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    Winchester, VA Multifamily Properties for Sale

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    Stephenson, VA Stephens City, VA Clear Brook, VA
    15 results
    Charming Duplex in Winchester, VA
    $599,900
    3,511 SF

    Charming Duplex in Winchester, VA

    1400 VALLEY Avenue, Winchester, VA 22601

    Versatile duplex with historic charm and income potential.

    • Duplex offers versatile options: live in one unit and rent the other, or rent out both for investment income.
    • Rear unit is already leased to a reliable tenant, providing immediate cash flow.
    • Enjoy updated bathrooms with walk‑in tiled showers and a new roof and gutters installed last year.
    • Original 1936 home with charming features: wood floors, tall ceilings, fireplace, and a stunning staircase.
    • Heating fuel converted to natural gas with new boilers installed in 2011.
    Updated: Apr 13
    View details
    Mixed-Use Property in Historic Downtown
    $1,500,000
    7,000 SF

    Mixed-Use Property in Historic Downtown

    314 N BRADDOCK Street, Winchester, VA 22601

    Versatile B1-zoned property with income and redevelopment potential.

    • B1 Zoning allows versatile use and redevelopment.
    • Located in the heart of the historic downtown district.
    • Significant redevelopment potential: Convert to residential, add up to two stories.
    • Approximately 7,000 SF of office space and 2,000 SF of ground‑level shop.
    • Includes 12 on‑site parking spaces.
    Updated: Jan 28
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    Turnkey Winchester Triplex Investment Opportunity
    $605,000
    4,396 SF

    Turnkey Winchester Triplex Investment Opportunity

    Triplex in downtown Winchester with strong cash flow potential.

    540 MONTICELLO Street, Winchester, VA 22601
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    Renovated Duplex Near Walking Mall
    $625,000
    1,948 SF

    Renovated Duplex Near Walking Mall

    Upgraded duplex near Winchester's historic Walking Mall, fully renovated in 2022.

    446 N LOUDOUN Street, Winchester, VA 22601
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    Winchester Multi-Family Investment Opportunity
    $679,900
    0.17 Acres

    Winchester Multi-Family Investment Opportunity

    Three-unit property in Winchester, fully rented and well-maintained.

    434-434 1/2 FAIRMONT AVE, Winchester, VA 22601
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    Turnkey Winchester Triplex Investment Opportunity
    $605,000

    Turnkey Winchester Triplex Investment Opportunity

    Downtown Winchester triplex with strong cash flow and commuter convenience.

    540 MONTICELLO St, Winchester, VA 22601
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    Turnkey Multifamily Investment Opportunity
    $699,900

    Turnkey Multifamily Investment Opportunity

    Three-unit property, fully rented, well-maintained, near downtown.

    434 FAIRMONT Ave, Winchester, VA 22601
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    Winchester Land Development Opportunity
    $4,500,000
    1,400 SF

    Winchester Land Development Opportunity

    11.43 acres prime for high-density multifamily and mixed-use development.

    801 FAIRMONT Avenue, Winchester, VA 22601
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    Charming Duplex: Investor Opportunity
    $325,000
    1,478 SF

    Charming Duplex: Investor Opportunity

    Turnkey duplex with excellent cash flow and private yard.

    433-435 Bryarly Road, Winchester, VA 22603
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    Turnkey Multi-Family Investment Property
    $699,900

    Turnkey Multi-Family Investment Property

    Three-unit property, fully rented, well-maintained, close to downtown.

    434-434 1/2 FAIRMONT Ave, Winchester, VA 22601
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    Approved Mixed-Use Development Opportunity
    $399,000
    1,340 SF

    Approved Mixed-Use Development Opportunity

    Approved mixed-use development site in downtown Winchester, Virginia.

    1 N BRADDOCK Street, Winchester, VA 22601
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    16-Unit Apartment Building Near Park
    $2,490,000
    0.50 Acres

    16-Unit Apartment Building Near Park

    Fully occupied apartment building with long-term tenants and off-street parking.

    600 -612 Smithfield Ave, Winchester, VA 22601
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    Remodeled Multi-Unit Property For Sale
    $1,850,000
    7,190 SF

    Remodeled Multi-Unit Property For Sale

    Completely remodeled multi-unit property with garage and high rental income.

    908 Cedar Creek Grade, Winchester, VA 22601
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    Winchester Multifamily Investment Opportunity
    $2,900,000
    0.50 Acres

    Winchester Multifamily Investment Opportunity

    Two buildings with twelve townhouse units, fully occupied.

    525-527 GRAY AVENUE, Winchester, VA 22601
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    Approved Mixed-Use Development Opportunity
    $449,000
    1,340 SF

    Approved Mixed-Use Development Opportunity

    Approved mixed-use site plan in downtown Winchester, Virginia.

    1 N Braddock St, Winchester, VA 22601
    View details
    Based on your search, we've compiled 80 Potential Opportunities for your consideration. Besides 15 Active listings in Winchester, VA, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 57 Off-Market properties to explore as potential leads, plus 4 Land Listings that present a potential for development.

