Oakland Park Homes with Community Mailbox Community Features

Welcome to Oakland Park, a charming subdivision located in Winter Garden, FL. This family-friendly community is nestled in Orange County and offers a tranquil and inviting atmosphere for residents to call home.

One of the standout features of Oakland Park is its Homes with Community Mailbox Community. This feature not only adds convenience for residents but also fosters a sense of community and connection among neighbors. Imagine strolling down the tree-lined streets to collect your mail, greeting familiar faces along the way, and feeling a true sense of belonging.

In addition to the Homes with Community Mailbox Community, residents of Oakland Park can enjoy a range of amenities and features within the neighborhood. From beautifully landscaped common areas to recreational facilities, there is something for everyone to enjoy. Whether you prefer relaxing by the community pool, taking a leisurely walk along the scenic trails, or gathering with neighbors for social events, Oakland Park has it all.

With its prime location in Winter Garden, residents of Oakland Park have easy access to top-rated schools, shopping, dining, entertainment, and outdoor activities. The community is also just a short drive away from major highways, making it convenient for commuting to work or exploring the surrounding areas.

Come and discover the beauty and warmth of Oakland Park, where homes with community mailboxes and a true sense of community await you. Experience the best of Florida living in this picturesque subdivision in the heart of Orange County.

Newest Oakland Park Homes with Community Mailbox 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 Oakland Park, one of Winter Garden’s most desirable communities. Offering a blend of classic architecture, modern updates, and an exceptional location, this turnkey Winter Garden home is designed for comfortable Florida living. Step inside to a bright and spacious open-concept floor plan featuring abundant natural light, soaring ceilings, and generously sized living and dining areas. The flexible layout is ideal for entertaining, working from home, or accommodating guests. At the center of the home is the chef-inspired kitchen, featuring natural gas appliances, ample cabinetry, generous counter space, and an open connection to the main living areas. Whether you're preparing a weeknight dinner or entertaining friends and family, this kitchen is both functional and inviting. The spacious primary suite provides a private retreat with a luxurious ensuite bathroom and generous walk-in closet. Two additional bedrooms and bathrooms offer plenty of flexibility for family, guests, a home office, or additional living space. Throughout the home, you'll find plantation shutters, designer finishes, and quality upgrades that create a polished yet comfortable atmosphere. With thoughtful improvements already in place, you can move in and start enjoying the lifestyle this home and community have to offer. And then there's Oakland Park. Residents have access to an impressive collection of resort-style community amenities, including TWO community pools, beautiful green spaces, parks, playgrounds, walking paths, gathering areas, and the neighborhood’s iconic tree-lined streets and welcoming front porches. Oakland Park is designed to create a true neighborhood feel while offering the amenities buyers want from a premier Winter Garden community. Location is hard to beat. You're just minutes from Historic Downtown Winter Garden, the popular Winter Garden Farmers Market, the West Orange Trail, local restaurants, boutique shopping, parks, and year-round community events. Convenient access to SR 429 and the Florida Turnpike makes commuting throughout Central Florida easy, while Disney, downtown Orlando, and Orlando International Airport are all within a manageable drive. If you're searching for a move-in ready home in Winter Garden, a community with resort-style amenities and pools, or a home close to Downtown Winter Garden and the West Orange Trail, this Oakland Park property checks the boxes. Experience the charm, convenience, and lifestyle that make Oakland Park one of Winter Garden's most sought-after communities.

914 Trowman Alley, Winter Garden

$859,000

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

OAKLAND PARK---a PARADE of HOMES winning community! Nestled beneath a canopy of mature trees and perfectly positioned across from a PARK, this charming home welcomes you with a spacious covered front porch where you can relax and enjoy nature and the peaceful surroundings. Thoughtfully designed with warmth and character throughout, the home features rich WOOD flooring, beautiful custom ACCENT WALLS, and a stunning staircase that adds style and sophistication to the inviting interior. Offering 3 bedrooms, 2.5 baths, a dedicated formal dining space, and a small bonus area upstairs suitable for an OFFICE—-a functional yet elegant layout, this home was designed with the homeowner in mind. The kitchen is beautifully appointed with stone countertops, tile backsplash, abundant cabinetry, and a built-in desk area that adds both charm and convenience. A dedicated COFFEE BAR creates the perfect morning retreat, while the walk-in pantry and additional secondary pantry provide exceptional storage space. The downstairs spacious laundry room is equally impressive, featuring a utility sink and extensive counter space ideal for organization and everyday functionality. The living room is embraced with natural light from an abundance of windows overlooking the backyard, while extended FRENCH DOORS create a seamless connection to the covered outdoor living space, enhancing the home’s warm and welcoming atmosphere. A convenient half bath and entry door are located adjacent to the covered porch, offering seamless indoor-outdoor living. The outdoor space is already enhanced with pavers, creating a polished and low-maintenance setting ideal for entertaining, relaxing, or future customization. With ample room to design and build a POOL, the backyard offers endless possibilities to create your dream oasis. The upstairs PRIMARY SUITE offers a relaxing retreat complete with dual sinks, an oversized walk-in shower, linen closet, a separate private water closet, and a generously sized walk-in closet. Two additional bedrooms and one full bath are located upstairs. Blending comfort, charm, and thoughtful design, this beautifully customized home offers an exceptional opportunity to enjoy cozy living spaces, stunning outdoor potential, and timeless character in a picturesque PARK setting. Just a short GOLF CART ride away, you’ll find the charm and vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails, including access to the 22 mile long WEST ORANGE TRAIL. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks!

907 Easley Avenue, Winter Garden

Start Your Search