Bennington, VT Homes

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  /49

  $315,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,050 Sq Ft

  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

  (802) 520-1223

  1385 N Bennington Rd, North Bennington, VT 05257
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• 

  

  /2

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • House for Rent

  165 Benmont Ave, Bennington, VT 05201

  Property Id: 1488761I bed 1 bath small house.The tenants pay their own utilities:heat electric etc…

  165 Benmont 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
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  /13

  Est $62,485 Not Listed For Sale

  231 Chapel Rd, Bennington, VT 05201

  231 Chapel Rd, Bennington, VT 05201
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  /60

  $239,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 2,004 Sq Ft

  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

  (802) 771-2949

  322 Burgess Rd, Bennington, VT 05201
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  /18

  $1,175 per month

  • Studio-1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  201 Division St Unit 203, Bennington, VT 05201

  201 Division St Unit 203, Bennington, VT 05201
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  /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
• 

  

  /27

  Est $192,483 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,155 Sq Ft

  731 Main St, Bennington, VT 05201

  731 Main St, Bennington, VT 05201
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  /38

  $289,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,736 Sq Ft

  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 provides a

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 392-9256

  121 Fillmore St, Bennington, VT 05201
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  /10

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  130 Union St Unit D, Bennington, VT 05201

  This 1-bedroom, 1-bathroom apartment located within the downtown of Bennington offers 700 square feet of living space. The living room features ample natural light and connects directly to the kitchen, which includes essential appliances. The bedroom provides sufficient space for a queen-sized bed and includes plenty of closet space for storage. The bathroom is equipped with standard fixtures and

  130 Union St Unit D, Bennington, VT 05201
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  /31

  $130,000 Sold Jun 12, 2025

  • 852 Sq Ft
  • $153/SF
  • 262 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1989

  432 South St Unit B4, Bennington, VT 05201

  This second-floor 2-bedroom, 2-bathroom end unit at Nathaniel Court is a fantastic opportunity! This is your chance to dip your toe into owning real estate without the hassle of yard maintenance, snow plowing or worrying about the cost of those pesky exterior home maintenance projects! This well-maintained condo association offers a quiet living environment. The unit features a renovated full

  Gabrielle Burdge Hoffman Real Estate

  432 South St Unit B4, Bennington, VT 05201
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  /35

  Est $246,821 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,184 Sq Ft

  312 School St Unit 314, Bennington, VT 05201

  312 School St Unit 314, Bennington, VT 05201
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  /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

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 327-7149

  226 North St, Bennington, VT 05201
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  /52

  $2,300 per month

  • 2 Beds
  • 2 Baths
  • 1,868 Sq Ft
  • Condo for Rent

  543 Gore Rd Unit 543, Bennington, VT 05201

  Fantastic 2 Bedroom, 2 Bathroom House with Mountain Views - $2300/month. Tenant pay for heat and internet.Step into comfort with this beautiful 2-bedroom, 2-bathroom fully furnished house available for rent. This home boasts an ensuite with a luxurious jet tub and shower, perfect for unwinding after a long day. The house also features a huge basement with a ping pong table, ideal for

  543 Gore Rd Unit 543, 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
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  /34

  Est $511,477 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,901 Sq Ft

  647 Fox Hill Rd, Bennington, VT 05201

  647 Fox Hill Rd, Bennington, VT 05201
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  /38

  $695,000

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

  359 Hickory Hill Rd, Bennington, VT 05201

  Welcome to this beautifully updated Center Hall Colonial, privately set on 2.58 wooded acres at the end of a peaceful cul-de-sac just minutes from downtown and major highways. The three bedroom, two and half bath home is truly move in ready, offering the perfect balance of comfort, style, and privacy. Step inside to an open concept main level where the kitchen flows seamlessly into the living

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 633-6530

  359 Hickory Hill Rd, Bennington, VT 05201
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  /8

  $950 per month

  • Studio
  • 1 Bath
  • 400 Sq Ft
  • Condo for Rent

  106 School St Unit 5, Bennington, VT 05201

  $950/month. Second floor studio apartment. Non smoking unit. First/Last/Security required. Credit and background checks required. Sorry, no pets. Heat, hot water, garbage included in rent.

  106 School St Unit 5, 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
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  /39

  Est $554,917 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,278 Sq Ft

  557 Fox Hill Rd, Bennington, VT 05201

  557 Fox Hill Rd, 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.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 204-5943

  905 County St, Bennington, VT 05201
• 

  

  /10

  $1,200 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  400 South St Unit 2, Bennington, VT 05201

  Come check out this recently renovated second floor apartment that offers a perfect blend of convenience and comfort. The unit was freshly painted a year ago and features new flooring in the kitchen. You'll love the natural light that floods the space through the skylights.Located in a convient downtown area. The apartment includes cooking gas, heat, water/sewer, and garbage in the rent,

  400 South St Unit 2, Bennington, VT 05201
• 

  

  /38

  $243,000 Sold Jun 09, 2025

  • 1,476 Sq Ft
  • $165/SF
  • 217 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1915

  111 Lyons St, Bennington, VT 05201

  Classic Bennington home on a quiet street with a beautiful yard and a detached barn/garage. First floor kitchen with dining area, laundry room, and a full bath, plus a living room and family room that could also be a first floor bedroom. Upstairs there are three bedrooms and a play room with a storage closet. Enjoy your morning coffee on the covered porch, and take a walk to downtown shops.

