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 historic downtown, Winter Garden boasts a delightful blend of small-town charm and modern conveniences. With its picturesque streets lined with boutiques, cafes, and farmers markets, this community is perfect for those who appreciate a leisurely lifestyle infused with local culture.

One of Winter Garden's standout features is its commitment to family-friendly living. Many neighborhoods in the area are designed with community in mind, offering homes that come with playgrounds and recreational spaces. Imagine your children laughing and playing just steps from your front door, surrounded by friendly neighbors and a safe environment. These playground community features not only provide a space for children to explore and enjoy the outdoors but also create a vibrant social hub for families to connect and build lasting friendships.

In addition to its family-oriented amenities, Winter Garden is conveniently located near major highways, making it easy to access the bustling attractions of Orlando while still enjoying the tranquility of suburban life. With year-round sunshine, beautiful parks, and a calendar full of community events, Winter Garden is more than just a place to live; it’s a place to thrive.

Whether you’re looking for a cozy single-family home or a spacious property with room to grow, Winter Garden offers a variety of housing options that cater to every lifestyle. Come and discover why Winter Garden is the perfect place to call home!

Newest Winter Garden Homes with Playground Community Features

14230 Sunridge Boulevard, Winter Garden
$629,900
3 Beds ⋅ 2 Baths ⋅ Cypress Reserve Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained home in desirable Winter Garden, where comfort, style, and functionality come together! From the spacious front porch to the impressive 8-foot glass front door, this inviting home offers thoughtful upgrades and generous living spaces throughout. The elegant formal dining room features a tray ceiling and beautiful wooden plantation shutters, creating the perfect setting for special gatherings. The open-concept kitchen is a standout, featuring quartz countertops, a stylish tile backsplash, a center island with a deep sink, chrome faucet, pendant lighting, stainless steel appliances, a convenient butler's pantry, and a cozy breakfast nook. The spacious living room is equally impressive, showcasing an electric fireplace with a decorative mantel, recessed lighting, and double sliding glass doors that seamlessly connect indoor and outdoor living. Step outside to the expansive, custom-built, covered and screened patio, overlooking a fully fenced backyard, an ideal setting for entertaining guests, outdoor dining, or simply relaxing in privacy. Additional highlights include brand-new carpeting in all bedrooms and a professionally cleaned interior, making this home move-in ready! Residents enjoy a community swimming pool and a playground. Conveniently located near the popular Tucker Ranch Recreation and Nature Complex, with easy access to shopping, dining, and outdoor recreation, this home offers an exceptional combination of location, comfort, and lifestyle. Don't miss this wonderful opportunity to make this Winter Garden home your own. Schedule your private showing today!

14230 Sunridge Boulevard, Winter Garden

14501 Grove Resort Avenue Unit 1528, Winter Garden
$215,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo I SubDv. ⋅ 34787 Zip Code
MOTIVATED SELLER... BRING OFFER! Welcome to a beautifully appointed 3-bedroom luxury condo-hotel residence at The Grove Resort & Water Park, offering exceptional views, a spacious layout, and true turnkey ownership just minutes from Disney and the Orlando theme parks. This well-designed unit features a generous open-concept living and dining area, ideal for entertaining or relaxing after a day at the parks. The thoughtfully separated bedroom layout provides comfort and privacy for owners and guests alike, making it especially attractive for short-term rentals. Offered fully equipped for immediate use, this residence is designed to perform as both a personal vacation retreat and an income-producing investment. Beyond the residence, owners and guests enjoy access to one of Central Florida’s most amenity-rich resorts. The Grove Resort & Water Park features a full-scale water park with lazy river and water slides, multiple resort-style pools, a surf simulator, full-service spa, fitness center, on-site shopping, and a variety of restaurants with indoor and outdoor dining. The resort also includes Lake Austin for fishing and paddle boating, conference and event facilities, and complimentary shuttles to Disney. The property is supported by a professional, on-site management team, providing a seamless and hands-off ownership experience while maintaining high guest satisfaction. This unique condo-hotel opportunity allows owners to enjoy personal use while generating rental income when not in residence. A rare combination of space, views, resort amenities, and location, this unit stands out among competing offerings—ideal for buyers seeking flexibility, lifestyle, and long-term value in a premier destination.

