Longleaf/Oakland Rep Real Estate

Welcome to Longleaf/Oakland Rep, a picturesque subdivision nestled in the heart of Winter Garden, Florida! This charming community, located in Orange County, is a hidden gem that perfectly blends suburban tranquility with modern conveniences.

Longleaf/Oakland Rep is characterized by its lush landscapes and friendly atmosphere, making it an ideal place for families, retirees, and everyone in between. The tree-lined streets are adorned with beautiful homes that showcase a variety of architectural styles, ensuring there's something for every taste. Residents enjoy spacious lots, well-maintained parks, and a close-knit community vibe that fosters lasting friendships.

One of the highlights of living in Longleaf/Oakland Rep is its prime location. Just a short drive away, you'll find the vibrant downtown Winter Garden, where charming boutiques, delightful restaurants, and lively farmers' markets await. Outdoor enthusiasts will appreciate the nearby West Orange Trail, perfect for walking, biking, or jogging amidst scenic views.

Families will also benefit from the highly-rated schools in the area, providing quality education and a supportive environment for children. With easy access to major highways, commuting to nearby cities and attractions is a breeze, making this subdivision a perfect choice for those who want the best of both worlds.

Whether you're looking for a peaceful retreat or an active lifestyle, Longleaf/Oakland Rep offers a warm and welcoming community that feels like home. Come discover the charm of this exceptional neighborhood and start your next chapter in Winter Garden today!

Newest Listings in Longleaf/Oakland Rep

$515,000

3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv.

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, Winter Garden

$355,000

3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv.

JUST REDUCED!!!!!!!!!!!!!!!!!!!!!! A well-maintained, stunning, and ready-to-move-in townhouse located in the highly desirable Longleaf at Oakland community. Built in 2019, this beautifully maintained home offers 3 spacious bedrooms, 2.5 bathrooms, and 1,620 square feet of bright, open-concept living space designed for both relaxation and entertaining. The inviting front porch is the perfect place to enjoy your morning coffee. Inside, abundant natural light flows through the numerous windows, enhancing the spacious open-concept layout. The large and contemporary kitchen features an island, stainless steel appliances, granite countertops, and an oversized pantry, with premium finishes that seamlessly flow into the main living and dining areas, making it ideal for both everyday living and entertaining. Upstairs, the primary suite serves as your private retreat, featuring an En-suite bath and ample closet space, alongside two additional bedrooms perfect for family, guests, or a dedicated home office. Step outside to the private courtyard, perfect for grilling and enjoying Florida’s beautiful weather with plenty of space for outdoor seating or even a hot tub. The two-car garage offers private rear entry into the home with a spacious driveway that provides additional parking along with guest parking nearby. There is additional parking in the front of this home also. Enjoy being just steps away from the beautiful community pool overlooking the pond and the neighborhood playground. This home and community provides everything the Florida Lifestyle has to offer ! Living here means embracing an incredible Central Florida lifestyle. The Longleaf community features a sparkling resort-style pool with a cabana, a playground, and scenic walking paths. Best of all, you are just steps away from the historic West Orange Trail and the Oakland Nature Preserve, making outdoor adventures effortless. When you want to head out for dinner or shopping, the vibrant culture of downtown Winter Garden and the famous Plant Street Market are only minutes away. Plus, with quick access to major highways like the Florida Turnpike and SR-429, you are seamlessly connected to all of Orlando's world-class theme parks, dining, and entertainment. Don't miss the opportunity to make this beautiful turnkey property your own!

1511 Sweet Apple Street, Winter Garden

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