Bennington County, VT Homes

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  /50

  $650,000

  • 3 Beds
  • 2.5 Baths
  • 2,675 Sq Ft

  55 Monument Ave, Bennington, VT 05201

  Step back in time while enjoying modern comforts in this stunning c. 1787 Colonial home located in the heart of Old Bennington. Brimming with character and charm, this 3BR/3BA residence combines historic elegance with contemporary updates for today’s lifestyle. Inside, you’ll find a brand-new chef’s kitchen designed for culinary enthusiasts, complete with high-end appliances and ample counter

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 849-4742

  55 Monument Ave, Bennington, VT 05201
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  /16

  $5,500 per month

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • Townhouse for Rent

  556 Equinox On the Battenkill Unit J-11, Manchester, VT 05254

  SUMMER RENTAL 2026 - EQUINOX ON THE BATTENKILL There is so much to offer! This sought-after four-bedroom EOB townhome is now available for a summer seasonal rental. EOB amenities include tennis, pickleball, pool, and clubhouse privileges. Enjoy all that Manchester and the Mountains have to offer. We have the Manchester Music Festival, The Vermont Summer Festival, the Dorset Theatre, the

  

  Kristin Comeau

  TPW Real Estate

  (802) 348-2094

  556 Equinox On the Battenkill Unit J-11, Manchester, VT 05254
• 

  

  

  /19

  $241,000 Sold Sep 25, 2025

  • 1,070 Sq Ft
  • $225/SF
  • 4 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1990

  20 Rockwood St, Bennington, VT 05201

  As sweet and tidy as can be, this 3BR/1BA home on a residential street offers one level living just outside of town. Gleaming wood floors in the living room and kitchen; kitchen is efficiently laid out and the dining area opens out to a deck overlooking the landscaped back yard and creates a private retreat for your morning coffee. Full basement has been partially finished with a room perfect

  Vicki Wilson Maple Leaf Realty

  20 Rockwood St, Bennington, VT 05201
• 

  

  

  /22

  Est $267,001 Not Listed For Sale

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

  494 Atwood Dr, Pownal, VT 05261

  494 Atwood Dr, Pownal, VT 05261
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  /38

  $595,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  359 Hickory Hill Rd, Bennington, VT 05201

  Welcome to 359 Hickory Hill! Tucked away at the end of a peaceful cul-de-sac on 2.58 acres, this beautifully updated Center Hall Colonial offers privacy, space, and convivence just minutes from downtown Bennington and major highways to New York City, Boston, and beyond.This three bedroom, two and a half bath home is truly turnkey and move in ready. Inside, you'll find gleaming hardwood and

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 633-6530

  359 Hickory Hill Rd, Bennington, VT 05201
• 

  

  /22

  $2,500 per month

  • 1 Bed
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  51 Spruce St, Manchester Center, VT 05255

  Enjoy winter in the heart of Manchester Center with this charming 1 bed, 1 bath apartment located on Spruce Street. Beautiful sun room, updated kitchen, living room, tv room and bedroom with bath, laundry on the ground level. This single level unit offers a cozy and convenient retreat just steps away from shops, restaurants, and all the amenities downtown Manchester has to offer. Perfectly

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 565-5638

  51 Spruce St, Manchester Center, VT 05255
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  /4

  $96,906 Sold Sep 24, 2025

  • 777 Sq Ft
  • $125/SF
  • 26 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2025

  29 Dustin Dr, Bennington, VT 05201

  Welcome to 29 Dustin Drive, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  29 Dustin Dr, Bennington, VT 05201
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  /36

  Est $676,223 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,340 Sq Ft

  134 Grapevine Ln, Pownal, VT 05261

  134 Grapevine Ln, Pownal, VT 05261
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  /38

  $445,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 1,710 Sq Ft

  1243 Murray Hill Heights Rd Unit 43, Manchester, VT 05255

  Set in the heart of Manchester’s desirable Murray Hill community, this 3-bedroom, 3-bath condo in the Heights offers over 1,700 sq. ft. of comfortable, light-filled living with breathtaking mountain views. Enjoy a spacious three-level layout that offers privacy for guests with one of bedrooms on the top floor. The main living area is perfect for relaxing or entertaining, featuring a

  

  Julie Citron

  RE/MAX Four Seasons

  (802) 402-4782

  1243 Murray Hill Heights Rd Unit 43, Manchester, VT 05255
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  /53

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 2,289 Sq Ft
  • House for Rent

  473 Hapgood Pond Rd, Peru, VT 05152

  Enjoy peaceful country living just minutes from the J.J. Hapgood Store and beautiful Hapgood Pond in this sun-filled 3 bed, 2 bath home set on 2.5 private acres. The main floor features gleaming wood floors throughout, a bright and open kitchen, separate dining room, and a cozy living room with a wood stove—perfect for Vermont winters. All three bedrooms and both full bathrooms are conveniently

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 215-3650

  473 Hapgood Pond Rd, Peru, VT 05152
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  /47

  $240,000 Sold Sep 24, 2025

  • 2,404 Sq Ft
  • $100/SF
  • 114 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1895

