Homes for Sale near Mt. Anthony Union Middle School

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  /35

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 1,580 Sq Ft

  134 Fox Hill Rd Unit PVT, Shaftsbury, VT 05262

  Welcome to the Fox Hill Community and a beautiful modern home tucked away on a private road in Shaftsbury, Vermont offering the perfect blend of privacy, comfort, and stunning Vermont scenery. The home offers 3 bedrooms and 3 bathrooms along with gorgeous mountain views. There is a cozy fireplace in the living room with ample space provided for a family, friends and entertaining. The landscaping

  

  Monique Geannelis

  Mahar McCarthy Real Estate

  134 Fox Hill Rd Unit PVT, Shaftsbury, VT 05262
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  /60

  $799,000

  Open Sun 12PM - 2PM $76K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,462 Sq Ft

  636 Dexter Rd, Shaftsbury, VT 05262

  The Dexter Road Farmhouse, Circa 1800In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic nearby backroads to write “Stopping by the Woods on a Snowy Evening." Dating back more than 225 years, this charming farmhouse offers a rare opportunity to own a piece of Vermont history while embracing the slower pace and natural beauty that define the region.

  

  Kristin Comeau

  TPW Real Estate

  636 Dexter Rd, Shaftsbury, VT 05262
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  /47

  $685,000

  • 3 Beds
  • 3 Baths
  • 3,153 Sq Ft

  262 Timber Trail Rd, Shaftsbury, VT 05262

  Vermont Home with Mountain, Meadow and Garden viewsNestled in the Green Mountains of Vermont, this 3 bedroom 3 bath home offers scenic views, open spaces, and the tranquility of Vermont living. Situated on three separately surveyed lots, the beautifully maintained property features Heirloom apple trees, park like forests and lush perennial gardens bursting with color throughout the

  

  Margretta Fischer

  Wohler Realty Group

  262 Timber Trail Rd, Shaftsbury, VT 05262
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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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  /33

  $349,000

  $26K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,911 Sq Ft

  21 Russett Dr, Bennington, VT 05201

  Tucked into a beautifully maintained neighborhood, 21 Russett Drive is the kind of home that feels welcoming the moment you arrive. Beautiful landscaping, a charming Dutch door, and a thoughtfully cared for yard give this property an almost secret garden feel private, inviting, and full of character.Inside, the versatility of this home truly shines. The main level offers a comfortable living

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  21 Russett Dr, Bennington, VT 05201
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  /7

  $55,000

  • Land
  • 22,215 Sq Ft
  • $107,843 per Acre

  24 Asa Way, Bennington, VT 05257

  Build your future in the heart of North Bennington at 24 Asa's Way. This 0.51 acre corner lot offers a rare opportunity to create a custom home in a well established neighborhood surrounded by beautifully maintained properties. With mountain views and underground utilities already in place, the setting combines natural beauty with modern convenience.Public water and sewer are available,

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  24 Asa Way, Bennington, VT 05257
• 

  

  /13

  $229,000

  • Land
  • 0 Sq Ft

  468 Skyboro Rd, Pownal, VT 05261

  Beautiful property featuring an impressive 835.9 feet of road frontage and over 10 partially cleared acres of private land in Pownal, Vermont. This land is situated on a private road with rolling woods, making it an ideal location to build a dream home or a vacation getaway. It offers easy access to Route 7, providing a quick drive north to the Bennington, Vermont area and local ski resorts.

  

  Sheryl Morehouse

  BISHOP WEST REAL ESTATE

  468 Skyboro Rd, Pownal, VT 05261
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  /5

  $55,000

  • Land
  • 20,908 Sq Ft
  • $114,583 per Acre

  29 Asa Way, Bennington, VT 05257

  Build your dream home at 29 Asa's Way, ideally situated at the top of the hill in a desirable North Bennington neighborhood. This 0.48 acre lot offers a level, build friendly setting with beautiful mountain views, providing the perfect backdrop for your future home.Public water and sewer are available, along with underground utilities, making for a smooth and efficient building process.

