Rupert, VT Homes

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  /41

  $399,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 2,294 Sq Ft

  4690 Route 153, Rupert, VT 05776

  This very special Vermont Contemporary is perched above the road on 10+ beautiful acres of gardens and park-like forest. The property is located on the east side of VT Rte 153 in Rupert, an unspoiled northwest corner of Bennington County. Start your day enjoying sunrise in the breakfast sunroom for morning coffee or tea, and enjoy the evening light on the west-facing screen porch listening to

  

  Kristin Comeau

  TPW Real Estate

  (802) 487-8165

  4690 Route 153, Rupert, VT 05776
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  /37

  $289,000 Sold Apr 18, 2025

  • 2,142 Sq Ft
  • $135/SF
  • 0 Days On Market

  • 8 Beds
  • 2.5 Baths
  • Built 1850

  771 Vermont 153, Rupert, VT 05776

  Come step back in time as you walk through this impressive 6 plus bedroom 4000+ square foot c1800 stately home awaiting restoration.  With gorgeous original floors, moldings, doors and fixtures all intact, upstairs high ceilings where legend has it there was once a  ballroom floating dance floor; this is one of Rupert’s historic pride and joys. And all set on 16 acres of beautiful level land with

  Scott McChesney McChesney RE, Inc.

  771 Vermont 153, Rupert, VT 05776
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  /22

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,708 Sq Ft

  16 Clark Rd, Rupert, VT 05776

  16 Clark Rd, Rupert, VT 05776
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  /29

  $549,000 Pending

  • 2 Beds
  • 2 Baths
  • 2,250 Sq Ft

  100 Holly's Way, Rupert, VT 05768

  Long driveway to a Private setting with lots of room to hike, hunt or just enjoy the peace and quite. Possible subdivision. House is warm and cozy with a large sleeping loft on the second loft. There is a foundation in place for an out building.

  Charles Mauro Josiah Allen Real Estate, Inc.

  100 Holly's Way, Rupert, VT 05768
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  /34

  $375,000 Sold Mar 31, 2025

  • 2,280 Sq Ft
  • $164/SF
  • 131 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1805

  2438 Route Vt 30, Rupert, VT 05761

  A Vermont home with a perfect blend and timeless appeal of a historic home and the conveniences of modern living. This charming home has endless possibilities, from restroration to a blank canvas to make it exactly the home you have always wanted.The home features a first-floor washer and dryer conveniently located in a spacious mudroom—perfect for keeping things tidy after spending time

  Flex Realty Group Flex Realty

  2438 Route Vt 30, Rupert, VT 05761
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  /40

  Est $369,144 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 2,552 Sq Ft

  151 Mill Rd, West Rupert, VT 05776

  151 Mill Rd, West Rupert, VT 05776
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  /49

  $245,000 Sold Feb 21, 2025

  • Land
  • 135 Acres
  • $1,815 per Acre

  • 72 Days On Market

  1000 Bear Mountain Camp Rd, Rupert, VT 05776

  An amazing get-away in the hills of the southern VT town of Rupert, these 135 +/- acres offer amazing mountain views, open fields, apple trees & a mature forest! Located at the end of a private, seasonal shared road, the property offers an ideal vacation getaway, hunting paradise or potential homesteader property with 2 +/- acres of open fields, 23 apple trees, 2 streams & a unique off-grid cabin

  Curtis Trousdale Preferred Properties

  1000 Bear Mountain Camp Rd, Rupert, VT 05776
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  /30

  Est $381,168 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,764 Sq Ft

  513 Sykes Hollow Rd, Pawlet, VT 05761

  513 Sykes Hollow Rd, Pawlet, VT 05761
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  /22

  $200,000 Sold Feb 07, 2025

  • 1,728 Sq Ft
  • $116/SF
  • 92 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2005

  61 East St, West Rupert, VT 05776

  Nestled in the Vermont village of Rupert this 3 bedroom, 2 bath home has all you need. Modular construction with large family room with pellet stove, large kitchen with island, dining room, living room, primary bedroom suite and more. Private back yard, front sitting porch and large unfinished basement. The attic space is insulated with a walk up and materials are left to begin finishing it if

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  61 East St, West Rupert, VT 05776
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  /8

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft

  115 Watrous Rd, Rupert, VT 05768

  115 Watrous Rd, Rupert, VT 05768
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  /38

  $356,000 Sold Jan 31, 2025

  • 1,225 Sq Ft
  • $291/SF
  • 51 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1964

