Bennington County VT Homes for Sale

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  /55

  $2,950,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,762 Sq Ft

  59 Garden Loop Rd, Winhall, VT 05340

  Move into this brand new stunning custom contemporary set on over 3 acres in coveted Stratton ski country. This exceptional modern design offers elevated living with superior craftsmanship and sweeping endless views. Featuring four well appointed ensuites with polished baths boasting radiant heated floors, half bath, family room and dual laundry areas. The well designed kitchen with Italian

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  59 Garden Loop Rd, Winhall, VT 05340
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  /59

  $415,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft

  358 Birch Grove, Arlington, VT 05250

  Have you dreamed of a home on a quiet cul-de-sac with over an acre of land and seasonal mountain views? Look no further! Situated on a wooded lot in a very desirable neighborhood, this spacious home has all you need. Flooded with natural light, the large living room includes a gas fireplace, cozy reading nook, and cute sunroom that is perfect for plants. It leads to a wraparound deck, also

  Justine Curry Maple Leaf Realty

  358 Birch Grove, Arlington, VT 05250
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  /29

  $449,900

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  2121 North Rd, Arlington, VT 05250

  Beautifully maintained split-level home offering a wonderful combination of comfort, flexibility, and privacy! Situated on a large, one-acre private lot, the property features a circular driveway and loose-laid rock wall that frames the landscape with classic rural charm. The main level boasts an open-concept layout with gleaming hardwood floors throughout, a spacious living room, and a kitchen

  Matt Waddington Hoffman Real Estate

  2121 North Rd, Arlington, VT 05250
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  /6

  $199,900

  • 3 Beds
  • 2 Baths
  • 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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  /7

  $329,000

  • Land
  • 9.3 Acres
  • $35,376 per Acre

  1347 Morse Hill Rd, Dorset, VT 05251

  Discover the perfect blend of privacy and convenience with this 9.3 acre parcel situated in one of Southern Vermont's most desirable locations. Enjoy sweeping mountain views and peaceful surroundings just minutes from the charming and historic towns of Dorset and Manchester, known for boutique shopping, fine dining, and year-round cultural attractions. It's a short drive to skiing at Bromley,

  Deborah Hanst

  1347 Morse Hill Rd, Dorset, VT 05251
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  /7

  $29,000

  • Land
  • 1.2 Acres
  • $24,167 per Acre

  00 Oberdorf Rd, Stamford, VT 05350

  This 1.2 acre rectangular lot is located in Alpenwald Village! The village roads are community-maintained, have electricity service through Green Mountain Power Company and is loaded with recreational perks! 1.4 miles to hiking/ biking trails on the Dutch Hill Backcountry Area of the Green Mountain National Forest. 1.9 miles to an ATV & snowmobile trailhead in Heartwellville. Situated in the town

  Casey Scott Southern Vermont Realty Group

  00 Oberdorf Rd, Stamford, VT 05350
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  /2

  $125,000

  • Land
  • 1.45 Acres
  • $86,207 per Acre

  L/O River Rd, Winhall, VT 05340

  This 1.45+/- acre building lot offers a rare combination of privacy, recreation, and convenience. An approved Vermont wastewater permit for a 3-bedroom single-family home is already in place, streamlining the path toward building a year-round residence or mountain getaway. The property is located just one mile from the base of the Stratton Access Road and only twenty minutes from Manchester’s

  Cheyanne Pugliese

  L/O River Rd, Winhall, VT 05340
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  /10

  $150,000

  • Land
  • 4 Acres
  • $37,500 per Acre

  0 Rocky Ln Unit 5082777, Dorset, VT 05253

  'THE GROUND BENEATH AN APRIL SNOWSTORM IS NOT DORMANT... IT IS AWAKENING!".... Come discover the perfect opportunity to craft the home of your dreams!! With Spring ready to bloom, this very special lot is vibrant and quite ready for your vision!Fully permitted for a five bedroom residence, this property combines privacy, natural beauty and convenience!Imagine waking up to serene views,

  Sunny Breen Josiah Allen Real Estate, Inc.

