Homes for Sale in Winchester
“Discover 208 homes in Winchester, Kentucky”
Winchester Real Estate at a Glance
Current market statistics for Winchester, KY
208
Active Listings
$527K
Avg Price
$285K
Median Price
$174
Price/Sqft
3,035
Avg Sqft
389
Avg Days
Price Range
From
$29,000
To
$14,100,000
Nearby Cities
Explore homes for sale in cities near Winchester, Kentucky
Editor's Picks
Our curated selection of the finest winchester homes
More Winchester Homes
More standout listings from across the Winchester market
$725K
186 Chardonnay Court
Winchester, KY
$325K
“3 Bed 2 Bath Single Family Home on 2.04 Acres in Winchester KY”
4305 Old Boonesboro Road
Winchester, KY
$275K
“2 Bedroom 1 Bath Single Family Cabin on 5 Acres in Winchester KY”
955 Right Angle Road
Winchester, KY
$199K
“2 Bedroom 2 Bath Townhouse in Royal Oaks Village Winchester KY”
104 Bay Hill Drive
Winchester, KY
$500K
16 Manor Drive
Winchester, KY
$340K
410 W Lexington Avenue
Winchester, KY
$269K
104 Jackson Ferry Road
Winchester, KY
$180K
229 S Highland Street
Winchester, KY
Homes for Sale in Winchester
Every active listing in Winchester, browsable page by page.
$350K
6888 Bybee Road
Winchester, KY
$355K
119 Gibson Way
Winchester, KY
$290K
198 Hilltop Drive
Winchester, KY
$310K
872 Stratton Lane
Winchester, KY
$155K
220 E Washington Street
Winchester, KY
$200K
18 N Main Street
Winchester, KY
$400K
“7.31-Acre Rural Land Lot in Winchester KY Clark County”
4095 Basin Springs Road
Winchester, KY
$235K
122 Spruce Court
Winchester, KY
$330K
335 Newcastle Lane
Winchester, KY
$350K
410 W Lexington Avenue
Winchester, KY
$420K
19 Fontaine Boulevard
Winchester, KY
$289K
214 S Burns Avenue
Winchester, KY
$330K
8 Monroe Avenue
Winchester, KY
$153K
65 Fitch Avenue
Winchester, KY
$250K
312 Buffalo Trace
Winchester, KY
$385K
309 Gallahadion Court
Winchester, KY
$250K
3150 Waterworks Road
Winchester, KY
$545K
665 Lillies Ferry Road
Winchester, KY
$1.3M
1200 Craig Crossing
Winchester, KY
$230K
2 Western Avenue
Winchester, KY
$250K
17 Holiday Road
Winchester, KY
$247K
30 Virginia Avenue
Winchester, KY
$355K
107 Gibson Way
Winchester, KY
$550K
600 Boone Avenue
Winchester, KY
$250K
377 Crescent Avenue
Winchester, KY
$155K
750 Craig Crossing lot: #7
Winchester, KY
$275K
“2 Bedroom 1 Bath Single Family Cabin on 5 Acres in Winchester KY”
955 Right Angle Road
Winchester, KY
$949K
330 Spencer Lane
Winchester, KY
$240K
13 Long Avenue
Winchester, KY
$464K
105 Monet Boulevard
Winchester, KY
$340K
23 Windridge Drive
Winchester, KY
$939K
200 Old Log Lick Road
Winchester, KY
$100K
563 Constitution Drive
Winchester, KY
$265K
119 Sunset Heights
Winchester, KY
$295K
162 French Avenue
Winchester, KY
$235K
528 Estes Drive
Winchester, KY
$340K
410 W Lexington Avenue
Winchester, KY
$360K
3359 Trapp-Goffs Corner Road
Winchester, KY
$795K
6356 Van Meter Road
Winchester, KY
$199K
“2 Bedroom 2 Bath Townhouse in Royal Oaks Village Winchester KY”
104 Bay Hill Drive
Winchester, KY
$785K
7300 Old Boonesboro Road
Winchester, KY
$1.6M
599 BLT Way
Winchester, KY
$238K
125 Kittison Drive
Winchester, KY
$233K
14 Cook Avenue
Winchester, KY
$390K
23 Wheeler Avenue
Winchester, KY
$278K
116 Sturbridge Lane
Winchester, KY
$1.7M
3166 Colby Road
Winchester, KY
$200K
225 Buffalo Trace
Winchester, KY
$100K
2799 Pine Ridge Road
Winchester, KY
$14.1M
2395 Paris Road
Winchester, KY
Showing 1–50 of 208 · Page 1 of 5
Continue exploring Winchester
Turn the listings into a short list with a clearer read on the Winchester market, its neighborhoods, and the home features that matter to you.
Winchester Housing Market
Winchester, Kentucky provides a welcoming small-town atmosphere that attracts families, retirees, and professionals seeking a quieter pace while remaining within reach of Lexington for work and larger amenities. The character varies by neighborhood, with a mix of established residential areas and more rural settings on the outskirts that appeal to different preferences for space and community feel. Residents enjoy local parks for recreation, a selection of dining options that include casual eateries and traditional Kentucky dishes, and outdoor activities in the surrounding countryside.
Read the full market guide
Many buyers are drawn here for reasonable commutes to employment centers in the region along with community facilities that support everyday living without a rushed urban tempo. The area is served by the local public school district and nearby private options, giving families several choices for education. Winchester experiences four distinct seasons, marked by warm humid summers and winters that bring cooler temperatures along with occasional light snow. In the current market there are 208 active listings. The median price stands at $284,950 while the average reaches $527,491, and homes average 3,035 square feet with properties remaining on the market for an average of 389 days across a wide price range.
Median list price $284,950 · Range $29,000–$14,100,000 · 208 active listings
Frequently Asked Questions
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