Bennington County, VT Homes

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  /33

  $239,000 Under Contract

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

  2460 East Rd, Shaftsbury, VT 05262

  Well-maintained 3-bedroom, 2-bath ranch-style home on a 1-acre lot at the outskirts of town. Offering 1,120 square feet of single-level living space, this property features an efficient floor plan with an eat-in kitchen, comfortable living room, and three bedrooms including a primary with half bath. The home is clean and functional, with an opportunity for cosmetic updates to suit your style.

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 474-4448

  2460 East Rd, Shaftsbury, VT 05262
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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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  /58

  $975,000 Sold Nov 27, 2025

  • 3,500 Sq Ft
  • $279/SF
  • 38 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1987

  20 Jamie Ln, Winhall, VT 05340

  Get ready for ski season! Plenty of space for the whole family. Set up for fun with two living rooms, a hot tub and barrel sauna. Great rental history. Owner is Listing Broker.

  David Powers 42 North LP

  20 Jamie Ln, Winhall, VT 05340
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  /36

  Est $732,832 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
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  /36

  $275,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,169 Sq Ft

  61 Autumn Acres, Bennington, VT 05201

  Welcome home to this charming single level ranch in a peaceful, friendly neighborhood where neighbors still wave hello and lend a cup of sugar. This home offers easy single-level living with three bedrooms, one full bath, and first floor laundry.Step inside to discover beautiful hardwood floors throughout most of the home, currently covered with carpeting that can easily be removed no nails

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 802-8871

  61 Autumn Acres, Bennington, VT 05201
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  /9

  $1,350 per month

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  87 Cone Rd, Manchester Center, VT 05255

  Roomy 1 bedroom apartments located on a quiet dead end road near the center of town. Open living, dining and kitchen area, washer and dryer, air conditioning, patio. No pets, no smoking. $1,350.00/month plus utilities. One year lease, first, last and security due on signing.

  87 Cone Rd, Manchester Center, VT 05255
• 

  

  /20

  $500,000 Sold Nov 26, 2025

  • 1,920 Sq Ft
  • $260/SF
  • 3 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1986

  374 Winhall Hollow Rd, Winhall, VT 05340

  Tucked away on 9.5 private acres that border the scenic Gale Meadows Pond, this Vermont retreat offers the perfect mix of nature, comfort, and functionality. Whether you're seeking a year-round residence or a seasonal getaway, this property is move-in ready with thoughtful renovations and room to explore. Step inside to a warm and inviting atmosphere where you’ll find brand-new kitchen

  Annette Gallo Real Broker LLC

  374 Winhall Hollow Rd, Winhall, VT 05340
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  /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
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  /15

  $915,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,898 Sq Ft

  3343 Main St, Manchester, VT 05255

  Steps from the heart of Manchester Village private 5 pastoral acres offer an unique opportunity while enjoying exceptional privacy and sweeping views of Equinox Mountain to the west. The Village, with marble walkways, underground power and electrified gas lanterns, undeniably creates a peaceful approach from a lengthy driveway back to this special residence buffered from the busy world, yet

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 808-6127

  3343 Main St, Manchester, VT 05255
• 

  

  /17

  $2,000 per month

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft
  • House for Rent

  13 Winhall Hollow Rd, Winhall, VT 05340

  Amazing Location!! This recently renovated home (2023) offers modern comfort in a quiet, wooded setting just minutes to Stratton Mountain. With 2.5 bedrooms, a full kitchen, and living spaces on both floors, it's an ideal year-roundresidence or seasonal ski retreat.The main bedrooms are spacious and bright, while the additional "half" bedroom features built-in bunks andlaundry perfect

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  13 Winhall Hollow Rd, Winhall, VT 05340
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  /60

  $625,000 Sold Nov 26, 2025

  • 2,034 Sq Ft
  • $307/SF
  • 56 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1885

