Winter Garden Homes with Pool Community Features

Winter Garden Homes with Pool Community Features

Welcome to Winter Garden, Florida – a picturesque city nestled in the heart of Orange County. Known for its charming downtown area and vibrant community spirit, Winter Garden is a delightful blend of small-town warmth and modern conveniences. With scenic parks, beautiful lakes, and a rich history, this city offers a tranquil lifestyle just a stone's throw from the bustling attractions of Orlando.

One of the highlights of living in Winter Garden is the abundance of homes with pool community features. Imagine stepping out of your back door to a sparkling pool, perfect for warm Florida days spent soaking up the sun or hosting gatherings with family and friends. These communities are designed for comfort and leisure, providing residents with a resort-style living experience right at home.

Winter Garden's homes with pool community features often come complete with lush landscaping, spacious backyards, and access to amenities such as clubhouses, fitness centers, and walking trails. Whether you’re looking for a cozy single-family home or a more expansive property, the real estate options here cater to a variety of lifestyles and budgets.

Beyond the beautiful homes, Winter Garden boasts a thriving arts scene, farmer's markets, and a variety of dining options that showcase the local flavor. With easy access to major highways and the nearby attractions of Orlando, residents enjoy the perfect balance of serene living and urban excitement. Discover the charm of Winter Garden – where your dream home with a pool awaits!

Newest Winter Garden Homes with Pool Community Features

1229 Winter Green Way, Winter Garden
$235,000
2 Beds ⋅ 2 Baths ⋅ Village Grove Ph 02 SubDv. ⋅ 34787 Zip Code
Virtually Staged. This charming 2-bed, 1.5-bath townhouse delivers peak Central Florida convenience. Step inside to discover a bright, open interior highlighted by high ceilings and a stylish kitchen finished with sleek granite countertops. Meticulously maintained and move-in ready, it serves as the perfect low-maintenance starter home or turnkey addition to an investment portfolio. Five minutes to historic downtown Winter Garden, and under 30 minutes to Disney. Easy highway access rounds out a truly prime location. Tour Today!

1229 Winter Green Way, Winter Garden
922 Marsh Reed Drive, Winter Garden
$679,000
5 Beds ⋅ 3 Baths ⋅ Johns Lake Pointe A & S SubDv. ⋅ 34787 Zip Code
Picture a Saturday here. Coffee at the kitchen island while the pool glistens under the Florida sun. Cannonballs by noon, burgers on the grill by five, and a movie night in the loft once everyone dries off. Welcome to 922 Marsh Reed Drive, a 5 bedroom, 3 full bath saltwater pool home in Johns Lake Pointe that has been cared for like a prized possession and is ready for its next chapter. The first impression sets the tone: tropical landscaping, a brick paver driveway, a three car garage, and a covered front porch with a cheery red door. Step inside and the tiled foyer opens to a formal dining room framed by tall windows and warm natural light, the kind of room that turns holiday dinners and Sunday suppers into traditions. Keep walking and the home opens up. The kitchen is the true gathering spot, with 42" espresso cabinets, granite counters, a tiled backsplash, stainless appliances, built-in double wall ovens, pendant lighting, and a large island where homework, snacks, and conversation all happen at once. A walk-in pantry with custom shelving keeps the grocery runs organized. The eat-in dining area sits right off the kitchen with sliding glass doors to the pool, so you can keep an eye on the swimmers while dinner comes together. The family room flows right alongside, finished with crown molding, plantation shutters, and wiring for surround sound. Game day, movie night, or a lazy Sunday nap, this room handles it all. Hosting overnight company? A first-floor bedroom next to a full bath makes a private guest retreat or a quiet home office away from the upstairs bustle. Head up the staircase with wrought iron spindles and you’ll find a huge loft that gives everyone room to spread out: game room, playroom, homework zone, or second living room. Three secondary bedrooms share a full bath, and the laundry room is right here on the second floor with custom cabinetry, which means no more hauling baskets up and down the stairs. The primary suite is split to its own side of the second floor, with windows on two sides and room for a reading chair. The en suite bath feels like a getaway, with dual sinks and granite counters, a frameless glass shower, a separate garden tub for long soaks, and two walk-in closets so nobody has to negotiate for hanger space. Then there’s the backyard, where this home really shines. The saltwater pool is heated by solar panels, extending swim season well beyond summer. An extended paver deck has room for a full grill lineup, a dining table, and lounge chairs, with an electric retractable awning for shade when you want it. Vinyl privacy fencing wraps the entire yard, giving you a private oasis with plenty of grass for playing catch or running through the sprinkler. Smart upgrades work quietly in the background: rain gutters around the entire home, French drains in the yard, whole-home water softening system, and a central vacuum in the garage. Life in Johns Lake Pointe adds even more to love, with a resort-style community pool, clubhouse, fitness center, tennis courts, playground, and walking trails. Bike the West Orange Trail, catch the Saturday farmers market in Historic Downtown Winter Garden, explore Tucker Ranch, or shop and dine at Winter Garden Village, all just minutes away. SR 429, SR 408, and the Florida Turnpike make commutes and theme park days easy. Homes like this don’t come along often. Schedule your private showing and see why this one is ready to feel like yours.

