20,997

Bennington, VT Homes

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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.

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 402-4994

    32-34 Sage St, Bennington, VT 05257
  • /40

    $13,000 per month

    • 5 Beds
    • 4.5 Baths
    • 4,100 Sq Ft
    • House for Rent

    21 Valley View Rd, Winhall, VT 05255

    Spectacular 5 bedroom, 5 bathroom house with panoramic mountain views!!! Entry level offers a 2 car garage, laundry room, powder room and large eat in kitchen. Beautiful views out the back sun room! Kitchen opens up to cathedral ceilings in the great room with center stone fireplace, formal dining room, foyer and den. Expansive primary suite on the first floor over looking the back deck with hot

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 328-9426

    21 Valley View Rd, Winhall, VT 05255
  • /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
    • /26

      Est $359,197 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,071 Sq Ft

      629 Glen Rd, Peru, VT 05152

      629 Glen Rd, Peru, VT 05152
  • /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

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 347-6655

    338 Main St, Bennington, VT 05201
  • /29

    $7,000 per month

    • 4 Beds
    • 3.5 Baths
    • 4,536 Sq Ft
    • Townhouse for Rent

    111 Kestrel Ct Unit E-10, Manchestr Ctr, VT 05255

    AVAILABLE - 07/01/2025 - 08/31/2025 Top Notch SUMMER 2025 RentalStunning Equinox on the Battenkill townhome! Fully updated kitchen with stone countertops, European appliances, breakfast bar, and walk-in pantry. Wet bar is adjacent to the open concept living/dining rooms. Stunning views of the golf course and Equinox Mountain. There are queen beds in three bedrooms and Primary Suite

    Agent Photo

    Kristin Comeau

    TPW Real Estate

    (802) 392-2945

    111 Kestrel Ct Unit E-10, Manchestr Ctr, VT 05255
  • /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
    • /31

      Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 1,888 Sq Ft

      12 Stratton Rd W Unit 12, Winhall, VT 05340

      12 Stratton Rd W Unit 12, Winhall, VT 05340
  • /21

    $175,000

    • Land
    • 18 Acres
    • $9,749 per Acre

    0 U S 7, Pownal, VT 05261

    Beautiful Pownal Valley views from almost wherever you stand on this 17.95 acre parcel. Zoned for commercial use along the road frontage and rural residential in back creates opportunities for different types of development.

    Agent Photo

    Vicki Wilson

    Maple Leaf Realty

    (802) 327-8230

    0 U S 7, Pownal, VT 05261
  • /60

    $9,000 per month

    • 4 Beds
    • 2.5 Baths
    • 3,746 Sq Ft
    • House for Rent

    81 Pine Tree Ln, Manchester Center, VT 05255

    Welcome to this stunning newly built modern farmhouse, nestled on 3 private acres in a prime location just minutes from both Manchester and Dorset. This spacious 4 bedroom, 2.5 bath home offers a perfect blend of modern comfort and farmhouse charm. Bright and airy open concept first floor with kitchen, dining area, living room, and den – all opening to a spacious patio, perfect for entertaining.

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 577-2443

    81 Pine Tree Ln, Manchester Center, VT 05255
  • /41

    $1,150,000 Sold Jul 25, 2025

    • 2,593 Sq Ft
    • $444/SF
    • 369 Days On Market
    • 4 Beds
    • 5.5 Baths
    • Built 1997

    35 Old Ridge Rd, Winhall, VT 05155

    Located in Stratton High Meadow, this four-bedroom six-bathroom home has everything you need and has a winter shuttle up to Stratton base area for skiing and snowboarding. Walking into the home, there is a large mudroom with bench and plenty of room to get gear organized and ready for the day on the mountain. The two-bay garage is off the right. Continuing, the living and dining areas have

    Mike England Michael England Real Estate

    35 Old Ridge Rd, Winhall, VT 05155
    • /36

      Est $956,745 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,104 Sq Ft

      469 Laclair Rd, Shaftsbury, VT 05262

      469 Laclair Rd, Shaftsbury, VT 05262
  • /40

    $1,450,000

    • 4 Beds
    • 6 Baths
    • 4,272 Sq Ft

    1016 West Rd, Manchester Center, VT 05255

    Manchester Village...an award winning architect transformed this "Sears & Roebuck" mini farmstead indo Living Art! Masterful execution of architectural detail at every turn. Circular landscaped drive ties the residence, garages, and the an impressive party barn together for year round use. The substantial covered stone porch enters the arts & crafts foyer.. with study to one side, ahead the

