Bennington County VT Homes for Sale

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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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  /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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  /41

  $1,425,000

  Open Sun 11AM - 2PM $100K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,931 Sq Ft

  932 Mcnamara Rd, Dorset, VT 05251

  Tucked away at the end of a gently curved, tree-lined drive, this exceptional contemporary home blends timeless elegance with Vermont charm. A welcoming paver patio leads to the informal entry, while a marble pathway guides you to the striking formal entrance and grand foyer. Inside, locally sourced marble floors flow into rich cherry hardwoods, setting the tone for quality throughout. Soaring

  Britt Wohler

  932 Mcnamara Rd, Dorset, VT 05251
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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
• 

  

  

  /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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  /38

  $309,900

  $15K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  2 Pine Rd, Bennington, VT 05201

  Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  2 Pine Rd, Bennington, VT 05201
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  /43

  $439,000

  • 4 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  96 Twitchell Hill Rd, Shaftsbury, VT 05262

  Some homes simply have a way of making you slow down. Built in 1863, the original Twitchell Farmhouse is one of them. Rich in history and craftsmanship, this beautifully maintained four-bedroom, 2.5-bath home offers the warmth and authenticity that only a true Vermont farmhouse can provide. Original hardwood floors, handcrafted woodwork by a master carpenter, and thoughtful updates create a home

  Daire Gibney Barrett and Valley Associates Inc.

  96 Twitchell Hill Rd, Shaftsbury, VT 05262
• 

  

  /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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  /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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  /37

  $289,000

  • 4 Beds
  • 2 Baths
  • 1,146 Sq Ft

  109 County St, Bennington, VT 05201

  Welcome to your like-new home in the heart of Bennington! Within easy walking distance of the vibrant downtown district, this beautifully renovated 4-bedroom, 2-bath New Englander has been completely transformed into a truly turnkey property. Nearly every aspect of the home has been updated, allowing you to enjoy the benefits of modern, low-maintenance living from day one.Extensive

  Angela Bevin Maple Leaf Real Estate

  109 County St, Bennington, VT 05201
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  /40

  $5,900,000

  $1M 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 design of 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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  /47

  $845,000

  • 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 stunning modern farmhouse seamlessly blends timeless character with thoughtful updates. Rich hardwood floors and cozy alcoves create warmth and charm throughout, while original beams in the living room add a touch of history and authenticity. The spacious layout offers 5 bedrooms, each with

  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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  /56

  $2,200,000

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

  312 Beartown Rd, Manchester Center, VT 05255

  Set on 24 private acres with sweeping mountain views, 312 Beartown Road offers a sense of complete escape while remaining moments from Manchester.Filled with natural light, the four-bedroom residence is thoughtfully designed to capture its extraordinary setting. Every room is oriented to the outdoors, with expansive windows that keep the Vermont landscape always in view. The chef's kitchen

  Christiane Carroccio TPW Real Estate

  312 Beartown Rd, Manchester Center, VT 05255
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  /38

  $775,000

  • 4 Beds
  • 4 Baths
  • 3,520 Sq Ft

  12 Stratton Ridge Rd, Winhall, VT 05340

  First time on the market, this spacious mountain home has been lovingly maintained by one family since it was built in 1980. Tucked away on a generous double lot at the dead end of a private road, the setting offers privacy along with a true Vermont feel—quiet and peaceful.Inside, the home features a bright, open layout with abundant natural light and warm woodwork throughout, creating an

  Carrie Mathews Winhall Real Estate

  12 Stratton Ridge Rd, Winhall, VT 05340
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  /54

  $495,000

  • 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
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  /12

  $299,999

  • Land
  • 10.05 Acres
  • $29,851 per Acre

  00 Garden Loop Rd, Winhall, VT 05340

  The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

  David White OwnerEntry.com

  00 Garden Loop Rd, Winhall, VT 05340
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  /45

  $275,000

  $20K 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
• 

  

  /31

  $1,200,000

  Open Fri 12:30PM - 2PM

  • 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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  /37

  $439,000

  • 3 Beds
  • 2.5 Baths
  • 2,389 Sq Ft

  15 Polygraphic Ln, North Bennington, VT 05257

  At the end of a quiet road in North Bennington, this beloved 1979 home is being offered for the first time by its original owner. Set on over an acre with a large private backyard, garden beds, wild blackberries, and a peaceful wooded backdrop, the property feels beautifully tucked away while remaining just a short walk to the Henry Bridge and the Walloomsac River. Inside, the home is timeless,