  0 Rocky Ln Unit 5082777, Dorset, VT 05253
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  /8

  $9,999

  $6K PRICE DROP

  • Land
  • 1.2 Acres
  • $8,332 per Acre

  0 Alpendorf Ave, Readsboro, VT 05350

  Stake a claim on your own little piece of Vermont, at the foot of the Green Mountain National Forest. This 1.2-acre triangular lot rises up from the road and may allow peekaboo views of the surrounding valley starting in late-fall, once the region's famous foliage drops away. It's located in Alpenwald Village, with community-maintained roads rolling up and down the area's hilly topography. Today

  David White OwnerEntry.com

  0 Alpendorf Ave, Readsboro, VT 05350
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  /55

  $10,300,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 10,993 Sq Ft

  551 West Fields, Manchester, VT 05254

  Discover "the pinnacle of luxury living" in the heart of Manchester Village! Crafted by Breen Builders and Ramsay Gourd Architect, every detail reflects superior craftsmanship and timeless elegance! From the very foundation to the finishing touches, attention to detail and commitment to quality shine through! Experience the perfect blend of luxury and convenience in this stunning 10,000 sq.ft

  Sunny Breen Josiah Allen Real Estate, Inc.

  551 West Fields, Manchester, VT 05254
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  /4

  $18,000

  • Land
  • 1.1 Acres
  • $16,364 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 1-acre lot offers the perfect blend of privacy and convenience. Power is available at the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this opportunity to own a

  Colt Hazell Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
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  /8

  $1,900,000

  • Land
  • 199 Acres
  • $9,548 per Acre

  00 Vermont 11, Peru, VT 05152

  Bordering Green Mountain National Forest with southern exposure and views of Stratton Mountain and the surrounding Green Mountains, this 199 +/- acre offering in Peru, Vermont captures the scale, landscape, and natural beauty that define Southern Vermont mountain living.Rolling terrain, wooded ridgelines, and changing elevation create exceptional natural light, long-range mountain vistas, and

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  00 Vermont 11, Peru, VT 05152
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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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  /12

  $450,000

  • Land
  • 10.26 Acres
  • $43,860 per Acre

  4.1 Pearl Buck Dr, Winhall, VT 05340

  One of the last significant VIEW lots available on the mountain , with unrivaled 360 degree views, including dead on views of Stratton Mountain trails. The pinnacle of this 10.26 acre lot is deserving of an exceptionally designed and expansive home in this premium location with commanding views.Prime for a legacy property in a most desirable location, just 5 minutes to the Stratton Base Area,

  Kim Morgan-Wohler Wohler Realty Group

  4.1 Pearl Buck Dr, Winhall, VT 05340
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  /38

  $375,000

  • Land
  • 1.23 Acres
  • $304,878 per Acre

  0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340

  Exceptional offering. This premier parcel defines phase II of Ravenwood, an enclave of distinctive and premier mountain residences. This notable site offers extraordinary mountain views, direct access from Winhall Hollow Road and still enjoys all the benefits and amenities of The Ravenwood Neighborhood Association. Combining, privacy, natural beauty and convenience, this well-established

  Kim Morgan-Wohler Wohler Realty Group

  0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
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  /50

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  113 Main St, Bennington, VT 05201

  Charming downtown family home with modern upgrades.This beautifully updated 3-bedroom home is perfectly situated on a desirable corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, with a recent addition of a first-floor primary bedroom and new mudroom back entrance.Step inside to find gleaming hardwood floors and a warm, inviting layout. The dining

  Lindsey Martin Maple Leaf Realty

  113 Main St, Bennington, VT 05201
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  /21

  $299,999

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

  53 South Rd, East Arlington, VT 05252

  Welcome home to this inviting property that blends comfort, character, and everyday practicality. Set in a peaceful setting, this home offers bright living spaces, a functional layout, and room to relax and entertain. Whether you are enjoying quiet mornings with coffee or hosting friends and family, the space feels easy and welcoming, with thoughtful details throughout and convenient access to

  David White OwnerEntry.com

  53 South Rd, East Arlington, VT 05252
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  /45

  $365,000

  • 4 Beds
  • 1.5 Baths
  • 1,735 Sq Ft

  19 Royal St, North Bennington, VT 05257

  Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience—just steps from scenic hiking trails and close to Bennington College. Step inside to discover a freshly renovated kitchen and bathroom, complemented by new flooring throughout the