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 357-7462

    1016 West Rd, Manchester Center, VT 05255
  • /35

    $3,500 per month

    • 3 Beds
    • 3 Baths
    • 1,312 Sq Ft
    • House for Rent

    3 Bromley Forest Rd, Winhall, VT 05340

    Adorable 3 bed, 3 bath ranch located on desirable Bromley Forest Road in Winhall, just over the border from Manchester. This fully furnished home offers a perfect blend of comfort and convenience in a peaceful, wooded setting. The main level features an open and inviting layout, including a spacious living room, a fully equipped kitchen, and a cozy dining area. The 1st floor primary bedroom

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 300-3940

    3 Bromley Forest Rd, Winhall, VT 05340
  • /27

    $65,000 Sold Jul 24, 2025

    • Land
    • 10 Acres
    • $6,500 per Acre
    • 5 Days On Market

    120 Harley Rd, Stamford, VT 05352

    Lovely wooded 10 +/- acre lot with great road access and river frontage located in the small town of Stamford, VT near the Massachusetts border. Frontage on both VT-100 and Harley Road, a private drive shared with just 3 neighbors. The North Branch of the Hoosic River runs through the property. Sink your lawn chair in the river and enjoy the cool water on a hot summers’ day. There is a

    Curtis Trousdale Preferred Properties

    120 Harley Rd, Stamford, VT 05352
    • /28

      Not Listed For Sale

      • 6 Beds
      • 6.5 Baths
      • 5,896 Sq Ft

      27 Mountain View Rd, Winhall, VT 05360

      27 Mountain View Rd, Winhall, VT 05360
  • /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

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 210-1728

    123 Bradford St, Bennington, VT 05201
  • /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
  • /34

    $610,000 Sold Jul 24, 2025

    • 1,768 Sq Ft
    • $345/SF
    • 62 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2003

    35 Valley Pass, Manchester, VT 05255

    You’ll fall in love with this charming, fully renovated Cape tucked away in one of Manchester’s most peaceful neighborhoods. Just minutes from downtown, this beautifully renovated 4-bedroom, 3-bathroom home blends modern style with everyday comfort. Since 2022, the property has undergone a top-to-bottom transformation. The main floor now features a bright, open-concept layout with a brand-new

    Christiane Carroccio TPW Real Estate

    35 Valley Pass, Manchester, VT 05255
    • /38

      Est $762,685 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,081 Sq Ft

      80 Pond View Rd, Winhall, VT 05340

      80 Pond View Rd, Winhall, VT 05340
  • /15

    $115,000

    • Land
    • 2.90 Acres
    • $39,655 per Acre

    Lot 3 Route 11 30, Winhall, VT 05340

    Spectacular West and Southerly Views over Manchester Valley and boasts a bird's eye view across to the Equinox Mountain!Located on the Manchester side of Winhall, this property is at the end of a private lane offering privacy... engineered and offering VT Waste Water and Potable Water Supply Permit: WW-2-3614, design for 3 BR single family residence. Bordered by the Green Mountain Nat'l

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 808-6197

    Lot 3 Route 11 30, Winhall, VT 05340
  • /35

    $9,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,908 Sq Ft
    • House for Rent

    43 Cranberry Hill Rd, Winhall, VT 05340

    First time available for a seasonal rental.Call 43 Strattonwald home for your 25-26 ski season. This recently updated modern, yet classic chalet has room for all. With four bedrooms, two of the primary bedrooms with en-suite bathrooms, there is ample room for everyone's comfort. The home has brand new bathrooms, modern decor and state of the art appliances. With several living areas

    Peggy O'neill Cummings & Co

    43 Cranberry Hill Rd, Winhall, VT 05340
  • /25

    $515,000 Sold Jul 22, 2025

    • 1,731 Sq Ft
    • $298/SF
    • 77 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1986

    256 Hillcrest Rd, Manchester Center, VT 05255

    This well-maintained 3 bedroom, 2 bath home sits on a beautifully landscaped one acre lot in a desirable neighborhood on a quiet dead-end street with a cul-de-sac, offering minimal traffic and peaceful surroundings. Located just about a mile from the heart of Manchester and only 10 minutes to Bromley Mountain, the home provides both convenience and tranquility. Lovingly cared for by the same

    Katherine Zilkha Four Seasons Sotheby's Int'l Realty

    256 Hillcrest Rd, Manchester Center, VT 05255
    • /40

      Est $2,491,749 Not Listed For Sale

      • 4 Beds
      • 5.5 Baths
      • 4,711 Sq Ft

      674 Dorset Hollow Rd, Dorset, VT 05251

      674 Dorset Hollow Rd, Dorset, VT 05251
  • /2

    $20,000

    • Land
    • 3.00 Acres
    • $6,667 per Acre

    0 U S 7, Pownal, VT 05261

    3 acre parcel located behind other parcels. Would be a great place for a hunting "camp", blind or recreation. Right of Way is from 63 Metcalfe Road, Pownal.

