
Winchester Real Estate and Homes for Sale
290 homes available
415 David Lane, Winchester, KY 40391
$579,000
4beds
2.5bath
3,989sqft
0.49acres
House for Sale
415 David Lane, Winchester, KY 40391
Listing by: Bridgewater Real Estate
151 Hilltop Drive, Winchester, KY 40391
Pending
$275,000
4beds
1.5bath
1,873sqft
0.56acres
House for Sale
151 Hilltop Drive, Winchester, KY 40391
Listing by: Kentucky Residential Real Estate, LLC
1701 Gay Evans Road, Winchester, KY 40391
$890,000
4beds
3.5bath
4,221sqft
8.33acres
House for Sale
1701 Gay Evans Road, Winchester, KY 40391
Listing by: Coldwell Banker McMahan
2447 Clintonville Road, Winchester, KY 40391
$949,000
5beds
4bath
4,058sqft
3acres
House for Sale
2447 Clintonville Road, Winchester, KY 40391
Listing by: Berkshire Hathaway de Movellan Properties
199 Midway Road, Winchester, KY 40391
Price Reduced $8,000 Aug 8
$51,000
5.59acres
Land for Sale
199 Midway Road, Winchester, KY 40391
Listing by: Dream Maker Realty, LLC
356 Boone Avenue, Winchester, KY 40391
$357,000
4beds
3bath
3,200sqft
0.21acres
House for Sale
356 Boone Avenue, Winchester, KY 40391
Listing by: Rector Hayden Realtors
517 Hidden Hills Way, Winchester, KY 40391
Contingent
$183,000
3beds
2bath
1,120sqft
0.09acres
House for Sale
517 Hidden Hills Way, Winchester, KY 40391
Listing by: Bridgewater Real Estate
1397 Gay Evans Road, Winchester, KY 40391
$149,900
6.32acres
Land for Sale
1397 Gay Evans Road, Winchester, KY 40391
Listing by: The Agency
1445 Gay Evans Road, Winchester, KY 40391
$139,900
5.67acres
Land for Sale
1445 Gay Evans Road, Winchester, KY 40391
Listing by: The Agency
1541 Gay Evans Road, Winchester, KY 40391
$149,900
5.6acres
Land for Sale
1541 Gay Evans Road, Winchester, KY 40391
Listing by: The Agency
1495 Gay Evans Road, Winchester, KY 40391
$139,900
5.02acres
Land for Sale
1495 Gay Evans Road, Winchester, KY 40391
Listing by: The Agency
1045 Gay Evans Road, Winchester, KY 40391
$189,900
10.73acres
Land for Sale
1045 Gay Evans Road, Winchester, KY 40391
Listing by: The Agency
995 Gay Evans Road, Winchester, KY 40391
$199,900
11.33acres
Land for Sale
995 Gay Evans Road, Winchester, KY 40391
Listing by: The Agency
1600 Ironworks Road, Winchester, KY 40391
$799,900
13.19acres
Farm for Sale
1600 Ironworks Road, Winchester, KY 40391
Listing by: Freedom Realty & Property Management
1203 Irvine Road, Winchester, KY 40391
ContingentVirtual Tour
$949,900
12.38acres
Land for Sale
1203 Irvine Road, Winchester, KY 40391
Listing by: Freedom Realty & Property Management
439 Lynnway Drive, Winchester, KY 40391
$619,000
6beds
3.5bath
5,226.6sqft
0.43acres
House for Sale
439 Lynnway Drive, Winchester, KY 40391
Listing by: Dream Maker Realty, LLC
6699 Boonesboro Road, Winchester, KY 40391
$195,000
8.35acres
Farm for Sale
6699 Boonesboro Road, Winchester, KY 40391
Listing by: RE/MAX Elite Lexington
425 Alexis Way, Winchester, KY 40391
$785,000
4beds
2.5bath
2,476sqft
0.31acres
House for Sale
425 Alexis Way, Winchester, KY 40391
Listing by: Keller Williams Commonwealth
10 French Avenue, Winchester, KY 40391
Contingent
$499,000
5beds
3bath
3,262sqft
0.38acres
House for Sale
10 French Avenue, Winchester, KY 40391
Listing by: Keller Williams Bluegrass Realty
