Bennington, VT Homes

• 

  

  

  /35

  $359,000

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  33 Aspen Ln, Bondville, VT 05340

  Minutes from Stratton Mountain, this cozy chalet offers the perfect mountain escape with timeless character and room to make it your own. Featuring a classic chalet style floor to ceiling stone fireplace and wood interior, this home exudes vintage alpine charm. There are three bedrooms, two baths and an open concept living space, providing plenty of room for gatherings or weekend getaways.

  

  Alison Cummings

  Cummings & Co

  (802) 424-9210

  33 Aspen Ln, Bondville, VT 05340
• 

  

  

  /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

  

  Kristin Comeau

  TPW Real Estate

  (802) 392-2945

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

  

  

  /23

  $235,000 Sold Jul 31, 2025

  • 784 Sq Ft
  • $300/SF
  • 3 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1986

  40 Bourn Brook Rd Unit 49, Manchester, VT 05255

  Cheery and bright 2 bedroom, 1 bath, 784 SF townhouse right in Manchester Center. Open floor plan kitchen, living and dining on the first floor with new furnance installed in 2022. Stainless steel appliances, laminate flooring and covered front porch. 2nd Floor is carpeted and has 2 bedrooms, 3/4 bath and laundry. Great location close to all restaurants, shopping and amentities that Manchester

  Laura Beckwith Josiah Allen Real Estate, Inc.

  40 Bourn Brook Rd Unit 49, Manchester, VT 05255
• 

  

  

  /22

  Est $313,715 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,048 Sq Ft

  494 Atwood Dr, Pownal, VT 05261

  494 Atwood Dr, Pownal, VT 05261
• 

  

  

  /19

  $158,000

  • 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.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 402-4956

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

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 577-2443

  81 Pine Tree Ln, Manchester Center, VT 05255
• 

  

  /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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  /36

  Est $693,988 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 7,102 Sq Ft

  134 Grapevine Ln, Pownal, VT 05261

  134 Grapevine Ln, Pownal, VT 05261
• 

  

  /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
• 

  

  /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

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 300-3940

  3 Bromley Forest Rd, Winhall, VT 05340
• 

  

  /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
• 

  

  /40

  Est $1,020,902 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,031 Sq Ft

  276 Wilcox Hollow Rd, Sandgate, VT 05250

  276 Wilcox Hollow Rd, Sandgate, VT 05250
• 

  

  /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
• 

  

  /25

  $5,500 per month

  • 3 Beds
  • 3.5 Baths
  • 2,660 Sq Ft
  • Townhouse for Rent

  36 Falcons Bluff Unit C-2, Manchestr Ctr, VT 05255

  Equinox On The Battenkill Furnished Rental Available Immediately! Annual, Summer season, and Winter season rentals available.Don't miss this opportunity to rent a fully furnished EOB, three-bedroom 3.5-bath rental in the highly sought-after, beautifully maintained Equinox on the Battenkill community. This home features a first-floor bedroom and a full bathroom. The sunny living room opens

  

  Kristin Comeau

  TPW Real Estate

  (802) 676-7292

  36 Falcons Bluff Unit C-2, Manchestr Ctr, VT 05255
• 

  

  /41

  $500,000 Sold Jul 29, 2025

  • 1,779 Sq Ft
  • $281/SF
  • 10 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1972

  361 Murray Hill Rd S Unit 1, Manchester, VT 05255

  Beautifully maintained 3-bedroom, 2.5-bath end unit in sought-after Murray Hill. This home offers the only 2-car garage in the community, stunning mountain views, and a spacious wrap-around deck for easy outdoor living. The open main level features vaulted ceilings, a wood-burning fireplace, hardwood floors, and newer windows and sliders. A light-filled eat-in kitchen provides generous counter

  Julie Citron RE/MAX Four Seasons

  361 Murray Hill Rd S Unit 1, Manchester, VT 05255
• 

  

  /32

  Est $1,614,588 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,507 Sq Ft

  40 Nims, Dorset, VT 05251

  40 Nims, Dorset, VT 05251
• 

  

  /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
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  /59

  $4,500 per month

  • 3 Beds
  • 4 Baths
  • 2,308 Sq Ft
  • House for Rent

  1728 Vermont 30, Dorset, VT 05251

  Escape to Cody Cottage, a charming 3 bed, 3 bath home perfect for outdoor enthusiasts and families alike! Nestled next to the scenic Dorset Quarry, this cozy retreat offers easy summer swimming and breathtaking mountain views. Vaulted ceiling in the living room with dining that opens to the updated kitchen with 2 seat island. 1st Floor has the primary bedroom with en suite bath, a guest bedroom

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 694-4997

  1728 Vermont 30, Dorset, VT 05251
• 

  

  /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
• 

  

  /15

  Est $434,930 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,856 Sq Ft

  371 Schenkar Rd, Pownal, VT 05261

  371 Schenkar Rd, Pownal, VT 05261
• 

  

  /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
• 

  

