Oakland Trails Homes for Sale

Oakland Trails Homes for Sale

Welcome to Oakland Trails, an enchanting subdivision nestled in the heart of Winter Garden, Florida. This vibrant community, situated in Orange County, offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, retirees, and everyone in between.

Oakland Trails is characterized by its picturesque tree-lined streets, beautifully landscaped parks, and a strong sense of community. Residents here enjoy access to a variety of amenities, including walking trails, playgrounds, and recreational facilities that promote an active lifestyle. The neighborhood is designed with families in mind, providing a safe and welcoming environment for children to play and grow.

The homes for sale in Oakland Trails are as diverse as its residents. From charming single-family homes to modern townhouses, there’s something to suit every taste and budget. Many of these residences feature open floor plans, spacious backyards, and contemporary finishes, making them perfect for both entertaining and everyday living. With a focus on quality construction and thoughtful design, these homes are built to accommodate the needs of today’s homeowners.

Beyond the serene surroundings of Oakland Trails, residents enjoy the convenience of nearby shopping centers, dining options, and top-rated schools. The community is also just a short drive from the excitement of downtown Winter Garden, where you can explore local boutiques, farmers' markets, and cultural events.

If you’re looking for a place that combines comfort, community, and convenience, Oakland Trails in Winter Garden is the perfect choice. Discover your dream home today and experience the vibrant lifestyle this charming subdivision has to offer!

Newest Oakland Trails Homes for Sale

$454,900
3 Beds 3 Baths Oakland Trails SubDv. 34787 Zip Code
Welcome to this exceptional home in the highly sought-after Oakland Trails community! This beautifully designed 3-bedroom, 2.5-bath residence offers approximately 1,838 square feet of thoughtfully designed living space with an open and functional floor plan that truly stands out in the neighborhood. From the moment you arrive, you’ll notice the extended brick paver driveway, providing additional parking and excellent curb appeal. The inviting front porch is perfectly positioned with elevated views overlooking the peaceful walking trails — an ideal spot to enjoy your morning coffee or unwind in the evenings. Inside, the bright and airy layout flows seamlessly, creating an inviting atmosphere for both everyday living and entertaining. High ceilings and tall doorways enhance the spacious feel throughout the home. The open-concept living, dining, and kitchen areas are designed for comfort and functionality. The beautifully upgraded kitchen features polished granite countertops, an expansive breakfast bar island, rich espresso shaker cabinetry with crown molding, stainless steel appliances, recessed lighting, a spacious pantry, and a bright window above the sink — combining style and practicality for modern living. Upstairs, the spacious primary suite offers a private retreat, while two additional bedrooms, a versatile loft area, and a convenient second-floor laundry room provide flexibility for family, guests, or a home office. Built with energy efficiency in mind, this Meritage home includes spray foam insulation to help maintain indoor comfort while reducing utility costs. The home is also equipped with an advanced HVAC system featuring enhanced air purification and fresh-air intake for improved comfort and healthier living. Ideally located approximately 30 minutes from Disney, Universal Studios, and Downtown Orlando, this home offers convenient access to major attractions while maintaining a peaceful residential setting. Oakland Trails is known for its top-rated schools, scenic walking and biking trails, low HOA, and thoughtfully planned amenities, including a community pool, clubhouse, and dog park. Just minutes away, Downtown Winter Garden offers the popular Winter Garden Farmers Market, charming boutiques, restaurants, and cultural attractions in one of Central Florida’s most beloved small-town districts. For commuters, easy access to the Florida Turnpike allows convenient travel throughout Orlando and to the airport. Investors will also appreciate the home’s strong long-term rental potential, supported by modern construction, low-maintenance design, and consistent tenant demand. This home perfectly blends peaceful neighborhood living with outstanding convenience, style, and everyday functionality. Don’t miss your opportunity to own one of Oakland’s standout homes!

2247 White Feather Loop, Oakland

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