Winter Garden/Oakland Homes with Playground Exterior Features

Winter Garden/Oakland Homes with Playground Exterior Features

Welcome to Winter Garden and Oakland, two of Central Florida’s most charming communities nestled in the heart of Orange County. Known for their picturesque landscapes, vibrant downtown areas, and family-friendly atmosphere, these neighborhoods offer an idyllic setting for those looking to plant roots in the Sunshine State.

Winter Garden, with its historic downtown adorned with quaint shops, local eateries, and a thriving farmers market, exudes a warm and inviting charm. The nearby Oakland, a serene enclave, boasts lush greenery and scenic parks, making it the perfect backdrop for outdoor enthusiasts and families alike. Both communities are well-connected, with easy access to major highways, making commutes to nearby Orlando and its world-renowned attractions a breeze.

One of the standout features of homes in this region is their family-oriented amenities, particularly properties with playgrounds and exterior features designed for outdoor fun. Imagine your children laughing and playing just steps from your back door, while you relax on the patio, enjoying the beautiful Florida weather. These homes are designed with families in mind, offering safe, spacious yards where kids can explore and create lasting memories.

Whether you’re seeking a cozy bungalow or a spacious family home, Winter Garden and Oakland provide a diverse range of options to suit every lifestyle. With their rich community spirit, top-rated schools, and abundant recreational opportunities, it’s no wonder that families are flocking to this enchanting corner of Florida. Come discover your dream home in Winter Garden or Oakland, where the perfect blend of comfort and community awaits!

Newest Winter Garden/Oakland Homes with Playground Exterior Features

$369,900
3 Beds ⋅ 3 Baths ⋅ Stoneybrook West I SubDv. ⋅ 34787 Zip Code
Welcome to Westbrook, a well-established townhome community tucked along Avalon Road in the heart of Winter Garden. This 3bed, 3bath townhome offers 1924 sqft of easy, low-maintenance living, an open-concept main level, stainless steel appliances, quartz countertops, and a spacious owner's suite! Residents enjoy a community pool and playground with ample parking, all just minutes from everything that makes Winter Garden special: the brick-lined Plant Street historic district, the West Orange Trail, the Saturday Farmers Market, and Winter Garden Village shopping and dining. With quick access to SR-429, SR-50, and Florida's Turnpike, you're a short drive from downtown Orlando, the airport, and the world-famous theme parks. Low-maintenance living in one of West Orange County's most sought-after towns — schedule your private showing today!

15510 Campden Street, Winter Garden
$375,000
3 Beds ⋅ 3 Baths ⋅ Stoneybrook West I SubDv. ⋅ 34787 Zip Code
You will find comfort, convenience and flexibility with this lovely well maintained 3 bedroom 2 1/2 bath townhome located in Stoneybrook West. With Ceramic tile in the kitchen and bathrooms, the owner replaced all carpet with laminate wood flooring. The en suite primary bathroom was beautifully updated in 2025 with attention to upgrades like a double vanity quartz countertop and soft closed drawers. The Primary suite has two walk in closets and new energy efficient windows. The second bedroom boasts a walk in closet as well. From the cozy screened back patio, it’s a quick walk to the community playground and pool. This quiet family friendly community is within walking distance of all your shopping needs and also just a short drive to Winter Garden Village and charming Historic Downtown Winter Garden. There you’ll find the West Orange Trail for biking, running or a simple stroll after dining at some of the area’s finest restaurants. Adding to your peace of mind, the roof was replaced in 2023 along with repainting of the exterior of the properties in the community. The HVAC was replaced in April 2021. The exterior was upgraded to a 3 ton in August 2019 and maintained annually. Schedule your showing and make this turnkey townhouse your home.