  120 Imperial Ave, Bennington, VT 05201

  Nestled in the charming village of Bennington, Vermont, this stately 4-bedroom, 2.5-bath home blends timeless elegance with thoughtful updates. Built in 1895 and set on 0.41 acres, the property offers a rare combination of historic character and modern livability. A large Trex front deck with handicap accessible ramp to the front and kitchen doors welcomes you to the home, where you'll find

  Kelley Mccarthy Mahar McCarthy Real Estate

  120 Imperial Ave, Bennington, VT 05201
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  /40

  Est $1,080,683 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
• 

  

  /42

  $1,100,000

  • 5 Beds
  • 4.5 Baths
  • 4,453 Sq Ft

  6 Old Ridge Rd, Winhall, VT 05340

  Welcome to High Meadow, one of Stratton’s most desirable neighborhoods. This expansive residence at 6 Old Ridge Road offers over 4,600 sq. ft. across three finished levels, combining mountain convenience with comfort, privacy, and style. The main level features an open kitchen, dining and vaulted living room with fireplace, plus a sunroom, screened porch, stone patio, and a private primary suite.

  

  Trent Stephens

  Wohler Realty Group

  (802) 213-9409

  6 Old Ridge Rd, Winhall, VT 05340
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  /38

  $2,995 per month

  • 2 Beds
  • 2.5 Baths
  • 1,875 Sq Ft
  • House for Rent

  5451 River Rd, Arlington, VT 05250

  LUXURY HOUSE RENTAL ABOVE THE BATTENKILL!Available Now! Winter Ski Season or 6 months, 9 months, or a one-year rentalExperience the timeless beauty of Southern Vermont in this exceptional rental perched above the scenic Battenkill. Just six miles to Arlington village along Route 313, the peaceful Battenkill Valley unfolds a rare, unspoiled gem that captures the essence of the Vermont

  

  Kristin Comeau

  TPW Real Estate

  (802) 689-8318

  5451 River Rd, Arlington, VT 05250
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  /20

  $89,499 Sold Sep 24, 2025

  • 825 Sq Ft
  • $108/SF
  • 120 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2024

  72 Ethans Way, Bennington, VT 05201

  Welcome to 72 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Lewis model manufactured home offers 2 bedrooms, 2 bathroom, and 825 sq. ft. (16 x 56 ft.) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  72 Ethans Way, Bennington, VT 05201
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  /32

  Est $1,682,651 Not Listed For Sale

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

  40 Nims, Dorset, VT 05251

  40 Nims, Dorset, VT 05251
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  /29

  $495,000

  • 7 Beds
  • 4 Baths
  • 2,494 Sq Ft

  190 Cemetery Rd, Arlington, VT 05250

  Welcome to this rare two-lot offering on picturesque Cemetery Hill in Arlington, Vermont — ideal for multi-generational living, rental income, or simply extra space.The main home sits on 2.29 surveyed acres and offers 4 bedrooms and 2 bathrooms, with a cozy, light-filled layout and the character of a property that has been lovingly maintained by the same family for many years.On a

  

  Trent Stephens

  Wohler Realty Group

  (802) 200-2970

  190 Cemetery Rd, Arlington, VT 05250
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  /14

  $2,275 per month

  • 2 Baths
  • 1,120 Sq Ft
  • Property for Rent

  343 Dewey St, Bennington, VT 05201

  Well-maintained provider office space available for lease, offering approx. 1,120 sq ft. Layout includes a waiting room with half bath, reception area, 2 operatories (or rooms), private office, and an additional half bath. Shared kitchen with the adjacent unit. Staff enjoy a separate entrance and designated parking, distinct from the public entry and lot. Rent includes electric, heat/AC,

  

  Peter West

  BISHOP WEST REAL ESTATE

  (802) 347-1295

  343 Dewey St, Bennington, VT 05201
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  /38

  $370,000 Sold Sep 23, 2025

  • 1,809 Sq Ft
  • $205/SF
  • 59 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1964

  366 Clough Rd, Stamford, VT 05352

  Southern Vermont country home, right over the border of Berkshire County, MA. Centrally located between major ski areas in Vermont and MA this home is also just a short drive to all cultural attractions in Berkshire County (MassMoCA, The Clark, Hancock Shaker Village). Bordering the North Branch of the Hoosic River, the property offers river frontage and expansive views of the beautiful Green

  Debra Burchard OLD COUNTY PROPERTIES

  366 Clough Rd, Stamford, VT 05352
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  /40

  Est $908,753 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
• 

  

  /22

  $650,000

  • 3 Beds
  • 2.5 Baths
  • 1,248 Sq Ft

  203 Northside Dr, Bennington, VT 05201

  Welcome to 203–205 Northside Drive, a truly unique property that combines residential living with commercial potential all in one. Are you looking for the flexibility to live in an apartment while generating income from multiple rental units, or would you prefer to restore the property back into a spacious single-family residence? This property gives you both options. Currently configured with

