# 101 S Main, Winchester, KY 40391

> **TL;DR:** commercial, $1,750,000 ($85/sqft), 20,548 sqft. Est. $7,583/mo. Listed 934 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $1,750,000 |
| Price/sqft | $85 |
| Square Feet | 20,548 |
| Lot Size | 10,019 sqft (0.23 acres) |
| Stories | 3 |
| Property Type | Commercial (Office) |
| Status | For Sale |
| Days on Market | 934 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $7,583 |
| **Total** | **$7,583** |

## Property Highlights

- 0.23 acre lot
- 3 stories

## Description

### Agent Description
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.

## Location

- **Address:** 101 S Main, Winchester, KY 40391
- **County:** Clark
- **Neighborhood:** Downtown
- **Coordinates:** 37.991651, -84.177741
- **Google Maps:** https://www.google.com/maps?q=37.991651,-84.177741

## Listing Agent

- **Name:** Gregory Leveridge
- **Brokerage:** Block + Lot Homes
- **Phone:** 8594218959
- **Email:** greg@balrealestate.com

## Primary Photo

![101 S Main - Primary Photo](http://lh.rdcpix.com/53410f460e3eb99482b15ccd186dcd38l-f2053670839r.jpg)

*25 total photos available on [listing page](https://www.propertysimple.com/listing/101-s-main-winchester-ky-40391-23021742)*

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**MLS#:** 23021742 | **Updated:** 2026-06-17
**Source:** listhub

*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.*

[View on PropertySimple](https://www.propertysimple.com/listing/101-s-main-winchester-ky-40391-23021742)

---

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