Oakland Trails Real Estate

Oakland Trails Real Estate

Welcome to Oakland Trails, a charming subdivision nestled in the heart of Winter Garden, Florida. This delightful community is a hidden gem in Orange County, offering a perfect blend of suburban tranquility and modern conveniences. With its picturesque tree-lined streets and beautifully designed homes, Oakland Trails is ideal for families, retirees, and anyone looking to embrace the Florida lifestyle.

Residents of Oakland Trails enjoy a wealth of amenities that enhance their living experience. The community features well-maintained parks, walking trails, and playgrounds, making it easy for families to spend quality time outdoors. The nearby West Orange Trail offers miles of scenic pathways for biking, jogging, and leisurely strolls, ensuring that outdoor enthusiasts will always have a place to explore.

Convenience is key in Oakland Trails, with easy access to major highways, shopping centers, and dining options. Just a short drive away, you’ll find the vibrant downtown Winter Garden, where you can enjoy local boutiques, farmer’s markets, and delightful eateries that showcase the area’s culinary scene. Plus, with top-rated schools nearby, families can rest assured that their children will receive an excellent education.

Whether you’re looking for a cozy single-family home or a spacious townhome, Oakland Trails offers a variety of housing options to suit different lifestyles and budgets. With its friendly atmosphere, scenic surroundings, and proximity to all that Winter Garden has to offer, Oakland Trails is not just a place to live—it's a place to call home. Come and discover the charm of Oakland Trails today!

Newest Listings in Oakland Trails

$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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