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$367,500
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Property Description
One or more photo(s) has been virtually staged. Charming Renovated Home in the Heart of Historic Oakland! Welcome to 500 W Oakland Avenue, nestled in the storybook town of Oakland, which is celebrated for its Hallmark-like charm and strong sense of community. Located in the desirable 34760 zip code, this beautifully updated two-story home features an open floor plan with thoughtfully designed living space and NO HOA restrictions! You'll fall in love with the bright, clean, and welcoming feel throughout with brand-new flooring and fresh interior paint. 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 with attached an garage plus plenty of parking Residents of the 34760 zip code enjoy the unique charm of mail pickup at the historic Oakland Post Office, where you'll also find the latest issue of the Orange Observer and a quaint Little Free Library out front. Oakland also hosts a variety of beloved community events, including Heritage Day, Santa meet-and-greets, Easter egg drops, and weekly farmers markets in-front of the Heritage Center, an ever changing art gala. The town is a scenic rest stop along the West Orange Bike Trail and is home to numerous parks and landmarks. Speer Park features two playgrounds, tennis, pickleball, and basketball courts. The Jake Voss public fishing pier provides a peaceful spot for watching sunsets on Lake Apopka. Prairie House Coffee serves local coffee, baked goods, floral arrangements, and gifts inside a charming 1860s residence. Disney enthusiasts will love Recycling the Magic, which offers an eclectic shopping experience filled with Walt Disney World props, resort decor, and memorabilia. Just 3.5 blocks from the upcoming boutique district at 300 S. Tubb Street, this location offers walkability to a future hub of shopping, dining, and community spaces-modeled after Winter Garden's beloved Plant Street. Nearby, luxury estate communities like Briley Farm and The Grove are bringing multi-million-dollar homes to Oakland, setting the stage for strong equity growth. This is your chance to own a move-in ready gem in Oakland at an affordable value!
Full Property Details
Full Property Details for 500 W Oakland Ave
General
- Sold For: $367,500
- Taxes: $3,975 (2024)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6312611
- Added to Site: 237 day(s) ago
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 8
- Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Window Treatments
- Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Tankless Water Heater, Washer
- Flooring: Ceramic Tile, Laminate
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Laundry Closet
Exterior
- Exterior Features: Other
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 1
- Covered Spaces: 1
- Parking Features: Driveway, Garage Door Opener, Off Street
Location
- Area: 34760 - Oakland
- County: Orange
- Development Name: 34760 - Oakland
- Subdivision: OAKLAND TOWN
- Driving 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.
- Direction Faces: North
Community
- Community Name: 34760 - Oakland
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Septic Tank
- Water: Public
- Utility Description: Cable TV Available, Cable Connected, Electricity Connected, Phone Available, Water Connected
Structural Information
- Exterior Const.: Block
- Roof: Shingle
- Windows: Blinds
- Stories/Levels: Two
- Square Feet: 1,336
- Sq. Ft. Source: Public Records
- Living Area: 1,336 Sq. Ft.
- Year Built: 2010
Lot Features
- Lot Size (Acres): 0.09
- Lot Size (Sq. Ft.): 3,746
- Lot Size: 3746
- Street/Road Desc.: Asphalt
Financial Considerations
- Tax Amount: $3,975
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: PLAT OF THE TOWN OF OAKLAND B/99 LOTS 1BLK H
- Flood Zone Info: X
- APN: 202227610867010
- Property ID: 202227610867010
- Block/Lot/Section: H
Listed by Dalton Wade Inc
Sold by The C Smith Real Estate Group Llc
Get Pre-Approved Today
Schools
Schools serving 500 W Oakland Ave
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Tildenville Elementary School 1221 Brick Road, Winter Garden, FL 34787 | PK-5 | 1.6 mi |
Lakeview Middle School 1200 West Bay Street, Winter Garden, FL 34787 | 6-8 | 2 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 4.2 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 500 W Oakland Ave
Date
Details
Price
Change
Source
10/27/2025
Sold
$367,500
—
MLS
9/18/2025
Price Reduced
$367,500
-2%
MLS
7/11/2025
Price Reduced
$375,000
-2.6%
MLS
5/27/2025
Listed
$385,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
500 W Oakland Avenue, Oakland, FL 34760 (MLS# O6312611) is a Single Family property that was sold at $367,500 on October 27, 2025. Want to learn more about 500 W Oakland Avenue? Do you have questions about finding other Single Family real estate for sale in Oakland? You can browse all Oakland real estate or contact a Coldwell Banker agent to request more information.

