Bennington County, VT Homes

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  /38

  $4,975,000

  • 5 Beds
  • 4 Baths
  • 6,998 Sq Ft

  527 Benson Rd, Manchester Center, VT 05255

  Boorn Brook Farm combines the rich character of history and the comfort of contemporary living with complete privacy. Established in the late 1700s, the estate near Manchester Center offers stunning views of the Mt. Equinox and the Taconic Range. Surrounded by the Green Mountain National Forest, it creates a peaceful haven that balances the old and the new. For over 50 years, Marion Gould

  Story Jenks LandVest, Inc/Woodstock

  527 Benson Rd, Manchester Center, VT 05255
• 

  

  

  /20

  $1,275 per month

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

  18 Main St Unit C, North Bennington, VT 05257

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

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

  

  

  /40

  $595,000 Sold Nov 10, 2025

  • 1,886 Sq Ft
  • $315/SF
  • 31 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1985

  4A Ridge, Winhall, VT 05340

  4A Ridge Court is a welcoming townhouse in the highly desirable Piper Ridge community, just minutes from Stratton Mountain Base lodge and everything the area has to offer. This 3-bedroom, 3-bath furnished home features en-suite bedrooms, providing comfort and privacy for family and guests. The main level features a bright living room with wood-beamed cathedral ceilings, a wood-burning fireplace,

  Christiane Carroccio TPW Real Estate

  4A Ridge, Winhall, VT 05340
• 

  

  

  /21

  Est $153,062 Not Listed For Sale

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

  106 Park St Unit 16, Bennington, VT 05201

  106 Park St Unit 16, Bennington, VT 05201
• 

  

  

  /46

  $660,000

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft

  9 Pond View Rd Unit 9, Winhall, VT 05340

  Exceptional Renovation and Prime Intervale Location on the Pond . Beautiful upscale kitchen that opens to a wonderful great room with wood burning fireplace, cathedral ceiling, a spacious dining area and new deck with steps to the outdoors and pond. Tasteful details of this highly desirable floor plan with three bedrooms/3 baths that includes two bedrooms ensuite and a loft. The loft features

  Kim Morgan-Wohler Wohler Realty Group

  9 Pond View Rd Unit 9, Winhall, VT 05340
• 

  

  /10

  $1,475 per month

  • 3 Beds
  • 1.5 Baths
  • 980 Sq Ft
  • House for Rent

  35 Dudley Place, Bennington, VT 05201

  Please do NOT click the "Request To Apply" button. This will cause a delay in our ability to respond to you. Read below for instructions on how to apply through our website.3br MANUFACTURED HOME for rent!Unit: D-035Apply To: Mountain View CommunityRent: $1475/moBeds/Baths: 3 beds 1.5 bathsSize: 980 square feetPets: Cat & Dog friendly, all animals must be

  35 Dudley Place, Bennington, VT 05201
• 

  

  /31

  $1,347,000 Sold Nov 10, 2025

  • 6,200 Sq Ft
  • $217/SF
  • 110 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 2006

  951 Rupert Rd, Arlington, VT 05250

  Discover this irresistible Vermont estate near the New York border. Tucked down a long private drive, the home evokes a Scottish countryside manor. The spacious layout features a first-floor primary suite with two walk-in closets and a spa-like bath with dual sinks and a Jacuzzi tub. The large kitchen, with fireplace and breakfast nook, opens to a formal dining room overlooking your own personal

  Kristin Pirie Winhall Real Estate

  951 Rupert Rd, Arlington, VT 05250
• 

  

  /19

  Est $165,198 Not Listed For Sale

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

  106 Park St Unit 10, Bennington, VT 05201

  106 Park St Unit 10, Bennington, VT 05201
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  /52

  $725,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 4 Baths
  • 2,274 Sq Ft

  490 Barnumville Rd, Manchester Center, VT 05255

  490 Barnumville Road is a beautifully sited Manchester, Vermont home offering comfort, convenience, and classic Vermont charm on 1.78 flat, usable acres. Surrounded by peaceful views and just minutes from downtown Manchester, this property combines tranquil living with unbeatable access to everything the area has to offer — from ski and snowboard mountains to hiking trails, shopping, groceries,

  David Shehadi Josiah Allen Real Estate, Inc.

  490 Barnumville Rd, Manchester Center, VT 05255
• 

  

  /25

  $1,850 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 and security due at lease signing. Sorry no smoking, and no pets.

