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Bennington, VT Multifamily Homes & Duplexes for Sale

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  • /29

    $415,000

    • 6 Beds
    • 3 Baths
    • 5,208 Sq Ft

    126 Washington Ave, Bennington, VT 05201

    Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property’s historic character, while modern updates support comfortable living and reliable income potential.

    Agent Photo

    Vicki Wilson

    Maple Leaf Realty

    (802) 266-4364

    126 Washington Ave, Bennington, VT 05201
  • /40

    $215,000

    • 5 Beds
    • 2 Baths
    • 2,201 Sq Ft

    317 Pleasant St, Bennington, VT 05201

    Centrally located renovated Bennington duplex, with backyard and garage. This duplex can generate an annual net operating income of ~$23k+ at current numbers (~10.5%), producing robust returns from cash flow and not speculation! Owner performed renovations since acquiring, including to heating systems, plumbing, and gut renovation of the upstairs 2br (currently rented for $1,400).

    Michael Gilman 3GEN Real Estate Inc

    317 Pleasant St, Bennington, VT 05201
  • /15

    $269,000

    • 2 Beds
    • 1 Bath
    • 2,500 Sq Ft

    624 Main St, Bennington, VT 05201

    Prime Mixed-Use Building on Main Street-Bennington, Vermont. Located in the heart of downtown Bennington, this versatile mixed-use property offers an excellent opportunity for both investors and owner-occupants. The main level features a spacious, adaptable commercial space ideal for retail, office, or service-based businesses. With its high visibility and foot traffic on Main Street, this is a

    Kelley Mccarthy Mahar McCarthy Real Estate

    624 Main St, Bennington, VT 05201
  • /10

    $245,000

    • 4 Beds
    • 2 Baths
    • 1,652 Sq Ft

    209 Grove St Unit 11, Bennington, VT 05201

    Well-maintained 2-unit property offering flexibility for owner-occupants or investors. The main-level unit features 3 bedrooms, a full bath, an eat-in kitchen with new cabinets, and a laundry room with washer and dryer. The upstairs unit offers 1 bedroom, a full bath, eat-in kitchen, and a cozy living room with hardwood floors. Exterior features include a nice backyard, 2 covered parking spaces

    Julie Glover Mahar McCarthy Real Estate

    209 Grove St Unit 11, Bennington, VT 05201
  • /33

    $295,000

    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft

    254 Union St, Bennington, VT 05201

    Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs.Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable

    Cassie Barbeau Mahar McCarthy Real Estate

    254 Union St, Bennington, VT 05201
  • /2

    $225,000

    • 6 Beds
    • 2 Baths
    • 2,112 Sq Ft

    303-305 Gage St, Bennington, VT 05201

    Low maintenance duplex in Bennington. Offering good rental history and income. 2 -3 bedroom units, newer systems, vinyl siding and more. Walking distance to town. schools and recreation.

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    303-305 Gage St, Bennington, VT 05201
  • /4

    $249,000

    • 5 Beds
    • 3 Baths
    • 2,184 Sq Ft

    137 Park St, Bennington, VT 05201

    Terrific income producing property. 2 - 1 bedroom units and a 3 bedroom unit with a garage. Close to town and modern systems. Good rental history. Is in a flood zone but owner has found a good flood insurance company.

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    137 Park St, Bennington, VT 05201
  • /39

    $279,900

    • 5 Beds
    • 2 Baths
    • 2,294 Sq Ft

    218 Union St, Bennington, VT 05201

    Charming Downtown Victorian - Income Opportunity Meets Timeless StyleTucked behind the classic facade of this downtown Bennington gem lies an incredible opportunity-for homeowners and investors alike. Located in the heart of downtown on a street known for both professional and residential appeal, this Victorian-style duplex offers versatility, character, and reliable income potential. Each

    Kelley Mccarthy Mahar McCarthy Real Estate

    218 Union St, Bennington, VT 05201
  • /4

    $190,000

    • 5 Beds
    • 2 Baths
    • 1,478 Sq Ft

    32-34 Sage St, Bennington, VT 05257

    Duplex in North Bennington offering 1 way street location. decent yard and 2 - 2 bedroom units. Good investment potential in a walkable and sought location. Town water and sewer. Current tenants keep their units up well.

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    32-34 Sage St, Bennington, VT 05257

Why Live in Bennington

Bennington, Vermont, is a small town nestled within the Green Mountains, known for its rich history and outdoor activities. Established in 1749, Bennington is the first town chartered in Vermont, featuring historic sites like the Bennington Monument and Old First Church Cemetery. Downtown Bennington is revitalizing with new amenities such as a bandstand for summer concerts and a splash pad for families, alongside a growing arts and theater scene. Housing options range from historic homes dating back to the Battle of Bennington in 1777 to modern buildings and rural homes in Shaftsbury and Arlington. Residents enjoy four seasons of outdoor activities, including skiing at Prospect Mountain Ski Area, hiking, and fly fishing in natural waterfalls and rivers. Robert Frost's home, now a museum, adds to the town's cultural attractions. Main Street offers a variety of dining options, from authentic English food to homemade ice cream and cozy pubs, with several small grocery stores and markets nearby. Bennington College, known for its visual and performing arts programs, is located north of downtown, along with other higher education institutions. Commuting is convenient, with Manchester 25 miles away and easy access to New York and Massachusetts borders. The town has seen a decrease in both violent and property crime in 2023, making it safer than the national average.

Home Trends in Bennington, VT

Housing Trends

Median Sale Price
$254,300
Median Single Family Sale Price
$265,000
Median Townhouse Sale Price
$199,900
Median 2 Bedroom Sale Price
$155,000
Median 1 Bedroom Sale Price
$20,000
Average Price Per Sq Ft
$186
Number of Homes for Sale
21
Last 12 months Home Sales
102
Months of Supply
2.50
Median List Price
$267,450
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-1%
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