Winter Garden/Oakland Homes for Sale

Built by RCB Custom Homes as the builder’s personal residence, this exceptional 5-bedroom, 5-bath residence offers 3,506 square feet of thoughtfully designed luxury in the highly desirable Oakland Park neighborhood. Completely remodeled within the past two years, no detail was overlooked in creating a home that is as refined as it is comfortable. Beautiful new hardwood flooring, custom wood beams, designer wallpaper, upscale tile selections, custom cabinetry, premium appliances, and an antique barn wood fireplace treatment create distinctive character throughout. Custom automated blinds and a complete repaint add the finishing touches to this beautifully curated home. Designed for both everyday living and entertaining, the home features inviting screened front and side porches, with an outdoor kitchen. The premium lot faces a long green park with views of Lake Apopka, adjacent to the community clubhouse & amenities . Beyond the beautiful finishes are the exceptional behind-the-scenes upgrades that truly set this home apart, including a whole-home generator, spray foam insulation for impressive energy efficiency, an expansive climate-controlled attic offering valuable conditioned storage, and wiring in place for a future water treatment system. Enjoy all that Oakland Park has to offer, including two community pools and a prime location within the golf cart district. A complete list of upgrades and improvements is available upon request. This is a rare opportunity to own a meticulously remodeled custom residence where luxury, craftsmanship, comfort, and thoughtful design come together.

1032 Galston Alley, Winter Garden

$530,000

3 Beds ⋅ 3 Baths ⋅ O6443711 MLS

PRIME WINTER GARDEN LOCATION! Skip the builder delays with this move-in-ready Horizon West bungalow nestled in Silverleaf Reserve, delivering 3 bedrooms, 2.5 bathrooms, and a bright second-floor flex loft. Designed for effortless everyday living, the ground level centers around a sun-drenched, open great room paired with a quartz-island kitchen, dedicated pantry, powder bath, and a direct-entry garage that takes the hassle out of grocery runs. Up top, find a secluded primary retreat complete with private bath and walk-in wardrobe, accompanied by two guest rooms, an additional full bath, and an adaptable loft tailored for remote work or movie nights. Beyond the covered porch and neighborhood pool, the standout draw is pure convenience: Hamlin Elementary and Hamlin Middle sit right across the street for a zero-traffic morning walk, while Hamlin Town Center retail, dining, the 429 expressway, and Disney remain minutes away. Vacant and seamless to show—book your tour today!

4958 Citrus Leaf Blvd, Winter Garden

$899,000

4 Beds ⋅ 4 Baths ⋅ O6441782 MLS

Welcome to this beautiful two-story single-family home located in the desirable Winter Garden area. Featuring 4 bedrooms and 3.5 bathrooms, this residence combines generous living spaces with a comfortable and functional floor plan designed for everyday living and entertaining. The well-planned layout creates a natural flow throughout the home, with spacious living areas that provide plenty of room to relax, gather, and enjoy time with family and guests. The two-story design provides excellent separation between common living spaces and private areas, creating both convenience and privacy. Generously sized bedrooms provide flexibility for a variety of needs, including guest accommodations, a home office, or additional living space. With 3.5 bathrooms, the home provides added convenience for residents and visitors alike. Located in Winter Garden, this property enjoys convenient access to shopping, restaurants, entertainment, major roadways, and the many recreational destinations throughout Central Florida. The location provides easy connectivity to surrounding communities while maintaining the residential atmosphere that makes Winter Garden such a sought-after area. With its spacious layout, four-bedroom configuration, and desirable location, this home is a wonderful opportunity for those looking for comfort, functionality, and convenience in Winter Garden. Schedule your private showing today and experience everything this residence has to enjoy.

