Winter Garden/Oakland Homes with Pool

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

$399,000

3 Beds ⋅ 3 Baths ⋅ O6442127 MLS ⋅ N/A BLDG.

Welcome home to this gorgeous end unit townhome in the heart of Hamlin! With capabilities of fencing in the side yard, this townhome offers potential unlike any other. Step inside and admire the fresh color palette this home boasts. With light wood-plank tile flooring, light countertops, light cabinetry, and lots of windows, this open concept downstairs feels incredibly warm and inviting. Updated lighting and window drapes elevate the space even more. Functionality and convenience were also taken into consideration in this downstairs with a cabinet and counter-lined drop zone upon entry into the home from the garage and patio, a closet pantry, and hallway leading to the half bathroom. Head upstairs where you will find a split bedroom floor plan with the primary suite on one side and the secondary bedrooms and Jack-and-Jill styled bathroom on the other, the space separated even further by the upstairs laundry room. Step out back to the private fenced-in brick-paved patio that separates the house from the two-car garage. The community is situated right in the middle of Hamlin’s shopping, dining, and entertainment offerings, super close to Disney, and right off of Highway 429 to bring you to all of your favorite Central Florida destinations. Inquire today on how to make this gem your own!

15579 Honeybell Drive, 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

$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

$399,900

3 Beds ⋅ 3 Baths ⋅ O6439860 MLS ⋅ Na BLDG.

OPEN-CONCEPT LIVING • OVERSIZED KITCHEN ISLAND • HARD-SURFACE FLOORING • SPACIOUS PRIMARY SUITE • PRIVATE PAVER PATIO • COMMUNITY POOL • WINTER GARDEN 34787 This Winter Garden townhome brings together the features that make a difference: a spacious open-concept layout, oversized kitchen island, abundant natural light, hard-surface flooring on the main level, staircase and upstairs hallway, generous storage, interior laundry, a spacious primary suite, private enclosed paver patio and access to the community pool. Welcome to 8049 Basilica Lane, a two-story residence offering 3 bedrooms, 2.5 bathrooms and approximately 1,860 sq ft, with thoughtfully connected indoor and outdoor spaces. The entry opens to a bright foyer featuring tile flooring, recessed lighting, a sidelight window and textured accent wall. From here, the floor plan transitions naturally into the kitchen, dining and living areas, creating one continuous gathering space. Large windows bring in natural light, while the open layout provides flexibility for different furniture and dining configurations. At the center of the main level, the kitchen features dark cabinetry, stainless-steel appliances, built-in microwave, range, dishwasher, pendant lighting and an oversized island with extended countertop seating. Generous cabinetry and counter space provide plenty of room for meal preparation and storage. Large-format tile flooring extends throughout the main gathering areas, creating a cohesive and low-maintenance surface. Continue upstairs via a hard-surface staircase with no carpet, where the upstairs hallway also features hard-surface flooring. Multiple closets provide additional storage, and a dedicated interior laundry closet offers space for a side-by-side washer and dryer with shelving above. The primary bedroom offers multiple windows, a tray ceiling and decorative wall detailing. The primary bathroom includes a long dual-sink vanity, extensive countertop and cabinet storage, a large wall mirror, tile flooring and an oversized glass-enclosed shower with tiled surround and built-in shower shelving. Step outside to a private enclosed paver patio designed to extend the living space outdoors. The fenced area provides room for lounge seating, outdoor dining and grilling, while shade coverings and string lighting add functionality for daytime and evening use. The community also offers a swimming pool with a spacious paver deck and lounge areas surrounded by Florida landscaping. Located in Winter Garden’s 34787 area, the property is convenient to Horizon West and Hamlin, with shopping, restaurants, grocery stores, entertainment and recreation nearby. Major Central Florida roadways provide connections to Walt Disney World, Windermere, Downtown Winter Garden and the greater Orlando area. Schedule your private showing today and come experience 8049 Basilica Lane in person!

