Oakland Trails Homes for Sale

Virtually Staged. Welcome to 2470 Standing Rock Circle, a beautifully maintained Montclair model by Meritage Homes in the desirable Oakland Trails community. Offering 3,446 square feet, 5 bedrooms, and a spacious open floor plan, this home has been meticulously cared for and is truly move-in ready. The first floor features a bedroom with a full bath, providing a comfortable and private space for guests. The main living areas flow seamlessly together and include surround sound in the living room, creating an inviting space for everyday living and entertaining. Step outside to the extended covered lanai spanning the full length of the home, with additional pavers extending the outdoor living area into the fully fenced backyard. Upstairs, you'll find the spacious primary suite with a tray ceiling, three additional bedrooms, and an oversized loft currently used as a theater room, complete with surround sound. This flexible space is perfect for movie nights, a game room, home office, or additional living area. Adding even more value, the exterior of the home will be freshly painted prior to closing, and the garage floor will receive a fresh epoxy finish. Located in charming Oakland, residents enjoy convenient access to the West Orange Trail, Oakland Nature Preserve, and Lake Apopka, while being just minutes from Historic Downtown Winter Garden with its restaurants, shops, Plant Street Market, Farmers Market, and year-round community events. With easy access to shopping, dining, and major roadways, this home offers plenty of space in a fantastic Central Florida location.

2470 Standing Rock Circle, Winter Garden

Listing courtesy of HOMEVEST REALTY. 407-897-5400

$640,000

4 Beds ⋅ 3 Baths ⋅ S5156172 MLS

Welcome to this energy efficient two story home built in 2020, ideally located in the highly desirable Town of Oakland with direct access to the West Orange Trail and excellent proximity to Historic Downtown Winter Garden. Situated on a spacious .21 acre lot, this residence offers 2,614 square feet of living space, 4 bedrooms, 2.5 bathrooms, a 2 car garage, and an open concept floor plan. The first floor features a formal living area, open kitchen with granite countertops a double oven, stainless steel appliances, eat-in dining space and a family room with upgraded luxury laminate flooring. Upstairs you’ll find all four bedrooms, two full bathrooms, and a versatile bonus/flex loft area. The bedrooms feature ceiling fans and spacious walk-in closets. Additional highlights include excellent storage throughout the home, generously sized under stair storage, and a separate drop zone. Step outside to enjoy bespoke landscaping with wired outdoor lighting, garden beds for your next harvest, an extended patio creating the perfect outdoor oasis. Conveniently located adjacent to the community pool, this home offers both comfort and convenience. Enjoy easy access to Orlando's theme parks, shopping, dining, and recreation, including the nearby 22-mile paved West Orange Trail as well as the Nature Preserve, perfect for walking, biking, and outdoor activities. A newly built Costco and an array of restaurants are also nearby. Easy access to Turnpike, 429, 408 making any commute a breeze. Enjoy the charm of the Town of Oakland while being just minutes from Winter Garden and Orlando. Schedule your tour today!

1750 Standing Rock Circle, Winter Garden

Listing courtesy of EXP REALTY LLC. 888-883-8509

$454,900

3 Beds ⋅ 3 Baths ⋅ S5150852 MLS

Under contract-accepting backup offers. 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, Winter Garden

Listing courtesy of LPT REALTY, LLC. 877-366-2213

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Oakland Trails - Winter Garden Florida Homes for Sale

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