  259 Watrous Rd, Rupert, VT 05776

  Mountain views and meadows surround this lovely cape on 2.30 acres just 6 miles from the Dorset Green. Well built two bedroom, two bath light filled home offers hardwood floors and updated kitchen with brand new stainless steel appliances. The oversized picture windows enhance the spectacular mountain views. The dining room features a gas stove or enjoying a cozy wood burning fire in the living

  Margretta Fischer Wohler Realty Group

  259 Watrous Rd, Rupert, VT 05776
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  /39

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 956 Sq Ft

  598 Sandgate Rd, Arlington, VT 05250

  598 Sandgate Rd, Arlington, VT 05250
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  /11

  $105,000 Sold Jan 14, 2025

  • Land
  • 11 Acres
  • $9,219 per Acre

  • 17 Days On Market

  0 Hebron Rd, Rupert, VT 05776

  This beautiful 11+ acre parcel of land offers the perfect blend of privacy, tranquility, and natural beauty in Vermont’s scenic landscape. With a mix of open meadowland and mature hardwoods, this property is ideal for anyone seeking a peaceful, off-the-grid lifestyle, nicely removed from the hustle and bustle of everyday life. Nestled along a quiet, town-maintained gravel road, this property

  Scott McChesney McChesney RE, Inc.

  0 Hebron Rd, Rupert, VT 05776
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  /40

  Est $633,337 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,580 Sq Ft

  229 Antone Mountain View Rd, Rupert, VT 05776

  229 Antone Mountain View Rd, Rupert, VT 05776
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  /2

  $100,000 Sold Nov 27, 2024

  • Land
  • 20 Acres
  • $5,000 per Acre

  • 436 Days On Market

  165 Ebenville Rd, Rupert, VT 05776

  Incredible quiet and privacy off a dead-end country road. 20 acres comprised of a south facing meadow, forest land, year round brook, orchards, views and incredible wildlife. Close to Merck Forest and access to an incredible network of snowmobile/hiking trails. A 40' Pilgrim Open Road trailer comes with the property.

  Paul Carroccio TPW Real Estate

  165 Ebenville Rd, Rupert, VT 05776
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  /28

  Est $285,728 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 740 Sq Ft

  425 Hidden Valley Rd, West Rupert, VT 05776

  425 Hidden Valley Rd, West Rupert, VT 05776
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  /5

  $230,000 Sold Nov 22, 2024

  • 1,296 Sq Ft
  • $177/SF
  • 0 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1972

  888 Ebenville Rd, Rupert, VT 05776

  Charming Vermont property with lots of potential! Nestled in the hills of Rupert Vermont on approximately 11.42 acres, this cape-style home built c1972 offers a cozy layout with two bedrooms one bath, and a great cathedral ceiling, living dining area with fireplace and sliders to the deck. The two shed outbuildings provide additional storage or workspace, perfect for a quiet retreat or hobbyist.

  Scott McChesney McChesney RE, Inc.

  888 Ebenville Rd, Rupert, VT 05776
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  /37

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 4,160 Sq Ft

  63 Sykes Hollow Rd, Rupert, VT 05776

  63 Sykes Hollow Rd, Rupert, VT 05776
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  /33

  $554,000 Sold Sep 20, 2024

  • 2,455 Sq Ft
  • $226/SF
  • 23 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1900

  404 Kent Hollow Rd, Rupert, VT 05776

  Your search is over! Finding a quintessential Vermont country homestead has its challenges and this property may be the whole package. This 1900 Farm House on 18.77 acres offers mountain views, open farmland, perennial gardens, specimen trees and a river running along the back border of the property (The White Creek). Additionally there is a 2 car detached garage with workshop area, loft

  Sara Buckley Josiah Allen Real Estate, Inc.

  404 Kent Hollow Rd, Rupert, VT 05776
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  /39

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,565 Sq Ft

  915 Vermont 153, Rupert, VT 05776

  915 Vermont 153, Rupert, VT 05776
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  /31

  $390,000 Sold Sep 12, 2024

  • 1,088 Sq Ft
  • $358/SF
  • 20 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2004

  1388 Pawlet Mountain Rd, Pawlet, VT 05761

  This home is perfectly situated where the lush meadow meets the mature rolling woodlands with majestic views of morning sunrises from the back deck and evening sunsets from the front deck. The panoramic views of the surrounding mountains and meandering hills and dales will make you never want to leave home. Built in 2003 this home has recently been updated with newer vinyl siding and a brand

  Suanne Ohl Northland Real Estate

  1388 Pawlet Mountain Rd, Pawlet, VT 05761
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  /39

  Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,700 Sq Ft

  4145 Route 153, Rupert, VT 05768

  4145 Route 153, Rupert, VT 05768
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  /40

  $465,465 Sold Aug 02, 2024

  • 3,342 Sq Ft
  • $139/SF
  • 4 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1836

  1081 Route 153, Rupert, VT 05776

  After more than 180 years the Hay family is parting with this beautiful West Rupert farmstead. This is a unique and special property blending village convenience, village commercial zoning, with 25A of incredible flat/tillable prime agricultural meadowland, a 5 bedroom colonial farmhouse, and a substantial 30x50 shop building with two solar arrays with a double Tesla Powerwall. The land and

  Scott McChesney McChesney RE, Inc.

