Winter Garden/Oakland Homes with Playground Amenities

Winter Garden/Oakland Homes with Playground Amenities

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. Known for its picturesque landscapes, vibrant community, and rich history, this area is a hidden gem that perfectly blends the charm of small-town living with the conveniences of urban life.

Winter Garden boasts a delightful downtown area filled with unique shops, delectable dining options, and a thriving farmers' market, all set against the backdrop of beautiful historic architecture. Just a stone’s throw away, Oakland offers a serene escape with its lush parks and scenic views, making it an ideal spot for families and nature enthusiasts alike.

For those seeking a family-friendly home, the properties in this region are particularly appealing, especially those equipped with playground amenities. Imagine stepping into your backyard, where your children can enjoy a safe and fun environment, complete with playground equipment that encourages creativity and active play. These homes not only provide a sanctuary for your family but also foster a sense of community, where neighbors become friends and children can thrive in a safe, engaging atmosphere.

With easy access to major highways, you’re just a short drive away from Orlando’s world-renowned attractions, while still enjoying the tranquility of suburban living. Whether you’re a first-time homebuyer or looking to upgrade, Winter Garden and Oakland offer a variety of homes that cater to your needs, all surrounded by the warmth and charm that define this lovely region. Come discover your dream home in this idyllic corner of Florida!

Newest Winter Garden/Oakland Homes with Playground Amenities

$560,000
4 Beds ⋅ 3 Baths ⋅ John Lake Pointe SubDv. ⋅ 34787 Zip Code
Motivated seller! Located in the community of Johns Lake Pointe, this beautifully designed 4-bedroom, 2.5-bath home offers a desirable split floor plan and a spacious 2-car garage. A welcoming front porch sets the tone for this inviting residence. The living room overlooks the private fenced backyard, creating the perfect setting for relaxing or entertaining. The kitchen features chestnut cabinetry, stainless steel appliances, a center island with a sit-in bar, and a separate dining area ideal for gatherings. The primary suite includes a well-appointed primary bathroom with dual sinks, a garden tub, and a walk-in shower. The back porch is protected by a screen. With a recent price improvement, this home presents outstanding value, flexibility, and the opportunity to personalize to your taste. Ideally located less than 20 minutes from Disney, Johns Lake Pointe is a beautifully maintained community offering resort-style amenities, including a clubhouse with a pool and kitchen, fitness center, yoga room, tennis courts, and playground. Enjoy an exceptional lifestyle in a prime location, priced to allow the next owner to create a private oasis. Don’t miss the opportunity to make this remarkable house your home!

745 Marsh Reed Drive W, Winter Garden
$689,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code
Welcome to Stoneybrook West—a one-of-a-kind community in Winter Garden! This premier neighborhood offers 24-hour guarded entry, a massive town center, and resort-style amenities including an Olympic-sized pool with a splash zone, state-of-the-art fitness center, playground, tennis, basketball, and pickleball courts. Enjoy lakeside living with a fishing/viewing pier and private boat ramp, plus a full calendar of community events. Best of all, your HOA fees cover both internet and cable! Set on a tranquil pond with no rear neighbors, this home boasts irresistible curb appeal from the moment you arrive. Inside, the thoughtfully designed floor plan balances elegance and ease. The front of the home features formal living and dining areas—perfect for hosting—while the rear opens to a bright, open-concept kitchen and family room ideal for everyday living. The kitchen is a chef's delight with ample counter space, a walk-in pantry, stainless steel appliances, stylish tile backsplash, and a breakfast bar. Step through the sliding doors to a screened patio and fully fenced backyard—a private oasis for pets, play, or peaceful pond gazing. Need space for guests or extended family? A main-floor bedroom with a full bath offers flexibility and privacy. Upstairs, a generous loft awaits—use it as a media room, playroom, or second living area. Both the loft and the primary suite open to a screened balcony with serene views. The primary retreat itself is a showstopper, featuring a garden tub, separate walk-in shower, dual vanities with a makeup station, and an enormous walk-in closet. Convenience continues with an upstairs laundry room equipped with cabinets and a utility sink. Fresh new flooring has been installed throughout the entire upper level, and the home has been treated to a brand-new coat of paint, giving it a clean, modern feel throughout. Recent upgrades also include a new roof (2023), new water heater (2023), and AC (2019). You'll also appreciate surround sound pre-wiring in the family room and loft, ceiling fans throughout, and abundant storage. Located just steps from the resident gate, Balforn Tower Way places you minutes from the community town center, golf clubhouse, top-rated schools, dining, shopping, medical facilities, and entertainment. This is more than a home—it's a lifestyle.

