Bennington, VT Homes

• 

  

  

  /47

  $240,000 Sold Sep 24, 2025

  • 2,404 Sq Ft
  • $100/SF
  • 114 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1895

  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
• 

  

  

  /40

  Est $314,841 Not Listed For Sale

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

  38 Center St, Bennington, VT 05201

  38 Center St, Bennington, VT 05201
• 

  

  

  /21

  $120,000

  • Land
  • 20 Acres
  • $6,000 per Acre

  1319 Vail Rd, Bennington, VT 05201

  Discover an exceptional opportunity to build your dream home on this prime 20-acre parcel located in the desirable west end of Bennington. This expansive property offers a perfect blend of privacy and convenience, ready for immediate development.Key features of this remarkable land include an established driveway providing easy access to your future homesite, and a completed perk test

  Lilli West Maple Leaf Realty

  1319 Vail Rd, Bennington, VT 05201
• 

  

  

  /20

  $89,499 Sold Sep 24, 2025

  • 825 Sq Ft
  • $108/SF
  • 120 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2024

  72 Ethans Way, Bennington, VT 05201

  Welcome to 72 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Lewis model manufactured home offers 2 bedrooms, 2 bathroom, and 825 sq. ft. (16 x 56 ft.) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  72 Ethans Way, Bennington, VT 05201
• 

  

  

  /38

  Est $286,251 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,662 Sq Ft

  116 Rutter Rd, Bennington, VT 05201

  116 Rutter Rd, 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
• 

  

  /56

  $385,000 Sold Sep 23, 2025

  • 1,702 Sq Ft
  • $226/SF
  • 156 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  321 Chester Knoll Dr, Bennington, VT 05201

  Low maintenance lifestyle awaits~This new construction three bedroom two bath cape style home is energy efficient and up to the newest Vermont energy codes. On demand hot water and energy efficient heat system. Not only do you get brand new construction, but you have an option for one level living with living room, kitchen, dining, laundry, bedroom, and full bath all on one level. Upstairs has

  Lilli West Maple Leaf Realty

  321 Chester Knoll Dr, Bennington, VT 05201
• 

  

  /26

  Est $263,936 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,760 Sq Ft

  107 Rutter Rd, Bennington, VT 05201

  107 Rutter Rd, Bennington, VT 05201
• 

  

  /26

  $199,900

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

  215 Maple St, Bennington, VT 05201

  Huge Price Reduction. 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

  Matt Waddington Hoffman Real Estate

  215 Maple St, Bennington, VT 05201
• 

  

  /60

  $245,000 Sold Sep 22, 2025

  • 1,320 Sq Ft
  • $186/SF
  • 3 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1954

  19 Robinson Ave, Bennington, VT 05201

  This charming 3-bedroom, 1 bathroom ranch features one-level living. The updated gallery-style eat-in kitchen offers plenty of space and storage and leads into a spacious living room where you'll enjoy a large bay window and fireplace. Enjoy the beautiful hardwood floors throughout the bedrooms and hallways, which lead into a newly renovated full bath. There's a full basement which offers options

  Floyd Amidon Maple Leaf Realty

  19 Robinson Ave, Bennington, VT 05201
• 

  

  /38

  Est $223,407 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  5 Tel Rd, Bennington, VT 05201

  5 Tel Rd, Bennington, VT 05201
• 

  

  /8

  $59,000

  • Land
  • 0.29 Acre
  • $203,448 per Acre

  420 Burgess Rd, Bennington, VT 05201

  Level building lot with town sewer and water at the edge of town.Possible owner financing.

  Dan Mason Perrott Realty

  420 Burgess Rd, Bennington, VT 05201
• 

  

  /53

  $400,000 Sold Sep 22, 2025

  • 1,309 Sq Ft
  • $306/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  495 Fairview St, Bennington, VT 05201

  This charming cape style home is close to town yet enjoys a sense of rural privacy. There is an open floor plan for entertaining on the first floor as well as two bedrooms and a bath. The wood stove keeps you cozy on those cold winter evenings. The second floor is a primary suite with large bath including a claw foot soaking tub and walk-in closet. Access to the full basement via the

  Catherine Cairns Maple Leaf Realty

  495 Fairview St, Bennington, VT 05201
• 

  

  /26

  Est $312,784 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  1 Tel Cir, Bennington, VT 05201

  1 Tel Cir, 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

  $355,000 Sold Sep 19, 2025

  • 2,072 Sq Ft
  • $171/SF
  • 22 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1948

  60 Knoll Crest Ln, Bennington, VT 05201

  Step into this well maintained brick and clapboard residence, perfectly nestled in a lovely neighborhood. Just minutes from the hospital and a short, pleasant walk to downtown, this home offers the best of both convenience and community.Bathed in natural light, the interior boasts an inviting and functional layout highlighted by gleaming hardwood floors and timeless character throughout.

