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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)
    6237 Bybee Road, Winchester, KY 40391
    Active

    $1,200,000

    5 Beds7 Baths8,236 SqFt

    6237 Bybee Road, Winchester, KY 40391

    Listed by Berkshire Hathaway HomeServices Foster Realtors

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    1940 Athens Boonesboro Road, Winchester, KY 40391
    1/19
    Active

    $125,000

    4.01 Acres

    1940 Athens Boonesboro Road, Winchester, KY 40391

    Listed by Kentucky Land and Home

    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)
    30 N Main Street, Winchester, KY 40391
    1/9
    Active

    $2,500

    3,000 SqFt

    30 N 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)
    1108 W Lexington Avenue, Winchester, KY 40391
    1/7
    Pending

    $800,000

    4.87 Acres

    1108 W Lexington Avenue, Winchester, KY 40391

    Listed by Kentucky Residential Real Estate, LLC

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    368 Flanagan Station Road, Winchester, KY 40391
    1/9
    Active

    $206,000

    7.77 Acres

    368 Flanagan Station Road, Winchester, KY 40391

    Listed by Keller Williams Commonwealth

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    205 Codella Drive, Winchester, KY 40391
    1/14
    Active

    $650,000

    3 Acres

    205 Codella Drive, Winchester, KY 40391

    Listed by Block + Lot Real Estate

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    1901 Winchester Avenue, Ashland, KY 41101
    1/38
    Active
    3D

    $1,100,000

    6,980 SqFt

    1901 Winchester Avenue, Ashland, KY 41101

    Listed by Rock N' Realty LLC

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    1104 Winchester Road, Lexington, KY 40505
    1/4
    Active

    $15

    5,318 SqFt

    1104 Winchester Road, Lexington, KY 40505

    Listed by Block + Lot Real Estate

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    1946 Bypass Road, Winchester, KY 40391
    1/22
    Active

    $10

    8.4 Acres Lot

    1946 Bypass Road, Winchester, KY 40391

    Listed by Keller Williams Commonwealth

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    204 Wigeon Court, Winchester, KY 40391
    1/6
    Active

    $49,500

    0.98 Acres

    204 Wigeon Court, Winchester, KY 40391

    Listed by RE/MAX Creative, Winchester

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    12569-B Ironworks Road, Winchester, KY 40391
    1/4
    Active

    $67,500

    1.92 Acres

    12569-B Ironworks Road, Winchester, KY 40391

    Listed by Coldwell Banker McMahan

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    150 Spencer Lane, Winchester, KY 40391
    1/3
    Active

    $70,000

    2.04 Acres

    150 Spencer Lane, Winchester, KY 40391

    Listed by Coldwell Banker McMahan

    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)
    2570 Bypass Road, Winchester, KY 40391
    1/22
    Active

    $1,300,000

    4,331 SqFt

    2570 Bypass Road, Winchester, KY 40391

    Listed by Block + Lot Real Estate

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    1045 Gay Evans Road, Winchester, KY 40391
    Pending

    $189,900

    10.73 Acres

    1045 Gay Evans Road, Winchester, KY 40391

    Listed by The Agency

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    12569 Ironworks Road Road, Winchester, KY 40391
    1/4
    Active

    $137,500

    3.94 Acres

    12569 Ironworks Road Road, Winchester, KY 40391

    Listed by Coldwell Banker McMahan

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    1311 Winchester Road, Lexington, KY 40509
    1/10
    Active

    $1,100,000

    1.01 Acres

    1311 Winchester Road, Lexington, KY 40509

    Listed by Keller Williams Bluegrass Realty

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    16 N Main Street, Winchester, KY 40391
    1/17
    Active

    $299,999

    2,310 SqFt

    16 N Main Street, Winchester, KY 40391

    Listed by Block + Lot Real Estate

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    6699 Boonesboro Road, Winchester, KY 40391
    1/2
    Active

    $195,000

    8.35 Acres

    6699 Boonesboro Road, Winchester, KY 40391

    Listed by RE/MAX Elite Lexington

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    495 Gawthrop Drive, Winchester, KY 40391
    1/4
    Active

    $7

    5,000 SqFt

    495 Gawthrop Drive, Winchester, KY 40391

    Listed by Block + Lot Real Estate

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    102 Augusta Drive, Winchester, KY 40391
    1/5
    Active

    $29,000

    0.46 Acres

    102 Augusta Drive, Winchester, KY 40391

    Listed by Dream Maker Realty, LLC

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
    650 Winchester Rd., Mt Sterling, KY 40353
    1/12
    Active

    $499,900

    1.77 Acres

    650 Winchester Rd., Mt Sterling, KY 40353

    Listed by United Real Estate Bluegrass

    Imagine MLS / Bluegrass Association of REALTORS (LBAR)
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        Home
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        About
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        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.

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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.