15514 Campden Street, Winter Garden
$875,000
5 Beds ⋅ 4 Baths ⋅ West Lake Hancock Estates SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 5-bedroom, 3-bath home with a dedicated office, offering the perfect blend of elegance, comfort, and functionality in the highly desirable Overlook at Hamlin community of Winter Garden. Thoughtfully designed for today's lifestyle, this spacious floor plan features a sought-after first-floor primary suite, providing a private retreat with convenience and flexibility. From the moment you enter, you'll appreciate the pride of ownership evident throughout. Gorgeous wood flooring flows through the main living areas, complemented by brand-new carpet and fresh interior paint for a truly move-in-ready feel. The dedicated office is ideal for working from home, studying, or creating a quiet flex space. The heart of the home is the open-concept living area, where a beautiful gas fireplace creates a warm and inviting focal point. The spacious kitchen overlooks the family room and dining area, making it easy to entertain while staying connected with family and guests. Step outside to one of the home's standout features—an oversized covered lanai and an expansive screened enclosure that extends your living space outdoors. Whether you're enjoying your morning coffee, dining al fresco, or hosting gatherings, this incredible outdoor retreat is designed for year-round Florida living. Upstairs, you'll find generously sized secondary bedrooms that provide plenty of space for family and guests, while the thoughtful layout offers privacy and versatility for every stage of life. Located in the sought-after Hamlin area, residents enjoy exceptional resort-style amenities, including a private community boat ramp with access to Lake Hancock, a lakeside clubhouse, fitness center, community pool, playgrounds, parks, walking trails, and waterfront recreation. Just minutes from Hamlin Town Center, Walt Disney World, shopping, dining, entertainment, top-rated schools, and major highways, this location offers unmatched convenience and an exceptional lifestyle. With fresh interior paint, gorgeous wood floors, new carpet, a first-floor primary suite, dedicated office, gas fireplace, and an incredible screened outdoor living space, this meticulously maintained home is truly move-in ready and offers everything today's buyers are looking for.

7773 Minutemen Loop, Winter Garden
$1,099,000
6 Beds ⋅ 5 Baths ⋅ Cypress Reserve Ph 2 SubDv. ⋅ 34787 Zip Code
Experience luxury living in this exceptional 6-bedroom, 5-bathroom residence located in the highly sought-after Cypress Reserve community of Winter Garden. Perfectly positioned on a premium homesite with no rear neighbors, this impressive home offers exceptional privacy, tranquil conservation views, and a versatile floor plan designed for today’s lifestyle. The open-concept design showcases beautifully appointed living spaces throughout both floors, making it ideal for multigenerational living or hosting extended family and guests. A dramatic second-floor loft overlooks the main living area, creating an open and inviting atmosphere while providing additional living space. Upstairs also features a second primary suite, three additional spacious bedrooms, a dedicated theater/media room, and a flex room that serves perfectly as a home office, den, or playroom. At the heart of the home is a chef-inspired gourmet kitchen designed to impress, featuring stainless steel appliances, a gas cooktop, double wall ovens, quartz countertops, and an oversized center island with an undermount sink, generous seating, and double-sided cabinetry that provides exceptional storage for both everyday living and entertaining. Motorized shades throughout the main living area add a touch of sophistication and everyday convenience. The spacious family room opens effortlessly to the outdoor living space through triple pocket sliding glass doors, creating a seamless indoor-outdoor lifestyle. Relax year-round on the screened lanai overlooking peaceful conservation views or entertain with ease around the sparkling pool and fully equipped outdoor kitchen featuring a Paradise Grill, built-in sink, and refrigerator. Luxurious owner's suite is a private retreat featuring a spa-inspired bath with dual vanities, a relaxing garden tub, a zero-entry walk-in shower with seamless glass enclosure, and double-door entry to an expansive custom-designed walk-in closet that is sure to impress. A private hallway just off the main living area leads to a spacious guest suite with direct access to the pool, along with a generously sized laundry room for added convenience. Upstairs, you'll find a second primary suite, three additional bedrooms, an expansive loft, a dedicated theater/media room, and a versatile flex room—offering abundant space for family, guests, a home office, fitness room, or additional living area. Additional highlights include a three-car tandem garage offering abundant storage and ample room for a home gym, workshop, or hobby space. LOCATED just minutes from Downtown Winter Garden, the award-winning Winter Garden Farmers Market, Winter Garden Village, shopping, dining, top-rated schools, and major roadways including State Road 429 and Florida’s Turnpike, this exceptional home offers the perfect blend of luxury, comfort, convenience, and location *** This is a rare opportunity to own one of Cypress Reserve’s premier residences and experience the very best of the Winter Garden and true Florida lifestyle. ***

