Longleaf/Oakland Rep Homes for Sale

Welcome to the charming subdivision of Longleaf/Oakland Rep in Winter Garden, Florida. This sought-after community is nestled in the heart of Orange County, offering a perfect blend of suburban tranquility and urban convenience.

Longleaf/Oakland Rep is known for its picturesque tree-lined streets, well-maintained sidewalks, and lush green spaces. The neighborhood boasts a variety of home styles, including spacious single-family residences, cozy townhomes, and modern condominiums. Whether you are looking for a starter home, a forever home, or an investment property, Longleaf/Oakland Rep has something for everyone.

Homes for sale in Longleaf/Oakland Rep are highly desirable, featuring open floor plans, gourmet kitchens, luxurious master suites, and private outdoor living spaces. Residents enjoy access to top-rated schools, shopping centers, dining options, recreational facilities, and major highways. With a strong sense of community and a tranquil ambiance, Longleaf/Oakland Rep is the perfect place to call home.

If you are in the market for a new home in Winter Garden, look no further than Longleaf/Oakland Rep. Explore the available properties and find your dream home in this beautiful subdivision. Don't miss the opportunity to live in one of the most desirable neighborhoods in Orange County, Florida.

Newest Longleaf/Oakland Rep Homes for Sale

$515,000

3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code

Welcome home to this beautifully maintained 3-bedroom, 2.5-bath home in the highly sought-after Longleaf at Oakland community! From the moment you arrive, you will appreciate the inviting feel, thoughtful layout, and pride of ownership throughout. Inside, enjoy spacious bedrooms, a versatile upstairs loft perfect for a home office, media room, or additional living space, and a comfortable family room designed for everyday living and entertaining. Step outside to a wonderful backyard and porch area, with both the family room and porch pre-wired for speakers—perfect for creating an effortless indoor-outdoor entertaining experience. The two-car garage even features an electric vehicle charging outlet. The location is hard to beat— take a quick 5-minute walk to the West Orange Trail, enjoy the shops, dining, and charm of Downtown Winter Garden just 10 minutes away, and reach the Florida Turnpike in minutes. Beautifully cared for, ideally located, and truly move-in ready—this is the Oakland home you’ve been waiting for!

2696 Bobcat Chase Boulevard, Oakland

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