Oakland Park Homes with Sidewalks Community Features

Welcome to Oakland Park, a charming subdivision nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This delightful community is designed for those who appreciate a blend of modern living and the warmth of a close-knit neighborhood. Oakland Park is not just a place to live; it’s a lifestyle that encourages connection and outdoor enjoyment.

One of the standout features of Oakland Park is its commitment to creating a pedestrian-friendly environment. The community boasts beautifully designed sidewalks that meander through the neighborhood, perfect for morning strolls, evening jogs, or leisurely bike rides. Families will love the safe and inviting atmosphere, where children can play freely and neighbors can engage in friendly conversations.

The homes in Oakland Park are thoughtfully crafted, offering a variety of styles and sizes to suit every taste. Each residence is designed with modern amenities and energy-efficient features, ensuring comfort and sustainability. The lush landscaping and well-maintained exteriors create an appealing aesthetic that enhances the charm of the community.

Living in Oakland Park means you’re just moments away from Winter Garden’s vibrant downtown, where you can explore local shops, dine at delightful eateries, and enjoy community events throughout the year. Plus, with easy access to major highways, you’re never far from the excitement of Orlando and its world-renowned attractions.

Discover the allure of Oakland Park, where community spirit flourishes, and every day feels like a getaway. Come home to a place that truly embodies the essence of Florida living!

Newest Oakland Park Homes with Sidewalks Community Features

$595,000

3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained, move-in ready 3-bedroom, 3-bathroom home in the highly sought-after Oakland Park community of Winter Garden. Combining timeless architecture with modern upgrades, this turnkey home offers the perfect blend of comfort, style, and convenience. Inside, you'll find a bright, open-concept floor plan with abundant natural light, soaring ceilings, spacious living and dining areas, and a flexible layout ideal for entertaining, working from home, or accommodating multigenerational living. The chef-inspired kitchen features desirable gas appliances, generous counter space, ample cabinetry, and seamlessly connects to the main living areas, creating the heart of the home. Thoughtful upgrades throughout include plantation shutters, designer finishes, and quality craftsmanship, providing a low-maintenance lifestyle that allows you to simply move in and enjoy. The spacious primary suite offers a private retreat with a luxurious ensuite bathroom and generous walk-in closet, while the additional bedrooms and bathrooms provide flexibility for family, guests, or a dedicated home office. Step outside and enjoy Oakland Park's signature charm, featuring tree-lined streets, inviting front porches, scenic green spaces, and resort-style amenities that foster a true sense of community. Perfectly located just minutes from Historic Downtown Winter Garden, the award-winning Farmers Market, the West Orange Trail, boutique shopping, popular restaurants, community events, and convenient access to SR 429, the Florida Turnpike, Disney, downtown Orlando, and Orlando International Airport. Families will appreciate the proximity to top-rated schools and nearby parks. Whether you're searching for a primary residence, a second home, or simply a home that offers an exceptional lifestyle in one of Central Florida's most desirable communities, this Oakland Park gem delivers the location, upgrades, and quality you've been waiting for.

914 Trowman Alley, Winter Garden

$2,098,000

4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code

Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The lot affords beautiful views of Lake Apopka on a secluded cul-de-sac. The community is conveniently located minutes away from downtown Winter Garden, with a plethora of restaurants, shopping, and more. If outdoor recreation is up your alley, enjoy the various walking trails in the community or explore the 22-mile paved West Orange Trail connecting Oakland/Winter Garden to Apopka! Seize your opportunity to become a part of the luxury lifestyle inside Oakland Park with its multiple community living spaces, pools, playgrounds, and more. Don't settle for a community or home that doesn't have your wants and needs; build this home one to your specifications. Call us to find out more!

1258 Ridge Lake Way, Oakland

Start Your Search