    Opportunities in Nearby Cities

    Here are 4 Similar properties we found in Nearby Locations for your consideration.

    Three Detached Homes Investment Opportunity
    $575,000
    1,221 SF

    Three Detached Homes Investment Opportunity

    Three detached homes on one parcel, excellent investment opportunity.

    437, 441, 445 STEPHENSON RD, Stephenson, VA 22656
    View details
    Mixed-Use Property with Restaurant
    $750,000
    0.18 Acres

    Mixed-Use Property with Restaurant

    Restaurant and four apartments in high-traffic Front Royal location.

    1202 N ROYAL AVENUE, Front Royal, VA 22630
    View details
    Value-Add Mobile Home Park Opportunity
    $1,200,000

    Value-Add Mobile Home Park Opportunity

    Mobile home park with expansion potential near Route 11.

    149 Stephenson Road, Stephenson, VA 22656
    View details
    Residential Income Property For Sale
    $310,000
    0.25 Acres

    Residential Income Property For Sale

    Residential income property with level lot near downtown and I-66.

    211 LAUREL St, Front Royal, VA 22630
    View details

    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    Land Near Shepherd University
    $650,000
    3.70 Acres

    Land Near Shepherd University

    Prime land near Shepherd University with development potential.

    8285 MARTINSBURG Pike, Shepherdstown, WV 25443
    View details
    Land with Mobile Home, As-Is
    $39,900
    1.78 Acres

    Land with Mobile Home, As-Is

    1.78 acres with mobile home, well, and septic system.

    18531 Blackberry dr, Three Springs, PA 17264
    View details
    La Plata Land For Sale
    $250,000
    0.23 Acres

    La Plata Land For Sale

    0.23 acre parcel in La Plata, zoned CB.

    107 HOWARD Street, La Plata, MD 20646
    View details
    Land Ready for Development
    $275,000
    8.00 Acres

    Land Ready for Development

    8-acre land parcel zoned for mobile home park.

    1, Smithfield, PA 15478
    View details

    Off-Market Properties in Winchester, VA

    Consider similar Off-Market properties in Winchester, VA. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

    308 Smithfield Ave
    APARTMENT HOUSE (UNDER 5 UNITS)
    1,307 SF
    Value Estimation by Request

    308 Smithfield Ave, Winchester, VA 22601-5248

    View details
    329 National Ave
    APARTMENT HOUSE (UNDER 5 UNITS)
    2,288 SF Lot: 0.11 Acres
    Value Estimation by Request

    329 National Ave, Winchester, VA 22601-5208

    View details
    422 Braddock St
    APARTMENT HOUSE (UNDER 5 UNITS)
    2,416 SF Lot: 0.11 Acres
    Estimated value
    $535,000

    422 Braddock St, Winchester, VA 22601-3922

    View details
    821 Pennsylvania Ave
    APARTMENT HOUSE (UNDER 5 UNITS)
    2,072 SF Lot: 0.34 Acres
    Value Estimation by Request

    821 Pennsylvania Ave, Winchester, VA 22601-4957

    View details
    45 Race St
    APARTMENT HOUSE (UNDER 5 UNITS)
    1,248 SF Lot: 0.06 Acres
    Value Estimation by Request

    45 Race St, Winchester, VA 22601-5320

    View details
    301 Braddock St
    APARTMENT HOUSE (UNDER 5 UNITS)
    3,040 SF Lot: 0.12 Acres
    Value Estimation by Request

    301 Braddock St, Winchester, VA 22601-4180

    View details
    680 Berryville Ave
    APARTMENT HOUSE (UNDER 5 UNITS)
    1,672 SF
    Value Estimation by Request

    680 Berryville Ave, Winchester, VA 22601-5665

    View details
    514 Loudoun St
    APARTMENT HOUSE (UNDER 5 UNITS)
    3,608 SF Lot: 0.17 Acres
    Value Estimation by Request

    514 Loudoun St, Winchester, VA 22601-4642

    View details
    915 Berryville Ave
    APARTMENT HOUSE (UNDER 5 UNITS)
    1,932 SF Lot: 0.21 Acres
    Value Estimation by Request

    915 Berryville Ave, Winchester, VA 22601-5915

    View details

    Winchester, VA Multifamily Properties Investment Opportunities Market Analysis

    Explore 72 multifamily properties for sale in Winchester, VA, showcased through 15 active listings on our real estate platform. These investment opportunities span a total of 35,263 square feet of properties for sale, with an estimated market value of $11,953,900.

    Sale prices for multifamily properties in Winchester, VA start at $325,000, averaging $1,328,211, 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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    Top Commercial Asset Segments

    Apartment buildings 9
    Triplexes 5
    Duplexes 3
    Quadplexes 2
    Short term rental properties 1

    Property Size Breakdown

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

    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 median listing prices of real estate assets

    Neighborhood Average Price
    22603 $325K
    22601 $1.3M

    Taxes & Financing

    Tax Rate (average for all types) 0.50%
    Property Tax per SF $5.70 per sq ft
    Average Loan-to-Value 65.0%

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    • 22603

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