Downtown Oakland Homes for Sale

16251 W Colonial Drive, Oakland $2,400,000 ▲

PRIME LOCATION HWY 50 FRONTAGE. This C-1 Zoned 3.52 +/- acres is right near the border of booming Winter Garden (population 48,000) and just East of Clermont (population ...

34760 Zip Code

402 E Gulley Avenue, Oakland $1,495,000

One or more photo(s) has been virtually staged. Pre-Construction. To be built. No HOA! Direct access to the West Orange Trail! Minutes from Downtown Winter Garden’s shops...

4 Beds
3.5 Baths
Oakland Heights SubDv.
34760 Zip Code

16 Oakland Pointe Circle, Oakland $699,999

One or more photo(s) has been virtually staged. Come see this one-of-a-kind, beautiful 5-bedroom, 3-bathroom custom built home on a 0.3-acre corner lot in the heart of qu...

5 Beds
3 Baths
Oakland Pointe SubDv.
34760 Zip Code

390 W Gulley Avenue, Oakland $475,000

Country Charmer close to Everything! This home is located on the West Orange Trail in the quaint town of Oakland. This 3 Bedroom/2 Bath home has been remodeled from top t...

3 Beds
2 Baths
Oakland Town SubDv.
34760 Zip Code

401 W Herriott Avenue, Oakland $329,500 ▼

Brand New colonial styled home in the heart of Oakland, Florida. Built entirely in 2022 and completed in August 2022. Spacious kitchen with gorgeous Brazilian granite cou...

2 Beds
2 Baths
Oakland Town SubDv.
34760 Zip Code

Winter Garden › Downtown Oakland

Downtown Oakland - Winter Garden

Downtown Oakland is a Winter Garden neighborhood of non-gated, Single Family Homes off Oakland Ave just North of Hwy 50 in the Northwest section of Winter Garden. The majority of the homes in Downtown Oakland were built 1886 to Current Day by Various Builders.

The Downtown Winter Garden is nearby as is an entrance to Hwy 50/Colonial Drive which will take you East to the Florida Turnpike, the 429 Expressway and Downtown Orlando or West to Clermont.

Downtown Oakland Neighborhood Amenities

There is varies HOA for Downtown Oakland which includes the following amenities:

Park
Playground
Pool
Sidewalks
Tennis Courts
Water Access
Fishing

Where is Downtown Oakland in Winter Garden?

Downtown Oakland is located in the 34787 zip code in the Western Oakland Area of Winter Garden.

The Downtown Oakland neighborhood is bordered by Lake Apopka to the North, Johns Lake to the South, Downtown Winter Garden Area to the East, and the Clermont Community to the West.

What's Around & Near Downtown Oakland?

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: The West Orange Trail
Local Hang Out: Downtown Winter Garden
Closest Beach: Cocoa Beach

Typical Downtown Oakland Home Features

Downtown Oakland included home features below are common but may vary from home to home:

Builder(s): various builders
Architectural Style(s): Ranch, Contemporary, Farmhouse, Florida, Traditional, Custom
Number of Bedrooms:2-7
Number of Garage Spaces: 0-4
Sq Ft Size under Air: Approx 600-5000
Interior Rooms: Den/Library/Office, Bonus Room, Breakfast Room Separate, Family Room
Average Lot Size: zero lot line to 1 acre
Construction Material: Shingle & Tile
Roof: Shingle & Tile
Exterior Features: Sliding Doors, Irrigation System, Sidewalks, Fenced, Rain Gutters, French Doors, Balcony

Schedule your viewing of Downtown Oakland today!