14501 Grove Resort Avenue Unit 1528, Winter Garden

16773 Broadwater Avenue, Winter Garden
$2,575,000
7 Beds ⋅ 6 Baths ⋅ Waterside On Johns Lake SubDv. ⋅ 34787 Zip Code
Experience the ultimate in luxury lakefront living in this exceptional 7-bedroom Mansfield floor plan, offered for sale for the first time by its original owner. Perfectly positioned along nearly 100 feet of shoreline on the spectacular 2,600-acre Johns Lake, this remarkable residence offers approximately 6,300 heated square feet of thoughtfully designed living space, breathtaking panoramic water views, and a rare walkout basement ideal for multigenerational living. Impressive curb appeal and a welcoming courtyard entrance set the stage for soaring ceilings, expansive living areas, and unforgettable lake views from the moment you enter. The magnificent great room is flooded with natural Florida sunshine, featuring an electric fireplace and sweeping views of Johns Lake. The recently renovated gourmet kitchen is a showpiece, boasting an oversized center island, freestanding natural gas range, and separate full-size refrigerator and freezer. The main level features a luxurious owner's suite, dedicated home office, and additional ensuite bedroom. Upstairs, an expansive bonus room complements three generously sized bedrooms and two full bathrooms, providing exceptional flexibility for family and guests. What truly distinguishes this extraordinary lakefront estate is the enormous walkout basement, offering endless possibilities for a home theater, fitness center, entertainment lounge, game room, or custom bar. A SECOND OWNER'S SUITE provides an incredible opportunity for an in-law retreat, extended family accommodations, or private multigenerational living quarters. Thoughtful planning by the original owners includes future pool connections, natural gas stub-outs for additional coach lighting, preplumbing and gas connections for an outdoor summer kitchen, and numerous additional ceiling fan locations. Additional enhancements include plantation shutters, custom closets, and a whole-home natural gas backup generator. Step outside to an expansive backyard showcasing breathtaking 180-degree panoramic views of Johns Lake. Your private covered boat dock with low-maintenance composite decking and boat lift creates the ultimate waterfront lifestyle, with boating, fishing, watersports, and sunset cruises right from your backyard. Spanning Orange and Lake counties, Johns Lake is renowned for its expansive open waters, scenic shoreline, and exceptional fishing. Located within the gated community of Waterside on Johns Lake, residents enjoy resort-style amenities including a beautiful clubhouse, state-of-the-art fitness center, community swimming pool, and playground. This highly desirable Clermont and Winter Garden corridor offers access to sought-after K–12 schools & Foundation Academy, Montverde Academy, and Windermere Prep School. Ideally situated along Marsh Road, this exceptional location places you minutes from outstanding shopping, dining, and entertainment in both Clermont and Winter Garden. Enjoy convenient access to Walt Disney World, SR 429, SR 408, Florida's Turnpike, and Downtown Orlando. Historic Downtown Winter Garden is just minutes away, offering charming boutiques, acclaimed restaurants, the West Orange Trail, community festivals, and its famous Saturday Farmers Market. Combining extraordinary square footage, a rare walkout basement, dual owner's suites, private boating access, and nearly 100 feet of pristine Johns Lake frontage, this remarkable property delivers an unparalleled opportunity to embrace the Florida lakefront lifestyle.