  9 Church St Unit 9 Church St, North Bennington, VT 05257
• 

  

  /7

  $345,000 Sold Nov 07, 2025

  • 1,368 Sq Ft
  • $252/SF
  • 127 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1985

  72 Mckee Rd, Arlington, VT 05250

  This charming 1985 Cape Cod style home, situated on 2.4 acres, is now available. The first floor features a kitchen with a cathedral ceiling, a comfortable living room, and two bedrooms. Upstairs, you will find an additional two bedrooms and a bathroom. The home also includes a full unfinished basement, offering potential for future expansion or storage. The barn could be used as a workshop or a

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  72 Mckee Rd, Arlington, VT 05250
• 

  

  /37

  Est $359,913 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft

  91 Mcguire St, North Bennington, VT 05257

  91 Mcguire St, North Bennington, VT 05257
• 

  

  /26

  $729,000

  • 3 Beds
  • 3.5 Baths
  • 2,262 Sq Ft

  253 Owls Head Hill Ln S, Dorset, VT 05251

  Welcome to this beautifully maintained Cape-style home tucked away on peaceful cul-de-sac with stunning mountain views. Enjoy your morning coffee on the front porch and relaxing evenings on the spacious back deck. Inside, you will find a warm and inviting layout featuring a gorgeous newer kitchen with modern finishes and ample space for cooking, gathering, and entertaining. The thoughtful floor

  Annette Gallo Real Broker LLC

  253 Owls Head Hill Ln S, Dorset, VT 05251
• 

  /2

  $950 per month

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

  106 School St Unit 3, Bennington, VT 05201

  $950/month. First floor one bedroom apartment. Non smoking unit. First/Last/Security required. Credit and background checks required. Sorry, no pets. Heat, hot water, garbage included in rent.

  106 School St Unit 3, Bennington, VT 05201
• 

  

  /43

  $180,367 Sold Nov 06, 2025

  • 400 Sq Ft
  • $451/SF
  • 40 Days On Market

  • 1 Bed
  • Built 1986

  634 Wiley Mountain Dr, Readsboro, VT 05350

  Escape to your own slice of paradise! This stunning vacation property, nestled within a serene tree farm, offers unparalleled privacy and tranquility. Fully furnished and move-in ready, it serves as a perfect vacation home or a lucrative Airbnb rental. Boasting ample land for recreation and potential expansion, this property is ideal for nature lovers and adventure seekers alike. Enjoy

  Cyd Scott Cohn & Company

  634 Wiley Mountain Dr, Readsboro, VT 05350
• 

  

  /30

  Est $407,616 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,623 Sq Ft

  94 Lake Dr, North Bennington, VT 05257

  94 Lake Dr, North Bennington, VT 05257
• 

  

  /20

  $534,900

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  1180 North Rd, East Arlington, VT 05252

  Have your own slice of quintessential Vermont with this 3 acre property at the base of the Green Mountains. A lush, wooded, private property, you will love this 4 bed, 2.5 bath Sunderland home. The 1st floor is an open floor plan with plenty of natural light with a bonus recreational room/office and half bath. The kitchen has granite counters with an updated faucet and oven hood with a butcher

  Jason Saphire www.HomeZu.com

  1180 North Rd, East Arlington, VT 05252
• 

  

  /20

  $1,275 per month

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

  18 Main St Unit C, North Bennington, VT 05257

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

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

  

  /42

  $345,000 Sold Nov 06, 2025

  • 1,728 Sq Ft
  • $200/SF
  • 77 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1993

  639 Wiley Mountain Rd, Readsboro, VT 05350

  Updated mountain home on 13.63 flat, usable acres bordering the Green Mountain National Forest and offering an outdoor paradise in every season. Tucked at the top of a quiet road, this property blends comfort, space, and access to Vermont’s best year-round recreation.Inside, you’ll find new hardwood floors, a renovated kitchen and bathrooms, a main-level bedroom, a full bath, main-level

  Melissa Nebelski Skihome Realty

  639 Wiley Mountain Rd, Readsboro, VT 05350
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  /38

  Est $419,056 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,082 Sq Ft

  27 Horton Hill Rd, Shaftsbury, VT 05262

  27 Horton Hill Rd, Shaftsbury, VT 05262
• 

  

  /39

  $649,000

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  211 Rod and Gun Club Rd, Shaftsbury, VT 05262

  Welcome to Rod and Gun Club Rd. Offering 1748 sq ft, with a full useable basement, sitting on 4.43 acres of land, with a 3-bay garage with carport as well as, an attached 2-car garage, a barn with stalls if you want to have some animals. This newly renovated ranch style home with thoughtful design offers 3B,2Bath, with a spacious and flexible layout with a fireplace with a gas insert in the

