$1,750,000
101 S Main, Winchester, KY 40391
- 0.23
- acres
- Office
- Property type
- 0.23 acres
- Lot size
Listing 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.
Listed by Block + Lot Homes · greg@balrealestate.com
MLS #23021742 · Listing provided by![]()
Shelby & Drake JohnsonFive Pillars Team · eXp Realty
Home Details
- Property type
- Office
- Lot size
- 0.23-acre lot
Interior
- 0 bathrooms
Property
- Office
- 0.23-acre lot
Construction
- Not reported
Services Availability
- Internet
- Not reported
- Utilities
- Not reported
- Parking
- Not reported
Property & Price History
| Date | Event | Price |
|---|---|---|
| Apr 23, 2026 | Listed for sale | $1,750,000 |
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Property Documents
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Estimate Your Monthly PaymentMonthly payment
Estimated monthlyEst. payment
$11,150/mo
30-year fixed · 6.75% assumed rate
- Principal & interest
- $9,080
- Taxes
- $1,560
- Other costs
- $510
- $1,750,000
- Home price
- 20% · $350,000
- Down payment
- 6.75%
- Interest rate
- 30 years
- Loan term
Payment Breakdown
- Principal & interest
- $9,080
- Estimated property taxes
- $1,560
- Home insurance
- $510
- HOA
- Not provided
- Utilities
- Not included
Estimate only. Utilities not included. HOA not provided.Illustrative estimate, not a loan offer. Taxes (1.07%/year) and insurance (0.35%/year) use assumptions; actual costs and available rates vary. HOA is not included because its monthly amount is unavailable.
Adjust Payment Details
Payment Breakdown
- Principal & interest
- $9,080
- Estimated property taxes
- $1,560
- Home insurance
- $510
- HOA
- Not provided
- Utilities
- Not included
Illustrative estimate, not a loan offer. Taxes (1.07%/year) and insurance (0.35%/year) use assumptions; actual costs and available rates vary. HOA is not included because its monthly amount is unavailable.
Travel Times and Accessibility
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- Walk Score
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- Bike Score
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Assigned Schools
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Shelby & Drake JohnsonFive Pillars Team · eXp Realty