Bennington County VT Homes for Sale

• 

  

  

  /27

  $1,200,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  233 Squires Rd, Manchester Center, VT 05255

  Tucked into the picturesque countryside of Manchester, this nearly 19-acre Vermont property offers a rare blend of privacy, income potential, and endless opportunity. Just minutes from downtown Manchester, the location provides easy access to the Orvis Fly Fishing School, Equinox Mountain, the Batten Kill River, and year-round recreation at Bromley Mountain Ski Resort. Surrounded by natural

  Mark Triller Real Broker LLC

  233 Squires Rd, Manchester Center, VT 05255
• 

  

  

  /55

  $995,000

  Open Thu 11AM - 1PM

  • 4 Beds
  • 5.5 Baths
  • 4,502 Sq Ft

  3373 Main St, Manchester, VT 05254

  In the heart of Manchester Village, this four-bedroom, six-bath colonial blends classic New England charm with the kind of space and flexibility that fits modern living. Set on a level 0.85-acre lot with mountain views, the property offers both privacy and easy access to everything the village has to offer. Inside, you'll find character you can't replicate - spruce and pine floors, exposed beams,

  David Halligan Four Seasons Sotheby's Int'l Realty

  3373 Main St, Manchester, VT 05254
• 

  

  

  /57

  $899,000

  • 4 Beds
  • 3 Baths
  • 4,112 Sq Ft

  2572 Morse Hill Rd, Dorset, VT 05251

  Set along the rise of Morse Hill Road, this Dorset home has the quiet gravity of a place that feels discovered rather than merely shown. It carries the attributes buyers most often hope to find here: privacy, scale, high ceilings, fireplaces, a substantial bedroom count, ski access, village proximity, and a layered mountain outlook beyond the road, where the ridgeline appears through the trees

  Hayleyanne Van Der Kar Four Seasons Sotheby's Int'l Realty

  2572 Morse Hill Rd, Dorset, VT 05251
• 

  

  

  /39

  $798,000

  • 3 Beds
  • 5 Baths
  • 3,100 Sq Ft

  52 High Meadow Rd Unit 11, Winhall, VT 05155

  Rarely available in Stratton’s sought-after Fairway Meadow neighborhood, this spacious 3-bedroom, 5-bath townhome offers the perfect balance of mountain retreat and year-round convenience. Ideally located adjacent to the Stratton Golf Course and just a short drive to the ski slopes and Village, this townhome is perfectly positioned to enjoy every season in Southern Vermont. The inviting interior

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  52 High Meadow Rd Unit 11, Winhall, VT 05155
• 

  

  

  /49

  $1,450,000

  • 5 Beds
  • 4.5 Baths
  • 4,376 Sq Ft

  39 Eagle Ridge, Dorset, VT 05251

  5.7 beautiful acres just off of Morse Hill Road where the southern exposures are to behold, a warm and inviting modern designed residence, post and beam barn and sweeping mountain views await your attention! The 5 Bedroom mostly ensuite house features the grand open concept where living areas are spacious and distinctive areas yet transition beautifully from space to space with newly finished

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 416-4342

  39 Eagle Ridge, Dorset, VT 05251
• 

  

  /38

  $1,875,000

  • 4 Beds
  • 3 Baths
  • 3,370 Sq Ft

  1310 Dorset Hill Rd, East Dorset, VT 05253

  Perched on the side of Mount Aeolus and conveniently located near Manchester, this exceptional 4-bedroom, 3-bath contemporary retreat offers privacy, sophistication, and year-round natural beauty across 21 picturesque acres. Thoughtfully designed to embrace its surroundings, the property features rolling meadows, mature woodland, vibrant perennial gardens, and sweeping views of the Green

  Annette Gallo Real Broker LLC

  1310 Dorset Hill Rd, East Dorset, VT 05253
• 

  

  /32

  $534,900

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  764 Myers Rd, Shaftsbury, VT 05262

  This charming, beautifully updated Cape sits on a sprawling 2-acre lot in a highly sought-after section of Shaftsbury, offering breathtaking panoramic mountain views. Boasting character and gleaming hardwood floors throughout. The first floor features a large living room with built-in bookshelves and cozy wood stove, a primary bedroom, full bath, and spacious country kitchen with granite

  Matt Waddington Hoffman Real Estate

  764 Myers Rd, Shaftsbury, VT 05262
• 

  

  /60

  $765,000

  • 5 Beds
  • 5 Baths
  • 5,083 Sq Ft

  2677 Route 30, Dorset, VT 05251

  Myrick Mountain serves as the inspirational backdrop views over a private landscaped 1.8 acre yard for this continuous period architectural "Rambler" beginning with the 18th Century center colonial with early expanded balanced wings leading up to the most recent oversized garage addition boasting a full 1 Bedroom apartment over that are accessed by half story stairs down to garage or up to the

