Oakland Trails Real Estate

Welcome to Oakland Trails, a vibrant and picturesque subdivision nestled in the heart of Winter Garden, Florida. This charming community is a hidden gem in Orange County, where modern living meets the tranquility of nature, making it the perfect place to call home.

Oakland Trails boasts a variety of beautifully designed single-family homes, each offering unique architectural features and spacious layouts. With an emphasis on family-friendly living, the subdivision is surrounded by lush greenery, scenic walking trails, and serene parks that invite residents to explore the great outdoors. Imagine morning jogs along tree-lined paths or weekend picnics in the nearby parks, all within arm's reach of your front door.

The community is conveniently located near Winter Garden's historic downtown, where you can enjoy an array of delightful dining options, boutique shopping, and vibrant local events. The famed West Orange Trail is just a stone's throw away, providing endless opportunities for biking, jogging, and enjoying the beautiful Florida weather.

Families will appreciate the highly-rated schools in the area, ensuring that children receive a top-notch education. With easy access to major highways, commuting to nearby Orlando for work or play is a breeze.

At Oakland Trails, you’re not just buying a home; you’re investing in a lifestyle that celebrates community, comfort, and connection. Whether you’re a first-time buyer or looking to downsize, this subdivision offers the perfect blend of modern amenities and natural beauty. Come discover your dream home in Oakland Trails—where every day feels like a getaway!

Newest Listings in Oakland Trails

$730,000

5 Beds ⋅ 3 Baths ⋅ Oakland Trails SubDv. ⋅ 34787 Zip Code

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, Oakland

1750 Standing Rock Circle, Winter Garden

$640,000

4 Beds ⋅ 3 Baths ⋅ Oakland Trails SubDv. ⋅ 34787 Zip Code

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

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