-ready style with an expansive .36-acre lot! With FOUR bedrooms, TWO updated bathrooms and nearly 2,000 square feet, you’ll enjoy a beautifully renovated kitchen, a split floor plan and a screened lanai overlooking your private pool—all ready for your next chapter in the established Arrowhead Cove Neighborhood!This home was thoughtfully renovated throughout, this move-in-ready residence combines modern finishes, an ideal SPLIT FLOOR PLAN and exceptional outdoor living with a location zoned for top-rated Winter Park schools. Inside, ALL brand-NEW WINDOWS AND SLIDERS, installed in 2026, fill the home with natural light while wood laminate flooring, fresh interior paint, and recessed lighting create a polished, comfortable atmosphere. The RENOVATED 2025 KITCHEN features crisp white shaker-style cabinetry, quartz countertops, brand-new stainless steel appliances and a spacious stainless sink, creating a stylish and functional centerpiece for everyday living and entertaining. The private primary suite is thoughtfully separated from the secondary bedrooms and offers dual built-in closets and a FULLY RENOVATED ensuite BATHROOM with a double quartz vanity, beautifully tiled shower and separate water closet. Three additional bedrooms share a FULLY RENOVATED hall bathroom featuring a double quartz vanity, tiled tub/shower and convenient direct access to the pool area. Step outside to your own private backyard retreat, where a spacious screened LANAI overlooks the sparkling in-ground POOL. Resurfaced in 2025, the chlorine-generated pool also features a NEW PUMP, LIGHT, steps and filter. A separate GAZEBO provides another inviting space for outdoor dining or relaxing, while the FULLY FENCED oversized .36-acre pie-shaped lot offers plenty of room to enjoy the outdoors. A TWO-CAR garage adds everyday convenience and storage. Ideally located just FIVE minutes from Full Sail University and SR 417, approximately 15 minutes to UCF and 20 minutes to Orlando International Airport, this exceptional home also offers easy access to Target, Costco, grocery stores and abundant retail. Only 15 minutes from Downtown Winter Park luxury dining and shopping. With extensive 2025-2026 renovations, a private pool and an oversized lot in a highly desirable Winter Park school zone, this is a rare opportunity to enjoy turnkey living in a prime Central Florida location. ROOF - 2023 HVAC - 2018 PLUMBING - 2025 WATER HEATER - 2017

7525 Lodge Pole Trail, Winter Park

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