Bennington, VT Homes

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  /46

  $895,000

  • 5 Beds
  • 2 Baths
  • 2,424 Sq Ft

  2 Cold Spring Rd, North Bennington, VT 05257

  Welcome to 2 Cold Spring Road a cherished homestead steeped in history, beauty, and Vermont tradition. This 1785 Center Hall Colonial has been in the same family for generations and is now ready for its next chapter. With five spacious bedrooms, two full baths, and a classic layout that captures the warmth of country living, this property offers timeless charm with endless potential.Set on

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 810-8434

  2 Cold Spring Rd, North Bennington, VT 05257
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  /25

  $2,100 per month

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Condo for Rent

  9 Church St Unit 9 Church St, North Bennington, VT 05257

  Beautifully maintained 2 bedroom unit (half of a duplex) in desirable North Bennington. Heat included with rent.Credit and background checks required. First,last, security due at lease signing. Sorry no smoking, and no pets.

  9 Church St Unit 9 Church St, North Bennington, VT 05257
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  /11

  $163,000 Sold Jul 18, 2025

  • 780 Sq Ft
  • $209/SF
  • 70 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1937

  237 Church St, Pownal, VT 05261

  Cute 2 bedroom, 1 bath home in Pownal with small, easily maintainable lot. convenient to Williamstown and North Adams as well as Bennington. Needs some finishing touches and TLC.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  237 Church St, Pownal, VT 05261
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  /40

  Est $514,325 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,870 Sq Ft

  68 Willows Way Unit 4, Peru, VT 05152

  68 Willows Way Unit 4, Peru, VT 05152
• 

  

  

  /60

  $1,950,000

  • 4 Beds
  • 3.5 Baths
  • 3,333 Sq Ft

  1268 Myers Rd, Shaftsbury, VT 05262

  Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, a 2 car garage, top notch equestrian facilities, a trout and koi pond, and the list goes on and on. The winding driveway leads to a world away, as it opens to view of the exclusive estate in all of it's glory. The 3 Bedroom, 4000SF

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 441-6014

  1268 Myers Rd, Shaftsbury, VT 05262
• 

  

  /19

  $3,750 per month

  • 4 Beds
  • 2 Baths
  • 2,690 Sq Ft
  • House for Rent

  282 Highland Ave, Manchester Center, VT 05255

  In town, four bedroom, two bathroom house for rent. Main floor is a large mudroom and laundry room, kitchen, dining, office, living room, and full bathroom. Upstairs is 4 bedrooms, full bathroom, storage room. Central air conditioning. Wood floors throughout. Unfinished clean basement. Wrap around covered porch. Level yard, paved driveway. Walk to town. One car detached garage. Stand by backup

  Christiane Carroccio TPW Real Estate

  282 Highland Ave, Manchester Center, VT 05255
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  /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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  /4

  Not Listed For Sale

  AC Main St, Manchester, VT 05255

  AC Main St, Manchester, VT 05255
• 

  

  /36

  $499,900

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft

  1061 Granger Hollow Rd, North Bennington, VT 05257

  Dreaming of a peaceful Vermont lifestyle? This three bedroom, 2 bath home sits on 11.5 acres of beautiful land with rolling open mountain views, a stream, mature apple trees, and an inground pool all the ingredients for your perfect retreat.Step inside to this home that has had a complete refresh. The home offers a first floor bedroom and full bath with a step in shower, making it great

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 481-3292

  1061 Granger Hollow Rd, North Bennington, VT 05257
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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
• 

  

  /28

  $770,000 Sold Jul 18, 2025

  • 3,556 Sq Ft
  • $217/SF
  • 113 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1980

  5 Stratton Ridge Rd, Winhall, VT 05340

  Discover the ultimate Vermont ski retreat, just 2 miles from Stratton Mountain. This captivating home offers breathtaking mountain views across three spacious levels. The upper level features a private primary suite with a newly renovated bath and a cozy loft/office space — your peaceful sanctuary. The heart of the home, the main level, is perfect for gathering, with soaring cathedral ceilings,

  Carrie Mathews Winhall Real Estate

  5 Stratton Ridge Rd, Winhall, VT 05340
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  /35

  Est $623,746 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,577 Sq Ft

  10 Pond View Rd, Winhall, VT 05340

  10 Pond View Rd, Winhall, VT 05340
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  /62

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  679 Middle Pownal Rd, Pownal, VT 05261

  Nestled in the heart of rural Pownal, this beautifully renovated 4-bedroom, 3-bath home offers the perfect blend of modern comfort and peaceful countryside living. Set on 12.1 picturesque acres, the property features a mix of open level land and serene wooded areas, ideal for hobby farming, equestrian use, or simply enjoying nature. Inside, you'll find a spacious and thoughtfully designed layout

