Bennington, VT Homes in ZIP Code 05257

• 

  

  

  /36

  $490,000

  • 3 Beds
  • 2 Baths
  • 2,108 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
• 

  

  

  /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
• 

  

  

  /31

  $400,000 Sold Aug 13, 2025

  • 1,624 Sq Ft
  • $246/SF
  • 10 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1961

  2374 Shaftsbury Hollow Rd, North Bennington, VT 05257

  Escape to peace and privacy in this beautiful 2-bedroom, 1 bath getaway home set on 7.15 picturesque acres, complete with your own private pond and surrounded by majestic mountains. Step inside to an open-concept kitchen, dining, and living area-perfect for entertaining or simply soaking in the serenity. The space is filled with natural light thanks to large windows that frame the stunning views.

  Kelley Mccarthy Mahar McCarthy Real Estate

  2374 Shaftsbury Hollow Rd, North Bennington, VT 05257
• 

  

  

  /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
• 

  

  

  /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
• 

  

  /26

  $1,750 per month

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Condo for Rent

  9 Mechanic St Unit B, North Bennington, VT 05257

  9 Mechanic St Unit B, North Bennington, VT 05257
• 

  

  /42

  $252,000 Sold Jul 25, 2025

  • 768 Sq Ft
  • $328/SF
  • 41 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1965

  935 Shaftsbury Hollow Rd, North Bennington, VT 05257

  A peace of heaven in the Hollow! Idyllic setting with 3.5 acres surrounded by trees. The property borders the Little White Creek, with hiking/biking trails all around for your own outdoor adventure or peaceful relaxation. Adorable house with 2 bedrooms, 1 bath, and an open concept main room. Wood-burning fireplace in the living room, plus there's a wood boiler and oil-fired hot air furnace in

  Jenifer Prouty Hoffman Hoffman Real Estate

  935 Shaftsbury Hollow Rd, North Bennington, VT 05257
• 

  

  /37

  Est $365,627 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft

  91 Mcguire St, North Bennington, VT 05257

  91 Mcguire St, North Bennington, VT 05257
• 

  

  /46

  $850,000

  • 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
• 

  

  /17

  $1,275 per month

  • 2 Beds
  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  18 Main St Unit A, North Bennington, VT 05257

  Centrally located 3 family house with awesome tenants and awesome neigbors.

  18 Main St Unit A, North Bennington, VT 05257
• 

  

  /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
• 

  

  /30

  Est $426,809 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 3,334 Sq Ft

  94 Lake Dr, North Bennington, VT 05257

  94 Lake Dr, North Bennington, VT 05257
• 

  

  /17

  $485,000

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft

  1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262

  Discover a true Vermont lifestyle at this meticulously maintained charming farmhouse nestled on picturesque Shaftsbury Hollow Road. This property combines historic character with thoughtful modern updates, offering a serene retreat with breathtaking mountain views across a just shy of 10-acre lot where the White Creek gracefully runs along one side and the entire back boundary. Step out onto the

  Lori Hurley Four Corner Properties LLC

  1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262
• 

  

  /60

  $652,000 Sold Jul 21, 2025

  • 4,708 Sq Ft
  • $138/SF
  • 65 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1857

  21 Main St, North Bennington, VT 05257

  Welcome to The Eddington House Inn – a quintessential country Bed & Breakfast nestled in the heart of the charming Village of North Bennington. This inviting property offers the perfect blend of historic character, modern comfort, and endless possibilities. Ideally located within walking distance to Bennington College, the Park McCullough Historic Governor’s Mansion, Lake Paran, and the acclaimed

  Thomas Martins Maple Leaf Realty

  21 Main St, North Bennington, VT 05257
• 

  

  /40

  Est $377,485 Not Listed For Sale

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

  211 Grandview St, North Bennington, VT 05257

  211 Grandview St, North Bennington, VT 05257
• 

  

  /36

  $498,000

  • 3 Beds
  • 2 Baths
  • 1,671 Sq Ft

  6 Dwyers Camp Rd, Shaftsbury, VT 05262

  Discover quintessential Vermont living in this charming home, ideally situated on 6.9 serene acres in scenic Shaftsbury, a picturesque town in Southern Vermont. This meticulously maintained residence offers a blend of rustic charm and modern sophistication, providing a tranquil retreat with convenient access to area amenities and attractions. Thoughtful renovations have elevated its interior,

  Lori Hurley Four Corner Properties LLC

  6 Dwyers Camp Rd, Shaftsbury, VT 05262
• 

  

  /60

  $420,000 Sold Jun 26, 2025

  • 2,753 Sq Ft
  • $153/SF
  • 31 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  123 Bank St, North Bennington, VT 05257

