Winter Garden Homes with Playground Community Features

Winter Garden Homes with Playground Community Features

Welcome to Winter Garden, Florida—a charming city that beautifully blends the warmth of small-town living with the vibrancy of modern amenities. Nestled just a short drive from the bustling attractions of Orlando, Winter Garden boasts a rich history that is reflected in its picturesque downtown area, complete with brick-lined streets, delightful boutiques, and a variety of dining options. The city is surrounded by lush landscapes and scenic lakes, making it a perfect haven for outdoor enthusiasts and families alike.

One of the standout features of Winter Garden is its family-friendly atmosphere, particularly in communities that offer playground amenities. Homes with playground community features are designed with families in mind, providing safe and engaging spaces for children to play and explore. Imagine your little ones laughing and making friends just steps from your front door, while you enjoy the peace of mind that comes with a secure, welcoming environment.

These communities often feature well-maintained playgrounds, picnic areas, and walking trails, encouraging an active lifestyle and fostering a sense of community among residents. Whether you're hosting a family gathering or enjoying a quiet afternoon with your children, these amenities create an inviting atmosphere that enhances your living experience.

With its exceptional schools, vibrant community events, and proximity to major attractions, Winter Garden is not just a place to live—it's a place to thrive. Explore the homes available in this delightful city, and discover the perfect blend of comfort, convenience, and community for you and your family. Welcome home to Winter Garden!

Newest Winter Garden Homes with Playground Community Features

234 Woodfall Lane, Winter Garden
$1,219,170
5 Beds ⋅ 5 Baths ⋅ O6453589 MLS
Under Construction. Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. The new two-story Roseland home combines modern elegance with practical living, offering 5 bedrooms, an enclosed flex room, 4 full bathrooms, a powder room, and a 3-car garage. As you step through the double entry glass doors, you are immediately greeted by a striking foyer that rises to the second floor, setting the tone for the entire home. To one side, a spare bedroom en suite offers privacy for guests and loved ones on the first floor, while the formal dining room invites effortless entertaining. From there, you enter the heart of the home—a chef-inspired gourmet kitchen. Equipped with built-in KitchenAid stainless steel appliances, including double ovens, the kitchen is a dream for culinary enthusiasts. Soft-close cabinetry with clear glass uppers is paired with exquisite quartz countertops, creating a timeless and sophisticated look, while a spacious walk-in pantry ensures ample storage. The open-concept design effortlessly connects the kitchen to the gathering room and cafe, where soaring ceilings create an airy, light-filled space, perfect for both intimate gatherings and larger celebrations. The covered lanai offers a seamless transition to the outdoors, ideal for year-round entertaining. Also located on the first floor, is a “Multi-Gen Suite” offering a spacious bedroom with its own linen closet, walk-in closet, and attached bathroom complete with a glass enclosed shower and quartz countertops. Upstairs, the private owner’s suite spans one side of the home, creating a peaceful retreat. The owner’s retreat area, ideal for reading or unwinding, leads into the spa-inspired owner’s bath, where luxury knows no bounds. A frameless glass-enclosed shower, free standing tub, enclosed toilet, and double walk-in closets create a sanctuary of relaxation. The second floor also offers two additional spacious bedrooms connected by a Jack and Jill bathroom, ensuring both privacy and convenience, while a third bedroom enjoys its own en suite bath, providing an added level of comfort and luxury. The upstairs laundry room, with a utility sink and a brand new Whirlpool washer and dryer makes daily tasks a breeze. With an intelligently designed layout and meticulously curated finishes, this home offers the perfect balance of form, function, and style. It's the epitome of luxury living in a highly sought-after location, blending convenience, sophistication, and thoughtful design into a living experience like no other. Schedule a tour today!

