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Historic Opera House Venue
For Sale
$1,750,000

101 S Main, Winchester, KY 40391

COMMERCIAL - Winchester, KY

Property Size20,548 SF
Lot Size0.23 Acres
Price / SF$85.17
Days on Market1006

Property Features for 101 S Main

General Information

Property type Commercial Sale
Property subtype Office
Zoning description B-2
Subdivision Downtown
Directions Eastbound on Main St, property on Left
Standard status Active
APN 054-3218-001-00
Size 20,548 SF
Lot size 0.23 Acres

Utilities

Utilities Water Available
Sewer type Public Sewer

Amenities

commercial kitchens
hardwood floors
large windows
exposed brick
functioning fireplaces

Building Details

Floors in Building 3
Building materials Brick
Listing Agency: Block + Lot Homes
Listed By: Gregory Leveridge · License #215416
Added: Nov 10, 2023 Changed: Aug 4 Last Checked: Aug 12 at 5:06AM
MLS# 23021742

Copyright © 2026 ImagineMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Investment Insights

Based on property information with market context.

Located at 101 S Main in Winchester, Kentucky, this 20,548-square-foot historic opera house occupies a 0.23-acre parcel and has been extensively restored for multiple commercial functions. The interior includes gallery, restaurant, wedding and reception, ballroom, and office areas, along with multiple commercial kitchens and an interior elevator. Hardwood floors, large windows, exposed brick, and functioning fireplaces retain the building’s historic character. The property is constructed with brick and includes public sewer and water availability.

The building is situated in downtown Winchester and falls within an Opportunity Zone. Its renovation received the Clyde Carpenter Adaptive Reuse Award from the Bluegrass Trust Historic Preservation Commission. The real estate offering does not include the restaurant business. Existing layouts can support continued use of the current commercial spaces or a different combination of the established functions.

Key Highlights

  • 20,548‑square‑foot historic opera house on 0.23 acres
  • Multiple commercial kitchens, interior elevator, and flexible event, dining, gallery, and office areas
  • Restored interior with hardwood floors, large windows, exposed brick, and functioning fireplaces

Property Analytics

Current Use

Peoples Exchange Insurance Atm Peoples Exchange Bank Bank

Suggested Use

Top Pick Dental Office Real Estate Agency HVAC Service Skin Care Clinic Spa & Massage Center Gym & Fitness Center

Score = modeled unmet demand for each use within ~1 mi (higher = bigger opportunity). Zoning and permitted uses should be independently verified with local authorities.

Location Intelligence

Trade Area within ½ mile

651
Businesses Nearby

Demographics for 40391, KY

36,461
Population
16,125
Households
2.3
Avg Household Size
41
Median Age
22%
College-Educated
90%
High-School Grad
237.3 sq mi
ZIP Area
154
Density / Sq Mi
$67,910
Median Household Income
$40,323
Median Earnings
$884
Median Rent
$197,200
Median Home Value

Market

Vacancy Rate% for Office in South region

14.4% 2019
16.4% 2020
17.3% 2021
18% 2022
18.6% 2023
20.3% 2024
20.2% 2025
Rey
Questions? Ask Rey
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Frequently Asked Questions

What type of property is this?
Theater & concert hall - Restored brick venue combines event, dining, gallery, and office areas in a flexible downtown commercial setting.
Where is this theater & concert hall located?
The property is located at 101 S Main Winchester, KY.
What is the asking price?
The asking price for this property is $1,750,000.
What are key features of this property?
This property features: 20,548‑square‑foot historic opera house on 0.23 acres; Multiple commercial kitchens, interior elevator, and flexible event, dining, gallery, and office areas; Restored interior with hardwood floors, large windows, exposed brick, and functioning fireplaces
More about this property
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