Bennington, VT Homes

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  /20

  $260,000 Sold Jul 14, 2025

  • 1,080 Sq Ft
  • $241/SF
  • 54 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  42 Center St, Bennington, VT 05201

  Charming and cozy 2-Bedroom, 2-Bath Ranch with expansion potential in a quiet, sought-after neighborhood just minutes from downtown and local amenities. With its inviting single-level layout, beautiful hardwood floors, and spacious great room, this home offers comfortable living with timeless appeal.The full walk-out basement adds incredible potential—already partially finished with a

  Faith Rhodes Maple Leaf Realty

  42 Center St, Bennington, VT 05201
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  /32

  Est $312,244 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,776 Sq Ft

  14 Town Line Rd, Bennington, VT 05201

  14 Town Line Rd, Bennington, VT 05201
• 

  

  

  /4

  $199,900

  • 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.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 402-4994

  32-34 Sage St, Bennington, VT 05257
• 

  

  

  /38

  $291,065 Sold Jul 11, 2025

  • 1,736 Sq Ft
  • $168/SF
  • 66 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1946

  121 Fillmore St, Bennington, VT 05201

  Welcome to this newly renovated Cape nestled in a desirable downtown Bennington neighborhood. This spacious home offers four bedrooms and two full bathrooms, including a first floor primary suite for added comfort and convenience.The brand new galley kitchen features gorgeous cabinetry, tile flooring, and energy efficient appliances perfect for modern living. A dedicated dining room

  Brooke Thomson Drew Mahar McCarthy Real Estate

  121 Fillmore St, Bennington, VT 05201
• 

  

  

  /40

  Est $391,840 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,463 Sq Ft

  42 Maple Grove Rd, Bennington, VT 05201

  42 Maple Grove Rd, 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

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 347-6655

  338 Main St, Bennington, VT 05201
• 

  

  /24

  $35,000 Sold Jul 11, 2025

  • Land
  • 7 Acres
  • $4,972 per Acre

  • 100 Days On Market

  170 Gore Rd, Bennington, VT 05201

  7.04 +/- Acres of beautiful open woodland, gently sloping and surrounded by stone walls. A perfect spot for a little get-a-way, camping, tenting, hunting but with future potential for a home. Access is via a deeded 50’ ROW off a paved town road. This ROW is about 800’ long. It would likely be simple to create a parking area and walk or ATV out to the property for recreational purposes. In

  Curtis Trousdale Preferred Properties

  170 Gore Rd, Bennington, VT 05201
• 

  

  /35

  Est $152,667 Not Listed For Sale

  • 3 Beds

  1213 Gore Rd, Bennington, VT 05201

  1213 Gore Rd, Bennington, VT 05201
• 

  

  /34

  $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 porch room, laundry and full bath.

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  374 Overlea Rd, North Bennington, VT 05257
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  /38

  $217,000 Sold Jul 10, 2025

  • 1,416 Sq Ft
  • $153/SF
  • 103 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1940

  130 Beech St, Bennington, VT 05201

  Step into timeless elegance with this charming 1940 American Foursquare home. Many gorgeous features have been preserved from the elegant crystal light fixture to the stunning original woodwork. Each detail speaks to the skilled artisanship of the era. The classic design offers spacious living and a welcoming atmosphere, perfect for both every day life and entertaining. The main floor boasts a

  Justine Curry Maple Leaf Realty

  130 Beech St, Bennington, VT 05201
• 

  

  /34

  Est $256,600 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,809 Sq Ft

  544 Gore Rd, Bennington, VT 05201

  544 Gore Rd, Bennington, VT 05201
• 

  

  /41

  $335,000

  • 3 Beds
  • 1.5 Baths
  • 1,682 Sq Ft

  23 Robinson Ave, Bennington, VT 05201

  Nestled on a quiet street just moments from the golf course, this beautiful two-story brick home offers timeless charm and modern updates. The inviting front porch and lush perennial gardens set the tone for this well-loved property, which also features a fenced-in yard, a small outbuilding, a brand-new shed, and a peaceful backyard water feature. Inside, you'll find 3 bedrooms and 1.5 baths with

  Kelley Mccarthy Mahar McCarthy Real Estate

  23 Robinson Ave, Bennington, VT 05201
• 

  

  /46

  $280,000 Sold Jun 30, 2025

  • 1,875 Sq Ft
  • $149/SF
  • 73 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1950

  4 Pine Rd, Bennington, VT 05201

  Motivated seller of this beautifully ranch home on a dead-end road boasts 4 Bedroom. Enjoy the warmth of the sunroom during the day. The living room centered in the middle of the house has plenty of space to spread out and enjoy the pellet stove insert with a brick hearth on those cool nights. Locally crafted Cushman Style cabinet in the dining area with delightful wood cabinets in the kitchen.

