Bennington County VT Homes for Sale

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  /35

  $365,000

  • 3 Beds
  • 1.5 Baths
  • 1,256 Sq Ft

  261 Skyboro, Pownal, VT 05261

  Move-in ready Ranch offering comfortable one-level living in a peaceful setting with mountain views. Set on 1.89 acres and conveniently located for commuting to both Bennington and Williamstown, MA. This 3-bedroom, 1.5-bath home has been lovingly improved over the past five years. The owner has invested significant time and care into making the home warm, functional and easy to enjoy. Updates

  Emily Heyer Hoffman Real Estate

  261 Skyboro, Pownal, VT 05261
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  /18

  $79,000

  $30K PRICE DROP

  • Land
  • 17 Acres
  • $4,647 per Acre

  00 Bill T Dr, Readsboro, VT 05350

  Significant price reduction! This gently sloping 17acre parcel should not be overlooked. This property offers a dead-end location on a town-maintained road, providing you with privacy and convenience. Nestled in the charming town of Readsboro and surrounded by the beautiful Green Mountains, you will have easy access to VAST snowmobile trails and VASA ATV trails. Plus, you are just a stone's throw

  Michelle O'Neil Deerfield Valley Real Estate

  00 Bill T Dr, Readsboro, VT 05350
• 

  

  

  /13

  $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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  /42

  $3,900,000

  • 5 Beds
  • 7 Baths
  • 11,736 Sq Ft

  2236 River Rd, Manchester, VT 05254

  Set on more than 18 picturesque acres along desirable River Road in Manchester Village, this extraordinary, converted farm offers a rare blend of historic character, modern comfort, & endless possibilities. Thoughtfully transformed into a multi-use residential compound, the property features four distinct living, working, & entertaining spaces, each with its own personality and purpose.

  Carol O`Connor Four Seasons Sotheby's Int'l Realty

  2236 River Rd, Manchester, VT 05254
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  /52

  $850,000

  $120K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 5,764 Sq Ft

  24 Vt Route 11, Londonderry, VT 05148

  Some properties simply hold stories within their walls. Formerly the beloved Nordic Inn, this iconic Landgrove property has been thoughtfully reimagined into a gathering place designed for modern Vermont living while honoring its rich history of hospitality, adventure, and connection. Inside, six ensuite bedrooms, spa-inspired baths, multiple fireplaces, a chef’s kitchen, sun-filled all-season

  Nancy Jensen Four Seasons Sotheby's Int'l Realty

  24 Vt Route 11, Londonderry, VT 05148
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  /50

  $1,675,000

  • 3 Beds
  • 4.5 Baths
  • 3,434 Sq Ft

  272 Lewis Bend Rd, Manchester Center, VT 05255

  Introducing a charming 3-bedroom, 5-bathroom home for sale in the picturesque town of Manchester, Vermont. This beautifully designed residence offers a perfect blend of modern comfort and classic New England charm. Nestled within a serene, open landscape, this property is an oasis of tranquility.The home's main floor features a spacious and inviting living room with a cozy fireplace, wet bar,

  Christiane Carroccio TPW Real Estate

  272 Lewis Bend Rd, Manchester Center, VT 05255
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  /26

  $2,300,000

  • 5 Beds
  • 3.5 Baths
  • 3,332 Sq Ft

  241 High Hill Rd, Manchester Center, VT 05255

  Perched on a hillside in one of the area's most sought-after in-town locations, this special property offers a rare combination of privacy, breathtaking mountain views, and a picturesque pond, all just moments from local shops, restaurants, and amenities. Surrounded by established landscaping and filled with natural light, the home captures the beauty of its setting through expansive windows on

  Carol O`Connor Four Seasons Sotheby's Int'l Realty

  241 High Hill Rd, Manchester Center, VT 05255
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  /34

  $345,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  19 Winhall Condo Rd Unit 4, Winhall, VT 05340

  Tucked at the end of a quiet back road less than one mile from the Stratton Access Road, The Winhall Condos offer a peaceful mountain retreat with convenient access to both Stratton and Manchester. This updated 2-bedroom, 2-bath residence features an open-concept kitchen, living, and dining area, two elevated decks, and beautiful views of Stratton Mountain. Offered furnished and ready to enjoy,

  Cheyanne Pugliese

  19 Winhall Condo Rd Unit 4, Winhall, VT 05340
• 

  

  /35

  $939,000

  • 3,031 Sq Ft

  3191 Vermont 30, Dorset, VT 05251

  Dorset Village Investor's choice! Village Commercial... Currently Presenting a 5 unit, 3030 SF residence that can not be reproduced locally. This building has been lifted and a full (includes a small crawl) poured concrete foundation installed... dry as can be... clean as any basement can be hoped for! There are a mix of one bedrooms and studios... The configuration can be easily altered to

  Laura Beckwith Josiah Allen Real Estate, Inc.

