Add Listing
    For Sale
    • For Sale
    • For Lease
    • Recently Sold
    • Property Lookup
    • Brokers
    Residential Income
    1
    • Retail
    • Office
    • Residential Income
    • Restaurants
    • Industrial
    • Mixed-Use
    • Hospitality
    • Health Care
    • Sports & Entertainment
    • Land
    • Agricultural
    • Specialty
    Price
    Price range
    $
    $
    Size
    Property size / sq.ft.
    AI Search

    Meet Realmo: The Largest Hub
    of Commercial Real     Estate in the US

    Over 1 million active listings and over 150 million property profiles

    Winchester, VA Multifamily Properties for Sale

    List
    Map
    Fredericksburg, VA Roanoke, VA Bristol, VA
    13 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.

    • Income‑generating duplex with a reliable tenant already in place.
    • Front unit ideal for owner‑occupancy, boasting historic charm with wood floors, tall ceilings, fireplace, and a stunning staircase. Enjoy the sunroom.
    • Recent updates include a new roof and gutters (installed last year) and updated bathrooms with walk‑in tiled showers.
    • Separate utilities for each unit (except water/sewer).
    • Heating converted to natural gas with new boilers installed in 2011.
    Updated: Apr 13
    View details
    Turnkey Winchester Triplex Investment Opportunity
    $605,000
    4,396 SF

    Turnkey Winchester Triplex Investment Opportunity

    540 MONTICELLO Street, Winchester, VA 22601

    Triplex in downtown Winchester with strong cash flow potential.

    • Turnkey triplex investment property with all units currently leased, providing immediate and reliable income.
    • Prime downtown Winchester location, offering convenience and commuter access to I‑81, I‑66, and Northern Virginia.
    • Diverse unit mix: two 2‑bedroom units with updated kitchens, laundry rooms, and a large 5‑bedroom unit with a unique two‑level layout, private patio, and deck.
    • Recent renovations including LVP flooring, fresh paint, updated kitchens and baths, and newer appliances in each unit.
    • Newer roof (less than 3 years old) and new HVAC system (installed in 2025).
    Updated: Feb 17
    View details
    Winchester Multi-Family Investment Opportunity
    $699,900
    0.17 Acres

    Winchester Multi-Family Investment Opportunity

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

    434 FAIRMONT AVE, Winchester, VA 22601
    View details
    Mixed-Use Property in Historic Downtown
    $1,500,000
    0.42 Acres

    Mixed-Use Property in Historic Downtown

    Versatile B1-zoned property with income and redevelopment potential.

    314 N BRADDOCK Street, Winchester, VA 22601
    View details
    Rehabbed Duplex Near Old Town
    $299,000
    1,249 SF

    Rehabbed Duplex Near Old Town

    Low-maintenance duplex with strong rental income near historic Old Town.

    45 and 45 1/2 RACE Street, Winchester, VA 22601
    View details
    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
    View details
    Downtown Mixed-Use Redevelopment Opportunity
    $1,500,000
    7,000 SF

    Downtown Mixed-Use Redevelopment Opportunity

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

    314 N Braddock St, Winchester, VA 22601
    View details
    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
    View details
    Approved Mixed-Use Development Opportunity
    $449,000
    0.09 Acres

    Approved Mixed-Use Development Opportunity

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

    1 N BRADDOCK Street, Winchester, VA 22601
    View details
    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
    View details
    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
    View details
    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
    4.20 Acres with Rental Income
    $1,200,000
    4.20 Acres

    4.20 Acres with Rental Income

    4.20 acres with income-producing dwellings near downtown Winchester.

    3266 Valley Pike, Winchester, VA 22602
    View details
    Based on your search, we've compiled 514 Potential Opportunities for your consideration. Besides 13 Active listings in Winchester, VA, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 493 Off-Market properties to explore as potential leads, plus 4 Land Listings that present a potential for development.

    Explore Opportunities in Nearby Cities

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

    Martinsburg Multifamily Investment Opportunity
    $370,000
    3,504 SF

    Martinsburg Multifamily Investment Opportunity

    Four-unit building in Martinsburg, fully occupied, great investment property.

    535-537 ROUNDHOUSE Way, Martinsburg, WV 25404
    View details
    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
    Martinsburg Triplex with Income Potential
    $350,000
    3,082 SF

    Martinsburg Triplex with Income Potential

    Triplex featuring a single-family home and a duplex.

    627 Virginia Avenue, Martinsburg, WV 25401
    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

    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
    25 Acres Development Land Stanley
    $999,900
    25.00 Acres

    25 Acres Development Land Stanley

    25 acres ideal for housing or trailer park development.

    TBD S BOSLEY DR, Stanley, VA 22851
    View details
    Income-Producing Triplex on 3 Acres
    $425,000
    2,475 SF

    Income-Producing Triplex on 3 Acres

    Fully occupied triplex with land and business potential in Freeland.

    21525 YORK Road, Freeland, MD 21053
    View details
    Residential Land in Belington, WV
    Contact for pricing
    0.41 Acres

    Residential Land in Belington, WV

    Residential lots ready for new home construction or placement.

    254 Third Street, Belington, WV 26250
    View details

    Explore 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

    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

    329 National Ave

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,288 SF
    Value Estimation by Request
    329 National Ave, Winchester, VA 22601-5208
    View details
    422 Braddock St

    422 Braddock St

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,416 SF
    Value Estimation
    $535,000
    422 Braddock St, Winchester, VA 22601-3922
    View details
    821 Pennsylvania Ave

    821 Pennsylvania Ave

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,072 SF
    Value Estimation by Request
    821 Pennsylvania Ave, Winchester, VA 22601-4957
    View details
    45 Race St

    45 Race St

    APARTMENT HOUSE (UNDER 5 UNITS) • 1,248 SF
    Value Estimation by Request
    45 Race St, Winchester, VA 22601-5320
    View details
    301 Braddock St

    301 Braddock St

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,040 SF
    Value Estimation by Request
    301 Braddock St, Winchester, VA 22601-4180
    View details
    680 Berryville Ave

    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

    514 Loudoun St

    APARTMENT HOUSE (UNDER 5 UNITS) • 3,608 SF
    Value Estimation by Request
    514 Loudoun St, Winchester, VA 22601-4642
    View details
    915 Berryville Ave

    915 Berryville Ave

    APARTMENT HOUSE (UNDER 5 UNITS) • 1,932 SF
    Value Estimation by Request
    915 Berryville Ave, Winchester, VA 22601-5915
    View details
    219 Baker St

    219 Baker St

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,044 SF
    Value Estimation by Request
    219 Baker St, Winchester, VA 22601-5010
    View details
    346 National Ave

    346 National Ave

    APARTMENT HOUSE (UNDER 5 UNITS) • 2,772 SF
    Value Estimation by Request
    346 National Ave, Winchester, VA 22601-5256
    View details

    Winchester, VA Multifamily Properties Investment Opportunities Market Analysis

    Explore 506 multifamily properties for sale in Winchester, VA, showcased through 13 active listings on our real estate platform. These investment opportunities span a total of 2,588,959 square feet of properties for sale, with an estimated market value of $142,047,800.

    Sale prices for multifamily properties in Winchester, VA start at $95,000, averaging $339,016, and reaching up to $19,195,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

    List
    Map

    Browse Multifamily properties for Sale Near Winchester, VA

    Popular Searches in Winchester, VA

    Popular Categories

    Most Searched ZIP Codes in Winchester, VA

    • 22601
    • 22602

    Select Neighborhood

    Google sign-in failed. Please try again or use another login method.
    Sign Up Successful!
    You now have access to more from Realmo!