Winchester, KY Real Estate & Homes For Sale
214 homes
Use arrow keys to navigateNEW - 2 MIN AGO0.33 ACRESFC Tucker Bluegrass, Imagine MLS
Use arrow keys to navigateNEW - 1 DAY AGOColdwell Banker McMahan, Imagine MLS
Use arrow keys to navigateNEW CONSTRUCTIONBUILDABLE PLAN
Use arrow keys to navigateNEWTRULIA PREVIEW
3D VIEW
Use arrow keys to navigate3D VIEW9.09 ACRESRE/MAX Creative, Winchester, Imagine MLS
Use arrow keys to navigateAUCTION
Use arrow keys to navigate0.43 ACRESFC Tucker Bluegrass, Imagine MLS
0.35 ACRESKeller Williams Legacy Group, Imagine MLS
2.83 ACRESKentucky Residential Real Estate, LLC, Imagine MLS
AUCTION1.64 ACRESKeller Williams Commonwealth, Imagine MLS
NEW CONSTRUCTIONBUILDABLE PLAN
0.61 ACRESRogers Realty, LLC, Imagine MLS
3D VIEW0.36 ACRESRE/MAX Creative, Winchester, Imagine MLS
Four Seasons Realty, Imagine MLS
OPEN SUN, 1-3PMThe Brokerage, Imagine MLS
0.45 ACRESColdwell Banker McMahan, Imagine MLS
6.54 ACRESWEICHERT REALTORS - Ford Brothers, Imagine MLS
FOR SALE BY OWNER
3D VIEWLifstyl Real Estate, Imagine MLS
3D VIEWLois Ann Disponett Real Est, Imagine MLS
Keller Williams Legacy Group, Imagine MLS
0.37 ACRESPower House Realty, Imagine MLS
1.01 ACRESUnited Real Estate Bluegrass, Imagine MLS
1 ACREUnited Real Estate Bluegrass, Imagine MLS
1.03 ACRESUnited Real Estate Bluegrass, Imagine MLS
1.11 ACRESUnited Real Estate Bluegrass, Imagine MLS
3D VIEWKeller Williams Legacy Group, Imagine MLS
Freedom Realty & Property Management, Imagine MLS
Ensor Real Estate, LLC, Imagine MLS
OPEN SUN, 2-4PMeXp Realty, LLC, Imagine MLS
3D VIEW77 ACRESBluegrass Sotheby's International Realty, Imagine MLS
0.52 ACRESBluegrass Home Group, Imagine MLS
147.98 ACRESSteven D Adams Real Estate Services, LLC, Imagine MLS
OPEN SUN, 1-3PMRE/MAX Creative, Winchester, Imagine MLS
3D VIEW12.81 ACRESBluegrass Sotheby's International Realty, Imagine MLS
18 ACRESDream Maker Realty, 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 $251,145
| Month | Median home value |
|---|---|
| October 2025 | $241k |
| November 2025 | $242k |
| December 2025 | $244k |
| January 2026 | $245k |
| February 2026 | $246k |
| March 2026 | $247k |
| April 2026 | $248k |
| May 2026 | $249k |
| June 2026 | $250k |
| July 2026 | $251k |
| August 2026 | $251k |
| September 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 7 new listings in Winchester, KY and 214 homes for sale.
| Home Size | Home Value* |
|---|---|
| 2 bedrooms (18 homes) | $163,875 |
| 3 bedrooms (85 homes) | $257,843 |
| 4 bedrooms (22 homes) | $338,839 |
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.
Browse Winchester, KY homes by type
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.