Bennington, VT Homes

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  /20

  $139,000 Pending

  • 1 Bed
  • 704 Sq Ft

  5412, Bennington, VT 05201

  Escape to your own private retreat on the side of Mount Anthony! This classic A-frame camp sits on 25 acres of secluded land, offering the perfect setting for hunting, outdoor adventure, or a peaceful off-grid getaway. Accessed by a gated, well-maintained gravel road, the property provides both privacy and convenience—tucked away in nature yet only about 10 minutes to downtown Bennington. While

  Jeffrey Dorman

  5412, Bennington, VT 05201
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  /26

  $193,500 Sold Aug 06, 2025

  • 1,632 Sq Ft
  • $119/SF
  • 17 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1937

  305 Weeks St, Bennington, VT 05201

  Located in a sought-after area, this Tri-level townhouse style condo is situated close to Main Street shops, bars, and restaurants, as well as the hospital, rec center, neighborhood markets, and the bus station. The first floor boasts an open floor plan with a unique kitchen that retains its original charm. Highlights include a center brick chimney, island w/ breakfast bar, quartz and butcher

  Matt Waddington Hoffman Real Estate

  305 Weeks St, Bennington, VT 05201
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  /30

  Est $215,589 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,114 Sq Ft

  110 Booth Terrace, Bennington, VT 05201

  110 Booth Terrace, Bennington, VT 05201
• 

  

  

  /28

  $265,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft

  26 Cyr Ct, Bennington, VT 05201

  Cute as a button! This charming one-owner home is the perfect opportunity for a first-time homebuyer or for those looking to downsize! The main level features a welcoming layout with bright living spaces and plenty of natural light. The eat-in kitchen flows seamlessly into the living area. There are two spacious bedrooms, lots of closet space and a full bathroom. The basement level features a

  Cassie Barbeau Mahar McCarthy Real Estate

  26 Cyr Ct, Bennington, VT 05201
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  /14

  $278,000 Sold Aug 04, 2025

  • 1,461 Sq Ft
  • $190/SF
  • 38 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1825

  400 South St, Bennington, VT 05201

  400 South St. is a Very well-maintained 3-unit multi-family home, offering 1-bedroom units, ample natural light from skylights, and off street parking. Unit 3 comes fully furnished. All units have access to an owner supplied washer/dryer room in the thoughtfully designed basement containing designated storage areas for each unit. The property has a great rental history and generates good income,

  William Paquin Maple Leaf Realty

  400 South St, Bennington, VT 05201
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  /30

  Est $319,701 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,056 Sq Ft

  233 Grandview St, Bennington, VT 05201

  233 Grandview St, Bennington, VT 05201
• 

  

  /21

  $185,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 880 Sq Ft

  2591 Chapel Rd, Bennington, VT 05201

  Lovely ranch home with 2 bedrooms on a great level lot. Come see all the improvements including but not limited to, new flooring, new kitchen counter, new stove, new dishwasher, fresh paint throughout, new boiler, new oil tank, and new light fixtures. Come see what else this home has to offer.

  Susan Bellville Bellville Realty

  2591 Chapel Rd, Bennington, VT 05201
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  /37

  $233,000 Sold Aug 04, 2025

  • 1,056 Sq Ft
  • $221/SF
  • 73 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1984

  73 Woodford City Rd, Bennington, VT 05201

  Step into your woodland paradise! Nestled on 1.1 acres and bordered by a babbling brook and private pond, this lovingly maintained 3-bedroom, 1-bath home offers peace, privacy, and a strong connection to nature. Built by the current owner in 1982, the home has been well cared for over the years.A detached two-car garage with workshop space and a separate shed offer plenty of room for tools,

  Abi Gregorio

  73 Woodford City Rd, Bennington, VT 05201
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  /33

  Est $137,837 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 840 Sq Ft

  105 Booth Terrace, Bennington, VT 05201

  105 Booth Terrace, Bennington, VT 05201
• 

  

  /43

  $239,900 Under Contract

  • 6 Beds
  • 2 Baths
  • 2,400 Sq Ft

  110 S Branch St, Bennington, VT 05201

  Tucked away from the road and surrounded by nature, this inviting duplex in Bennington offers the perfect blend of privacy, charm, and convenience. Whether you're looking for a smart investment or a place to call home while earning rental income, this property is a must-see! Each spacious unit features 3 comfortable bedrooms, an updated full bath, bright living and dining rooms, and a classic

  Jenifer Prouty Hoffman Hoffman Real Estate

  110 S Branch St, Bennington, VT 05201
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  /21

  $73,500 Sold Aug 04, 2025

  • Land
  • 7 Acres
  • $10,500 per Acre

  • 297 Days On Market

  0 Sunset Dr Unit 5005504, Bennington, VT 05201

  One of the best building lots available in Bennington country now available for sale. Close to Bennington, but country setting and bordering hundreds of acres of conserved land this is a wildlife enthusiasts dream location. While there for photos a large bear came to visit! Beautiful deer are often seen roaming as well as turkeys and other birds. The back side of the lot borders the open wetlands