16773 Broadwater Avenue, Winter Garden

9279 Grand Island Way, Winter Garden
$505,000
3 Beds ⋅ 3 Baths ⋅ Watermark Ph 2c SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to 9279 Grand Island Way, a beautifully appointed 3-bedroom, 2.5-bathroom residence situated on a desirable corner lot in the sought-after Watermark community of Horizon West in Winter Garden. Offering the perfect blend of modern style, comfort, and convenience, this recently painted two-story home features brand-new luxury vinyl flooring throughout the first floor and an inviting open-concept floor plan designed for both everyday living and effortless entertaining. Step inside to discover a bright and spacious living area filled with natural light, complemented by beautiful new luxury vinyl flooring and a modern kitchen featuring granite countertops, 42-inch cabinetry, stylish pendant lighting, and ample counter space. The kitchen flows seamlessly into the dining and living areas, creating an ideal setting for gatherings with family and friends. A convenient half bathroom and access to the two-car garage complete the first floor. Upstairs, a versatile loft provides additional living space, perfect for a home office, media room, playroom, or private lounge. The spacious primary suite offers a relaxing retreat with an en-suite bathroom and walk-in closet, while two additional bedrooms provide comfortable accommodations for family or guests. The home's desirable corner-lot location allows for abundant natural light, enhancing its open and welcoming atmosphere. One of the property's standout features is its exceptional location directly across from the Horizon West retail and dining center, placing everyday conveniences just moments from your doorstep. Enjoy easy access to Starbucks, New York Beer Project, Walgreens, and a variety of nearby shopping, dining, and entertainment options. The ability to walk or bike to neighborhood favorites adds to the appeal of this vibrant community. Residents of Watermark enjoy an impressive collection of resort-style amenities, including a community swimming pool with splash pad, clubhouse, fitness center, tennis courts, playgrounds, and scenic walking trails, offering recreation and relaxation just minutes from home. Ideally situated near Hamlin Town Center, Orange County National Golf Center, major roadways including SR 429, and Walt Disney World, this home provides convenient access to everything that makes Horizon West one of Central Florida's most desirable places to live. Experience the perfect combination of location, lifestyle, and modern comfort at 9279 Grand Island Way. Welcome home!

9279 Grand Island Way, Winter Garden

15066 Marbled Godwit Drive, Winter Garden
$535,000
3 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 4b SubDv. ⋅ 34787 Zip Code
WINTER GARDEN • HORIZON WEST • SUMMERLAKE • 3 BEDROOMS • 2.5 BATHS • APPROX. 2,156 SQ FT • OPEN-CONCEPT LAYOUT • SPACIOUS LOFT • FENCED BACKYARD • 2-CAR GARAGE • NATURAL GAS COMMUNITY • BUILT IN 2019. Welcome to 15066 Marbled Godwit Dr, a two-story home in the Summerlake community of Winter Garden, offering flexible living spaces and convenient access to the shopping, dining, recreation, and entertainment destinations of Horizon West. Positioned across from a community park, the home also provides convenient access to nearby green and recreational space. The main level features an open-concept layout connecting the kitchen, dining, and living areas. The kitchen offers a large center island, granite countertops, light-toned cabinetry, stainless steel appliances, and natural gas, providing generous workspace and a functional centerpiece for the main living area. Upstairs, a spacious loft adds valuable flexibility for a home office, media room, game room, fitness area, or additional lounge. The primary suite and two additional bedrooms are also located on the second level, creating practical separation between the main living areas and private spaces. Step outside to the lanai and fenced backyard, with space for outdoor seating, grilling, gardening, and relaxation. A long driveway leads to the attached 2-car garage, providing additional space for parking and storage. Summerlake is a natural gas community offering an extensive collection of amenities, including a clubhouse, resort-style pool, fitness center, tennis and basketball courts, playgrounds, parks, walking and biking paths, and scenic boardwalk connections surrounded by lakes and natural areas. The Horizon West location provides convenient access to Hamlin Town Center, with restaurants, coffee shops, shopping, grocery options, services, and entertainment. Winter Garden Village offers additional shopping and dining, while Historic Downtown Winter Garden features Plant Street Market, local restaurants and shops, the weekly farmers market, and access to the West Orange Trail. Orange County National Golf Center provides another nearby recreational destination. Convenient access to SR-429 connects Horizon West with additional Central Florida destinations, including Walt Disney World and the greater Orlando area. For buyers searching for a Winter Garden home in Horizon West with natural gas, an open-concept floor plan, spacious loft, fenced backyard, 2-car garage, clubhouse and resort-style community amenities, plus convenient access to Hamlin, shopping, dining, recreation, and entertainment, 15066 Marbled Godwit Dr brings these features together in one location. Schedule your private showing today and see what 15066 Marbled Godwit Dr has to offer!

