25

Bennington, VT Houses for Sale

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  • /33

    $279,000

    $20K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,408 Sq Ft

    8 West St, Bennington, VT 05201

    Nestled in the heart of the charming North Bennington community, this lovingly maintained 3 bedroom, 1.5 bath home is ready for its next chapter. Recently refreshed with newly painted interiors, rejuvenated floors, updated electrical, a recently repointed foundation, and repointed chimney, this home blends classic character with thoughtful updates throughout.Enjoy the convenience of first

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    8 West St, Bennington, VT 05201
  • /38

    $299,000

    $26K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,829 Sq Ft

    89 Merson St, Woodford, VT 05201

    Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you’ll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026.What truly sets this property apart is its

    Agent Photo

    Brooke Thomson Drew

    Mahar McCarthy Real Estate

    89 Merson St, Woodford, VT 05201
  • /27

    $209,900

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,075 Sq Ft

    1083 Main St, Bennington, VT 05201

    Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    1083 Main St, Bennington, VT 05201
  • /28

    $209,900

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft

    107 Jefferson Ave, Bennington, VT 05201

    Terrific in town location for this 3 bedroom, 2 bathroom home in Bennington. Offering living room, large kitchen, formal dining room and office/study. Covered porch and patio. Privacy bushes and yard. Property is being sold "as-is".

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    107 Jefferson Ave, Bennington, VT 05201
  • /50

    $150,000

    $10K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,575 Sq Ft

    127 Dewey St, Bennington, VT 05201

    Opportunity awaits with this spacious property offering incredible potential for investors, renovators, or buyers looking to create their dream home. Currently configured as a single family residence, this home features 5 bedrooms and 2 bathrooms. At one point it was a 2 unit home and could potentially be again.Inside, you'll find generous living space ready for your vision and updates. A

    Lindsey Martin Maple Leaf Real Estate

    127 Dewey St, Bennington, VT 05201
  • /52

    $299,000

    • 3 Beds
    • 1.5 Baths
    • 1,411 Sq Ft

    262 Union St, Bennington, VT 05201

    Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out.The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even

    William Paquin Maple Leaf Real Estate

    262 Union St, Bennington, VT 05201
  • /52

    $230,000

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    113 Main St, Bennington, VT 05201

    Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry.Step inside to find gleaming newly upgraded flooring, a warm and inviting

    Lindsey Martin Maple Leaf Real Estate

    113 Main St, Bennington, VT 05201
  • /53

    $205,000

    • 3 Beds
    • 1.5 Baths
    • 1,632 Sq Ft

    305 Weeks St, Bennington, VT 05201

    Experience refined living in this beautifully appointed tri-level townhouse-style condominium, ideally situated just moments from downtown, the hospital, shopping, and dining. Rich in vintage character while thoughtfully updated for modern living, this exceptional residence showcases elegant quartz and butcher block countertops, a designer tile backsplash, and striking marble flooring that create

    Lindsey Martin Maple Leaf Real Estate

    305 Weeks St, Bennington, VT 05201
  • /39

    $260,000

    • 4 Beds
    • 1.5 Baths
    • 1,458 Sq Ft

    301 Elm St, Bennington, VT 05201

    Set on a 0.25-acre corner lot, this classic 4-bedroom home offers the space, character, and friendly atmosphere that make Elm Street so appealing. Sidewalks invite evening strolls and dog walks, neighbors gather on their porches, and it's a favorite destination for trick-or-treaters each Halloween. Next to the Elm Street Market, one block from Southwestern Vermont Medical Center, and close to

    Jenifer Prouty Hoffman Hoffman Real Estate

    301 Elm St, Bennington, VT 05201
  • /37

    $269,900

    $19K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,146 Sq Ft

    109 County St, Bennington, VT 05201

    Welcome to your like-new home in the heart of Bennington! Within easy walking distance of the vibrant downtown district, this beautifully renovated 4-bedroom, 2-bath New Englander has been completely transformed into a truly turnkey property. Nearly every aspect of the home has been updated, allowing you to enjoy the benefits of modern, low-maintenance living from day one.Extensive

    Angela Bevin Maple Leaf Real Estate

    109 County St, Bennington, VT 05201
  • /54

    $480,000

    $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,312 Sq Ft

    498 Townline Rd, Bennington, VT 05201

    If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the

    Betty McEnaney Diamond Realty

    498 Townline Rd, Bennington, VT 05201
  • /45

    $269,000

    $26K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    951 Gage St, Bennington, VT 05201

    This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

    Dan Mason Perrott Realty

    951 Gage St, Bennington, VT 05201
  • /46

    $259,000

    • 2 Beds
    • 1 Bath
    • 1,318 Sq Ft

    104 John St, Bennington, VT 05201

    This well-maintained village home located on a dead end rd is move-in ready and filled with inviting features. Set on a desirable corner lot, the property offers an updated bath, spacious covered front and rear porches, and a cozy pellet stove. The kitchen was just updated as well as painted in side and out. The large front entry provides additional usable space, while the one-car insulated and

    Dan Mason Perrott Realty

    104 John St, Bennington, VT 05201
  • /60

    $695,000

    • 4 Beds
    • 2 Baths
    • 1,614 Sq Ft

    515 Quarry Rd, Bennington, VT 05201

    Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the

    Vicki Wilson Maple Leaf Real Estate

    515 Quarry Rd, Bennington, VT 05201
  • /4

    $80,000

    • 2 Beds
    • 2 Baths
    • 1,465 Sq Ft

    107 Lyons St, Bennington, VT 05201

    Situated on a peaceful dead-end street, this home offers tremendous potential for investors, contractors, or buyers looking to create their dream home. The property features 3 bedrooms, with the possibility of a fourth, along with 2 bathrooms, providing a highly desirable layout and ample living space. With some vision, care, and updates, this home can be transformed into a beautiful residence in