922 Marsh Reed Drive, Winter Garden
651 Autumn Oaks Loop, Winter Garden
$535,000
3 Beds ⋅ 2 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code
Live the Winter Garden lifestyle you've been dreaming of in the Winter Oaks community, with oak-lined streets and golf cart access to downtown. Situated in the Golf Cart District, this park-side residence overlooks majestic oaks and open green space. The 3-bedroom, 2-bath, 1,768 sq ft home features a 2021 ROOF, 2021 HVAC, UPDATED LIGHT FIXTURES, a GAS STOVE, a REAR-ENTRY 2-CAR GARAGE, and a RECENTLY PAINTED INTERIOR, with freshly painted bedrooms, baths and laundry room. As you walk in, you're greeted by natural light and an open, welcoming feel. A formal dining room and an open kitchen flow into the spacious family room, which leads out to a NEWLY RE-SCREENED back patio overlooking a beautifully manicured lawn and garden. The primary suite includes a spacious walk-in closet and a private bath with dual sinks, a soaking tub, and a separate shower. Winter Oaks offers a community pool, cabana, playground, and scenic pond. Hop in your golf cart to Plant Street for dinner, a show at the Garden Theatre, or the Saturday farmers market. Minutes from the West Orange Trail, Tucker Ranch, and Newton Park, Winter Garden Village with an easy drive to SR 429 and the Florida Turnpike. Convenient access to Disney, Universal, Epic Universe, and downtown Orlando. Schedule your private showing today!

651 Autumn Oaks Loop, Winter Garden
13728 Fox Glove Street, Winter Garden
$649,900
5 Beds ⋅ 4 Baths ⋅ Stoneybrook West Ut 04 48 48 SubDv. ⋅ 34787 Zip Code
Spacious 5-bedroom, 3.5-bath home with 3,391 square feet overlooking the 14th hole of the golf course in Stoneybrook West. The main floor features a primary suite, a second bedroom with its own en-suite bathroom, and a separate powder room. Upstairs are three additional bedrooms and a full bathroom. The home features high ceilings, an open floor plan, plenty of natural light, and a 2-car garage. Sliding glass doors open to a large covered patio and screened-in private pool with golf course views. Recent improvements include a new roof (2025), upstairs AC (2025), and downstairs AC (2022). Stoneybrook West is a 24-hour guard-gated community with a clubhouse, fitness center, community pool, tennis courts, playground, and access to Black Lake with a private boat ramp. Conveniently located near Winter Garden Village, downtown Winter Garden, and SR-429.