234 Woodfall Lane, Winter Garden

14026 Frasier Street, Winter Garden
$464,900
3 Beds ⋅ 3 Baths ⋅ O6451346 MLS ⋅ Meritage Homes BLDG.
SELLER OFFERING $10,000 TOWARDS BUYER CLOSING COST WITH AN ACCEPTABLE OFFER!! Welcome to this beautiful 2023-built home in the desirable Highland Ridge community of Winter Garden! Featuring 3 bedrooms, 2.5 bathrooms, and 1,985 square feet of thoughtfully designed living space, this home offers the perfect combination of modern comfort, functionality, and energy efficiency. Step inside and discover a bright, spacious open-concept main floor, ideal for everyday living and entertaining. The inviting covered front porch adds charm and provides a wonderful place to relax and enjoy the Florida lifestyle. Upstairs, you’ll find a versatile loft perfect for gathering and relaxation, along with a private primary suite offering comfort and privacy. The additional bedrooms provide flexibility for family members or guests. Built by Meritage Homes, known for its innovative energy-efficient features, this property is designed with comfort and potential energy savings in mind. Additional highlights include a two-car garage and access to the community pool. Location is another outstanding feature! Just a short walk from the new Ovation Elementary School and the Flamingo Crossings shopping center, offering a variety of restaurants, fast-casual dining options, grocery stores, a fitness center, and convenience stores, making everyday living exceptionally convenient. The property also provides easy access to major roadways and Orlando’s world-famous attractions. Don’t miss your chance to own a nearly new home in one of the Orlando area’s most desirable locations. Schedule your private showing today!

14026 Frasier Street, Winter Garden

6707 Marmalade Alley, Winter Garden
$480,000
4 Beds ⋅ 4 Baths ⋅ O6452928 MLS ⋅ 1 BLDG.
Virtually Staged. Virtually Staged. Welcome to modern living in the heart of Winter Garden! This beautifully upgraded 4-bedroom, 3.5-bath corner-unit townhome offers a spacious, thoughtfully designed floor plan with the primary suite conveniently located on the main level, featuring a beautiful shiplap accent wall, updated shower, custom closet organization, and French doors opening to the inviting front porch. Upstairs, you'll find three carpeted bedrooms, including a private ensuite, along with a versatile loft featuring laminate flooring. The kitchen boasts stainless steel appliances, granite countertops, and a stylish backsplash, opening to inviting living and dining spaces accented by beautiful wood beams and upgraded lighting. Additional enhancements throughout the home include upgraded interior doors, a water softener, and thoughtful storage solutions. Step outside to your own private retreat featuring an extended, fully paved and fenced courtyard with sealed pavers, ideal for entertaining, relaxing, or enjoying Florida evenings. The detached garage has a covered walkway to the home. Located in the desirable Hamlin Reserve community in Horizon West, this home offers convenient access to Hamlin Town Center, shopping, dining, entertainment, and everyday essentials. Enjoy nearby parks, walking trails, and outdoor recreation, with easy access to SR-429 and a short drive to Walt Disney World and Central Florida's world-class attractions. A wonderful opportunity to enjoy modern living, exceptional outdoor space, and a convenient Winter Garden location!

6707 Marmalade Alley, Winter Garden

2139 Tillman Avenue, Winter Garden
$825,000
4 Beds ⋅ 4 Baths ⋅ S5160111 MLS
STOP YOUR SCROLL!!! It's not everyday a GORGEOUS home inside the beautiful gated community of Bronson's Landing is available but this Pool Home offers SO MUCH! This 4 bedroom PLUS OFFICE and POSSIBLE 5th BEDROOM home has 4 FULL bathrooms with multiple living spaces, multiple dining areas as well as an extra large 3 car garage. At the heart of the home is the spacious kitchen with an island, perfectly positioned between the main living areas and designed for both everyday life and entertaining. You’ll find granite counter tops, a large center island, double ovens, plenty of cabinetry, and a pantry. One of the best features is that the primary suite and three additional bedrooms are all located on the main floor. The primary bedroom feels like its own private retreat on it's own side of the house with two walk-in closets, dual vanities, a soaking tub, and separate shower. Being a split floor plan, 2 bedrooms share a Jack-and-Jill bathroom that makes this home super functional. This home can easily handle generational living. Upstairs, the over-sized bonus room with its own full bathroom gives you even more possibilities. Use it as a game room, movie room, guest suite, home gym, second office, or even a possible 5th bedroom. There is plenty of flexibility to make the space work for your lifestyle. The backyard is where the Florida lifestyle really shines! Step outside to your own private oasis with a screened saltwater pool, covered lanai, paver deck, and convenient pool bath. The home backs to a beautiful tree-lined green space, giving you extra privacy and a peaceful setting with no home directly behind you. Imagine starting the morning with coffee by the pool, spending the afternoon soaking up the Florida sunshine, and ending the evening relaxing under the lanai. And YES! Location matters! Bronson’s Landing is a sought-after gated community in one of Winter Garden’s most desirable areas, with access to highly regarded schools and an amazing Central Florida location. You’re close to Winter Garden Village, shopping, dining, 429, and all the charm of Historic Downtown Winter Garden. ALSO! Walt Disney World is just a short drive away, making spontaneous trips to the parks, dinner at Disney Springs, or a night watching fireworks that much easier! This home gives you the space of a true family home, the privacy of a beautiful gated community, your own Florida pool, and easy access to everything that makes Winter Garden and the Disney area such a MAGICAL place to live. If you’ve been waiting for a home that offers space, flexibility, privacy with a pool, and a fantastic location, THIS IS THE ONE!

