Skip To Content

8 Winters Landing Drive

Oakland, FL 34787
  • $885,000
  • STATUS: Active
  • ON SITE: 22 Days
  • MLS #: O6385221
$885,000
  • 4
    BEDS
  • 0.32
    ACRES
  • 3
    BATHS
  • 0
    1/2 BATHS
  • 2,850
    SQFT
  • $311
    $/SQFT
Type:
Single-Family Home
Built:
2005
County:

School Information

Elementary School:
Middle School:
High School:

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), 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**

Monthly Payment Calculator




© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-04-16T23:47:08.463.
www.endlesssummerlivingfl.com/homes/174426607
Print Image

8 Winters Landing Drive Oakland, FL 34787

  • Price: $885,000
  • Status: Active
  • On Site: 22 Days
  • MLS #: O6385221
4
Beds
3
Baths
0
½ Baths
0.32
Acres
2,850
SQFT
$311
$/SQFT
2005
Built
Neighborhood:
Winters Lndg Ph 01 A D F & G
County:
Orange
Area:
Winter Garden/Oakland
Elementary School:
Tildenville Elem
Middle School:
Lakeview Middle
High School:
West Orange High
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), 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**
Exterior Features

Architectural Style Florida Attached Garage Yn Yes Carport Yn No Construction Materials BlockStucco Covered Spaces 3 Direction Faces West Exterior Features Irrigation SystemSidewalk Fencing FencedOther Foundation Details Slab Lot Features Conservation AreaSidewalk Open Parking YN Yes Parking Features DrivewayGarage Door Opener Patio And Porch Features Front PorchPatioRear Porch Pool Private Yn No Road Frontage Type Street Paved Road Surface Type PavedAsphalt Roof Shingle Water Access Yn No Water Extras Yn No Water View Yn No Waterfront Feet Total 0 Waterfront Yn No

Interior Features

Accessibility Features Accessible Entrance Additional Rooms AtticDen/Library/OfficeFamily RoomFormal Dining Room SeparateFormal Living Room Separate Appliances Bar FridgeDishwasherDisposalDryerElectric Water HeaterExhaust FanFreezerMicrowaveRangeRange HoodRefrigeratorWasher Building Area Total 3679 Cooling Central Air Cooling YN Yes Fireplace Yn No Flooring Brick/StoneCarpetCeramic Tile Furnished Unfurnished Heating Central Heating YN Yes Interior Features Ceiling Fan(s)Crown MoldingDry BarEating Space In KitchenHigh CeilingsKitchen/Family Room ComboOpen FloorplanPrimary Bedroom Main FloorStone CountersThermostatWalk-In Closet(s)Window Treatments Laundry Features Electric Dryer HookupInsideLaundry RoomWasher Hookup Levels One Sewer Septic Tank Water Source Public Window Features Shutters

Property Features

Association Approval Required Yn No Association Fee 220 Association Fee Frequency Quarterly Association Fee Monthly Amount 73.33 Association Fee Requirement Required Association Yn Yes Cdd Yn No Down Payment Resource No Flood Zone Code X Garage Yn Yes Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN No Listing Terms CashConventionalFHAVA Loan Minimum Lease 8-12 Months New Construction Yn No Number Of Septics 1 Ownership Fee Simple Pets Allowed Yes Property Sub Type Single Family Residence Realtor Info As-Is Required Remarks One or more photo(s) has been virtually staged. Security Features Fire Alarm Senior Community Yn No Special Listing Conditions None Tax Annual Amount 3979 Total Annual Fees 880 Total Monthly Fees 73.33 Utilities Cable AvailableElectricity AvailableFire HydrantNatural Gas AvailableSprinkler RecycledStreet Lights Yrs Of Owner Prior To Leasing Re No Zoning R-1A


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of REGENCY REAL ESTATE LLC: 407-469-5021.



© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-04-16T23:47:08.463.
 
https://bt-photos.global.ssl.fastly.net/mfr/orig_boomver_1_O6385221-2.jpg https://bt-photos.global.ssl.fastly.net/mfr/orig_boomver_1_O6385221-2.jpg https://bt-photos.global.ssl.fastly.net/mfr/orig_boomver_1_O6385221-2.jpg
Logo
The Campbell Group | Compass
1575 Main St
Sarasota FL, 34236