  3 Short Rd, Bondville, VT 05340

  Charming Vermont Homestead: Ideal for Ski Lovers or Those Seeking a Homesteading Lifestyle Modern Updates Meet Classic Vermont Charm: Extensive updates over the years, including improved heating, plumbing and septic systems, radiant floors in the great room, renovated kitchen, new appliances, and updated bathrooms. Experience convenience and comfort while preserving the character of this original

  Mike England Michael England Real Estate

  3 Short Rd, Bondville, VT 05340
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  /24

  Est $320,000 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
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  /60

  $985,000 Under Contract

  • 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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  /9

  $1,350 per month

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  87 Cone Rd, Manchester Center, VT 05255

  Roomy 1 bedroom apartments located on a quiet dead end road near the center of town. Open living, dining and kitchen area, washer and dryer, air conditioning, patio. No pets, no smoking. $1,350.00/month plus utilities. One year lease, first, last and security due on signing.

  87 Cone Rd, Manchester Center, VT 05255
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  /16

  $130,000 Sold Nov 25, 2025

  • 1,290 Sq Ft
  • $101/SF
  • 45 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1966

  76 Harvest Hills Dr, North Bennington, VT 05257

  Single level living with 3 bedrooms and 1 bath home. Attached 2 car garage with direct access to the house. Nice level yard for outdoor activities and gardening. Full basement has great storage and possible additional living space. Spend quiet evening in the screened back porch that looks out over open field.

  Susan Bellville Bellville Realty

  76 Harvest Hills Dr, North Bennington, VT 05257
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  /40

  Est $248,576 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  112 County Rd, Stamford, VT 05352

  112 County Rd, Stamford, VT 05352
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  /28

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  72 Sawmill Rd, Pownal, VT 05261

  Experience the perfect blend of comfort and functionality in this modern doublewide, built in 2022, offering easy one-level living with upgraded insulation for energy efficiency. Features newer sitework with a drilled well and engineered septic system designed and permitted for 2 bedrooms, meaning 4-person occupancy. This spacious home features three bedrooms, allowing for versatile options using

  

  Gary Fuls Jr

  RE/MAX Transitions

  (802) 722-7730

  72 Sawmill Rd, Pownal, VT 05261
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  /49

  $10,000 per month

  • 4 Beds
  • 3 Baths
  • 5,624 Sq Ft
  • House for Rent

  37 Burnt Hill Rd, Winhall, VT 05340

  MARCH 2026 ONLY. Location, Stratton ski shuttle, style, and so much space: Welcome to your mountain home! This luxurious Strattonwald home offers bedrooms for the whole crew, plus loads of living space, light, a well-equipped, gourmet kitchen for cooking and entertaining, and a hot tub for après-ski memories. It is well-built, lovingly cared-for, and a rare opportunity to rent for just one month

  Jamie Luke TPW Real Estate

  37 Burnt Hill Rd, Winhall, VT 05340
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  /60

  $534,000 Sold Nov 24, 2025

  • 3,637 Sq Ft
  • $147/SF
  • 111 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2001

  272 Oak Hill Rd, Shaftsbury, VT 05262

  BRAND NEW ROOF!! RECENT PRICE REDUCTION TOO! Built in 2001, this stunning contemporary home sits on just under 8 peaceful acres and offers a perfect blend of space, light, and comfort. The grand two-story living room features soaring ceilings and a cozy pellet stove, creating an impressive focal point. The first floor offers a spacious primary suite for ultimate convenience, along with a

  Faith Rhodes Maple Leaf Realty

  272 Oak Hill Rd, Shaftsbury, VT 05262
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  /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
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  /58

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 3,284 Sq Ft

  1098 W Sandgate Rd, Arlington, VT 05250

  Private, Quiet, and Solidly built timeless Post & Beam 2,200 SF residence on 10.05 acres offering South and Westerly sunlight all day long ending with lovely sunsets! Overlooking a spring fed pond and a mix of open terrain and deciduous slope side forest with trails. The house offers main level all open 40' X 32' great room living / dining/ kitchen with a massive center 2.5 story stone fireplace.