2139 Tillman Avenue, Winter Garden

5705 New Independence Parkway, Winter Garden
$399,900
3 Beds ⋅ 2 Baths ⋅ O6452416 MLS ⋅ 5705 BLDG.
WELCOME HOME TO 5705 NEW INDEPENDENCE PARKWAY! Discover the perfect blend of COMFORT, CHARM, and RESORT-STYLE LIVING in the highly desirable INDEPENDENCE / SIGNATURE LAKES COMMUNITY of WINTER GARDEN, FLORIDA! This inviting 3-BEDROOM, 2.5-BATH TOWNHOME offers 1,751 SQ. FT. OF LIVING SPACE, a PRIVATE REAR-ENTRY 2-CAR GARAGE, and a wonderful opportunity to enjoy everything that makes Central Florida living so special. From the moment you arrive, the CHARMING FRONT PORCH welcomes you home. Step inside to discover a bright, OPEN-CONCEPT FLOOR PLAN filled with NATURAL LIGHT, creating a comfortable setting for everyday living, entertaining friends, or simply unwinding after a long day. The SPACIOUS KITCHEN features GRANITE COUNTERTOPS, generous cabinet storage, and plenty of room to gather, while UPDATED LAMINATE FLOORING adds warmth throughout the main living areas. A NEWER HVAC SYSTEM INSTALLED IN 2025 provides an added touch of comfort and peace of mind. Upstairs, the PRIMARY SUITE offers a relaxing retreat with a PRIVATE ENSUITE BATHROOM and WALK-IN CLOSET. Two additional bedrooms provide flexible space for guests, hobbies, or a HOME OFFICE. Whether you're enjoying your morning coffee on the FRONT PORCH, hosting dinner with loved ones, or relaxing on the PRIVATE PATIO, this home offers room to create lasting memories. Life in INDEPENDENCE is about so much more than the home itself! Residents enjoy an exceptional collection of RESORT-STYLE AMENITIES, including TWO COMMUNITY POOLS, FITNESS CENTERS, a CLUBHOUSE, PARKS, PLAYGROUNDS, DOG PARKS, TENNIS AND BASKETBALL COURTS, SCENIC WALKING TRAILS, and COMMUNITY LAKE ACCESS. Neighborhood gatherings and community events create opportunities to connect, unwind, and truly feel at home. And the LOCATION is equally impressive! Nestled in the heart of HORIZON WEST, you're conveniently located near HAMLIN TOWN CENTER, HISTORIC DOWNTOWN WINTER GARDEN, the WEST ORANGE TRAIL, and WALT DISNEY WORLD, with easy access to shopping, dining, entertainment, major roadways, and area schools. LOCATION, COMFORT, COMMUNITY, AND RESORT-STYLE LIVING — ALL IN ONE PLACE! With 3 BEDROOMS, 2.5 BATHROOMS, 1,751 SQ. FT., A PRIVATE 2-CAR GARAGE, and an incredible array of NEIGHBORHOOD AMENITIES, 5705 NEW INDEPENDENCE PARKWAY is more than just a place to live — it's a place to feel at HOME. WELCOME HOME TO INDEPENDENCE, WINTER GARDEN!

5705 New Independence Parkway, Winter Garden

5513 New Independence Parkway, Winter Garden
$575,000
3 Beds ⋅ 2 Baths ⋅ O6452296 MLS
Nestled in the heart of the desirable Winter Garden, this beautifully updated 3-bedroom, 2-bathroom SALTWATER POOL HOME offers 1,920 square feet of thoughtfully designed living space, modern elegance, and an exceptional resort-style lifestyle! From the moment you arrive, you’ll fall in love with the picturesque curb appeal, lush landscaping, charming brick-paver walkway, and inviting covered front porch. Step inside to discover a bright, open-concept floor plan featuring beautiful bamboo flooring, abundant natural light, and inviting living spaces perfect for everyday comfort and entertaining. The heart of the home is the stunning kitchen, completely remodeled in 2019! Featuring gorgeous quartz countertops, rich cabinetry, stainless steel appliances, stylish pendant lighting, and an expansive island with seating, this space is designed for gathering and making memories. A charming, sun-filled dining nook completes the picture! Your own private backyard oasis awaits! Step through beautiful French doors to your sparkling SALTWATER POOL, surrounded by an expansive screened enclosure and spacious covered lanai. Whether you're enjoying a refreshing afternoon swim, hosting weekend gatherings, or relaxing in the shade, this outdoor retreat makes every day feel like a vacation! Additional highlights include a convenient rear-entry garage with a beautifully finished epoxy floor. The lifestyle doesn't stop at your front door! Enjoy RESORT-STYLE COMMUNITY AMENITIES and a vibrant calendar of year-round events, including themed movie nights, ice cream socials, fireworks, and seasonal celebrations. Even better, the HOA includes internet and cable. Ideally located in the beautiful Winter Garden, walkable to schools, shopping, dining, entertainment, and conveniently located to Central Florida attractions, this home offers the perfect blend of modern comfort, neighborhood charm, and Florida living. More than a home....it's a lifestyle! Schedule your private showing today! *Wine fridge and weather station on the lanai screen does not convey.

