
KY/Clark/WinchesterWinchester
KY/Clark/WinchesterWinchester
Winchester Real Estate and Homes for Sale
284 homes available
5705 Mount Sterling Road, Winchester, KY 40391
NEW 4 hrs ago
$399,000
4beds
2.5bath
2,980sqft
3.01acres
House for Sale
5705 Mount Sterling Road, Winchester, KY 40391
Listing by: Dream Maker Realty, LLC
208 Royal Oak Drive, Winchester, KY 40391
NEW 9 hrs ago
$469,900
4beds
2.5bath
2,593sqft
0.45acres
House for Sale
208 Royal Oak Drive, Winchester, KY 40391
Listing by: Keller Williams Legacy Group
946 Pine Ridge Road, Winchester, KY 40391
NEW 10 hrs ago
$500,000
4beds
2 full, 2 halfbath
3,523sqft
8.07acres
House for Sale
946 Pine Ridge Road, Winchester, KY 40391
Listing by: Kentucky Residential Real Estate, LLC
3431 Colby Road, Winchester, KY 40391
NEW 33 hrs ago
$330,000
4beds
2bath
–sqft
3.12acres
House for Sale
3431 Colby Road, Winchester, KY 40391
Listing by: The Agency
305 Geronimo Court, Winchester, KY 40391
Pending
$219,999
3beds
2bath
1,150sqft
0.43acres
House for Sale
305 Geronimo Court, Winchester, KY 40391
Listing by: Lifstyl Real Estate
2 North Main Street, Winchester, KY 40391
Listed 5 days ago
$1,595,000
37beds
19.5bath
26,124sqft
0.22acres
Sale
2 North Main Street, Winchester, KY 40391
Listing by: Tsubaki Group, LLC
315 Newcastle Lane, Winchester, KY 40391
Listed 5 days ago
$259,900
3beds
2.5bath
1,544sqft
0.1acres
House for Sale
315 Newcastle Lane, Winchester, KY 40391
Listing by: Keller Williams Commonwealth
106 West Hickman Street, Winchester, KY 40391
$230,000
3beds
2bath
1,836sqft
0.08acres
House for Sale
106 West Hickman Street, Winchester, KY 40391
Listing by: Bluegrass Realty Pros, Inc
102 West Hickman Street, Winchester, KY 40391
$171,000
2beds
1bath
870sqft
0.1acres
House for Sale
102 West Hickman Street, Winchester, KY 40391
Listing by: Bluegrass Realty Pros, Inc
115 Hampton Avenue, Winchester, KY 40391
Contingent
$325,000
4beds
2.5bath
3,042sqft
0.6acres
House for Sale
115 Hampton Avenue, Winchester, KY 40391
Listing by: Deborah Ball Realty
133 South Highland Street, Winchester, KY 40391
$251,000
6beds
3bath
2,302sqft
0.08acres
Sale
133 South Highland Street, Winchester, KY 40391
Listing by: Bluegrass Realty Pros, Inc
206 Chaplin Avenue, Winchester, KY 40391
$131,000
2beds
1bath
804sqft
0.18acres
House for Sale
206 Chaplin Avenue, Winchester, KY 40391
Listing by: Bluegrass Realty Pros, Inc
16 Central Avenue, Winchester, KY 40391
$290,000
6beds
4bath
2,511sqft
0.15acres
Sale
16 Central Avenue, Winchester, KY 40391
Listing by: Bluegrass Realty Pros, Inc
136 Alabama Street, Winchester, KY 40391
$224,000
3beds
1bath
1,645sqft
0.17acres
House for Sale
136 Alabama Street, Winchester, KY 40391
Listing by: Bluegrass Realty Pros, Inc
1028 West Lexington Avenue, Winchester, KY 40391
$426,000
5beds
4bath
–sqft
0.18acres
Sale
1028 West Lexington Avenue, Winchester, KY 40391
Listing by: Bluegrass Realty Pros, Inc
5045 Van Meter Road, Winchester, KY 40391
$3,330,000
6beds
5.5bath
7,274sqft
78acres
House for Sale
5045 Van Meter Road, Winchester, KY 40391
Listing by: Keller Williams Bluegrass Realty
211 College Street, Winchester, KY 40391
$270,000
4beds
2bath
2,056sqft
0.18acres
Sale
211 College Street, Winchester, KY 40391
Listing by: Bluegrass Realty Pros, Inc
259 Hibiscus Lane, Winchester, KY 40391
Pending
$439,500
4beds
3.5bath
3,921sqft
0.61acres
House for Sale
259 Hibiscus Lane, Winchester, KY 40391
Listing by: United Real Estate Bluegrass
279 Ascot Avenue, Winchester, KY 40391
Pending
$299,000
4beds
2.5bath
2,247sqft
0.38acres
House for Sale
279 Ascot Avenue, Winchester, KY 40391
Listing by: Team Pannell Real Estate
188 Big Stoner Road, Winchester, KY 40391
$419,000
4beds
2.5bath
2,388sqft
1.19acres
House for Sale