  Lilli West Maple Leaf Realty

  0 Sunset Dr Unit 5005504, Bennington, VT 05201
• 

  

  /40

  Est $276,183 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft

  100 Booth Terrace, Bennington, VT 05201

  100 Booth Terrace, Bennington, VT 05201
• 

  

  /27

  $279,000 Under Contract

  • 9 Beds
  • 3 Baths
  • 3,176 Sq Ft

  26 Sage St, Bennington, VT 05257

  A wonderful investment opportunity in the desirable village of North Bennington! This income-producing property with three units has been well kept and updated over the years - most recently with a brand new roof. Two of the three-bedroom units have been freshly renovated and all are currently occupied with a strong rental history. Two of the units have two stories, giving it a townhouse feel,

  Lilli West Maple Leaf Realty

  26 Sage St, Bennington, VT 05257
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  /39

  $275,000 Sold Jul 31, 2025

  • 1,608 Sq Ft
  • $171/SF
  • 69 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1971

  30 Harbour Rd, Bennington, VT 05201

  Welcome to the charming ranch home nestled in a desirable and quiet neighborhood! This beautifully maintained three bedroom home offers comfort, style, and fantastic features throughout. The recently renovated full bathroom is a true highlight, featuring a stunning fully tiled walk in shower complete with a built in bench.Enjoy the comfort and efficiency of a brand new mini split, and

  Brooke Thomson Drew Mahar McCarthy Real Estate

  30 Harbour Rd, Bennington, VT 05201
• 

  

  /23

  Est $233,140 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,574 Sq Ft

  101 Barber St, Bennington, VT 05201

  101 Barber St, Bennington, VT 05201
• 

  

  /14

  $96,906 Under Contract

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  24 Cassie Ln, Bennington, VT 05201

  Welcome to 24 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) 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

  24 Cassie Ln, Bennington, VT 05201
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  /39

  $383,000 Sold Jul 30, 2025

  • 2,207 Sq Ft
  • $174/SF
  • 61 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2003

  224 Garbrooke Dr, Bennington, VT 05201

  Charming Southern Vermont Retreat with Modern Comforts!Welcome to this beautifully maintained 4-bedroom, 3-bathroom home nestled in one of Southern Vermont’s desirable neighborhoods. Located near the end of a quiet dead-end drive, this semi-secluded property offers peace, privacy, and a warm sense of community.Step onto the inviting covered front porch, perfect for relaxing with

  Lindsey Martin Maple Leaf Realty

  224 Garbrooke Dr, Bennington, VT 05201
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  /30

  Est $258,775 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,092 Sq Ft

  228 Grandview St, Bennington, VT 05201

  228 Grandview St, Bennington, VT 05201
• 

  

  /42

  $795,000 Under Contract

  • 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
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  /46

  $399,000 Sold Jul 28, 2025

  • 1,728 Sq Ft
  • $231/SF
  • 55 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1930

  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
• 

  

  /32

  Est $321,056 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,466 Sq Ft

  214 Silver St, Bennington, VT 05201

  214 Silver St, Bennington, VT 05201
• 

  

  /19

  $89,499 Under Contract

  • 2 Beds
  • 1 Bath
  • 746 Sq Ft

  64 Ethans Way, Bennington, VT 05201

  Welcome to 64 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 energy-efficient

  Kate Barry EXP Realty

  64 Ethans Way, Bennington, VT 05201
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  /40

  $185,000 Sold Jul 25, 2025

  • 800 Sq Ft
  • $231/SF
  • 28 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2016

  305 Grove St, Bennington, VT 05201

  Cost of living got you down? It's time for a change! This nice little home on a dead-end street was completely rebuilt in 2016, so it's like new and ready for you to move right in. Heating is efficient as it was well-insulated during the renovation and includes an updated eco thermostat. Gorgeous floors throughout and large rooms give it an open feel. The primary bedroom has ample closet space

  Justine Curry Maple Leaf Realty

  305 Grove St, Bennington, VT 05201
• 

  

  /31

  Est $287,611 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,840 Sq Ft

  325 Silver St, Bennington, VT 05201

  325 Silver St, Bennington, VT 05201
• 

  

  /26

  $74,900 Pending

  • 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
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  /30

  $310,000 Sold Jul 25, 2025

  • 2,032 Sq Ft
  • $153/SF
  • 54 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1930

  198 Weeks St, Bennington, VT 05201

  Step into this beautiful 1930s classic home, filled with character and endless possibilities. This home offers three bedrooms, one bathroom, and a layout that seamlessly combines classic details with comfortable living spaces. The heart of the home is the large dining area, perfect for hosting gatherings or enjoying quiet family meals. Adjacent, you will find a spacious living room with a

  Margretta Fischer Wohler Realty Group

  198 Weeks St, Bennington, VT 05201
• 

  

  /13

  Est $149,858 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 819 Sq Ft

  432 South St Unit C11, Bennington, VT 05201

  432 South St Unit C11, Bennington, VT 05201
• 

  

  /12

  $37,100

  • 2 Beds
  • 1 Bath
  • 1,302 Sq Ft

  933 East Rd, Bennington, VT 05201

  Built in 1965, this one level home offers approximately 1302 finished square feet, two bedrooms and one full bath, fireplace, unfinished basement and deck. This home sits on an approximate 44867 sqft lot. This property is in uninhabitable condition and boarded up. UNSAFE TO ENTER, foundation cracked, fallen and caved in.