5513 New Independence Parkway, Winter Garden

11947 Shine View Lane, Winter Garden
$942,596
5 Beds ⋅ 5 Baths ⋅ O6452353 MLS
Under Construction. Waterleigh presents the Torrey. A two-story all concrete block construction single-family home features 5 bedrooms and 4.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room and butler’s pantry. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai that looks over a pond. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Located off the family room is a bedroom and a full bathroom. As we head up to the second floor, we are greeted with a loft area and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Like all homes in Waterleigh, the Torrey includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11947 Shine View Lane, Winter Garden

13006 Serene Glade Road, Winter Garden
$498,900
3 Beds ⋅ 3 Baths ⋅ S5160084 MLS
Winter Garden, Florida | Former Model Home | 3 Bedrooms | 2.5 Bathrooms FORMER MODEL HOME • DESIGNER UPGRADES • WINTER GARDEN THIS ONE WILL GET YOUR BUYERS’ ATTENTION! Welcome to 13006 Serenade Glade, an exceptional 3-bedroom, 2.5-bath former model home where luxury, style, and thoughtful upgrades come together beautifully. This is not your typical resale! Built to impress and showcased as a model, this home features extensive upgrades, elevated finishes, designer details, and a beautifully appointed interior that immediately stands out from the competition. The open and inviting floor plan offers an effortless flow for entertaining, while the spacious living areas create the perfect combination of comfort and sophistication. The kitchen is a true focal point, complemented by upgraded finishes and a seamless connection to the living and dining spaces. The primary suite offers a private retreat, while the additional bedrooms provide excellent flexibility for guests, family, or a home office. Every detail was selected to make this home stand out—and it shows. From the upgraded flooring and lighting to the enhanced fixtures and finishes, this former model home delivers the polished look buyers are searching for without the hassle or expense of doing the upgrades themselves. Located in desirable Winter Garden, this is a fantastic opportunity for buyers looking for a home that feels special from the moment they walk through the door. FORMER MODEL HOME • 3 BEDROOMS • 2.5 BATHROOMS EXTENSIVELY UPGRADED • DESIGNER FINISHES • MOVE-IN READY Bring your buyers—this is one they’ll remember