  

  Erin Vincent

  BISHOP WEST REAL ESTATE

  (802) 636-6092

  679 Middle Pownal Rd, Pownal, VT 05261
• 

  

  /19

  $3,000 per month

  • 2 Beds
  • 1 Bath
  • 3,800 Sq Ft
  • Apartment for Rent

  5138 Main St, Manchester, VT 05255

  Discover comfort and convenience in this fully renovated 2-bedroom, 1-bathroom apartment, ideally located in the vibrant community of Manchester Center, VT. Just steps away from local shops, restaurants, and the beauty of Manchester Center. This apartment offers the perfect blend of small-town charm and modern living. This convenient apartment features ample closet space, bright and airy

  Loana Sargent Wohler Realty Group

  5138 Main St, Manchester, VT 05255
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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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  /40

  Est $418,000 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,890 Sq Ft

  214 Pleasant St, Arlington, VT 05250

  214 Pleasant St, Arlington, VT 05250
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  /60

  $1,600,000

  • 5 Beds
  • 4.5 Baths
  • 4,243 Sq Ft

  397 Fern Hill, Dorset, VT 05251

  Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist’s retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 644-3043

  397 Fern Hill, Dorset, VT 05251
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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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  /55

  $707,500 Sold Jul 17, 2025

  • 2,944 Sq Ft
  • $240/SF
  • 55 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1997

  697 Hamilton Hollow Rd, Arlington, VT 05250

  Discover serenity and adventure at this stunning 40-acre property nestled in the foothills of Mt. Equinox. This beautifully updated contemporary home offers open-concept living with breathtaking, panoramic views that stretch for miles. Surrounded by expansive hiking trails and natural beauty, this home is ideal for year-round recreation and relaxation. The home’s lower level features a spacious

  Faith Rhodes Maple Leaf Realty

  697 Hamilton Hollow Rd, Arlington, VT 05250
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  /40

  Not Listed For Sale

  • 9 Beds
  • 8 Baths
  • 3,375 Sq Ft

  103 Winhall Hollow Rd, Bondville, VT 05340

  103 Winhall Hollow Rd, Bondville, VT 05340
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  /47

  $1,500,000

  • Land
  • 39 Acres
  • $38,890 per Acre

  500 Nims Rd, Dorset, VT 05251

  This Majestic and Private 38 + acre parcel located nearby the Dorset Village, is tucked away on an elevated and prepped site which just happens to be one of the most dreamy and picturesque estate quality lands offered in all of Dorset. Just a mile from the Dorset Green and perched up on a knoll with nothing less than amazing mountain views to the south, east and the north. Absolutely stunning

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 634-4776

  500 Nims Rd, Dorset, VT 05251
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  /48

  $7,000 per month

  • 5 Beds
  • 3.5 Baths
  • 3,858 Sq Ft
  • House for Rent

  20 Jamie Ln, Winhall, VT 05340

  Escape to the tranquility of Vermont with this stunning long-term rental at "Valley View." Nestled in a desirable neighborhood of Winhall, this spacious contemporary home offers unparalleled panoramic views of the surrounding mountains. Imagine waking up to the beauty of the Green Mountains every day in this expansive retreat!This meticulously maintained 5-bedroom, 3.5 bathroom home

  David Powers 42 North LP

  20 Jamie Ln, Winhall, VT 05340
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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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  /7

  Not Listed For Sale

  4 North Rd, Sunderland, VT 05252

  4 North Rd, Sunderland, VT 05252
• 

  /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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  /16

  $25,000 Sold Jul 16, 2025

  • Land
  • 7 Acres
  • $3,571 per Acre

  • 15 Days On Market

  0 Hawley Mountain Rd, Arlington, VT 05250

  Tucked away just off Murray Hollow Road, this 7-acre parcel offers the perfect blend of privacy, natural beauty, and outdoor adventure. Zoned Forest and Recreation, it’s an ideal spot for hunting, hiking, or establishing your own off-grid retreat.Access begins from a town-maintained road, leading you to a trail (locally referred to as Hawley Mountain) after a stream crossing that opens

  Faith Rhodes Maple Leaf Realty

  0 Hawley Mountain Rd, Arlington, VT 05250
• 

  

  /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
• 

  

