Winter Garden Homes with Playground Community Features

Winter Garden Homes with Playground Community Features

Welcome to Winter Garden, Florida—a vibrant city nestled in the heart of Orange County, known for its charming blend of historic charm and modern conveniences. Just a short drive from the bustling Orlando metropolitan area, Winter Garden offers a serene escape with lush landscapes, picturesque lakes, and a rich cultural heritage. Its historic downtown district features delightful boutiques, artisanal eateries, and a lively farmers market that draws residents and visitors alike every Saturday.

One of the standout features of Winter Garden is its family-friendly atmosphere, particularly in the Homes with Playground Community. This community is designed with families in mind, boasting an array of amenities that cater to both children and adults. Imagine your little ones laughing and playing in the well-maintained playgrounds, while you enjoy leisurely strolls along the scenic walking trails that wind through the neighborhood. The sense of community here is palpable, with neighbors forming lasting friendships and engaging in various social activities throughout the year.

In addition to the playgrounds, residents can take advantage of community parks, picnic areas, and recreational facilities, ensuring that there is always something fun to do right at your doorstep. The combination of beautiful homes and a welcoming environment makes the Homes with Playground Community an ideal place for families to thrive.

Whether you’re looking to enjoy the great outdoors, indulge in local dining, or become part of a close-knit community, Winter Garden is the perfect place to call home. Come discover the charm and warmth of this delightful city today!

Newest Winter Garden Homes with Playground Community Features

13211 Lakeshore Grove Drive, Winter Garden
$715,000
4 Beds ⋅ 4 Baths ⋅ Wintermere Harbor SubDv. ⋅ 34787 Zip Code
Amazing Floorplan!! Three way split floorpan with 4 bedrooms and an office located on the first floor. Formal dining and living rooms. Corian kitchen counters with wood cabinets. Large spacious bonus room on the second level with half bath. Screen enclosed pool with large lanai. Large vinyl fenced in backyard. ROOF 2023. Gated Community with basketball court, playground and dock to Lake Luntz. Located just a few minutes from Winter Garden Villages and access to the 408 near Stoneybrook Parkway. All furniture is available for purchase.

13211 Lakeshore Grove Drive, Winter Garden
9766 Amber Chestnut Way, Winter Garden
$429,900
3 Beds ⋅ 3 Baths ⋅ Watermark Ph 3 SubDv. ⋅ 34787 Zip Code
Space, location, and the Horizon West lifestyle—all in one. Live minutes from Disney without feeling like you live in the middle of the tourist district. This 3-bedroom, 2.5-bath Watermark townhome gives you nearly 2,000 sq. ft., a dedicated first-floor office and an attached 2-car garage. High and tray ceilings, abundant natural light and an open floor plan make the space feel even larger. The kitchen brings granite countertops, espresso cabinetry, stainless steel appliances and a large island together with the dining and living areas. Upstairs, the primary suite includes a walk-in closet and private bath, with two additional bedrooms nearby. Watermark adds even more value outside the home, with community pools, clubhouse, fitness center, playgrounds and more. Hamlin, Flamingo Crossings, shopping, dining, SR-429 and Walt Disney World are all nearby—giving you the convenience of Horizon West without sacrificing the neighborhood feel.