  Jenifer Prouty Hoffman Hoffman Real Estate

  15 Polygraphic Ln, North Bennington, VT 05257
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  /46

  $1,550,000

  • 5 Beds
  • 5 Baths
  • 6,129 Sq Ft

  1035 Holy Smoke Rd, Shaftsbury, VT 05262

  Experience the quintessential Vermont lifestyle in this masterfully renovated (2021) contemporary farmhouse, offering 6,100 sq. ft. of finished living space. Tucked at the end of a breathtaking maple-lined driveway, this 17± acre property offers panoramic mountain views and a private sanctuary for hiking, cross-country skiing, snowshoeing, and snowmobiling right from your door.The heart of

  Lori Hurley Four Corner Properties LLC

  1035 Holy Smoke Rd, Shaftsbury, VT 05262
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  /38

  $625,000

  • 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
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  /36

  $359,000

  $40K 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
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  /32

  $575,000

  $24K 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
• 

  

  /22

  $430,000

  • 5 Beds
  • 2 Baths
  • 1,664 Sq Ft

  13 Golden Triangle Rd, Winhall, VT 05340

  The ideal opportunity in a prime location, minutes from Stratton Mountain, Bromley Mountain, and the charming town of Manchester, this 5-bedroom, 2-bathroom home has what you need for your primary Vermont residence or a quiet place to getaway. The spacious living room and dining area is complimented by a wrap around porch. This home is low maintenance and setup well for those who want a

  Mike England Michael England Real Estate

  13 Golden Triangle Rd, Winhall, VT 05340
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  /42

  $349,000

  • 4 Beds
  • 2 Baths
  • 1,814 Sq Ft

  1153 King Hill Rd, Readsboro, VT 05350

  This recently updated 1920s Vermont farmhouse features 4 bedrooms, 2 full bathrooms, and a versatile loft space on just over 8 acres! Large, updated windows showcase mountain views and allow natural light to fill every room, highlighting the home's charming original details alongside modern updates. The first floor has two bedrooms, both full bathrooms, first floor laundry, as well as TWO

  Casey Scott Southern Vermont Realty Group

  1153 King Hill Rd, Readsboro, VT 05350
• 

  

  /56

  $925,000

  • 3 Beds
  • 4.5 Baths
  • 3,718 Sq Ft

  171 Mending Walls Rd, Manchester Center, VT 05255

  Looking for "NEW"? This residence is as close to new construction as it gets, having been thoughtfully gutted to the studs and tastefully renovated across all three levels. The stunning new quartz island kitchen features all new stainless appliances, new soft gray cabinetry, and an open-concept design flowing seamlessly into the dining room, living room and main-level office. A dramatic two-story

  Laura Beckwith Josiah Allen Real Estate, Inc.

  171 Mending Walls Rd, Manchester Center, VT 05255
• 

  

  /17

  $595,000

  Open Sun 11AM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,368 Sq Ft

  21 Jameson Flats Unit Duplex Unit B, Manchester, VT 05255

  THE PROGRAM: Purchase Price Assistance/ Mortgage Payment Reduction:Eligibility Requirements: * Vermont Residency or Residency at time of Purchase * First Time Vermont Homebuyer * Household Income at or Below $178,735* * Qualify for a Bank Mortgage * 10% Down Payment The developer will offer Gifted Equity and Paid Points at closing that will reduce the purchase price of the real estate and

  Britt Wohler

  21 Jameson Flats Unit Duplex Unit B, Manchester, VT 05255
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  /34

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,343 Sq Ft

  760 W Mountain Rd, Shaftsbury, VT 05262

  Tucked away in a private setting in Shaftsbury, this inviting home sits on 2.12 acres, offering both tranquility and convenience-just a short drive to both Manchester and Bennington. With 2,350 square feet of living space, the home features 3 bedrooms and 2.5 baths, thoughtfully designed for comfort and functionality. Many upgrades were completed in 2006, enhancing both efficiency and livability.