  Modern Updated Cape! Be amazed when you step into this expansive open concept home. This property has been lovingly updated, embracing a modern style. New flooring, new roof, two new baths, new windows & doors. Plus seamless gutters. Expanded finished square footage enhances the open flow and easy living. The Great Room offers open living/ kitchen/dining with a beverage bar, fire feature and

  Margretta Fischer Wohler Realty Group

  123 Bank St, North Bennington, VT 05257
• 

  

  /39

  Est $256,401 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,413 Sq Ft

  61 Dunham Ave, North Bennington, VT 05257

  61 Dunham Ave, North Bennington, VT 05257
• 

  

  /28

  $299,000

  • 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
• 

  

  /39

  $215,000 Sold Dec 30, 2024

  • 1,238 Sq Ft
  • $174/SF
  • 78 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1920

  3 Church St, North Bennington, VT 05257

  Classic New Englander style home in North Bennington is now for sale! This Church Street home is within walking distance to the village, schools, restaurants, post office and mile around woods trail. A quick five minutes to Bennington College, close to markets and restaurants in Bennington. Spend a day at Lake Paran, drive 30 minutes to skiing, or simply stroll the neighborhood. This home boasts

  Monique Geannelis Mahar McCarthy Real Estate

  3 Church St, North Bennington, VT 05257
• 

  

  /40

  Est $518,181 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,042 Sq Ft

  287 Hewitt Dr, North Bennington, VT 05257

  287 Hewitt Dr, North Bennington, VT 05257
• 

  

  /30

  $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 sun porch/mudroom, laundry and

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  374 Overlea Rd, North Bennington, VT 05257
• 

  

  /40

  $235,000 Sold Dec 10, 2024

  • 1,512 Sq Ft
  • $155/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  1645 Vermont Route 67 E, Shaftsbury, VT 05257

  Located in the desirable Village of North Bennington, this spacious 3-bedroom, 2-bathroom home offers single-level, open-concept living, complete with a cozy wood-burning fireplace. The large kitchen features a massive island, perfect for meal prep and casual dining. Additional highlights include a walk-up attic for ample storage or potential future expansion, as well as a 4-car detached garage,

  Jeffrey Dorman

  1645 Vermont Route 67 E, Shaftsbury, VT 05257
• 

  

  /29

  Est $377,335 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 2,400 Sq Ft

  604 Tinkham Rd, North Bennington, VT 05257

  604 Tinkham Rd, North Bennington, VT 05257
• 

  

  /36

  $399,000

  • 5 Beds
  • 3 Baths
  • 3,118 Sq Ft

  100 McCarthy Acres, North Bennington, VT 05257

  Nearly Lakefront Living in the Heart of North Bennington!Come for the space—stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

  Nicholas Charest Maple Leaf Realty

  100 McCarthy Acres, North Bennington, VT 05257
• 

  

  /38

  $299,000 Sold Nov 27, 2024

  • 1,500 Sq Ft
  • $199/SF
  • 58 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1934

  683 Water St, North Bennington, VT 05257

  This lovely 3 BR/2BA bungalow in North Bennington is perfect in so many ways. Completely renovated in 2022, nothing was overlooked and it's only gotten better since! Fresh landscaping and extensive drainage make it completely turnkey and low maintenance. Thoughtfully planned, the main floor is designed for single level living with a bedroom and full bathroom. Washer and dryer hookups are smartly

  Angela Bevin Maple Leaf Realty

  683 Water St, North Bennington, VT 05257
• 

  

  /24

  Est $496,893 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,783 Sq Ft

  318 Eleanors Way, North Bennington, VT 05257

  318 Eleanors Way, North Bennington, VT 05257
• 

  

  /24

  $42,000

  • Land
  • 0.48 Acre
  • $87,500 per Acre

  26 Asa's Way, Bennington, VT 05257

  Walking trails, a paved road, underground utilities, and water/sewer at the street, what more could you ask for? Situated high on Asa's Way, almost a half acre of slightly sloping and level lot is ready to build on. Over 200 feet of road frontage allows for many home designs; from a hillside house that maximizes the southerly sun, to a modern bungalow perched on a flat landing, bring your ideas!

  Angela Bevin Maple Leaf Realty

  26 Asa's Way, Bennington, VT 05257
• 

  

  /45

  $415,000 Sold Nov 26, 2024

  • 1,573 Sq Ft
  • $264/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1975

  294 Tinkham Rd, North Bennington, VT 05257

  Literally my favorite road in Shaftsbury, you'll soak up the most spectacular vistas of farms and mountains every day. Nestled in the woods with privacy, this property is lovable and charming. Both decks have been rebuilt, so you can watch the sunset from the front and entertain out back. Outdoor amenities include a new workshop (insulated/powered), kid's playset, firepit, raised garden beds,

  Jenifer Prouty Hoffman Hoffman Real Estate

  294 Tinkham Rd, North Bennington, VT 05257
• 

  

  /12

  Est $161,694 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  816 Shaftsbury Hollow Rd, North Bennington, VT 05257