9766 Amber Chestnut Way, Winter Garden
12349 Westfield Lakes Circle, Winter Garden
$740,500
4 Beds ⋅ 3 Baths ⋅ Westfield Lakes Ph 04 A-F SubDv. ⋅ 34787 Zip Code
Welcome to Westfield Lakes, a charming community nestled along the shores of Lake Beulah in desirable Winter Garden! This beautifully maintained custom built Morrison Home offers 5 bedrooms, 3 full baths, a 3-way split bedroom floor plan. The thoughtful floor plan includes a private bedroom and full bath separated from both the primary suite and additional bedrooms, making it ideal for guests, extended family, or an in-law suite. The home is on an oversized lot with no rear neighbors. From the moment you step inside, you'll appreciate the soaring 12-foot ceilings, abundant natural light, crown molding, and thoughtful design throughout. The spacious kitchen features 42-inch cabinetry, rich granite countertops, upgraded appliances, and plenty of room to gather with family and friends. The open family room is pre-wired for surround sound and overlooks the extended covered lanai and private backyard, creating an ideal space for entertaining or simply enjoying the peaceful Florida lifestyle. The oversized lot offers plenty of room to add a pool. The private primary suite is thoughtfully separated from the additional bedrooms and features a tray ceiling, direct access to the covered lanai, dual vanities, a large garden tub, and a separate fully tiled shower and a custom closet with built ins, which add both functionality and a custom feel. The fifth bedroom offers flexibility as a home office, den, or guest space. Additional features include 18-inch tile flooring, a spacious 3 car garage with epoxy flooring, brick paver driveway, brick privacy fencing, professional landscape edging, and a recently painted exterior. Major updates provide added peace of mind with a NEW ROOF in February 2026, NEW WATER HEATER and NEW A/C October 2026, plus the freshly painted exterior Sept 2026. Westfield Lakes offers residents a beautiful neighborhood park, tennis courts, and a fishing pier along Lake Beulah. Ideally located near West Orange High School, Roper YMCA Family Center, Winter Garden Village, historic Downtown Winter Garden, dining, shopping, entertainment, dog parks, the West Orange Trail, and major roadways including the 429, Turnpike, and 408. This is more than a home, it's an opportunity to enjoy the space, privacy, and lifestyle that make Westfield Lakes such a special place to call home. Come see it for yourself!

12349 Westfield Lakes Circle, Winter Garden
17602 Japonica Bloom Drive, Winter Garden
$785,000
5 Beds ⋅ 4 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Luxury new construction home near Walt Disney World theme parks! The spacious 5 bedroom, 4 bathroom design offers the perfect combination of style, functionality, and comfort. The home features a 3-car tandem garage, a covered front porch and a covered backyard lanai, ideal for outdoor relaxation or entertaining. The heart of the home is the chef-inspired gourmet kitchen, which includes solid surface countertops, an island, and high-end stainless steel appliances, such as a cooktop, range hood, built-in oven and microwave, and dishwasher. The spacious living area is designed with upgraded flooring and enhanced with natural light flowing in through dual-pane energy-efficient windows. Sliding glass doors allow access to the covered backyard patio, seamlessly blending indoor and outdoor living spaces. The private primary suite is a true retreat, featuring an extended sitting room off of the bedroom. The primary bathroom features a dual sink vanity with Delta faucets, ceramic tile flooring, a luxurious shower with a glass enclosure and a freestanding bathtub. Additional features include an upgraded lighting package, towel bars, and a huge walk-in closet, offering plenty of storage and comfort. The secondary bedrooms are generously sized, with each second floor bedroom surrounding a spacious loft. Additional features of this exceptional new home include a full sprinkler system, a complete landscaping package, energy-efficient construction, garage door openers, and a utility area with ceramic tile flooring. The home also boasts all 8' doors on the first floor, pre-plumb for a laundry sink, fully upgraded design finishes, including Revwood flooring, and a new home warranty for peace of mind. Call today to schedule a tour!

17602 Japonica Bloom Drive, Winter Garden
9918 Pallida Hickory Way, Winter Garden
$550,000
3 Beds ⋅ 3 Baths ⋅ Water Mark Phase 4 SubDv. ⋅ 34787 Zip Code
Welcome to Watermark, where location, lifestyle, and thoughtful upgrades come together in the heart of Hamlin. This beautifully maintained 3-bedroom, 2.5-bath home offers 1,892 square feet of comfortable, energy-efficient living with a floor plan designed for both everyday life and entertaining. Built by Meritage Homes, the home is filled with upgrades that set it apart, including plantation shutters, fresh interior paint, a custom pantry system, and an upgraded kitchen with refreshed cabinet hardware and soft-close hinges. The laundry room offers additional built-in cabinetry along with a premium LG washer and dryer. The primary suite features a custom closet system and a beautifully updated bathroom, while the guest bath is finished with porcelain tile. A dedicated wine storage area and high-end surround sound system add an extra touch for entertaining and enjoying the home. Practical upgrades are just as impressive, including epoxy-coated garage floors, a whole-home water softener, new A/C coils, and energy-efficient foam insulation. Outside your front door, Watermark offers a true resort-style lifestyle with four community pools, tennis courts, a clubhouse, playgrounds, and more. Located in the highly desirable Hamlin area, you’re just minutes from shopping, dining, entertainment, golf, and major roadways, with Panther Lake Elementary and Horizon High School nearby. And when the sun goes down, enjoy one of the home’s most memorable features: Disney fireworks views right from your own backyard. Move-in ready, thoughtfully upgraded, and positioned in one of Horizon West’s most popular communities. Come see what makes this Watermark home special.