13728 Fox Glove Street, Winter Garden
949 Celadon Street, Winter Garden
$2,195,000
5 Beds ⋅ 5 Baths ⋅ Oakland Parka SubDv. ⋅ 34787 Zip Code
Discover exceptional custom craftsmanship in this J&J Builders home, located in a golf cart-friendly community just minutes from downtown Winter Garden and the West Orange Trail. Featuring 5 bedrooms and 4.5 bathrooms, this home offers a thoughtfully designed open floor plan with beautiful views of Lake Apopka. The spacious chef's kitchen is the heart of the home, featuring high-end Sub-Zero and Miele appliances and creating an ideal setting for everyday living and entertaining. A dedicated office offers the flexibility to serve as a potential sixth bedroom. The stunning upstairs primary suite is a true retreat, showcasing dramatic cathedral beamed ceilings and breathtaking lake views. An additional private suite downstairs offers flexibility for guests or multigenerational living, while two additional upstairs bedrooms share a bath. The home also features a separate in-law suite with its own kitchenette, providing even more versatility for extended family or visitors. Designed for comfortable living and effortless entertaining, the home seamlessly blends indoor and outdoor living. Step outside to your own private retreat, featuring a heated inground pool and spa, an inviting covered lanai, and a fully equipped outdoor kitchen with automatic retractable screens. Gather around the natural gas fire pit with included outdoor furnishings and enjoy beautiful Florida evenings. Additional highlights include a large garage attic storage room with convenient accordion-style metal access stairs, offering valuable extra storage space. Enjoy the best of Winter Garden living with custom craftsmanship, high-end finishes, versatile living spaces, resort-style outdoor amenities, and convenient access to the area's beloved shops, dining, and outdoor recreation!

949 Celadon Street, Winter Garden
15625 Murcott Harvest Loop, Winter Garden
$650,000
3 Beds ⋅ 3 Baths ⋅ Highlands At Summerlake Groves Phase 1 SubDv. ⋅ 34787 Zip Code
Beautifully appointed SINGLE-STORY home in the highly desirable Summerlake community of Horizon West! The GOURMET KITCHEN is sure to impress with a massive center island, stainless steel appliances, GAS COOKTOP, built-in wall oven and microwave, stunning backsplash, and walk in pantry. 8 FOOT DOORS, CROWN MOLDING, and Phillips Hue SMART LIGHTING are some of the additional design upgrades. You will love the open, inviting floor plan. The open office offers flexibility and can easily be converted into a 4TH BEDROOM. Enjoy energy efficiency and significant savings with SOLAR PANELS, which will be PAID IN FULL AT CLOSING, and an average electric bill of approximately $30 per month! Additional energy upgrades include a TANKLESS WATER HEATER and a NEW HIGH-EFFICIENCY AC SYSTEM with TWO UV FILTERS. Summerlake is a natural gas community offering an impressive array of amenities, including a clubhouse, RESORT-STYLE POOL, fitness center, tennis and basketball courts, playgrounds, parks, and miles of walking and biking paths, with scenic boardwalks connecting lakes and natural areas. The HOA also includes CABLE AND INTERNET! Conveniently located near Hamlin Town Center for shopping, dining, coffee shops, and entertainment, with additional shopping and restaurants at Winter Garden Village. Enjoy the charm of Historic Downtown Winter Garden, Plant Street Market, the weekly farmers market, and the West Orange Trail. Golf enthusiasts will appreciate nearby Orange County National Golf Center. Easy access to SR-429 puts Walt Disney World and the greater Orlando area within easy reach. This home offers the perfect combination of style, comfort, energy efficiency, and an outstanding Horizon West lifestyle!