14961 Lebeau Loop, Winter Garden

$700,000

3 Beds ⋅ 2 Baths ⋅ O6443368 MLS

Every single day, you’ll experience the ultimate Central Florida lifestyle in your own private backyard paradise. Tucked into the coveted Latham Park community of Winter Garden, just two miles from Disney’s Magic Kingdom, this pristine 2018-built home pairs luxurious outdoor living with unbeatable convenience to world-class entertainment, shopping, and dining. Surrounded by updated curb appeal, mature landscaping, and a quiet neighborhood setting, it offers a rare combination of comfort, style, and resort-style amenities right at home. Inside, the light-filled floor plan feels crisp, elevated, and completely turn-key, highlighted by elegant crown molding and durable wood-look tile floors running throughout the main living areas. High tray ceilings accentuate the main open-concept living and dining spaces, leading seamlessly into a dedicated flex space. Showcasing true Florida indoor-outdoor living, the home features both a standard sliding door and a triple sliding glass door that opens directly from the flex space out to the pool area. At the center of it all is a modern chef’s kitchen designed for both quiet mornings and hosting friends. It boasts 42-inch cabinets, sleek quartz countertops, under-cabinet accent lighting, a gas range, and premium stainless steel appliances. Conveniently nearby, an oversized laundry room comes fully equipped with a washer and dryer while providing exceptional extra storage space. For total peace of mind and remarkable efficiency, the home is secured with a SimpliSafe security system, equipped with a tankless water heater, and features fully paid-off solar panels for ultra-low electricity bills. The primary suite serves as your private sanctuary, featuring a custom built-in walk-in closet system and a beautifully appointed primary bathroom complete with a luxurious, walk-in shower. Two additional spacious bedrooms with luxury vinyl flooring provide exceptional flexibility for family, guests, or a dedicated home office setup. Step out back into your personal outdoor oasis—a custom screen-enclosed pool deck featuring a stunning heated saltwater pool and spa, built-in controllable LED lighting overhead and within the enclosure, and a Char-Broil outdoor kitchen perfect for weekend barbecues. The fully fenced backyard ensures a private, safe space for relaxation or outdoor fun. Beyond your doorstep, enjoy Latham Park’s vibrant community events, pool, playground, and spectacular views of the Disney fireworks right from within the neighborhood—plus access to top-tier schools including Panther Lake Elementary, Hamlin Middle, Horizon High, and Windermere Prep. From private poolside relaxation to nightly magic nearby, this is a rare gem in one of Winter Garden’s most sought-after pockets.

14371 Shocklach Drive, Winter Garden

$515,000

3 Beds ⋅ 3 Baths ⋅ S5158021 MLS

Welcome home to this beautifully maintained 3-bedroom, 2.5-bath home in the highly sought-after Longleaf at Oakland community! From the moment you arrive, you will appreciate the inviting feel, thoughtful layout, and pride of ownership throughout. Inside, enjoy spacious bedrooms, a versatile upstairs loft perfect for a home office, media room, or additional living space, and a comfortable family room designed for everyday living and entertaining. Step outside to a wonderful backyard and porch area, with both the family room and porch pre-wired for speakers—perfect for creating an effortless indoor-outdoor entertaining experience. The two-car garage even features an electric vehicle charging outlet. The location is hard to beat— take a quick 5-minute walk to the West Orange Trail, enjoy the shops, dining, and charm of Downtown Winter Garden just 10 minutes away, and reach the Florida Turnpike in minutes. Beautifully cared for, ideally located, and truly move-in ready—this is the Oakland home you’ve been waiting for!

2696 Bobcat Chase Boulevard, Winter Garden

$409,000

3 Beds ⋅ 2 Baths ⋅ S5157851 MLS

LOCATION, LOCATION, LOCATION, Exceptional value is found with this spacious 3 bedroom, 2 bathroom home. You will appreciate the fully remodeled home with new flooring, kitchen cabinets and countertops, hall and master bathrooms, roof, water heater, pluming, and covered porch. This property is located across the street from Winter Garden High School and 5 minutes away from downtown Winter Garden and convenient access to major highways.