14067 Jomatt Loop, Winter Garden
$1,699,000
5 Beds ⋅ 5 Baths ⋅ Hull Island/Oakland SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this exceptional lakefront retreat on the shores of Lake Apopka, where breathtaking water views, luxury upgrades, and exceptional outdoor living come together to create the ultimate Florida lifestyle. Offering 5 bedrooms, 4.5 bathrooms, and over 4,000 square feet of thoughtfully designed living space, including a convenient first-floor bedroom, this beautifully updated residence showcases more than $500,000 in improvements, creating a move-in-ready experience for the next owner. From the moment you arrive, you'll appreciate the extensive upgrades throughout the home, including porcelain tile throughout the main living areas on the first floor, engineered white oak hardwood flooring throughout the second level, a custom wood and iron staircase, upgraded cabinetry, quartz countertops, designer finishes, and a beautifully appointed kitchen featuring premium KitchenAid appliances, a gas cooktop, and custom soft-close cabinetry. Designed for both everyday living and entertaining, the backyard is a true showpiece. Enjoy a resort-style saltwater pool and spa, gas-heated for year-round enjoyment, expansive outdoor living areas, and a fully equipped summer kitchen featuring premium Blaze appliances. Electric screens allow you to enjoy outdoor dining and entertaining comfortably while taking in the peaceful lakefront setting and stunning sunset views. Boating enthusiasts will appreciate the private dock complete with a 5,000-pound boat lift, offering direct access to Lake Apopka, one of Florida's largest lakes. With more than 30,000 acres of open water to explore, the lake offers endless opportunities for boating, fishing, watersports, and unforgettable sunset cruises. Known for its trophy bass fishing, abundant wildlife, and expansive waterfront views, Lake Apopka provides a rare opportunity to enjoy true lakefront living with the freedom and space that few Central Florida lakes can offer. This property delivers the waterfront lifestyle Florida is known for. Additional highlights include a convenient first-floor bedroom, a second-floor laundry room, solar panels that will be paid off at closing, natural gas service, a Culligan water filtration system, dual pool pumps, and city sewer, a significant advantage for a waterfront property. Ideally located just minutes from Downtown Winter Garden, shopping, dining, and major roadways, this exceptional lakefront residence offers the perfect balance of luxury, recreation, and everyday convenience.

1144 Hull Island Drive, Winter Garden
$550,000
4 Beds ⋅ 3 Baths ⋅ Highland Rdg Ph 2 SubDv. ⋅ 34787 Zip Code
SPECIAL FINANCING AVAILABLE! The seller is offering a promotional 3.875 interest rate through a rate buy-down program, plus ALL closing costs paid when using the preferred lender—creating an incredible opportunity for qualified buyers to significantly reduce their monthly payment and cash needed at closing. Welcome to this stunning newer construction home located in the highly desirable Horizon West area of Winter Garden! Nestled in one of Central Florida’s most sought-after communities, this beautiful two-story residence offers spacious open-concept living, soaring ceilings, and an abundance of natural light throughout. Designed for modern living, the home features expansive living and dining areas, generously sized bedrooms, and a functional floor plan perfect for entertaining or everyday comfort. Enjoy outdoor living with a semi-private fenced backyard, providing the perfect balance of privacy and open space. Ideally situated just minutes from Flamingo Crossings, Walt Disney World, shopping, dining, entertainment, and major highways, this location offers unmatched convenience and lifestyle. Residents also benefit from access to highly rated A+ schools, making this an excellent choice for families. Don’t miss this incredible opportunity to own a beautiful home in one of Winter Garden’s fastest-growing and most desirable neighborhoods. Schedule your private showing today!

14123 Frasier Street, Winter Garden
$420,000
3 Beds ⋅ 3 Baths ⋅ Winding Bay Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful 2022 townhome located in the highly desirable Horizon West area of Winter Garden. This spacious residence features 3 bedrooms, 2.5 bathrooms, and approximately 1,732 square feet of thoughtfully designed living space. The open-concept floor plan offers a modern kitchen with ample cabinetry, a large island, and seamless flow into the dining and living areas, perfect for everyday living and entertaining. Upstairs, the primary suite includes a private bath and generous closet space, while two additional bedrooms provide flexibility for family, guests, or a home office. Enjoy the convenience of a two-car garage, low-maintenance living, and access to excellent community amenities. Ideally located near top-rated schools, shopping, dining, major highways, and world-famous attractions, this home offers the perfect combination of comfort, convenience, and lifestyle in one of Central Florida’s fastest-growing communities.

12042 Grandrose Alley, Winter Garden
$634,990
4 Beds ⋅ 3 Baths ⋅ Storey Grove Ph 3 SubDv. ⋅ 34787 Zip Code
Amazing Single Family, 4 bedrooms and 3 full bathrooms with fenced backyard for privacy and extra security. Designed for comfort and modern living, this property offers creating a clean and elegant look with modern title flooring. All pictures are real, no virtual staging or AI. The community offers excellent amenities, including a resort-style pool, fitness center, basketball court, playground, and clubhouse for residents to enjoy. Ideally located next to top-rated schools, this home allows children to walk to school, making daily routines easier and safer. The property also sits on a premium lot adjacent to a walking path, providing additional privacy and open space. This is a fantastic opportunity to own a beautiful home in a highly desirable community. Solar panel loan must be transferred/assigned to, and assumed by, new buyer. (significant savings).

