# 16 N Main Street, Winchester, KY 40391 > **TL;DR:** commercial, $299,999 ($130/sqft), 2,310 sqft. Est. $1,604/mo. Listed 642 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $299,999 | | Price/sqft | $130 | | Square Feet | 2,310 | | Lot Size | 7,841 sqft (0.18 acres) | | Stories | 1 | | Property Type | Commercial (Retail) | | Status | Active | | Days on Market | 642 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $1,517 | | Estimated Insurance | $87 | | **Total** | **$1,604** | ## Property Highlights - 0.18 acre lot ## Description ### Agent 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 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! ## Location - **Address:** 16 N Main Street, Winchester, KY 40391 - **County:** Clark - **Neighborhood:** Commercial - **Coordinates:** 37.9941, -84.176899 - **Google Maps:** https://www.google.com/maps?q=37.9941,-84.176899 ## Listing Agent - **Name:** Lara Thornbury - **Brokerage:** Block + Lot Real Estate - **Broker Phone:** 3090099 ## Photos ![16 N Main Street - Photo 1](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f2680668795r.jpg) ![16 N Main Street - Photo 2](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f3659566581r.jpg) ![16 N Main Street - Photo 3](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f134600625r.jpg) ![16 N Main Street - Photo 4](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f3311017648r.jpg) ![16 N Main Street - Photo 5](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f4194126479r.jpg) ![16 N Main Street - Photo 6](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f316157479r.jpg) ![16 N Main Street - Photo 7](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f2760388054r.jpg) ![16 N Main Street - Photo 8](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f2367446031r.jpg) ![16 N Main Street - Photo 9](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f3467891279r.jpg) ![16 N Main Street - Photo 10](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f1548908303r.jpg) ![16 N Main Street - Photo 11](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f892023618r.jpg) ![16 N Main Street - Photo 12](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f3005326102r.jpg) ![16 N Main Street - Photo 13](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f1293438968r.jpg) ![16 N Main Street - Photo 14](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f999827372r.jpg) ![16 N Main Street - Photo 15](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f3892872070r.jpg) ![16 N Main Street - Photo 16](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f916652788r.jpg) ![16 N Main Street - Photo 17](http://lh.rdcpix.com/0e583d320d791c7cbf256658b82b204al-f580387810r.jpg) --- **MLS#:** 25001584 | **Updated:** 2026-10-20 **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://staging.propertysimple.ai/listing/16-n-main-street-winchester-ky-40391-ddc7fb6e8304433989a92a935da94c46) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/16-n-main-street-winchester-ky-40391-ddc7fb6e8304433989a92a935da94c46#listing", "url": "https://staging.propertysimple.ai/listing/16-n-main-street-winchester-ky-40391-ddc7fb6e8304433989a92a935da94c46", "name": "16 N Main Street, Winchester, KY 40391", "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. 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