Downtown Retail and Live-Work Building

18 N Main Street, Winchester, KY 40391

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New

Pending

$199,900

COMMERCIAL - Winchester, KY

Property size:

4,300 SF

Lot size:

0.12 Acres

HighLights

Brick building with rubber roof and public sewer service
Main level renovation includes new roof, new storefront, and new electrical, plumbing, and HVAC
Downstairs features retail space with tile, original hardwood floors, exposed brick, and shiplap walls plus tin ceilings
Downstairs includes 1 full bath, 1 half bath, 6 dressing rooms, storage room, and a back door with access to the back parking lot
Upstairs has a separate entrance with space that can be updated for live/work or additional business use
Location downtown Winchester—across from new luxury apartments and Leeds Theater, next to established businesses and restaurants

We can help!

Contact an agent

Lucy Martin Jenkins

Pending

$199,900

COMMERCIAL - Winchester, KY

Property size:

4,300 SF

Lot size:

0.12 Acres

Added:: Jun 22, 2026
Days on Market:: 6
Last Refresh:: Jun 27 at 5:06 am

Property Features for 18 N Main Street

General Information

Property type: Commercial Sale
Property subtype: Other
Parking: 7
Basement: Crawl Space
Standard status: Pending
APN: 054-3209-014-00
Size: 4,300 SF
Lot size: 0.12 Acres

Utilities

Sewer type: Public Sewer
Cooling system: Electric

Building Details

Floors in Building: 3
Building materials: Brick
Roof type: Rubber

We can help!

Contact an agent

Lucy Martin Jenkins

Listing agent Lucy Martin Jenkins

Listing office United Real Estate Bluegrass 424 Lewis Hargett Cir Ste 120, Lexington, KY

Listing date Jun 22, 2026

MLS# 26014568

HighLights

Brick building with rubber roof and public sewer service
Main level renovation includes new roof, new storefront, and new electrical, plumbing, and HVAC
Downstairs features retail space with tile, original hardwood floors, exposed brick, and shiplap walls plus tin ceilings
Downstairs includes 1 full bath, 1 half bath, 6 dressing rooms, storage room, and a back door with access to the back parking lot
Upstairs has a separate entrance with space that can be updated for live/work or additional business use
Location downtown Winchester—across from new luxury apartments and Leeds Theater, next to established businesses and restaurants

Overview

This downtown building was substantially renovated by the current owners, including a new roof, new storefront, and updated electrical, plumbing, and HVAC on the main level. Inside, the main level features tile, original hardwood floors, exposed brick, shiplap walls, and detailed tin ceilings. The downstairs retail space includes one full bathroom, one half bathroom, six dressing rooms, a storage room, and a back door with access to a back parking lot. The layout also provides upstairs access.

The property is located on N Main Street in downtown Winchester, Kentucky. Public remarks note it sits across from new luxury apartments and Leeds Theater, and next to established businesses and restaurants.

With retail space on the main level and an upstairs area that can be updated for live-work or an additional business, the building can support multiple operating scenarios. The presence of dressing rooms, bathrooms, and dedicated back access may be beneficial for tenant concepts that require flexible customer flow and back-of-house support.

Property Profile Location Intelligence

Current Use by Public Records

Betsey's Boutique Shop Clothing Store

Suggested Use

Location Insight

Map
Local Demand

City: Winchester
County: Clark
State: Kentucky
Longitude: -84.177075
Latitude: 37.994247

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For sale
Retail space
KY
Winchester
40391
18 N Main Street

What type of property is this?

Retail space - Renovated downtown building with updated main-level systems, storefront, and interior space adaptable for live-work or additional business.

Where is this retail space located?

The property is located at 18 N Main Street Winchester, KY.

What is the asking price?

The asking price for this property is $199,900.

What are key features of this property?

This property features: Brick building with rubber roof and public sewer service; Main level renovation includes new roof, new storefront, and new electrical, plumbing, and HVAC; Downstairs features retail space with tile, original hardwood floors, exposed brick, and shiplap walls plus tin ceilings

18 N Main Street, Winchester, KY 40391

COMMERCIAL - Winchester, KY

Property Features for 18 N Main Street

General Information

Utilities

Building Details

We can help!

HighLights

Overview

Current Use by Public Records

Suggested Use

Location Insight

Nearby Similar for Sale

Turnkey Industrial Warehouse with Racking

Winchester Mixed-Use Commercial Opportunity

Two-Story Medical Office and Apartments

Winchester Industrial Property For Sale

Fully Leased Fourplex

Brick Mixed-Use Triplex

Single-Family Residence with 10-Foot Ceilings

Profitable Car Wash and Oil Change

Mixed-Use Property with Residential Income

B-3 Zoned Storage and Flex Building

Downtown Triplex Income Property

Updated Quadplex in Downtown Winchester

FAQs