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 992-1723

  1098 W Sandgate Rd, Arlington, VT 05250
• 

  /2

  Call for Price

  Apartment for Rent

  1 Bed

  87 Cone Rd, Manchester Center, VT 05255

  87 Cone Rd, Manchester Center, VT 05255
• 

  

  /29

  $535,000 Sold Nov 24, 2025

  • 1,850 Sq Ft
  • $289/SF
  • 72 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2002

  93 Mountain Ridge Rd, Peru, VT 05152

  Looking for a cozy Cape-style home near skiing, top-rated schools, and year-round outdoor activities? This charming yet modern residence, just minutes from Bromley, Magic, and Stratton Mountains and close to Londonderry and Manchester, offers the perfect blend of solid construction and timeless character. Built from the ground up in 2002, it features wide pine floors with radiant heat throughout,

  Andy Reed Four Seasons Sotheby's Int'l Realty

  93 Mountain Ridge Rd, Peru, VT 05152
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  /40

  Est $498,491 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,010 Sq Ft

  68 Willows Way Unit 4, Peru, VT 05152

  68 Willows Way Unit 4, Peru, VT 05152
• 

  

  /25

  $350,000

  • Land
  • 26.5 Acres
  • $13,208 per Acre

  942 Rt 315 Route, Rupert, VT 05768

  26.5 acres offering all the sought after components and is conveniently located nearby the greater Dorset/Manchester amenities! The 26.5 acres is enrolled in the Current Use (Land Use) program however, is about to be removed. The acreage backs onto the 3000 acre Merck Forrest Foundation which offers tremendous hiking, snowshoe trekking, camping, farmstead activity, sugaring, and nature tracking.

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 347-9113

  942 Rt 315 Route, Rupert, VT 05768
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  /19

  $4,000 per month

  • 4 Beds
  • 1.5 Baths
  • 1,404 Sq Ft
  • House for Rent

  937 Route 30, Dorset, VT 05251

  Welcome home! This beautiful and well maintained 4 bedroom, 1.5-bath home is in the charming town of Dorset. It offers over 1,404 sq feet of single-story living. This very well thought out and comfortable floor plan features a bright, large living and dining room and many windows throughout the entire house. A separate dining area perfect for gatherings. Enjoy the outdoors on the large back deck

  Martina Dvorak-Grattan Wohler Realty Group

  937 Route 30, Dorset, VT 05251
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  /38

  $635,000 Sold Nov 21, 2025

  • 2,499 Sq Ft
  • $254/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  825 Case Ln, Readsboro, VT 05350

  We are currently accepting backup offers. This custom chalet on 52.7 private acres features a soaring cathedral ceiling with floor-to-ceiling windows framing a breathtaking view of the mountains, which rise behind the reservoir as a stunning natural backdrop. Monadnock Mountain in New Hampshire can be seen in the distance, adding to the picturesque setting that can be enjoyed from anywhere in the

  Melissa Nebelski Skihome Realty

  825 Case Ln, Readsboro, VT 05350
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  /4

  Not Listed For Sale

  AC Main St, Manchester, VT 05255

  AC Main St, Manchester, VT 05255
• 

  

  /33

  $850,000

  • 4 Beds
  • 3.5 Baths
  • 3,658 Sq Ft

  146 Ridges Way Unit 1200-1, Peru, VT 05152

  The Top of the World! Follow the road to the very top of Bromley Village where this secluded condo enjoys sweeping views of the surrounding Green Mountains. This three level, well appointed unit has four nice sized bedrooms, three and a half baths and is a short walk to the Plaza trail for mountain access. Long time owners added special features to this Ridges Townhouse, including hand wrought

  

  Christopher Cummings

  Cummings & Co

  (802) 481-3899

  146 Ridges Way Unit 1200-1, Peru, VT 05152
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  /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
• 

  

