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Homes for Sale with a Pool in Winter Garden, FL

Welcome to your dedicated resource for homes for sale with a pool in Winter Garden, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Winter Garden, FL agent, The Nest Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in Winter Garden, FL

$935,000
4 Beds 4 Baths Waterleigh Ph 1b SubDv. 34787 Zip Code
Welcome to this beautifully maintained 4-bedroom, 3.5-bath home situated on one of the largest corner lots in the highly sought-after Waterleigh community in Winter Garden. Offering nearly 3,000 square feet of thoughtfully designed living space, this home blends timeless style, comfort, and functionality. Step inside to an inviting open-concept floor plan filled with natural light, where the living room, dining area, and kitchen flow seamlessly together—perfect for both everyday living and entertaining. Plantation shutters throughout add elegance and charm. The gourmet kitchen is the heart of the home, featuring 42-inch espresso cabinetry, granite countertops, stainless steel appliances, a spacious island, and abundant storage, all overlooking the family and dining areas. The first floor offers flexibility with a private bedroom and full bath, ideal for guests or multigenerational living, along with a dedicated home office bathed in natural light. Upstairs, you’ll find a spacious loft that can easily serve as a media room, playroom, second living area, or additional office. The luxurious primary suite provides a peaceful retreat with room for a king-sized bedroom set, a large walk-in closet, and a spa-inspired ensuite featuring dual vanities, a walk-in shower, and a soaking tub. Two additional bedrooms share a full bathroom with dual sinks, while the conveniently located second-floor laundry room adds everyday convenience. Outside, enjoy your covered lanai overlooking the oversized backyard—one of the largest lots in the neighborhood—with plenty of room to build your dream pool while still maintaining green space. The three-car tandem garage provides ample parking and storage. Living in Waterleigh means enjoying resort-style amenities, including: three clubhouses, three resort-style pools, two fitness centers, tennis, pickleball, volleyball, and mini golf, walking and biking trails, dog park, fishing pier, playgrounds, and scenic lakes. Lawn maintenance included through the HOA Conveniently located just minutes from Historic Downtown Winter Garden, Winter Garden Village, SR-429, shopping, dining, and top-rated schools, this home truly offers the best of Central Florida living. Don’t miss your opportunity to own this exceptional home—schedule your private showing today!

16304 Wind View Lane, Winter Garden

$887,066
5 Beds 5 Baths Waterleigh SubDv. 34787 Zip Code
Under Construction. Waterleigh presents the Torrey. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room and butler’s pantry. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Located off the family room is a den with French doors perfect for work or play and a powder room. Customize this area to meet your needs with an optional bedroom and full bathroom. As we head up to the second floor, we are greeted with a loft area and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Like all homes in Waterleigh, the Torrey includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11869 Shine View Lane, Winter Garden

$870,000
4 Beds 4 Baths Bronsons Lndgs F & M SubDv. 34787 Zip Code
Tucked inside a sought-after gated community, this beautifully designed 4-bedroom, 4-bath home with office/den, offers the perfect blend of comfort, elegance, and everyday livability. From the moment you arrive, you’ll appreciate the sense of privacy, space, and thoughtful design that make this home truly special. With formal living and dining rooms, a private office/study, and a spacious bonus room with a full bath, there is room for everyone to live, work, gather, and unwind. At the heart of the home, the centrally located kitchen brings everything together, opening naturally to the main living areas and creating an ideal setting for both entertaining and daily life. Appointed with granite countertops, a center island, double ovens, and a pantry, it is as functional as it is inviting. Beautiful crown molding, decorative wall details, and tile flooring throughout the main living spaces add warmth and character, while the bedroom spaces provide comfort and privacy. The primary suite is a peaceful retreat, privately positioned and complete with two walk-in closets, dual vanities, a soaking tub, and a separate shower. Secondary bedrooms are thoughtfully arranged, including a Jack-and-Jill bath, while the bonus room provides flexible space for guests, a media room, a playroom, or multi-generational living. Step outside and enjoy your own private Florida oasis. The screened saltwater pool, convenient pool bath, and expansive paver deck with both covered and open-air areas create the perfect backdrop for quiet mornings, weekend gatherings, and year-round outdoor living. Backing to a green area, the setting feels peaceful and private, offering a rare sense of escape while still being close to everything. Located near Winter Garden Village, Highway 429, top-rated schools, shopping, and dining, this exceptional home offers not just a place to live, but a lifestyle to love. Make sure to check out the 3D tour and Virtual tours.

