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    Winchester, VA Commercial Real Estate for Sale

    106 results
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    Winchester Retail/Office Space For Sale
    $525,000
    0.28 Acres

    Winchester Retail/Office Space For Sale

    2109 VALLEY Avenue, Winchester, VA 22601

    Retail/office space in Winchester's Technology and Enterprise zone.

    • High‑traffic location (14,000 vehicles/day) on a main corridor with excellent visibility.
    • Located in Technology and Enterprise zones offering business incentives.
    • Flexible NDD zoning allows for mixed‑use, retail, office, and residential development (single‑family, two‑family, multi‑family).
    • Spacious: Over 2300 SF of retail/office space plus 330 SF of attached storage.
    • Ample off‑street parking for 15+ vehicles with a recently paved rear parking lot.
    Updated: Mar 24
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    Historic Winchester Inn For Sale
    $1,200,000
    0.30 Acres

    Historic Winchester Inn For Sale

    217 W BOSCAWEN Street, Winchester, VA 22601

    Historic property suitable for residence, B&B, or professional offices.

    • Prime location in Winchester's Historic District, two blocks from Old Town Walking Mall.
    • Zoned B1, allowing for use as a single‑family residence, bed and breakfast, or professional office.
    • Six large bedrooms and five full baths.
    • Historically significant property with unique architectural features, including wrap‑around stairs and floor‑to‑ceiling windows.
    • Private parking in the rear, a downtown rarity.
    Updated: Mar 16
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    Downtown Winchester Triplex Investment Opportunity
    $605,000
    4,396 SF

    Downtown Winchester Triplex Investment Opportunity

    Turnkey triplex in downtown Winchester with strong cash flow.

    540 MONTICELLO Street, Winchester, VA 22601
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    Prime Office in Winchester, VA
    $1,182,695

    Prime Office in Winchester, VA

    7082 SF office space in established business park.

    252 AIRPORT unit: 3, Winchester, VA 22602
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    Downtown Winchester Office Building For Sale
    $1,512,000

    Downtown Winchester Office Building For Sale

    Prestigious office building in the heart of downtown Winchester.

    38 ROUSS Avenue, Winchester, VA 22601
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    High Traffic Retail Opportunity
    $999,000
    0.82 Acres

    High Traffic Retail Opportunity

    High-visibility retail property on 0.82 acres, ideal for various businesses.

    1694 BERRYVILLE, Winchester, VA 22602
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    Commercial Land For Sale/Lease
    $1,500,000
    5.26 Acres

    Commercial Land For Sale/Lease

    5.26 acres of commercial land, sale or lease.

    153 WELLTOWN Road, Winchester, VA 22602
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    Office Condo in Winchester, VA
    $380,000

    Office Condo in Winchester, VA

    2000 SF office condo in excellent condition and location.

    240 AIRPORT Road unit: 2, Winchester, VA 22602
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    Prime Commercial Office Space
    $1,300,000

    Prime Commercial Office Space

    Highly versatile office space with excellent visibility and parking.

    650 MILLWOOD Avenue, Winchester, VA 22601
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    Prime Commercial Land on Route 522
    $675,000
    1.52 Acres

    Prime Commercial Land on Route 522

    Highly visible 1.52-acre pad site with utilities in place.

    204 MARANTO MANOR DR, Winchester, VA 22602
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    2.3 Acre Outparcel For Sale
    $1,100,000
    2.30 Acres

    2.3 Acre Outparcel For Sale

    2.3 acre outparcel ideal for auto, office, retail, flex.

    PLEASANT VALLEY, Winchester, VA 22601
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    Downtown Winchester Mixed-Use Redevelopment Opportunity
    $1,500,000
    0.42 Acres

    Downtown Winchester Mixed-Use Redevelopment Opportunity

    B1-zoned property with income, redevelopment potential, and downtown location.

    314 N BRADDOCK Street, Winchester, VA 22601
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    Versatile Retail/Office Space Available
    $525,000
    2,630 SF

    Versatile Retail/Office Space Available

    Retail/office space with high visibility and mixed-use zoning.

    2109 VALLEY Ave, Winchester, VA 22601
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    64+ Acres in Winchester, VA
    $1,300,000
    64.91 Acres

    64+ Acres in Winchester, VA

    Scenic 64+ acre parcel suitable for farming or private estate.

    CEDAR CREEK GRADE lot: 7, Winchester, VA 22602
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    Prime Land in Winchester, VA
    $3,200,000
    13.05 Acres

    Prime Land in Winchester, VA

    13.05 acres with high visibility and multiple development possibilities.

    0 NORTHWESTERN Pike, Winchester, VA 22602
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    Land with Development Potential
    $750,000
    1.33 Acres

    Land with Development Potential

    Mixed-use land in Winchester with development possibilities.

    903 N LOUDOUN Street, Winchester, VA 22601
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    Secluded Land with Mountain Views
    $1,550,000
    152.44 Acres

    Secluded Land with Mountain Views

    152.44 acres of unrestricted land near Winchester, Virginia.

    152.44 Acres Lot 2 LAUREL GROVE Road, Winchester, VA 22602
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    Historic Winchester Office Building For Sale
    $1,925,000
    11,060 SF

    Historic Winchester Office Building For Sale

    Downtown office building with hardwood floors and off-street parking.

    40 W Piccadilly St, Winchester, VA 22601
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    Flex Space For Sale
    $899,000
    5,000 SF

    Flex Space For Sale

    5000 SF flex space leased until August 2025.

    250 AIRPORT ROAD, Winchester, VA 22602
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    Secluded Land with Panoramic Views
    $1,595,000
    158.44 Acres

    Secluded Land with Panoramic Views

    158.44 acres of private land with unmatched 360-degree views.

    158.5 Acres Lot 3 LAUREL GROVE RD., Winchester, VA 22602
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    Historic Inn or Office Opportunity
    $1,200,000
    0.30 Acres

    Historic Inn or Office Opportunity

    Historic property in Winchester's Historic District, ideal for various uses.

    217 W Boscawen St, Winchester, VA 22601
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    Historic Landmark Building in Winchester
    $1,299,000
    7,500 SF

    Historic Landmark Building in Winchester

    Iconic, meticulously restored building with income potential in downtown Winchester.

    45 BOSCAWEN E STREET, Winchester, VA 22601
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    Turn Key Auto Service Center
    $1,500,000
    11,000 SF

    Turn Key Auto Service Center

    Auto service center with excellent visibility on Pleasant Valley Road.

    116 Bruce Dr, Winchester, VA 22601
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    Historic Property with Commercial Potential
    $450,000
    1.65 Acres

    Historic Property with Commercial Potential

    B-2 commercially zoned property on 1.65 acres near I-81.

    229 Garber Ln, Winchester, VA 22602
    View details

    Winchester, VA Commercial Real Estate Investment Opportunities Market Analysis

    Explore 106 commercial real estate for sale in Winchester, VA, showcased through 106 active listings on our real estate platform. These investment opportunities span a total of 166,158,749 square feet of properties for sale, with an estimated market value of $59,347,700.

    Sale prices for business properties in Winchester, VA start at $199,900, averaging $1,447,504, and reaching up to $4,500,000 — 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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