15066 Marbled Godwit Drive, Winter Garden

9662 Waterway Passage Drive, Winter Garden
$515,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2a SubDv. ⋅ 34787 Zip Code
SELLER IS OFFERING 5K IN UPGRADE CONCESSIONS for whatever your heart desires. BEST Price in the neighborhood! Premium CORNER lot w/ community green space (play areas for the little ones). This is one of the few larger lots (7,809 sq ft) in the community. You won't find a better deal in Waterleigh! ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- This 3/2.5 + LOFT home is the perfect buy. You know the old saying, buy the smaller house in the big expensive neighborhood. Some neighbors' homes are valued at over a million dollars. Your property will benefit from the increasing value. Well, this is it. Offering 2,014 square feet of living space, it is the perfect size for a growing family without all the heavy cleaning! -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- As an added bonus, the HOA includes landscaping, allowing for truly low-maintenance living. Beyond the home itself, you'll fall in love with the incredible resort-style amenities this sought-after community has to offer, including multiple pools, fitness centers, tennis courts, sand volleyball court, mini golf course, playgrounds, scenic walking trails, community dock and a vibrant calendar of community events throughout the year. Everyday conveniences are just a golf cart ride away, including Publix, Jersey Mike's, a nail salon & Kiddie Academy. --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- This golf cart-friendly community was designed to make life easy, fun, and connected. Located in the highly desirable Horizon West area and zoned for Atwater Bay Elementary, you'll be just minutes from shopping, dining, entertainment, and outdoor recreation. Enjoy the charm of historic Downtown Winter Garden, the scenic West Orange Trail, and easy access to Orlando's world-famous attractions and theme parks. This home offers more than just beautiful living spaces, it offers a lifestyle. Why wait months to build when you can move right into a highly upgraded, turnkey home today?

9662 Waterway Passage Drive, Winter Garden

13618 Larsen Lane, Winter Garden
$888,000
4 Beds ⋅ 4 Baths ⋅ Glynwood Ii SubDv. ⋅ 34787 Zip Code
Virtually Staged. A true pride-of-ownership home showcasing architectural elegance, extensive upgrades, and the ultimate Florida lifestyle! Welcome to this stunning Winter Garden residence featuring a freshly painted exterior, tropical landscaping, paver driveway, and spacious three-car garage. Inside, soaring 13.5-foot ceilings, architectural arches, double-tiered tray ceilings, and a custom coffered family room ceiling create an impressive atmosphere. The gourmet kitchen features a sprawling granite island with prep sink, 42-inch solid wood cabinetry custom-painted in November 2025, premium GE Profile stainless steel appliances, a cooktop, double ovens, and a separate butler’s pantry ideal for entertaining or a coffee station. Enjoy seamless indoor-outdoor living through 16-foot, four-panel sliding pocket doors opening to a spacious brick-paver, screened lanai. Relax beneath the covered patio with flush-mounted speakers or beside the oversized saltwater pool with a new variable-speed pump installed in October 2025. The private quarter-acre backyard features mature privacy hedging and a convenient pool-access bathroom with a glass-enclosed walk-in shower. The main-level primary suite offers an elegant tray ceiling, a custom walk-in closet system installed in February 2026, and luxury linen and blackout window treatments. More than $100,000 in reported premium upgrades enhance comfort, efficiency, and peace of mind. Improvements include a 2-ton Daikin 15.6 SEER2 HVAC system (September 2025), upgraded R-38 attic insulation (September 2025), zoned 5-ton variable-speed Trane HVAC. Whole house hot water hybrid system: Tankless water heater fed by propane tank as a main source (electric tank can be used as a back-up). Aquasure Harmony whole-house water softener (August 2024), and a roof replaced in August 2016. Smart-home features include pre-wired 7.1 family room surround sound, multi-zone audio, window-tint film, security cameras with hybrid DVR, motion-activated lighting, smart front-door and garage locks, smart thermostats, and a Rachio irrigation controller. The gated subdivision adds another layer of appeal. Located in desirable Glynwood II at StoneCrest, residents enjoy a clubhouse, resort-style pool, playground, tennis courts, and scenic walking trails with pond views, a fountain, and green spaces. Conveniently close to Winter Garden Village, shopping, dining, parks, and the West Orange Trail, the community also offers access to major roadways, Orlando’s employment and entertainment centers, world-famous theme parks, Orlando International Airport, and Florida’s beautiful beaches. Experience exceptional architecture, modern technology, privacy, and effortless entertaining in this remarkable Winter Garden home! Note: The last four photos have been virtually staged.