2139 Tillman Avenue, Winter Garden

$930,000
5 Beds 4 Baths Orchard Hills Ph 3 SubDv. 34787 Zip Code
Welcome to this beautifully maintained 5-bedroom, 3.5-bath home with a spacious 3-car garage, offering the perfect blend of comfort, style, energy efficiency, and location. From the moment you step inside, you’ll appreciate the soaring ceilings, open living spaces, and thoughtful upgrades throughout. The custom stone fireplace, bring an inviting ambiance to those cozy evenings or when entertaining guests year round. At the heart of the home is the gourmet kitchen, featuring granite countertops, built-in appliances, abundant cabinetry, and plenty of space for cooking and entertaining. The adjoining living area is highlighted by a built-in fireplace, creating a warm and inviting focal point for family gatherings. One of the home’s standout features is the fully owned solar system, helping keep monthly electric costs exceptionally low—averaging approximately $33 per month. The exterior has been recently painted, adding fresh curb appeal. Step outside to the expansive backyard designed with possibilities in mind. The generous outdoor space offers ample room to add a pool whilst still leaving plenty of space for a dedicated grilling and outdoor dining area. Whether you're hosting summer barbecues, family gatherings or relaxing with friends, the spacious yard provides the ideal setting for creating your own private outdoor retreat. The modern floor plan offers five bedrooms and 3.5 bathrooms, providing flexibility for families, guests, or a home office, along with a generous 3-car garage for vehicles and additional storage. Ideally located in one of Winter Garden’s most desirable communities, this home is zoned for highly rated schools and offers convenient access to Walt Disney World, SR-429, downtown Orlando, and Orlando International Airport (MCO), making commuting, travel, shopping, dining, and entertainment easily accessible. If you’re looking for a move-in-ready home with premium features, exceptional energy savings, generous living space, and an outstanding location, this home is ready to welcome you.

5079 Palmetto Park Drive, Winter Garden

$559,000
3 Beds 3 Baths Waterleigh Phase 3bcd SubDv. 34787 Zip Code
Welcome to this beautifully maintained home in the master-planned community of Waterleigh community of Horizon West in Winter Garden. This popular Bellake floor plan offers over 2,200 square feet of beautifully maintained living space. Rare concrete block construction on both the first and second floors, thoughtful updates by the current owner, and a functional open-concept layout make this home stand out from the moment you arrive. As you step inside, you're welcomed by a versatile flex room to the left, perfect for a home office, playroom, or formal sitting area, while the updated half bath with a new vanity and light fixture is conveniently located to the right. Continue into the spacious great room that flows seamlessly into the kitchen, creating an inviting space for everyday living and entertaining. The kitchen features stainless steel Whirlpool appliances, granite countertops, a large center island with additional cabinet storage, ample cabinetry, a dedicated dining area, and overlooks the main living space. Select areas of fresh interior paint, refreshed tile flooring, updated lighting, and a new ceiling fan add to the home's clean, well-cared-for feel. Just beyond the kitchen, a mudroom provides access to the attached two-car garage. Additional storage can be found beneath the staircase. Upstairs you'll find all three bedrooms, two full bathrooms, the laundry room, and an additional storage closet. The spacious primary suite features a beautifully remodeled en-suite bathroom with a walk-in shower finished in timeless subway tile, contrasting dark grout, sleek matte black fixtures, and a custom-designed walk-in closet. The secondary bedrooms share a full bathroom with a dual-sink vanity. Sliding glass doors off the great room open to the covered, screened lanai with paver flooring overlooking the side and backyard. The security system, security cameras, washer, and dryer all convey. Enjoy Waterleigh's resort-style amenities including four pools, four parks, two fitness centers, tennis courts, beach volleyball, putt-putt golf, walking trails, a fishing pier, and a beautiful clubhouse, while the HOA maintains the lawn and shrubs. Minutes from Hamlin Town Center, Publix, SR 429, Disney, and the shores of Hickory Nut Lake, you'll even enjoy Disney fireworks from your driveway. Schedule your private showing today!

15741 Fountain Springs Road, Winter Garden

$784,000
4 Beds 4 Baths Twinwaters SubDv. 34787 Zip Code
Incredible opportunity in sought-after Twinwaters. Built in 2018, this beautifully maintained and HIGHLY UPGRADED, energy-efficient POOL residence is move-in ready and offers the perfect combination of comfort, style, and functionality. The thoughtfully designed 4-bedroom, 3.5 bath ONE-LEVEL Avallon floor plan features an expansive gourmet kitchen that seamlessly overlooks the spacious family room, creating an ideal setting for everyday living and effortless entertaining. The adjoining breakfast nook with extended built-in cabinetry and an additional dedicated beverage refrigerator is perfect for morning coffee, casual meals, or gathering with family and friends. The "pocket office" just off the kitchen ensures no space is wasted and makes for unbelievable utility with everything you need right at your fingertips. From the custom wall treatments, crown molding, and upgraded light fixtures to the tranquil brick paver front porch to enjoy the neighborhood, you won't sacrifice a thing at this home. The generously sized primary suite serves as a private retreat with two walk-in closets, dual vanities, and a well-appointed en-suite bath. All bedrooms boast walk-in closets, making storage a breeze. The sparkling pool is the center of outdoor entertainment and is screened-in, surrounded by manicured grounds. Residents of Twinwaters enjoy exceptional community amenities, including a resort-style swimming pool, park, and playground, all within a convenient location close to great schools, shopping, dining, and major roadways. Designed with advanced energy-efficient construction, this home promotes a healthier, quieter lifestyle while helping reduce monthly utility costs. This property may be under audio/visual surveillance.

16736 Gullfloss Terrace, Winter Garden

$850,621
5 Beds 4 Baths Waterleigh SubDv. 34787 Zip Code
Under Construction. Waterleigh presents the Cresswell. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you’ll find a flex room perfect for work or play and downstairs powder room. The well-appointed kitchen overlooking the great room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. As we head up to the second floor, we are greeted with a loft area and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Customize the second floor of this home to create a space that meets your needs but transforming the loft area to a fifth bedroom with full bath or Guest Suite with ensuite bathroom. Like all homes in Waterleigh, the Cresswell includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11863 Shine View Lane, Winter Garden

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