  3191 Vermont 30, Dorset, VT 05251
• 

  

  /16

  $449,000

  $66K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255

  Breathtaking views of Mount Equinox await from the privacy of this three-bedroom, 2.5-bath end unit condominium, ideally located just minutes from town and the ski mountains. The top floor features a bright loft filled with natural light and a convenient half bath. The spacious living room opens to a private deck with stunning mountain views and includes a cozy wood-burning fireplace.The

  Northshire Sales Group Real Broker LLC

  14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255
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  /60

  $1,600,000

  • 5 Beds
  • 4.5 Baths
  • 4,243 Sq Ft

  397 Fern Hill, Dorset, VT 05251

  Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist’s retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire

  Laura Beckwith Josiah Allen Real Estate, Inc.

  397 Fern Hill, Dorset, VT 05251
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  /32

  $229,900

  $10K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,104 Sq Ft

  1955 Vt Route 100, Readsboro, VT 05350

  Open House: Saturday, August 15th from 10 am to 12 pm. Welcome to 1955 Vermont Route 100, a character-filled 1870 farmhouse offering 4 bedrooms, 2 bathrooms, and 2,104 square feet of finished living space on a half-acre country lot in Readsboro. Abutting Vermont National Forest and close to VASA and Vast Trails. Inside, warm wood details and inviting living spaces create a classic Vermont feel.

  Colt Hazell Flex Realty

  1955 Vt Route 100, Readsboro, VT 05350
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  /45

  $325,000

  • 2 Beds
  • 1 Bath
  • 976 Sq Ft

  3149 W Hill Dr, Readsboro, VT 05350

  VERMONT! Located close to 1,000's of acres of Green Mountain National Forest! A little piece of Vermont just waiting to be discovered! Tucked into nearly 13 surveyed acres of woods, this charming 1970s ranch offers the peace, privacy & simplicity so many look for. A stone wall outlines the parking area, with stone steps leading up & into the front screened in porch that overlooks the yard &

  Colleen Zajac MONARCH REALTY, INC.

  3149 W Hill Dr, Readsboro, VT 05350
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  /40

  $579,900

  $15K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,050 Sq Ft

  1649 E Manchester Rd, Manchester Center, VT 05255

  5 bedroom, 2 bath Manchester home in a highly functional ski location: about 8 minutes to Bromley and under 25 minutes to both Magic and Stratton, plus roughly 2 minutes to downtown Manchester and 1 minute to Route 7 for straightforward access in all conditions. The setting supports frequent winter use and works equally well for year-round occupancy. The house underwent a full gut renovation in

  Jonathan Minerick

  1649 E Manchester Rd, Manchester Center, VT 05255
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  /9

  $374,900

  • Land
  • 2.31 Acres
  • $162,294 per Acre

  0 Wall St, Winhall, VT 05340

  Offered as a set, this property presents a rare opportunity to own two separately deeded parcels in a location that is only minutes from Stratton Mountain yet worlds away from the bustle of the resort. Totaling 2.31 acres, this land is situated high on River Road where neighboring homes enjoy spectacular views of Stratton. Conceptual rendering showing the potential view is based on the current

  Cheyanne Pugliese

  0 Wall St, Winhall, VT 05340
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  /28

  $159,000

  $30K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 760 Sq Ft

  1675 Vermont 9, Searsburg, VT 05363

  Welcome to Peaceful Pines, your cottage in the woods near the entrance to the Green Mountain National Forest. The charming two-bedroom cottage/camp was lovingly maintained. Key updates include a completely rebuilt chimney and masonry work, a wood stove ( in addition to baseboard heat) to take the chill out of those fall and winter evenings, T11 siding, a newer roof, and a private back deck with