  /52

  $5,000 per month

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft
  • House for Rent

  397 Powderhorn Rd, Manchester Center, VT 05255

  Charming newly renovated ranch with 3 bedrooms, 2 baths is the perfect summer rental, offering a cozy and inviting atmosphere! Conveniently located close to town for easy access to shops and dining. Enjoy a fenced-in backyard with a deck, perfect for grilling and outdoor relaxation. The kitchen and living room are located on the first floor, along with the spacious primary bedroom featuring an en

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 729-7527

  397 Powderhorn Rd, Manchester Center, VT 05255
• 

  

  /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
• 

  

  /40

  Est $979,877 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,774 Sq Ft

  67 Coventry Ln, Manchester Center, VT 05255

  67 Coventry Ln, Manchester Center, VT 05255
• 

  

  /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
• 

  

  /31

  $6,500 per month

  • 4 Beds
  • 3.5 Baths
  • 2,340 Sq Ft
  • House for Rent

  294 Green Peak Orchard S, Dorset, VT 05253

  Escape to a stunning summer/winter retreat in Southern Vermont, featuring 4 spacious bedrooms and 3.5 baths. Nestled in the heart of nature, this property offers breathtaking mountain views, perfect for relaxation and outdoor adventures. Open-concept living/kitchen area with plenty of seating, a wood burning fireplace, and panoramic mountain views. Kitchen is fully equipped with modern

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 644-7034

  294 Green Peak Orchard S, Dorset, VT 05253
• 

  

  /6

  $33,000 Sold Jul 25, 2025

  • Land
  • 2.50 Acres
  • $13,200 per Acre

  • 11 Days On Market

  0 White Oaks Rd, Pownal, VT 05261

  Nature lovers, rejoice! This 2.5-acre secluded lot, nestled up a dirt mountain road, offers unparalleled privacy and a haven for wildlife. Located in Pownal, between Williamstown, MA, and Bennington, VT, this mostly level lot provides a potential ideal building site. You'll be just minutes away from incredible walking trails, including the Dome Trailhead, Agawam Trail, Broad Brook Trailhead,

  Matt Waddington Hoffman Real Estate

  0 White Oaks Rd, Pownal, VT 05261
• 

  

  /34

  Est $482,288 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,586 Sq Ft

  32 County Rd, Stamford, VT 05352

  32 County Rd, Stamford, VT 05352
• 

  

  /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
• 

  

  /18

  $4,500 per month

  • 4 Beds
  • 3 Baths
  • 2,500 Sq Ft
  • House for Rent

  191 Forest Mountain Rd, Peru, VT 05152

  WELCOME TO PERU MOUNTAIN LODGE... Now Available For Your Vermont Summer '25 Vacation! Don't Let This One Get away... Cozy open living area with four Bedrooms. Two bedrooms on the main level, the Main Suite in the loft above, and a fourth bedroom in the finished walk-out basement. This home boasts a cathedral ceiling, an updated cooks kitchen, and a striking stone fireplace with two

  

  Kristin Comeau

  TPW Real Estate

  (802) 889-8948

  191 Forest Mountain Rd, Peru, VT 05152
• 

  

  /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
• 

  

  /13

  Est $62,714 Not Listed For Sale

  231 Chapel Rd, Bennington, VT 05201

  231 Chapel Rd, Bennington, VT 05201
• 

  

  /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
• 

  

  /37

  $9,000 per month

  • 3 Beds
  • 3 Baths
  • 1,980 Sq Ft
  • House for Rent

  3093 Route 30, Dorset, VT 05251

  Wonderful Dorset Village Historic Colonial, private and completely protected by the established vintage tree line that buffers the neighbors and Route 30. Walk to Village location, this property has been fully renovated with updated kitchen and baths. The house is warm and welcoming with front and side covered porch entrance while the rear screened porch creates an expansive summer room to the

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 520-2909

  3093 Route 30, Dorset, VT 05251
• 

  

  /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
• 

  

  /40

  Est $3,050,709 Not Listed For Sale

  • 5 Beds
  • 7.5 Baths
  • 8,700 Sq Ft

  440 Marcia Ln, Dorset, VT 05251

  440 Marcia Ln, Dorset, VT 05251
• 

  /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
• 

  

  /40

  $3,250 per month

  • 2 Beds
  • 2 Baths
  • 1,360 Sq Ft
  • Condo for Rent

  20 Murray Hill Heights Rd Unit 20, Manchester Center, VT 05255

  Available Now For Winter '25/'26Welcome to 20 Murray Hill Heights! This tastefully decorated home has undergone a lovely renovation and is available for Winter '25/'26. Enjoy Winter Season in this cozy, well-furnished, air-conditioned two-bedroom plus bonus loft Townhouse. Enjoy all that Manchester, Vermont, has to offer. It is conveniently located in Manchester, VT, close to Bromley and

  

  Kristin Comeau

  TPW Real Estate

  (802) 328-9795

  20 Murray Hill Heights Rd Unit 20, 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
• 

  

  /22

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,708 Sq Ft

  16 Clark Rd, Rupert, VT 05776

  16 Clark Rd, Rupert, VT 05776

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