Save
Ask
Tour
Hide
Share
$747,000
14 Days On Site

14-16 S LOUDOUN STREET
WINCHESTER, VA 22601

For Sale|Retail|Active
0
Beds
0
Total Baths
9,276
SqFt
$81
/SqFt
1900
Built
County:
WINCHESTER CITY
Listing courtesy of MarketPlace REALTY
Call Now: 540-227-4416
Is this the listing for you? We can help make it yours.
540-227-4416
14-16 S LOUDOUN STREET14-16 S LOUDOUN STREET14-16 S LOUDOUN STREET14-16 S LOUDOUN STREET
Save
Ask
Tour
Hide
Share

Mortgage Calculator

Monthly Payment (Est.)

$3,408
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

Rare opportunity to own a historic landmark in the heart of Old Town Winchester’s iconic Walking Mall. This impressive three-story commercial building offers approximately 9,276 square feet and features two retail storefronts in one of the Shenandoah Valley’s most sought-after downtown locations. Both retail spaces are currently leased, providing immediate and reliable rental income for investors. With established tenants already in place, this property presents an excellent opportunity to acquire a performing asset in a premier downtown location while benefiting from existing cash flow. Positioned along the vibrant pedestrian mall, the property benefits from exceptional visibility, steady foot traffic, and exposure to the countless community events, festivals, dining destinations, and boutique shopping experiences that make Old Town Winchester a regional attraction. The versatile floor plan provides endless possibilities for retail, office, restaurant, studio, mixed-use, or investment opportunities. The building showcases attractive storefronts, large display windows, and multiple levels of usable space that can accommodate a variety of business needs. Upper floors offer additional opportunities for expansion, office suites, creative workspaces, storage, or redevelopment potential (subject to applicable approvals). Whether you're an investor seeking a premier downtown asset, an entrepreneur looking to establish a flagship location, or someone passionate about preserving a piece of Winchester's rich history, this is a truly exceptional offering. Prime location, historic character, and significant square footage combine to create a one-of-a-kind ownership opportunity in the center of Winchester's thriving Walking Mall district.

Save
Ask
Tour
Hide
Share
Listing Snapshot
Price 
$747,000
Days On Site 
14 Days
Bedrooms 
N/A
Inside Area (SqFt) 
9,276 sqft
Total Baths 
N/A
Full Baths 
N/A
Partial Baths 
N/A
Lot Size 
N/A
Year Built 
1900
MLS® Number 
VAWI2010936
Status 
Active
Property Tax 
$4,105
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Estimated
Friends & Family
Recent Activity
5 days agoStatus changed to Active
5 days agoListing updated with changes from the MLS®
2 weeks agoListing first seen on site
General Features
Parking 
None
Property Sub Type 
Retail
Sewer 
Public Sewer
Special Circumstances 
Standard
SqFt Total 
9276
Water Source 
Public
Zoning 
B1
Interior Features
Appliances 
Electric Water Heater
Cooling 
Heat PumpElectric
Flooring 
Wood
Heating 
ElectricOilForced AirHeat Pump
Save
Ask
Tour
Hide
Share
Exterior Features
Construction Details 
ConcreteBrick
Community Features
School District 
WINCHESTER CITY PUBLIC SCHOOLS
Schools
School District
WINCHESTER CITY PUBLIC SCHOOLS
Elementary School
Unknown
Middle School
Unknown
High School
Unknown
Listing courtesy of MarketPlace REALTY



The real estate listing information is provided by Bright MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale or lease referenced on this web site comes from the Internet Data Exchange (IDX) program of the Bright MLS. This web site references real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties in listings may have been sold or may no longer be available. The data contained herein is copyrighted by Bright MLS and is protected by all applicable copyright laws. Any unauthorized collection or dissemination of this information is in violation of copyright laws and is strictly prohibited. Copyright © 2020 Bright MLS. All rights reserved.

Neighborhood & Commute
Source: Walkscore
Save
Ask
Tour
Hide
Share