  Dan Mason Perrott Realty

  4 Pine Rd, Bennington, VT 05201
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  /40

  Est $581,912 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,706 Sq Ft

  402 Middle Pownal Rd, Bennington, VT 05201

  402 Middle Pownal Rd, Bennington, VT 05201
• 

  

  /25

  $305,000

  • 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
• 

  

  /22

  $189,000 Sold Jun 27, 2025

  • 900 Sq Ft
  • $210/SF
  • 29 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1949

  38 Arthurs Dr, Bennington, VT 05201

  Welcome to this adorable one-level 3-bedroom, 1-bath bungalow, perfect for comfortable and efficient living. This home offers a cozy and inviting atmosphere with all living spaces on a single level-ideal for anyone seeking ease and accessibility. Inside, enjoy the warmth and character of a woodstove, perfect for creating a cozy ambiance during cooler months while helping keep energy costs low.

  Kelley Mccarthy Mahar McCarthy Real Estate

  38 Arthurs Dr, Bennington, VT 05201
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  /40

  Est $579,354 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,846 Sq Ft

  88 Southshire Dr, Bennington, VT 05201

  88 Southshire Dr, Bennington, VT 05201
• 

  

  /41

  $524,900

  • 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

  Ann Greenwood Alton + Westall Real Estate Agency, LLC

  245 Southshire Dr, Bennington, VT 05201
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  /36

  $265,000 Sold Jun 25, 2025

  • 1,512 Sq Ft
  • $175/SF
  • 57 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1991

  82 Oakes St, Bennington, VT 05201

  Charming Two-Bedroom Home in Convenient Bennington LocationWelcome to this inviting two-bedroom, one full bath home offering spacious and versatile living areas. The main floor features a large living room perfect for relaxing or entertaining, a formal dining room, and an eat-in kitchen with a door leading out to a generous deck-ideal for outdoor gatherings.The lower level boasts

  Kelley Mccarthy Mahar McCarthy Real Estate

  82 Oakes St, Bennington, VT 05201
• 

  

  /40

  Est $577,632 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,483 Sq Ft

  377 Southshire Dr, Bennington, VT 05201

  377 Southshire Dr, Bennington, VT 05201
• 

  

  /47

  $275,000

  • 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
• 

  

  /22

  $43,500 Sold Jun 20, 2025

  • 938 Sq Ft
  • $46/SF
  • 38 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  35 West Rd, Bennington, VT 05201

  Lovingly cared for by a single family since it was built in 1986, this well-maintained single wide is ready to welcome its next chapter—and new owners. Conveniently located just 7 minutes from downtown Bennington and moments from the Monument Arts Center, this home offers both comfort and accessibility. Situated on the first lot in the park, you’ll enjoy stunning mountain views right from the

  Thomas Martins Maple Leaf Realty

  35 West Rd, Bennington, VT 05201
• 

  

  /40

  Est $547,378 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,336 Sq Ft

  179 Southshire Dr, Bennington, VT 05201

  179 Southshire Dr, Bennington, VT 05201
• 

  

  /49

  $325,000 Pending

  • 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
• 

  

  /44

  $315,000 Sold Jun 20, 2025

  • 2,248 Sq Ft
  • $140/SF
  • 38 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1958

  197 Crescent Blvd, Bennington, VT 05201

  Welcome to your ideal in-town residence! This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of space, comfort, and convenience—located just a few blocks from downtown dining, shops and festivals. Step through the enclosed breezeway from your attached garage to find a bright and inviting floor plan featuring a generously sized living room and formal dining room with

  Cassie Barbeau Mahar McCarthy Real Estate

  197 Crescent Blvd, Bennington, VT 05201
• 

  

  /36

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  351 Gore Rd, Bennington, VT 05201

  351 Gore Rd, Bennington, VT 05201
• 

  

  /32

  $335,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft

  169 Bard Rd, Bennington, VT 05201

  Opportunity awaits with this well-built and meticulously maintained 3-bedroom, 2-bath home nestled on a rare and highly desirable 1.84-acre flat lot in the peaceful countryside—just a short drive to town amenities, shops, and schools, this property features town water, a new roof, nearly new boiler and an attached two-car garage. Set back from the road, this property offers space, privacy, and

  Cassie Barbeau Mahar McCarthy Real Estate

  169 Bard Rd, Bennington, VT 05201
• 

  

  /44

  $249,000 Sold Jun 20, 2025

  • 1,366 Sq Ft
  • $182/SF
  • 45 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  16 Browning Place, Bennington, VT 05201