  Lindsey Martin Maple Leaf Realty

  19 Royal St, North Bennington, VT 05257
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  /45

  $299,900

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

  886 Hidden Valley Rd, Shaftsbury, VT 05262

  Escape to the rustic charm of this beautiful 5 bedroom, 2.5 bath log cabin nestled on 2 peaceful acres in the highly desirable town of Shaftsbury. From the moment you step inside, you’ll fall in love with the warm log features throughout, exposed beam ceilings, and the cozy fireplace that anchors the inviting living room. The charming country kitchen flows into a dedicated dining room, creating

  Julie Glover Mahar McCarthy Real Estate

  886 Hidden Valley Rd, Shaftsbury, VT 05262
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  /4

  $14,000

  • Land
  • 1.2 Acres
  • $11,667 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 1.2-acre lot offers the perfect blend of privacy and convenience. Power is already available on the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
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  /2

  $425,000

  • Land
  • 3 Acres
  • $141,667 per Acre

  lot B Frost Pond Rd, Dorset, VT 05251

  Private but not remote. Dorset West Road Location nearby Dorset and Manchester. Nice mountain views.Waste water permit in place for 5 BR, 8 person occupancy.

  Charles Mauro Josiah Allen Real Estate, Inc.

  lot B Frost Pond Rd, Dorset, VT 05251
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  /43

  $339,900

  • 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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  /30

  $275,000

  • 2 Beds
  • 2.5 Baths
  • 1,265 Sq Ft

  212 Dewey St, Bennington, VT 05201

  Move right in or continue operating as a short-term rental—this fully furnished 2-bedroom, 2.5-bath ranch offers comfort, convenience, and flexibility all in one package. Currently used as an Airbnb, all contents are included, making this a true turnkey opportunity. Inside, you’ll find recently refinished hardwood floors, and skylights that fill the home with natural light. A pellet stove for

  William Paquin Maple Leaf Realty

  212 Dewey St, Bennington, VT 05201
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  /42

  $250,000

  $50K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,952 Sq Ft

  569 Buck Hill Rd, Arlington, VT 05250

  Amazing 1850s farmhouse rich in old-world charm and character. Gleaming hardwood floors, large sun-filled rooms, and timeless architectural details throughout. Distinctive features include an elegant arched doorway, a unique library with octagonal bookshelves, and a striking turret that enhances the home’s historic appeal. The spacious primary bedroom stretches 25 feet and offers two separate

  Lisa Friedman Great American Dream Realty

  569 Buck Hill Rd, Arlington, VT 05250
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  /3

  $79,900

  • Land
  • 10.1 Acres
  • $7,911 per Acre

  0 Old County Ln, Readsboro, VT 05350

  Escape to the tranquil countryside of Readsboro with this stunning 10.10-acre parcel offering exceptional privacy and natural beauty. The property showcases a picturesque mix of open level areas and gentle rolling hills, complemented by mature apple and cherry trees, thriving blueberry bushes, and a charming brook that winds its way through the land.Whether you envision a full-time residence,

  Raelene Robinson-Garrow Real Broker LLC

  0 Old County Ln, Readsboro, VT 05350
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  /4

  $400,000

  • Land
  • 8.01 Acres
  • $49,938 per Acre

  248 French Hollow Rd, Winhall, VT 05340

  Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

  Kim Morgan-Wohler Wohler Realty Group

  248 French Hollow Rd, Winhall, VT 05340
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  /43

  $1,795,000

  $100K PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 5,178 Sq Ft

  144 Taconic Rd, Manchester, VT 05255

  “The Colonial” – Queen of Taconic Avenue One of the original summer “cottages” gracing historic Taconic Avenue, The Colonial is a crown jewel of Manchester Village. Painstakingly renovated, this stately home perfectly balances old-world charm with modern sophistication. The heart of the home is a stunning new chef’s kitchen, seamlessly blending timeless design with today’s comforts. All-new

  Sara Buckley Josiah Allen Real Estate, Inc.

