Winter Garden Homes with Private Pool type

Winter Garden Homes with Private Pool type

Welcome to Winter Garden, Florida, a hidden gem nestled just a short drive from the bustling heart of Orlando. Known for its charming downtown area, vibrant community spirit, and picturesque landscapes, Winter Garden offers a delightful blend of small-town charm and modern conveniences. This city is surrounded by lush greenery and scenic lakes, providing residents with ample opportunities for outdoor recreation, from biking along the West Orange Trail to enjoying leisurely afternoons at the nearby Lake Apopka.

For those seeking the ultimate in luxury and relaxation, Winter Garden boasts an impressive selection of homes with private pools. Imagine stepping into your own backyard oasis, where you can unwind under the Florida sun or host memorable gatherings with family and friends. These homes are designed for both comfort and entertainment, featuring spacious layouts, modern amenities, and beautifully landscaped outdoor spaces.

The allure of a private pool not only enhances your lifestyle but also adds significant value to your property. Whether you prefer a serene morning swim or evening barbecues by the water, having a private pool transforms your home into a personal retreat. With a variety of styles and sizes available, you can find the perfect home that fits your needs and desires.

Winter Garden is not just a place to live; it’s a community that embraces a vibrant lifestyle. With top-rated schools, diverse dining options, and year-round events, you’ll find everything you need right at your fingertips. Explore the charm of Winter Garden and discover your dream home with a private pool today!

Newest Winter Garden Homes with Private Pool type

3 Beds ⋅ 2 Baths ⋅ Hull Island/Oakland SubDv. ⋅ 34787 Zip Code

Welcome home to Hull Island, where thoughtful upgrades, a private preserve setting, and resort-style amenities come together. This beautifully maintained 3-bedroom, 2-bath home backs to protected conservation land with no rear neighbors. High ceilings, electronic shades, and abundant natural light give the home an open, airy feel. The chef’s kitchen features an oversized granite island, a gas stove, pot filler, 42-inch cabinets, and additional upper cabinetry for storage. Tile backsplash, built in conventional oven and microwave. From the kitchen, you can look out over the pool while preparing meals. The spacious primary bedroom has been updated to the larger size upgrade with the builder. Master bathroom features a double vanity and a very large walk in shower with dual showerheads and a built-in bench, providing both comfort and convenience. Built in 2024, the custom screened-in pool area and waterfall is made for relaxing and entertaining. It includes a summer kitchen with a sink and a gas fire pit. The home also offers a washer and dryer, an electric tankless water heater, and a recently installed Generac natural-gas whole-house generator designed to turn on automatically during a power outage. This home also has an irrigation system heling you keep the landscaping looking its best year- round! The HOA is $165 per month, with no CDD. Community amenities include a resort-style pool, playground, dog park, and a boardwalk leading to a dock and fishing pier on Lake Apopka. Residents also have a private entrance to the 120-acre Oakland Nature Preserve. Downtown Winter Garden, the West Orange Trail, farmers markets, shopping, dining, golf, and pickleball are all close by. With its preserve views, inviting outdoor space, and convenient location, and privacy this move-in-ready home is a rare find. The photos are not virtually staged—this home truly is breathtaking!

2107 Bay Line Road, Oakland

5 Beds ⋅ 3 Baths ⋅ Wintermere Harbor SubDv. ⋅ 34787 Zip Code

Welcome to the Winter Garden lifestyle! Set behind the gates of desirable Wintermere Harbor, this impressive 5-bedroom, 3-bath pool home offers over 3,700 square feet of beautifully designed living space with the room, flexibility and privacy today’s buyers are looking for. From the moment you walk in, soaring ceilings and generous living spaces create a bright, open feel perfect for both everyday living and entertaining. The heart of the home flows effortlessly to your screened-in pool and private backyard oasis—imagine morning coffee by the water, sunny Florida afternoons by the pool and evenings entertaining family and friends. With five bedrooms and multiple living areas, there’s plenty of space for a home office, guests, playroom or multigenerational living. Beyond your front door, Wintermere Harbor offers gated entry, a playground, park and access to Lake Luntz. And the location is hard to beat! You’re just minutes from Winter Garden’s shopping, restaurants and everyday conveniences, with quick access to SR-429 making it easy to reach Downtown Orlando, the airport and surrounding Central Florida. Walt Disney World and the attractions are also just a short drive away, putting the best of Central Florida practically in your backyard. Spacious, private, gated and perfectly positioned—this is more than a house. It’s the Florida lifestyle you’ve been waiting for.