  Sherry Price REALHome Services and Solutions, Inc.

  933 East Rd, Bennington, VT 05201
• 

  

  /49

  $313,000 Sold Jul 21, 2025

  • 2,050 Sq Ft
  • $153/SF
  • 53 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1910

  1385 N Bennington Rd, North Bennington, VT 05257

  Step into timeless charm with this beautifully maintained 1910 antique home offering 4 bedrooms and 2 full baths on a nearly a full acre. Enjoy the perfect blend of historic character and modern updates, including a great working kitchen that any chef would enjoy, plenty of counter space, efficient layout, and everything within easy reach, perfect for creating homemade meals. The original

  Brooke Thomson Drew Mahar McCarthy Real Estate

  1385 N Bennington Rd, North Bennington, VT 05257
• 

  

  /11

  Est $148,230 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 948 Sq Ft

  432 South St Unit C5, Bennington, VT 05201

  432 South St Unit C5, Bennington, VT 05201
• 

  

  /24

  $279,900

  • 5 Beds
  • 3 Baths
  • 3,164 Sq Ft

  2288 East Rd, Bennington, VT 05201

  Great investment opportunity! This 3 Unit building consists of one, one bedroom unit and two, two bedroom units. The possibilities and flexibility are a real upside. With minimal work the units will be ready to rent out and you'll be able to select your own tenants. One heating system so owner is responsible for heat in it's current configuration. The large lot has potential for additional

  William Paquin Maple Leaf Realty

  2288 East Rd, Bennington, VT 05201
• 

  

  /31

  $701,000 Sold Jul 21, 2025

  • 2,222 Sq Ft
  • $315/SF
  • 25 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1984

  762 Houran Rd, Bennington, VT 05201

  Experience history and live your dream in a revolutionary town! Step into a home where history and modern luxury blend seamlessly . Located in the town where Ethan Allen and the Green Mountain Boys made their mark, and where Robert Frost found inspiration for his timeless poetry, this property offers more than just a place to live - it's a place to dream. Enjoy panoramic mountain views from the

  Adrienne Sherwood Four Seasons Sotheby's Int'l Realty

  762 Houran Rd, Bennington, VT 05201
• 

  

  /36

  Est $163,610 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 948 Sq Ft

  432 South St Unit B5, Bennington, VT 05201

  432 South St Unit B5, Bennington, VT 05201
• 

  

  /60

  $230,500 Sold Jul 18, 2025

  • 2,004 Sq Ft
  • $115/SF
  • 62 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1958

  322 Burgess Rd, Bennington, VT 05201

  2BR/2BA Mid Century Modern brick ranch is solidly built and cozy! Step into the large living room with hardwood floors and electric fireplace. Eat-in kitchen is bright and nostalgic with corner windows and sink and period appropriate cabinetry. Arched doorways lead throughout the home to the two bedrooms and the full bath with soaking tub. On the lower level, there is a carpeted family room

  Vicki Wilson Maple Leaf Realty

  322 Burgess Rd, Bennington, VT 05201
• 

  

  /19

  Est $151,840 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 852 Sq Ft

  432 South St Unit A12, Bennington, VT 05201

  432 South St Unit A12, Bennington, VT 05201
• 

  

  /15

  $175,000 Sold Jul 17, 2025

  • 592 Sq Ft
  • $296/SF
  • 20 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  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.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  121 Mccall St, Bennington, VT 05201
• 

  

  /19

  Est $147,098 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 819 Sq Ft

  432 South St Unit A5, Bennington, VT 05201

  432 South St Unit A5, Bennington, VT 05201
• 

  

  /30

  $290,000 Sold Jul 17, 2025

  • 1,042 Sq Ft
  • $278/SF
  • 75 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1948

  221 Grandview St, Bennington, VT 05201

  Charming renovated cape with mountain views! Perched high on Grandview Street on a spacious and level lot, this beautifully renovated Cape-style home offers comfort, style, and lovely views of Mount Anthony and beyond. Step inside to a bright and welcoming first floor, where an open-concept layout easily accommodates both living and dining areas, enhanced by large windows that fill the space with

  Angela Bevin Maple Leaf Realty

  221 Grandview St, Bennington, VT 05201
• 

  

  /32

  Est $226,255 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,262 Sq Ft

  402 South St, Bennington, VT 05201

  402 South St, Bennington, VT 05201
• 

  

  /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

Showing Results 161 - 200, Page 5 of 18