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OAKLAND, FL 34787 8 WINTERS LANDING DRIVE

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Presented By: REGENCY REAL ESTATE LLC with 407-469-5021. - 407-469-5021
  • MLS# O6385221
  • 03/25/2026
  • Request Tour
  • Request Info
  • Beds • 4
  • Baths • 3
  • SQFT • 2,850
  • Garage • 3

Home Details

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**
Presented By: REGENCY REAL ESTATE LLC with 407-469-5021. - 407-469-5021

Interior Features for 8 WINTERS LANDING DRIVE

Bedrooms

Total Bedrooms4

Bathrooms

Half Baths0
Total Baths3

Other Interior Features

LivingAreaSourcePublic Records
Air Conditioning Y/NYes
Fireplace Y/NNo
FlooringBrick/Stone, Carpet, Ceramic Tile
Furnished Y/NUnfurnished
Heating Y/NYes
Interior AmenitiesCeiling 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 FeaturesElectric Dryer Hookup, Inside, Laundry Room, Washer Hookup
Window FeaturesShutters

General for 8 WINTERS LANDING DRIVE

AccessibilityAccessible Entrance
Additional Parcels Y/NNo
Additional RoomsAttic, Den/Library/Office, Family Room, Formal Dining Room Separate, Formal Living Room Separate
AppliancesBar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Microwave, Range, Range Hood, Refrigerator, Washer
Architectural StyleFlorida
Assoc Fee Paid PerQuarterly
Association NameSouthwest Property Management
Attached Garage Yes
Building Area UnitsSquare Feet
Carport Y/NNo
CityOAKLAND
Construction MaterialsBlock, Stucco
CoolingCentral Air
CountyOrange
DirectionsHead 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
Elementary SchoolTildenville Elem
Facing DirectionWest
Flood Zone CodeX
Flood Zone Code XY
Full Baths3
Garage Spaces3
Garage Y/NYes
HOA Fee$220
HeatingCentral
High SchoolWest Orange High
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionWINTERS LANDING PHASE 1 60/17 LOT 53
LevelsOne
Listing TermsCash, Conventional, FHA, VA Loan
Living Area UnitsSquare Feet
Lot Size Square Feet13742
Lot Size UnitsSquare Feet
MLS Area34787 - Winter Garden/Oakland
Middle/Junior High SchoolLakeview Middle
Minimum Lease8-12 Months
Monthly HOA Amount73.33
New ConstructionNo
Occupancy TypeOwner
OwnershipFee Simple
Patio/Porch FeaturesFront Porch, Patio, Rear Porch
Pets AllowedYes
Property SubtypeSingle Family Residence
Property TypeResidential
RoofShingle
STELLAR_InLawSuiteYNNo
Security FeaturesFire Alarm
Senior Community Y/NNo
SewerSeptic Tank
Standard StatusActive
StatusActive
Subdivision NameWINTERS LNDG PH 01 A D F & G
Tax Annual Amount3979
Tax Lot53
Tax Year2024
Total Rooms13
UtilitiesCable Available, Electricity Available, Fire Hydrant, Natural Gas Available, Sprinkler Recycled, Street Lights
Virtual TourClick here
Water Access Y/NNo
Water View Y/NNo
Year Built2005
ZoningR-1A

Exterior for 8 WINTERS LANDING DRIVE

Building Area Total3679
Covered Spaces3
Exterior AmenitiesIrrigation System, Sidewalk
FencingFenced, Other
Foundation DetailsSlab
Lot FeaturesConservation Area, Sidewalk
Lot Size Acres0.32
Lot Size Area13742
Parking FeaturesDriveway, Garage Door Opener
Private PoolNo
Road Frontage TypeStreet Paved
Road Surface TypePaved, Asphalt
VegetationMature Landscaping, Trees/Landscaped
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Steven Silcock

Broker Owner
Price $885,000
MLS#O6385221
List Date 03/25/2026
Property Type Single Family
Phone 407.574.0218
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