8 WINTERS LANDING DRIVE Oakland, FL $ 885,000
8 WINTERS LANDING DRIVE
$ 885,000
Recently Listed
Open House 3/28 11am - 2pm
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8 WINTERS LANDING DRIVE

Oakland, FL, 34787
$ 885,000
Bedrooms4 Baths3.0 Sq 2,850

Monthly Estimate*

$ 5,449

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Single Family Home for sale in Oakland, FL

for $885,000 with 4 bedrooms and 3 full baths. This 2,850 square foot home was built in 2005 on a lot size of 0.32.

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 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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Open House

3/28/2026 11:00 AM - 2:00 PM
3/29/2026 12:00 PM - 3:00 PM
8 WINTERS LANDING DRIVE Oakland, FL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 885,000

Bedrooms

4

Full Bath

3

Property Type

Single Family

Taxes

$ 3,979

Style

Florida

Lot Size

0.32

Year Built

2005

Town/City

Oakland

County/Region

Orange

MLS | Web ID

O6385221

Features
General
Sewer Septic Tank
Heating Central
Cooling Central Air
Utilities Cable Available Electricity Available Fire Hydrant Natural Gas Available Sprinkler Recycled Street Lights
Roof Shingle
Appliances Bar Fridge Dishwasher Disposal Dryer Electric Water Heater Exhaust Fan Freezer Microwave Range Range Hood Refrigerator Washer
Zoning R-1A
HOA Fee 220
Garage Spaces 3
Patio/Porch Features Front Porch Patio Rear Porch
Architectural Style Florida
Security Features Fire Alarm
Construction Materials Block Stucco
Pets Allowed Yes
Year Built 2005
Levels One
Property Subtype Single Family Residence
Tax Year 2024
Ownership Fee Simple
Accessibility Accessible Entrance
Assoc Fee Paid Per Quarterly
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name WINTERS LNDG PH 01 A D F & G
Facing Direction West
Garage Y/N true
Total Rooms 13
Full Baths 3
Status Active
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
High School West Orange High
City OAKLAND
Association Name Southwest Property Management
Senior Community Y/N false
MLS Area 34787 - Winter Garden/Oakland
Lot Size Units Square Feet
Lot Size Square Feet 13742
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Elementary School Tildenville Elem
Land Lease Y/N false
Tax Annual Amount 3979
Middle/Junior High School Lakeview Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6385221
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 53
Legal Description WINTERS LANDING PHASE 1 60/17 LOT 53
Minimum Lease 8-12 Months
Water Access Y/N false
Monthly HOA Amount 73.33
Additional Rooms Attic Den/Library/Office Family Room Formal Dining Room Separate Formal Living Room Separate
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities 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
Flooring Brick/Stone Carpet Ceramic Tile
Furnished Y/N Unfurnished
Air Conditioning Y/N true
Heating Y/N true
Window Features Shutters
Fireplace Y/N false
Half Baths 0
Laundry Features Electric Dryer Hookup Inside Laundry Room Washer Hookup
Total Bedrooms 4
Total Baths 3
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Exterior
Exterior Amenities Irrigation System Sidewalk
Vegetation Mature Landscaping Trees/Landscaped
Fencing Fenced Other
Parking Features Driveway Garage Door Opener
Lot Features Conservation Area Sidewalk
Water Source Public
Lot Size Area 13742
Foundation Details Slab
Building Area Total 3679
Lot Size Acres 0.32
Road Surface Type Paved Asphalt
Private Pool false
Waterfront Y/N false
Covered Spaces 3
Road Frontage Type Street Paved
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* Excluded Features
List By
Regency Real Estate Llc

Broker

Daniellethatcher@yahoo.com

Email

Affordability Calculator

$5,781
Per Month
94%
6%
0%
Monthly Principal & Interest
$5,449
Monthly Property Taxes
$332
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
West Orange High High School High School
Pricing History
DatePricePrice ChangeDescription
3/25/2026$885,000 Listed Price

Map


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8 WINTERS LANDING DRIVE, Oakland, FL, 34787 is a Single Family Home for sale at $885,000 with 2,850 sqft and a lot size of 0.32. 8 WINTERS LANDING DRIVE has 4 bedrooms, 3.0 baths, and was built in 2005. The property's zip code is 34787 which is in Oakland, FL