Winter Garden Homes with Pool Community Features

Winter Garden Homes with Pool Community Features

Welcome to Winter Garden, Florida, a charming city nestled in the heart of Orange County that perfectly blends small-town charm with modern amenities. Known for its picturesque landscapes, vibrant downtown area, and rich history, Winter Garden offers residents a unique lifestyle that is both relaxed and engaging. With its proximity to Orlando, residents enjoy easy access to world-class attractions while relishing the serene atmosphere of suburban living.

One of Winter Garden’s standout features is its delightful array of homes with pool community offerings. Imagine coming home to your own private oasis, where you can unwind in the refreshing waters of your pool after a long day. These communities are designed with family-friendly amenities that promote a sense of community and connection. From clubhouses and playgrounds to walking trails and picnic areas, there’s something for everyone to enjoy.

The homes in these neighborhoods are not only beautiful but also thoughtfully designed to cater to modern lifestyles. Spacious layouts, updated kitchens, and lush outdoor spaces are just a few of the features that make living in Winter Garden a dream come true. Whether you’re entertaining friends by the poolside or enjoying a quiet evening under the stars, these homes provide the perfect backdrop for creating lasting memories.

As you explore Winter Garden, you’ll find a community that celebrates its history while embracing the future. With a thriving local economy, excellent schools, and a welcoming atmosphere, it’s no wonder why so many choose to call Winter Garden home. Come experience the magic of this enchanting city and discover your perfect poolside retreat!

Newest Winter Garden Homes with Pool Community Features

$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
Pro pics coming but dont wait. 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
$415,000
2 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
Well-maintained and thoughtfully updated, this New Independence townhome offers the perfect combination of style, comfort, and low-maintenance Florida living, all while located in a highly desirable community. Step inside to find updated flooring throughout, plantation shutters, and a bright, inviting layout designed for effortless everyday living. The renovated primary suite adds a modern, elevated touch, while the home’s thoughtful design provides the perfect setting for both relaxing and entertaining. Outside, discover a beautifully organized backyard oasis—a private space to enjoy your morning coffee, host friends, or simply take advantage of the Florida sunshine. And the lifestyle extends well beyond the property. New Independence offers an impressive collection of amenities, including two resident clubhouses, two resort-style pools with cabanas and grills, a whirlpool spa, two fitness centers, tennis and basketball courts, parks, playgrounds, and more than 6 miles of walking, running, and biking trails. Residents also have private lake access with boat ramps and on-lake ski ramps serving the lakes between Lake Hancock and Lake Speer. The community also features two dedicated dog parks, including separate areas for large and small dogs. Additionally, the HOA also includes basic high-speed internet and cable TV service, adding even more value to the community’s amenities package. Location is a major advantage; this home is only minutes from the popular Hamlin shopping and dining district, as well as the Winter Garden Village, downtown Winter Garden, and major roadways. Enjoy convenient access to some of the area’s best restaurants, shopping, and everyday necessities while still coming home to a peaceful, established community. Updated. Turnkey. Ideally located. And ready for its next owner.

5751 New Independence Parkway, Winter Garden
$509,900
3 Beds ⋅ 2 Baths ⋅ Summerlake Pd Phase 2a And 2b SubDv. ⋅ 34787 Zip Code
SUMMERLAKE | WINTER GARDEN | HORIZON WEST | MOVE-IN READY Beautifully maintained one-story 3-bedroom, 2-bath home in the highly desirable Summerlake community, ideally located just minutes from Hamlin Town Center. Enjoy convenient access to shopping, dining, entertainment, top-rated schools, and major highways. The bright open-concept floor plan seamlessly connects the living, dining, and kitchen areas, with large windows providing abundant natural light. The kitchen features ample cabinetry, modern appliances, a breakfast bar, and NEW DISHWASHER & MICROWAVE. The spacious primary suite offers a walk-in closet and private bath with dual sinks, soaking tub, and separate shower. Two additional bedrooms share a full bathroom. TILE FLOORING THROUGHOUT provides a clean, durable, and low-maintenance finish. ROOF REPLACED IN 2026 and INTERIOR & EXTERIOR PAINT COMPLETED IN 2026, offering valuable peace of mind to the new owner. The attached garage includes a SPLIT A/C UNIT, creating a flexible space for storage, hobbies, recreation, or other personal use. The covered SCREENED-IN LANAI is perfect for relaxing and enjoying the Florida lifestyle. Located JUST ONE BLOCK FROM THE COMMUNITY CLUBHOUSE, this home offers exceptional convenience to Summerlake’s resort-style amenities, including a community pool, fitness center, tennis courts, playgrounds, walking trails, and clubhouse. HOA INCLUDES LAWN CARE, providing added convenience and low-maintenance living. Prime location near Hamlin Town Center, DISNEY, Publix, Walmart, restaurants, cafés, boutique shopping, Cinépolis Luxury Cinemas, PopStroke, Urban Air, Adventure Park, SR-429, and nearby schools including Summerlake Elementary, Hamlin Middle, and Horizon High School. Move-in ready with a new roof, fresh 2026 interior/exterior paint, new kitchen appliances, tile flooring throughout, screened lanai, and an unbeatable Winter Garden location. Schedule your private showing today!

14931 Porter Rd, Winter Garden
$465,900
4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 2c 2d 2e SubDv. ⋅ 34787 Zip Code
LAKEFRONT LUXURY IN SUMMERLAKE! Stunning 4BR/3BA townhome with bonus room, open concept living, brand new roof, state of the art appliances & decorative lighting included! Enjoy breathtaking lake views, nightly Disney fireworks, and a private PVC fenced brick paver courtyard perfect for morning coffee or relaxing. Spacious 2 car garage. Resort style amenities include clubhouse, gym, pool, soccer field, walking trails, tennis court, basketball court, playground, zip line & fishing dock. Walking distance to the Orange County National Golf Center, minutes to Disney, Downtown Winter Garden, endless dining & shopping. A MUST SEE! Buyer to verify room sizes and all measurements. Public records reflect 3BR/2BA; actual configuration is 4BR/3BA plus bonus room

8174 Bluejack Oak Drive, Winter Garden
$595,000
4 Beds ⋅ 3 Baths ⋅ Orchard Hills Phase 2 SubDv. ⋅ 34787 Zip Code
Welcome to this bright and airy 4-bedroom, 2.5-bath home offering a comfortable and inviting layout. The spacious kitchen opens directly to the living room, creating a great flow for everyday living and entertaining, and features a large island with plenty of room for meal prep or gathering with family and friends. The open feel continues throughout the main living areas, with plenty of natural light adding to the welcoming atmosphere. The primary bedroom offers a private retreat with its own door leading to the balcony, providing a nice spot to step outside and enjoy the fresh air.

14354 Orchard Hills Boulevard, Winter Garden
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