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9,276 sqft

$747,000

14-16 S LOUDOUN STREET, WINCHESTER VA, 22601

Price per sqft$80.53
Built in1900
Property size9,276 sqft
Property typeCommercial

Overview

Active

Active-bright

Listed Aug 28, 2026

Updated 5 days ago

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.

Other Property Details

Taxes
$4,105
Tax Frequency
Annually
MLS provider logo

Listed by MarketPlace REALTY
Listing Contact: 5403033864 

The IDX display contains information sourced from the Bright MLS, Inc. as of 10/2/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

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Data last updated on 10/2/2026 at 12:11 AM UTC

 

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