15625 Murcott Harvest Loop, Winter Garden
9953 Summerlake Groves Street, Winter Garden
$774,900
4 Beds ⋅ 4 Baths ⋅ Watermark Ph 4a SubDv. ⋅ 34787 Zip Code
Premium Corner Lot! Discover this beautiful two-story home in the sought-after Watermark community of Horizon West in Winter Garden! Situated on a desirable corner lot, this well-maintained home offers 4 spacious bedrooms, a den, a versatile bonus room, an office, 3.5 bathrooms, and an oversized two-car garage with epoxy flooring. Step inside to a bright and welcoming open floor plan featuring abundant natural light and a spacious layout designed for comfortable everyday living. The inviting living room connects seamlessly to the covered lanai, featuring an outdoor summer kitchen, creating a wonderful space for relaxing, entertaining, and enjoying Florida's beautiful weather. The gourmet kitchen features a large center island with a sink, generous space for preparing meals, and an adjoining dining area perfect for family gatherings. Upstairs, the primary suite provides a relaxing retreat with access to a private screened balcony, where you can enjoy your morning coffee or unwind in the evening. The additional bedrooms offer comfortable living spaces, while the versatile bonus room can easily serve as a playroom, media room, or additional entertainment area. This home also features a fully functional water softener system, hot and cold water connections, and sewer service, adding convenience and functionality to everyday living. Outside, the fully fenced backyard offers added privacy and plenty of space for outdoor activities and gatherings. The oversized two-car garage with epoxy flooring provides additional convenience and storage space. Residents of Watermark enjoy resort-style amenities, including a community pool, splash pad, playground, tennis courts, recreation center, and outdoor amphitheater. Conveniently located in the heart of Horizon West, this home is just minutes from Disney, shopping, restaurants, and entertainment, with easy access to SR-429 for convenient travel throughout Central Florida. With its premium corner lot, spacious interior, desirable features, fantastic community amenities, and excellent Winter Garden location, this home offers a wonderful opportunity to experience the best of Florida living!

9953 Summerlake Groves Street, Winter Garden
580 First Cape Coral Drive, Winter Garden
$675,000
4 Beds ⋅ 3 Baths ⋅ Black Lake Park Ph 01 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to Black Lake Park, one of Winter Garden's sought-after gated communities, where spacious family living, fantastic amenities and an enviable location come together to create the perfect Florida lifestyle! Offering 4 SPACIOUS BEDROOMS, 2 1/2 BATHROOMS, AND HUGE LOFT AREA, this beautiful home provides the ideal combination of comfort, space and functionality. The welcoming open-plan layout creates an easy flow between living spaces, making everyday family life effortless, and entertaining a pleasure. With NO CARPETS THROUGHOUT, NEWLY PAINTED INTERIOR and a NEW ROOF – INSTALLED DECEMBER 2024, this home offers even more appeal and peace of mind, with a clean, practical and easy-to-maintain living environment. Whether hosting friends, enjoying family time or simply relaxing at home, with 2834 sq ft there's room for everyone. It does not stop there. Step outside and discover what Florida living is all about! Your private fully fenced backyard retreat, features a NEW FABULOUS SALTWATER SWIMMING POOL AND SPA – INSTALLED DECEMBER 2025! Imagine soaking up the sunshine, cooling off on warm afternoons or unwinding in the spa after a busy day. With plenty of room for lounging, outdoor dining and entertaining this is an outdoor space you'll love coming home to! Life in Black Lake Park is something special! This FABULOUS, GATED, FAMILY-FRIENDLY COMMUNITY offers an outstanding range of recreational facilities, making it a wonderful place for families and those who enjoy an active outdoor lifestyle. Amenities include TENNIS COURTS, BASKETBALL COURTS, BASEBALL FIELDS, A COMMUNITY SWIMMING POOL AND PLAYGROUND, along with lovely walking paths, and COMMUNITY DOCK AND BOAT RAMP. Whether enjoying a family game, taking a leisurely stroll, spending time at the park or heading out onto the water, there's something for everyone to enjoy. It's a community where outdoor living, family fun and a wonderful neighborhood atmosphere come together. This LOCATION is hard to beat. Simply wonderful! Just minutes from the charm of Historic Downtown Winter Garden, where you'll find an abundance of restaurants, cafés, boutique shopping and the much-loved Winter Garden Farmers Market. Winter Garden Village is also close by, offering an excellent choice of shopping, grocery stores and everyday conveniences. For commuters and those who love to explore, easy access to the 429, Florida Turnpike and Highway 50 makes traveling around Central Florida very convenient. Walt Disney World and the area's world-famous attractions are also within easy reach, making this a fantastic location for enjoying everything that is available in Central Florida. Whether you're searching for your next family home, the perfect place to entertain or simply somewhere to enjoy everything the Florida sunshine has, this is an opportunity not to be missed. THIS HOME IS MOVE IN READY! COME AND DISCOVER THE LIFESTYLE WAITING FOR YOU IN BLACK LAKE PARK.

