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    Winchester, KY
    Price
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      • $ 50,000
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      • $ 150,000
      • $ 200,000
      • $ 400,000
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      • $ 200,000
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    Beds
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    Baths
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      • 1.5
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    • Map
    Map
    317 Properties Available

    317 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)
    102 W Hickman Street, Winchester, KY 40391
    1/6
    Active

    $171,000

    2 Beds1 Bath870 SqFt

    102 W Hickman Street, Winchester, KY 40391

    Listed by Bluegrass Realty Pros, Inc

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    5045 Van Meter Road, Winchester, KY 40391
    1/103
    Active

    $3,500,000

    6 Beds6 Baths7,274 SqFt

    5045 Van Meter Road, Winchester, KY 40391

    Listed by Keller Williams Bluegrass Realty

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    188 Big Stoner Road, Winchester, KY 40391
    1/71
    Pending

    $419,000

    4 Beds3 Baths2,388 SqFt

    188 Big Stoner Road, Winchester, KY 40391

    Listed by RE/MAX Creative Realty

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    208 Citation Court, Winchester, KY 40391
    1/36
    Active

    $345,000

    2 Beds2 Baths1,568 SqFt

    208 Citation Court, Winchester, KY 40391

    Listed by Tom Goebel & Company

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    3614 Stamper Drive, Winchester, KY 40391
    1/62
    Active

    $259,500

    3 Beds2 Baths1,247 SqFt

    3614 Stamper Drive, Winchester, KY 40391

    Listed by Dream Maker Realty, LLC

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    521 Acadia Way, Winchester, KY 40391
    1/22
    Price Dropped by $3K

    $221,500

    4 Beds2 Baths1,370 SqFt

    521 Acadia Way, Winchester, KY 40391

    Listed by The Brokerage

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    180 Casa Landa Way, Winchester, KY 40391
    1/85
    Active

    $609,900

    4 Beds4 Baths4,779 SqFt

    180 Casa Landa Way, Winchester, KY 40391

    Listed by United Real Estate Bluegrass

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    808 Bypass Road, Winchester, KY 40391
    1/58
    Active

    $525,000

    2 Beds2 Baths5,054 SqFt

    808 Bypass Road, Winchester, KY 40391

    Listed by Lifstyl Real Estate

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    271 April Way, Winchester, KY 40391
    1/26
    Pending

    $215,000

    2 Beds2 Baths1,120 SqFt

    271 April Way, Winchester, KY 40391

    Listed by Keller Williams Commonwealth

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    160 Agawam Road, Winchester, KY 40391
    1/80
    Pending

    $524,000

    3 Beds3 Baths4,933 SqFt

    160 Agawam Road, Winchester, KY 40391

    Listed by Keller Williams Legacy Group

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    122 LeAnn Lane, Winchester, KY 40391
    1/37
    Pending

    $379,000

    4 Beds3 Baths2,587 SqFt

    122 LeAnn Lane, Winchester, KY 40391

    Listed by Tom Goebel & Company

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    118 Windridge Drive, Winchester, KY 40391
    1/41
    Price Dropped by $7K

    $318,000

    3 Beds2 Baths1,617 SqFt

    118 Windridge Drive, Winchester, KY 40391

    Listed by RE/MAX Creative, Winchester

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    39 S Highland Street, Winchester, KY 40391
    1/9
    Active

    $102,000

    2 Beds1 Bath552 SqFt

    39 S Highland Street, Winchester, KY 40391

    Listed by Bluegrass Realty Pros, Inc

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    228 Jackson Street, Winchester, KY 40391
    1/3
    Active

    $146,000

    3 Beds1 Bath1,020 SqFt

    228 Jackson Street, Winchester, KY 40391

    Listed by Bluegrass Realty Pros, Inc

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    150 Cook Avenue, Winchester, KY 40391
    1/12
    Active

    $144,000

    3 Beds1 Bath805 SqFt

    150 Cook Avenue, Winchester, KY 40391

    Listed by Bluegrass Realty Pros, Inc

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    101 E Lexington Avenue, Winchester, KY 40391
    1/6
    Active

    $388,000

    5 Beds3 Baths2,762 SqFt

    101 E Lexington Avenue, Winchester, KY 40391

    Listed by Bluegrass Realty Pros, Inc

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    700 Nick Lane, Winchester, KY 40391
    1/37
    Pending

    $949,950

    3 Beds3 Baths2,400 SqFt

    700 Nick Lane, Winchester, KY 40391

    Listed by Dream Maker Realty, LLC

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    5045 Van Meter Road, Winchester, KY 40391
    1/103
    Active

    $2,650,000

    6 Beds6 Baths7,274 SqFt

    5045 Van Meter Road, Winchester, KY 40391

    Listed by Keller Williams Bluegrass Realty

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    175 Chatham Place, Winchester, KY 40391
    Active

    $5,646,000

    2 Beds3 Baths37,192 SqFt

    175 Chatham Place, Winchester, KY 40391

    Listed by Milton and Associates Real Estate

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    40 Garner Street, Winchester, KY 40391
    1/30
    Price Dropped by $4K

    $210,500

    3 Beds1 Bath1,354 SqFt

    40 Garner Street, Winchester, KY 40391

    Listed by Guide Realty, Inc.

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    1150 Craig Crossing, Winchester, KY 40391
    1/69
    Active

    $925,000

    5 Beds4 Baths2,842 SqFt

    1150 Craig Crossing, Winchester, KY 40391

    Listed by Kentucky Residential Real Estate, LLC

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    225 Evergreen Drive, Winchester, KY 40391
    1/3
    Active

    $345,000

    3 Beds2 Baths1,677 SqFt

    225 Evergreen Drive, Winchester, KY 40391

    Listed by United Real Estate Bluegrass

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    220 Evergreen Drive, Winchester, KY 40391
    1/3
    Active

    $430,000

    3 Beds2 Baths1,855 SqFt

    220 Evergreen Drive, Winchester, KY 40391

    Listed by United Real Estate Bluegrass

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    250 Evergreen Drive, Winchester, KY 40391
    1/3
    Active

    $430,000

    3 Beds2 Baths1,855 SqFt

    250 Evergreen Drive, Winchester, KY 40391

    Listed by United Real Estate Bluegrass

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
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        Home
        Our REALTORS®
        Quick Market Value
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        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.
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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.