23

Bennington, VT Houses for Sale

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  • /15

    $169,900

    • 2 Beds
    • 1 Bath
    • 592 Sq Ft

    121 Mccall St, Bennington, VT 05201

    Cute and cozy 2 bedroom bungalow in Bennington. Completely redone and super efficient. Are you ready for low maintenance and easy living? This is it. Small yard with potential garden space. Short walk to town and more.

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 622-2339

    121 Mccall St, Bennington, VT 05201
  • /41

    $320,000

    • 5 Beds
    • 2 Baths
    • 2,418 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

    $185,000

    • 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
  • /20

    $750,000

    • 4 Beds
    • 5 Baths
    • 6,650 Sq Ft

    338 Main St, Bennington, VT 05201

    Don't miss your opportunity to own one of the area's most prestigious properties. The "Marble Bank" is located at the intersection of US Route 7 and Vermont Route 9 and is currently the landmark Fiddlehead Gallery. This property offers unique and grand architecture to go along with its high visibility location. Downtown's redevelopment and thriving new businesses make this location even more

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 347-6655

    338 Main St, Bennington, VT 05201
  • /47

    $399,000

    • 5 Beds
    • 3.5 Baths
    • 3,600 Sq Ft

    46 Duffy Dr, Bennington, VT 05201

    This spacious 5-bedroom, 4-bath Colonial in Bennington's sought-after Maplewood neighborhood offers over 3,600 sq ft of flexible living space, including a finished walk-out in-law suite with full kitchen and private entry. Thoughtfully updated with granite counters, stainless steel appliances, and a smart home system including ADT security, glass break sensors, and a smart thermostat. The vaulted

    Nick Sicard EXP Realty

    46 Duffy Dr, Bennington, VT 05201
  • /41

    $524,900 Open Sun 2PM - 4PM

    • 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

    Ann Greenwood Alton + Westall Real Estate Agency, LLC

    245 Southshire Dr, Bennington, VT 05201
  • /21

    $299,000

    • 3 Beds
    • 1.5 Baths
    • 1,365 Sq Ft

    339 Chester Knoll Dr, Bennington, VT 05201

    A completely renovated gem in a fantastic location awaits its new owner. This beautifully restored cape-style home in Bennington's desirable Chester Knoll community offers a stunning and worry-free living experience. Adhering to the newest Vermont energy codes, this energy-efficient home boasts an Energy Star propane heating system for optimal comfort and savings.Chester Knoll provides an

    Lori Hurley Four Corner Properties LLC

    339 Chester Knoll Dr, Bennington, VT 05201
  • /26

    $289,900

    • 3 Beds
    • 1.5 Baths
    • 1,576 Sq Ft

    519 South St, Bennington, VT 05201

    Welcome to this beautifully maintained 3-bedroom, 1.25-bath home nestled on a corner lot in Bennington. This inviting property blends classic charm with thoughtful updates, offering comfort and style both inside and out.Step into the spacious kitchen featuring stunning wood cabinetry, granite countertops, and a functional island with a bar sink-perfect for entertaining or everyday living. The

    Kelley Mccarthy Mahar McCarthy Real Estate

    519 South St, Bennington, VT 05201
  • /46

    $425,000

    • 3 Beds
    • 3 Baths
    • 1,728 Sq Ft

    4 Bank St, Bennington, VT 05201

    Across from the 5th Fairway of the Mount Anthony Country Club you’ll find this charming, meticulously maintained 3 bedroom 2 bath home. The spacious open layout, custom kitchen, and expansive deck are warm and inviting. Relax on your front porch and enjoy the scenic mountain vistas of Mount Anthony and the Bennington Monument. Fabulous, convenient location! The home began as a bungalow, the

    Margretta Fischer Wohler Realty Group

    4 Bank St, Bennington, VT 05201
  • /55

    $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
  • /35

    $264,900

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft

    115 Jefferson Ave, Bennington, VT 05201

    Located in a charming Bennington neighborhood, this home offers both convenience and comfort, with shopping, schools, the post office, and the hospital just a short distance away. The welcoming three-season front porch is perfect for enjoying your morning coffee or winding down after a long day. Inside, the spacious, eat-in kitchen has brand-new flooring and newer appliances, adding a fresh and