580 First Cape Coral Drive, Winter Garden
9991 Schroeder Alley, Winter Garden
$378,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Phase 2d SubDv. ⋅ 34787 Zip Code
Welcome home to 9991 Schroeder Alley, tucked away in Winter Garden’s highly coveted, resort-style community of Waterleigh! From the moment you step inside, you will feel the perfect blend of modern comfort and effortless Florida living. This stunning townhome has been meticulously maintained and offers ultimate peace of mind with major structural upgrades already taken care of—featuring a brand-new HVAC system (2026) and a solid roof and water heater (both 2019). You won't have to spend a dime on the big-ticket items; you can simply move in, unpack, and start living your best life. New dishwasher (2026) and that the washer and dryer convey. What truly sets this home apart is the incredible lifestyle that comes with it. Living in Waterleigh feels like being on a permanent vacation. You are just steps away from world-class amenities, including multiple resort-style pools, dynamic fitness centers, a beautiful community clubhouse, beach volleyball, tennis and pickleball courts, dog parks, and scenic walking trails around clean, peaceful lakes. Located in the heartbeat of Horizon West, you are only minutes away from the charming shops and dining at the Horizon West Regional Center, Winter Garden schools, and local favorites like the Winter Garden Village. Best of all? You are so close to Disney World that you can end your evenings watching the nightly fireworks light up the sky right from your neighborhood. Whether you’re looking for a low-maintenance sanctuary or a vibrant, active community to call home, this Horizon West gem is the one you’ve been waiting for. Schedule your tour today and fall in love with the Waterleigh lifestyle!

9991 Schroeder Alley, Winter Garden
1218 Painted Bunting Avenue, Oakland
$517,500
3 Beds ⋅ 2 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Virtually Staged. **WELCOME HOME** Pond views, beautiful upgrades, and an unbeatable location just minutes from Downtown Winter Garden! BUILT IN 2020 with FRESH EXTERIOR PAINT (2026), this SINGLE-STORY home in the charming Longleaf at Oakland community offers a sought-after floor plan, stylish finishes, and a fantastic location with no direct front or rear neighbors. A welcoming COVERED FRONT PORCH overlooks a peaceful community pond, creating a tranquil setting to relax and enjoy the view. Inside, LUXURY VINYL PLANK FLOORING flows throughout the home, complementing the light, bright, and OPEN LIVING SPACES. The home chef will appreciate the well-appointed kitchen featuring QUARTZ COUNTERTOPS, timeless cabinetry topped with crown molding, a gray ARABESQUE MOSAIC TILE BACKSPLASH, stainless steel appliances, a BUILT-IN OVEN and microwave, cooktop with vent hood, and a spacious ISLAND with PENDANT LIGHTING. A convenient BUILT-IN WORK SPACE just off the kitchen is ideal for a home office or homework station. The thoughtfully designed floor plan offers comfortable bedrooms and beautifully finished bathrooms with granite countertops and gray cabinetry, plus CUSTOM CLOSET built-ins in one of the secondary bedrooms. POCKET SLIDING GLASS DOORS open to the SCREENED LANAI, complete with roller shades for added comfort and privacy. Beyond the porch, a FENCED BACKYARD provides a rare bonus for this style of home, offering outdoor space while still enjoying the convenience of a 2-CAR REAR FACING GARAGE with epoxy flooring. Additional street parking is available out front. Even better, the HOA takes care of the lawn maintenance! Longleaf at Oakland is a quaint, welcoming community with a pool and playground just steps from your front door. Outdoor enthusiasts will love being just a 5-minute stroll from the West Orange Trail, while the shops, restaurants, farmers market, and charm of Historic Downtown Winter Garden are all less than 10 minutes away! Commuters will appreciate quick access to the Florida Turnpike, SR 50, and SR 429, with Lake Apopka, parks, shopping, and everyday conveniences all nearby. ZONED FOR TOP RATED SCHOOLS - Tildenville Elementary, Lakeview Middle, and West Orange High School. Enjoy the benefits of NEWER CONSTRUCTION, thoughtful UPGRADES, LOW MAINTENANCE LIVING, and a prime Oakland location without sacrificing proximity to everything Winter Garden has to offer. Schedule your tour today!

