21

Bennington, VT Houses for Sale

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  • /16

    $145,000

    • 3 Beds
    • 1.5 Baths
    • 1,485 Sq Ft

    755 Main St, Bennington, VT 05201

    Many possibilities with this property located on Main Street in Bennington. Zoned village commercial but currently a 3 bedroom 1 and a half bath home. Nice kitchen, dining room, living room, main level primary with half bath, main level laundry and more. Needs some TLC. Won't qualify for first time homebuyer programs.

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 444-8936

    755 Main St, Bennington, VT 05201
  • /41

    $295,000

    • 5 Beds
    • 2 Baths
    • 1,588 Sq Ft

    226 North St, Bennington, VT 05201

    This beautifully detailed 1880 Victorian in Bennington's residential commercial district offers flexibility and income potential all in one. Currently operating as a successful, fully furnished Airbnb, this 5-bedroom, 2-bath property is ready for its next owner. Whether you're an investor looking for cash flow or a buyer seeking a spacious and charming single family home. The main level

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    (802) 327-7149

    226 North St, Bennington, VT 05201
  • /11

    $179,900

    • 4 Beds
    • 2 Baths
    • 2,643 Sq Ft

    905 County St, Bennington, VT 05201

    Recently this home was a 2 unit (up and down). The current owner has doing work to convert it into a large single family home. Currently 4 bedrooms, 2 bathrooms and many possible room configurations. Also could easily be converted back to a 2 Unit. Many possibilities to put your finishing touches on this property.

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 204-5943

    905 County St, Bennington, VT 05201
  • /33

    $229,900

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft

    5 Center St, Bennington, VT 05201

    Welcome to 5 Center Street in the heart of Bennington! This charming single level home offers 3 bedrooms and 1 full bath across a well designed 1,144 sq. ft. floor plan the perfect size for easy living and energy efficiency. Whether you’re looking to downsize, purchase your first home, or simply enjoy the convenience of one floor living, this home is a wonderful fit.Inside, you’ll find a

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    (802) 553-3433

    5 Center St, Bennington, VT 05201
  • /53

    $299,000

    • 2 Beds
    • 1 Bath
    • 1,708 Sq Ft

    14 Crescent Ln, Bennington, VT 05201

    An Idyllic Ranch Retreat with 235 Feet of beautiful shoreline totaling 1.3 Acres . This 2 bedroom ranch home has great water views from every room. . The large, bright primary bedroom is a sanctuary unto itself. Imagine waking each morning to the tranquil sight of lake waters stretching beyond the window, or slipping into the adjoining hot tub room for a restorative soak. This unique space leads

    Dan Mason Perrott Realty

    14 Crescent Ln, Bennington, VT 05201
  • /47

    $295,000

    • 3 Beds
    • 1.5 Baths
    • 1,687 Sq Ft

    174 Morgan St, Bennington, VT 05201

    Sweet Ranch home that's not too big, not too small, just the right size! Set on 0.52 acres, it's a lovely lot surrounded by trees on 2 sides and has a beautiful mountain view. Attached 1-car garage with built-in storage has an automatic garage door and directly enters the galley kitchen. Refrigerator was removed because it stopped working... you can replace it with the same size, use the

    Jenifer Prouty Hoffman Hoffman Real Estate

    174 Morgan St, Bennington, VT 05201
  • /30

    $365,000

    • 3 Beds
    • 2 Baths
    • 1,753 Sq Ft

    374 Overlea Rd, North Bennington, VT 05257

    A stunning three bedroom, two bath home on a wooded lot with mountain views and bordered on several sides by serene farm pastures! Just a few minutes from downtown Bennington and even closer to the village of North Bennington! Tons of natural light inside that compliments the updated kitchen and open dining / living room areas. First floor includes enclosed rear sun porch/mudroom, laundry and

    Gregory Cutler Four Seasons Sotheby's Int'l Realty

    374 Overlea Rd, North Bennington, VT 05257
  • /25

    $295,000

    • 3 Beds
    • 2.5 Baths
    • 1,888 Sq Ft

    120 Albe Dr, Bennington, VT 05201

    Comfortable, convenient and close to downtown Bennington and all its amenities. Built in 2001, in a quiet neighborhood, the home features 3 bedrooms and 2.5 baths,, which includes a primary suite with its own bath. The first floor offers a spacious eat-in kitchen with washer and dryer efficiently installed in a large closet. The kitchen also has glass doors that open to private deck and a level

    Ann Greenwood Alton + Westall Real Estate Agency, LLC

    120 Albe Dr, Bennington, VT 05201
  • /41

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 2,116 Sq Ft

    245 Southshire Dr, Bennington, VT 05201

    Nestled in one of Bennington's most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm--all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System(BATS). The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a gracious

    Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

    245 Southshire Dr, Bennington, VT 05201
  • /49

    $325,000

    • 3 Beds
    • 1.5 Baths
    • 1,664 Sq Ft

    93 Pace Rd, Bennington, VT 05201

    Welcome Home to Your Private Woodland Retreat! ??Tucked away on a serene 2.75-acre wooded lot, this charming 3-bedroom, 1.5-bath home offers a rare blend of comfort, updates, and outdoor magic. With approximately 1,664 sq ft of living space, you’ll have plenty of room to stretch out—and three spacious decks to soak in those treetop views from every angle!? What’s New? Just about

