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101 S Main, Winchester, KY 40391

Downtown · Clark County

Key Facts

20,548Sq Ft
0.23Lot (acres)
3Stories

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.

Property Information

Property Type

Commercial Sale

Sub-Type

Office

Stories

3

Living Area

20,548 sq ft

Lot Size

0.23 acres

Zoning

Other

MLS® Listing#

23021742

Property Features

Construction

Brick

Utilities

Electricity AvailableNatural Gas AvailableSewer AvailableWater Available

Sewer

Public Sewer

Financial Details

Parcel Number

054-3218-001-00

Directions

Eastbound on Main St, property on Left

Affordability Calculator

$350,000

Estimated monthly payment

$9,314/mo

Principal $1,400,000 · Est. interest $1,953,125 over 30 yrs

Neighborhood Market Statistics

How this home compares to active listings in Winchester, KY

$333,898
Median Listing Price
54
Median Days on Market
1,988
Median Sq Ft
$173
Median Price / Sq Ft
119
Active Listings
  • This home’s price is 424% above the area median.
  • Its price per sq ft is 51% below the area median.

Market statistics compiled from active EXIT Realty® and MLS listings in Winchester, KY.

Location

  • 101 S Main, Winchester, KY 40391

Points of Interest in Winchester, KY

Showing the Winchester area map.

Nearby Schools

  • St Agatha Academy

    School · 0.2 mi away

  • Shearer Elementary School

    Elementary · 0.4 mi away

  • Fannie Bush Elementary School

    Elementary · 0.5 mi away

  • Hannah McClure Elementary School

    Elementary · 0.6 mi away

  • Central Elementary School

    Elementary · 1.1 mi away

  • Willis H. Justice Elementary School

    Elementary · 1.1 mi away

  • Victory Heights School

    School · 1.1 mi away

  • Conkwright Middle School

    School · 1.1 mi away

  • William G. Conkwright Elementary

    Elementary · 1.1 mi away

  • Robert D Campbell Pto

    Secondary · 1.2 mi away

  • Kentucky Tech Clark Co Center

    School · 1.2 mi away

  • Phoenix Academy

    School · 1.3 mi away

  • Calvary Christian Church

    School · 1.8 mi away

  • Flutterby Discovery Center

    School · 2.0 mi away

  • Clark County Public Schools

    School · 2.3 mi away

  • Clark County Christian School

    Elementary · 2.3 mi away

  • Henry E Baker Intermediate

    Secondary · 2.4 mi away

  • Clark Middle School

    School · 2.4 mi away

  • Clark County Area Technology Center

    Secondary · 2.4 mi away

  • Strode Station Elementary School

    Elementary · 2.5 mi away

Commute Calculator

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Nearby Homes

Similar Homes Nearby

Similar Home Values

Comparable nearby listings and their asking prices.

AddressPriceBedsBathsSq Ft
1200 Craig Crossing, Winchester, KY$1,349,000453,350
155 April Way, Winchester, KY$1,350,000
1015 Old Stone Church Road, Winchester, KY$1,500,000
599 BLT Way, Winchester, KY$1,599,90020,252
4578 Combs Ferry Road, Winchester, KY$1,650,000321,860
3166 Colby Road, Winchester, KY$1,695,000334,518

Moving Cost Estimate

EXIT Agents in Winchester

Imagine MLS logo

Listing Courtesy: Block + Lot Homes - 8593090099

The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) Program of Bluegrass REALTORS®. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by IDX brokerage firms other than EXIT Realty, are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX brokers. Information deemed reliable but not guaranteed. Copyright ©2026 Bluegrass REALTORS®. All Rights Reserved.

Last Updated: 2023-11-10

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of one or more Multiple Listing Services (MLS). Listing information is deemed reliable but is not guaranteed accurate. Copyright © EXIT Realty® and respective MLS providers.

Data provided by Imagine MLS (Bluegrass REALTORS®). MLS® Listing#23021742. © 2026EXIT Realty®. All rights reserved.