Bennington County VT Homes for Sale

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  $875,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  447 Rock Bottom Ln, Peru, VT 05152

  Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the

  Andy Reed Four Seasons Sotheby's Int'l Realty

  447 Rock Bottom Ln, Peru, VT 05152
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  /24

  $389,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,535 Sq Ft

  515 Buck Hill Rd, Arlington, VT 05250

  Completely renovated from top to bottom, this move-in-ready home perfectly blends modern updates with classic Vermont charm. 3 bedrooms and 1 bathroom with a layout that includes multiple practical options for adding a second bathroom. The layout also includes a unique, unfinished bonus area off the primary bedroom with its own private staircase to the backyard—a blank canvas ideal for an

  Lori Hurley Four Corner Properties LLC

  515 Buck Hill Rd, Arlington, VT 05250
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  /48

  $429,000

  • 2 Beds
  • 2 Baths
  • 7,000 Sq Ft

  3310 Vermont 346, Pownal, VT 05260

  Former Church Offers So Many Opportunities. What might be your dream or requirements? This 1889 Church located in the quiet country village of North Pownal, Vermont, could fill them, however big or small. A single family home for all seasons and celebrations? A wedding venue? A place to live and work, rolled into one with plenty of space no matter what you do, from sculpting to computer imaging?

  Paul Harsch HARSCH ASSOCIATES

  3310 Vermont 346, Pownal, VT 05260
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  /51

  $625,000

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,364 Sq Ft

  635 Equinox On the Battenkill Unit L1, Manchester, VT 05254

  Equinox on the Battenkill – L-1 | Manchester Village, VTWelcome to one of the most desirable homes at Equinox on the Battenkill. Perfectly situated in historic Manchester Village, this is the only standalone residence in the community, offering the privacy of no shared walls along with beautiful mountain views.This spacious 4-bedroom, 3-bath home is filled with natural light from

  

  Margretta Fischer

  Wohler Realty Group

  635 Equinox On the Battenkill Unit L1, Manchester, VT 05254
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  /12

  $1,295,000

  • Land
  • 52 Acres
  • $24,904 per Acre

  0 Montgomery Rd, Pownal, VT 05261

  A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

  Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

  0 Montgomery Rd, Pownal, VT 05261
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  /54

  $1,990,000

  • 6 Beds
  • 6.5 Baths
  • 5,896 Sq Ft

  27 Mountain View Rd, Winhall, VT 05360

  Direct views of Stratton Mountain set the stage for this exceptional post-and-beam residence, offering a rare combination of luxury living, entertaining space, and rental flexibility. Handcrafted timber framing creates warmth and character throughout, while four fireplaces including a gas fireplace in the primary suite enhance the home's mountain atmosphere. Designed for gathering, the lower

  Jamie Wylie Stratton Real Estate

  27 Mountain View Rd, Winhall, VT 05360
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  /19

  $310,000

  $15K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,199 Sq Ft

  80 Murray Hill South Rd Unit 13, Manchester, VT 05255

  Imagine yourself enjoying all that Manchester has to offer in this 2-bedroom, 2.5-bath condominium, ready for its new owner.The inviting open living room features a soaring cathedral ceiling and a cozy wood-burning fireplace, creating the perfect space for relaxing or entertaining. The spacious kitchen offers plenty of room for cooking and gathering with family and friends.Conveniently

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  80 Murray Hill South Rd Unit 13, Manchester, VT 05255
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  /3

  $1,295,000

  • Land
  • 52.61 Acres
  • $24,615 per Acre

  00 Montgomery Rd, Pownal, VT 05261

  A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

  Ann Greenwood Alton + Westall Real Estate Agency, LLC

  00 Montgomery Rd, Pownal, VT 05261
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  /3

  $74,900

  • Land
  • 2.25 Acres
  • $33,289 per Acre

  0 Brambley Ln, Bennington, VT 05201

  Expansive 2.25-acre level lot situated on a quiet, private dead-end street. This is an amazing opportunity to build a dream home, a weekend retreat, or a spec house for investment. The property features 306 feet of road frontage, has been perc tested, and includes septic plans for a three-bedroom system. Located on the outskirt of town, but still close proximity to historic downtown Bennington

