Downtown Oakland Homes for Sale
Under Construction. This exceptional luxury residence by Element Home Builders is located in the prestigious Briley Farm community and offers 5,144 square feet of thought...
- 6 Beds
- 7 Baths
- Briley Farm SubDv.
- 34760 Zip Code
Under Construction. Introducing one of Central Florida's most distinguished new addresses — the Oakshade floor plan by award-winning Davila Homes, nestled within the excl...
- 6 Beds
- 7 Baths
- Grove/Oakland SubDv.
- 34787 Zip Code
Pre-Construction. To be built. Welcome home to The Wildflower, an exquisitely crafted new construction estate nestled within the exclusive community of The Grove in charm...
- 5 Beds
- 7 Baths
- Grove/Oakland SubDv.
- 34787 Zip Code
Nestled beneath century-old heritage oaks in one of Oakland's most coveted addresses, this stunning 4,433 square foot Citrus floorplan by Element Home Builders delivers a...
- 5 Beds
- 8 Baths
- Grove/Oakland SubDv.
- 34787 Zip Code
Pre-Construction. To be built. Introducing the Sunburst Model by Davila Homes Discover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautif...
- 5 Beds
- 6 Baths
- Grove At The Harvest District SubDv.
- 34787 Zip Code
Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a...
- 5 Beds
- 6 Baths
- Grove At The Harvest District SubDv.
- 34787 Zip Code
Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that show...
- 5 Beds
- 6 Baths
- Grove At The Harvest District SubDv.
- 34787 Zip Code
FRONT PORCH CHARM, WEST ORANGE TRAIL VIEWS, AND A HOME FULL OF CHARACTER IN THE HEART OF OAKLAND! Start your mornings from the covered front porch and porch swing, taking...
- 4 Beds
- 4 Baths
- Town/Oakland SubDv.
- 34760 Zip Code
PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would al...
- 6 Beds
- 8 Baths
- Oakland SubDv.
- 34760 Zip Code
Discover an exceptional opportunity to build a custom lakefront residence on Lot 45 in Briley Farm Phase 1B. Located at 552 Walker Street in Oakland, this approximately 0...
- Briley Farm Ph 1b SubDv.
- 34787 Zip Code
Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, ...
- 4 Beds
- 3 Baths
- Oakland Town SubDv.
- 34760 Zip Code
Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where ch...
- 5 Beds
- 3 Baths
- Oakland Pointe SubDv.
- 34760 Zip Code
NEW PRICE IMPROVEMENT! Seller incentive available! Welcome home to this beautiful 2026 newly built residence in the desirable town of Oakland! This 4-bedroom, 2.5-bath...
- 4 Beds
- 3 Baths
- Oakland Town SubDv.
- 34760 Zip Code
Build your custom residence on Lot 21 in Briley Farm Phase 1B, a thoughtfully designed community in Oakland, Florida. Located at 523 Walker Street, this approximately 0.5...
- Briley Farm Ph 1b SubDv.
- 34787 Zip Code
Briley Farm, Central Florida’s newest custom home community, sits on 111 acres of lush landscape in Oakland, Florida. Here, you’ll have the opportunity to build your drea...
- Briley Farm SubDv.
- 34787 Zip Code
PRICE REDUCED - Accepting Offers! The home has recently been entirely staged on the inside of the property - come tour this BEAUTY! NOTE: to add extra storage, a (larg...
- 3 Beds
- 2 Baths
- Oakland Town SubDv.
- 34760 Zip Code
Home › Central Florida › Orlando Metro › Orange County › 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
Text Downtown Oakland to 321.384.5738 for more info!
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David Myers
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