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 771-2476

  2677 Route 30, Dorset, VT 05251
• 

  

  /26

  $450,000

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

  36 Birch Hill Rd Unit 8 Red Maple, Winhall, VT 05340

  Exceptional Birch Hill residence showcasing one of the community’s most impressive renovations, designed for modern mountain living. At the heart of the home is a stunning kitchen that seamlessly blends style, function, and warmth — ideal for lively après-ski entertaining or relaxed Vermont weekends.With three well-appointed bedrooms plus an expansive den, there is ample space for family and

  Helen Nault

  36 Birch Hill Rd Unit 8 Red Maple, Winhall, VT 05340
• 

  

  /41

  $279,000

  • 2 Beds
  • 1 Bath
  • 2,142 Sq Ft

  32 Albe Dr, Bennington, VT 05201

  MOVE RIGHT IN AND MAKE YOURSELF AT HOME This beautifully maintained residence is perfect for those looking for the convenience of first floor living. Featuring tastefully painted rooms, bamboo flooring and modern appliances.The kitchen includes a dedicated eating area for family dining while the living room offers a warm and cozy gathering space. Both bedrooms are generously sized with large

  Beatrice O'Connell Maple Leaf Realty

  32 Albe Dr, Bennington, VT 05201
• 

  

  /35

  $645,000

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft

  185 Kelleher Rd Unit 10-00-99, Dorset, VT 05251

  This Pretty White Cape is located on a low traveled dead end road right off Dorset's Morse Hill Road... equidistance to Manchester and Dorset and an easy walk to the newly transitioning Green Ridge Elementary K-5, for the 26-27 school year. Beautifully maintained, this residence offers a lovely open Dining/Kitchen /Living great-room with vault that beholds sunlight all day long. The quartz

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 216-5666

  185 Kelleher Rd Unit 10-00-99, Dorset, VT 05251
• 

  

  /40

  $1,100,000

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

  6 Old Ridge Rd, Winhall, VT 05340

  Tucked into Stratton Mountain Resort’s sought after High Meadow neighborhood, 6 Old Ridge Road offers the rare combination of substantial square footage, significant recent exterior improvements, and the opportunity to personalize the interior aesthetic to your own taste. Encompassing over 4,600 sq. ft. across three finished levels, this expansive mountain home is designed for gathering,

  Trent Stephens Wohler Realty Group

  6 Old Ridge Rd, Winhall, VT 05340
• 

  

  /35

  $799,000

  • 4 Beds
  • 3.5 Baths
  • 3,078 Sq Ft

  63 Raspberry Hill Rd, Winhall, VT 05340

  Spacious and light-filled four-bedroom home ideally located in desirable Strattonwald, offering both winter and summer enjoyment in a private, peaceful setting. Enjoy convenient access to the Stratton winter shuttle, as well as summer amenities including a private pond and tennis courts. The home features generous living spaces perfect for gathering and entertaining, including a cozy fireplace

  Carrie Mathews Winhall Real Estate

  63 Raspberry Hill Rd, Winhall, VT 05340
• 

  

  /60

  $675,000

  • 4 Beds
  • 4.5 Baths
  • 3,350 Sq Ft

  85 Sylvan Ridge Rd, Bondville, VT 05340

  Great location, flexible living, and room for everyone! Featuring a massive private in-law suite with bonus room PLUS THREE additional bonus rooms in the main home — yes, THREE! Whether you need guest space, home offices, hobby rooms, or overflow sleeping areas, this Vermont property gives you options. Offered for the first time since it was built in 1986 and lovingly enjoyed by the same family

  

  KC Gandee

  Real Broker LLC

  (802) 471-3179

  85 Sylvan Ridge Rd, Bondville, VT 05340
• 

  

  /47

  $1,375,000

  New Construction

  • 3 Beds
  • 4.5 Baths
  • 3,415 Sq Ft

  3746 Main St Unit 1, Manchester, VT 05255

  Last Available Unit– This final Monarch on Main townhome is Luxury Living in Historic Manchester Village at its finest. Summer 2026, this premier Monarch on Main property offers the rare opportunity to own a thoughtfully designed townhome- front unit- in the heart of Manchester Village. Imagine an easy stroll to fine dinning, shopping and evening events. This three-level residence combines the

  Britt Wohler

  3746 Main St Unit 1, Manchester, VT 05255
• 

  

  /42

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  366 Kirby Hollow Rd, Dorset, VT 05251