  Wendy Larson Hooscik Realty

  211 Rod and Gun Club Rd, Shaftsbury, VT 05262
• 

  

  /50

  $1,800 per month

  • 4 Beds
  • 1.5 Baths
  • 1,750 Sq Ft
  • Condo for Rent

  129 Grandview St Unit 129, Bennington, VT 05201

  Very large 1,750 square foot apartment (don't hold me to that exact figure)* 9 foot ceilings on both first floor and second floor. Great space, charming* Has the old world feel to it. Building was erected in the late 1800s* It has a living room, dining room (with bay window) and home office on the first floor* It also has a decent sized kitchen on the first floor with fully

  129 Grandview St Unit 129, Bennington, VT 05201
• 

  

  /31

  $230,000 Sold Nov 05, 2025

  • 936 Sq Ft
  • $246/SF
  • 3 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1964

  50 Ledgely Dr, Shaftsbury, VT 05262

  Welcome to 50 Ledgely Drive, a charming and well-cared-for home located in one of Shaftsbury’s smaller neighborhoods. This 2 bedroom, 1 bath home is ideal for first-time buyers, downsizers, or anyone looking for a more manageable space with potential to grow. Solidly built and lovingly maintained over the years, this home offers great bones and a warm, inviting feel throughout. The efficient

  Erika Floriani Hoffman Real Estate

  50 Ledgely Dr, Shaftsbury, VT 05262
• 

  

  /37

  Est $371,234 Not Listed For Sale

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

  181 Dunham Ave, North Bennington, VT 05257

  181 Dunham Ave, North Bennington, VT 05257
• 

  

  /55

  $995,000

  • 5 Beds
  • 4.5 Baths
  • 2,321 Sq Ft

  24 N Branch Rd, Winhall, VT 05340

  Exceptional Renovation of a Stratton Resort Residence in the Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. Beautiful upscale baths with tile work and craftsmanship of the highest caliber. Wood floors throughout. Open gourmet kitchen makes for premier apres ski gatherings. With 5 bedrooms/4 baths and multiple ensuite- this mountain chalet has been updated

  Kim Morgan-Wohler Wohler Realty Group

  24 N Branch Rd, Winhall, VT 05340
• 

  

  /44

  $1,350 per month

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

  254 Union St Unit B, Bennington, VT 05201

  Second Floor Renovated Two Bedroom Apartment- second floor 2 bedroom, each bedroom has a closet- renovated, new windows and entry door- washer/dryer hookups in kitchen- new stove, new fridge- egress windows and carbon monoxide detectors- includes heat, garbage, plowing and lawncare- tenant pays hot water (electric) and electric - all new!- walk to all amenities,

  254 Union St Unit B, Bennington, VT 05201
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  /38

  $440,000 Sold Nov 05, 2025

  • 1,710 Sq Ft
  • $257/SF
  • 48 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1980

  12 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 wood-burning

  Julie Citron RE/MAX Four Seasons

  12 Murray Hill Heights Rd Unit 43, Manchester, VT 05255
• 

  

  /39

  Est $235,947 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
• 

  

  /60

  $629,000

  • 5 Beds
  • 3.5 Baths
  • 3,271 Sq Ft

  5408 Main St, Manchester Center, VT 05255

  A great in town location offering two Homes,#5406 and #5408. The Front house is a three bedroom, two full bath home with a great front covered porch with views of Mt. Equinox. You can easily walk to all of Manchester Center's amenities. The back Cottage has two bedrooms, one and a half baths with kitchen and living area. This property is zoned as multi use which provides the owners the ability to

  Robert Sabol Wohler Realty Group

  5408 Main St, Manchester Center, VT 05255
• 

  

  /27

  $535,000 Sold Nov 04, 2025

  • 3,100 Sq Ft
  • $173/SF
  • 419 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2000

  357 Kansas Rd, East Arlington, VT 05252

  Welcome to 357 Kansas Road! This beautiful property seamlessly blends rustic charm with modern amenities. Step onto the inviting covered porch, perfect for relaxing. An expansive great room featuring a massive kitchen island ideal for dining & entertaining. A quiet den flows into a great office space. Enjoy the built-ins of the office that make these spaces both functional & stylish. The main

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  357 Kansas Rd, East Arlington, VT 05252
• 

  

  /40

  Est $470,090 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,236 Sq Ft

  287 Hewitt Dr, North Bennington, VT 05257

  287 Hewitt Dr, North Bennington, VT 05257
• 

  