11036 Robert Frost Drive, Winter Garden
$794,989
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code
Imagine coming home to space, style, and ease—where every detail is already done. This move-in-ready Toll Brothers home offers 4 bedrooms, 3.5 baths, and 3,304 sq. ft. in one of Horizon West’s most desirable communities. From the Tuscan-inspired curb appeal and welcoming front porch to the bright, open living spaces, this home was designed for comfort, flexibility, and effortless entertaining. The chef’s kitchen features a large island and flows seamlessly into the family room and covered lanai. With two primary suites, including one on the main level, the floor plan is ideal for guests, multigenerational living, or a private owner’s retreat. The oversized backyard offers room to create your dream outdoor oasis, including space for a future pool. Enjoy resort-style amenities with lawn care included, a clubhouse, fitness center, parks, playgrounds, and a lakeside pool overlooking Panther Lake. Located minutes from top-rated schools, Hamlin Town Center, Disney, and everything Horizon West has to offer. Luxury without waiting. Space without compromise. This is where your next chapter begins.

15149 Canoe Place, Winter Garden
$335,000
3 Beds ⋅ 3 Baths ⋅ Daniels Lndg A-J SubDv. ⋅ 34787 Zip Code
Beautiful maintained 3 bedroom 2.5 bath townhome located in the highly desirable DANIELS LANDING community in WINTER GARDEN. This property features recent mayor updates including brand new carpet. Rooms on second floor. It has a screened porch to enjoy the afternoons with family and friends. Spacious layout, ideal location and low maintenance living make this property a standout. Top rated schools. Community amenities included gated access, pool, a clubhouse, fitness center and a playground. Conveniently located near Winter Garden Villages that offers shopping and gathering opportunities for everyone needs! Close to Mayor highways Turnpike, 429 and I-4. Minutes from Disney World and many other attractions! Great as a primary home or investment opportunity. A must see today!

13527 Daniels Landing Circle, Winter Garden
$560,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2a SubDv. ⋅ 34787 Zip Code
Move in ready home in Waterleigh one of Winter Garden’s most desirable places to live! Ideally positioned within the community for quick and convenient access, this home also sits directly across from a playground and green space perfect for families and outdoor fun. Freshly updated with new interior paint and brand new carpet throughout the bedrooms and upstairs, this home is truly turnkey. Featuring 4 bedrooms and 3.5 baths, the open concept layout offers a spacious kitchen with granite countertops, stainless steel appliances, large island, and walk in pantry overlooking the living and dining areas. Sliding doors lead to a covered lanai for easy indoor-outdoor living. The first floor includes a bedroom with ensuite bath and a powder room. Upstairs offers a versatile loft, a spacious primary suite with walk-in closet and dual vanities, two additional bedrooms, a full bath, and a convenient laundry room. Enjoy resort-style living in Waterleigh with pools, clubhouse, fitness center, parks, trails, and more all designed for a true Florida lifestyle.

16031 Pebble Bluff Loop, Winter Garden
$599,999
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully designed, architect-crafted townhome, freshly repainted throughout and lovingly maintained by its original owners. From the moment you step inside, you’re greeted by a bright, open-concept layout filled with thoughtful upgrades and elegant details. The main level flows effortlessly, featuring a stylish living and dining area bathed in natural light and accented with refined crown molding. At the heart of the home, the gourmet kitchen impresses with granite countertops, a modern backsplash, ample cabinetry, and an oversized island perfect for entertaining. Transom light doors lead to a screened-in, covered patio—your private retreat to relax and enjoy Florida’s year-round sunshine. Upstairs, the spacious primary suite offers a true escape, complete with a luxurious en-suite bathroom featuring dual vanities, a garden tub, a separate glass-enclosed shower, and tasteful finishes throughout. One of the standout features is the bonus apartment—ideal for guests, extended family, or even as an income-producing opportunity. Completing the home is a 2-car garage with a sleek epoxy finish, combining durability with a clean, polished look. This property is just 17 minutes away from Disney. Schedule your showing today.

8807 Fountain Palm Aly, Winter Garden
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