  Kelley Mccarthy Mahar McCarthy Real Estate

  760 W Mountain Rd, Shaftsbury, VT 05262
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  /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
• 

  

  /18

  $219,900

  • 3 Beds
  • 2 Baths
  • 1,372 Sq Ft

  420 Gore Rd, Bennington, VT 05201

  Welcome home to this charming 3-bedroom, 2-bath split-level home nestled on a beautiful 1-acre lot with stunning mountain views. Offering the perfect blend of comfort and privacy, this home features an attached garage, a spacious layout, and a peaceful backyard ideal for relaxing or entertaining.Enjoy your morning coffee or evening sunsets from one of two decks overlooking the private yard

  Kelley Mccarthy Mahar McCarthy Real Estate

  420 Gore Rd, Bennington, VT 05201
• 

  

  /21

  $750,000

  • 3,216 Sq Ft

  198 Elm St, Manchester Center, VT 05255

  Rare opportunity to own a well-maintained 4-unit property in the heart of Manchester, one of Southern Vermont’s most sought-after destinations. Offered at an attractive 8% cap rate, this unique investment features a charming 2-bedroom, 2-bath carriage house, two 2-bedroom, 1-bath units, and a 1-bedroom, 1-bath apartment, providing an appealing mix for a variety of tenants. Recent updates include

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  198 Elm St, Manchester Center, VT 05255
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  /33

  $1,100,000

  • 3 Beds
  • 2 Baths
  • 2,403 Sq Ft

  99 Holly's Way, Rupert, VT 05776

  Imagine waking to the quiet rhythm of the Vermont countryside, where morning light stretches across open meadows, woodland trails begin just beyond your door, and the pace of life slows to match the landscape. Set on 26 acres in Rupert, this exceptional property offers a rare combination of privacy, craftsmanship, and room to pursue the life you've imagined. The home is designed to feel connected

  Derryl Lang Four Seasons Sotheby's Int'l Realty

  99 Holly's Way, Rupert, VT 05776
• 

  

  /12

  $150,000

  $25K PRICE DROP

  • Land
  • 2.26 Acres
  • $66,372 per Acre

  0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

  Welcome to the Stratton Gardens Community. Build your Vermont home on this 2+ acre parcel in Stratton Gardens. Ease of access right off the Stratton Mountain Access Road, and all the amenities of Stratton Gardens Association- highlights include-Private Shuttle Bus service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water Permit in place for approved

  Tara van de Velde Four Seasons Sotheby's Int'l Realty

  0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
• 

  

  /25

  $950,000

  $300K PRICE DROP

  • 8,888 Sq Ft

  124 Elm St, Bennington, VT 05201

  An exceptional opportunity to own a prominent historic Victorian property in the heart of Bennington, offered as a residential or multifamily real estate asset only. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible residential and mixed-use potential within the Village of Bennington, subject to applicable municipal approvals. The main

  Marek Kovac TPW Real Estate

  124 Elm St, Bennington, VT 05201
• 

  /2

  $2,190,000

  • Land
  • 1.16 Acres
  • $1,887,931 per Acre

  301 Northside Dr, Bennington, VT 05201

  Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand

  Paul Carroccio TPW Real Estate

  301 Northside Dr, Bennington, VT 05201
• 

  

  /60

  $1,650,000

  • 3 Beds
  • 4 Baths
  • 2,872 Sq Ft

  36 Beaver St, Bondville, VT 05340

  Your Ultimate Vermont Mountain Retreat Awaits! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape—crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a 10-minute

  MaryKate Grey Stratton Real Estate

  36 Beaver St, Bondville, VT 05340
• 

  

  /29

  $210,000

  $40K PRICE DROP

  • 9 Beds
  • 5 Baths
  • 3,810 Sq Ft

  6982 Main St, Readsboro, VT 05350

  Prime location meets potential! Situated in the center of charming Readsboro, this 5-unit multi-family property offers a rare opportunity for investors and owner-occupants alike. Whether you're looking to expand your portfolio or live in one unit while generating rental income from the others, this property delivers. Some renovations needed – perfect for those looking to add value and

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  6982 Main St, Readsboro, VT 05350
• 

  

  /26

  $1,575,000

  • 3 Beds
  • 2.5 Baths
  • 3,264 Sq Ft

  777 McCooey Dr, Manchester Center, VT 05255

  Set back from a quiet country road in Manchester, Vermont, this spaciousFederal farmhouse style home offers a wonderful blend of comfort, privacyand Vermont charm. The classic white exterior with its attached red barncreates a welcoming first impression, while the home’s thoughtful designprovides plenty of space for everyday living, entertaining and enjoying thepeaceful

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

  777 McCooey Dr, Manchester Center, VT 05255

Showing Results 121 - 160, Page 4 of 7