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    Winchester, KY
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    Map
    316 Properties Available

    316 Properties Available

    The average price in the selected areas has remained stable. Learn more
    • Default
    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    190 Privacy Lane, Winchester, KY 40391
    1/34
    Active

    $260,000

    6.08 Acres

    190 Privacy Lane, Winchester, KY 40391

    Listed by Keller Williams Commonwealth

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    439 & 475 Old Muddy Creek Road, Winchester, KY 40391
    Active

    $109,900

    7.44 Acres

    439 & 475 Old Muddy Creek Road, Winchester, KY 40391

    Listed by Tom Goebel & Company

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    2996/3056 Irvine Road, Winchester, KY 40391
    1/23
    Active

    $498,900

    25.87 Acres

    2996/3056 Irvine Road, Winchester, KY 40391

    Listed by Rector Hayden Realtors

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    3056 Irvine Road, Winchester, KY 40391
    1/17
    Active

    $299,000

    14.51 Acres

    3056 Irvine Road, Winchester, KY 40391

    Listed by Rector Hayden Realtors

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    2996 Irvine Road, Winchester, KY 40391
    1/4
    Active

    $199,900

    11.36 Acres

    2996 Irvine Road, Winchester, KY 40391

    Listed by Rector Hayden Realtors

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    129 Lana Lane, Winchester, KY 40391
    Pending

    $449,000

    4 Beds3 Baths2,844 SqFt

    129 Lana Lane, Winchester, KY 40391

    Listed by Keller Williams Bluegrass Realty

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    1901 Winchester Avenue, Ashland, KY 41101
    1/32
    Active
    3D

    $8,500

    6,980 SqFt

    1901 Winchester Avenue, Ashland, KY 41101

    Listed by Rock N' Realty LLC

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    174 Pedro Way, Winchester, KY 40391
    1/2
    Pending

    $1,700

    978 Sqft Lot

    174 Pedro Way, Winchester, KY 40391

    Listed by EXP Realty, LLC

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    550 E Broadway Street, Winchester, KY 40391
    1/6
    Active

    $450,000

    8.26 Acres

    550 E Broadway Street, Winchester, KY 40391

    Listed by Coldwell Banker McMahan

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    308 Duclair Drive, Winchester, KY 40391
    1/11
    Active

    $50,000

    0.41 Acres

    308 Duclair Drive, Winchester, KY 40391

    Listed by Keller Williams Commonwealth

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    505 SHOPPERS Drive, Winchester, KY 40391
    1/38
    Pending

    $4,900

    3,700 SqFt

    505 SHOPPERS Drive, Winchester, KY 40391

    Listed by EXP Realty, LLC

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    1107 Winchester Avenue, Middlesboro, KY 40965
    1/4
    Active

    $49,900

    0.34 Acres

    1107 Winchester Avenue, Middlesboro, KY 40965

    Listed by Coldwell Banker Bisceglia Realty & Auction Co

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    2996/3056 Irvine Road, Winchester, KY 40391
    1/23
    Active

    $498,900

    25.87 Acres

    2996/3056 Irvine Road, Winchester, KY 40391

    Listed by Rector Hayden Realtors

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    3056 Irvine Road, Winchester, KY 40391
    1/17
    Active

    $299,000

    14.51 Acres

    3056 Irvine Road, Winchester, KY 40391

    Listed by Rector Hayden Realtors

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    2996 Irvine Road, Winchester, KY 40391
    1/4
    Active

    $199,900

    11.36 Acres

    2996 Irvine Road, Winchester, KY 40391

    Listed by Rector Hayden Realtors

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    100 Spencer Lane, Winchester, KY 40391
    1/4
    Active

    $100,000

    2.61 Acres

    100 Spencer Lane, Winchester, KY 40391

    Listed by FC Tucker Bluegrass

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    838 Bypass Road, Winchester, KY 40391
    1/12
    Active

    $614,900

    2,906 SqFt

    838 Bypass Road, Winchester, KY 40391

    Listed by Lifstyl Real Estate

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    152 W Broadway Street, Winchester, KY 40391
    1/24
    Pending

    $199,900

    2,844 SqFt

    152 W Broadway Street, Winchester, KY 40391

    Listed by Dream Maker Realty, LLC

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    2395 Paris Road, Winchester, KY 40391
    1/2
    Active

    $14,100,000

    274.52 Acres

    2395 Paris Road, Winchester, KY 40391

    Listed by Keller Williams Legacy Group

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    39 S Main Street, Winchester, KY 40391
    1/23
    Active

    $429,000

    3,538 SqFt

    39 S Main Street, Winchester, KY 40391

    Listed by Block + Lot Real Estate

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    13015 Irvine Road, Winchester, KY 40391
    1/20
    Active

    $219,000

    16.68 Acres

    13015 Irvine Road, Winchester, KY 40391

    Listed by Natural Bridge Realty

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    800 Winchester Road #125, Lexington, KY 40505
    1/4
    Active

    $7

    17,579 SqFt

    800 Winchester Road #125, Lexington, KY 40505

    Listed by Block + Lot Real Estate

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    220 Athens Boonsboro Road, Winchester, KY 40391
    1/47
    Active

    $531,000

    5,012 SqFt

    220 Athens Boonsboro Road, Winchester, KY 40391

    Listed by EXP Realty, LLC

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    5515 Van Meter Road, Winchester, KY 40391
    Pending

    $524,900

    4 Beds2 Baths2,940 SqFt

    5515 Van Meter Road, Winchester, KY 40391

    Listed by Woods Realty Group

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
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        Home
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        3. New Construction
        4. Featured Listings
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        Sell
        1. Sell My Home
        2. Recently Sold Properties
        About
        1. Podcast - The Torrey Smith Show
        2. Meet our Director of Marketing
        3. Shelbyville
        4. Contact Us
    Torrey Smith Realty Co., LLC

    Torrey Smith

    +1(502) 417-0910 torrey@smithclick.com

    529 Main Street, Shelbyville, KY, 40065, United States

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    Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
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        Home
        Our REALTORS®
        Quick Market Value
        Company Listings
        Stallard Springs
        Land & Farms
        1. Land & Farm Listings
        2. Recently Sold Farms
        3. 100+ Acres Currently For Sale
        Buy
        1. All Listings
        2. Listings under $200k in Shelby County
        3. New Construction
        4. Featured Listings
        5. Sold Listings
        6. Mortgage Calculator
        Sell
        1. Sell My Home
        2. Recently Sold Properties
        About
        1. Podcast - The Torrey Smith Show
        2. Meet our Director of Marketing
        3. Shelbyville
        4. Contact Us
    Torrey Smith Realty Co., LLC

    Torrey Smith

    +1(502) 417-0910 torrey@smithclick.com

    529 Main Street, Shelbyville, KY, 40065, United States

    Get My App

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.