  Matt Waddington Hoffman Real Estate

  0 Brambley Ln, Bennington, VT 05201
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  /17

  $198,900

  • 2 Beds
  • 1 Bath
  • 1,332 Sq Ft

  348 Center St, Pownal, VT 05261

  Tucked into the rolling countryside of Pownal, this one-of-a-kind property offers something increasingly hard to find: space, story, and the freedom to make it your own. Set on 4.15 private acres, Once home to a beloved local dairy bar a second cabin and additional outbuildings, all awaiting the right buyer's vision and craftsmanship. Whether you're dreaming of a restored country residence, a

  

  Sheryl Morehouse

  Bishop West Real Estate, Inc.

  348 Center St, Pownal, VT 05261
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  /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
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  /55

  $995,000

  • 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
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  /54

  $825,000

  $74K PRICE DROP

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

  2572 Morse Hill Rd, Dorset, VT 05251

  Some properties announce everything at once. Others reward the buyer with discernment to see what is quietly waiting to be realized. Set along the rise of Morse Hill Road, this Dorset home is a rarer opportunity: a substantial residence on 10 acres where value extends beyond what exists today into what the land could become. Beyond a beautiful Vermont home, there is potential to shape an

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

  2572 Morse Hill Rd, Dorset, VT 05251
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  /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.

  39 Eagle Ridge, Dorset, VT 05251
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  $1,795,000

  $80K PRICE DROP

  • 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
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  $699,000

  $66K PRICE DROP

  • 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.

  2677 Route 30, Dorset, VT 05251
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  $277,700

  $1K PRICE DROP

  • 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 Real Estate

  32 Albe Dr, Bennington, VT 05201
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  /35

  $570,000

  $75K PRICE DROP

  • 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.

  185 Kelleher Rd Unit 10-00-99, Dorset, VT 05251
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  /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
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  $1,225,000

  • 4 Beds
  • 3 Baths
  • 3,357 Sq Ft

  153 High Meadow Rd, Winhall, VT 05340

  Located in Stratton Resort’s sought-after High Meadow community, this beautifully maintained and turnkey home offers the perfect blend of comfort, convenience, and mountain charm. Filled with natural light, the home features four bedrooms and three recently updated full baths, along with hardwood floors, cathedral ceilings, skylights, and a stunning floor-to-ceiling brick fireplace. Recent

  Britt Wohler

  153 High Meadow Rd, Winhall, VT 05340
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  /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
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  /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
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  /27

  $189,000

  $10K PRICE DROP

  • 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
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  $495,000

  $55K PRICE DROP

  • 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

  136 Fox Run Rd, Arlington, VT 05250
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  /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
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  /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
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  $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
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  /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
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  /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.

  1268 Myers Rd, Shaftsbury, VT 05262
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  /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
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  /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
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  /60

  $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 Real Estate

  515 Quarry Rd, Bennington, VT 05201
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  /38

  $575,000

  $10K PRICE DROP

  • 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
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  /19

  $182,000

  $13K PRICE DROP

  • 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
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  /29

  $250,000

  $50K PRICE DROP

  • 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
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  /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

  971 S Stream Rd, Bennington, VT 05201
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  /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
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  /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
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  /42

  $325,000

  $20K PRICE DROP

  • 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 Real Estate

  2154 U S 7, Pownal, VT 05261
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  /25

  $675,000

  $35K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,108 Sq Ft

  184 W View Estates, Manchester Center, VT 05255

  Welcome to this well maintained 3-bedroom, 2.5-bath Colonial combining classic style with comfortable modern living. From the inviting front porch to the covered rear porch, patio, and fire pit, this home offers exceptional spaces for relaxing and entertaining both indoors and outdoors. The recently updated kitchen serves as the heart of the home with tasteful finishes and excellent

  Annette Gallo Real Broker LLC

  184 W View Estates, Manchester Center, VT 05255

Showing Results 81 - 120, Page 3 of 7