8049 Basilica Lane, 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

$598,800

4 Beds ⋅ 3 Baths ⋅ O6442363 MLS

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

$409,900

3 Beds ⋅ 3 Baths ⋅ O6443446 MLS ⋅ N/A BLDG.

WELCOME HOME TO ONE OF THE MOST DESIRABLE FLOOR PLAN IN THE AREA! This exceptionally well-maintained townhouse in Winter Garden offers the perfect blend of comfort, space, and resort-style living. Step inside to a thoughtfully designed open-concept main floor featuring upgraded ceramic tile flooring, a massive kitchen island, a spacious pantry, a convenient half bath, and a generous laundry room. Upstairs, discover three well-appointed bedrooms, including a spacious primary suite with a beautifully sized bathroom featuring windows for natural light and a fantastic walk-in closet. The cherry on top? A generously sized backyard, offering valuable outdoor space for relaxing, entertaining, or enjoying time with family. The detached two-car garage provides convenience and functionality. Located in a beautiful, family-oriented community, residents enjoy resort-style amenities, including a sparkling pool, clubhouse with a game room, kitchen, and fitness center, basketball court, three dog parks, playgrounds, scenic lakes, and abundant green spaces. Children can even bike to the elementary and middle schools located within the neighborhood, while the high school is just minutes away! Enjoy the exceptional Winter Garden lifestyle, with Disney fireworks views from the community, HOA-organized resident activities, and convenient access to Disney, Flamingo Crossings, the Hamlin area, shopping, dining, and major roadways, including State Road 429. A wonderful opportunity to own a spacious, move-in-ready home in a sought-after location!

11120 Suspense Drive, 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

$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

$1,090,000

5 Beds ⋅ 5 Baths ⋅ O6441968 MLS

Stunning Mediterranean-style home in the sought-after Watermark community of Winter Garden! This 5-bedroom, 4.5-bath home offers a spacious open layout with custom finishes throughout, including custom wood paneling with LED accent lighting, designer curtains and light fixtures, and luxury vinyl plank flooring on every floor. The gourmet kitchen features KitchenAid appliances (built-in oven, built-in microwave, cooktop, dishwasher), double sink, walk-in pantry, and a bright breakfast nook overlooking the living area. The living room boasts a custom electric fireplace with built-in wood shelving. A dedicated den/office with custom cabinetry and a formal dining room with custom cabinetry and built-in wine fridge add versatility. One bedroom and full bath are located downstairs — perfect for guests — while upstairs offers four bedrooms including a luxurious primary suite with his-and-hers vanities flanking a built-in soaking tub, separate shower, and private water closet. The upstairs loft comes complete with a projector and screen, ideal for a home theater. Enjoy Florida living at its finest in the screened lanai, complete with a summer kitchen (grill, sink, refrigerator) and motorized retractable screen. Additional highlights include a laundry room with utility sink, screened pool, and a 2-car garage with paver driveway. Watermark residents enjoy access to a community pool and clubhouse for just $160/month HOA. Don't miss this move-in-ready gem!

9845 Emerald Berry Drive, Winter Garden

$849,900

4 Beds ⋅ 3 Baths ⋅ O6440789 MLS

Located in The Sanctuary at Twin Waters, and ideally positioned on the community’s largest homesite at the end of a quiet cul-de-sac with no rear neighbors and water views. A long driveway, three-car garage, an oversized, and a fully fenced backyard. Inside, the open-concept layout features 4 bedrooms and 3 full baths, with updated flooring throughout the main living areas and primary suite. The kitchen is complete with stainless steel appliances, an oversized island, quartz countertops, upgraded backsplash, and 42-inch cabinetry. The living room is complete with a stone electric fireplace and custom built-ins. Sliding glass doors open to a screened and covered lanai, creating an easy transition to outdoor living and entertaining. A whole-home solar system, FULLY PAID-OFF, adds energy efficiency, and eliminates the electricity bill. Residents of The Sanctuary at Twin Waters enjoy access to a community pool, playground, walking trails, and private pier. Just minutes from Winter Garden’s Historic Downtown, shopping, dining, Cinepolis Luxury Cinema, Horizon West, the West Orange Trail, major highways, and Orlando’s world-famous theme parks. Call today to schedule a private tour.

16668 Sanctuary Drive, Winter Garden

Winter Garden/Oakland Homes with Pool

Newest Winter Garden/Oakland Homes with Pool