Bennington, VT Homes

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  /36

  $199,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  1211 Carpenter Hill Rd, Bennington, VT 05201

  Charming, fully furnished woodland retreat on over 3.5 acres with sweeping mountain views. This private getaway features two cozy cabins, each with a sleeping loft, warm wood finishes, and rustic charm. The main cabin includes a vaulted living area with exposed beams, a wood stove, vintage-style kitchen, and a spacious deck with built-in seating.The second cabin offers flexible space for guests,

  

  Peter West

  BISHOP WEST REAL ESTATE

  (802) 278-9529

  1211 Carpenter Hill Rd, Bennington, VT 05201
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  Explore Bennington

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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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  /39

  $275,000 Sold Jul 31, 2025

  • 1,008 Sq Ft
  • $273/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
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  /13

  Est $62,714 Not Listed For Sale

  231 Chapel Rd, Bennington, VT 05201

  231 Chapel Rd, Bennington, VT 05201
• 

  

  

  /19

  $225,000 Under Contract

  • Land
  • 17 Acres
  • $13,489 per Acre

  1801 S Stream Rd, Bennington, VT 05201

  Welcome to 1801 South Stream Road a picturesque 16.68 acres of timeless Vermont charm property. This beautiful parcel features two classic Vermont red barns full of character and charm, that offer endless potential. With some repairs, they could be ideal for livestock, storage, or workshop space ready to support your vision for country living. A picturesque pond, in need of a little TLC, offers

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 317-7489

  1801 S Stream Rd, Bennington, VT 05201
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  /41

  $1,500 per month

  • 1 - 3 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  234 North St Unit 2, Bennington, VT 05201

  About a mile from the four corners. Well kept unit currently being remodeled W/D hookups in the unit. Sorry, no pets allowed. First/last/security due at lease signing. Credit and background checks required.

  234 North St Unit 2, 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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  /27

  Est $192,723 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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  /39

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,264 Sq Ft

  139 Mckinley St, Bennington, VT 05201

  Welcome to 139 McKinley Street in Bennington! This charming 1920 New Englander blends character and convenience in a great village location. Inside, you'll find a first-floor primary bedroom with laundry and a half bath downstairs, a cozy living room with a beautiful woodstove, and hardwood floors upstairs with easy care laminate throughout the main level.A standout feature is the

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (607) 437-6795

  139 Mckinley St, Bennington, VT 05201
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  /15

  $1,200 per month

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

  210 Beech St Unit 2, Bennington, VT 05201

  This 1 bedroom unit comes with a massive utility room for tons of extra storage space! The unit includes heat, water/sewer, and garbage in the rental price. Credit and background checks required. Sorry no pets Sorry no smoking. First/Last/Security due at lease signing.

  210 Beech St Unit 2, 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
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  /35

  Est $254,161 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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  /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

  (802) 444-8936

  755 Main St, Bennington, VT 05201
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  /18

  $1,500 per month

  • 2 Beds
  • 1.5 Baths
  • 852 Sq Ft
  • Condo for Rent

  432 South St Unit B4, Bennington, VT 05201

  Discover a delightful living experience at 432 South St. Unit B4, a welcoming 2-bedroom, 1.5-bathroom condo nestled in the highly sought-after Nathaniel Court neighborhood of Bennington, VT. Enjoy a range of amenities, including laundry hookups, a dedicated parking space, lawn care, plowing, and garbage taken care of by the association. Please note that pet will not be considered and smoking

  432 South St Unit B4, 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
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  /34

  Est $479,893 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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  /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

  (802) 471-3314

  303-305 Gage 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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  /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
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  /39

  Est $558,191 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
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  /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

  (802) 444-8271

  137 Park 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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  /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
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  /38

  Est $627,715 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,266 Sq Ft

  3347 West Rd, Bennington, VT 05201

  3347 West Rd, Bennington, VT 05201
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  /41

  $295,000

  • 5 Beds
  • 2 Baths
  • 1,588 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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  /51

  $1,400 per month

  • 1 - 3 Beds
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  9 Browning Place, Bennington, VT 05201

  PLEASE READ THIS AD CAREULLY.First floor small three bedroom- New kitchen (cabinets, countertops, appliances - fridge, stove and over the range microwave)- New bathroom, with washer dryer hookups in the bathroom- New recessed lighting- Washer / dryer hookups in bathroom- All the windows are new wood insulated windows.- The apartment will include heat, but not

  9 Browning Place, Bennington, VT 05201
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  /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
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  /21

  Est $180,260 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
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  /38

  $650,000

  • 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

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 633-6530

  359 Hickory Hill Rd, Bennington, VT 05201
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  /51

  $1,001 per month

  • 1 - 3 Beds
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  9 Browning Place, Bennington, VT 05201

  PLEASE READ THIS AD CAREULLY.First floor small three bedroom- New kitchen (cabinets, countertops, appliances - fridge, stove and over the range microwave)- New bathroom, with washer dryer hookups in the bathroom- New recessed lighting- Washer / dryer hookups in bathroom- All the windows are new wood insulated windows.- The apartment will include heat, but not

  9 Browning Place, Bennington, VT 05201
• 

  

  /60

  $230,500 Sold Jul 18, 2025

  • 1,002 Sq Ft
  • $230/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
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  /19

  Est $166,488 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
• 

  

  /11

  $179,900

  • 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
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  /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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  /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
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  /29

  Est $499,139 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
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  /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
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  /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
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  /16

  Est $219,602 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
• 

  

  /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

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