Pending
Sale Pending at 1056 Winding Oak Trl, Lexington, KY 40511 | MLS# 26021752 | Listing updated on 2026-09-02
Photo 1 of Sale Pending at 1056 Winding Oak Trl, Lexington, KY 40511 | MLS# 26021752 | Listing updated on 2026-09-02
Photo 2 of Sale Pending at 1056 Winding Oak Trl, Lexington, KY 40511 | MLS# 26021752 | Listing updated on 2026-09-02
Photo 3 of Sale Pending at 1056 Winding Oak Trl, Lexington, KY 40511 | MLS# 26021752 | Listing updated on 2026-09-02
Photo 4 of Sale Pending at 1056 Winding Oak Trl, Lexington, KY 40511 | MLS# 26021752 | Listing updated on 2026-09-02
25+
Beds Icon

Street View

$299,000

Monthly Est:$1,488

  • Beds Icon3 Beds
  • Beds Icon
    2 Baths
  • Beds Icon1,116sqft

1056 Winding Oak Trl, Lexington, KY 40511

$1,488/moEst:

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  • Single Family Residence

  • Built in 2005

  • $10/mo HOA

  • 0.12 acre lot

  • $268/sq.ft

Description

There's a lot to love inside this home, but the backyard may steal the show. Backing to the equestrian section of Masterson Station Park, this home offers an uncommon sense of openness and privacy, along with beautiful sunset views and direct backyard access to a park walking trail. An expanded patio gives you even more space to take advantage of the setting. Inside, the updates go well beyond the obvious. Herringbone-pattern LVP flooring runs throughout the home, and thoughtful improvements have been carried from room to room—from updated lighting and plumbing fixtures to coordinated interior hardware, including door handles and hinges. Even the toilets have been replaced. The result is a home that feels fresh, cohesive and exceptionally well finished. The upgraded kitchen features a quartz-topped island, black farmhouse sink with touch faucet, soft-close cabinetry and convenient pull-out drawers. All LG kitchen appliances were replaced in 2024, and the all-in-one washer/dryer conveys. The location also puts shopping, dining and everyday conveniences along the Leestown Road corridor within easy reach. Updated from the finishes you immediately notice to the small details you normally don't, this is a home where much of the work has already been done. And with Masterson Station Park just beyond the backyard, the setting may be the upgrade you appreciate most.

  • Houzeo last checked: 12 hours ago
  • Listing updated: September 2, 2026 at 10:01 am
  • Listing Provided by: Laura Broyles (859) 230-9542 , Lisa L Peel | United Real Estate Bluegrass (859) 800-7355
  • Source: Lexington Bluegrass AOR (Imagine) MLS-KY | MLS#: 26021752 Lexington Bluegrass AOR (Imagine) MLS-KY

Property Details

  • Status

    Pending

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Fayette County

  • City

    Lexington

  • Neighborhood

    --

  • Year Built

    2005

  • HOA Fees

    $10/mo

  • Finished Area

    1,116 sqft

  • Lot Size

    0.12 acre lot

  • Basement Area

    - sqft

  • MLS Name

    Lexington Bluegrass AOR (Imagine) MLS

  • MLS Number

    26021752

  • MLS Status

    Pending

  • Days on Market

    50

  • Cumulative Days on Market

    11

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Location

HOA Management

N/A

HOA Fees

$120/ Annually

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Other Other

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 2

Interior

  • Window Features

    Blinds

  • Interior Features

    Breakfast Bar, Ceiling Fan(s), Eat In Kitchen, Entrance Foyer, Primary Downstairs, Walk In Closet(s)

  • Appliances

    Dishwasher, Disposal, Dryer, Microwave, Oven, Range, Refrigerator, Washer

  • Sewer

    Public Sewer

  • Heating

    Electric

  • Cooling

    Electric

Construction

  • Year Built

    Year Built: 2005

  • Home type

    Single Family Residence

  • Architectural Style

    Ranch

  • Foundation Details

    Slab

  • Construction Materials

    Vinyl Siding, Brick Veneer

  • Roof

    Shingle

Utilities & Energy

  • Laundry Features

    Electric Dryer Hookup, Main Level, Washer Hookup

  • Parking Features

    Attached Garage, Driveway, Garage Faces Front, Off Street

  • Water Source

    Public

Other Features

  • Subdivision Name

    Masterson Station

  • Community Features

    Park, Pool

  • Patio And Porch Features

    Patio, Rear Patio

Price History

DateEventPrice

09/02/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26021752

Pending

$299,000

$268/sqft

08/21/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26021752

Listed for Sale

$299,000 +12.83%

$268/sqft

05/09/2024

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #24005416

Price Increased

$265,000 +60.90%

$237/sqft

07/24/2018

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #1812956

Price Increased

$164,697 +45.11%

$148/sqft

03/01/2016

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #1600727

Sold

$113,500

$102/sqft

Getting Around 1056 Winding Oak Trl

Bike Score®

Bike Score

Somewhat Bikeable

22/100

Walk Score®

Walk Score

Car-Dependent

2/100

Transit Score®

Transit Score

Minimal Transit

22/100

Data provided by Redfin

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Based on information from the IMAGINE MLS® through Oct 09, 2026, 02:30PM. Copyrighted by the Imagine MLS®. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data on this website is deemed reliable but is not guaranteed accurate by the MLS. © 2026 IMAGINE MLS®. All Rights Reserved.

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