  Lilli West Maple Leaf Realty

  111 Lyons St, Bennington, VT 05201
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  /36

  Est $332,325 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  238 Bradley Dr, Bennington, VT 05201

  238 Bradley Dr, Bennington, VT 05201
• 

  

  /39

  $289,000

  • 3 Beds
  • 1 Bath
  • 1,608 Sq Ft

  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 cook with

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 858-4107

  30 Harbour Rd, Bennington, VT 05201
• 

  

  /8

  $1,175 per month

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • House for Rent

  166 N Branch St, Bennington, VT 05201

  Please do NOT click the "Request To Apply" button. This will cause a delay in our ability to respond to you. Read below for instructions on how to apply through our website.1br Second Floor Apartment for rent!Unit: 166 BApply To: Mountain View CommunityRent: $1175/moBeds/Baths: 1 beds 1 bathSize: 500 square feetPets: Cat & Dog friendly, all animals must be

  166 N Branch St, Bennington, VT 05201
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  /48

  $239,900 Sold Jun 06, 2025

  • 1,444 Sq Ft
  • $166/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1910

  213 Maple St, Bennington, VT 05201

  Welcome to this beautiful 3bed/2bath property nestled in the heart of Bennington, offering all the charm of yesteryear. A spacious front porch, perfect for relaxation and enjoying cool breezes, greets you upon arrival. The private backyard is a haven of tranquility, featuring an artful and curated oasis of mature perennials, ideal for entertaining, and includes a fully fenced yard, making it a

  Matt Waddington Hoffman Real Estate

  213 Maple St, Bennington, VT 05201
• 

  

  /20

  Est $330,115 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  306 Prospect St, Bennington, VT 05201

  306 Prospect St, Bennington, VT 05201
• 

  

  /4

  $225,000

  • 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
• 

  

  /43

  $265,000 Sold Jun 06, 2025

  • 1,422 Sq Ft
  • $186/SF
  • 50 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1920

  277 Union St, Bennington, VT 05201

  Enchanting, delightful, magical... this lovely c. 1920 village home is all of that and more! 3BR/2BA home has beautiful hardwood floors and a cook's kitchen with Corian countertops and not one but two pantries! Dining room, living room with electric fireplace, office/study that could also be a first floor bedroom and updated 3/4 bath round out the first floor. Upstairs there is the primary

  Vicki Wilson Maple Leaf Realty

  277 Union St, Bennington, VT 05201
• 

  

  /21

  Est $180,713 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  106 Park St Unit 16, Bennington, VT 05201

  106 Park St Unit 16, 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
• 

  

  /38

  $215,000 Sold Jun 06, 2025

  • 1,271 Sq Ft
  • $169/SF
  • 81 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1880

  230 Beech St, Bennington, VT 05201

  Charming 1880s home with 3 bedrooms and 2 full baths. Highly desirable "one floor living" with the kitchen, dining, living room, primary suite and laundry all on the main level. Two bedrooms are upstairs, which has lower ceilings. Both bathrooms have tiled floors, pedestal sinks, and fiberglass tub/shower units. Kitchen has warm maple cabinets, soft green laminate countertops and tin-look

  Jenifer Prouty Hoffman Hoffman Real Estate

  230 Beech St, Bennington, VT 05201
• 

  

  /19

  Est $162,206 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  106 Park St Unit 10, Bennington, VT 05201

  106 Park St Unit 10, Bennington, VT 05201
• 

  

  /4

  $279,000

  • 4 Beds
  • 4 Baths
  • 2,080 Sq Ft

  123 Bradford St, Bennington, VT 05201

  4 unit apartment building with great rental history and income. Front and back porches and balcony. Great location. Showings to begin 6/10/2024

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 210-1728

  123 Bradford St, Bennington, VT 05201
• 

  

  /19

  $141,000 Sold Jun 03, 2025

  • 819 Sq Ft
  • $172/SF
  • 46 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1989

  432 South St Unit C7, Bennington, VT 05201

  Welcome to easy living at Nathaniel Court! This clean and bright 2BR, 1.5-BA ground-level, end unit is ready to welcome you home. Tucked at the edge of this well-kept community, you’ll love the extra privacy, natural light, and comfortable layout. Just minutes from downtown Bennington’s shops, restaurants, and cultural spots—plus close access to local parks, healthcare, and everything else you

  Abi Gregorio

  432 South St Unit C7, Bennington, VT 05201
• 

  

  /29

  Est $446,559 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,652 Sq Ft

  9378 Vt Route 9, Bennington, VT 05201

  9378 Vt Route 9, Bennington, VT 05201
• 

  

  /32

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,584 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
• 

  

  /42

  $325,000 Sold Jun 03, 2025

  • 3,230 Sq Ft
  • $101/SF
  • 52 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1900

  209 Washington Ave, Bennington, VT 05201

  Gracious Victorian Lady in need of a new forever owner. Built as a doctor’s home and clinic, now two completed upstairs apartments, ready for a third, with office space and handicapped access downstairs. Beautiful, mature maples and a shady lawn with room to build a stand-alone studio or accessory dwelling. On Washington Avenue, two blocks to downtown. Perfect for a counselor, physiotherapist,

  Wendy Larson Maple Leaf Realty

  209 Washington Ave, Bennington, VT 05201
• 

  

  /16

  Est $246,979 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,005 Sq Ft

  214 Hickory Rd, Bennington, VT 05201

  214 Hickory Rd, Bennington, VT 05201

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