16 N Main Street, Winchester, KY 40391

$299,999
Property Type: Commercial Sale Square Footage: 2,310 Lot Size (sq. ft.): 7,841 Status: Active
Current Price: $299,999 List Date: 8/03/2026 Last Modified: 9/02/2026

Overview

Description

An excellent opportunity to own a fully leased, income-producing property in the heart of Downtown Winchester, Kentucky. This beautifully renovated 2,310 SF retail storefront is being offered at a 10% cap rate, making it an attractive turnkey investment from day one. The building may be old, but nearly everything inside is new! Recent improvements include a new roof, four new skylights, exposed beams, new hardwood flooring throughout, updated electrical and plumbing, and HVAC. The space is plumbed for four bathrooms and also includes a laundry room and private back office with a window overlooking the main retail area. This property boasts a large rear parking lot—one of the largest in Downtown Winchester—providing convenient parking for tenants, customers, and employees. The location is surrounded by continued downtown growth. Seven new high-end apartments across the street, while the same block is already home to five restaurants, numerous shops, and the Leeds Center for the ...

Listing Details MLS# 25001584

Listing Information

Comp Sale YN
No
Property Sub Type
Retail

Status Change Information

Price Change Timestamp
2025-10-29T15:11:25Z
Status Change Timestamp
2026-08-03
Back on Market Date
2026-08-03

Address

County
Clark
Street Number
16
Street Direction Prefix
N
Street Name
Main
Street Suffix
Street
State
KY
Zip Code
40391
Parcel Number
054-3209-015-00

Contract

Original List Price
324900
Start Showing Date
2025-01-30
Listing Contract Date
2025-01-30
Listing Agreement
Exclusive Right To Sell
Occupant Type
Vacant
Office Exclusive YN
No
List Price/SqFt
129.87

Tax Legal

MLS Area Major
007 - Clark County
Subdivision Name
Commercial

Interior

Living Area
2310
Living Area Units
Square Feet
Building Area Total
2310
Building Area Source
Public Records
Building Area Units
Square Feet

More Information

Building

Year Built
9999
Stories Total
Yes
Accessibility Features YN
Yes

Lot

Lot Size Acres
0.18
Lot Size Square Feet
7841

Remarks

Public Remarks
An excellent opportunity to own a fully leased, income-producing property in the heart of Downtown Winchester, Kentucky. This beautifully renovated 2,310 SF retail storefront is being offered at a 10% cap rate, making it an attractive turnkey investment from day one. The building may be old, but nearly everything inside is new! Recent improvements include a new roof, four new skylights, exposed beams, new hardwood flooring throughout, updated electrical and plumbing, and HVAC. The space is plumbed for four bathrooms and also includes a laundry room and private back office with a window overlooking the main retail area. This property boasts a large rear parking lot—one of the largest in Downtown Winchester—providing convenient parking for tenants, customers, and employees. The location is surrounded by continued downtown growth. Seven new high-end apartments across the street, while the same block is already home to five restaurants, numerous shops, and the Leeds Center for the Arts. Property Highlights: -Recently renovated with a new roof, 4 new skylights, exposed beams, new hardwood floors, new plumbing and new electrical. -The property is located directly across from a brand-new apartment building and is surrounded by retail and restaurants. -The property boasts the largest back parking lot in the downtown area, a bonus for staff and customer accessibility. -Downtown Winchester, KY is booming - everyone wants to be Downtown, introducing shops, restaurants, and new apartment living options. Winchester, KY is conveniently situated just 18 miles east of Lexington and, with proximity to I-64, provides quick access to the larger city's amenities. Downtown Winchester is home to a variety of beloved local establishments, including the historic Leeds Center for the Arts, La Trattoria, The Hall Coffee & Social Club, and several small shops. Over 30 new, high-end apartments are coming to Downtown Winchester - residents and tourists want to be Downtown!

Building and Property Details

Retail SqFt
2310

Property Features

Building Features: Other Flooring Type; Wood Flooring Business Type: Commercial; Retail Construction Materials: Brick; Glass Existing Lease Type: None Parking Features: On Site; Paved Possession: Close Of Escrow Sale Includes: Building(s); Land Special Listing Conditions: Standard Showing Requirements: Call Listing Agent
Listing Office: Block + Lot Homes
Last Updated: September - 02 - 2026
Information deemed reliable but not guaranteed.