Winchester, KY Real Estate & Homes For Sale
228 homes
Use arrow keys to navigateNEW - 4 HRS AGO7.31 ACRESHomeFirst Real Estate, Imagine MLS
Use arrow keys to navigateNEW - 11 HRS AGOHomeFirst Real Estate, Imagine MLS
Use arrow keys to navigateNEW - 13 HRS AGOCaperton Realty
Use arrow keys to navigateNEW - 1 DAY AGO0.37 ACRESColdwell Banker McMahan, Imagine MLS
Use arrow keys to navigateNEW - 1 DAY AGOUnited Real Estate Bluegrass, Imagine MLS
Use arrow keys to navigateNEW - 2 DAYS AGOeXp Realty LLC, Imagine MLS
Use arrow keys to navigateNEW - 2 DAYS AGO0.46 ACRESDream Maker Realty, LLC, Imagine MLS
NEW - 2 DAYS AGO0.41 ACRESThe Agency, Imagine MLS
NEW - 2 DAYS AGOFreedom Realty & Property Management, Imagine MLS
NEW - 2 DAYS AGOFreedom Realty & Property Management, Imagine MLS
Ensor Real Estate, LLC, Imagine MLS
RE/MAX Creative, Winchester, Imagine MLS
2.5 ACRESThe Agency, Imagine MLS
NEW CONSTRUCTIONBUILDABLE PLAN
NEW CONSTRUCTIONBUILDABLE PLAN
Keller Williams Commonwealth, Imagine MLS
OPEN SAT, 12-2PMEnsor Real Estate, LLC, Imagine MLS
0.25 ACRESeXp Realty, LLC, Imagine MLS
Freedom Realty & Property Management, Imagine MLS
WEICHERT REALTORS - ABG Properties, Imagine MLS
Stewart & Co Realty LLC, Imagine MLS
OPEN SAT, 1-3PMJoyce Marcum Realty, Imagine MLS
0.67 ACRESColdwell Banker McMahan, Imagine MLS
NEW CONSTRUCTIONBUILDABLE PLAN
3.05 ACRESRed River Gorge Real Estate, Imagine MLS
5 ACRESWTC Realty LLC, Imagine MLS
FOR SALE BY OWNER0.4 ACRES
FOR SALE BY OWNER
NEW CONSTRUCTIONBUILDABLE PLAN
14.38 ACRESRE/MAX Creative, Winchester, Imagine MLS
0.47 ACRESThe Agency, Imagine MLS
Coldwell Banker McMahan, Imagine MLS
3D VIEWUnited Real Estate Bluegrass, Imagine MLS
Kentucky Residential Real Estate, LLC, Imagine MLS
Winchester, KY Real Estate Trends
Learn about the Winchester, KY housing market through trends and averages.Affordability of Living in Winchester, KY
The median home value is $254,489
| Month | Median home value |
|---|---|
| June 2025 | $244k |
| July 2025 | $244k |
| August 2025 | $244k |
| September 2025 | $245k |
| October 2025 | $246k |
| November 2025 | $248k |
| December 2025 | $249k |
| January 2026 | $250k |
| February 2026 | $251k |
| March 2026 | $252k |
| April 2026 | $254k |
| May 2026 | $254k |
Trends and affordability stats are provided by third party data sources.
Average Home Value in Winchester, KY, by Home Size
Currently, there are 18 new listings in Winchester, KY and 228 homes for sale.
| Home Size | Home Value* |
|---|---|
| 2 bedrooms (15 homes) | $167,667 |
| 3 bedrooms (87 homes) | $259,672 |
| 4 bedrooms (30 homes) | $340,064 |
What Locals Say about Winchester
Review Highlights
Winchester, KY: steady living with solid schools, low crime, and long-term value. People like safe, clean, close‑knit blocks, good schools, parks, and lively local festivals. They dislike a shady downtown feel, coyotes, occasional loose dogs, and rush-hour traffic.
AI-generated summary of moderated reviews.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Metro Search, Inc. Real estate listings held by brokerage firms other than Zillow, Inc. are marked with the Internet Data Exchange logo or the Internet Data Exchange thumbnail logo and detailed information about each listing includes the name of the listing broker.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but not guaranteed.
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