  1081 Route 153, Rupert, VT 05776
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  /30

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,654 Sq Ft

  5491 Vt Route 315, Rupert, VT 05776

  5491 Vt Route 315, Rupert, VT 05776
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  /11

  $24,500 Sold Jun 28, 2024

  • Land
  • 0.20 Acre
  • $122,500 per Acre

  • 20 Days On Market

  0 Sandgate Rd, Rupert, VT 05776

  Roll up your sleeves and hang your hat… Here’s a great opportunity to pick up that Vemont getaway. Set on almost a quarter acre along a lightly traveled town gravel road is this four room camp needing to be cleaned out and fixed up. Ideal for “primitive camp” weekend getaway which would allow for a composting toilet and exterior water source (no inside plumbing). Great location – a couple miles

  Scott McChesney McChesney RE, Inc.

  0 Sandgate Rd, Rupert, VT 05776
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  /38

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,955 Sq Ft

  455 Pawlet Mountain Rd, Rupert, VT 05768

  455 Pawlet Mountain Rd, Rupert, VT 05768
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  /40

  $600,000 Sold May 17, 2024

  • 2,300 Sq Ft
  • $261/SF
  • 90 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2010

  592 Antone Mountain View Rd, Rupert, VT 05768

  Come experience this magical setting offering expansive views overlooking Merck Forest and Farmland to the east and distant sunset views to the west! The c. 2008 built house is set on +/- 10 acres off the end of a private gravel road for total privacy. Graced by stone walls and centuries old maples, this 4 bedroom, 3 bath home offers a slate floored entry, a dining room with pellet stove, an

  Scott McChesney McChesney RE, Inc.

  592 Antone Mountain View Rd, Rupert, VT 05768
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  /40

  Est $293,000 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,542 Sq Ft

  5932 Rt 153, Rupert, VT 05768

  5932 Rt 153, Rupert, VT 05768
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  /6

  $575,000 Sold May 15, 2024

  • Land
  • 49 Acres
  • $11,831 per Acre

  • 0 Days On Market

  152 Danforth Dr, Dorset, VT 05251

  Scott McChesney McChesney RE, Inc.

  152 Danforth Dr, Dorset, VT 05251
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  /40

  Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  2528 Vt Route 30, Rupert, VT 05768

  2528 Vt Route 30, Rupert, VT 05768
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  /33

  Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 5,956 Sq Ft

  166 McKeighan Rd, Rupert, VT 05776

  166 McKeighan Rd, Rupert, VT 05776
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  /20

  Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,979 Sq Ft

  2 Main St, Rupert, VT 05768

  2 Main St, Rupert, VT 05768
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  /35

  Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,600 Sq Ft

  89 Main St, Rupert, VT 05768

  89 Main St, Rupert, VT 05768
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  /39

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,654 Sq Ft

  5491 Vermont 315, Rupert, VT 05776

  5491 Vermont 315, Rupert, VT 05776
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  /40

  Est $422,597 Not Listed For Sale

  3923 Kent Hollow Rd, Rupert, VT 05776

  3923 Kent Hollow Rd, Rupert, VT 05776
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  /26

  Not Listed For Sale

  5251 Suncrest Rd, Rupert, VT 05768

  5251 Suncrest Rd, Rupert, VT 05768
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  /40

  Est $563,255 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,450 Sq Ft

  4075 Kent Hollow Rd, West Rupert, VT 05776

  4075 Kent Hollow Rd, West Rupert, VT 05776
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  /39

  Est $862,482 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,710 Sq Ft

  155 Rogers Rd, Dorset, VT 05251

  155 Rogers Rd, Dorset, VT 05251
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  /40

  Not Listed For Sale

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

  2774 Route 315, Pawlet, VT 05761

  2774 Route 315, Pawlet, VT 05761
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  /22

  Est $611,854 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,845 Sq Ft

  14 Sykes Hollow Rd, Pawlet, VT 05761

  14 Sykes Hollow Rd, Pawlet, VT 05761

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