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Back 21 Kentucky Street
Off Market

21 Kentucky Street

Winchester KY 40391

3
2
1340 sq. ft.
7405.2 sq. ft.
Single-Family
Last sold for $219,900
Jenny MateyokeJenny Mateyoke, last sold this property on 28 May 2026 after 50 days on market.

Overview

Updated, move-in ready, and right in the heart of Winchester. This is the kind of home that checks boxes and feels good the second you walk in. Start your mornings or wind down in the evenings on the inviting covered front porch—it's the kind of space that makes you want to slow down for a minute. Inside, everything has been updated so you can skip the projects and just enjoy your home from day one. The kitchen is a standout, with a large island that naturally becomes the gathering spot. It opens right into the great room, creating an easy, connected flow that works whether you're hosting or just going about your day. You'll find 3 bedrooms and 2 beautifully updated bathrooms that feel fresh and thoughtfully done. And if you're over carpet, you'll love that this home is completely carpet-free—clean, low-maintenance, and modern. Out back, there's a large yard with plenty of room to spread out, a deck for relaxing or entertaining, and a storage building to keep everything organized.

Features

3 bedrooms
2 bathrooms
1340 sq. ft. floor area
7405.2 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Winchester over the last 12 months, the estimated median property value of 21 Kentucky Street is $258.2k.

Median value
$258.2k
Estimated value range
$80k - $880k
Median days on market
17
Estimated value trend
8%
increase over the last 12 months
Average days on market is based on recent, comparable sales in Winchester. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 21 Kentucky Street

2026
Sold
$219,900
28 May 2026 by Jenny Mateyoke, of Keller Williams Legacy Group
2024
Sold
$189,500
30 Jan 2024 by Tony Giglio, of ListWithFreedom.com
2022
Sold
$22,000
09 Sep 2022 by Greg Wood, of Freedom Realty & Property Management

Happy sellers in Winchester

81%
81% of sellers in Winchester reported that their sale price either exceeded or met their price expectations.

Winchester stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 20 reviews in Winchester over the last 12 months.

Local market activity for 3 bedroom single-family properties in Winchester

In the last 12 months, 228 three-bedroom single-family properties similar to 21 Kentucky Street, have been sold.

This represents a 12% increase in three-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Winchester

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Melissa Brown

Sellers who recommend Melissa Brown have praised them for being responsive, local expert, clear communication, supportive, friendly, dedicated, and detail-oriented

  •   5   (154 reviews)
  •  6 Reviews in Winchester
  •  8 Sales in Winchester
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Whitney Ensor

Sellers who recommend Whitney Ensor have praised them for being local expert, clear communication, supportive, friendly, reliable, responsive, and attentive

  •   5   (43 reviews)
  •  3 Reviews in Winchester
  •  4 Sales in Winchester
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Terry Powell

Terry Powell is a recommended agent for Winchester.  They have 4 local sales and collected 3 local reviews across the last 12 months.

  •   5   (80 reviews)
  •  3 Reviews in Winchester
  •  4 Sales in Winchester
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Jessica Noto

Sellers who recommend Jessica Noto have praised them for being local expert, dedicated, responsive, clear communication, friendly, stress-free process, and trustworthy

  •   5   (45 reviews)
  •  3 Reviews in Winchester
  •  2 Sales in Winchester
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