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Winchester, VA Multifamily Homes & Duplexes for Sale

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  • /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

    Bridget Aikens Colony Realty

    386 Round Hill Rd, Winchester, VA 22602
  • /67

    $625,000

    • 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
  • /56

    $2,098,000

    • 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
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    $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
$401,000
Median Single Family Sale Price
$429,620
Median Townhouse Sale Price
$390,000
Median 2 Bedroom Sale Price
$247,500
Median 1 Bedroom Sale Price
$225,000
Average Price Per Sq Ft
$209
Number of Homes for Sale
290
Last 12 months Home Sales
1,031
Months of Supply
3.40
Median List Price
$419,990
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
0%
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