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Winchester Opera House

101 S Main Street, Winchester, KY 40391

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Overview

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 Commission. 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.

Lease Spaces

NameFloorRateSFStatus
Second & Third Floors2 & 3$10,000 /Month15,796 SFavailable
First Floor1$4,500 /Month4,752 SFavailable

For Sale/Lease

Retail

Secondary Uses: Free Standing

Lease Rate
$4,500 - $10,000 Month
Available SF
4,752 - 15,796 SF
Total Available SF
20,548 SF
Sale Price
$1,750,000
Price Per SF
$85.17/SF
Building Size
20,548 SF
Acres
0.23 ac
Zoning
B-2
Lease Type
Plus Utilities
# of Buildings
1
Floors
2
Year Built
1873
Rentable SF
20,548
Nearest MSA
Lexington-Fayette
Tax ID Number
054-3218-001-00
Property Status
Existing
In Opportunity Zone
Yes
Nearest Interstate
I-64
County
Clark
Listed
04/23/2026
Updated
04/23/2026
Listing ID
21f88716
Parcel APN
054-3218-001-00