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 471-3591

  203 Northside Dr, Bennington, VT 05201
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  /40

  $13,000 per month

  • 5 Beds
  • 4.5 Baths
  • 5,080 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

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 328-9426

  21 Valley View Rd, Winhall, VT 05255
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  /56

  $385,000 Sold Sep 23, 2025

  • 1,702 Sq Ft
  • $226/SF
  • 156 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  321 Chester Knoll Dr, Bennington, VT 05201

  Low maintenance lifestyle awaits~This new construction three bedroom two bath cape style home is energy efficient and up to the newest Vermont energy codes. On demand hot water and energy efficient heat system. Not only do you get brand new construction, but you have an option for one level living with living room, kitchen, dining, laundry, bedroom, and full bath all on one level. Upstairs has

  Lilli West Maple Leaf Realty

  321 Chester Knoll Dr, Bennington, VT 05201
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  /34

  Est $519,851 Not Listed For Sale

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

  32 County Rd, Stamford, VT 05352

  32 County Rd, Stamford, VT 05352
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  /55

  $850,000

  • 3 Beds
  • 3.5 Baths
  • 2,340 Sq Ft

  879 River Rd, Manchester, VT 05255

  Authentic 1800's center chimney, hand hewn post and beam cape on coveted River Road within a short walk to the Battenkill River! This beauty has had the fireplace chimney's lined, the eat-in "keeping room" kitchen updated nicely, and the plank flooring is all intact! 12 over 12 windows, chair rails, exposed framing, and original doors and hardware are exceptional. The kitchen has a Dutch Oven

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 300-3678

  879 River Rd, Manchester, VT 05255
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  /56

  $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
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  /60

  $275,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft

  19 Robinson Ave, Bennington, VT 05201

  This charming 3-bedroom, 1 bathroom ranch features one-level living. The updated gallery-style eat-in kitchen offers plenty of space and storage and leads into a spacious living room where you'll enjoy a large bay window and fireplace. Enjoy the beautiful hardwood floors throughout the bedrooms and hallways, which lead into a newly renovated full bath. There's a full basement which offers options

  Floyd Amidon Maple Leaf Realty

  19 Robinson Ave, Bennington, VT 05201
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  /40

  Est $2,992,219 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
• 

  

  /43

  $422,000

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  100 Walsh Rd, Arlington, VT 05250

  Tucked away in the picturesque Vermont Hamlet of Sandgate, home to just 480 residents, this property provides the perfect escape from the bustle of city life. Here, you can enjoy the warmth of a close-knit community, stunning natural surroundings, and easy access to local amenities.Sitting on a generous 1.5-acre lot, the property offers ample space for outdoor recreation and the peaceful

  

  Kristin Comeau

  TPW Real Estate

  (802) 521-2780

  100 Walsh Rd, Arlington, VT 05250
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  /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
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  /53

  $400,000 Sold Sep 22, 2025

  • 1,309 Sq Ft
  • $306/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  495 Fairview St, Bennington, VT 05201

  This charming cape style home is close to town yet enjoys a sense of rural privacy. There is an open floor plan for entertaining on the first floor as well as two bedrooms and a bath. The wood stove keeps you cozy on those cold winter evenings. The second floor is a primary suite with large bath including a claw foot soaking tub and walk-in closet. Access to the full basement via the

  Catherine Cairns Maple Leaf Realty

  495 Fairview St, Bennington, VT 05201
• 

  

  /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
• 

  

  /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
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  /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
• 

  

  /19

  $199,900 Sold Sep 19, 2025

  • 952 Sq Ft
  • $210/SF
  • 28 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1964

  42 Colvin Ave, Shaftsbury, VT 05262

  Discover comfortable single-level living in this well-maintained ranch-style home, perfectly situated on a 0.16-acre lot. Has 952 square feet, this residence offers three bedrooms and one full bathroom—ideal for families, first-time buyers, or those looking to downsize without compromising on style or functionality.Step inside to be greeted by hardwood floors that flow seamlessly

  Timothy Corcoran Mahar McCarthy Real Estate

  42 Colvin Ave, Shaftsbury, VT 05262
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  /26

  Est $364,410 Not Listed For Sale

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

  629 Glen Rd, Peru, VT 05152

  629 Glen Rd, Peru, VT 05152
• 

  

  /60

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 4,023 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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  /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
• 

  

  /33

  $355,000 Sold Sep 19, 2025

  • 2,072 Sq Ft
  • $171/SF
  • 22 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1948

  60 Knoll Crest Ln, Bennington, VT 05201

  Step into this well maintained brick and clapboard residence, perfectly nestled in a lovely neighborhood. Just minutes from the hospital and a short, pleasant walk to downtown, this home offers the best of both convenience and community.Bathed in natural light, the interior boasts an inviting and functional layout highlighted by gleaming hardwood floors and timeless character throughout.

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  60 Knoll Crest Ln, Bennington, VT 05201
• 

  

  /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

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