  Set in a premier Dorset country setting with sweeping 360-degree views of rolling pastures, mountains, and neighboring farmland, this charming single-level ranch offers a rare opportunity to enjoy the beauty and tranquility of Southern Vermont. The home offers over 1,568 square feet of comfortable living space, including an open-concept kitchen, dining, and living area, an office, three bedrooms,

  Britt Wohler

  366 Kirby Hollow Rd, Dorset, VT 05251
• 

  

  /27

  $199,000

  • 3 Beds
  • 2.5 Baths
  • 1,485 Sq Ft

  432 South St Unit D2, Bennington, VT 05201

  Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to

  Abi Gregorio

  432 South St Unit D2, Bennington, VT 05201
• 

  

  /58

  $550,000

  • 2 Beds
  • 1.5 Baths
  • 1,504 Sq Ft

  136 Fox Run Rd, Arlington, VT 05250

  Perched above the Battenkill River Valley and surrounded by mountain views this two story Vermont Gem is waiting for you. The perfect size two bedrooms, two bath home offers maple hardwood flooring, oversized windows and soaring mountain views. Lovely perennial gardens, flowering apple trees and large meadows grace the 3.90 acre property. This thoughtfully constructed home was built in 2000 with

  

  Margretta Fischer

  Wohler Realty Group

  (802) 659-2408

  136 Fox Run Rd, Arlington, VT 05250
• 

  

  /52

  $2,285,000

  • 5 Beds
  • 4.5 Baths
  • 4,647 Sq Ft

  543 Lower Hollow Rd, Dorset, VT 05251

  A Serene Dorset Hollow Retreat Along the Mettowee River Tucked into the storied Dorset Hollow, this 4.6-acre retreat enjoys 488 feet of Mettowee River frontage, offering a rare blend of tranquility, comfort, and timeless Vermont charm. Expansive mountain views and the soothing sounds of the river surround you—fall asleep each night to its calming presence. Multiple outdoor spaces include a

  Britt Wohler

  543 Lower Hollow Rd, Dorset, VT 05251
• 

  

  /32

  $775,000

  • 5 Beds
  • 2 Baths
  • 3,500 Sq Ft

  20 Bishop Rd, Searsburg, VT 05363

  Sweeping long-range mountain views over the Green Mountain National Forest, Mount Snow, Haystack, and Stratton ridgelines from this stunning 2020 Moosehead log home. Situated on 7+ acres bordering thousands of acres of National Forest, the property offers direct access to VAST snowmobile trails, space to create your own private loops, and exceptional privacy — all while remaining just a short

  Adam Palmiter Berkley & Veller Greenwood/Dover

  20 Bishop Rd, Searsburg, VT 05363
• 

  

  /44

  $2,495,000

  • 4 Beds
  • 5.5 Baths
  • 4,506 Sq Ft

  3039 Vermont 30, Pawlet, VT 05761

  Tucked away at the end of a long, winding driveway, this remarkable Dorset Village estate sits on one of the area's largest parcels—over six private acres. A rare blend of privacy, history, and elegance, the home features four stunning stone fireplaces, exposed antique beams, reclaimed wood details, and abundant natural light throughout its flowing layout. Designed for gathering and making

  Carrie Mathews Winhall Real Estate

  3039 Vermont 30, Pawlet, VT 05761
• 

  

  /37

  $875,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  155 Brookman Rd, Pownal, VT 05261

  Gorgeous setting for this newly constructed home built in 2025, offering breathtaking views from the expansive front porch on 10+/- private acres. Thoughtfully designed with quality craftsmanship throughout, the custom kitchen features beautiful cabinetry, a large center island, gas range, and classic farmhouse sink, all open to the inviting living room with a cozy gas fireplace. The stunning

  Kelley Mccarthy Mahar McCarthy Real Estate

  155 Brookman Rd, Pownal, VT 05261
• 

  

  /60

  $1,495,000

  • 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, an oversized 2 car garage, top notch equestrian facilities, a trout pond, playhouse and the list goes on and on. The winding driveway leads one to an enchanting compound, as it opens to overlook the exclusive estate in all of it's

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 328-9214

  1268 Myers Rd, Shaftsbury, VT 05262
• 

  

  /32

  $275,000

  • 3 Beds
  • 1 Bath
  • 1,668 Sq Ft

  1384 Vermont 153, Rupert, VT 05776

  Beautiful country farmhouse with meadow views. Come see this 3 bedroom one bath home on half an acre surrounded by country views and meadows. Built in 1865 this Vermont homestead has a wonderful sunny garden area and attached one car garage. The main level has everything you need; a generous first floor bedroom and large bathroom, spacious living and dining areas and eat in kitchen with newer