1606 Beulah Road, Winter Garden

$598,800

4 Beds ⋅ 3 Baths ⋅ O6442363 MLS

Pro pics coming but dont wait. FIRST TIME EVER OFFERED FOR SALE! Welcome to 14543 Sabal Crest Way, an exceptionally maintained, original-owner home located in the highly sought-after Orchard Hills community of Winter Garden. Pride of ownership is evident around every corner of this beautiful single-story residence, offering 4 bedrooms, 3 full baths and 2,224 heated square feet with an ideal combination of comfort, efficiency and location. Just a block from the Orchard Hills clubhouse, fitness center and playground, this home puts some of the community’s best amenities practically at your doorstep. Inside, the heart of the home is an impressive kitchen designed for both everyday living and entertaining. Enjoy built-in double convection ovens, a vented cooktop, abundant cabinetry and an oversized center island overlooking the main living areas. The open, functional one-story floor plan provides excellent separation of space while remaining bright, inviting and easy to live in. The upgrades continue throughout the property, including custom closet systems, gutters, fully fenced backyard and a 220-volt outlet in the garage ready for EV charging. One of the biggest bonuses is the fully paid-off 8.19 kW solar panel system, providing significant dent in the monthly electric savings without the burden of a solar loan or lease. The HOA handles the lawn care too !!! Location of this home is remarkable. Orchard Hills is ideally positioned near the rapidly growing Hamlin retail, dining and commercial district, SR 429 Expressway, Walt Disney World, the new community park and library, and everything Horizon West and Winter Garden have to offer. The property is located within a sought-after K-12 public school district and is also just minutes from the campuses of Foundation Academy and Windermere Preparatory School. Homes combining this condition, one-story living, four bedrooms, three full baths, a fenced yard, community amenities, paid-off solar and an outstanding Winter Garden location are increasingly difficult to find at this value. Meticulously cared for by its original owners, this home is truly move-in ready and an absolute cream puff. You simply won't find more for less. Schedule your private showing and move quickly—14543 Sabal Crest Way is ready for its second owner!

14543 Sabal Crest Way, Winter Garden

$600,000

3 Beds ⋅ 3 Baths ⋅ G5117862 MLS

PRIVATE POOL & SPA. 3-CAR GARAGE. SINGLE-STORY LIVING. AND JUST 5.8 MILES FROM WALT DISNEY WORLD! Welcome to 16137 Hampton Crossing Drive, where your own private Florida retreat meets the resort-style lifestyle of WATERLEIGH in HORIZON WEST—Winter Garden’s highly desirable newer community corridor. This beautifully maintained DR Horton Arbor floor plan offers 3 BEDROOMS, 3 FULL BATHS and an OVERSIZED 3-CAR TANDEM GARAGE, all thoughtfully arranged across 2,040 square feet on one level. Step inside to a bright, OPEN, SPLIT-BEDROOM FLOOR PLAN with high ceilings, engineered HARDWOOD FLOORING and an easy flow from the kitchen through the dining and living areas. The SPACIOUS kitchen is truly the heart of the home, featuring STONE COUNTERS, abundant cabinetry, stainless steel appliances, a large island with seating and a farmhouse-style sink. The privately positioned PRIMARY SUITE features a tray ceiling, walk-in closet and spacious ENSUITE BATH with DUAL VANITIES and an oversized walk-in shower. Two additional bedrooms and two full baths provide plenty of flexibility for guests, a home office or whatever fits your lifestyle. Then step outside—and this home really starts to show off. The COVERED LANAI opens to a fully SCREENED OUTDOOR RETREAT with your own HEATED SALTWATER POOL AND SPA, generous pool deck and space to relax, entertain or simply ENJOY FLORIDA LIVING year-round. In WATERLEIGH, your backyard is only the beginning. Community amenities include a CLUBHOUSE, RESORT-STYLE POOL, FITNESS CENTER, DOG PARK, PLAYGROUND, sidewalks and access to LAKE HICKORY NUT with fishing opportunities and a community pier. EVEN BETTER—INDIVIDUAL HOMEOWNER LAWN CARE IS INCLUDED, leaving you more time to enjoy everything about this home and community. All of this in HORIZON WEST, one of Central Florida’s most desirable newer communities, and only 5.8 MILES FROM WALT DISNEY WORLD, with shopping, dining, entertainment and major roadways nearby. Your own PRIVATE POOL and SPA, resort-style community amenities AND someone else takes care of the lawn? WELCOME to Florida living!

