For sale

Price cut: $11.5K (7/1)

$297,500

944 Winding Oak Trl, Lexington, KY 40511

3beds

1,222sqft

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Single Family Residence

Built in 2007

5,662 Square Feet Lot

$292,900 Zestimate^®

$243/sqft

$10/mo HOA

What's special

Partially fenced yardCharming ranch-style homeSingle-level layoutWell-proportioned bedroomsPractical storage throughout

Welcome to 944 Winding Oak Trail, a charming ranch-style home in the heart of Masterson Station, offering comfort, simplicity, and easy everyday living. The single-level layout provides an effortless flow for relaxing or gathering, paired with well-proportioned bedrooms and practical storage throughout. Outside, the partially fenced yard creates a potential private space for pets, play, or unwinding at the end of the day. With quick access to Masterson Station Park, neighborhood trails, and the conveniences of Citation and Georgetown Road, this home delivers a balanced lifestyle in one of Lexington's most accessible corridors.

26 days

1,274

56

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Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 2
Full bathrooms: 2

Primary bedroom

Level: First

Bedroom 2

Level: First

Bedroom 3

Level: First

Kitchen

Level: First

Living room

Level: First

Heating

Electric, Heat Pump

Cooling

Central Air, Electric, Heat Pump

Appliances

Included: Dishwasher, Microwave, Refrigerator, Range
Laundry: Electric Dryer Hookup, Main Level, Washer Hookup, Common Area

Features

Eat-in Kitchen
Flooring: Carpet, Vinyl
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
Garage spaces: 1
Has uncovered spaces: Yes

Features

Levels: One
Fencing: Partial,Wood
Has view: Yes
View description: Neighborhood

Lot

Size: 5,662 Square Feet

Details

Parcel number: 38129950

Construction

Type & style

Home type: SingleFamily
Architectural style: Ranch
Property subtype: Single Family Residence

Materials

Brick Veneer, Vinyl Siding
Foundation: Slab
Roof: Shingle

Condition

Year built: 2007

Utilities & green energy

Sewer: Public Sewer
Water: Public
Utilities for property: Electricity Connected, Sewer Connected, Water Connected

Community & HOA

Community

Features: Park
Security: Security System Owned
Subdivision: Masterson Station

HOA

Has HOA: Yes
Amenities included: None
Services included: Other
HOA fee: $120 annually

Location

Region: Lexington

Financial & listing details

Price per square foot: $243/sqft
Tax assessed value: $162,500
Annual tax amount: $2,009
Date on market: 6/24/2026

Estimated market value

$292,900

$278,000 - $308,000

$1,783/mo

Price history

Date	Event	Price
7/1/2026	Price change	$297,500-3.7%$243/sqft
Source: Imagine MLS #26014728 Report a problem
6/24/2026	Listed for sale	$309,000+106%$253/sqft
Source: Imagine MLS #26014728 Report a problem
3/5/2019	Sold	$150,000-3.2%$123/sqft
Source: Imagine MLS #1825318 Report a problem
1/23/2019	Pending sale	$154,900$127/sqft
Source: RE/MAX Creative Realty #1825318 Report a problem
10/10/2018	Price change	$154,900-1.3%$127/sqft
Source: RE/MAX Creative Realty #1825318 Report a problem
9/18/2018	Listed for sale	$157,000+36.5%$128/sqft
Source: RE/MAX Creative Realty #1820969 Report a problem
11/30/2007	Sold	$115,000$94/sqft
Source: Imagine MLS #724256 Report a problem

Public tax history

Year	Property taxes	Tax assessment
2024	$2,009	$162,500
2023	$2,009 -3.2%	$162,500
2022	$2,076 0%	$162,500
2021	$2,076 +8.3%	$162,500 +8.3%
2020	$1,916 +17.2%	$150,000 +17.2%
2019	$1,635	$128,000
2018	$1,635 +4.9%	$128,000
2017	$1,558 +21.1%	$128,000 +11.3%
2015	$1,287	$115,000
2014	$1,287	$115,000
2012	$1,287	$115,000
2011	--	--
2010	--	--
2009	--	--
2008	--	$115,000
2006	--	--
2005	--	--
2004	--	--

Find assessor info on the county website

Monthly payment

Est. payment

Payment breakdown

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Principal & interest
$1,547
Mortgage insurance
$0
Property taxes
$170
Home insurance
$105
HOA fees
$0
Utilities
Not included

All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.

HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.

Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.

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