2102 Green Ash Court, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Wincey Grvs Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to 5416 Golden Apple Dr, an exceptional 5-bedroom, 3.5-bath home in WINCEY GROVES, just moments from the heart of Hamlin. The experience begins at the UPGRADED DECORATIVE-GLASS FRONT DOOR, opening to warm wide-plank flooring, statement lighting, clean architectural details, and a contemporary staircase with black metal accents. Continue into the main living space and the home’s personality really comes through. A dramatic CUSTOM WOOD-SLAT MEDIA WALL WITH BUILT-IN CABINETRY anchors the room, while the open kitchen brings everyone together around an expansive island with stone countertops, abundant cabinetry, stainless steel appliances, and modern pendant lighting. Throughout the home, DESIGNER LIGHT FIXTURES, CUSTOM MILLWORK, BUILT-INS, AND MOTORIZED WINDOW TREATMENTS elevate the spaces well beyond standard builder finishes. Behind the scenes, an ALEXA-INTEGRATED SMART HOME SYSTEM provides convenient control of multiple connected features throughout the residence. The floor plan is equally thoughtful, with the PRIMARY SUITE AND MAIN BEDROOMS LOCATED DOWNSTAIRS for comfortable everyday living. Even the primary suite has something unexpected—a CONCEALED ENTRY DOOR that blends discreetly into the wall before opening to an oversized retreat with a bay-window sitting area overlooking the pool and custom walk-in closets. Upstairs feels like its own private destination, featuring a GUEST BEDROOM, FULL BATH, AND EXPANSIVE BONUS LIVING AREA WITH A BUILT-IN BEVERAGE CENTER, WINE COOLER AND MINI REFRIGERATOR—perfect for overnight guests, extended family, movie nights, a game room, or simply having an entire second living space away from the main level. Then the experience moves outside. MOTORIZED RETRACTABLE SCREENS allow the covered lanai to transition from open-air living to a screened retreat at the touch of a button, overlooking a HEATED SALTWATER POOL, expansive paver deck, tropical landscaping, and fully fenced backyard. And when evening arrives, DISNEY FIREWORKS LIGHT UP THE HORIZON from the comfort of your own backyard. The location completes the picture, with HAMLIN TOWN CENTER APPROXIMATELY ONE MILE AWAY and convenient access to dining, shopping, entertainment, SR-429, Horizon West, Walt Disney World, and everything the Winter Garden area has to offer. At 5416 Golden Apple Dr, it isn’t one upgrade that makes the difference—it’s how thoughtfully everything has been brought together. Schedule your private showing and experience it for yourself.

5416 Golden Apple Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Oakland Hills SubDv. ⋅ 34787 Zip Code

Custom-built by Justice & Wood Builders, this 4-bedroom, 3-bathroom Modern Farmhouse sits on a rare 0.47-acre lot in Oakland Hills, an intimate community of just 17 homesites minutes from Historic Downtown Winter Garden. Towering, moss-draped oaks frame the property and set a peaceful tone from the moment you arrive. Inside, wide-plank wood floors and abundant natural light flow through an open-concept living space crowned by cathedral ceilings and exposed timber beams. The kitchen goes well beyond standard gourmet, with shaker cabinetry, quartz countertops, a massive blue-gray center island, a deep farmhouse sink, professional stainless steel appliances, and a natural gas range built for serious cooking. The bedrooms are generously sized and well separated. The upstairs bedroom is flexible enough to serve as a home office, gym, media room, or guest suite, and it has air-conditioned storage and a large walk-in attic. The bathrooms feature clean lines, modern fixtures, and custom tilework. The laundry room has extensive cabinetry, quartz counters, and a patterned tile backsplash. The three-car garage includes an EV adapter in the third bay. Out back, the fully fenced yard feels like your own resort, with a pool and spa surrounded by a spacious paver patio and a fire pit area for evenings outside. Downtown Winter Garden's Farmers Market, Plant Street Market, boutiques, and restaurants are minutes away by car or golf cart.