16137 Hampton Crossing Drive, Winter Garden

$620,000

3 Beds ⋅ 2 Baths ⋅ S5157882 MLS

Discover refined living in this beautifully appointed corner-lot residence in desirable Horizon West. Designed with elegance and everyday comfort in mind, this exceptional home features a spacious open floor plan, split-bedroom design, 3 bedrooms, 2 full baths, and a versatile den. The gourmet kitchen showcases 48-inch cabinetry, a beautiful glass-front display cabinet, and granite countertops, creating a nice space for both everyday living and entertaining. The corner setting provides abundant natural light and enhanced privacy, while the HOA includes lawn maintenance for added convenience. Ideally located near Publix, Walmart, Starbucks, restaurants, cafés, Cinepolis Luxury Cinemas, Urban Air Trampoline Park, and highly rated schools. Convenient access to Hwy 429 and Hwy 535.

8091 Bowery Drive, Winter Garden

$1,159,900

7 Beds ⋅ 5 Baths ⋅ O6442063 MLS

Welcome to an exceptional expression of modern luxury in Winter Garden’s highly sought-after Wincey Groves community. Crafted by Dream Finders Homes, this impressive 2021 Sweetwater residence offers more than 4,700 square feet of beautifully appointed living space, with 7 bedrooms, 4.5 baths, and two additional flex rooms that provide the extraordinary potential to create a 9-bedroom estate. Designed for those who value both refined living and remarkable versatility, this move-in-ready residence offers an unparalleled combination of scale, sophistication, and functionality in one of Central Florida’s most desirable destinations. A striking enhanced elevation, extended driveway, and welcoming front porch create an impressive first impression. Beyond the entry, an abundance of natural light illuminates the open-concept interior, where soaring ceilings, 9-foot doors, upgraded engineered hardwood flooring, and expansive sliding glass doors create a seamless sense of space and connection. Thoughtful design details throughout the residence create an atmosphere that is simultaneously elegant, comfortable, and effortlessly livable. The main-level primary suite is a private sanctuary, enhanced by additional windows that bathe the room in natural light. The spa-inspired en-suite bath delivers a luxurious retreat with an oversized soaking tub designed for two, an upgraded glass-enclosed shower, and beautifully selected finishes. Also on the main level, a private office provides an ideal setting for remote work, while a sophisticated half bath serves guests. A third garage bay has been thoughtfully converted into a fully equipped home gym, offering a dedicated space for fitness and wellness. At the center of the home, the gourmet kitchen is designed to be both a showpiece and a gathering place. An oversized island anchors the space, complemented by sleek quartz countertops, wrap-around cabinetry, double ovens, built-in microwave, farmhouse sink, under-cabinet lighting, and exceptional storage. Whether hosting an elegant dinner party or enjoying a quiet morning at home, this kitchen is perfectly suited to every occasion. Upstairs, generously proportioned bedrooms are paired with expansive walk-in closets and a convenient Jack-and-Jill bath. The home’s entertainment offerings are equally impressive, with a dedicated theater and game room creating an elevated destination for movie nights, gaming, and unforgettable gatherings. Two additional flex rooms offer exceptional adaptability, with endless possibilities for guest suites, creative spaces, study areas, multi-generational living, or additional work-from-home accommodations. Modern conveniences further enhance the residence, including smart-home technology, fiber-optic internet, a fully hardwired security system with cameras, and dual AC units for year-round comfort. Front and rear covered porches extend the living experience outdoors, overlooking a private, fenced backyard that provides an inviting setting for entertaining, relaxing, and enjoying Florida’s year-round lifestyle. Ideally located near top-rated schools, scenic parks, and the vibrant Hamlin Town Center, residents enjoy convenient access to premier shopping, dining, entertainment, and everyday amenities. More than a residence, this is a lifestyle defined by space, sophistication, versatility, and opportunity. Experience the exceptional firsthand with a private showing.