  /40

  $1,150,000

  • 5 Beds
  • 3.5 Baths
  • 4,017 Sq Ft

  11 Founders Hill Rd, Winhall, VT 05360

  Stratton Mountain location for full time or vacation style living! Spacious home that you can walk to Village, gondola, golf and Sports center. Corner lot justdown the street from the Stratton Mountain Club and the Base Lodge. Home has five bedrooms with a chefs kitchen that has Viking Stove, ice-maker and three dishwashers for entertaining guests. Living room and dining room are graced with

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  11 Founders Hill Rd, Winhall, VT 05360
• 

  

  /55

  $762,000 Sold Nov 03, 2025

  • 2,868 Sq Ft
  • $266/SF
  • 6 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1950

  3221 Hapgood Pond Rd, Peru, VT 05152

  Discover timeless charm in this 4 bedroom, 4 bath rustic post and beam mid-century farmhouse, perfectly situated beside a gently flowing Jones Brook located in the township of Peru. Blending warm natural elements with classic post and beam lines, this home offers a rare combination of character and serenity. Expansive windows frame peaceful views of the brook and surrounding landscape. The wooden

  Jamie Wylie Stratton Real Estate

  3221 Hapgood Pond Rd, Peru, VT 05152
• 

  

  /29

  Est $451,569 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,752 Sq Ft

  9378 Vt Route 9, Bennington, VT 05201

  9378 Vt Route 9, Bennington, VT 05201
• 

  

  /40

  $1,025,000

  • 4 Beds
  • 2.5 Baths
  • 3,086 Sq Ft

  19 Roundtree Rd, Bondville, VT 05340

  This rare offering, located in the North Brookwood neighborhood at the Stratton Mountain Resort, presents an opportunity to secure your legacy winter home and enjoy the revenue of a $38,000 seasonal tenant and also benefit from a tax adjustment at closing. Don't overlook the benefits this property offers. Located on Stratton Mountain Resort with shuttle and near the ski trails, this four-bedroom,

  Kim Morgan-Wohler Wohler Realty Group

  19 Roundtree Rd, Bondville, VT 05340
• 

  

  /50

  $675,000 Sold Nov 03, 2025

  • 2,570 Sq Ft
  • $263/SF
  • 1 Day On Market

  • 4 Beds
  • 3 Baths
  • Built 1925

  7 Landgrove Rd, Landgrove, VT 05148

  Tucked away in a corner of beautiful Landgrove village just off a quiet country lane, this beautiful Post & Beam residence is a fascinating home designed for entertaining and fun! Enjoy the charm and architectural interest of the historic country barn it once was and all of the modern amenities resulting from two major renovations in 1985 and 2005 with continued updates and improvements over the

  Claudia Harris Mary Mitchell Miller Real Estate

  7 Landgrove Rd, Landgrove, VT 05148
• 

  

  /16

  Est $207,905 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,005 Sq Ft

  214 Hickory Rd, Bennington, VT 05201

  214 Hickory Rd, Bennington, VT 05201
• 

  

  /41

  $520,000

  • 4 Beds
  • 2.5 Baths
  • 2,120 Sq Ft

  87 Grinka Farm Dr, Readsboro, VT 05350

  Set above the heart of Readsboro Village, this inviting four+ bedroom, two-and-a-half-bath home combines classic Vermont character with a versatile and welcoming layout. The first floor offers a formal living room centered around a striking fieldstone fireplace with a cast-iron woodstove, a separate den/media room for relaxation or movie night, a first-floor bedroom, a tasteful full bath, an

  Casey Scott Southern Vermont Realty Group

  87 Grinka Farm Dr, Readsboro, VT 05350
• 

  

  /16

  $282,500 Sold Nov 03, 2025

  • Land
  • 10.15 Acres
  • $27,833 per Acre

  • 19 Days On Market

  0 Foote Rd Unit 5053891, Dorset, VT 05251

  Discover the perfect blend of privacy, natural beauty, and convenience with this stunning 10.15-acre parcel located on peaceful Foote Road in Dorset, Vermont. Tucked away in a quiet and quaint setting, this exceptional property offers the ideal canvas for your dream home or getaway retreat. The land features a harmonious mix of cleared and wooded acreage, providing both open space for building

  David Shehadi Josiah Allen Real Estate, Inc.

  0 Foote Rd Unit 5053891, Dorset, VT 05251
• 

  

  /47

  Est $403,144 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,686 Sq Ft

  201 Erbs Way, Bennington, VT 05201

  201 Erbs Way, Bennington, VT 05201

Showing Results 121 - 160, Page 4 of 18