15210 E Oakland Avenue, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Latham Park North SubDv. ⋅ 34787 Zip Code

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

3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1c SubDv. ⋅ 34787 Zip Code

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

5 Beds ⋅ 5 Baths ⋅ Watermark Ph 3 SubDv. ⋅ 34787 Zip Code

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

4 Beds ⋅ 4 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code

Welcome to 6158 Meriwether Crescent in Winter Garden! This spacious 4-bedroom home offers a flexible floor plan with plenty of room to spread out, plus a private screened-in pool that makes Florida living easy. The main living areas feature an open layout with wood and tile flooring, while the kitchen offers granite countertops, stainless steel appliances, ample cabinetry and breakfast-bar seating. Large windows throughout bring in plenty of natural light, and multiple living and dining spaces provide flexibility for everyday living, entertaining or working from home. Step outside to the screened pool and patio overlooking a peaceful green setting, creating a great place to relax or entertain year-round. A detached garage with a brick-paver driveway adds even more functionality, while the covered front porch and mature landscaping give the home welcoming curb appeal. The surrounding community offers beautiful green space, walking paths, ponds and a neighborhood gazebo just steps from the home. Conveniently located in Winter Garden with easy access to shopping, dining, schools and everything the area has to offer, this home combines space, privacy and outdoor living in a great location.

6158 Meriwether Crescent, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code

If you’ve been searching for a spacious Winter Garden home with a private pool, peaceful conservation views and room for everyone, this former model may be exactly what you’ve been waiting for! With 5 bedrooms, 4 full bathrooms and the potential for a 6th bedroom, this home combines privacy, flexibility and Florida indoor-outdoor living in a way that’s increasingly difficult to find. Situated on a peaceful wooded conservation lot, the home has been thoughtfully updated with a renovated kitchen, LVP flooring throughout the first floor, and new carpet and paint upstairs. Generous living and dining areas provide plenty of room for everyday living and entertaining, while the family room features easy access to the screened pool and deck. The spacious primary suite includes a private sitting area and built-in shelving, creating a comfortable retreat. Upstairs, the oversized bonus room with its own adjoining full bathroom offers exceptional flexibility and could serve as a second primary suite, private guest quarters, media room or game room. Need even more space? The downstairs office could potentially be converted into a 6th bedroom, making this floor plan adaptable to a variety of needs. Step outside to one of the home's most appealing features—the screened-in pool and deck overlooking the wooded conservation area. With no immediate rear neighbor, it's a private setting for morning coffee, afternoons by the pool, entertaining friends or simply relaxing at the end of the day. Located in the beautiful gated Wintermere Pointe community, this home brings together the space, privacy and flexibility along with a private pool and conservation setting that can be difficult to find. Call and schedule your private showing today!

2242 Wintermere Pointe Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to 15675 Panther Lake Drive, an exceptional lakefront residence within the prestigious Lakeshore Preserve community of Winter Garden, where refined interiors, expansive water views, and effortless Florida living come together in a beautifully curated setting. Offered fully furnished, this sophisticated five-bedroom, five-bathroom residence has been thoughtfully enhanced with custom millwork, elevated finishes, and carefully selected upgrades throughout. The heart of the home is an expansive open-concept living space, seamlessly connecting the family room, dining area, and kitchen while framing beautiful views of the lake. Designed equally for intimate everyday living and sophisticated entertaining, the main level also features a dedicated coffee station, generous pantry and storage spaces, laundry room, and a private primary suite offering the convenience of first-floor living. One of the three garage bays has been thoughtfully transformed into a fully equipped private fitness studio, creating a dedicated wellness space within the residence while offering the flexibility to be converted back to garage use if desired. Upstairs, four additional bedrooms are complemented by a spacious loft and private home office. Expansive windows throughout the upper level capture the lake views and bring an abundance of natural light into the home. Beyond its interiors, the property's waterfront setting creates a sense of openness and tranquility, offering a beautiful lake view and access, summer kitchen, Florida room, heated pool and a spa. It is a true oasis from morning through evening. Ideally positioned in Winter Garden, the residence provides the privacy and distinction of an upscale community while remaining conveniently connected to the area's exceptional dining, shopping, entertainment, and lifestyle destinations. 15675 Panther Lake Drive represents a rare opportunity to acquire a fully furnished*, beautifully appointed lakefront home where comfort, functionality, and the Florida lifestyle exist in perfect balance.

