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
Horizon West
Winter Garden Village
Downtown Winter Garden Area Neighborhoods
Downtown Winter Garden
Chapin Station
Courtlea Oaks
Courtlea Oaks
Covington Chase
Crown Point Springs
Daniels Crossing
Fullers Crossing
Fullers Landing
Heritage at Plant Street
Island Pointe
Kings Bay
Lake Cove Pointe
Lakeview Reserve
Magnolia Wood
McAllister Landing
Oakglen Estates
Oaks at Brandy Lake
Park Place
Regal Pointe
Stanton Estates
Sterling Pointe
Timbercreek Pines
Traditions
Trails of Winter Garden
Tuscany
Walkers Grove
Winter Oaks
Winter Garden Village Area Neighborhoods
Alexander Ridge
Amberleigh
Avalon Reserve
Avalon Ridge
Banana Bay Estates
Bay Isle
Belle Meade
Black Lake Park
Black Lake Preserve
Bradford Creek
Bronsons Landing
Canopy Oaks
Carriage Pointe
Cobblestone
Country Lakes
Cypress Reserve
Daniels Landing
Deerfield Place
Emerald Ridge
Estates Lakeview Preserve
Foxcrest
Glynwood
Grove Park
Grovehurst
Hickory Hammock
Johns Lake Pointe
Lake Roberts Landing
Orange Cove
The Orchard
Oxford Chase
Regency Oaks
Reserve at Carriage Pointe
Roper Reserve
Sanctuary at Twin Waters
Southern Pines
Stone Creek
Stoneybrook West
Sunset Lakes
Tilden Place
Twinwaters
Waterside
Westfield Lakes
Windermere Crossing
Windward Cay
Wintermere Harbor
Wintermere Pointe
Woodbridge on the Green
Horizon West Area Neighborhoods
Avalon Cove
Cove At Hamlin
Del Webb Oasis (NEW)
Enclave at Hamlin
Encore at Ovation
Hamilton Gardens
Hamlin Reserve
Hawksmoor
Harvest at Ovation
Highland Ridge
Highlands Summerlake
Independence
Isles Of Lake Hancock
Lake Hancock Preserve
Lakeshore
Lakeside at Hamlin
Lakeview Pointe
Lakeview Preserve
Latham Park
Mezzano
Orchard Hills
Orchard Park
Osprey Ranch
Overlook At Hamlin
Panther View
Ravenna
Sanctuary at Hamlin
Storey Grove
Summerlake
Summerlake Groves
Waterleigh
Watermark
Westhaven Ovation
Wincey Groves
Winding Bay
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
Deer Island
Downtown Oakland
Hull Island
Johns Cove
Johns Landing
Lake Apopka Sound (NEW)
Longleaf at Oakland
Oakland Hills
Oakland Park
Oakland Trails
Trailside Station
Tucker Oaks
Verde Park
213 S Dillard St. Suite 320F,
Winter Garden Fl 34787
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