Home in 8 Winters Landing Dr Oakland for sale with MLS# O6385221

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), 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**

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8 Winters Landing Dr, Oakland, FL 34787

Price
Price:
$885,000.00
Original List Price:
$885,000.00
List Price per Sq Ft (Calculated, Approx.):
$310.53
Property Status and Type
Listing Type:
For Sale
Status:
Active
Listing Category:
Residential
Property Type:
Single Family House
MLS Number:
O6385221
Rooms Distribution
Bedrooms:
4
Bathrooms Total:
3
Full Bath:
3
Additional Rooms:
Attic, Den/library/office, Family Room, Formal Dining Room Separate, Formal Living Room Separate
Measures
Living Area:
2,850 Sqft
Built-Up Area:
3,679 Sqft
Lot Area:
13,742 Sqft
Building Area Source:
Public Records
Living Area Source:
Public Records
Lot Features:
Paved, Sidewalk, Conservation Area
Lot Size Acres:
0.32
Property Features
Waterfront:
No
Security:
Fire Alarm
Furnished:
Unfurnished
Accessibility:
Accessible Entrance
Appliances:
Dryer, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Freezer, Electric Water Heater, Exhaust Fan, Range, Range Hood, Bar Fridge
Interior:
Eat-in Kitchen, High Ceilings, Walk-In Closet(s), Ceiling Fans(s), Kitchen/family Room Combo, Open Floorplan, Stone Counters, Thermostat, Window Treatments, Crown Molding, Dry Bar, Primary Bedroom Main Floor
Exterior:
Sidewalk
Patio and Porch:
Patio, Front Porch, Rear Porch
Windows:
Shutters
Laundry:
Washer Hookup, Inside, Laundry Room, Electric Dryer Hookup
Air Conditioning System:
Central Air
Heating System:
Central
Fence:
Other, Fenced
Vegetation and Trees:
Trees/landscaped, Mature Landscaping
Property Entrance Faces:
West
Other Equipment:
Irrigation Equipment
Construction
Year Built:
2005
Roof:
Shingle
Architectural Style:
Florida
Levels:
One
Construction Materials:
Block, Stucco
Flooring:
Carpet, Ceramic Tile, Brick
Foundation Details:
Slab
Flood Zone Code:
X
Taxes and Expenses
Homestead Property
Tax Annual Amount:
$3,979.00
Tax Year:
2024
Association Fee:
$220.00
Association Fee Frequency:
Quarterly
Total Annual Fees:
$880.00
Total Monthly Fees:
$73.33
Parking
Garage
Garage Spaces:
3
Attached Garage
Parking Features:
Driveway, Garage Door Opener
Utilities
Sewer:
Septic Tank
Utilities Available:
Cable Available, Electricity Available, Natural Gas Available, Fire Hydrant, Sprinkler Recycled
Water Source:
Public
Community
Association
Minimum Lease Term:
8-12 Months
Pets Allowed?
Subdivision Name:
WINTERS LNDG PH 01 A D F & G
Community Features:
Street Lights
Senior Community:
No
Association Fee Required:
Required
Association Management:
Southwest Property Management
Association Phone:
407-656-1081
Terms
Listing Terms Considered by Seller:
Cash, Conventional, FHA, VA Loan
Occupant Type:
Owner
Lease Considered:
Yes
Zoning and Legal
Tax Legal Description:
WINTERS LANDING PHASE 1 60/17 LOT 53
Real Estate Folio Number (Parcel Number):
21-22-27-9401-00-530
Zoning:
R-1A
Title to the property is held by owner as:
Fee Simple
Public Schools Assigned
Elementary School:
Tildenville Elem
High School:
West Orange High
Middle Or Junior School:
Lakeview Middle
Listing History
Originally published on:
March 25, 2026 3:30 pm
Active on the market since:
March 25, 2026
Listing Agreement executed on:
March 25, 2026
Listing Status Last Changed On:
March 25, 2026 3:30 pm
Photos updated on:
March 25, 2026 3:32 pm
Last Modified:
April 17, 2026 7:00 pm
Additional Information
Courtesy of:
REGENCY REAL ESTATE LLC
Attribution:
407-469-5021
Road Surface Type:
Asphalt
Location
Street Name:
WINTERS LANDING
Street Number:
8
City:
OAKLAND
State:
Florida
Zip Code:
34787
County:
Orange
Latitude:
N28° 33' 21.4''
Longitude:
W82° 22' 47.7''
Property Map

Neighborhood Stats

Source: U.S. Census Bureau, ACS 5-Year Estimates

Median Household Income $114,988
Median Home Value $475,000
Median Rent $1,994/mo
Median Age 37
Population 93,064

Air Quality

Source: AirNow.gov · Lake County

🌬️ Air Quality Index (AQI) 37 Good
☀️ O3 37 Good

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