9918 Pallida Hickory Way, Winter Garden
4540 Gliding Wave Street, Winter Garden
$560,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Preserve Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to 4540 Gliding Wave St, located in the highly sought-after gated, waterfront community of Lakeview Preserve in Winter Garden! Built in 2022 by Pulte Homes, this beautifully maintained Spruce model offers an exceptional blend of modern design, thoughtful upgrades, & comfortable living. Featuring 3-beds/2-baths, a stunning office w/custom built-in cabinetry, a 2-car garage w/epoxy flooring, & 2,144 sq. ft. of thoughtfully designed living space. This home is sure to impress! As you enter, you are greeted by a spacious foyer & premium luxury vinyl plank flooring that flows seamlessly throughout the home. To your right, elegant double doors open into an impressive private office—an ideal space for working from home or creating a relaxing personal retreat. Continue into the heart of the home, where the kitchen, dining, & living areas come together in a breathtaking open-concept design. This expansive layout is perfect for entertaining guests, family, or simply enjoying everyday living. The gourmet kitchen is truly a showstopper! Featuring Pulte Homes’ coveted Chef’s Kitchen pkg, it boasts: Quartz countertops, Upgraded range countertop, Stylish range hood, oven w/microwave combo, beautiful kitchen island, Stainless steel appl, Elegant pendant lighting, & Under-cabinet lighting. This kitchen delivers both style & functionality. The entertaining continues as you open the sliding glass doors to the fully enclosed lanai, creating an inviting extension of your living space. Here, guests can relax & enjoy the peaceful surroundings while taking in the beautiful view of your premium homesite—w/no rear neighbors! And when the mood strikes, your built-in 5-speaker surround sound system sets the perfect atmosphere with your favorite easy-listening music. Retreat to the spacious owner's suite, this private sanctuary features a large walk-in closet with an amazing custom closet system, an oversized walk-in shower, abundant linen storage, & a double vanity. Add’l upgrades: Crown molding, Built-in drop zone w/cabinetry conveniently located at the garage entry, Security system, Reverse Osmosis System–under counter kitchen water filtration system, the home has also been pre-plumbed for a whole-house water softener, Gutters, LED lighting, Built-in pest control system. The HOA fee includes access to an impressive collection of resort-style amenities. Families will appreciate the community's proximity to highly rated schools, while outdoor enthusiasts will love the direct access to Johns Lake, complete with a kayak launch & dock. Lakeview Preserve offers convenient access to shopping, dining, entertainment, & outdoor recreation. Historic Downtown Winter Garden is approx. 8 miles away, while Winter Garden Village is less than 7 miles from the community. With easy access to State Road 50, 27 & the 429 Expy, residents enjoy convenient travel throughout Central Florida, including our world-famous attractions such as Walt Disney & Universal. Golf enthusiasts will appreciate the proximity to at least 4 major golf properties. For those who love walking, jogging, or cycling, the scenic 22-mile West Orange Trail is just 15 mins away. Combining modern upgrades, an open-concept design, resort-style amenities, & a prime Winter Garden location, this home offers the low-maintenance lifestyle you've been looking for! Don't miss this incredible opportunity, schedule your private showing today & discover why so many residents are proud to call Lakeview Preserve home!

4540 Gliding Wave Street, Winter Garden
7747 Green Mountain Way, Winter Garden
$2,400,000
6 Beds ⋅ 7 Baths ⋅ Summerlake Pd Ph 3a SubDv. ⋅ 34787 Zip Code
Welcome to an exceptional waterfront residence on beautiful Lake Hancock in Winter Garden. Offering over 5,100 square feet of living space, this impressive 6-bedroom, 6.5-bath home features a 3-car garage and direct lake frontage. Designed for both everyday comfort and effortless entertaining, the home welcomes you with a dramatic two-story family room, expansive living areas, and two primary suites—one conveniently located on each level. At the heart of the home, the gourmet kitchen features granite countertops, an oversized curved island, double ovens, a cooktop, and an open dining area ideal for gathering with family and friends. Upstairs, additional bedrooms and a generous game room provide exceptional flexibility for family, guests, a media space, or recreation. Step outside to the screened lanai, complete with a summer kitchen, and take in the serene views of Lake Hancock. In the evenings, enjoy views of Disney’s fireworks from the comfort of your own home—an unforgettable touch to this exceptional Florida lifestyle. With generous indoor and outdoor living spaces and a remarkable waterfront setting, this Winter Garden home offers an ideal combination of space, comfort, and lakefront living. Schedule your private showing today and experience it for yourself.

