Winchester, VA Commercial Real Estate for Sale

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162 properties

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Updated: Jul 20

Freestanding Drive-Through Restaurant

535 PATSY CLINE Boulevard, Winchester, VA 22601

$675,000

0.57 AC lot

Operating drive‑through on a 0.57‑acre commercial outparcel
CM‑1 zoning with water and sewer connections
Access from Patsy Cline Boulevard and South Pleasant Valley Road
Minutes from the I‑81 interchange
Built in 2021 with vinyl siding, heat pump heating, and ductless cooling

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Updated: Jan 28

Office Building with Ground-Level Shop

314 N BRADDOCK Street, Winchester, VA 22601

$1,250,000

0.42 AC lot

Approximately 7,000 SF of office space plus a 2,000 SF ground‑level shop
B1 zoning in Winchester’s historic downtown district
0.4199‑acre property at 314 N Braddock Street
12 on‑site parking spaces, plus on‑street parking
Brick building constructed in 1950

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Interstate Commercial Land

153 WELLTOWN Road, Winchester, VA 22602

$1,950,000

5.26 AC lot

Commercial land with extensive frontage, signalized-access connectivity, and zoning that permits multiple flex uses and restaurants.

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Restored Mixed-Use Building

48 W Boscawen, Winchester, VA 22601

$1,724,000

9,355 sqft

Renovated occupied floors accommodate retail and office tenancy in downtown Winchester near the pedestrian mall.

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Masonry Retail Building

1694 BERRYVILLE, Winchester, VA 22602

$999,000

0.82 AC lot

B2-zoned commercial property with route access, secondary lane access, and a month-to-month tenancy.

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Historic Mixed-Use Building

185 LOUDOUN Street N, Winchester, VA 22601

$1,395,000

0.04 AC lot

Modernized, fully occupied property combines ground-floor retail with office suites across three upper levels.

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Downtown Office Building

124 S BRADDOCK Street, Winchester, VA 22601

$487,900

0.11 AC lot

Stucco construction, driveway parking, and electric heating support the existing office layout.

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Mixed-Use Building with Retail and Offices

185 N Loudoun St, Winchester, VA 22601

$1,395,000

7,500 sqft

Modernized historic property combines ground-floor retail with office suites on upper levels along Winchester’s Walking Mall.

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Three-Story Retail Building

14-16 S LOUDOUN Street, Winchester, VA 22601

$747,000

Two leased storefronts occupy a multi-level commercial building on Winchester’s pedestrian Walking Mall.

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Brick Office Units with Open Layout

252 AIRPORT, Winchester, VA 22602

$1,182,695

Business-park offices feature executive rooms, a breakroom, multiple restrooms, and on-site parking.

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Two-Storefront Retail Building

14-16 S LOUDOUN STREET, Winchester, VA 22601

$747,000

9,276 sqft

Three-story commercial property with leased retail suites, display windows, and additional upper-level space.

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Commercial Land at Signalized Intersections

201 MARANTO MANOR DR, Winchester, VA 22602

$675,000

1.52 AC lot

The site carries B-2 Highway Commercial Di zoning and is accessed directly from Front Royal Pike.

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Agricultural Land with Rolling Pasture

950 STONY HILL Road, Winchester, VA 22603

$925,000

156.58 AC lot

Property includes farmable portions, available electric, and livestock currently on site.

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Leased Two-Story Office Building

12 N Washington St, Winchester, VA 22601

$1,975,000

11,340 sqft

Fully leased office property with basement space and on-street parking.

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Commercial Land Development Site

0 NORTHWESTERN Pike, Winchester, VA 22602

$3,200,000

13.05 AC lot

High-visibility development land along Route 50 with prior concept plans for retail and medical uses.

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Agricultural Land with Building Right

CEDAR CREEK GRADE lot: 7, Winchester, VA 22602

$689,000

64.91 AC lot

Preservation acreage combines open ground and partial woodland for agricultural or rural estate use.

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Multi-Tenant Office Building

47 W Jubal Early Dr, Winchester, VA 22601

$938,000

4,800 sqft

Modernized office property with three tenants, on-site parking, and full lease occupancy.

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Historic Brick Office Building

38 ROUSS Avenue, Winchester, VA 22601

$995,000

Downtown property offers multiple suite configurations near civic offices, the courthouse, and public parking facilities.

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All-Brick Office Suite with Parking

252 Airport Unit 3, Winchester, VA 22602

$1,182,695

7,500 sqft

All-brick office suite in a business park with multiple private offices, breakroom, and abundant free parking.

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CM1 Commercial Land with Frontage

PLEASANT VALLEY, Winchester, VA 22601

$1,100,000

2.30 AC lot

CM1-zoned land with utilities reaching the site and nearby retail operators including Walmart, Target, and Panera Bread.

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Historic Two-Story Office Building

407 S Loudoun St, Winchester, VA 22601

$625,000

3,618 sqft

Two finished floors support a multi-suite office layout with conference and kitchenette areas.

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Fully Leased Multi-Tenant Office Building

47 W JUBAL EARLY Drive, Winchester, VA 22601

$938,000

Modernized brick office property with multiple suites, central air, forced-air heating, and an on-site parking lot.

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Established Wendy's Restaurant For Sale

1100 Berryville Ave, Winchester, VA 22601

$2,109,200

2,462 sqft 0.57 AC lot

Long-term Wendy's location with recent renovations and strong sales.

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Land with Highway Exposure

1667 N FREDERICK Pike, Winchester, VA 22603

$1,400,000

5.73 AC lot

Commercial land with great exposure on State Route 37.

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Winchester, VA Commercial Real Estate Market Trends and Statistics

Explore 162 commercial real estate for sale in Winchester, VA, showcased through 162 active listings on our real estate platform. These investment opportunities span a total of 592,364 square feet of properties for sale, with an estimated market value of $131,356,480.

Sale prices for business properties in Winchester, VA start at $94,999, averaging $1,475,915, and reaching up to $7,200,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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Demographics Overview

Population 79K

Population Growth (5Y) +7.1%

Median Household Income $82,773

College Educated 32.0%

High-Yield Neighborhoods for Investment

Identify Winchester submarkets with the highest inventory density on the market and evaluate the average listing prices of real estate assets

Neighborhood	Average Price
22604	$947K
22603	$993K
22601	$1.2M
22602	$1.7M

Taxes & Financing

Tax Rate (average for all types) 0.50%

Property Tax per SF $5.70 per SF

Average Loan-to-Value 65.0%

Property Size Breakdown

The majority of commercial real estate listings in Winchester fall within the 100,000+ square foot range.

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