Oakland Trails Real Estate

Welcome to Oakland Trails, a hidden gem nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This picturesque subdivision is designed for those who crave a blend of tranquility and modern living, making it the perfect community for families, retirees, and everyone in between.

As you enter Oakland Trails, you'll be greeted by lush landscapes and beautifully manicured lawns that create a warm and inviting atmosphere. The community features an array of charming single-family homes, each designed with contemporary aesthetics and thoughtful layouts that cater to today’s lifestyle. Many of these homes come equipped with spacious kitchens, cozy living areas, and private backyards, ideal for entertaining friends or enjoying quiet evenings under the stars.

One of the standout features of Oakland Trails is its commitment to outdoor living. Residents can take advantage of scenic walking trails, parks, and playgrounds, perfect for leisurely strolls or family outings. The community is also conveniently located near the captivating Lake Apopka, offering opportunities for fishing, biking, and nature exploration.

For those who appreciate convenience, Oakland Trails is just minutes away from the charming downtown Winter Garden, where you can find delightful shops, dining options, and a bustling farmer's market. Plus, easy access to major highways ensures that the attractions of Orlando, including theme parks and entertainment venues, are only a short drive away.

Experience the best of Florida living in Oakland Trails, where community spirit meets modern comfort. Your dream home awaits!

Newest Listings in Oakland Trails

2470 Standing Rock Circle, Winter Garden

$730,000

5 Beds ⋅ 3 Baths ⋅ O6443027 MLS

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

1750 Standing Rock Circle, Winter Garden

$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

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