15675 Panther Lake Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Lake Roberts Lndg E SubDv. ⋅ 34787 Zip Code

Your chance to own the FORMER MODEL for entire community. Set behind the GATED ENTRY of Lake Roberts Landing with community fishing pier to 116 acre Lake Roberts. THE IDEAL FLOOR PLAN you have been waiting for, 5 beds, office, movie theatre and bonus.. PLUS this rare gem... Primary bed and an additional En Suite on 1st floor !!! Incredible street presence and MASSIVE fenced back yard. Oversized covered lanai with summer kitchen provides the ideal place to relax and entertain. Screen enclosed pool and spa with paver deck competes the perfect back yard to embrace the Florida Lifestyle. Entering the home you are greeting with soaring ceilings of a foyer replicating a great hall feel. Formal dining and private office (on top of the 5 bedrooms) flank the entry, Both boasting amazing detail and carpentry that would be expected in the former model. Pass the wet bar for entertaining to the formal living room with same soaring ceiling height as the foyer itself. The heart of the home well appointed with timeless wood cabinets, lots of workspace and vented cook top too. The family room overlooks the pool, yard and lanai. DOWNSTAIRS MASTER is incredible and a RARE SECOND EN SUITE DOWNSTAIRS is perfect for guests or aging family members. Ascend the showstopping curved staircase to the equipped home theatre and additional BONUS ROOM. 2 large secondary bedrooms with jack and jill set up PLUS another EN SUITE/ 2nd primary bedroom on the 2nd floor. ALL beds have a walk-in closet too ! 3 car tandem garage, tile roof. Minutes to 429 expressway, countless shopping and dining options in literally every direction. Sought after K-12 school district plus Foundation Academy and Windermere Preparatory school campuses minutes away. Disney less than 15 away and 20 to Downtown Orlando. This is truly an amazing opportunity for one buyer. Move fast, this is one that is priced to sell.

1720 Lake Roberts Landing Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Wintermere Harbor Ph 02 48 21 SubDv. ⋅ 34787 Zip Code

Welcome home to this one-story pool home situated on an oversized lot that overlooks a pond! ***NEW WINDOWS, NEW COMMODES, 2022 ROOF, 2020 SMART POOL*** Tucked into the back of this gated community, this spacious oasis is ready for its next owners. One of Florida's most popular floor plans features a formal living space at the entrance of the home, casual living space in the middle of the home, the primary suite privately on one side of the home, and the 3 secondary bedrooms on the other side of the home. Choose to repurpose the "formal living space" into whatever your wants and needs may be, or use them as the formal living room and formal dining room as the builder intended. The primary suite has an extension included and is ready to be used as yet another flex space. French doors open from this extension right onto the covered outdoor living space. The primary bathroom boasts a soaking tub, dual vanities, and 2 custom closets. The casual living space is open and inviting with the kitchen, large dining nook, and family room, and lots of natural light brightens this space up even more by way of a wall of sliding glass doors that lead to the outdoor living space, another door with a window that also leads to the outdoor living space, and a set of bay windows in the dining nook. Bedrooms 2 and 3 are located down a hallway off of the casual living space and have a full bathroom they share. The 4th bedroom is in the back of the home with its own bathroom. Step out back to the screened in patio which holds a gorgeous pool with a sun shelf and waterfall, covered portion, and extension under the screen for total and full enjoyment opportunities! Continue outside of the screen enclosure to the fully fenced in backyard that overlooks a pond. Whether looking for peace and serenity or fun and activity, this home has a solution to it all! Inquire today to for a private viewing to see if this gem will become your next home!

2039 Harbor Cove Way, Winter Garden

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