    Harvey Roettinger RE/MAX North Professionals

    93 Pace Rd, Bennington, VT 05201
  • /48

    $599,900

    • 4 Beds
    • 3.5 Baths
    • 3,742 Sq Ft

    34 Southshire Dr, Bennington, VT 05201

    Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, VermontSet on a generous 2.4-acre lot in the sought-after Southshire neighborhood, this spacious ranch offers comfortable living with scenic privacy and versatile space. The main level features a well-appointed kitchen that opens to a cozy family room complete with a fireplace and built-in bookshelves, all

    Kelley Mccarthy Mahar McCarthy Real Estate

    34 Southshire Dr, Bennington, VT 05201
  • /12

    $499,000

    • 6 Beds
    • 4 Baths
    • 15,179 Sq Ft

    423 Main St, Bennington, VT 05201

    Historic building in heart of downtown Bennington with solid income from existing commercial tenancy and a fantastic second floor begging to be utilized as residential space. This loft type space is approx. 8,000 sq. ft. and would be an amazing living space (or several) with varying exposure, views of mountains in the distance and of the downtown area. The building offers an abundance of indoor

    Chris Long BHG Masiello Brattleboro

    423 Main St, Bennington, VT 05201
  • /36

    $399,000

    • 5 Beds
    • 3 Baths
    • 3,118 Sq Ft

    100 McCarthy Acres, North Bennington, VT 05257

    Nearly Lakefront Living in the Heart of North Bennington!Come for the space—stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

    Nicholas Charest Maple Leaf Realty

    100 McCarthy Acres, North Bennington, VT 05257
  • /26

    $249,900

    • 4 Beds
    • 2 Baths
    • 1,278 Sq Ft

    215 Maple St, Bennington, VT 05201

    Enjoy the charm and comfort of this beautifully renovated home, ideally nestled in the heart of Bennington. As you arrive, you'll be greeted by a spacious front porch, perfect for relaxation, entertaining, and enjoying cool breezes. This property has undergone a complete transformation from a two-family to a stunning single-family home. It now offers convenient one-floor living. The first floor

    Matt Waddington Hoffman Real Estate

    215 Maple St, Bennington, VT 05201
  • /19

    $219,500

    • 3 Beds
    • 1 Bath
    • 1,254 Sq Ft

    14 Robinson Ave, Bennington, VT 05201

    Discover this lovely three-bedroom, one-bathroom home featuring 1,254 square feet of finished space, all set on a .24-acre lot. Recent upgrades roughly in the last ten years include blown-in insulation, roof, furnace, and updated kitchen and flooring, making this home both comfortable and stylish. Perfect for families or anyone looking for a cozy place. Minutes from Mt. Anthony Country Club,

    Timothy Corcoran Mahar McCarthy Real Estate

    14 Robinson Ave, Bennington, VT 05201
  • /44

    $88,500

    • 5 Beds
    • 1 Bath
    • 1,952 Sq Ft

    273 Union St, Bennington, VT 05201

    This village property has great bones and potential!! First floor includes generously sized kitchen, formal dining room and living room as well as a small office offering the opportunity to expand the full bath to include laundry. The second floor includes four bedrooms including a primary that has a sitting area/dressing room/nursery, whatever suits your needs. Separate barn that while

    Catherine Cairns Maple Leaf Realty

    273 Union St, Bennington, VT 05201
  • /31

    $150,000

    • 3 Beds
    • 1 Bath
    • 1,508 Sq Ft

    109 Evergreen Dr, Bennington, VT 05201

    House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front

    Zachary Zupan EXP Realty

    109 Evergreen Dr, Bennington, VT 05201
  • /42

    $795,000

    • 5 Beds
    • 1.5 Baths
    • 2,450 Sq Ft

    126 Fox Hill Rd, Bennington, VT 05201

    Welcome to this stunning 1850s home, perfectly sited on 2.72 acres with breathtaking mountain views. With 5 bedrooms, 2 full baths, and over three decades of loving ownership, this property offers the perfect blend of historic charm and modern updates in a peaceful, scenic setting.Inside, you'll find spacious, light-filled rooms enhanced by large windows and a calming palette of neutral

    Kelley Mccarthy Mahar McCarthy Real Estate

    126 Fox Hill Rd, Bennington, VT 05201
  • /42

    $1,950,000

    • 9 Beds
    • 7 Baths
    • 6,956 Sq Ft

    1086 West Rd, Bennington, VT 05201

    Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining

    Chris DeFelice Four Seasons Sotheby's Int'l Realty

    1086 West Rd, Bennington, VT 05201
  • /52

    $199,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    130 Morgan St, Bennington, VT 05201

    200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities.

    Dan Mason Perrott Realty

    130 Morgan St, Bennington, VT 05201
  • /30

    $1,250,000

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    77 Fuller Rd W, Bennington, VT 05201

    Experience the quintessential Vermont lifestyle at the historic Nickerson-Jewett farm. Only 5 minutes to Bennington attractions and amenities and 15 minutes to Williamstown, MA. This appealing country home is located on a town maintained dead-end road. Privately nestled on 134.46 acres of scenic beauty, the charming 4 bedroom, 2.5 bath mid nineteenth century farmstead includes a well-preserved

    Jason Saphire www.HomeZu.com

    77 Fuller Rd W, Bennington, VT 05201

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
$260,000
Median Single Family Sale Price
$270,000
Median Townhouse Sale Price
$249,900
Median 2 Bedroom Sale Price
$155,000
Average Price Per Sq Ft
$186
Number of Homes for Sale
18
Last 12 months Home Sales
93
Months of Supply
2.30
Median List Price
$275,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
1%
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