Winter Garden Homes with Pool Community Features

Winter Garden Homes with Pool Community Features

Winter Garden, located in Orange County, Florida, is a charming city known for its historic downtown, beautiful parks, and family-friendly atmosphere. The city offers a mix of modern amenities and a touch of old Florida charm, making it a desirable place to live for people of all ages.

For those looking for homes with pool community features in Winter Garden, you're in luck! Many neighborhoods in Winter Garden offer this sought-after amenity, providing residents with the perfect place to cool off and relax during the hot Florida summers. Whether you're looking for a single-family home with a private pool or a community pool where you can socialize with your neighbors, Winter Garden has plenty of options to choose from.

Living in a home with pool community features in Winter Garden allows residents to enjoy the outdoor lifestyle that Florida is famous for, all while building a strong sense of community with their neighbors. So, if you're in the market for a home in a vibrant city with great amenities, consider Winter Garden for your next move.

Newest Winter Garden Homes with Pool Community Features

$459,900
3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Welcome to Del Webb Oasis in Winter Garden, where everyday living feels like a getaway. This semi-furnished, 3-bedroom, 2-bath home offers approximately 1,579 square feet of comfortable living space. The spacious kitchen features a gas stove and plenty of cabinet storage, while the primary suite includes a large walk-in closet and a walk-in shower. Two additional bedrooms offer room for guests or a home office, and the second bathroom also has a walk-in shower. The two-car garage includes an electric vehicle charging outlet and a utility sink. With flexible indoor and outdoor spaces, energy-efficient features, gas heating, and internet, cable, and gas included in the rent, the home is designed for easy living. Residents can enjoy the Del Webb Oasis clubhouse, fitness center, resort-style pool, pickleball and tennis courts, trails, and social activities, all near Winter Garden shopping, dining, and Orlando attractions. Del Webb Oasis is a 55+ community; occupancy is subject to community requirements. Assistance animal requests are reviewed in accordance with applicable law.

15193 Aqua Sol Lane, Winter Garden
$474,690
3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
Under Construction. Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! The new construction Foxtail Interior Unit townhome features 3 bedrooms, 2 full bathrooms, a powder room, an open concept kitchen, café and gathering room, a private courtyard, a 2-car rear-facing garage and our Move-In Ready package with includes a refrigerator, washer, dryer, and 2” faux wood blinds. The first floor is ideal for entertaining, featuring a spacious gathering room, café and kitchen, with a large center island, storage pantry, Trenton Burlap cabinets, a decorative tile backsplash, quartz countertops and Whirlpool stainless-steel kitchen appliances – including a refrigerator. A powder room and laundry on the first floor add to the thoughtful convenience. Enjoy entertaining loved ones from your private, fenced rear courtyard. After a long day, retreat upstairs to your private oasis. The Owner's Suite features a spacious walk-in closet and en suite bathroom with a double sink quartz-topped vanity, private water closet and a walk-in shower. Two additional bedrooms, the secondary bathroom and extra storage offered by a linen closet are on the opposite side of the second floor, offering privacy and space for everyone. Professionally curated design finishes for this popular Foxtail townhome include window blinds, luxury wood-look vinyl plank flooring throughout the first-floor, tile in the bathrooms, and soft, stain-resistant, Shaw brand carpet in the bedrooms and second floor living areas, and so much more.

6379 Argent Wood Drive, Winter Garden
$399,000
3 Beds ⋅ 3 Baths ⋅ Hamlin Reserve SubDv. ⋅ 34787 Zip Code
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 ⋅ Silverleaf Reserve SubDv. ⋅ 34787 Zip Code
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 ⋅ 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
$515,000
3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
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, Oakland
$598,800
4 Beds ⋅ 3 Baths ⋅ Orchard Hills SubDv. ⋅ 34787 Zip Code
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 ⋅ Storey Grove Ph 1b-1 SubDv. ⋅ 34787 Zip Code
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 ⋅ 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
$730,000
5 Beds ⋅ 3 Baths ⋅ Oakland Trails SubDv. ⋅ 34787 Zip Code
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, Oakland
$849,900
4 Beds ⋅ 3 Baths ⋅ Sanctuary/Twin Waters SubDv. ⋅ 34787 Zip Code
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
$729,999
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
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