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 210-3911

    0 U S 7, Pownal, VT 05261
  • /11

    $1,200 per month

    • Studio - 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    9 Main St Unit A, North Bennington, VT 05257

    Wonderful 1 bedroom unit in the Powers Market building. The unit looks out over the traffic triangle/fountain. Heat, garbage, and hot water included. Credit and background check required. Sorry no pets and no smoking. First last and security due at lease signing.

    9 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
    • /24

      Est $326,000 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,200 Sq Ft

      1116 Old Rd W, Arlington, VT 05250

      1116 Old Rd W, Arlington, VT 05250
  • /2

    $109,000

    • Land
    • 2.60 Acres
    • $41,923 per Acre

    0 Kesick Swamp Rd, Sunderland, VT 05250

    Terrific 2.6 acre building lot in Sunderland. Located at the end of Kesick Swamp Road. Private and almost ready to go. Some site work has been done and a septic design for a 2 bedroom home has been completed, just needs permitting. Current owner will change from recreational use to Residential use, prior to closing.

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 454-3023

    0 Kesick Swamp Rd, Sunderland, VT 05250
  • /16

    $7,000 per month

    • 4 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • House for Rent

    Lot 2 89 Jaquith Rd, Landgrove, VT 05148

    This one-of-a-kind experience on a gentleman's farm in one of the beautiful locations of Southern Vermont could be yours for this upcoming ski season. Centrally located to Stratton, Okemo, Magic and Bromley.With four large bedrooms, there is room for 12 people. There are two full baths leaving no room for time constraints when everyone is trying to get out the door to hit the slopes. A

    Peggy O'neill Cummings & Co

    Lot 2 89 Jaquith Rd, Landgrove, VT 05148
  • /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 $217,000 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,296 Sq Ft

      112 County Rd, Stamford, VT 05352

      112 County Rd, Stamford, VT 05352
  • /19

    $158,000 Pending

    • 2 Beds
    • 1.5 Baths
    • 819 Sq Ft

    432 South St Unit A7, Bennington, VT 05201

    Main level 2 bedroom, 1 and a half bathroom flat in Nathaniel Court. Well kept and low maintenance unit. Kitchen/Living room with laminate floors. Main level laundry. No pets.

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 402-4956

    432 South St Unit A7, Bennington, VT 05201
  • /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

    $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
    • /31

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft

      6 Black Birch Rd, Winhall, VT 05340

      6 Black Birch Rd, Winhall, VT 05340
  • /43

    $119,900 Pending

    • Land
    • 26 Acres
    • $4,665 per Acre

    0000 Skiparee Rd, Pownal, VT 05261

    Gorgeous 25.7 acre parcel on a dead end road in Pownal, Vermont. This wooded lot offers many possibilities for a home site. Across a stream and up the logging road there is a large clearing that would offer great privacy, with the mountain behind you and great views to the south and east. A lot of opportunity for outdoors activities, homesteading, livestock and gardening. This lot makes the world

    Agent Photo

    Max Squiers

    KW Vermont - Brenda Jones Real Estate Group

    (802) 392-2133

    0000 Skiparee Rd, Pownal, VT 05261
  • /39

    $13,000 per month

    • 7 Beds
    • 7 Baths
    • 6,600 Sq Ft
    • House for Rent

    89 Jaquith Rd, Londonderry, VT 05148

    It's time to start planning a Vermont winter retreat like no other. This stunning, architect designed property is located centrally to Okemo, Stratton, Bromley and Magic Mountains. The property is perfect for snowshoeing, cross country skiing ice skating and apres ski warming around the rustic fire pit area. Inside, you will have breathtaking views, top of the line amenities and features abound.

    Peggy O'neill Cummings & Co

    89 Jaquith Rd, Londonderry, VT 05148
  • /52

    $1,025,000 Sold Jul 18, 2025

    • 3,046 Sq Ft
    • $337/SF
    • 54 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1845

    21 Shepards Ln, Manchester, VT 05255

    Located on a prominent corner in the heart of Manchester Village, this charming approximately 1845 home offers classic style and comfortable living just steps from shops, restaurants, and outdoor activities. The home features a distinctive L-shaped layout with two full stories plus attic space, and a welcoming wraparound porch that adds to its curb appeal.Inside, you’ll find 4 bedrooms

    Christiane Carroccio TPW Real Estate

    21 Shepards Ln, Manchester, VT 05255
    • /33

      Est $525,145 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,344 Sq Ft

      935 Old Manchester Rd, Peru, VT 05152

      935 Old Manchester Rd, Peru, VT 05152

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