# 39 S Main Street, Winchester, KY 40391

> **TL;DR:** commercial, $429,000 ($121/sqft), 3,538 sqft. Est. $1,859/mo. Listed 275 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $429,000 |
| Price/sqft | $121 |
| Square Feet | 3,538 |
| Lot Size | 436 sqft (0.01 acres) |
| Property Type | Commercial (Other) |
| Status | For Sale |
| Days on Market | 275 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $1,859 |
| **Total** | **$1,859** |

## Property Highlights

- 0.01 acre lot
- 10 parking spaces

## Description

### Agent Description
Wonderfully renovated historic building across from the Court House in Downtown Winchester! The well appointed restaurant space has a full hood system, concrete bar, beautiful hardwood floors, tin ceiling and parking in the back. The apartment is the perfect size and has a private deck! Great opportunity to live upstairs and have your restaurant downstairs! Downtown Winchester is the place to be. Close enough to Lexington but far enough away to be a destination. Numerous apartments are coming soon, great restaurants and lots of tourists make this a great place to start a business. Property Highlights: -Full hood system, concrete bar, hardwood floors, tin ceiling, and a full commercial kitchen -Building retains historic charm with a significant portion dating back to the original construction, coupled with a recent renovation to maximize functionality -Conducive to live/work layout and/or short-term rentals -Downtown Winchester, KY is booming - everyone wants to be Downtown including shops, restaurants, and new apartment living options

## Location

- **Address:** 39 S Main Street, Winchester, KY 40391
- **County:** Clark
- **Neighborhood:** Commercial
- **Coordinates:** 37.992525, -84.176882
- **Google Maps:** https://www.google.com/maps?q=37.992525,-84.176882

## Listing Agent

- **Name:** Lara Thornbury
- **Brokerage:** Block + Lot Real Estate
- **Phone:** 8597712552
- **Email:** lara@balrealestate.com

## Primary Photo

![39 S Main Street - Primary Photo](http://lh.rdcpix.com/a0136c698fed141b5a70daf9f3169f98l-f1445480221r.jpg)

*23 total photos available on [listing page](https://www.propertysimple.com/listing/39-s-main-street-winchester-ky-40391-25014867)*

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**MLS#:** 25014867 | **Updated:** 2026-04-24
**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/39-s-main-street-winchester-ky-40391-25014867)

---

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