  816 Shaftsbury Hollow Rd, North Bennington, VT 05257
• 

  

  /45

  $350,000

  • 4 Beds
  • 1 Bath
  • 1,680 Sq Ft

  19 Royal St, North Bennington, VT 05257

  Charming North Bennington Home in a Desirable Neighborhood.Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience—just steps from scenic hiking trails and close to Bennington College.Step inside to discover a freshly

  Lindsey Martin Maple Leaf Realty

  19 Royal St, North Bennington, VT 05257
• 

  

  /38

  $1,120,000 Sold Nov 22, 2024

  • 2,560 Sq Ft
  • $438/SF
  • 17 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2006

  1058 Granger Hollow Rd, North Bennington, VT 05257

  Rejuvenate your mind, body, and soul at your very own Vermont sanctuary. Over 40 acres of open meadows, rolling hills, fruit trees, berry bushes, stone walls, and a mature forest surround this sophisticated modern farmhouse. This is the perfect environment for buyers seeking privacy, beauty, and quiet broken only by birdsong. The owners spared no expense in developing this exceptional property.

  Carol O`Connor Four Seasons Sotheby's Int'l Realty

  1058 Granger Hollow Rd, North Bennington, VT 05257
• 

  

  /32

  Est $351,717 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft

  1041 Shaftsbury Hollow Rd, North Bennington, VT 05257

  1041 Shaftsbury Hollow Rd, North Bennington, VT 05257
• 

  

  /50

  $374,900

  • 5 Beds
  • 4 Baths
  • 3,400 Sq Ft

  927 Water St, North Bennington, VT 05257

  Stately North Bennington Colonial with In-Law Suite & Barn on 2.6 Acres.Step into timeless elegance in this beautifully crafted colonial-style home located in the heart of charming North Bennington. Offering 5 spacious bedrooms and 4 bathrooms, this home features a flexible floor plan that includes a private in-law suite, formal living and dining rooms, a welcoming foyer, and both front and

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  927 Water St, North Bennington, VT 05257
• 

  

  /40

  $405,000 Sold Nov 07, 2024

  • 2,508 Sq Ft
  • $161/SF
  • 56 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1900

  965 Water St, North Bennington, VT 05257

  Large Victorian home with many wonderful features. 4 bedrooms, 1 and half bathrooms. Kitchen and dining area are open to each other for entertaining. many built ins, beautiful wood floors and stained glass are spread through this home . Styled with a parlor and a family room, main level laundry, 3 season porch, hot tub and more. Outside the mature trees grant privacy and the barn/garage has

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  965 Water St, North Bennington, VT 05257
• 

  

  /30

  Est $461,195 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,429 Sq Ft

  414 Matteson Rd, North Bennington, VT 05257

  414 Matteson Rd, North Bennington, VT 05257
• 

  

  /52

  $425,000

  • 4 Beds
  • 2 Baths
  • 2,368 Sq Ft

  263 Elm St, North Bennington, VT 05257

  New Price! Fabulous Four Bedroom Farmhouse. Updated kitchen with new stainless steel appliances. Take in the mountain view through your newer windows over the new stainless steel sink and subway tile backsplash. Natural light graces this spacious home. The first-floor primary bedroom has a private walk-out deck overlooking the large level backyard. The generous living room opens up to a dining

  Margretta Fischer Wohler Realty Group

  263 Elm St, North Bennington, VT 05257
• 

  

  /24

  $395,000 Sold Sep 30, 2024

  • 1,100 Sq Ft
  • $359/SF
  • 23 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1850

  1 Pleasant St Unit B, North Bennington, VT 05257

  Discover a charming blend of comfort and style in this stunning 2-bedroom condo, perfectly situated on the scenic Paran Creek in North Bennington. As you enter, you're welcomed onto the upper level, where both spacious bedrooms are located. Descend to the lower level, and you'll be captivated by the open-concept design that seamlessly connects the kitchen, dining, and living areas. What truly

  Kelley Mccarthy Mahar McCarthy Real Estate

  1 Pleasant St Unit B, North Bennington, VT 05257
• 

  

  /36

  Est $224,559 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 900 Sq Ft

  2092 N Bennington Rd, North Bennington, VT 05257

  2092 N Bennington Rd, North Bennington, VT 05257
• 

  

  /53

  $595,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft

  23 Mechanic St, North Bennington, VT 05257

  Modern Comfort Meets Historic Charm in North Bennington, VermontNestled within the heart of North Bennington's National Historic District, this thoroughly modern and light-filled home offers the perfect blend of timeless character and contemporary living. Situated on a beautifully landscaped 0.69-acre lot, the property includes a private backyard with ample space for perennial and vegetable

  Kelley Mccarthy Mahar McCarthy Real Estate

  23 Mechanic St, North Bennington, VT 05257

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