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    27-29 S Main Street, Winchester, KY 40391
    $314,900
    3,920sqft
    0.09acres
    Commercial Sale

    27-29 S Main Street, Winchester, KY 40391

    Listing by: Block + Lot Real Estate
    1 - 1 of 1 results
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    Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
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    27-29 S Main Street, Winchester, KY 40391
    27-29 S Main Street, Winchester, KY 40391
    27-29 S Main Street, Winchester, KY 40391
    27-29 S Main Street, Winchester, KY 40391
    27-29 S Main Street, Winchester, KY 40391
    27-29 S Main Street, Winchester, KY 40391
    27-29 S Main Street, Winchester, KY 40391
    27-29 S Main Street, Winchester, KY 40391
    27-29 S Main Street, Winchester, KY 40391
    27-29 S Main Street, Winchester, KY 40391
    27-29 S Main Street, Winchester, KY 40391
    27-29 S Main Street, Winchester, KY 40391
    27-29 S Main Street, Winchester, KY 40391
    27-29 S Main Street, Winchester, KY 40391
    $314,900
    3,920sqft
    0.09acres

    27-29 S Main Street, Winchester, KY 40391

    Commercial Sale by Lara ThornburyBlock + Lot Real Estate.

    Data checked 18 mins ago. Listing last updated 28 days ago.
    1. Overview
    2. Details
    3. More 

    Located across from the Court House on the high side of Main Street makes this beautiful building an ideal place to start your new business. The downstairs has been completely renovated with a whole new storefront, new HVAC, brick walls exposed, and new flooring laid. The demo work is complete upstairs and a new back deck has been added, walls are up, plaster work is completed and the new back windows are in! The apartment boasts a beautiful staircase, hardwood floors, and abundant natural light. Perfect building to live upstairs and bring your business downstairs. There is a large back parking lot with alley access and this building is in the Opportunity Zone. Winchester First has numerous grants for renovating properties and starting new businesses. Check out winchesterfirst.org. Owner is the agent. Property Highlights: - Located across from the Court House - Live upstairs and work downstairs - Parking - Opportunity Zone From South Main Street, building is directly across from the Court House. http://winchesterfirst.org - Grant Opportunities

    Details
      Property type
    Commercial Sale
      Year built
    1880
      Heating
    -
      Cooling
      Garage
    No
      Parking spots
    -
    24016294
    MLS ID
    Active
    Status
    10-13-2025
    On market date
      Flooring
      View
    Exterior features
    Lot features
    Monthly taxes
    -
    Yearly taxes
    -
    Schools
    -
    Open Houses
    In-Person
    No upcoming in-person open houses
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    No upcoming virtual open houses
    Contact Agent
    Lara Thornbury
    Lara Thornbury
    REALTOR® Salesperson, Block + Lot Real Estate
     
     
    Building Info
    Address
    27-29 S Main Street, Winchester, KY 40391
    Number of Floors
    2
    Gross area
    3,132 sqft
    Frontage
    27 ft
    Depth
    211 ft
    Location
    From South Main Street, building is directly across from the Court House
    For Sale Nearby
    273 Shoppers Drive, Winchester, KY 40391
    $1,650,000
    21,780sqft
    acres
    Commercial Sale

    273 Shoppers Drive, Winchester, KY 40391

    Listing by: Steven D Adams Real Estate Services, LLC
    250 Shoppers Drive, Winchester, KY 40391
    $1,500,000
    293,028.12sqft
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    Commercial Sale

    250 Shoppers Drive, Winchester, KY 40391

    Listing by: Steven D Adams Real Estate Services, LLC
    1496 Martin Luther King Jr Drive, Winchester, KY 40391
    $700,000
    135,907.2sqft
    acres
    Commercial Sale

    1496 Martin Luther King Jr Drive, Winchester, KY 40391

    Listing by: Steven D Adams Real Estate Services, LLC
    440 Shoppers Drive, Winchester, KY 40391
    $1,110,000
    194,016.24sqft
    acres
    Commercial Sale