2549 Balforn Tower Way, Winter Garden
$663,065
4 Beds ⋅ 4 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12331 Silk Mimosa Alley, Winter Garden
$369,500
3 Beds ⋅ 3 Baths ⋅ Stoneybrook West Unit 8 SubDv. ⋅ 34787 Zip Code
Welcome to Westbrook at Stoneybrook West, a well-established townhome community in the heart of Winter Garden! This spacious 3-bedroom, 2.5-bath townhome offers 1,650 square feet of comfortable living space along with an attached 2-car garage. The main level features an open living and dining area, while all three bedrooms are conveniently located upstairs, including a spacious primary suite with a private bath and walk-in closet. A covered outdoor patio provides additional space to relax and enjoy the Florida weather. The home is currently being refreshed with new interior paint and new flooring throughout, allowing the next owner to move in and enjoy a clean, updated space from day one. Westbrook offers residents a community pool, playground, sidewalks, and plenty of guest parking, all in a location that puts everyday conveniences close by. Publix, Walgreens, restaurants, and shopping are just minutes away, with Winter Garden Village and Historic Downtown Winter Garden also within easy reach. Spend the weekend exploring the brick-lined streets of Plant Street, visiting the Saturday Farmers Market, or enjoying miles of biking and walking along the West Orange Trail. With convenient access to SR-429, SR-50, and Florida’s Turnpike, commuting throughout Central Florida, Downtown Orlando, the airport, and the theme parks is a breeze. Enjoy low-maintenance townhome living in one of Winter Garden’s most convenient locations — schedule your private showing today!

1327 Priory Circle Unit 1327, Winter Garden
$419,999
3 Beds ⋅ 3 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code
Storey Grove ** 2023 built ** Open floorplan **BACKS TO GREENSPACE!!** Beautiful wood ceramic tile entire 1st floor ** Attractive tv wall wood accent inlay in the family room ** White kitchen cabinetry with quartz counters and large cooking island ** All bedrooms are on the 2nd floor ** Nice size +/-16x20 brick paver patio area and 2 car detached garage ** Great RING security system, RING cameras, doorbell and door and window sensors ** Tesla EV power outlet is already in place in the garage ** Overhead storage racks in the garage are included ** Storey Grove community amenities include a huge resort style community pool, fitness center, basketball courts, children's playground and green space area. Room measurements are from builder floor plan. Buyers to verify all room measurements.

10648 Words Drive, Winter Garden
$560,000
4 Beds ⋅ 4 Baths ⋅ Storey Grove Ph 1b-3 SubDv. ⋅ 34787 Zip Code
This beautiful 4 bedroom, 3 1/2 bath home features an open layout with designer finishes that are light and bright throughout. There are 2 master bedroom one on the first floor and in the second floor Perfect for families. Large great room downstairs, bonus room/loft upstairs with vaulted ceiling and a beautiful backyard. Upgraded just like the model. Quartz counter top throughout, upgraded light cabinets, wood plank, tile floor. Upgraded GE Profile appliances and complete Smart Home Package with smart thermostats, smart switches Wireless range extenders built in Alexa smart home controls. Storey Grove is beautiful picturesque community with pool, fitness center, parks, playgrounds and more. It's a perfect location just minutes from Disney, Shopping, Dining, New Hamlin retail and theaters, Easy Access to 429 Expressway, and zoned for A rated schools . Come and check personally .

15163 Book Club Road, Winter Garden
$635,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully renovated golf-front home in the gated community of Stoneybrook West. Offering over 2,800 square feet of living space, this home combines a spacious and flexible floor plan with a fantastic setting overlooking the 6th hole and no rear neighbors. Recent improvements include a newer roof and A/C, fresh exterior paint, renovated kitchen, bathrooms, and flooring. The main level offers multiple living and dining spaces, while the kitchen features stone countertops, stainless steel appliances and abundant cabinetry. Upstairs, the spacious primary suite includes a tray ceiling, walk-in closet and private bath with dual vanities and a beautifully remodeled walk-in shower. The oversized loft provides plenty of flexibility for a second living area, media room, playroom or home office. Step outside to a large backyard with expansive golf course views and plenty of room to enjoy the outdoor living. Stoneybrook West offers an impressive collection of amenities, including a community pool, golf, clubhouse, tennis and basketball courts, playgrounds and walking paths. Ideally located near Winter Garden Village, historic Downtown Winter Garden, shopping, dining and major roadways, this home offers a great combination of space, improvements, amenities and community.