1218 Painted Bunting Avenue, Oakland
17449 Water Hemlock Road, Winter Garden
$1,099,990
5 Beds ⋅ 5 Baths ⋅ Lake Star At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. The Newport home at 17449 Water Hemlock Road has something for everyone! Learn more about this 5-bedroom home by contacting our team today! Welcome to your new home at 17449 Water Hemlock Road in Winter Garden, a thoughtfully designed quick move-in opportunity ready when you are! This beautifully crafted new construction home offers 5 spacious bedrooms and 5 full baths, designed for comfort and everyday living. The open-concept layout creates a seamless connection between the kitchen, dining, and living areas, making the home feel bright, open, and welcoming. Natural light pours in throughout the day, accentuating stylish finishes and a layout that’s as practical as it is inviting. The owner’s bedroom serves as a private retreat with plenty of room to relax and recharge. Your en-suite owner’s bathroom provides a comfortable, spa-inspired setting with thoughtful finishes and ample space designed to make daily routines feel effortless and relaxing. Additional bedrooms provide versatility for guests, a home office, or creative spaces to fit your lifestyle, while a 2-car garage adds everyday convenience and extra storage. Located in a welcoming neighborhood, this home home offers the perfect balance of style and simplicity. Whether you’re enjoying a quiet morning at home or hosting friends and family, the layout supports a comfortable, easygoing lifestyle designed to grow with you for years to come. This new construction home delivers style, comfort, and move-in-ready ease without the wait. This move-in-ready new construction home delivers modern style, thoughtful design, and the convenience of no build wait. Contact us today to learn more about this exceptional home at 17449 Water Hemlock Road!

17449 Water Hemlock Road, Winter Garden
17443 Water Hemlock Road, Winter Garden
$859,990
4 Beds ⋅ 3 Baths ⋅ Lake Star At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to this stunning new construction home located at Lake Star At Ovation, Winter Garden, Florida. Built by M/I Homes, this 2-story home offers 2,754 square feet of thoughtfully designed living space across 2 above-ground levels, featuring 4 bedrooms and 3 bathrooms. Step inside to discover an open-concept living space that creates a seamless flow between gathering areas, perfect for everyday living and entertaining. The quality of design is evident throughout, with carefully selected finishes and well-planned layouts that maximize both comfort and functionality. Key Features: 4 spacious bedrooms and 3 full bathrooms 2,754 square feet of living space Open-concept living space for seamless entertaining Private owner's bedroom with en-suite bathroom Covered lanai for outdoor relaxation 2-car garage The owner's bedroom features a private en-suite bathroom, providing a comfortable retreat at the end of each day. The lanai extends your living space outdoors, offering a covered area to enjoy the Florida weather year-round. The Lake Star At Ovation neighborhood provides a welcoming setting with proximity to parks and recreational spaces, making it an ideal place for those who enjoy an active outdoor lifestyle. This home combines quality construction with a functional floorplan designed for modern living.

17443 Water Hemlock Road, Winter Garden
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