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  60 Knoll Crest Ln, Bennington, VT 05201
• 

  

  /40

  Est $238,871 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  316 Beech St, Bennington, VT 05201

  316 Beech St, 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
• 

  

  /25

  $101,968 Sold Sep 19, 2025

  • 825 Sq Ft
  • $124/SF
  • 125 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2024

  86 Ethans Way Unit Lot 86E, Bennington, VT 05201

  Welcome to 78 86 Ethans Way, Lot 86E Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Polo model manufactured home offers 2 bedrooms, 2 bathrooms, and 825 sq. ft. of thoughtfully designed living space.Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  86 Ethans Way Unit Lot 86E, Bennington, VT 05201
• 

  

  /17

  Est $163,650 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,709 Sq Ft

  224 Beech St, Bennington, VT 05201

  224 Beech St, Bennington, VT 05201
• 

  

  /17

  $145,000

  • 2 Beds
  • 1.5 Baths
  • 852 Sq Ft

  432 South St Unit C6, Bennington, VT 05201

  A fresh perspective on easy living! Welcome to this beautifully maintained 2BR/1.5 BA second-floor condo in Nathanial Court offering the perfect blend of comfort, convenience, and low-maintenance living. Step into a bright and airy open floor plan, where large windows flood the space with natural light. The tidy kitchen boasts ample cabinet space, sleek stainless steel appliances, and a clean

  Angela Bevin Maple Leaf Realty

  432 South St Unit C6, Bennington, VT 05201
• 

  

  /57

  $190,000 Sold Sep 16, 2025

  • 1,416 Sq Ft
  • $134/SF
  • 75 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1943

  100 Webb St, Bennington, VT 05201

  Enchanted Historic Home with Storybook Charm – A Hidden Gem Near Downtown!Step into a fairytale in this one-of-a-kind, lovingly maintained home — a true magical retreat nestled just minutes from downtown. Owned and cherished by the same family since 1951, this architectural treasure blends old-world artistry with everyday comfort.From the moment you arrive, you're greeted by the

  Lindsey Martin Maple Leaf Realty

  100 Webb St, Bennington, VT 05201
• 

  

  /35

  Est $197,089 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,680 Sq Ft

  218 Beech St, Bennington, VT 05201

  218 Beech St, Bennington, VT 05201
• 

  

  /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.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  755 Main St, Bennington, VT 05201
• 

  

  /35

  $220,000 Sold Sep 16, 2025

  • 1,554 Sq Ft
  • $142/SF
  • 83 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1930

  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
• 

  

  /40

  Est $236,191 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  313 Beech St, Bennington, VT 05201

  313 Beech 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
• 

  

  /37

  $255,000 Sold Sep 12, 2025

  • 2,288 Sq Ft
  • $111/SF
  • 12 Days On Market

  • 6 Beds
  • 2 Baths
  • Built 1920

  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

  215 Dewey St, Bennington, VT 05201
• 

  

  /40

  Est $161,939 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 989 Sq Ft

  239 Beech St, Bennington, VT 05201

  239 Beech 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
• 

  

  /23

  $89,499 Sold Sep 11, 2025

  • 746 Sq Ft
  • $120/SF
  • 90 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2024

  92 Ethans Way, Bennington, VT 05201

  Welcome to 92 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Polo model manufactured home offers 2 bedrooms, 1 bathroom, and 746 sq. ft. (14 x 56 ft.) of thoughtfully designed living space.Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  92 Ethans Way, Bennington, VT 05201
• 

  

  /37

  Est $330,814 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,714 Sq Ft

  163 Morgan St, Bennington, VT 05201

  163 Morgan 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
• 

  

  /54

  $225,000 Sold Sep 10, 2025

  • 2,162 Sq Ft
  • $104/SF
  • 15 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1890

  304 North St Unit 6, Bennington, VT 05201

  Great Investment Opportunity! This well-maintained 3-unit property is a fantastic opportunity for savvy investors. Two of the units are currently rented, providing immediate income potential. Situated just a short stroll from downtown, you'll find charming shops, popular restaurants, and close proximity to the Bennington trail system—perfect for outdoor enthusiasts. Just 1 hour from Albany and

  Thomas Martins Maple Leaf Realty

  304 North St Unit 6, Bennington, VT 05201
• 

  

  /30

  Est $205,828 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,603 Sq Ft

  101 Coulter St, Bennington, VT 05201

  101 Coulter St, Bennington, VT 05201
• 

  

  /10

  $1,950,000

  • Land
  • 7 Acres
  • $278,571 per Acre

  720 N Branch St, Bennington, VT 05201

  Discover the potential at 720 & 702 North Branch Street—a rare 7-acre offering in a prime Bennington location. With level land, generous frontage, and easy access, this property is perfectly positioned for residential or mixed-use development, with municipal water and sewer available at the street.The sale includes a well-maintained duplex at 702 North Branch, featuring a 3-bedroom unit

  Paul Carroccio TPW Real Estate

  720 N Branch St, Bennington, VT 05201
• 

  

  /26

  $265,000 Sold Sep 09, 2025

  • 1,576 Sq Ft
  • $168/SF
  • 55 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1930

  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
• 

  

  /6

  Est $334,854 Not Listed For Sale

  • 3 Beds

  240 Grandview St, Bennington, VT 05201

  240 Grandview St, Bennington, VT 05201
• 

  

  /31

  $135,000

  • 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
• 

  

  /34

  $90,000 Sold Sep 08, 2025

  • 1,366 Sq Ft
  • $66/SF
  • 5 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  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

Showing Results 81 - 120, Page 3 of 18