  

  Margretta Fischer

  Wohler Realty Group

  (802) 559-5288

  1384 Vermont 153, Rupert, VT 05776
• 

  

  /29

  $149,900

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft

  256 Union St, Bennington, VT 05201

  Opportunity awaits in this classic New England-style home conveniently located near downtown Bennington and local amenities. Offering 3 bedrooms, 1 bathroom, spacious living areas, and plenty of natural light throughout, the property features a newer roof, low-maintenance vinyl siding, covered front porch, corner lot location, and off-street parking. Inside, the home offers an eat-in kitchen,

  Jeffrey Dorman

  256 Union St, Bennington, VT 05201
• 

  

  /39

  $1,575,000

  • 4 Beds
  • 5.5 Baths
  • 4,530 Sq Ft

  527 Sleighbell Ln, Manchester Center, VT 05255

  Set on over 11.5 private acres, this custom-built Colonial offers the kind of comfort, craftsmanship, and peace of mind that’s increasingly hard to find. Thoughtfully designed and maintained since it was built in 2004, this home blends timeless style with practical features for everyday living. With over 4,300 square feet, the layout provides generous space without feeling overwhelming. The home

  David Halligan Four Seasons Sotheby's Int'l Realty

  527 Sleighbell Ln, Manchester Center, VT 05255
• 

  

  /45

  $495,000

  • 3 Beds
  • 2 Baths
  • 1,382 Sq Ft

  298 Mad Tom Rd, Dorset, VT 05253

  Set on over half an acre in the heart of East Dorset Village, this newly renovated three-bedroom, two-bath bungalow blends modern upgrades with cozy charm—and even includes a peaceful brook running through the property. Recent upgrades include completely new kitchen and bathrooms and fresh interior paint throughout. The open-concept layout creates a bright,connected space that’s perfect for

  David Halligan Four Seasons Sotheby's Int'l Realty

  298 Mad Tom Rd, Dorset, VT 05253
• 

  

  /54

  $695,000

  • 4 Beds
  • 2 Baths
  • 1,614 Sq Ft

  515 Quarry Rd, Bennington, VT 05201

  Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the

  Vicki Wilson Maple Leaf Realty

  515 Quarry Rd, Bennington, VT 05201
• 

  

  /39

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,716 Sq Ft

  55 Uphill Rd, Landgrove, VT 05148

  Charming Landgrove with 18 acres, direct Stratton views and end of the road privacy. This beautiful contemporary offers generously sized rooms with over 2700 sq ft and a perfect Vermont floor plan. Easy entry from the large 2 car garage into the mud room area, and right into the kitchen. Expansive counter space and a cozy sitting area with propane stove for those cool winter mornings. The

  Brian Gehlich RE/MAX Four Seasons

  55 Uphill Rd, Landgrove, VT 05148
• 

  

  /48

  $295,000

  • 3 Beds
  • 2 Baths
  • 2,753 Sq Ft

  166 Cardinal Ln, Bennington, VT 05201

  Discover the charm and potential of this one-of-a-kind mid-century home, offered for sale for the first time. Set on 3.20 private acres with mature, lush landscaping, this spacious property offers a peaceful and serene setting while remaining conveniently close to shopping, schools, restaurants, and the hospital. Originally built in 1964, the home has grown through multiple additions over the

  Monique Geannelis Mahar McCarthy Real Estate

  166 Cardinal Ln, Bennington, VT 05201
• 

  

  /32

  $449,000

  • 4 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  32 Aspen Ln, Winhall, VT 05340

  A Sanctuary for Every Season:Picture the moment you turn off the main road and onto tree-lined Aspen Lane. The frantic pace of the week instantly drops away as you pull into your driveway. Tucked into a lush, wooded lot, this four-bedroom chalet is designed for those who live for the outdoors. Whether you’re here to chase the morning light on the slopes of nearby Stratton Resort or to spend a

  Robin Apps Four Seasons Sotheby's Int'l Realty

  32 Aspen Ln, Winhall, VT 05340
• 

  

  /37

  $584,900

  • 3 Beds
  • 2.5 Baths
  • 1,786 Sq Ft

  14A Marisa Ln, Dorset, VT 05251

  Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here. Step inside and discover an open floor plan that feels both spacious and inviting across

  Julie Citron RE/MAX Four Seasons

  14A Marisa Ln, Dorset, VT 05251
• 

  

