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      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      $1,750,000
      10,019sqft
      0.23acres
      Commercial Sale

      101 S Main, Winchester, KY 40391

      Listing by: Block + Lot Real Estate
      1 - 1 of 1 results
      © 2026 Imagine MLS
      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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      Imagine Your Home
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      101 S Main, Winchester, KY 40391
      $1,750,000
      10,019sqft
      0.23acres

      101 S Main, Winchester, KY 40391

      Commercial Sale by Gregory LeveridgeBlock + Lot Real Estate.

      Data checked -. Listing last updated 10 days ago.
      1. Overview
      2. Details
      3. More 

      101 S. Main Street is a fully-restored historic Opera House in the heart of Downtown Winchester. Now functioning in a multiple use capacity, including gallery space, 7-years-running successful restaurant space, wedding event and reception space, and office space. No detail was overlooked in this extensive renovation, now inclusive of multiple commercial kitchens, interior elevator, gracious entertainment spaces, and an abundance of old-world charm through hardwood floors, large windows, exposed brick, and functioning fireplaces. In fact, the Opera House renovations earned the Clyde Carpenter Adaptive Reuse Award from the Bluegrass Trust Historic Preservation Comm. This offering is extremely flexible in that a new owner can step in and operate the same uses already in place, including Lease Back potential from Loma's which is owner occupied, or use the flexible layouts for its own preferences. It is also in the Opportunity Zone, and Downtown Winchester KY offers numerous grants for both renovations and business development should a buyer wish to participate. *Business purchase is not included in the real estate offering. Property Highlights: -Home of the successful and delicious Loma's at the Opera House restaurant and bar, and The Winchester Opera House Ballroom -Ideally located in the heart of Downtown Winchester -The property benefits from the City of Winchester's investment in neighboring High Side Improvement Project with included $5.5 million invested in new angled parking, new sidewalks and added ramps, making the downtown area more accessible as well as 13 new high-end apartments with 10 more in development.

      Details
        Property type
      Commercial Sale
        Year built
      9999
        Heating
        Cooling
        Garage
      No
        Parking spots
      -
      23021742
      MLS ID
      Active
      Status
      04-23-2026
      On market date
        View
      Exterior features
      Lot features
      Flooring
      Monthly taxes
      -
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      No upcoming in-person open houses
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      No upcoming virtual open houses
      Contact Agent
      Listing By:
      Gregory Leveridge
      Gregory Leveridge
      Lara Thornbury
      Lara Thornbury
      Gregory Leveridge
      Gregory Leveridge
      Designated REALTOR® Participant, Block + Lot Real Estate
       
       
      Lara Thornbury
      Lara Thornbury
      REALTOR® Salesperson, Block + Lot Real Estate
       
       
      Location
      Eastbound on Main St, property on Left
      For Sale Nearby
      No nearby homes are For Sale Nearby.
      Recently Sold
      No nearby homes have been Recently Sold.
      101 S Main, Winchester, KY 40391, is a 0.23 acres, 10019 sqft. Office built in 9999. This property is currently available for sale and was listed on Imagine Your Home on 4-23-2026. The MLS# for this Office is MLS# 23021742.
      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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