  Jacki Murano Southern Vermont Realty Group

  1675 Vermont 9, Searsburg, VT 05363
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  /38

  $795,000

  • 4 Beds
  • 3.5 Baths
  • 4,104 Sq Ft

  25 Benson Fuller Dr, Bondville, VT 05340

  Where Mountains Meet Modern Living: Perched just moments from the energy of Stratton Mountain Resort, this contemporary mountain home reimagines what a Vermont getaway feels like. From the moment you step inside, the design does exactly what a great contemporary home should: it steps back and lets nature take center stage. Massive, soaring windows act as living art pieces, framing sweeping,

  Robin Apps Four Seasons Sotheby's Int'l Realty

  25 Benson Fuller Dr, Bondville, VT 05340
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  /25

  $550,000

  • 3 Beds
  • 2 Baths
  • 2,009 Sq Ft

  1625 Barnumville Rd, Manchester Center, VT 05255

  Offered for the first time in almost 40 years, this charming farmhouse is set on a picturesque 1.7 acre parcel of open land in Manchester, Vermont. Ideally located directly across from East of Equinox horse farm, the property offers a country setting just minutes from town.The main level features tall ceilings, a spacious kitchen with an adjoining dining area, and a generous living room

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  1625 Barnumville Rd, Manchester Center, VT 05255
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  /23

  $329,900

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,030 Sq Ft

  773 Oberdorf Rd, Readsboro, VT 05350

  Discover cozy mountain living in this charming Alpenwald chalet, where rustic character meets thoughtful modern updates. Nestled among the trees, this inviting retreat offers a bright, open floor plan filled with natural light from expansive windows and sliding glass doors. Recently remodeled, the kitchen and both full bathrooms bring a fresh, updated feel, while a comfortable bar area adds the

  Sean Taylor Moresi Real Estate Partners

  773 Oberdorf Rd, Readsboro, VT 05350
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  /16

  $204,000

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  112 Outwater Rd, Shaftsbury, VT 05262

  Enjoy the effortless flow and convenience of single-level living in this 3-bedroom, 2-bathroom manufactured home. Thoughtfully set back above the road on a private, expansive 1+ acre lot. A long driveway leads to the property, offering enhanced privacy and curb appeal. Inside, the inviting open floor plan is anchored by an expansive kitchen with abundant storage and a bright dining nook that

  Michaela Lawyer Brattleboro Area Realty

  112 Outwater Rd, Shaftsbury, VT 05262
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  /15

  $125,000

  • Land
  • 1.18 Acres
  • $105,932 per Acre

  510 Center St, Pownal, VT 05261

  Discover the potential of this scenic 1.18 acre parcel situated on a quiet street directly across from the town offices. Offering beautiful views and the convenience of town sewer, this property presents an excellent opportunity to build the home you've been dreaming of. Whether you're planning a year-round residence or a peaceful retreat, the generous lot provides plenty of space to create your

  Angela Bevin Maple Leaf Real Estate

  510 Center St, Pownal, VT 05261
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  /40

  $3,995,000

  $3M PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 6,500 Sq Ft

  515 W Fields Rd, Manchester, VT 05254

  Enduring values expressed in stone and wood! VERMONT CRAFTMANSHIP...A WORK OF ART!! Offering a private haven just minutes from downtown, in the heart of Manchester Village, nestled in the foothills of Equinox Mtn. is this rareand exceptional 5-bedroom, 6-bathroom home....The creative designof Architect Ramsey Gourd and Master Builder Mark Breen, well knownas two of Southern Vermont's

  Sunny Breen Josiah Allen Real Estate, Inc.