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  29 Asa Way, Bennington, VT 05257
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  /32

  $595,000

  • Land
  • 23.62 Acres
  • $25,191 per Acre

  3213 West Rd, Bennington, VT 05201

  Some properties offer acreage, some offer breathtaking views, very few offer both along with a rich history worth preserving and a future waiting to be imagined. For generations, this rare south-facing farm has looked across the valley enjoying sunlight from dawn until dusk & panoramic views that are exceptional! More than productive farmland, it became a place where neighbors and families

  

  Monique Geannelis

  Mahar McCarthy Real Estate

  3213 West Rd, Bennington, VT 05201
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  /38

  $299,000

  $26K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,829 Sq Ft

  89 Merson St, Woodford, VT 05201

  Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you’ll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026.What truly sets this property apart is its

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  89 Merson St, Woodford, VT 05201
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  /33

  $265,000

  $34K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft

  8 West St, Bennington, VT 05201

  Nestled in the heart of the charming North Bennington community, this lovingly maintained 3 bedroom, 1.5 bath home is ready for its next chapter. Recently refreshed with newly painted interiors, rejuvenated floors, updated electrical, a recently repointed foundation, and repointed chimney, this home blends classic character with thoughtful updates throughout.Enjoy the convenience of first

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  8 West St, Bennington, VT 05201
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  /36

  $198,000

  $22K PRICE DROP

  • Land
  • 54 Acres
  • $3,667 per Acre

  399 Bard Rd, Bennington, VT 05201

  Secluded serenity meets unmatched convenience on this sprawling 54+/- wooded acres in beautiful and historic Bennington, VT! Nestled among a lush mix of hard and softwoods teeming with wildlife, the property features a charming quarter-acre pond, perfect as a future homestead centerpiece, with your home set back just beyond the pond. Good access via a paved, town-maintained road leading to level

  Curtis Trousdale Preferred Properties

  399 Bard Rd, Bennington, VT 05201
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  /27

  $209,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,075 Sq Ft

  1083 Main St, Bennington, VT 05201

  Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  1083 Main St, Bennington, VT 05201
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  /39

  $479,000

  $60K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,065 Sq Ft

  262 Dwyers Camp Rd, Shaftsbury, VT 05262

  Well designed and newer home on 10.085 acres in Shaftsbury, VT. Offering 3 bedrooms, including main level primary bedroom and 2 full bathrooms. Cathedral ceiling formal dining room and modern kitchen with dining area and breakfast bar. Large living room with vaulted ceiling and lots of light. Main level laundry and rear mudroom finish the first floor. Upstairs there is a wonderful loft area, 2

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  262 Dwyers Camp Rd, Shaftsbury, VT 05262
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  /10

  $105,000

  $4K PRICE DROP

  • Land
  • 30.8 Acres
  • $3,409 per Acre

  0 Old Gale Hill Rd Unit 5099471, Shaftsbury, VT 05262

  30 acres of Vermont Heaven located on a private road just 20 minutes from the center of Shaftsbury . There is a mix of hardwoods, evergreens and wet lands around the pond. this is suitable for a dry camp. A slice paradise to get away to in the Green Mountains just steps away from the National Forest.

  Dan Mason Perrott Realty

  0 Old Gale Hill Rd Unit 5099471, Shaftsbury, VT 05262
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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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  /50

  $140,000

  $20K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,575 Sq Ft

  127 Dewey St, Bennington, VT 05201

  Opportunity awaits with this spacious property offering incredible potential for investors, renovators, or buyers looking to create their dream home. Currently configured as a single family residence, this home features 5 bedrooms and 2 bathrooms. At one point it was a 2 unit home and could potentially be again.Inside, you'll find generous living space ready for your vision and updates. A

  Lindsey Martin Maple Leaf Real Estate

  127 Dewey St, Bennington, VT 05201
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  /15

  $162,500

  $7K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 819 Sq Ft

  432 South St Unit A11, Bennington, VT 05201

  Enjoy easy first-floor, one-level living in this two-bedroom, one-and-a-half-bath condominium in Bennington’s Nathaniel Court community. The comfortable layout features an open living and dining area, a functional brand-new stainless steel kitchen appliances, laminate flooring, and plenty of natural light throughout. Both bedrooms offer inviting spaces, while the in-unit washer and dryer add

  Colt Hazell Flex Realty

  432 South St Unit A11, Bennington, VT 05201
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  /6

  $199,900

  • 1,176 Sq Ft

  2 Hamlin Ave, Bennington, VT 05201

  2-Unit Multi-Family with Professional-Grade Workshop!Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotive enthusiast,

