101 S Main, Winchester, KY 40391
$1,750,000
Property Type:
Commercial Sale
Square Footage:
20,548
Lot Size (sq. ft.):
10,019
Status:
Active
Current Price:
$1,750,000
List Date:
4/23/2026
Last Modified:
4/23/2026
Listing Details MLS# 23021742
Listing Information
- Comp Sale YN
- No
- Property Sub Type
- Office
Status Change Information
- Status Change Timestamp
- 2026-04-23
- Back on Market Date
- 2026-04-23
Address
- County
- Clark
- Street Number
- 101
- Street Direction Prefix
- S
- Street Name
- Main
- State
- KY
- Zip Code
- 40391
- Parcel Number
- 054-3218-001-00
Contract
- Original List Price
- 1750000
- Start Showing Date
- 2023-11-10
- Listing Contract Date
- 2023-11-10
- Listing Agreement
- Exclusive Right To Sell
- Occupant Type
- Vacant
- Office Exclusive YN
- No
- List Price/SqFt
- 85.17
Tax Legal
- MLS Area Major
- 007 - Clark County
- Subdivision Name
- Downtown
Interior
- Living Area Units
- Square Feet
- Building Area Total
- 20548
- Building Area Source
- Public Records
- Building Area Units
- Square Feet
More Information
Building
- Year Built
- 9999
- Stories Total
- 3
- Accessibility Features YN
- Yes
Lot
- Lot Size Acres
- 0.23
- Lot Size Square Feet
- 10019
Remarks
- Public Remarks
- 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.
Tax & Legal
- Tax Rate
- 1.26
- Zoning
- Other
- Zoning Description
- B-2
- Directions
- Eastbound on Main St, property on Left
Association/Community
- Number Of Buildings
- 1
Utilities
- Electricity Available
- Yes
- Natural Gas Available
- Yes
- Sewer Available
- Yes
- Water Available
- Yes
Construction Materials
- Brick
- Yes
Possession
- Close Of Escrow
- Yes
Sewer
- Public Sewer
- Yes
Building Features
- Wood Flooring
- Yes
Business Type
- Commercial
- Yes
- Professional/Office
- Yes
- Restaurant
- Yes
- Retail
- Yes
Existing Lease Type
- None
- Yes
Sale Includes
- Building(s)
- Yes
- Land
- Yes
Showing Requirements
- Call Listing Agent
- Yes
Property Features
Utilities:
Electricity Available; Natural Gas Available; Sewer Available; Water Available; Electricity Available; Natural Gas Available; Sewer Available; Water Available
Building Features:
Wood Flooring
Business Type:
Commercial; Professional/Office; Restaurant; Retail
Construction Materials:
Brick
Existing Lease Type:
None
Possession:
Close Of Escrow
Sale Includes:
Building(s); Land
Sewer:
Public Sewer
Showing Requirements:
Call Listing Agent
Listing Office:
Block + Lot Homes
Last Updated: April - 23 - 2026
Information deemed reliable but not guaranteed.