188 Big Stoner Road, Winchester, KY 40391
Listing by: RE/MAX Creative Realty
208 Citation Court, Winchester, KY 40391
$360,000
2beds
2bath
1,568sqft
0.15acres
House for Sale
208 Citation Court, Winchester, KY 40391
Listing by: Tom Goebel & Company
3056 Irvine Road, Winchester, KY 40391
$329,900
14.51acres
Land for Sale
3056 Irvine Road, Winchester, KY 40391
Listing by: Rector Hayden Realtors
2996 Irvine Road, Winchester, KY 40391
$199,900
11.36acres
Land for Sale
2996 Irvine Road, Winchester, KY 40391
Listing by: Rector Hayden Realtors
2996/3056 Irvine Road, Winchester, KY 40391
$529,800
25.87acres
Land for Sale
2996/3056 Irvine Road, Winchester, KY 40391
Listing by: Rector Hayden Realtors
130 Winterberry Circle, Winchester, KY 40391
$535,000
5beds
3.5bath
3,741sqft
0.36acres
House for Sale
130 Winterberry Circle, Winchester, KY 40391
Listing by: Freedom Realty & Property Management
3614 Stamper Drive, Winchester, KY 40391
$269,950
3beds
2bath
1,247sqft
0.13acres
House for Sale
3614 Stamper Drive, Winchester, KY 40391
Listing by: Dream Maker Realty, LLC
521 Acadia Way, Winchester, KY 40391
$225,000
4beds
2bath
1,370sqft
0.24acres
House for Sale
521 Acadia Way, Winchester, KY 40391
Listing by: The Brokerage
511 Acadia Way, Winchester, KY 40391
$225,000
4beds
2bath
1,400sqft
0.21acres
House for Sale
511 Acadia Way, Winchester, KY 40391
Listing by: The Brokerage
2950 Pretty Run Road, Winchester, KY 40391
Contingent
$690,500
4beds
3bath
2,912sqft
2.98acres
House for Sale
2950 Pretty Run Road, Winchester, KY 40391
Listing by: Calumet Realty
213 Honeysuckle Lane, Winchester, KY 40391
ContingentVirtual Tour
$398,000
4beds
2 full, 2 halfbath
3,087sqft
0.21acres
House for Sale
213 Honeysuckle Lane, Winchester, KY 40391
Listing by: Keller Williams Commonwealth
9711 Ironworks Road, Winchester, KY 40391
$225,000
18.38acres
Farm for Sale
9711 Ironworks Road, Winchester, KY 40391
Listing by: Denniston Realty
210 Cabin Creek Road, Winchester, KY 40391
Pending
$325,000
3beds
2bath
1,584sqft
1.98acres
House for Sale
210 Cabin Creek Road, Winchester, KY 40391
Listing by: LPT Realty
31 Vine Street, Winchester, KY 40391
Price Reduced $10,000 Aug 13
$215,000
3beds
1bath
1,443sqft
0.16acres
House for Sale
31 Vine Street, Winchester, KY 40391
Listing by: Rock N' Realty LLC
180 Casa Landa Way, Winchester, KY 40391
$650,000
4beds
3.5bath
4,779sqft
0.39acres
House for Sale
180 Casa Landa Way, Winchester, KY 40391
Listing by: United Real Estate Bluegrass
521 Hidden Hills Way, Winchester, KY 40391
Contingent
$219,000
3beds
2bath
1,335sqft
0.01acres
House for Sale
521 Hidden Hills Way, Winchester, KY 40391
Listing by: Rector Hayden Realtors
406 West Washington Street, Winchester, KY 40391
$9,950
2beds
1bath
1,428sqft
0.17acres
House for Sale
406 West Washington Street, Winchester, KY 40391
Listing by: Rookard Real Estate Consultants
210 College Street, Winchester, KY 40391
$419,900
4beds
3.5bath
2,718sqft
0.17acres
House for Sale
210 College Street, Winchester, KY 40391
Listing by: Christies International Real Estate Bluegrass
310 Sarah Court, Winchester, KY 40391
Contingent
$213,900
3beds
2bath
1,072sqft
0.14acres
House for Sale
310 Sarah Court, Winchester, KY 40391
Listing by: RO&CO Real Estate
136 College Street, Winchester, KY 40391
$412,900
4beds
4.5bath
2,800sqft
0.17acres
House for Sale
136 College Street, Winchester, KY 40391
Listing by: The Brokerage
2 Chickadee Lane, Winchester, KY 40391
ContingentVirtual Tour
$259,900
3beds
1.5bath
1,397sqft
0.28acres
House for Sale
2 Chickadee Lane, Winchester, KY 40391
Listing by: Keller Williams Commonwealth
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Nearby County

2250 Regency Road Lexington, KY 40503
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