  Lori Hurley Four Corner Properties LLC

  2 Hamlin Ave, Bennington, VT 05201
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  /12

  $49,000

  • Land
  • 9,147 Sq Ft
  • $233,333 per Acre

  2 Belvedere St, Bennington, VT 05201

  Here is the blank slate for your Vermont home, offering beautiful views of the Green Mountains and a location that is just steps from a 160-acre wildlife preserve with numerous hiking trails, wetland viewing platforms, and abundant wildlife. This cute corner lot is mostly level, cleared, and ready to build, with town water and sewer available at the street. Bring your imagination and come and

  Dan Mason Perrott Realty

  2 Belvedere St, Bennington, VT 05201
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  /15

  $65,000

  • Land
  • 17.3 Acres
  • $3,757 per Acre

  18 Hidden Valley Rd, Shaftsbury, VT 05262

  Ready to build 2.5 acre building lot with an aditional 14 acres of riding trails with wastewater permit for a 4 bedroom single family residence. Great potential for a pond site and the trails on the lot make it a great opportunity for a horse paddock.

  Dan Mason Perrott Realty

  18 Hidden Valley Rd, Shaftsbury, VT 05262
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  /22

  $435,000

  $64K PRICE DROP

  • 3,648 Sq Ft

  938 Vt Route 7a, Shaftsbury, VT 05262

  Strong income potential and a versatile unit mix make this 4-unit property an outstanding investment opportunity. The building features two 2-bedroom, 1-bath units, a spacious 3-bedroom, 1-bath unit, and a 1-bedroom, 1-bath apartment, appealing to a wide range of tenants. This well-positioned property offers dependable rental income and the flexibility that investors seek. Whether you're adding

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  938 Vt Route 7a, Shaftsbury, VT 05262
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  /53

  $1,695,000

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

  1944 Monument Ave, Bennington, VT 05201

  Set on 5.63 beautiful acres in one of Bennington's most desirable locations, this exceptional 1880 historic home has been thoughtfully renovated inside and out, blending timeless character with sophisticated modern amenities. The property includes approximately 3,200 square feet in the main residence, an attached two-car garage with a second kitchen, and a separate 1,000-square-foot one-bedroom

  Kelley Mccarthy Mahar McCarthy Real Estate

  1944 Monument Ave, Bennington, VT 05201
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  /2

  $75,000

  • Land
  • 11.2 Acres
  • $6,696 per Acre

  0 Mount Anthony Rd, Bennington, VT 05201

  A beautiful opportunity awaits on Mount Anthony Road in Bennington, Vermont-11.2 acres of wooded land nestled along a quiet, scenic dirt road. This property offers the perfect blend of seclusion and convenience, giving you the best of both worlds. Currently wooded, the land can be selectively cleared to reveal potential stunning views of the surrounding Vermont landscape. Imagine building a camp

  Kelley Mccarthy Mahar McCarthy Real Estate

  0 Mount Anthony Rd, Bennington, VT 05201
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  /11

  $169,900

  $10K PRICE DROP

  • 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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  /52

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  113 Main St, Bennington, VT 05201

  Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry.Step inside to find gleaming newly upgraded flooring, a warm and inviting

  Lindsey Martin Maple Leaf Real Estate

  113 Main St, Bennington, VT 05201
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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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  /43

  $319,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  683 Water St, North Bennington, VT 05257

  Much larger than it looks and completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much "like new". All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  683 Water St, North Bennington, VT 05257
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  /53

  $205,000

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  305 Weeks St, Bennington, VT 05201

  Experience refined living in this beautifully appointed tri-level townhouse-style condominium, ideally situated just moments from downtown, the hospital, shopping, and dining. Rich in vintage character while thoughtfully updated for modern living, this exceptional residence showcases elegant quartz and butcher block countertops, a designer tile backsplash, and striking marble flooring that create

  Lindsey Martin Maple Leaf Real Estate

  305 Weeks St, Bennington, VT 05201
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  /51

  $1,795,000

  • 3 Beds
  • 3 Baths
  • 5,228 Sq Ft

  2167 Myers Rd, Shaftsbury, VT 05262

  Welcome to Hidden Ponds Farm - a breathtaking retreat set on 40 sprawling acres where history and refined country living meet in perfect harmony. This extraordinary early 1800s post-and-beam converted barn has been thoughtfully reimagined, preserving its authentic character while seamlessly integrating modern comforts. A magnificent 1,000-foot hand-placed stone wall winds gracefully across the