  This home is so new it even has a new address! Was formerly known as 328 School St. and 16 Browning Pl. The renovation took it to the studs and completely renovated. All new wiring with 200 amp electrical panel. It’s even new on the outside of the house. All new insulation and walls. All new vinyl double paned windows with screens. Brand new energy efficient on demand hot water and propane

  Lilli West Maple Leaf Realty

  16 Browning Place, Bennington, VT 05201
• 

  

  /40

  Est $259,710 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,719 Sq Ft

  25 Center St, Bennington, VT 05201

  25 Center St, Bennington, VT 05201
• 

  

  /60

  $275,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft

  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
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  /47

  $160,000 Sold Jun 18, 2025

  • 2,094 Sq Ft
  • $76/SF
  • 39 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1900

  136 Mccall St, Bennington, VT 05201

  Investment opportunity! Three units with strong rental history. Recent renovation of the main foyer with fresh paint and new vinyl plank flooring. The two-story front section features original details including natural woodwork, large windows, and winding staircase. Concrete basement is set up for shared laundry (coin-op washer does not work, new dryer) and all utilities (oil tank, Weil

  Jenifer Prouty Hoffman Hoffman Real Estate

  136 Mccall St, Bennington, VT 05201
• 

  

  /40

  Est $284,916 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,313 Sq Ft

  14 Center St, Bennington, VT 05201

  14 Center St, Bennington, VT 05201
• 

  

  /57

  $250,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft

  153 Spur Rd Unit PVT, Bennington, VT 05201

  Simplify life in this charming one-story home nestled on 2 peaceful acres, offering the perfect blend of privacy and convenience just minutes from town. Thoughtfully designed for comfort and accessibility, this cozy 3-bedroom property features an open-concept kitchen, dining, and living area centered around a classic brick fireplace—ideal for Vermont’s cozy seasons.Enjoy the warmth of a bonus

  Lindsey Martin Maple Leaf Realty

  153 Spur Rd Unit PVT, Bennington, VT 05201
• 

  

  /32

  $322,000 Sold Jun 12, 2025

  • 2,308 Sq Ft
  • $140/SF
  • 253 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1892

  106 Putnam St, Bennington, VT 05201

  Location, location! Just two blocks from the SVMC healthcare campus, this spacious home is ideally situated on Putnam Street in a beloved Village Residential neighborhood. This four-bedroom, three-bath home is currently configured with an in-law suite/apartment on the second floor with exterior access. The permitted second-floor apartment offers versatility with one bathroom and a

  Kristin Comeau TPW Real Estate

  106 Putnam St, Bennington, VT 05201
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  /40

  Est $298,946 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,000 Sq Ft

  38 Center St, Bennington, VT 05201

  38 Center St, Bennington, VT 05201
• 

  

  /37

  $250,000 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,259 Sq Ft

  1236 Morgan St, Bennington, VT 05201

  Charming and solid 1940s Cape with detached 2-car garage. On the outskirts of town with 0.63 acres, this property has a rural vibe, but only 1.2 miles from Main Street... enjoy both the quiet and convenience! Large rear deck overlooks the backyard and is a welcome entryway to the sunny breakfast nook and kitchen. All appliances are staying, including the washer/dryer in the basement. Dining

  Jenifer Prouty Hoffman Hoffman Real Estate

  1236 Morgan St, Bennington, VT 05201
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  /51

  $197,000 Sold Jun 11, 2025

  • 1,876 Sq Ft
  • $105/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  306 Beech St, Bennington, VT 05201

  This lovely, manufactured home sits on .36 acres nestled in quiet area of Bennington. Just a short walk to Main St and where you will find plenty of shopping and dining options. You are just a few steps to the Beech Street field that can be used for outdoor fun and play. Close to South Stream where you will find swimming holes and good fishing. The home sits back off Beech St at the end of a

  Floyd Amidon Maple Leaf Realty

  306 Beech St, Bennington, VT 05201
• 

  

  /18

  Est $253,162 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft

  118 Tel Rd, Bennington, VT 05201

  118 Tel Rd, Bennington, VT 05201
• 

  

  /21

  $299,000 Under Contract

  • 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
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  /34

  $335,000 Sold Jun 09, 2025

  • 2,354 Sq Ft
  • $142/SF
  • 208 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  290 Springhill Rd, Bennington, VT 05201

  Contemporary style 3BR/2BA home in a lovely residential neighborhood not far from downtown Bennington! Kitchen has been updated with granite counters and stainless appliances and opens onto sunny dining area. Living room includes brick hearth with woodstove and shiplap ceiling, there is first floor laundry and a three-quarter bath as well as an expansive family room with lots of natural light.

  Vicki Wilson Maple Leaf Realty

  290 Springhill Rd, Bennington, VT 05201

Showing Results 41 - 80, Page 2 of 18