13006 Serene Glade Road, Winter Garden

8943 Lakeshore Pointe Drive, Winter Garden
$639,900
3 Beds ⋅ 3 Baths ⋅ OM734569 MLS ⋅ Na BLDG.
ONE OF THE PRETTIEST LOCATIONS AND VIEWS IN LAKESHORE!! SHOWS BETTER THAN A MODEL WITH TOO MANY UPGRADES TO LIST!!! LOCATION, LOCATION, LOCATION!!! FROM THE TIME YOU ARRIVE, YOU WILL IMMEDIATELY FALL IN LOVE WITH THE OVERSIZED FRONT PORCH, WATERVIEW OF THE COMMUNITY FOUNTAIN, AND MORE THAN ENOUGH ROOM TO ENJOY OUTDOOR LIVING! THIS LUXURIOUS TOLL BROTHERS DANTE ITALIANATE FLOORPLAN HAS IT ALL! THIS HOME HAS AN OPEN CONCEPT WITH HIGH CEILINGS, LOTS OF WINDOWS ALLOWING FOR NATURAL LIGHT, HUGE SLIDING DOORS WHICH LEAD TO A PRIVATE BRICK PAVERED COURTYARD AND A COVERED WALKWAY TO YOUR TWO CAR GARAGE. WALK INTO YOUR SPACIOUS KITCHEN WHICH INCLUDES A MASSIVE ISLAND AND AN ADDITIONAL BREAKFAST BAR, BOTH WITH UPGRADED QUARTZ COUNTERTOPS. YOU WILL LOVE YOUR NEW KITCHEN WHICH INCLUDES AN UPGRADED CABINET PACKAGE ADDING ADDITIONAL CABINETS FOR AMPLE SPACE, 42" CABINETS, CROWN MOLDING, STAINLESS APPLIANCES AND NATURAL GAS FOR COOKING. MANY ENERGY SAVING FEATURES INCLUDING TANKLESS WATER HEATER, FOAM INSULATION, SOLID CONCRETE BLOCK WALLS FROM THE FOUNDATION THROUGH THE ATTIC AND MORE. ENJOY RESORT STYLE AMENITIES WHICH INCLUDE A POOL, FITNESS CENTER, CLUBHOUSE WITH BREATHTAKING LAKE AND GOLF COURSE VIEWS, KAYAK AND PADDLE BOARD LAUNCH, TWO PLAYGROUNDS, FIREPIT, SUMMER KITCHEN, HAMMOCKS AND DOG PARK. LAKESHORE PRESERVE IS LOCATED IN THE HAMLIN AREA, ONLY TEN MINUTES FROM MAJOR TOURIST ATTRACTIONS. YOU WILL ALSO FIND NEW SCHOOLS, NEW RESTAURANTS, NEW HOSPITAL, PLENTY OF SHOPPING AND ENJOY THE NEW CINEPOLIS RECENTLY BUILT - EASY ACCESS TO ALL THAT CENTRAL FLORIDA HAS!! SCHEDULE YOUR APPOINTMENT TODAY, YOU WILL NOT BE DISAPPOINTED!!!

8943 Lakeshore Pointe Drive, Winter Garden

5685 New Independence Parkway, Winter Garden
$464,999
3 Beds ⋅ 3 Baths ⋅ O6452105 MLS ⋅ 5685 BLDG.
INDEPENDENCE Community! This END unit is nothing like you have ever seen in the neighborhood before!! Offering stylish finishes, thoughtful improvements, and an exceptional location, this MOVE IN READY home is the perfect blend of comfort, functionality, and modern living. EXTENSIVELY UPDATED!! This home features a freshly painted exterior and interior (2024), updated trim, new 6-inch baseboards, 3-inch door casings, and upgraded lighting, ceiling fans, and fixtures throughout (2024). In 2023, the home received luxury vinyl plank flooring on the main level and in the upstairs bathrooms, a fully remodeled kitchen, an updated laundry area, and a new water heater. The high-efficiency TRANE 20-SEER A/C system (2020) adds year-round comfort and efficiency. Luxury Vinyl Plank flooring added to the stairs and upstairs this year! (2026) NO CARPET!! New refrigerator (2026!) The stunning remodeled kitchen is the heart of the home, featuring quartz countertops, solid wood cabinetry with soft-close drawers and crown molding, a farmhouse sink, a walk-in pantry, and an oversized island complete with a wine fridge. Stainless steel appliances complete this stylish and functional space, offering plenty of storage and room to gather. The open-concept layout flows seamlessly into the dining area and spacious living room, where abundant natural light creates a warm and inviting atmosphere. A convenient half bath on the main level adds to the home's everyday functionality.Upstairs, you'll find three comfortable bedrooms and two upgraded bathrooms featuring refreshed vanities, new mirrors, updated lighting, and comfort-height, skirted self-cleaning toilets. Outside, enjoy the added privacy and curb appeal of this end-unit townhome, complete with a covered front porch, block and stucco construction extending to the roof, and a two-car rear-facing garage with additional ceiling storage installed in 2021. The outdoor living space is just as inviting, featuring a private, fenced paver patio with green space beyond the fence—perfect for morning coffee, relaxing evenings, or entertaining guests. Additional improvements include all-new appliances (2021), new window screens and blinds (2021), a wired security system, and energy-efficient lighting throughout. Located in a highly rated A-rated school district, Independence offers desirable community amenities and a welcoming neighborhood atmosphere. Conveniently situated in the heart of Winter Garden/Horizon West, you'll enjoy easy access to shopping, dining, entertainment, theme parks, SR-429, and other major roadways. With extensive updates, modern finishes, added privacy, and an outstanding location, this beautifully maintained townhome is ready for its next owner. Don't miss your opportunity to make this exceptional property your own—schedule your private showing today!

5685 New Independence Parkway, Winter Garden

Start Your Search

How much is your home worth?

Get instant property value now!