  515 W Fields Rd, Manchester, VT 05254
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  /39

  $975,000

  • 4 Beds
  • 3 Baths
  • 3,548 Sq Ft

  259 Beechnut Dr, Peru, VT 05152

  Beautiful Log Home on 4.23 Private Acres in PeruTucked away at the end of a quiet dead-end road, this beautiful log home offers privacy, space, and an ideal Vermont setting on 4.23 acres. Expansive views become even more impressive as the seasons change, and the home’s open floor plan is perfectly designed for entertaining family and friends.The main living level features a stunning

  Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

  259 Beechnut Dr, Peru, VT 05152
• 

  

  /31

  $185,000

  • 3 Beds
  • 1 Bath
  • 1,590 Sq Ft

  176 Glen Ave, Readsboro, VT 05350

  This classic, 1,590-square-foot, 3 bedroom, 1 bathroom home sits on a spacious 1.9-acre lot with plenty of potential, conveniently just 0.2 miles from Main Street in Readsboro. Located on a paved road, the house was built in 1880 and combines historic character with several important recent updates, including a new boiler, fresh interior paint, and the refinished wood floors throughout the inside

  Kim Meeker Southern Vermont Realty Group

  176 Glen Ave, Readsboro, VT 05350
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  /47

  $795,000

  $50K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 3,875 Sq Ft

  1629 Mann Hill Rd N, Pownal, VT 05261

  Facing west to capture breathtaking mountain views and unforgettable sunsets from nearly every room, this exceptional modern farmhouse seamlessly blends timeless character with thoughtful updates. Rich hardwood floors, cozy alcoves, and original beams in the living room create a warm and inviting atmosphere throughout. The spacious floor plan features five generously sized bedrooms, each with its

  Kelley Mccarthy Mahar McCarthy Real Estate

  1629 Mann Hill Rd N, Pownal, VT 05261
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  /10

  $245,000

  $97K PRICE DROP

  • Land
  • 28.5 Acres
  • $8,596 per Acre

  11 Old County Rd E, Londonderry, VT 05148

  A rare opportunity to own a wooded hillside property with potential southern and western views on a quiet country road in the much coveted village of Landgrove. Priced below the town assessment, the land is in current use, affording a tax savings, with a state permit for a 4-bedroom house. Enjoy all the elements of a Vermont country setting including a mix of mature hardwoods and softwoods,

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  11 Old County Rd E, Londonderry, VT 05148
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  /54

  $460,000

  $35K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,312 Sq Ft

  498 Townline Rd, Bennington, VT 05201

  If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the

  Betty McEnaney Diamond Realty

  498 Townline Rd, Bennington, VT 05201
• 

  

  /45

  $255,000

  $40K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  951 Gage St, Bennington, VT 05201

  This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

  Dan Mason Perrott Realty

  951 Gage St, Bennington, VT 05201
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  /60

  $735,000

  $64K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,420 Sq Ft

  2734 Mad Tom Rd, East Dorset, VT 05253

  Vermont's rustic charm will welcome you in a warm embrace every time you enter this custom built post and beam home on 37.5 private acres. The home features 2 bedrooms plus loft and 2 baths with tons of natural woodwork. The property also includes a detached post and beam garage with additional space above, perfect for an art studio, writer's workshop or plenty of extra storage. The property

  David Citron RE/MAX Four Seasons

  2734 Mad Tom Rd, East Dorset, VT 05253
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  /48

  $1,990,000

  • 4 Beds
  • 3.5 Baths
  • 3,844 Sq Ft

  209 Jack Cross Rd, Shaftsbury, VT 05262

  "Stone Meadows" a quintessential Vermont farmhouse set on more than 72 acres of rolling meadows, historic stone walls & peaceful countryside in Shaftsbury. Tucked along a quiet country road, this is the kind of property that captures the feeling so many people come to Vermont to find privacy, open land, character & and a home that feels connected to its surroundings. Serene and peaceful yet 17

  Carol O`Connor Four Seasons Sotheby's Int'l Realty

  209 Jack Cross Rd, Shaftsbury, VT 05262
• 

  

  /41

  $415,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,760 Sq Ft

  87 B Hill Rd, Pownal, VT 05261

  Vermont retreat nestled on 3.2 acres in the mountains of Pownal: "Gateway to Vermont". Right in the corner of NY and Mass, this Adirondack-style home offers the perfect blend of rustic charm, thoughtful craftsmanship, and everyday comfort.Surrounded by walking trails, blueberry and raspberry bushes, fruit trees, and abundant wildlife, the property is designed for those who appreciate the

  Lilli West Maple Leaf Real Estate

  87 B Hill Rd, Pownal, VT 05261
• 

  

  /31

  $1,200,000

  • 1 Bath
  • 950 Sq Ft

  109 Winhall Hollow Rd, Winhall, VT 05340

  Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  109 Winhall Hollow Rd, Winhall, VT 05340
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  /27

  $345,000

  $24K PRICE DROP

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

  686 Route 30, Dorset, VT 05251

  Village Mixed Use zoned Residence and Separate cottage located in the Hamlett of South Dorset...nearby Dorset's elementary School and Sheldon's Market. Conveniently located 3 miles from Manchester Ctr to the South or Dorset Village to the North. The main house offers 1350 SF, 2 bedrooms with overflow room, large closet, and sunroom entrance... The cottage is 675 SF with one bedroom and a

  Laura Beckwith Josiah Allen Real Estate, Inc.