7747 Green Mountain Way, Winter Garden
2548 Balforn Tower Way, Winter Garden
$449,900
3 Beds ⋅ 2 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code
Welcome home to this single-story 4-bedroom, 2-bath residence in Stoneybrook West, Winter Garden's 24-hour guard-gated golf community. Built in 2008 with solid block construction, the home offers 1,825 square feet of comfortable living space and an attached 2-car garage. Residents enjoy resort-style amenities including a clubhouse, junior Olympic-size pool with splash pad, fitness center, tennis and basketball courts, playgrounds, and walking trails, plus a championship golf course and private access to Black Lake. The home has been professionally prepared for move-in, with all locks rekeyed and the irrigation system checked and set. Enjoy quick access to SR 429 for easy commutes toward Walt Disney World, I-4, and Florida's Turnpike, with shopping and dining at Stoneybrook West Village and Winter Garden Village just minutes away.

2548 Balforn Tower Way, Winter Garden
16283 Honey Harvest Street, Winter Garden
$635,000
4 Beds ⋅ 5 Baths ⋅ Harvest/Ovation SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful 2024-built home in the desirable Harvest at Ovation community of Winter Garden! Thoughtfully designed with a bright, open-concept floor plan, this home offers modern finishes, abundant natural light, and flexible spaces for everyday living and entertaining. The first floor features a dedicated office along with a private bedroom suite complete with its own en suite bathroom, ideal for guests or those seeking additional privacy. Upstairs, you’ll find the spacious primary suite along with two additional bedrooms. A standout feature is the private space located above the garage. This spacious, open-layout area features a full bathroom and kitchenette area with a sink and space for a mini refrigerator, creating a versatile space that can be used as a guest retreat, game room, studio, home office, or additional living area. Harvest at Ovation offers thoughtfully designed community amenities, including a pool with cabana, butterfly garden, nature play space, dog park, and walking trails. Conveniently located near shopping, dining, entertainment, and major roadways, this home combines a flexible floor plan with the lifestyle and conveniences of Winter Garden and Horizon West. Schedule your private showing today!

16283 Honey Harvest Street, Winter Garden
15375 Avenue Of The Arbors, Winter Garden
$449,900
3 Beds ⋅ 3 Baths ⋅ Signature Lakes, Independence SubDv. ⋅ 34787 Zip Code
Virtually Staged. Fresh finishes, room to spread out, and a private outdoor retreat make this 3-bedroom, 2.5-bath end-unit townhome a standout in Winter Garden’s Independence community. With only one adjoining neighbor, the end-unit setting offers added privacy and a more open feel. Freshly painted interiors, stylish accent walls, and a two-car garage bring together personality, comfort, and everyday convenience. Laminate flooring flows throughout the main level, where a dedicated living room and a separate, extended family room give you the flexibility to entertain, unwind, or create distinct spaces for your daily routine. A dedicated dining area provides room for shared meals, while the fully equipped kitchen features matching stainless steel appliances, a beautiful backsplash, and an island with breakfast-bar seating for casual dining and conversation. The freshly painted bedrooms feature brand-new carpeting, giving these personal spaces a crisp, barely-touched feel. Thoughtful wall accents add character, while the primary suite includes a bathroom with a glass-enclosed shower. An included washer and dryer make settling into your new home even easier. Outside, a spacious screened-in lanai invites you to enjoy morning coffee, relaxed evenings, and gatherings in your own private setting. Vinyl fencing surrounds the outdoor retreat, and direct access from the garage adds a convenient connection between parking and your backyard escape. Life in Independence extends well beyond your front door. This welcoming, activity-filled community offers two resort-style pools, two residents clubs with fitness centers, tennis and basketball courts, an arcade and game room, playgrounds, parks, walking and biking trails, and boat ramps serving Lake Hancock and Lake Speer. Seasonal festivals, food truck events, and organized neighborhood activities create plenty of opportunities to connect and enjoy the community. Enjoy access to shopping and dining at Winter Garden Village, the charm of downtown Winter Garden, recreation along the West Orange Trail, and the attractions of Walt Disney World—all within a drive of home. With fresh updates, versatile gathering spaces, and an inviting outdoor retreat, this townhome offers a compelling opportunity to make Independence your next address. Schedule your private showing today.

