Oakland Homes for Sale
Oakland Homes for Sale
Browse Oakland homes for sale and discover top neighborhoods, schools, and market trends. Explore listings in a scenic West Orange community along Lake Apopka.
Find Your Dream Home in Oakland
Nestled just west of Winter Garden, Oakland is one of Central Florida’s most charming small towns. Known for its oak-lined streets, historic character, and direct access to the scenic West Orange Trail, Oakland offers a lifestyle that blends small-town charm with quick convenience to Orlando and surrounding areas. Families and professionals alike are drawn to Oakland for its relaxed pace, community feel, and easy access to shopping, dining, and entertainment in nearby Winter Garden.
Location & Lifestyle
Living in Oakland means you’re only about 12–15 minutes from Downtown Winter Garden, with its weekly farmers market, award-winning restaurants, and family-friendly festivals. Outdoor enthusiasts love that the West Orange Trail runs directly through Oakland, making biking, jogging, and weekend walks part of everyday life. The Florida Turnpike and SR-429 are just minutes away, keeping commutes into Orlando and other employment hubs simple and convenient.
If you’re searching for homes for sale in Oakland, you’ll find a mix of charming older homes reflecting the town’s history, alongside newer builds with modern upgrades. Many properties feature large lots, mature trees, and neighborhood layouts that encourage community connections. Typical Oakland homes range from cozy single-family residences in the $400s to larger, newer construction homes that exceed $700K, depending on size, style, and proximity to the trail or downtown areas.
Homes for Sale in Oakland
Community & Amenities
Oakland has a reputation for being welcoming and community-oriented. With several parks, access to top-rated schools, and a network of recreational amenities, it’s an excellent choice for families. The West Orange Trail is a centerpiece of the community, offering 22 miles of paved pathways for cycling, running, and strolling through Central Florida’s natural beauty. Proximity to Lake Apopka also provides opportunities for boating, fishing, and nature exploration.
Winter Garden Areas
Downtown Winter Garden Area Neighborhoods
Winter Garden Village Area Neighborhoods
Estates Lakeview Preserve
Horizon West Area Neighborhoods
Cove At Hamlin
Del Webb Oasis (NEW)
Harvest at Ovation
Mezzano
Osprey Ranch
Westhaven Ovation
Hamlin Pointe
Hamlin Ridge
Horizon Isle
Lake Star at Ovation
Northlake at Ovation
Parkview at Hamlin
Serenade at Ovation
Silverleaf Oaks
Silverleaf Reserve
Tribute at Ovation
Oakland Area Neighborhoods
Johns Landing
Lake Apopka Sound (NEW)
504 W Plant Street, 1st and 2nd Floors, Winter Garden Fl 34787
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