15081 Masthead Landing Circle, Winter Garden
$464,990
3 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
Under Construction. Waterleigh presents the Sandhill. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with powder room, spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As we head upstairs, you are greeted with a loft area. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Sandhill includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *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.*

16534 Barbours Creek Way, Winter Garden
$825,000
4 Beds ⋅ 3 Baths ⋅ Overlook At Hamlin SubDv. ⋅ 34787 Zip Code
Welcome to 5743 Thomas Square Drive, an exceptional single-story pool home located in the lakefront community of The Cove at Hamlin in Winter Garden. Built in 2018, this beautifully upgraded Jamestown model offers 4 bedrooms, 2.5 bathrooms, 2,917 square feet, and a thoughtfully designed split floor plan that combines comfort, style, and effortless Florida living. Inside, engineered hardwood floors, custom archways, high ceilings, and abundant natural light lead into an expansive open-concept living space. The kitchen serves as the heart of the home with quartz countertops, stainless steel appliances, generous cabinetry, and seamless flow into the dining and living areas. One of the home's most impressive features is the massive owner's suite. Offering an exceptional amount of space rarely found in homes of this size, the suite easily accommodates a full bedroom setup with room for a sitting area, additional furnishings, or a private retreat within the room. A spacious owner's bath and generous custom closet complete the suite, while three additional bedrooms provide flexibility for family, guests, or a home office. Step outside to an extended screened lanai overlooking the private saltwater pool and beautifully landscaped fenced backyard. Solar and natural gas pool heating, built-in lighting, a fire pit, and a gas connection for an outdoor grill create a backyard designed for entertaining and enjoying the Florida lifestyle year-round. Lake views complete the setting, along with the opportunity to enjoy nightly Disney fireworks from home. Beyond the home, one of the biggest draws is the incredible Hamlin lifestyle just minutes from your front door. Spend an evening putting at PopStroke, catch a movie from a luxury recliner at Cinépolis, grab dinner at Ford's Garage or Agave Bandido, meet friends at Home State Brewing Co., or start the morning with coffee and breakfast at Toastique. Hamlin continues to offer an exciting mix of restaurants, entertainment, shopping, fitness, community events, and everyday conveniences, making it easy to enjoy a night out without traveling far from home. The Cove at Hamlin offers its own impressive collection of amenities, including a resort-style community pool, clubhouse, fitness center, splash pad, playgrounds, dog park, walking trails, outdoor gathering spaces, and private access to Lake Hancock with a community boat ramp and dock. With easy access to SR 429, Walt Disney World, Hamlin Town Center, and everything Horizon West has to offer, 5743 Thomas Square Drive is more than a beautiful pool home. It offers the opportunity to live in the heart of one of Central Florida's most exciting and rapidly growing communities.

5743 Thomas Square Drive, Winter Garden
$424,990
3 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
Under Construction. Waterleigh presents the Ibis. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with an open concept a spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage and powder room at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As you head up to the second floor you are greeted with all 3 bedrooms and 2 bathrooms. The bedroom one suite impresses with double bowl vanity, walk in closet and spacious shower space. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Ibis includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *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.*

16546 Barbours Creek Way, Winter Garden
$499,999
3 Beds ⋅ 3 Baths ⋅ Watermark SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained home in the highly sought after Watermark at Horizon West community! This spacious two story residence offers 3 bedrooms, 2.5 bathrooms, and over 2,000 square feet of thoughtfully designed living space. The open concept floor plan is perfect for both everyday living and entertaining, featuring wood tile flooring throughout the main level, abundant natural light, and a modern kitchen complete with built in appliances, ample cabinetry, generous counter space, and a large island overlooking the living and dining areas. Upstairs, you'll find a versatile loft that makes an ideal home office, media room, or play area, along with a spacious primary suite featuring a walk in closet and an en-suite bath. Two additional bedrooms, a full bath, and an upstairs laundry room complete the second floor. Enjoy Florida living from the welcoming front porch while taking advantage of the home's rear entry two car garage and low maintenance yard. Residents of Watermark enjoy resort style amenities including a community pool, fitness center, tennis courts, playground, parks, walking trails, and beautifully maintained common areas. You’re also within close distance to restaurants and just a short drive to Disney, shopping, and everything Winter Garden and Horizon West have to offer. If you’re looking for a clean, move in ready home in a great location with a strong lifestyle, this one checks all the boxes!

14543 Golden Harbor Lane, Winter Garden
$340,000
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
Welcome to The Grove Resort & Water Park Orlando, a premier vacation resort just minutes from Walt Disney World. This spacious 3-bedroom, 3-bath condominium is located on the 3rd floor of Building 2, offering exceptional convenience to the main lobby and resort amenities. Designed for vacation enjoyment and investment potential, the residence features a spacious open floor plan, well-appointed kitchen, comfortable living and dining areas, and three bedrooms and baths providing plenty of room for family and guests. Enjoy your own Orlando vacation retreat and take advantage of rental income . The Grove offers an impressive resort experience with Surfari Water Park, multiple pools, a lazy river, FlowRider surf simulator, restaurants and bars, fitness center, spa, arcade, Lake Austin activities, and complimentary transportation to Walt Disney World. Whether your goal is creating memorable Florida vacations, generating rental income, or enjoying the best of both, this Building 2 location offers convenience, flexibility, and investment potential in one of Orlando’s most popular vacation destinations. Vacation when you want. Earn rental income when you don’t.

14501 Grove Resort Avenue Unit 2342, Winter Garden
Start Your Search