  686 Route 30, Dorset, VT 05251
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  /32

  $765,000

  • 3 Beds
  • 3 Baths
  • 2,322 Sq Ft

  72 Benson Fuller Dr, Winhall, VT 05340

  Set among the trees just minutes from Stratton Resort, this spacious 3-bedroom, 3-bath mountain home combines beautiful views, flexible living spaces and plenty of room for family and friends. The dramatic main living area features soaring vaulted ceilings, warm wood accents, a floor-to-ceiling stone fireplace and an impressive wall of windows that fills the home with natural light and brings the

  Christine Chovan

  72 Benson Fuller Dr, Winhall, VT 05340
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  /38

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  51 Pageant St, Bennington, VT 05201

  There is something special about a home with character, and this charming 3BR property has it in abundance! Set in an established neighborhood within sight of the Mt. Anthony Country Club, this inviting home offers the warmth and craftsmanship of an earlier era combined with the comforts buyers are looking for. From the moment you arrive, the covered front porch welcomes you home. With generous

  Angela Bevin Maple Leaf Real Estate

  51 Pageant St, Bennington, VT 05201
• 

  

  /38

  $605,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,288 Sq Ft

  1 Beaver St, Bondville, VT 05340

  Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minutes to Bromley, and 12 minutes to Manchester, you’ll enjoy easy access to skiing, dining, shopping, and year-round recreation.Inside, the home features a spacious living room filled with natural light, creating a warm and

  Carrie Mathews Winhall Real Estate

  1 Beaver St, Bondville, VT 05340
• 

  

  /37

  $329,000

  $70K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,938 Sq Ft

  100 McCarthy Acres, North Bennington, VT 05257

  Nearly Lakefront Living in the Heart of North Bennington!Come for the space, stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

  Nicholas Charest Maple Leaf Real Estate

  100 McCarthy Acres, North Bennington, VT 05257
• 

  

  /32

  $549,000

  $50K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,234 Sq Ft

  202 Eagle Rise Rd Unit 16, Manchester Center, VT 05255

  This Eagle Rise Condo with three bedrooms and two & half baths is in an exclusive residential area accessed off scenic Manchester West Road. The Condo offers an open floor plan design, central air, propane baseboard hot water heat, hardwood floors and elevated deck. Recent improvements include new kitchen w/ granite counter tops, hickory cabinets with soft close drawers & doors, stainless steel

  David Halligan Four Seasons Sotheby's Int'l Realty

  202 Eagle Rise Rd Unit 16, Manchester Center, VT 05255
• 

  

  /40

  $1,325,000

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

  11 W Round Rd, Winhall, VT 05340

  11 Round Tree Road, Winhall, VT 05340A landmark on Round Tree Road, this house has inviting curb appeal with its stone façade and archway. With 1.83 acres the house has a very private setting in back for the patio, fire pit and hot tub. Unique U-shaped driveway has plenty of room for friends and family. Appropriately sized mud room for all the gear. Downstairs family room with fireplace and

  Andrew King Stratton Real Estate

  11 W Round Rd, Winhall, VT 05340
• 

  

  /59

  $899,900

  $40K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 3,974 Sq Ft

  145 White Farm Ln, Shaftsbury, VT 05262

  Nestled in a peaceful five acre setting just minutes from the shopping, dining, and everyday conveniences of both Bennington and Manchester, this beautifully maintained home offers privacy, comfort, and accessibility.Thoughtfully updated, this home offers a timeless, inviting style designed to feel welcoming for years to come. The newly renovated high end kitchen is both beautiful and

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  145 White Farm Ln, Shaftsbury, VT 05262

Showing Results 121 - 160, Page 4 of 7