  /60

  $1,150,000

  • 3 Beds
  • 3 Baths
  • 2,267 Sq Ft

  636 Dexter Rd, Shaftsbury, VT 05262

  In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic local backroads to write “Stopping by the Woods on a Snowy Evening." The Dexter Road Farmhouse, dating back 225 years, remains a testament to the enduring charm of Vermont and the simpler rhythms of country life. Nestled at the end of a serene, tree-lined town road, this charming 1800 farmhouse captures the

  

  Kristin Comeau

  TPW Real Estate

  (802) 520-1220

  636 Dexter Rd, Shaftsbury, VT 05262
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  /46

  $5,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  15 Nearing Rd, Winhall, VT 05340

  Imagine waking up to inspiring vistas every day in this remarkable 3 bedroom, 3.5 bath saltbox home. Perched to capture stunning panoramic views of Stratton Mountain's trails, this classic contemporary ski home offers a truly special living experience. The property is settled upon a 1.63-acre knoll and abuts the Winhall Forest, offering peace and privacy.Embrace sustainable living with a

  David Powers 42 North LP

  15 Nearing Rd, Winhall, VT 05340
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  /33

  $375,000 Sold Jul 16, 2025

  • 804 Sq Ft
  • $466/SF
  • 53 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1974

  46 Murray Hill Heights Rd Unit 17, Manchester, VT 05255

  Come see this in-town condominium with a garage! This unit features open bright kitchen and a living room with cathedral ceilings and a pellet stove, 2 bedrooms and 3 bathrooms. Enjoy the community amenities, including a pool, playground, and tennis courts. Furniture and appliances are included in the sale. Schedule a visit to see it for yourself. OPEN HOUSE on Memorial day 05/26/2025 from

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  46 Murray Hill Heights Rd Unit 17, Manchester, VT 05255
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  /40

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft

  740 Vt Route 9, Woodford, VT 05201

  740 Vt Route 9, Woodford, 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

  (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
• 

  

  /22

  $265,500 Sold Jul 15, 2025

  • 1,332 Sq Ft
  • $199/SF
  • 72 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  18 Stratton Ridge Rd, Winhall, VT 05340

  Welcome to 18 Stratton West Road – a charming 3-bedroom, 2-bath ski condo located just minutes from Stratton Mountain Resort. This spacious unit features over 1,300 square feet of well-maintained living space, complete with a cozy wood-burning fireplace, updated bathrooms, and generous natural light throughout. The open-concept layout is perfect for entertaining, with a functional kitchen, dining

  Derek Greene Derek Greene

  18 Stratton Ridge Rd, Winhall, VT 05340
• 

  

  /40

  Est $315,423 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  216 Bank St, North Bennington, VT 05257

  216 Bank St, North Bennington, VT 05257
• 

  

  /60

  $1,100,000

  • 4 Beds
  • 2.5 Baths
  • 3,215 Sq Ft

  92 Coventry Ln, Manchester Center, VT 05255

  Coventry House - Offered For The First Time! Built in 1972, the home was thoughtfully designed by local architect Charles "Bud" Lynch in collaboration with the owners. This custom-built home blends timeless design with natural surroundings. Offering a country kitchen, 4 bedrooms and 3+ vintage baths reflecting the 70’s era focus on color, natural materials, and open floor plans all on one level

  

  Kristin Comeau

  TPW Real Estate

  (802) 424-8410

  92 Coventry Ln, Manchester Center, VT 05255
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  /32

  $14,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • House for Rent

  14 Burnt Hill Rd, Winhall, VT 05340

  This modern Strattonwald gem is the ultimate plug-and-play Vermont summer house with location, style, convenience and a lake-side lifestyle to remember. Three living spaces -- one on each floor -- allow for plenty of overflow in the morning and afternoon, with two fireplaces ready for friends and family. Four bedrooms plus sleep loft with its own hang-out space lend space for the whole crew!

  Jamie Luke TPW Real Estate

  14 Burnt Hill Rd, Winhall, VT 05340
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  /41

  $750,000 Sold Jul 14, 2025

  • 1,836 Sq Ft
  • $408/SF
  • 55 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2022

  482 Horton Hill Rd, Shaftsbury, VT 05262

  Built in 2021, this stylish 3 bed, 3 bath modern home sits on 9.8 acres with wide open views from every angle. Large windows and a wraparound Trex deck with sleek cable railing blur the lines between indoors and out, with access from both the living room and primary suite. Inside, the open layout is designed for today's living-featuring a gorgeous kitchen with stainless appliances, granite

  Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  482 Horton Hill Rd, Shaftsbury, VT 05262
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  /40

  Est $815,323 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 4,000 Sq Ft

  386 Winhall Hollow Rd, Bondville, VT 05340

  386 Winhall Hollow Rd, Bondville, VT 05340

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