    440 Shoppers Drive, Winchester, KY 40391

    Listing by: Steven D Adams Real Estate Services, LLC
    1050 Early Drive, Winchester, KY 40391
    $595,000
    135,471.6sqft
    acres
    Commercial Sale

    1050 Early Drive, Winchester, KY 40391

    Listing by: The Gibson Company
    101 Jefferson Street, Winchester, KY 40391
    $1,200,000
    168,577.2sqft
    acres
    Commercial Sale

    101 Jefferson Street, Winchester, KY 40391

    Listing by: Dream Maker Realty, LLC
    838 Bypass Road, Winchester, KY 40391
    $614,900
    13,504sqft
    acres
    Commercial Sale

    838 Bypass Road, Winchester, KY 40391

    Listing by: Lifstyl Real Estate
    152 W Broadway Street, Winchester, KY 40391
    $199,900
    5,663sqft
    acres
    Commercial Sale

    152 W Broadway Street, Winchester, KY 40391

    Listing by: Dream Maker Realty, LLC
    126 Shoppers Drive, Winchester, KY 40391
    $805,000
    34,412sqft
    acres
    Commercial Sale

    126 Shoppers Drive, Winchester, KY 40391

    Listing by: The Gibson Company
    Recently Sold
    Closed Oct 28
    380 Noble King Court, Winchester, KY 40391
    $185,000
    0.03sqft
    acres
    Commercial Sale

    380 Noble King Court, Winchester, KY 40391

    Listing by: Dream Maker Realty, LLC
    Closed Sep 30
    115 Hud Road, Winchester, KY 40391
    $1,350,000
    85,378sqft
    acres
    Commercial Sale

    115 Hud Road, Winchester, KY 40391

    Listing by: Block + Lot Real Estate
    Closed Jul 31
    2560 Bypass Road, Winchester, KY 40391
    $1,275,000
    44,867sqft
    acres
    Commercial Sale

    2560 Bypass Road, Winchester, KY 40391

    Listing by: Block + Lot Real Estate
    Closed May 6
    117 N Main Street, Winchester, KY 40391
    $365,000
    8,712sqft
    acres
    Commercial Sale

    117 N Main Street, Winchester, KY 40391

    Listing by: Block + Lot Real Estate
    Closed May 2
    31 S Main Street, Winchester, KY 40391
    $170,000
    6,098sqft
    acres
    Commercial Sale

    31 S Main Street, Winchester, KY 40391

    Listing by: Block + Lot Real Estate
    Closed Apr 8
    121 E Lexington Avenue, Winchester, KY 40391
    $165,000
    13,068sqft
    acres
    Commercial Sale

    121 E Lexington Avenue, Winchester, KY 40391

    Listing by: Freedom Realty & Property Management
    Closed Apr 1
    1805 Fortune Drive, Winchester, KY 40391
    $4,800,000
    252,212sqft
    acres
    Commercial Sale

    1805 Fortune Drive, Winchester, KY 40391

    Listing by: Block + Lot Real Estate
    Closed Jan 30
    1318-1320 Fulton Road, Winchester, KY 40391
    $340,000
    31,363sqft
    acres
    Commercial Sale

    1318-1320 Fulton Road, Winchester, KY 40391

    Listing by: Block + Lot Real Estate
    Closed Nov 4
    126 Shoppers Drive, Winchester, KY 40391
    $490,000
    34,412sqft
    acres
    Commercial Sale

    126 Shoppers Drive, Winchester, KY 40391

    Listing by: The Gibson Company
    Closed Sep 27
    410 W Lexington Avenue, Winchester, KY 40391
    $335,000
    22,651sqft
    acres
    Commercial Sale

    410 W Lexington Avenue, Winchester, KY 40391

    Listing by: Thwaites Realtors LLC
    27-29 S Main Street, Winchester, KY 40391, is a 0.09 acres, 3920 sqft. Mixed Use built in 1880. This property is currently available for sale and was listed on Imagine Your Home on 10-13-2025. The MLS# for this Mixed Use is MLS# 24016294.
    Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
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