  Kelley Mccarthy Mahar McCarthy Real Estate

  2167 Myers Rd, Shaftsbury, VT 05262
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  /50

  $330,000

  $15K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,750 Sq Ft

  1141 Burgess Rd, Bennington, VT 05201

  Completely renovated, turnkey single-level home offering mountain views, modern finishes, and a beautiful country setting. All major systems and cosmetic updates were completed within the last year, including a brand-new roof and new windows.The light-filled interior layout features 2 bedrooms, 2 full bathrooms, brand-new wood flooring across all main living areas, plush new bedroom

  Kate Barry EXP Realty

  1141 Burgess Rd, Bennington, VT 05201
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  /9

  $85,000

  • Land
  • 2.8 Acres
  • $30,357 per Acre

  0 W Mountain Rd, Shaftsbury, VT 05262

  Discover the possibilities offered by this 2.8±-acre wooded parcel in the desirable West Mountain Road area of Shaftsbury. Mature trees provide privacy and a peaceful country setting, while a level area within the property offers potential for a future homesite, subject to all required approvals. With selective clearing, the property may also offer beautiful mountain views. The lot features

  Jeffrey Dorman

  0 W Mountain Rd, Shaftsbury, VT 05262
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  /7

  $997,000

  • Land
  • 23,086 Sq Ft
  • $1,881,132 per Acre

  153 Northside Dr, Bennington, VT 05201

  Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for

  Lori Hurley Four Corner Properties LLC

  153 Northside Dr, Bennington, VT 05201
• 

  

  /9

  $269,000

  $26K PRICE DROP

  • 2,206 Sq Ft

  116 S Branch St Unit 118, Bennington, VT 05201

  Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

  Julie Glover Mahar McCarthy Real Estate

  116 S Branch St Unit 118, Bennington, VT 05201
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  /13

  $275,000

  $20K PRICE DROP

  • 2,022 Sq Ft

  124 S Branch St, Bennington, VT 05201

  Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups - perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street.

  Julie Glover Mahar McCarthy Real Estate

  124 S Branch St, Bennington, VT 05201
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  /8

  $199,000

  $51K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  924 Vt Route 7a, Shaftsbury, VT 05262

  Full of character and opportunity, this charming 2-bedroom, 2-bath home in Shaftsbury offers an affordable entry into homeownership or a fantastic addition to an investment portfolio. Once serving as the local post office, the property has a unique history and a cozy footprint that makes it ideal as a starter home, downsizing option, or rental property. Recent improvements include a beautifully

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  924 Vt Route 7a, Shaftsbury, VT 05262
• 

  

  /4

  $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
• 

  

  /60

  $999,000

  • 4 Beds
  • 3.5 Baths
  • 7,102 Sq Ft

  134 Grapevine Ln, Pownal, VT 05261

  Custom-built and truly exceptional, this phenomenal home is set on 5.81 wooded acres, offering privacy, space, and room for everyone. With 12 rooms, 4 bedrooms, and 4 bathrooms, this spacious home is designed for comfortable living and effortless entertaining. The first-floor primary suite features a beautiful private bath, and adjacent laundry room. The inviting family room offers cathedral

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  134 Grapevine Ln, Pownal, VT 05261
• 

  

  /42

  $180,000

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  105 Hicks Ave, Bennington, VT 05201

  Opportunity awaits at this unique property with an exceptional setting along the Walloomsac River. A true Vermont farmhouse offering three bedrooms and two bathrooms, situated on a flat, park-like lot with mature landscaping, open green space, and beautiful river frontage. The serene setting creates a peaceful atmosphere rarely found in properties with such versatile potential. A large barn

  Angela Bevin Maple Leaf Real Estate

  105 Hicks Ave, Bennington, VT 05201
• 

  

  /60

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 3,295 Sq Ft

  142 Schenkar Rd, Pownal, VT 05261

  Welcome to your own private oasis! Set on 30 private wooded acres, this well-maintained three-bedroom, 2.5-bath Colonial presents a rare opportunity to enjoy expansive acreage, exceptional mountain views (including the Bennington Battle Monument!), and peaceful surroundings in a highly versatile tri-state location near the Vermont, Massachusetts, and New York borders. The 2,083 square-foot home

  Erin McCormick KW Vermont

  142 Schenkar Rd, Pownal, VT 05261

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