13618 Larsen Lane, Winter Garden

3275 Buoy Circle, Winter Garden
$740,000
5 Beds ⋅ 5 Baths ⋅ Lakeview Preserve SubDv. ⋅ 34787 Zip Code
Virtually Staged. SPACIOUS LUXURY LIVING + 5 BEDROOMS + 4.5 BATHROOMS + 2 FLEX SPACES + GATED COMMUNITY! Welcome to this stunning YORKSHIRE MODEL in the highly desirable LAKEVIEW PRESERVE community of Winter Garden! Designed with space, comfort, and versatility in mind, this beautifully appointed home offers an exceptional floor plan ideal for MULTIGENERATIONAL LIVING, WORKING FROM HOME, AND ENTERTAINING. Featuring 5 generously sized bedrooms, 4 full bathrooms, a half bath, TWO FLEX SPACES—ONE ON EACH LEVEL, and an oversized lot with an open green backyard, there's room for everyone to spread out and enjoy! From the moment you enter, you'll appreciate the thoughtfully designed layout, 8-foot interior doors, abundant natural light, and stylish designer finishes. The OPEN-CONCEPT FLOOR PLAN flows seamlessly from the spacious gathering room into the dining area and GOURMET KITCHEN, featuring QUARTZ COUNTERTOPS, 42-INCH SOFT-CLOSE CABINETRY, BUILT-IN APPLIANCES, a decorative wood canopy hood, designer tile backsplash, oversized center island, and walk-in pantry. Expansive POCKET SLIDING GLASS DOORS open to the impressive 22-FOOT COVERED LANAI, NOW SCREENED IN BY THE CURRENT OWNERS, creating the perfect setting for indoor-outdoor entertaining while overlooking the spacious backyard. One of this home's greatest advantages is its FLEXIBLE, MULTIGENERATIONAL-FRIENDLY FLOOR PLAN. The FIRST-FLOOR GUEST SUITE WITH PRIVATE EN-SUITE BATHROOM AND WALK-IN CLOSET provides an ideal retreat for extended family, overnight guests, or anyone seeking additional privacy. A versatile FIRST-FLOOR FLEX SPACE offers the perfect opportunity for a home office, playroom, or additional living area. Upstairs, a SECOND SPACIOUS FLEX SPACE provides even more possibilities for a media room, game room, study area, or separate gathering area, allowing everyone to enjoy their own space. The upstairs PRIMARY SUITE is a relaxing private retreat featuring a large walk-in closet and a beautifully appointed en-suite bathroom with DUAL QUARTZ-TOPPED VANITIES, AN OVERSIZED WALK-IN SHOWER, and a private water closet. Three additional upstairs bedrooms, including one with its own EN-SUITE BATHROOM, offer comfortable accommodations and generous closet space. The upgraded laundry room adds convenience with cabinetry, quartz countertops, and a utility sink. Additional highlights include PORCELAIN TILE FLOORING throughout the main first-floor living areas, designer bathroom finishes, ample storage throughout, outdoor kitchen pre-plumbing, and a 2-CAR GARAGE WITH NEWLY ADDED EPOXY FLOORING for a clean, finished look. Located within the sought-after GATED COMMUNITY OF LAKEVIEW PRESERVE, residents enjoy RESORT-STYLE AMENITIES, including a sparkling pool with splash pad, clubhouse, fitness center, playground, picnic areas, and KAYAK LAUNCH WITH ACCESS TO JOHNS LAKE. Even better, the community has NO CDD FEE! Just approximately 5 miles from charming DOWNTOWN WINTER GARDEN and minutes from SR 429, you'll enjoy convenient access to shopping, dining, entertainment, and major Central Florida roadways. Experience the space, flexibility, and lifestyle this exceptional Winter Garden home has to offer. Schedule your private showing today!

