Welcome home to 1028 Winding Oak Trail — a beautifully maintained 3-bedroom, 2-bath ranch perfectly situated backing up to the scenic green space of Masterson Station Park! Built in 2006, this home features an open layout with vaulted ceilings and bright windows that fills the living area with natural light. The kitchen offers ample counter space and cabinetry, flowing easily into the dining and living areas — ideal for entertaining or relaxing nights in. The primary suite includes a walk-in closet and private bath, while two additional bedrooms share a full hall bath. Enjoy your morning coffee or evening sunsets from the patio overlooking open fields and even views of nearby horses! Additional highlights include a one-car garage, fully fenced backyard, and convenient access to schools, parks, and walking trails. With one-level living and a quiet setting just minutes from downtown Lexington, this home offers the perfect blend of comfort, convenience, and outdoor beauty. Property has a new roof for buyer!
Sold for $270,000
$270,000
1028 Winding Oak Trl, Lexington, KY 40511
3beds
1,222sqft
Single Family Residence
Built in 2005
4,800 Square Feet Lot
$273,600 Zestimate®
$221/sqft
$1,802 Estimated rent
Home value
$273,600
$260,000 - $290,000
$1,802/mo
Zestimate® history
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List your homeWhat's special
Patio overlooking open fieldsViews of nearby horsesOpen layoutVaulted ceilingsBright windowsNatural lightAmple counter space
Zillow last checked:
Listing updated:
Listed by:
Elizabeth Hodge 859-333-9933,
Lifstyl Real Estate
Bought with:
Anne Livengood, 295037
The Brokerage
Source: Imagine MLS,MLS#: 25504968
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Level: First
Kitchen
- Level: First
Living room
- Level: First
Heating
- Electric, Heat Pump
Cooling
- Central Air, Ceiling Fan(s), Electric, Heat Pump
Appliances
- Included: Disposal, Dishwasher, Microwave, Refrigerator, Oven
- Laundry: Electric Dryer Hookup, Washer Hookup
Features
- Eat-in Kitchen, Walk-In Closet(s), Ceiling Fan(s)
- Flooring: Carpet, Laminate
- Doors: Storm Door(s)
- Windows: Insulated Windows, Blinds
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 1,222
- Total interior livable area: 1,222 sqft
- Finished area above ground: 1,222
- Finished area below ground: 0
Property
Parking
- Total spaces: 1
- Parking features: Attached Garage, Driveway, Garage Door Opener, Off Street, Garage Faces Front
- Garage spaces: 1
- Has uncovered spaces: Yes
Features
- Levels: One
- Fencing: Privacy
- Has view: Yes
- View description: Neighborhood
Lot
- Size: 4,800 Square Feet
Details
- Additional structures: Shed(s)
- Parcel number: 38129050
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch
- Property subtype: Single Family Residence
Materials
- Brick Veneer, Vinyl Siding
- Foundation: Slab
- Roof: Composition
Condition
- New construction: No
- Year built: 2005
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Available, Electricity Connected, Sewer Connected, Water Connected
Community & HOA
Community
- Features: Park
- Subdivision: Masterson Station
HOA
- Has HOA: Yes
- Amenities included: None
- Services included: Maintenance Grounds
- HOA fee: $120 annually
Location
- Region: Lexington
Financial & listing details
- Price per square foot: $221/sqft
- Tax assessed value: $169,100
- Annual tax amount: $2,091
- Date on market: 10/30/2025
Price history
| Date | Event | Price |
|---|---|---|
| 3/13/2026 | Sold | $270,000-1.8%$221/sqft |
Source:  Imagine MLS #25504968 Report a problem | ||
| 2/12/2026 | Contingent | $275,000$225/sqft |
Source: Imagine MLS #25504968 Report a problem | ||
| 1/25/2026 | Price change | $275,000-1.1%$225/sqft |
Source: Imagine MLS #25504968 Report a problem | ||
| 12/31/2025 | Price change | $278,000-0.7%$227/sqft |
Source: Imagine MLS #25504968 Report a problem | ||
| 11/28/2025 | Price change | $280,000-1.8%$229/sqft |
Source: Imagine MLS #25504968 Report a problem | ||
| 10/30/2025 | Listed for sale | $285,000+104.3%$233/sqft |
Source: Imagine MLS #25504968 Report a problem | ||
| 9/25/2017 | Sold | $139,500$114/sqft |
Source: Imagine MLS #1718676 Report a problem | ||
| 8/17/2017 | Pending sale | $139,500$114/sqft |
Source: United Real Estate Lexington #1718676 Report a problem | ||
| 8/14/2017 | Listed for sale | $139,500+17.2%$114/sqft |
Source: United Real Estate Lexington #1718676 Report a problem | ||
| 6/14/2005 | Sold | $119,000$97/sqft |
Source:  Imagine MLS #415585 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $2,091 | $169,100 |
| 2023 | $2,091 -3.2% | $169,100 |
| 2022 | $2,160 | $169,100 |
| 2021 | $2,160 +21.2% | $169,100 +21.2% |
| 2020 | $1,782 | $139,500 |
| 2019 | $1,782 | $139,500 |
| 2018 | $1,782 +15% | $139,500 +9.6% |
| 2017 | $1,550 +16.4% | $127,300 +7% |
| 2015 | $1,332 | $119,000 |
| 2014 | $1,332 | $119,000 |
| 2012 | $1,332 | $119,000 |
| 2011 | -- | -- |
| 2010 | -- | -- |
| 2009 | -- | -- |
| 2008 | -- | $119,000 |
| 2006 | -- | -- |
| 2005 | -- | -- |
| 2004 | -- | -- |
Find assessor info on the county website
Neighborhood: Masterson
Nearby homes
- $278,9002 bd2 ba1.2k sqft1024 Winding Oak Trl, Lexington, KY 40511Off Market
- $318,1003 bd3 ba1.4k sqft1032 Winding Oak Trl, Lexington, KY 40511Off Market
- $322,8003 bd3 ba1.5k sqft1020 Winding Oak Trl, Lexington, KY 40511Off Market
- $301,3003 bd2 ba1.2k sqft1036 Winding Oak Trl, Lexington, KY 40511Off Market
- $261,5993 bd2 ba1.2k sqft1016 Winding Oak Trl, Lexington, KY 40511Sold
- $329,2003 bd3 ba1.6k sqft1040 Winding Oak Trl, Lexington, KY 40511Off Market
- $319,3003 bd2 ba1.6k sqft3092 River Run Trl, Lexington, KY 40511Off Market
- $343,8004 bd3 ba1.6k sqft1012 Winding Oak Trl, Lexington, KY 40511Off Market
Nearby schools
GreatSchools rating
- 8/10Sandersville Elementary SchoolGrades: PK-5Distance: 0.5 mi
- 6/10Leestown Middle SchoolGrades: 6-8Distance: 2.6 mi
- 3/10Bryan Station High SchoolGrades: 9-12Distance: 5.5 mi
Schools provided by the listing agent
- Elementary: Sandersville
- Middle: Leestown
- High: Bryan Station
Source: Imagine 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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- Kentucky
- Fayette County
- Lexington
- 40511
- Masterson
- 1028 Winding Oak Trl
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