Winchester, KY Real Estate & Homes For Sale
222 homes
Use arrow keys to navigateNEW - 36 MIN AGO0.9 ACRESThe Agency, Imagine MLS
Use arrow keys to navigateNEW - 2 HRS AGOStewart & Co Realty LLC, Imagine MLS
Use arrow keys to navigateNEW - 3 HRS AGOJoyce Marcum Realty, Imagine MLS
Use arrow keys to navigateNEW - 18 HRS AGO2.53 ACRESColdwell Banker McMahan, Imagine MLS
Use arrow keys to navigateNEW - 21 HRS AGO0.67 ACRESColdwell Banker McMahan, Imagine MLS
Use arrow keys to navigateNEW CONSTRUCTIONBUILDABLE PLAN
Use arrow keys to navigateNEW - 1 DAY AGO3.05 ACRESRed River Gorge Real Estate, Imagine MLS
NEW - 1 DAY AGO5 ACRESWTC Realty LLC, Imagine MLS
NEW - 2 DAYS AGOFOR SALE BY OWNER0.4 ACRES
NEW - 2 DAYS AGOFOR 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
Keller Williams Legacy Group, Imagine MLS
Green Team Real Estate Service, Imagine MLS
OPEN SUN, 12-4PMFOR SALE BY OWNER
0.52 ACRESBluegrass Home Group, Imagine MLS
2.5 ACRESRE/MAX Creative Realty, Imagine MLS
HomeLand Real Estate Inc - Mt Sterling, Imagine MLS
NEW CONSTRUCTIONBUILDABLE PLAN
Keller Williams Bluegrass Realty, Imagine MLS
FOR SALE BY OWNER
FOR SALE BY OWNER
13.74 ACRESFreedom Realty & Property Management, Imagine MLS
0.26 ACRESFreedom Realty & Property Management, Imagine MLS
Stewart & Co Realty LLC, Imagine MLS
Keller Williams Legacy Group, Imagine MLS
3D VIEW7.4 ACRESRE/MAX Elite Lexington, Imagine MLS
Coldwell Banker McMahan, Imagine MLS
Keller Williams Bluegrass Realty, Imagine MLS
59.1 ACRESThe Agency, Imagine MLS
11.3 ACRESSteven D Adams Real Estate Services, LLC, Imagine MLS
2.59 ACRESRO&CO Real Estate, Imagine MLS
32.87 ACRESColdwell Banker McMahan, Imagine MLS
3D VIEW0.25 ACRESRE/MAX Creative, Winchester, 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 $250,931
| Month | Median home value |
|---|---|
| May 2025 | $241k |
| June 2025 | $241k |
| July 2025 | $241k |
| August 2025 | $241k |
| September 2025 | $242k |
| October 2025 | $244k |
| November 2025 | $245k |
| December 2025 | $246k |
| January 2026 | $247k |
| February 2026 | $248k |
| March 2026 | $250k |
| April 2026 | $251k |
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 222 homes for sale.
| Home Size | Home Value* |
|---|---|
| 2 bedrooms (16 homes) | $165,387 |
| 3 bedrooms (79 homes) | $257,240 |
| 4 bedrooms (27 homes) | $336,654 |
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.
