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$850,000
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Property Description
One or more photo(s) has been virtually staged. Welcome to your own private retreat in one of West Orange County's most sought-after areas. This completely renovated 4-bedroom, 3-bathroom home offering 2,850 square feet of beautifully updated living space, with a new roof (2025), and drain field (2024), located in the heart of Oakland is just minutes from downtown Winter Garden. From the moment you step inside, you'll appreciate the thoughtful design and elevated finishes throughout. This spacious home features a dedicated office, formal dining room, and formal living room-perfect for entertaining or creating flexible living spaces to fit your lifestyle. The open-concept layout seamlessly connects the kitchen and family room, complete with a cozy breakfast nook ideal for casual dining. The fully renovated interior showcases wood-look tile throughout the main living areas and plush carpet in all bedrooms. Shiplap accent walls and plantation shutters add warmth, character, and timeless charm. Each of the three bathrooms has been uniquely designed, offering its own distinct style and personality. Step outside to your private, fully fenced backyard that backs to a conservation area-ensuring no rear neighbors, ever. Enjoy peaceful views and added privacy in a serene natural setting. This home is less than a 2-minute walk to Oakland Avenue Charter School and sits within the highly desirable golf cart district of downtown Winter Garden-making it easy to enjoy local shops, dining, and community events. **Some of these photos have been virtually staged**
Full Property Details
Full Property Details for 8 Winters Landing Dr
General
- Sold For: $850,000
- HOA FEE: $73/month
- HOA FEE FREQ.: Quarterly
- Taxes: $3,979 (2024)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6385221
- Added to Site: 64 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 13
- Interior Features: Ceiling Fan(s), Crown Molding, Dry Bar, Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Open Floorplan, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
- Appliances: Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Microwave, Range, Range Hood, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Brick/Stone, Carpet, Ceramic Tile
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
Additional Information
- Security/Safety: Fire Alarm
Exterior
- Exterior Features: Irrigation System, Sidewalk
- Deck/Patio: Front Porch, Patio, Rear Porch
- Porch/Patio/Deck: Front Porch, Patio, Rear Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Driveway, Garage Door Opener
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: WINTERS LNDG PH 01 A D F & G
- Driving Directions: Head west from downtown Orlando toward West Colonial Drive (State Road 50). Continue on West Colonial Drive (SR 50) heading west toward Winter Garden. SR 50 is the main east-west road that goes all the way from Orlando into Winter Garden/Oakland. Stay on SR 50 west through Ocoee and into the Winter Garden/Oakland area (about 14–19 miles total from Orlando). Turn right onto Avalon Road (County Road 545) at a traffic signal after passing some commercial areas in Winter Garden/Oakland. At the next traffic light, turn left onto East Oakland Avenue. Continue on East Oakland Avenue for roughly ¾ mile. Turn right onto Winters Landing Drive — the community street where 8 Winters Landing Drive is located. Follow Winters Landing Drive into the neighborhood and arrive at #8 on the right-hand side
- Direction Faces: West
School Information
- Elementary School: Tildenville Elem
- Middle School: Lakeview Middle
- High School: West Orange High
Community
- Community Name: 34787 - Winter Garden/Oakland
- Association: Yes
- Assoc. Name: Southwest Property Management
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Septic Tank
- Water: Public
- Utility Description: Cable TV Available, Electricity Available, Fire Hydrant, Natural Gas Available, Sprinkler Recycled, Street Lights
Structural Information
- Architectural Info: Florida
- Architectural Style: Florida
- Exterior Const.: Block, Stucco
- Roof: Shingle
- Windows: Shutters
- Stories/Levels: One
- Square Feet: 2,850
- Sq. Ft. Source: Public Records
- Living Area: 2,850 Sq. Ft.
- Year Built: 2005
Lot Features
- Lot Size (Acres): 0.32
- Lot Size (Sq. Ft.): 13,742
- Lot Size: 13742
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
- Fencing (Description): Fenced, Other
Financial Considerations
- Association Fee: $220
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $3,979
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: WINTERS LANDING PHASE 1 60/17 LOT 53
- Flood Zone Info: X
- APN: 212227940100530
- Property ID: 212227940100530
Listed by Regency Real Estate Llc
Sold by Charles Rutenberg Realty Orlando
Get Pre-Approved Today
Schools
Schools serving 8 Winters Landing Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Tildenville Elementary School 1221 Brick Road, Winter Garden, FL 34787 | PK-5 | 0.7 mi |
Lakeview Middle School 1200 West Bay Street, Winter Garden, FL 34787 | 6-8 | 1.2 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 3.4 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 8 Winters Landing Dr
Date
Details
Price
Change
Source
5/27/2026
Sold
$850,000
-2.86%
MLS
5/04/2026
Price Reduced
$875,000
-1.13%
MLS
3/25/2026
Listed
$885,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
8 Winters Landing Drive, Oakland, FL 34787 (MLS# O6385221) is a Single Family property that was sold at $850,000 on May 27, 2026. Want to learn more about 8 Winters Landing Drive? 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.

