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    Downtown, Winchester, KY
    Price
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      • $ 50,000
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      • $ 150,000
      • $ 200,000
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      • $ 200,000
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    Baths
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    • Map
    Map
    18 Properties Available

    18 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)
    120 Jackson Street, Winchester, KY 40391
    1/25
    Active

    $248,000

    3 Beds3 Baths1,342 SqFt

    120 Jackson Street, Winchester, KY 40391

    Listed by Coldwell Banker McMahan

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    115 College Street, Winchester, KY 40391
    1/37
    Pending

    $300,000

    3 Beds2 Baths1,839 SqFt

    115 College Street, Winchester, KY 40391

    Listed by Keller Williams Legacy Group

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    205 E Washington Street, Winchester, KY 40391
    1/4
    Price Dropped by $5K

    $124,900

    4 Beds3 Baths2,131 SqFt

    205 E Washington Street, Winchester, KY 40391

    Listed by Keller Williams Commonwealth

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    218 E Washington Street, Winchester, KY 40391
    1/33
    Active

    $225,000

    4 Beds1 Bath1,743 SqFt

    218 E Washington Street, Winchester, KY 40391

    Listed by Rector Hayden Realtors

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    221 S Highland Street, Winchester, KY 40391
    1/13
    Price Dropped by $5K

    $252,500

    5 Beds3 Baths3,007 SqFt

    221 S Highland Street, Winchester, KY 40391

    Listed by The Brokerage

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    175 Magnolia Street, Winchester, KY 40391
    1/12
    Price Dropped by $24K

    $175,000

    3 Beds1 Bath1,046 SqFt

    175 Magnolia Street, Winchester, KY 40391

    Listed by Woods Realty Group

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    146 Cook Avenue, Winchester, KY 40391
    1/22
    Price Dropped by $2K

    $167,500

    3 Beds1 Bath1,274 SqFt

    146 Cook Avenue, Winchester, KY 40391

    Listed by National Real Estate

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    130 E Broadway Street, Winchester, KY 40391
    1/13
    Active

    $245,000

    5 Beds3 Baths2,445 SqFt

    130 E Broadway Street, Winchester, KY 40391

    Listed by Lifstyl Real Estate

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    27 Ashland Avenue, Winchester, KY 40391
    1/24
    Price Dropped by $1K

    $188,900

    3 Beds2 Baths1,653 SqFt

    27 Ashland Avenue, Winchester, KY 40391

    Listed by Marshall Lane Real Estate - Lexington

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    2 N Main Street, Winchester, KY 40391
    1/37
    Active

    $1,595,000

    37 Beds20 Baths26,124 SqFt

    2 N Main Street, Winchester, KY 40391

    Listed by Tsubaki Group, LLC

    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)
    33-41 Winn Avenue, Winchester, KY 40391
    1/2
    New

    $550,000

    1.53 Acres

    33-41 Winn Avenue, Winchester, KY 40391

    Listed by eXp Realty, LLC

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    37 S Main Street, Winchester, KY 40391
    1/14
    Active

    $3,150

    2,574 SqFt

    37 S Main Street, Winchester, KY 40391

    Listed by United Real Estate Bluegrass

    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)
    29 S South Main Street, Winchester, KY 40391
    1/4
    Active

    $2,000

    3,920 Sqft Lot

    29 S South Main Street, Winchester, KY 40391

    Listed by Block + Lot Real Estate

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

    $525,000

    5,054 SqFt

    808 Bypass Road, Winchester, KY 40391

    Listed by Lifstyl Real Estate

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    18 N Main Street, Winchester, KY 40391
    1/20
    Active

    $299,900

    5,227 Sqft Lot

    18 N Main Street, Winchester, KY 40391

    Listed by United Real Estate Bluegrass

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    395 Croxton Way, Winchester, KY 40391
    1/10
    Pending

    $374,900

    1.29 Acres

    395 Croxton Way, Winchester, KY 40391

    Listed by Rector Hayden Realtors

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    • 1
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        Home
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        About
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        3. Shelbyville
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    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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        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.