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**
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**
Property Details
Price:
$885,000
MLS #:
O6385221
Status:
Active
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINTERS LNDG PH 01 A D F & G
Neighborhood:
34787wintergardenoakland
Listed Date:
Mar 25, 2026
Finished Sq Ft:
2,850
Total Sq Ft:
3,679
Lot Size:
13,742 sqft / 0.32 acres (approx)
Year Built:
2005
See this Listing
Schools
Elementary School:
Tildenville Elem
Middle School:
Lakeview Middle
High School:
West Orange High
Interior
Appliances
Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Microwave, Range, Range Hood, Refrigerator, Washer
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Flooring
Brick/Stone, Carpet, Ceramic Tile
Heating
Central
Interior Features
Ceiling Fan(s), Crown Molding, Dry Bar, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
Laundry Features
Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
Levels
One
Exterior
Accessibility Features
Accessible Entrance
Architectural Style
Florida
Attached Garage YN
1
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
West
Exterior Features
Irrigation System, Sidewalk
Fencing
Fenced, Other
Garage Spaces
3
Lot Features
Conservation Area, Sidewalk
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener
Patio And Porch Features
Front Porch, Patio, Rear Porch
Roof
Shingle
Security Features
Fire Alarm
Window Features
Shutters
Financial
HOA Fee
$220
HOA Fee Frequency
Quarterly
HOA Name
Southwest Property Management
HOA Phone
407-656-1081
Tax Year
2024
Taxes
$3,979
Map
Community
- Address8 WINTERS LANDING DRIVE OAKLAND FL
- SubdivisionWINTERS LNDG PH 01 A D F & G
- CityOAKLAND
- CountyOrange
- Zip Code34787
Subdivisions in OAKLAND
- BRILEY FARM
- GROVE AT THE HARVEST DISTRICT
- HULL ISLAND ESTATES FIRST ADD
- JOHNS LANDING
- JOHNS LANDING PH 01 44/47
- JOHNS LANDING PH 02 48 138
- JOHNS LANDING PHASE 1
- LONGLEAF
- LONGLEAF AT OAKLAND
- LONGLEAF/OAKLAND
- LONGLEAF/OAKLAND REP
- OAKLAND PARK
- OAKLAND PK UN 7 NORTH
- OAKLAND TOWN
- OAKLAND TRAILS
- OAKLAND TRAILS PH 1
- OAKLAND TRLS PH 1
- OAKLAND TRLS PH 2
- RYAN COURT
- THE GROVE AT OAKLAND
- WINTERS LNDG PH 01 A D F & G
Market Summary
Current real estate data for Single Family in OAKLAND as of Apr 29, 2026
29
Single Family Listed
71
Avg DOM
346
Avg $ / SqFt
$1,094,585
Avg List Price
Property Summary
- Located in the WINTERS LNDG PH 01 A D F & G subdivision, 8 WINTERS LANDING DRIVE OAKLAND FL is a Single Family for sale in OAKLAND, FL, 34787. It is listed for $885,000 and features 4 beds, 3 baths, and has approximately 2,850 square feet of living space, and was originally constructed in 2005. The current price per square foot is $311. The average price per square foot for Single Family listings in OAKLAND is $346. The average listing price for Single Family in OAKLAND is $1,094,585. To schedule a showing of MLS#o6385221 at 8 WINTERS LANDING DRIVE in OAKLAND, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
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Courtesy of REGENCY REAL ESTATE LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than Charles Rutenberg Realty include the name of the listing broker. Neither the listing company nor Charles Rutenberg Realty shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 8 WINTERS LANDING DRIVE
OAKLAND, FL