3275 Buoy Circle, Winter Garden

2199 White Feather Loop, Oakland
$489,900
3 Beds ⋅ 3 Baths ⋅ Oakland Trails Ph 1 SubDv. ⋅ 34787 Zip Code
Stunning 3-bedroom, 2.5-bath bungalow nestled in the highly desirable community of Oakland, offering picturesque views of the community park, lush green spaces, and direct access to local walking trails. Built in 2018 and impeccably maintained, this home features an open-concept layout with towering 10-foot ceilings throughout. The main level boasts gorgeous tile flooring, a built-in office desk, a convenient wet bar, and carefully curated interior lighting that enhances the home's warm character and sophisticated ambiance. The gourmet kitchen shines with 42-inch refinished maple cabinets, updated hardware, quartz countertops, a stunning center quartz island, and a striking ceiling-height marble backsplash. Upstairs, enjoy the warmth of bamboo stairs and beautiful bamboo flooring across all bedrooms, each equipped with walk-in closets. Additional notable upgrades include quartz countertops in all bathrooms, beautiful zebra blinds, a 2026 refrigerator, and an epoxy-finished two-car garage. Step outside to exceptional exterior enhancements added in 2025 and 2026, including striking exterior accent lighting that delivers incredible nighttime curb appeal and presence, a fully sealed paver driveway, a welcoming front porch with ceiling fans, and an extended paver pathway wrapping around the house. Practical features include a brand-new gutter system connected to a downpour drainage system, plus a reliable irrigation system. Located in a top-rated school district, this home places you moments away from the scenic Oakland Nature Preserve, community parks like Speer Park, vibrant local farmers markets, rich cultural attractions like the historic Garden Theatre, and nearby dining favorites. Don't miss this incredible gem!

2199 White Feather Loop, Oakland

15725 Signature Drive, Winter Garden
$569,000
6 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
MOVE-IN READY & EASY TO SHOW! Nestled in the highly sought-after Independence community of Winter Garden, this beautifully maintained Lennar “Rio” floor plan offers the perfect combination of location, lifestyle, and resort-style amenities. This spacious two-story home features 6 bedrooms, 3 full baths, a versatile loft, and 2,714 sq. ft. of living space, all situated on a desirable corner lot. Freshly painted, vacant, and in impeccable condition, this home is ready for its next owner. The thoughtfully designed layout offers generous living spaces, a spacious kitchen with solid wood cabinetry and granite countertops, stainless steel appliances, an interior laundry room, smart thermostat, security cameras, and a private side - backyard. Additional improvements include a newer A/C system, insulated garage, and garage door opener. A covered and screened outdoor area provides additional space to relax and enjoy the Florida lifestyle. Independence is one of Horizon West’s desirable master-planned communities, offering an exceptional array of amenities including clubhouses, resort-style community pools, fitness facilities, tennis courts, playgrounds, parks, sidewalks, and private community boat ramps with lake access. Ideally located near shopping, dining, entertainment, schools, and everyday conveniences, with easy access to SR-429 and Central Florida’s world-famous attractions. Enjoy convenient access to the growing Horizon West area, Winter Garden destinations, restaurants, cinemas, Publix, Walmart, and Walt Disney World Resort. Immaculate, spacious, vacant, and truly move-in ready, this is an exceptional opportunity to enjoy the Independence lifestyle in one of Winter Garden’s most desirable locations. Schedule your private showing today!

15725 Signature Drive, Winter Garden

Start Your Search

How much is your home worth?

Get instant property value now!