Winchester, KY Real Estate & Homes For Sale
212 homes
Use arrow keys to navigateNEW - 56 MIN AGO2.59 ACRESRO&CO Real Estate, Imagine MLS
Use arrow keys to navigateNEW - 1 HR AGOUnited Country Re/Cntry Living Spec Inc
Use arrow keys to navigateNEW - 2 HRS AGO32.87 ACRESColdwell Banker McMahan, Imagine MLS
Use arrow keys to navigateNEW - 2 HRS AGOBridgewater Real Estate, Imagine MLS
Use arrow keys to navigateNEW - 16 HRS AGO
3D VIEW0.25 ACRESRE/MAX Creative, Winchester, Imagine MLS
Use arrow keys to navigateNEW - 17 HRS AGO3D VIEWRE/MAX Creative, Winchester, Imagine MLS
Use arrow keys to navigateNEW - 18 HRS AGOMELIA Realty LLC, Imagine MLS
NEW - 18 HRS AGO274.52 ACRESMELIA Realty LLC, Imagine MLS- NEW - 18 HRS AGO3.93 ACRESMELIA Realty LLC, Imagine MLS
NEW - 21 HRS AGOColdwell Banker McMahan, Imagine MLS
NEW - 1 DAY AGO2.18 ACRESKeller Williams Commonwealth, Imagine MLS
OPEN SUN, 1-3PM0.37 ACRESThe Brokerage, Imagine MLS
10.02 ACRESDream Maker Realty, LLC, Imagine MLS
Lois Ann Disponett Real Est, Imagine MLS
RE/MAX Creative, Winchester, Imagine MLS
8.03 ACRESExit Realty Crutcher Frankfort, Imagine MLS
0.36 ACRESKentucky Land and Home, Imagine MLS
Freedom Realty & Property Management, Imagine MLS
FOR SALE BY OWNER0.37 ACRES
5.05 ACRESKeller Williams Commonwealth, Imagine MLS
5.05 ACRESKeller Williams Commonwealth, Imagine MLS
3D VIEW0.31 ACRESRE/MAX Elite Lexington, Imagine MLS
Kentucky Residential Real Estate, LLC, Imagine MLS
0.66 ACRESTom Goebel & Company, Imagine MLS
0.34 ACRESKeller Williams Commonwealth, Imagine MLS
60.65 ACRESBluegrass Property Exchange, Imagine MLS
0.47 ACRESMarshall Lane Real Estate - Lexington, Imagine MLS
1.43 ACRESBerkshire Hathaway HomeServices Foster Realtors, Imagine MLS
OPEN SUN, 2-4PMKeller Williams Bluegrass Realty, Imagine MLS
0.33 ACRESMcCallie Real Estate, Imagine MLS
0.26 ACRESFreedom Realty & Property Management, Imagine MLS
FOR SALE BY OWNER0.72 ACRES
FOR SALE BY OWNER
RE/MAX Creative Realty, Imagine MLS
Keller Williams Commonwealth, Imagine MLS
HomeLand Real Estate Inc - Mt Sterling, Imagine MLS
13.74 ACRESFreedom Realty & Property Management, Imagine MLS
35 ACRESBlock + Lot Real Estate, 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 17 new listings in Winchester, KY and 212 homes for sale.
| Home Size | Home Value* |
|---|---|
| 2 bedrooms (12 homes) | $165,387 |
| 3 bedrooms (68 homes) | $257,240 |
| 4 bedrooms (33 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.