37 7th Street, Winchester, KY 40391
$235,000
3beds
2bath
1,680sqft
0.24acres
House for Sale
37 7th Street, Winchester, KY 40391
Listing by: Coldwell Banker McMahan
424 Alexis Way, Winchester, KY 40391
$625,000
3beds
2.5bath
2,405sqft
0.31acres
House for Sale
424 Alexis Way, Winchester, KY 40391
Listing by: Keller Williams Commonwealth
422 Alexis Way, Winchester, KY 40391
$635,000
4beds
2.5bath
2,537sqft
0.31acres
House for Sale
422 Alexis Way, Winchester, KY 40391
Listing by: Keller Williams Commonwealth
415 Alexis Way, Winchester, KY 40391
$700,000
3beds
2bath
2,400sqft
0.31acres
House for Sale
415 Alexis Way, Winchester, KY 40391
Listing by: Keller Williams Commonwealth
414 Alexis Way, Winchester, KY 40391
$665,000
3beds
2.5bath
2,643sqft
0.31acres
House for Sale
414 Alexis Way, Winchester, KY 40391
Listing by: Keller Williams Commonwealth
113 Bella Shae Way, Winchester, KY 40391
$670,000
3beds
2bath
2,261sqft
0.31acres
House for Sale
113 Bella Shae Way, Winchester, KY 40391
Listing by: Keller Williams Commonwealth
111 Bella Shae Way, Winchester, KY 40391
$825,000
3beds
2.5bath
2,995sqft
0.31acres
House for Sale
111 Bella Shae Way, Winchester, KY 40391
Listing by: Keller Williams Commonwealth
107 Bella Shae Way, Winchester, KY 40391
$550,000
3beds
2.5bath
2,200sqft
0.31acres
House for Sale
107 Bella Shae Way, Winchester, KY 40391
Listing by: Keller Williams Commonwealth
106 Bella Shae Way, Winchester, KY 40391
$645,000
4beds
2.5bath
2,526sqft
0.31acres
House for Sale
106 Bella Shae Way, Winchester, KY 40391
Listing by: Keller Williams Commonwealth
217 Morris Road, Winchester, KY 40391
$275,000
4beds
2bath
1,924sqft
1.48acres
House for Sale
217 Morris Road, Winchester, KY 40391
Listing by: Keller Williams Commonwealth
2721 Pretty Run Road, Winchester, KY 40391
Pending
$250,000
3beds
2bath
1,456sqft
5acres
House for Sale
2721 Pretty Run Road, Winchester, KY 40391
Listing by: RE/MAX Creative, Winchester
222 HOLIDAY Road, Winchester, KY 40391
$209,900
3beds
1bath
1,100sqft
0.33acres
House for Sale
222 HOLIDAY Road, Winchester, KY 40391
Listing by: Herald Real Estate
380 Della Winchester Road, Nancy, KY 42544
Contingent
$125,000
1beds
1bath
396sqft
29.56acres
House for Sale
380 Della Winchester Road, Nancy, KY 42544
Listing by: Berkshire Hathaway HomeServices Foster Realtors
102 Augusta Drive, Winchester, KY 40391
$29,000
0.46acres
Land for Sale
102 Augusta Drive, Winchester, KY 40391
Listing by: Dream Maker Realty, LLC
7950 Four Mile Road, Winchester, KY 40391
$139,000
11.47acres
Farm for Sale
7950 Four Mile Road, Winchester, KY 40391
Listing by: Keller Williams Legacy Group
Winchester
Median Sale Price
$ 235,250
NaN % year-over-year
# of Homes Sold
326
NaN % year-over-year
Median Days On Market
26
NaN % year-over-year
Nearby City
Lexington Homes For SaleMt Sterling Homes For SaleParis Homes For SaleRichmond Homes For SaleWaco Homes For SaleWinchester Homes For Sale
Nearby Zip Code
40353 Homes For Sale40361 Homes For Sale40385 Homes For Sale40391 Homes For Sale40475 Homes For Sale40509 Homes For Sale40515 Homes For Sale40516 Homes For Sale
Nearby County

2250 Regency Road Lexington, KY 40503
© 2025 Imagine MLS
Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
