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    284 homes

    KY/Clark/Winchester

    KY/Clark/Winchester

    Winchester Real Estate and Homes for Sale

    284 homes available
    NEW 4 hrs ago
    5705 Mount Sterling Road, Winchester, KY 40391
    $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
    NEW 9 hrs ago
    208 Royal Oak Drive, Winchester, KY 40391
    $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
    NEW 10 hrs ago
    946 Pine Ridge Road, Winchester, KY 40391
    $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
    NEW 33 hrs ago
    3431 Colby Road, Winchester, KY 40391
    $330,000
    4beds
    2bath
    sqft
    3.12acres
    House for Sale

    3431 Colby Road, Winchester, KY 40391

    Listing by: The Agency
    Pending
    305 Geronimo Court, Winchester, KY 40391
    $219,999
    3beds
    2bath
    1,150sqft
    0.43acres
    House for Sale

    305 Geronimo Court, Winchester, KY 40391

    Listing by: Lifstyl Real Estate
    Listed 5 days ago
    2 North Main Street, Winchester, KY 40391
    $1,595,000
    37beds
    19.5bath
    26,124sqft
    0.22acres
    Sale

    2 North Main Street, Winchester, KY 40391

    Listing by: Tsubaki Group, LLC
    Listed 5 days ago
    315 Newcastle Lane, Winchester, KY 40391
    $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
    Contingent
    115 Hampton Avenue, Winchester, KY 40391
    $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
    Pending
    259 Hibiscus Lane, Winchester, KY 40391
    $439,500
    4beds
    3.5bath
    3,921sqft
    0.61acres
    House for Sale

    259 Hibiscus Lane, Winchester, KY 40391

    Listing by: United Real Estate Bluegrass
    Pending
    279 Ascot Avenue, Winchester, KY 40391
    $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
    Contingent
    2950 Pretty Run Road, Winchester, KY 40391
    $690,500
    4beds
    3bath
    2,912sqft
    2.98acres
    House for Sale

    2950 Pretty Run Road, Winchester, KY 40391

    Listing by: Calumet Realty
    ContingentVirtual Tour
    213 Honeysuckle Lane, Winchester, KY 40391
    $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
    Pending
    210 Cabin Creek Road, Winchester, KY 40391
    $325,000
    3beds
    2bath
    1,584sqft
    1.98acres
    House for Sale

    210 Cabin Creek Road, Winchester, KY 40391

    Listing by: LPT Realty
    Price Reduced $10,000 Aug 13
    31 Vine Street, Winchester, KY 40391
    $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
    Contingent
    521 Hidden Hills Way, Winchester, KY 40391
    $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
    Contingent
    310 Sarah Court, Winchester, KY 40391
    $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
    ContingentVirtual Tour
    2 Chickadee Lane, Winchester, KY 40391
    $259,900
    3beds
    1.5bath
    1,397sqft
    0.28acres
    House for Sale

    2 Chickadee Lane, Winchester, KY 40391

    Listing by: Keller Williams Commonwealth
    1 - 40 of 284 results
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