  /18

  $195,000

  • 3 Beds
  • 1 Bath
  • 1,590 Sq Ft

  176 Glen Ave, Readsboro, VT 05350

  Charming and spacious 3-bedroom, 1-bath home situated on approximately 1.90 acres, offering warm character and generous living space. Beautiful wood floors flow throughout the home, complemented by fresh paint, making this property truly move-in ready.The expansive wrap-around porch is a standout feature, perfect for enjoying quiet mornings, relaxing afternoons, or entertaining family and

  Cassandra Ehrlich BHG Masiello Brattleboro

  176 Glen Ave, Readsboro, VT 05350
• 

  

  /29

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,824 Sq Ft

  103 Jennings Brook Dr, Bennington, VT 05201

  Located in the desirable Jennings Brook community, this condominium offers a wonderful opportunity to add your own personal touches while enjoying a convenient Bennington location. The spacious living room features a cozy fireplace, beautiful built-ins, and abundant natural light, while the large dining room provides an ideal setting for gatherings and entertaining. The foyer is currently used as

  Kelley Mccarthy Mahar McCarthy Real Estate

  103 Jennings Brook Dr, Bennington, VT 05201
• 

  

  /41

  $550,000

  • 5 Beds
  • 2 Baths
  • 1,974 Sq Ft

  971 S Stream Rd, Bennington, VT 05201

  Have you been searching for the Vermont farmhouse that truly feels like home? The one with the land, the barns, the mountain views, the wraparound driveway, the screened in porch, and the beautiful front porch where you can sit and enjoy quiet mornings and peaceful evenings? This is that home.Situated on over 17 acres, this property offers not one but two barns, established fenced pastures,

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 566-5234

  971 S Stream Rd, Bennington, VT 05201
• 

  

  /46

  $1,275,000

  • 4 Beds
  • 2.5 Baths
  • 4,084 Sq Ft

  1677 Barnumville Rd, Manchester Center, VT 05255

  Imagine a time where taverns were the heart of the community, where laughter echoed off thick brick walls and stories were told by firelight. Now see yourself enjoying the ease of Single Floor Living that includes an enormous primary ensuite, with laundry! Start your day in the completely updated kitchen and move effortlessly into the dining area and living room with an easy to light cozy propane

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  1677 Barnumville Rd, Manchester Center, VT 05255
• 

  

  /11

  $179,900

  • 2 Beds
  • 1 Bath
  • 848 Sq Ft

  302 U S 7 S, Woodford, VT 05201

  Over 3 acres, a brook and lots of woods for walking. Room for a terraced garden, tons of parking and minutes to Bennington! This 2 bedroom ranch style home has a huge eat in kitchen and a lovely big living room with lots of windows. There is a bonus sun room with laundry. Owners are using an attached shed as a chicken coop! Sweet find at this affordable price!

  Christine Lewis Brattleboro Area Realty

  302 U S 7 S, Woodford, VT 05201
• 

  

  /26

  $549,000

  • 4 Beds
  • 2.5 Baths
  • 2,688 Sq Ft

  67 Valley Pass, Manchester, VT 05255

  Welcome to 67 Valley Pass Road, where your new Vermont home awaits. This stylish split-level ranch has been meticulously maintained and is truly move in ready. The home features four bedrooms, highlighted by a spacious primary bedroom with an en suite bathroom.The upper level offers an updated open kitchen and dining area with an easy flowing layout. Just off the dining space is a cozy living

  Sara Buckley Josiah Allen Real Estate, Inc.

  67 Valley Pass, Manchester, VT 05255
• 

  

  /53

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,047 Sq Ft

  99 Coolidge Ave, Bennington, VT 05201

  This cute 3-bedroom, 1-bath cape offers comfortable in-town living with a fully fenced yard and recently renovated kitchen and bath. The laundry hookups are on the first floor which adds everyday convenience. Enjoy morning coffee or evening relaxation in the enclosed 3-season porch with outdoor fenced space perfect for pets, play, or gardening. The upstairs bedroom features unique built-ins that

  Catherine Cairns Maple Leaf Realty

  99 Coolidge Ave, Bennington, VT 05201
• 

  

  /42

  $345,000

  • 3 Beds
  • 1 Bath
  • 1,768 Sq Ft

  2154 U S 7, Pownal, VT 05261

  Charming antique Cape full of character and opportunity. This 3-bedroom, 1-bath home offers timeless New England charm with warm, inviting living spaces and a flexible layout ready for your personal touch. A first-floor bedroom and first-floor laundry provide the convenience of single-level living, while additional bedrooms upstairs offer flexibility for guests or office space. Original details

  Angela Bevin Maple Leaf Realty

  2154 U S 7, Pownal, VT 05261

Showing Results 1 - 40, Page 1 of 6