    Kelley Mccarthy Mahar McCarthy Real Estate

    115 Jefferson Ave, Bennington, VT 05201
  • /47

    $299,900

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft

    120 Imperial Ave, Bennington, VT 05201

    Nestled in the charming village of Bennington, Vermont, this stately 4-bedroom, 2.5-bath home blends timeless elegance with thoughtful updates. Built in 1895 and set on 0.41 acres, the property offers a rare combination of historic character and modern livability. A large Trex front deck with handicap accessible ramp to the front and kitchen doors welcomes you to the home, where you'll find

    Kelley Mccarthy Mahar McCarthy Real Estate

    120 Imperial Ave, Bennington, VT 05201
  • /12

    $575,000

    • 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
  • /37

    $239,900

    • 6 Beds
    • 2 Baths
    • 2,288 Sq Ft

    215 Dewey St, Bennington, VT 05201

    Beautifully situated in the heart of Bennington, this spacious and sunlit 2,288 sq ft duplex (1,144 sq ft per unit) is the perfect blend of comfort, character, and income potential. Each unit features three generous bedrooms, one full bath, in-unit laundry, and charming hardwood floors in the main living areas. An abundance of windows fills the space with natural light, creating a bright and

    Jeffrey Dorman EXP Realty

    215 Dewey St, Bennington, VT 05201
  • /34

    $110,000

    • 3 Beds
    • 1 Bath
    • 1,366 Sq Ft

    40 Washing Brook Rd, Bennington, VT 05201

    This property offers a secluded retreat with stunning mountain views and the South Stream flowing through it. Bordered by wetlands and woods, it provides a sense of being truly "away from it all."While the house requires significant work, making it an ideal candidate for a cash or rehab loan, it presents a fantastic opportunity for transformation. The living room features a beautiful

    Lilli West Maple Leaf Realty

    40 Washing Brook Rd, Bennington, VT 05201
  • /44

    $100,000

    • 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
  • /22

    $139,000

    • 4 Beds
    • 1 Bath
    • 1,262 Sq Ft

    101 Morgan St, Bennington, VT 05201

    Motivated seller.!!! Move in asd add your finishing touches to this Antique House located in Downtown on a generous corner. This 2 story, 4 bedroom, 1 bath Bennington home has great character featuring a Dutch front door, enclosed front porch, and beautiful bay window. Property has an eat-in kitchen, dinning room, laundry room with washer and dryer, living room, basement, and den! Enjoy being

    Dan Mason Perrott Realty

    101 Morgan St, 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
  • /26

    $79,900

    • 4 Beds
    • 1.5 Baths
    • 1,887 Sq Ft

    115 River St, Bennington, VT 05201

    Charming Home with River Views & Tons of PotentialThere’s so much potential waiting to be unlocked in this spacious 4-bedroom, 1.5-bath home! With a classic layout that includes a dining room, fireplaced living room, and a cozy den, there’s room for everyone to spread out and make it their own.A large covered front porch invites you to relax and take in the neighborhood charm,

    Linda Benoit Highland Realty

    115 River St, Bennington, VT 05201

Why Live in Bennington

Bennington, located in the Green Mountains of southwestern Vermont, is a town rich in history and natural beauty. Known as the first town chartered in Vermont, it offers a glimpse into the past with attractions like the Old Bennington Historic District, the Bennington Monument, and the Old First Church Cemetery. Downtown Bennington is evolving with investments in 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 to more rural settings in Shaftsbury and Arlington, surrounded by rolling hills and family farms. Residents enjoy outdoor activities year-round, with skiing at Prospect Mountain Ski Area just 8 miles east and hiking trails that inspired poet Robert Frost. Main Street features historic buildings housing diverse restaurants, shops, and cozy pubs, while grocery needs are met by local markets and larger stores like Aldi and Walmart. Although local schools have mixed ratings, Bennington College offers higher education opportunities with a focus on arts and internships. The town is conveniently located 25 miles south of Manchester and near state borders, providing easy access to Albany and Springfield. Crime rates have decreased, making Bennington safer than the national average.

Home Trends in Bennington, VT

Housing Trends

Median Sale Price
$265,000
Median Single Family Sale Price
$270,000
Median Townhouse Sale Price
$239,900
Median 2 Bedroom Sale Price
$148,000
Average Price Per Sq Ft
$174
Number of Homes for Sale
23
Last 12 months Home Sales
100
Months of Supply
2.80
Median List Price
$275,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
10%
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