  144 Taconic Rd, Manchester, VT 05255
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  /6

  $56,900

  $18K PRICE DROP

  • Land
  • 4.2 Acres
  • $13,548 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 4-acre lot offers the perfect blend of privacy and convenience. The property is partially cleared, making it easy to envision your dream home while still enjoying the natural beauty and tranquility of the surrounding forest. With power already available at the road and septic plans in place, much of the groundwork

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
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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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  /60

  $429,000

  • 4 Beds
  • 3 Baths
  • 2,119 Sq Ft

  131 Pine Cir, Bennington, VT 05201

  A must-see! Nestled in a quiet neighborhood just minutes from downtown dining and shopping, this beautifully maintained home offers comfort, flexibility, and thoughtful upgrades throughout. Completely renovated approximately 10 years ago, the home features a well-designed gourmet kitchen with granite countertops, a copper sink, soft-close cabinetry, and a custom built-in wine rack. French doors

  Thomas Martins Maple Leaf Realty

  131 Pine Cir, Bennington, VT 05201
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  /45

  $995,000

  $80K PRICE DROP

  • 13 Beds
  • 12 Baths
  • 8,594 Sq Ft

  2759 Vt Route 11, Peru, VT 05152

  Your private Vermont resort awaits! Perfect for multi-generational living or a co-ownership vacation compound, this 9.5-acre estate offers historic charm with massive capacity. Located minutes from premier skiing at Bromley, Stratton, and Magic. Highlights include, Main Residence: Beautifully renovated 1835 farmhouse with 4 beds, 3 baths, modern kitchen, and deck.Guest Wings: Two additions

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  2759 Vt Route 11, Peru, VT 05152
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  /60

  $4,995,000

  $255K PRICE DROP

  • 9 Beds
  • 10 Baths
  • 7,900 Sq Ft

  1184 E Manchester Rd, Manchester, VT 05255

  Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  1184 E Manchester Rd, Manchester, VT 05255
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  $199,000

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

  432 South St Unit D2, Bennington, VT 05201

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

  Abi Gregorio

  432 South St Unit D2, Bennington, VT 05201
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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
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  /52

  $2,285,000

  Open Sun 2PM - 4PM Coming Soon

  • 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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  /9

  $279,000

  $16K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 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

  $279,000

  $16K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 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. With

  Julie Glover Mahar McCarthy Real Estate

  124 S Branch St, Bennington, VT 05201
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  /21

  $125,000

  • Land
  • 4 Acres
  • $31,250 per Acre

  773 Shaftsbury Hollow Rd, Shaftsbury, VT 05262

  Set on 4 scenic acres in Shaftsbury Hollow, this special property offers a rare blend of open pasture, mature woodland, and frontage along the Little White Creek. The setting is both peaceful and recreational—ideal for those seeking a true Vermont escape. Enjoy natural shade along the water’s edge, spend summer days swimming or casting for brook trout, and gather around the campfire under the

  Jenifer Prouty Hoffman Hoffman Real Estate

  773 Shaftsbury Hollow Rd, Shaftsbury, VT 05262
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  /9

  $27,500

  • Land
  • 1.2 Acres
  • $22,917 per Acre

  0 Bergrucken Ln Unit 5044034, Stamford, VT 05352

  Trade city sirens for wind-rustled maples on this gently wooded 1.2-acre lot tucked inside Alpenwald Village. Alpenwald, although deed restricted, the light protective covenants keep the area tidy without cramping your architectural imagination. Think A-Frame, modern farmhouse, or a passive solar cottage. Beyond the lot is access to trails that lace through the Green Mountain National Forest.

  Kelly Agrillo Southern Vermont Realty Group

  0 Bergrucken Ln Unit 5044034, Stamford, VT 05352
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  /43

  $2,100,000

  • 4 Beds
  • 3 Baths
  • 3,780 Sq Ft

  1228 Skiparee Rd, Pownal, VT 05260

  Welcome to Amara Farm, an equestrian paradise in Southern Vermont. This meticulously planned property offers a 13-stall barn designed with every detail in mind, ensuring comfort and efficiency for both horse and rider. The state-of-the-art indoor arena features GGT footing and a full wall of window providing top-quality conditions for training and performance. Turnout paddocks and outdoor arena

  Christiane Carroccio TPW Real Estate

  1228 Skiparee Rd, Pownal, VT 05260

Showing Results 81 - 120, Page 3 of 6