100 N LOUDOUN Street, Winchester, VA 22601

Building Details

Year built

1900

Building materials

Brick

Listing agent Gillian Joy Greenfield License #0225064152 Show Phone

Listing office Coldwell Banker Premier h***@premiermove.com 14 E Piccadilly Street, Winchester, VA Show Phone

Listing date Sep 29, 2025

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MLS# VAWI2009162

Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

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Overview

This restaurant opportunity is set in a gorgeous historical building that combines original brick and hardwood floors with modern upgrades. The space includes a huge bar seating area and a large dining room with room for live music, along with storage and a kitchen. The kitchen is described as having no hood currently, with the possibility that a hood may be installed. A major draw is the massive windows and a huge outdoor dining area suited for seasonal service and outdoor events. Additional space may be expanded by about 2,100 SF to reach up to 5,600 SF of dining and kitchen area, and there is also the option to add approximately 1,800 SF for a basement “speakeasy.”

Located in the heart of downtown Winchester in the Old Town Walking Mall, the property is positioned for walk-in traffic from a central retail and dining environment. The listing notes it as an outstanding opportunity for experienced restaurant operators.

The layout supports full-service dining with programming flexibility, including bar-forward service and live entertainment. Operators seeking a character-rich, upgraded building with meaningful outdoor capacity, plus potential for expansion or a basement concept, should find the configuration practical for a range of restaurant formats.

Suggested Use

Law Firm Restaurant Real Estate Agency Spa & Massage Center Dental Office Hair Salon Nail Salon Building Supply Gym & Fitness Center Daycare Center

Zoning and permitted uses should be independently verified with local authorities.

Similar Places Nearby

• Laura's Lemons — TBD, Winchester, VA 22601

Location Insight

• Map
• Local Demand

City

Winchester

County

Frederick

State

Virginia

Longitude

-78.1652

Latitude

39.1847

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FAQs

What type of property is this?

Restaurant - Historic downtown restaurant space with a large bar, dining room, live-music setup, and extensive outdoor dining area.

Where is this restaurant located?

The property is located at 100 N LOUDOUN Street Winchester, VA.

What is the lease rate?

The lease rate is $17 SF/Yr.

What are key features of this property?

This property features: Historical brick building with original brick and hardwood floors throughout; Restaurant space totals 3,500 SF plus approximately 4,000 SF outdoor dining area; Includes huge bar seating area, large dining area, room for live music, storage space, and a kitchen (no hood currently)