Contingent

Price cut: $14K (10/3)

$275,000

996 Winding Oak Trl, Lexington, KY 40511

3beds

1,210sqft

$1,897/mo

Get pre-qualified

Single Family Residence

Built in 2005

4,791 Square Feet Lot

$271,100 Zestimate^®

$227/sqft

$10/mo HOA

What's special

Recently upgraded flooringFresh paintOpen floor planGreat lighting

Charming 3 bedroom, 2 bath home with fresh paint, recently upgraded flooring and open floor plan and great lighting. A clean canvas awaits your personal touch. Well maintained and cared for you can easily move right in and be settled for the holidays.

33 days
882
82

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 2
Full bathrooms: 2

Primary bedroom

Level: First

Bedroom 2

Level: First

Bedroom 3

Description: Could also be used as office
Level: First

Primary bathroom

Level: First

Bathroom 2

Level: First

Foyer

Level: First

Great room

Level: First

Kitchen

Level: First

Utility room

Level: First

Heating

Electric, Heat Pump

Cooling

Central Air, Electric

Appliances

Included: Disposal, Dishwasher, Refrigerator, Range
Laundry: Electric Dryer Hookup, Washer Hookup

Features

Entrance Foyer, Eat-in Kitchen, Ceiling Fan(s)
Windows: Screens
Has basement: No
Has fireplace: No

Interior area

Total structure area: 1,210
Total interior livable area: 1,210 sqft
Finished area above ground: 1,210
Finished area below ground: 0

Property

Parking

Total spaces: 1
Parking features: Attached Garage, Garage Door Opener, Off Street
Garage spaces: 1
Has uncovered spaces: Yes

Features

Levels: One
Fencing: Partial

Lot

Size: 4,791 Square Feet
Features: Many Trees

Details

Parcel number: 38128970

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: 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: Pool
Services included: Other, Maintenance Grounds
HOA fee: $120 annually

Location

Region: Lexington

Financial & listing details

Price per square foot: $227/sqft
Tax assessed value: $150,600
Annual tax amount: $1,862
Date on market: 9/15/2026

Estimated market value

$271,100

$258,000 - $285,000

$1,821/mo

Price history

Date	Event	Price
10/11/2026	Contingent	$275,000$227/sqft
Source: Imagine MLS #26025347 Report a problem
10/3/2026	Price change	$275,000-4.8%$227/sqft
Source: Imagine MLS #26025347 Report a problem
9/15/2026	Listed for sale	$289,000+156.9%$239/sqft
Source: Imagine MLS #26025347 Report a problem
2/4/2021	Sold	$112,500$93/sqft
Source: Public Record Report a problem
3/18/2016	Sold	$112,500-6.2%$93/sqft
Source: Imagine MLS #1600683 Report a problem
2/19/2016	Pending sale	$119,900$99/sqft
Source: Guide Realty, Inc. #1600683 Report a problem
1/13/2016	Listed for sale	$119,900+3.7%$99/sqft
Source: Guide Realty, Inc. #1600683 Report a problem
9/8/2005	Sold	$115,669$96/sqft
Source: Agent Provided Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$1,862	$150,600
2024	$1,862	$150,600
2023	$1,862 -3.2%	$150,600
2022	$1,924	$150,600
2021	$1,924 +33.9%	$150,600 +33.9%
2020	$1,437	$112,500
2019	$1,437	$112,500
2018	$1,437 +4.9%	$112,500
2017	$1,370 +5.8%	$112,500 -2.8%
2015	$1,295	$115,700
2014	$1,295	$115,700
2012	$1,295	$115,700
2011	--	--
2010	--	--
2009	--	--
2008	--	$115,700
2006	--	--
2005	--	--
2004	--	--