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**
Sold for $850,000
Zestimate®
$850,000
8 Winters Landing Dr, Oakland, FL 34787
4beds
2,850sqft
Single Family Residence
Built in 2005
0.32 Acres Lot
$850,000 Zestimate®
$298/sqft
$3,660 Estimated rent
Home value
$850,000
$782,000 - $918,000
$3,660/mo
Zestimate® history
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List your homeWhat's special
Peaceful viewsNew roofDedicated officeCozy breakfast nookOpen-concept layoutShiplap accent wallsFormal dining room
Zillow last checked:
Listing updated:
Listed by:
Danielle Norvell 512-797-6124,
REGENCY REAL ESTATE LLC 407-469-5021,
Alexis Anderson 561-670-5901,
REGENCY REAL ESTATE LLC
Bought with:
T.J. O'Donnell, 3308706
CHARLES RUTENBERG REALTY ORLANDO
Source: Stellar MLS,MLS#: O6385221
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Rooms
- Room types: Attic, Den/Library/Office, Family Room, Dining Room, Living Room
Primary bedroom
- Features: Ceiling Fan(s), En Suite Bathroom, Wet Bar, Walk-In Closet(s)
- Level: First
- Area: 300 Square Feet
- Dimensions: 12.5x24
Bedroom 1
- Features: Handicapped Accessible, Jack & Jill Bathroom, Single Vanity, Built-in Closet
- Level: First
- Area: 115 Square Feet
- Dimensions: 10x11.5
Bedroom 2
- Features: En Suite Bathroom, Jack & Jill Bathroom, Built-in Closet
- Level: First
- Area: 110.25 Square Feet
- Dimensions: 10.5x10.5
Bedroom 3
- Features: Ceiling Fan(s), Built-in Closet
- Level: First
Primary bathroom
- Features: Claw Foot Tub, Exhaust Fan, Makeup/Vanity Space, Split Vanities, Sunken Shower, Water Closet/Priv Toilet, Window/Skylight in Bath, Linen Closet
- Level: First
Bathroom 1
- Features: Exhaust Fan, Jack & Jill Bathroom, Multiple Shower Heads, Shower No Tub, Single Vanity, Stone Counters
- Level: First
Bathroom 2
- Features: Exhaust Fan, Single Vanity, Tub With Shower
- Level: First
Dining room
- Features: Bar
- Level: First
- Area: 215.25 Square Feet
- Dimensions: 10.5x20.5
Family room
- Level: First
- Area: 290.25 Square Feet
- Dimensions: 13.5x21.5
Kitchen
- Features: Built-In Shelving, Kitchen Island, Pantry
- Level: First
Laundry
- Features: Built-In Shelving
- Level: First
Living room
- Level: First
- Area: 130 Square Feet
- Dimensions: 10x13
Office
- Level: First
- Area: 168 Square Feet
- Dimensions: 12x14
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Microwave, Range, Range Hood, Refrigerator, Washer
- Laundry: Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
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)
- Flooring: Brick/Stone, Carpet, Ceramic Tile
- Windows: Window Treatments
- Has fireplace: No
Interior area
- Total structure area: 3,679
- Total interior livable area: 2,850 sqft
Property
Parking
- Total spaces: 3
- Parking features: Driveway, Garage Door Opener
- Attached garage spaces: 3
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: Accessible Entrance
Features
- Levels: One
- Stories: 1
- Patio & porch: Front Porch, Patio, Rear Porch
- Exterior features: Irrigation System, Sidewalk
- Fencing: Fenced,Other
Lot
- Size: 0.32 Acres
- Features: Conservation Area, Sidewalk
- Residential vegetation: Mature Landscaping, Trees/Landscaped
Details
- Parcel number: 212227940100530
- Zoning: R-1A
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Florida
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 2005
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Cable Available, Electricity Available, Fire Hydrant, Natural Gas Available, Sprinkler Recycled, Street Lights
Community & HOA
Community
- Security: Fire Alarm
- Pet fee: $0 monthly
- Subdivision: WINTERS LNDG PH 01 A D F & G
HOA
- Has HOA: Yes
- HOA fee: $73 monthly
- HOA name: Southwest Property Management
- HOA phone: 407-656-1081
Location
- Region: Oakland
Financial & listing details
- Price per square foot: $298/sqft
- Tax assessed value: $546,470
- Annual tax amount: $3,979
- Date on market: 3/25/2026
- Cumulative days on market: 44 days
- Listing terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved, Asphalt
Price history
| Date | Event | Price |
|---|---|---|
| 5/27/2026 | Sold | $850,000-2.9%$298/sqft |
Source:  Stellar MLS #O6385221 Report a problem | ||
| 5/9/2026 | Pending sale | $875,000$307/sqft |
Source: Stellar MLS #O6385221 Report a problem | ||
| 5/4/2026 | Price change | $875,000-1.1%$307/sqft |
Source: Stellar MLS #O6385221 Report a problem | ||
| 3/25/2026 | Listed for sale | $885,000+270.3%$311/sqft |
Source: Stellar MLS #O6385221 Report a problem | ||
| 7/14/2010 | Sold | $239,000+4.4%$84/sqft |
Source: Public Record Report a problem | ||
| 1/17/2010 | Listing removed | $229,000$80/sqft |
Source: Watson Realty Corp #MO4929574 Report a problem | ||
| 8/20/2009 | Listed for sale | $229,000-33%$80/sqft |
Source: Watson Realty Corp #MO4929574 Report a problem | ||
| 1/12/2006 | Sold | $341,600$120/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $3,979 +6.1% | $260,293 +3% |
| 2023 | $3,751 +3.2% | $252,712 +3% |
| 2022 | $3,633 +1.3% | $245,351 +3% |
| 2021 | $3,587 +0.4% | $238,205 +1.4% |
| 2020 | $3,573 +1.2% | $234,916 +2.3% |
| 2019 | $3,530 +0.4% | $229,634 +1.9% |
| 2018 | $3,517 | $225,352 -21.4% |
| 2017 | $3,517 +1% | $286,869 +10.3% |
| 2016 | $3,482 +0.6% | $259,992 +3.6% |
| 2015 | $3,462 -1.9% | $250,843 +5.2% |
| 2014 | $3,528 +2.4% | $238,377 +13.6% |
| 2013 | $3,445 -2.3% | $209,823 -1.4% |
| 2012 | $3,527 -2.9% | $212,728 -2.1% |
| 2011 | $3,632 -20.7% | $217,287 -5.7% |
| 2010 | $4,580 | $230,488 -6.1% |
| 2009 | -- | $245,439 -20.7% |
| 2008 | $5,664 +5.9% | $309,503 -7.5% |
| 2007 | $5,349 -7.6% | $334,728 -2.7% |
| 2006 | $5,792 +3762.4% | $344,092 +4201.1% |
| 2005 | $150 | $8,000 |
Find assessor info on the county website
Neighborhood: 34787
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Nearby schools
GreatSchools rating
- 9/10Tildenville Elementary SchoolGrades: PK-5Distance: 0.8 mi
- 4/10Lakeview Middle SchoolGrades: 6-9Distance: 1.2 mi
- 7/10West Orange High SchoolGrades: 9-12Distance: 3.2 mi
Schools provided by the listing agent
- Elementary: Tildenville Elem
- Middle: Lakeview Middle
- High: West Orange High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$850,000
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Estimated market value
$850,000
- Florida
- Orange County
- Winter Garden
- 34787
- 8 Winters Landing Dr
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