15375 Avenue Of The Arbors, Winter Garden
1021 Huntspoint Street, Winter Garden
$865,000
4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to exceptional living in OAKLAND PARK, a Parade of Homes-winning community, where thoughtful design, extensive upgrades (~145K), & modern conveniences come together in this beautifully enhanced home. This FENCED home features 4 bedrooms, 3 en-suite baths, a remodeled half bath, dining space, loft, a screened-in balcony, TILE flooring, & a newer AC (2024), offering an ideal layout for everyday living & entertaining. The downstairs room is especially impressive, enhanced with stunning doors that beautifully frame the space, a Murphy bed with built-in storage, & its own private patio—perfect for guests, multigenerational living, or home office. The thoughtfully designed kitchen is both stylish & highly functional, with all kitchen appliances updated within the last few years with the exception of the cooktop & hood. Kitchen features a Bosch dishwasher, LG ThinQ refrigerator, built-in oven & microwave, QUARTZ counters, tile backsplash, a water filtration system, and an enhanced island customized with wood trim. Adjacent to the kitchen, you'll find two pantries, a built-in desk, & additional storage beneath the staircase. An electric FIREPLACE accented by custom shiplap creates a warm & inviting focal point in the living area. Custom walls add character & sophistication, including a striking board & batten design in the primary bedroom, a shiplap wall in the spare bedroom, & a custom wall along the staircase. PLANTATION SHUTTERS & updated lighting add both style & functionality. Custom closet systems are featured in all three bedrooms, along with two linen closets, the pantry, & the closet opposite the pantry. Additional cabinetry has been added to the laundry room, complete with a convenient drying rack. The upstairs bedrooms each feature their own en-suite bath, providing privacy & convenience, while one bedroom enjoys access to a screened-in balcony. The garage is a standout feature of its own, offering a dedicated mini-split AC, EV charger, epoxy flooring, abundant storage, & overhead storage that lowers for easy access. The house & garage are connected by a covered walkway, a rarity to the neighborhood. A truly exceptional bonus is the premium SOLAR & whole-home battery backup system (installed 2024), representing an 86K investment that will be PAID OFF at CLOSING. The 12.64 kW system includes 32 Mission Solar panels & four Enphase IQ Battery 5P units, providing approximately 20 kWh of battery storage. The system is designed to provide substantial backup power during outages & can keep virtually the entire home powered under normal household use. Enjoy a low monthly energy bill of ~$35! Just a short GOLF CART ride away, you’ll find the charm and vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, connection, & the unmatched charm of Winter Garden living. This golf-cart friendly WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails, including access to the 22 mile long WEST ORANGE TRAIL. Don’t miss this opportunity to live in one of the area's most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks!

1021 Huntspoint Street, Winter Garden
14501 Grove Resort Avenue Unit 2219, Winter Garden
$269,000
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code
Welcome to Unit 2219 at The Grove Resort & Water Park Orlando, where resort-style living meets an exceptional ownership opportunity just minutes from Central Florida’s world-famous attractions. This beautifully appointed 3-bedroom, 2-bath residence comes fully furnished and ready to enjoy. The spacious open-concept layout provides plenty of room for owners and guests, while the private balcony overlooking a peaceful water view creates the perfect setting to relax after a day enjoying everything Orlando has to experience. The primary suite features a spacious bathroom with a separate walk-in shower and soaking tub, offering the comfort and convenience expected from a full-service resort residence. Owners have access to The Grove’s extensive resort-style amenities, including water attractions, multiple swimming pools, dining options, fitness facilities, spa services, recreational areas, and much more. For owners seeking a hands-off approach, The Grove offers an optional professional resort management and rental program, providing the convenience of having the property managed and rented when not being personally enjoyed. Whether you are looking for a Florida vacation home, a furnished resort property, or an investment opportunity with professional management available, Unit 2219 offers a unique combination of comfort, convenience, and resort amenities in the Orlando area.

14501 Grove Resort Avenue Unit 2219, Winter Garden
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