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500 W Oakland Avenue

Oakland, FL 34760

3 beds
2 baths
1,336 sqft
3,746 sqft lot
$288 per sqft
2010 build
– on site

Discover the charm of this custom-built home, completed in 2010, with no HOA! Step inside this spacious two-story, 3-bedroom, 2-bathroom home and fall in love with the open floor plan and modern updates. The brand-new flooring and fresh interior paint create a bright, clean, and welcoming feel throughout. The heart of the home is the completely renovated chef’s kitchen, featuring all-new cabinets, sleek countertops, and modern appliances—perfect for anyone who loves to cook or entertain. Enjoy the flexibility of a main-level bedroom and full bathroom, ideal for guests, multigenerational living, or a private home office. Upstairs, you’ll find two additional bedrooms and another full bathroom, offering comfort and privacy for the whole family. Set on a peaceful, nature-filled corner lot, this home provides a serene retreat just steps from the outdoors. Adventure is never far away—the nearby Oakland Nature Preserve invites you to explore scenic walking trails, enjoy educational programs, or relax with tranquil water views from your boat or the dock. When you’re craving a little more buzz, Historic Downtown Winter Garden is just a golf cart ride away. Enjoy brunch at a local café, browse charming boutiques, or spend your Saturday at the award-winning farmers market. The area is alive with family-friendly events, live music, and unforgettable community vibes. Families love Oakland for its warm, small-town feel and top-rated public schools, including the highly acclaimed Oakland Avenue Charter School—a true gem in the community. Whether you’re biking along scenic paths, strolling to the lake, or commuting into Orlando, Oakland offers the perfect blend of small-town charm and big-city access. Unbeatable location with quick access to the Florida Turnpike and SR 429, making it easy to reach Downtown Orlando, Disney World, and beyond. Don’t miss this rare opportunity to own your own piece of paradise. Schedule your private showing today and come see all this beautiful home has to offer!

Listing courtesy of STELLAR_MLS / EXP REALTY LLC

Last checked: Checking… • Last updated Jun 13, 2025 •

MLS# O6312611 —

The Building

Year Built:

2010
New Construction:

false
Construction Materials:

Block
Levels:

Two
Stories Total:

2
Roof:

Shingle
Foundation Details:

Slab
Window Features:

Blinds
Building Area Total:

1641
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Ceiling Fan(s)
Flooring:

Ceramic Tile
Fireplace:

false

Room Dimensions

Living Area:

1336
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

From downtown Winter Garden, head west on Plant Street. Pass the roundabout at Dillard Street and continue straight. Plant Street becomes Oakland Avenue as you enter the town of Oakland. Keep going west for about 2 miles. You’ll pass the Oakland Nature Preserve entrance on your left. Shortly after, look for 500 W Oakland Ave on the right—it’s near the West Orange Trail and the old Oakland Town Hall area.
Latitude:

28.555074
Longitude:

-81.634099
Coordinates:

-81.634099, 28.555074

The Property

Parcel Number:

202227610867010
Property Type:

Residential
Property Subtype:

Single Family Residence
Lot Features:

Corner Lot
Lot Size Acres:

0.09
Lot Size Area:

3746
Lot Size SqFt:

3746
Lot Size Units:

Square Feet
Total Acres:

0 to less than 1/4
Zoning:

R-1
Direction Faces:

North
View:

false
Exterior Features:

Other
Water Source:

Public
Road Surface Type:

Asphalt
Flood Zone Code:

X
Additional Parcels:

false
Homestead:

false
Lease Restrictions:

false
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

1
Tax Block:

H
Tax Legal Description:

PLAT OF THE TOWN OF OAKLAND B/99 LOTS 1BLK H
Tax Book Number:

B-99
Tax Annual Amount:

$3,975

Beds

Bedrooms Total:

3

Baths

Total Baths:

2
Total Baths:

2
Full Baths:

2

The Listing

Virtual Tour URL Branded:

https://topajent.my.canva.site/500-w-oakland
Virtual Tour URL Unbranded:

https://media.devoredesign.com/sites/gemrbgw/unbranded
Special Listing Conditions:

None

Heating & Cooling

Heating:

Central
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

Cable Available
Sewer:

Septic Tank

Appliances

Appliances:

Dishwasher
Laundry Features:

Laundry Closet

The Community

Subdivision Name:

OAKLAND TOWN
Senior Community:

false
Waterview:

false
Water Access:

false
Waterfront:

false
Pool Private:

false
Association:

false
Ownership:

Fee Simple

Parking

Garage:

true
Attached Garage:

true
Garage Spaces:

1
Carport:

false
Covered Spaces:

1
Open Parking:

true
Parking Features:

Driveway

Monthly cost estimate

Asking price

$385,000

Expense	Monthly cost
Mortgage	$2,061
Taxes	$331
Insurance	$105
Utilities	$149 See report
Total	$2,646/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
5/27/25 May 27, 2025	Listed / Active	STELLAR_MLS	$385,000	24.6% (19.2% / YR)
2/14/24 Feb 14, 2024		STELLAR_MLS	$309,000
1/17/24 Jan 17, 2024		STELLAR_MLS	$309,000

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Similar sold homes

This house located in Oakland, FL 34760 is currently for sale for $385,000. 500 W Oakland Avenue is a 1,336 square foot house with 3 beds and 2 baths that has been on Estately for 23 days. This house is in the attendance area of Tildenville Elementary School, West Orange High School, Cornerstone Charter Academy High School, Cornerstone Charter Academy K-8, and Lakeview Middle School.

Listing Courtesy of: STELLAR_MLS and EXP REALTY LLC.

Based on information from the My Florida Regional MLS DBA Stellar MLS 2025.

All information provided is deemed reliable but is not guaranteed and should be independently verified. Stellar MLS, Estately and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. Stellar MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. For any questions please call (407) 499-8911.