  /48

  $296,500 Sold Nov 21, 2025

  • 1,896 Sq Ft
  • $156/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1993

  4 Rockwood St, Bennington, VT 05201

  Found your new home! This well maintained and updated ranch on a lovely corner lot has all of the ease of one-level living with all of the space you need. Relax on the covered side porch next to the stamped concrete patio with privacy fence for outdoor entertaining. Enjoy the sights and sounds of the peaceful brook on the wooded edge of the property. Two driveways provide ample parking for you

  Justine Curry Maple Leaf Realty

  4 Rockwood St, Bennington, VT 05201
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  /35

  Est $609,475 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
• 

  

  /36

  $699,000

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

  682 E Manchester Rd, Manchester Center, VT 05255

  Welcome to a private Vermont retreat that blends rustic post-and-beam charm with modern versatility. Nestled above the serene Bourne Brook, this property offers the perfect balance of privacy, natural beauty and convenience. The main house exudes warmth and craftmanship, and is complemented by an income producing apartment above the 2 car garage, adding flexibility for extra guests, long term

  

  Christopher Cummings

  Cummings & Co

  (802) 441-7038

  682 E Manchester Rd, Manchester Center, VT 05255
• 

  

  /19

  $35,000 per month

  • 3 Beds
  • 3 Baths
  • 2,920 Sq Ft
  • House for Rent

  2 Aspen Ln, Winhall, VT 05340

  Stratton views, sunlight, space, and location: this ski chalet has it all! The open floor plan of the main level brings everyone together around the spacious kitchen, dining area, and living room, under a vaulted cathedral ceiling and with a wall of windows overlooking the forest below and Stratton's peak ahead. Front deck offers dining area and a grill for the most outdoorsy of chefs! Two

  Jamie Luke TPW Real Estate

  2 Aspen Ln, Winhall, VT 05340
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  /29

  $367,000 Sold Nov 21, 2025

  • 1,937 Sq Ft
  • $189/SF
  • 54 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1945

  26 College Rd, North Bennington, VT 05257

  Here's the house you have been waiting for! An attractive 3-bedroom, 2-bath, brick-veneer cape, situated on a pretty corner lot, just a skip away from downtown North Bennington, with all its amenities, and next door to Bennington College. There's room for the family, with a flexible layout that offers lots of possibilities, including first-floor living, with a full bathroom on the first floor.

  Phil Lewis Mahar McCarthy Real Estate

  26 College Rd, North Bennington, VT 05257
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  /40

  Est $334,000 Not Listed For Sale

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

  214 Pleasant St, Arlington, VT 05250

  214 Pleasant St, Arlington, VT 05250
• 

  

  /29

  $415,000

  • 6 Beds
  • 3 Baths
  • 5,208 Sq Ft

  126 Washington Ave, Bennington, VT 05201

  Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property’s historic character, while modern updates support comfortable living and reliable income potential.

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 266-4364

  126 Washington Ave, Bennington, VT 05201
• 

  

  /15

  $1,225 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  938 Vt-7a Unit 4, Shaftsbury, VT 05262

  Lovely 2 bedroom apartment available in Shaftsbury Vermont. Rent includes water and sewer, snow plowing, and lawn maintenance. One year lease required with first and last month's rent and security deposit.

  938 Vt-7a Unit 4, Shaftsbury, VT 05262
• 

  

  /48

  $351,000 Sold Nov 21, 2025

  • 2,994 Sq Ft
  • $117/SF
  • 7 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1958

  165 Pippin Knoll, Bennington, VT 05201

  Set well back from the road, this mid-century modern home emphasizes simple lines, an indoor-outdoor connection, and panoramic views. The main level centers on an open living/dining/kitchen area anchored by a fireplace and oversized windows that overlook the pond and rolling landscape beyond. The primary suite on this level provides private comfort. A second-floor bedroom offers a rare

  Kelley Mccarthy Mahar McCarthy Real Estate

  165 Pippin Knoll, Bennington, VT 05201
• 

  

  /27

  Est $183,154 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

Showing Results 41 - 80, Page 2 of 18