Winchester, KY Real Estate & Homes For Sale
229 homes
Use arrow keys to navigateNEW - 3 HRS AGOTom Goebel & Company, Imagine MLS
Use arrow keys to navigateNEW - 20 HRS AGO
3D VIEW136.8 ACRESBluegrass Sotheby's International Realty, Imagine MLS
Use arrow keys to navigateNEWOPEN SAT, 1-3PM0.62 ACRESThreshold Real Estate Services, Imagine MLS
Use arrow keys to navigateNEWOPEN SUN, 1-3PM3D VIEWRE/MAX Elite Lexington, Imagine MLS
Use arrow keys to navigateNEW - 2 DAYS AGOWoods Realty Group, Imagine MLS
Use arrow keys to navigate59.1 ACRESThe Agency, Imagine MLS
Use arrow keys to navigateFreedom Realty & Property Management, Imagine MLS
3.35 ACRESRector Hayden Realtors, Imagine MLS
3D VIEWRE/MAX Creative, Winchester, Imagine MLS
0.25 ACRESRector Hayden Realtors, Imagine MLS
Freedom Realty & Property Management, Imagine MLS
14.86 ACRESWEICHERT REALTORS - ABG Properties, Imagine MLS
FOR SALE BY OWNER3 ACRES
NEW CONSTRUCTIONBUILDABLE PLAN
FOR SALE BY OWNER
0.44 ACRESDream Maker Realty, LLC, Imagine MLS
3D VIEW4.14 ACRESKeller Williams Legacy Group, Imagine MLS
0.26 ACRESFreedom Realty & Property Management, Imagine MLS
0.29 ACRESDream Maker Realty, LLC, Imagine MLS
3D VIEWRE/MAX Creative, Winchester, Imagine MLS
5 ACRESWever Realty LLC, Imagine MLS
0.25 ACRESDream Maker Realty, LLC, Imagine MLS
0.28 ACRESBerkshire Hathaway HomeServices Foster Realtors, Imagine MLS
0.34 ACRESRE/MAX Elite Lexington, Imagine MLS
NEW CONSTRUCTIONBUILDABLE PLAN
0.5 ACRESeXp Realty, LLC, Imagine MLS
NEW CONSTRUCTIONBUILDABLE PLAN
1.2 ACRESMurphy Realty Group, Imagine MLS
2.45 ACRESColdwell Banker McMahan, Imagine MLS
0.3 ACRESKentucky Residential Real Estate, LLC, Imagine MLS
3D VIEWRE/MAX Creative, Winchester, Imagine MLS
Coldwell Banker McMahan, Imagine MLS
0.27 ACRESFreedom Realty & Property Management, Imagine MLS
NEW CONSTRUCTIONBUILDABLE PLAN
0.41 ACRESColdwell Banker McMahan, Imagine MLS
0.4 ACRESThe Brokerage, 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 $253,754
| Month | Median home value |
|---|---|
| September 2025 | $242k |
| October 2025 | $243k |
| November 2025 | $245k |
| December 2025 | $246k |
| January 2026 | $247k |
| February 2026 | $248k |
| March 2026 | $250k |
| April 2026 | $251k |
| May 2026 | $251k |
| June 2026 | $252k |
| July 2026 | $253k |
| August 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 9 new listings in Winchester, KY and 229 homes for sale.
| Home Size | Home Value* |
|---|---|
| 2 bedrooms (24 homes) | $165,659 |
| 3 bedrooms (77 homes) | $259,286 |
| 4 bedrooms (31 homes) | $339,835 |
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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