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Winchester, VA Multifamily Homes & Duplexes for Sale

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  • /88

    $435,000

    • Studio
    • 2,152 Sq Ft

    26 A Jackson Ave, Winchester, VA 22601

    Rare Opportunity: Turnkey Duplex in Winchester – Vacant, Updated, and Ready for Your Next Move! A rare and an exceptional opportunity to own a two-unit duplex in Winchester City— vacant and ready for your plans. Whether you’re an investor seeking strong cash flow or an owner-occupant looking to live in one unit and rent the other, this property offers flexibility, income potential, and low

    Agent Photo

    Melanie Lucero

    Real Broker, LLC

    (540) 386-1285

    26 A Jackson Ave, Winchester, VA 22601
  • /69

    $605,000

    • Studio
    • 4,396 Sq Ft

    540 Monticello St, Winchester, VA 22601

    Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location!Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers

    Laura King MarketPlace REALTY

    540 Monticello St, Winchester, VA 22601
  • /53

    $654,000

    • Studio
    • 3,511 Sq Ft

    1400 Valley Ave, Winchester, VA 22601

    Versatile on Valley!So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out

    Danielle Spriggs Real Broker LLC

    1400 Valley Ave, Winchester, VA 22601
  • /20

    $449,900

    • Studio
    • 2,376 Sq Ft

    510 N Loudoun St, Winchester, VA 22601

    All brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD/1BA with unfinished attic, main floor is 1BR/1BA (Both have rear balcony) and basement unit has access to storage area and includes1BD/1BA. All units have washer/dryer (Basement unit washer/dryer belongs to tenant). Owner/Agent and home inspection report available upon request.

    Dave Spence RE/MAX Roots

    510 N Loudoun St, Winchester, VA 22601
  • /28

    $475,000

    • Studio
    • 2,736 Sq Ft

    386 Round Hill Rd, Winchester, VA 22602

    *** ATTENTION INVESTORS - OFFERED AT A NEW PRICE!! *** You will want to check out this fantastic opportunity - with a history of POSITIVE CASH FLOW these two ADJACENT PROPERTIES on a combined total of 1.91-acres in Winchester (just minutes from Valley Health Campus, shopping, restaurants and Rt. 37) may be what you are looking for! These two parcels are to be sold TOGETHER; they are not offered

    Bridget Aikens Colony Realty

    386 Round Hill Rd, Winchester, VA 22602
  • /56

    $1,899,000

    • Studio
    • 7,190 Sq Ft

    908 Cedar Creek Grade, Winchester, VA 22601

    In town location for this completely remodeled multi unit property. This property contains 4 homes and 2 apartments that have been completely refinished. The main home is currently lived in by the owner and is attached to a indoor swimming pool. The other 3 homes and 2 apartments are leased and are bringing over$10,500 monthly. If you choose rent the main house income would be much higher. .

    Meridee Powars Link Realty Services LLC

    908 Cedar Creek Grade, Winchester, VA 22601
  • /2

    $500,000

    • Studio
    • 1,175 Sq Ft

    513 and 525 Monticello St, Winchester, VA 22601

    For Sale – 1.89 + Acres Redevelopment Site located just off Valley Avenue in southern Winchester. Property consists of 2 parcels and includes a single family detached rental and one unimproved lot. Lot is zoned MR and Improved parcel is zoned B-2. Property is ideally suited for multi-family development. All properties are leased. Call listing broker for additional information. Do not disturb

    Brett Haynes Oakcrest Commercial LLC.

    513 and 525 Monticello St, Winchester, VA 22601

Why Live in Winchester

Winchester, located in the Shenandoah Valley of Virginia, is a small but rapidly growing town known for its apple-themed events, historic downtown, and accessibility to larger cities like Washington D.C. and Loudoun County. The town's economy is driven by health care, retail, and manufacturing, with Valley Health being a major employer. Commuters often use Interstate 81 and U.S. Route 50 for the 75-mile trip to Northern Virginia and D.C. Winchester Transit provides local bus services, and Dulles International Airport is 50 miles away. The town experiences humid summers and mild winters, with occasional minor flooding due to heavy rainfall. Winchester's housing market offers more affordable options compared to neighboring counties, with historic homes near downtown featuring Craftsman and Colonial Revival designs. The Shenandoah Apple Blossom Festival is a major annual event, attracting around 250,000 visitors. Residents enjoy performances at local theaters, shopping at the Apple Blossom Mall, and dining in Old Town Winchester. Outdoor enthusiasts can explore Jim Barnett Park, the Museum of the Shenandoah Valley, and nearby Shenandoah National Park. Winchester City Public Schools serve over 4,000 students and are highly rated, while Shenandoah University offers strong liberal arts and performing arts programs. Despite its small size, Winchester boasts a rich history with several Civil War sites and the Patsy Cline Historic House.

Home Trends in Winchester, VA

Housing Trends

Median Sale Price
$419,350
Median Single Family Sale Price
$444,990
Median Townhouse Sale Price
$389,880
Median 2 Bedroom Sale Price
$250,000
Average Price Per Sq Ft
$207
Number of Homes for Sale
273
Last 12 months Home Sales
1,077
Months of Supply
3.00
Median List Price
$429,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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