Winchester, VA Commercial Real Estate for Sale

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126 properties
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Freestanding Drive-Through Restaurant
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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Two-Tenant NNN Retail Center
Updated: Sep 15
Two-Tenant NNN Retail Center

105 MARKET Street, Winchester, VA 22603

$4,990,000
1.12 AC lot
Two‑tenant true NNN retail center at 105‑109 Market Street
1.12 acres with a 2020 construction date
Corporate Starbucks tenant with S&P BBB+ rating
V Nails & Spas lease extends through 2035
10% rent step‑ups every five years
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Signalized Corner Commercial Land
Signalized Corner Commercial Land

721 FRONT ROYAL Pike, Winchester, VA 22602

$550,000
0.75 AC lot

RP-zoned corner parcel with road frontage and potential commercial uses subject to rezoning and applicable approvals.

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Mixed-Use Building with Retail and Offices
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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Office Building with Open Main Floor
Office Building with Open Main Floor

220 E CORK Street, Winchester, VA 22601

$449,000
0.18 AC lot

A lower level adds private offices, storage, a break area, and two bathrooms.

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Office Building with Ground-Level Shop
Office Building with Ground-Level Shop

314 N BRADDOCK Street, Winchester, VA 22601

$1,250,000
0.42 AC lot

B1-zoned property combines office space, a ground-level shop, and on-site parking.

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Interstate Commercial Land
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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Two-Storefront Retail Building
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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Masonry Retail Building
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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Downtown Office Building
Downtown Office Building

124 S BRADDOCK Street, Winchester, VA 22601

$439,999
0.11 AC lot

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

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Leased Two-Story Office Building
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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Three-Story Retail Building
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
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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Multi-Tenant Office Building
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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Commercial Land at Signalized Intersections
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
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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Drive-Through Commercial Outparcel
Drive-Through Commercial Outparcel

535 Patsy Cline Boulevard, Winchester, VA 22601

$675,000
890 sqft 0.57 AC lot

Commercial outparcel with current drive-thru operation, zoned CM-1, and utilities available with water and sewer connections.

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Commercial Land Development Site
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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Historic Two-Story Office Building
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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Agricultural Land with Building Right
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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All-Brick Office Suite with Parking
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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Historic Brick Office Building
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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Medical Office Condo Suite
Medical Office Condo Suite

142B Linden Drive, Unit 106, Winchester, VA 22601

$1,350,000
6,200 sqft

Medical office condo with immediate availability, ample parking, and a current tenant under lease.

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Land with Highway Exposure
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 126 commercial real estate for sale in Winchester, VA, showcased through 126 active listings on our real estate platform. These investment opportunities span a total of 481,069 square feet of properties for sale, with an estimated market value of $136,304,925.

Sale prices for business properties in Winchester, VA start at $94,999, averaging $1,584,940, 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
22601 $1.3M
22602 $1.6M
22603 $1.6M

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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