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    107 Lyons St, Bennington, VT 05201
  • /20

    $475,000

    $24K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 9,000 Sq Ft

    425 Main St, Bennington, VT 05201

    15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R

    Chris Long BHG Masiello Brattleboro

    425 Main St, Bennington, VT 05201
  • /43

    $499,900

    $50K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 3,105 Sq Ft

    193 Finley Dr, Bennington, VT 05201

    Set on 3.11 peaceful acres with mountain views and a wonderful sense of privacy, 193 Finley Drive offers the rare combination of one-floor living, generous finished space, and excellent garage capacity in a convenient Bennington location. This 2-bed/3-bath home features a thoughtful main-level layout, with each bedroom offering direct access to a 3/4 bathroom. The primary bath also includes

    Jenifer Prouty Hoffman Hoffman Real Estate

    193 Finley Dr, Bennington, VT 05201
  • /22

    $232,500

    • 3 Beds
    • 2 Baths
    • 1,582 Sq Ft

    903 Gage St, Bennington, VT 05201

    You can make this home your own! With a little TLC, this charming 3 bedroom, 2 bath, Cape has the potential to become the perfect home. Featuring a large, level yard, a two-car, detached garage, with attached outdoor room, mudroom to the kitchen, wood floors, fireplace (condition unknown) and with this central location, it offers endless possibilities. Whether you are looking to renovate,

    Pauline Green

    903 Gage St, Bennington, VT 05201
  • /30

    $595,000

    • 3 Beds
    • 2 Baths
    • 2,379 Sq Ft

    1278 Harrington Rd, Bennington, VT 05201

    Nestled on 16.96 picturesque acres, this spacious 3-4 bedroom, 2 full bath home offers the perfect blend of privacy, comfort, and breathtaking Vermont scenery. Built in 1993, the home features a bright, open-concept great room with expansive windows that capture stunning views of the surrounding landscape. The inviting living area is anchored by a beautiful fireplace, creating a warm and

    Kelley Mccarthy Mahar McCarthy Real Estate

    1278 Harrington Rd, Bennington, VT 05201
  • /37

    $539,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,376 Sq Ft

    811 Middle Pownal Rd, Bennington, VT 05201

    Thoughtfully crafted with a distinctive European-inspired character and beautifully updated throughout, this custom-built 4-bedroom, 3-bath home offers the perfect blend of quality craftsmanship, privacy, and convenience on a picturesque, landscaped lot just minutes from downtown Bennington. The bright and inviting interior features a beautifully renovated kitchen, spacious living areas with

    Jeffrey Dorman

    811 Middle Pownal Rd, Bennington, VT 05201
  • /14

    $104,900

    $20K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 768 Sq Ft

    347 Hickory Rd, Bennington, VT 05201

    Your wait is over—an exceptional opportunity to own in the highly sought-after Woodford Lake Estates! This unique property offers direct access to the beauty of the surrounding Green Mountain National Forest and is ideally located near VAST snowmobile trails, making it a year-round haven for outdoor enthusiasts. Enjoy cross-country skiing just minutes away at Prospect Mountain, along with beach

    William Paquin Maple Leaf Real Estate

    347 Hickory Rd, Bennington, VT 05201
  • /59

    $210,000

    • 5 Beds
    • 2 Baths
    • 2,200 Sq Ft

    118 Foster Dr, Bennington, VT 05201

    Set on over 5.5 acres of private, natural surroundings, this unique split-level ranch with an auxiliary dwelling unit offers an exceptional opportunity for multi-generational living, rental income, or a private guest retreat. Surrounded by peaceful woodlands, the property provides a tranquil rural setting while remaining just a short drive from town amenities.The main residence features three

    Lindsey Martin Maple Leaf Real Estate

    118 Foster Dr, Bennington, VT 05201
  • /33

    $389,900

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 2,098 Sq Ft

    185 Jewett Dr, Bennington, VT 05201

    Welcome home to this 3-bedroom, 2-bath raised ranch nestled on 1.72 beautifully landscaped acres in a peaceful neighborhood. The picturesque property is adorned with a variety of mature fruit trees and offers stunning mountain views. A spacious back deck overlooks the above-ground pool, making it the perfect setting for relaxing, entertaining, or taking in the scenery. Inside, you'll find an

    Julie Glover Mahar McCarthy Real Estate

    185 Jewett Dr, Bennington, VT 05201
  • /28

    $265,000

    • 3 Beds
    • 1.5 Baths
    • 1,688 Sq Ft

    128 Northside Dr, Bennington, VT 05201

    Welcome to this 3 bedroom, 1.5-bath Cape style home located in a planned commercial zone. Offering 1,688 square feet of well-designed living space on a manageable 0.26-acre lot, this inviting residence is perfect for comfortable family living. Offers beautiful hardwood floors gracing the upstairs bedrooms, as well as the spacious living and dining rooms—ideal for gathering with loved ones. The

    Timothy Corcoran Mahar McCarthy Real Estate

    128 Northside Dr, Bennington, VT 05201
  • /36

    $359,000

    $40K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,938 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 Real Estate

    100 McCarthy Acres, North 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.

Single Family Home Price Trends

Median Home Price
$285,000
Median 3-Bedroom Home Price
$279,000
Median 4-Bedroom Home Price
$350,000
Median 5-Bedroom Home Price
$405,000
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