5074 Breezy Acres Street, Winter Garden

$730,000

5 Beds ⋅ 3 Baths ⋅ O6443027 MLS

Virtually Staged. Welcome to 2470 Standing Rock Circle, a beautifully maintained Montclair model by Meritage Homes in the desirable Oakland Trails community. Offering 3,446 square feet, 5 bedrooms, and a spacious open floor plan, this home has been meticulously cared for and is truly move-in ready. The first floor features a bedroom with a full bath, providing a comfortable and private space for guests. The main living areas flow seamlessly together and include surround sound in the living room, creating an inviting space for everyday living and entertaining. Step outside to the extended covered lanai spanning the full length of the home, with additional pavers extending the outdoor living area into the fully fenced backyard. Upstairs, you'll find the spacious primary suite with a tray ceiling, three additional bedrooms, and an oversized loft currently used as a theater room, complete with surround sound. This flexible space is perfect for movie nights, a game room, home office, or additional living area. Adding even more value, the exterior of the home will be freshly painted prior to closing, and the garage floor will receive a fresh epoxy finish. Located in charming Oakland, residents enjoy convenient access to the West Orange Trail, Oakland Nature Preserve, and Lake Apopka, while being just minutes from Historic Downtown Winter Garden with its restaurants, shops, Plant Street Market, Farmers Market, and year-round community events. With easy access to shopping, dining, and major roadways, this home offers plenty of space in a fantastic Central Florida location.

2470 Standing Rock Circle, Winter Garden

$525,000

4 Beds ⋅ 2 Baths ⋅ O6440519 MLS

RARE FIND in prime OAKLAND, Florida, only a 1/4 mile away from the WEST ORANGE TRAIL: a COMPLETELY REMODELED turn-key home on an OVERSIZED 0.25-ACRE LOT with VERY LOW HOA FEES! Why settle for tiny high-density lots when you can have true space, privacy, and full peace of mind? This FULLY MODERNIZED 4-bedroom, 2-bathroom residence offers over 2,000 square feet of luxury, with major big-ticket items already completed, including a NEW ROOF IN 2024 and a NEW AC IN 2023. Step inside to this inviting and fresh home with satin-white interior paint, NEW FIXTURES AND HARDWARE throughout, and low-maintenance LUXURY VINYL PLANK FLOORING with NO CARPET anywhere. The BRIGHT KITCHEN features SPARKLING QUARTZ COUNTERTOPS, a CLASSIC WHITE SUBWAY TILE BACKSPLASH, a STAINLESS STEEL HOOD, a DOUBLE-OVEN, and SPACIOUS 42-INCH UPPER CABINETS. Both bathrooms have been tastefully modernized, highlighted by a complete primary suite revamp. Outside, the QUARTER-ACRE PROPERTY features a NEW 6-FOOT VINYL PRIVACY FENCE, a MASSIVE 15x40 BACK PATIO perfect for outdoor dining, ALL-NEW SOD AND LANDSCAPE, a MATURE AND PRODUCING MANGO TREE, an IRRIGATION WELL for MAJOR UTILITY SAVINGS, and ample room to build a pool. Nestled in charming, canopy-lined Oakland, FL—prized for its quiet, Old-Florida feel and proximity to the West Orange Trail—you're minutes from historic Downtown Winter Garden’s famous weekly farmers market, craft breweries, boutique shopping, and fine dining. Best of all, instant connectivity to SR-50, FL-429, and the Florida Turnpike puts Downtown Orlando, Walt Disney World, Universal Studios, and all major Central Florida attractions within an easy 20-minute drive. CALL TODAY TO SCHEDULE A VISIT!

990 Stationside Drive, Winter Garden

Winter Garden/Oakland Homes for Sale

Newest Winter Garden/Oakland Homes for Sale