Browse Downtown Oakland Homes for Sale in Winter Garden, FL. Discover community amenities, nearby attractions, schools, and the lifestyle this neighborhood offers.
Downtown Oakland Homes for Sale
Downtown Oakland Home for Sale
Downtown Oakland – Winter Garden
Downtown Oakland is a historic, non-gated community of single-family homes located off Oakland Avenue, just north of Hwy 50 (Colonial Drive) in the northwest section of Winter Garden. Homes in Downtown Oakland date back as far as 1886, with new construction continuing through the present day, creating a unique blend of historic charm and modern living.
This area offers a small-town feel with a walkable layout, while still being close to Downtown Winter Garden and major roadways that connect residents to Orlando, the Florida Turnpike, SR 429, and Clermont. Proximity to both Lake Apopka and Johns Lake makes Downtown Oakland especially appealing to outdoor and boating enthusiasts.
Downtown Oakland Neighborhood Amenities
Downtown Oakland features varied HOA structures depending on the section of the neighborhood. Common amenities may include:
• Parks
• Playgrounds
• Community pool
• Sidewalks
• Tennis courts
• Water access
• Fishing areas
Where is Downtown Oakland in Winter Garden?
Zip Code: 34787
Area: Western Oakland area of Winter Garden
North: Lake Apopka
South: Johns Lake
East: Downtown Winter Garden area
West: Clermont community
What’s Around & Nearby?
Grocery & Restaurants: West Point Commons
Mall: Winter Garden Village
Hospital: AdventHealth Winter Garden
Schools: Orange County Find My School
Attractions: Walt Disney World & Universal Studios
Get Out & Play: West Orange Trail
Local Hangout: Downtown Winter Garden
Closest Beach: Cocoa Beach
Typical Downtown Oakland Home Features
Home features in Downtown Oakland are common but may vary by property:
Builders: Various builders
Architectural Styles: Ranch, Contemporary, Farmhouse, Florida, Traditional, Custom
Bedrooms: 2–7
Garage Spaces: 0–4
Living Area: Approx. 600–5,000 sq ft
Interior Rooms: Den/library/office, bonus room, breakfast room (separate), family room
Average Lot Size: Zero lot line to 1 acre
Construction: Shingle & tile
Roof: Shingle & tile
Exterior Features: Sliding doors, irrigation system, sidewalks, fenced yards, rain gutters, French doors, balconies
Thinking about a home in Downtown Oakland?
Call or text the Jared Jones Real Estate Team at 407-706-5000 to learn more today!
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
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
504 W Plant Street, 1st and 2nd Floors, Winter Garden Fl 34787
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