Rupert, VT Homes

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  /27

  $625,000 Under Contract

  • Land
  • 170 Acres
  • $3,676 per Acre

  0 Suncrest Rd Unit 5075271, Rupert, VT 05768

  There's a rare 170 acres +- of agricultural and wooded land with mountain and valley views available... power along a portion of the 2700 feet of road frontage. The land supported cattle, corn and hay... There's a stream and an old apple orchard. This is a quiet stretch of road as Lewis Road bends to the right... Suncrest Road is straight ahead and the land is located on the left, north west side

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 397-9558

  0 Suncrest Rd Unit 5075271, Rupert, VT 05768
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  /60

  $1,300,000 Sold Dec 10, 2025

  694 Sykes Hollow Rd, Rupert, VT 05776

  • 3 Beds
  • 2.5 Baths
  • 2,259 Sq Ft
  • Built 1789

  Last Sold Summary

  • 2% Above List Price
  • $575/SF
  • 15 Days On Market

  Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

  694 Sykes Hollow Rd, Rupert, VT 05776
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  /49

  Not Listed For Sale

  1000 Bear Mountain Camp Rd, Rupert, VT 05776

  1000 Bear Mountain Camp Rd, Rupert, VT 05776

  Last Sold Summary

  • 72 Days On Market

  Last Sold Price $245,000

  Last Listing Agent Curtis Trousdale Preferred Properties
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  /50

  $259,000

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft

  3264 Route 153, West Rupert, VT 05776

  This neat and tidy single story home has been completely renovated from top to bottom, offering comfort, efficiency, and style. Updates include all new metal roof, vinyl siding, thermopane windows, propane hot-air heating system with heat pump central air conditioning, appliances, kitchen cabinets, counters, and hardwood flooring. Also updated plumbing, fiber optic internet, new electrical with a

  Scott McChesney McChesney RE, Inc.

  3264 Route 153, West Rupert, VT 05776
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  /56

  $405,000 Sold Dec 17, 2025

  130 Clark Rd, Pawlet, VT 05761

  • 4 Beds
  • 2 Baths
  • 2,120 Sq Ft
  • Built 1790

  Last Sold Summary

  • 3% Above List Price
  • $191/SF
  • 8 Days On Market

  Current Estimated Value $387,045

  Last Listing Agent Scott McChesney McChesney RE, Inc.

  130 Clark Rd, Pawlet, VT 05761
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  /22

  Not Listed For Sale

  16 Clark Rd, Rupert, VT 05776

  • 4 Beds
  • 4 Baths
  • 2,708 Sq Ft
  • Built 1989

  16 Clark Rd, Rupert, VT 05776

  Last Sold Summary

  • $240/SF
  • 19 Days On Market

  Last Sold Price $649,000

  Last Listing Agent Andrea Kaplan Four Seasons Sotheby's Int'l Realty
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  /47

  $455,555 Sold Oct 15, 2025

  380 Suncrest Rd, Rupert, VT 05776

  • 3 Beds
  • 2.5 Baths
  • 3,024 Sq Ft
  • Built 2005

  Last Sold Summary

  • 7% Above List Price
  • $151/SF
  • 9 Days On Market

  Last Listing Agent Dick Thackston R.H. Thackston & Company

  380 Suncrest Rd, Rupert, VT 05776
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  /31

  Est $424,716 Not Listed For Sale

  1388 Pawlet Mountain Rd, Pawlet, VT 05761

  • 1 Bed
  • 1 Bath
  • 1,088 Sq Ft
  • Built 2004

  1388 Pawlet Mountain Rd, Pawlet, VT 05761

  Last Sold Summary

  • 9% Above List Price
  • $358/SF
  • 20 Days On Market

  Last Sold Price $390,000

  Last Listing Agent Suanne Ohl Northland Real Estate
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  /37

  $289,000 Sold Apr 18, 2025

  771 Vermont 153, Rupert, VT 05776

  • 8 Beds
  • 2.5 Baths
  • 2,142 Sq Ft
  • Built 1850

  Last Sold Summary

  • $135/SF
  • 0 Days On Market

  Last Listing Agent Scott McChesney McChesney RE, Inc.

  771 Vermont 153, Rupert, VT 05776
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  /30

  Est $405,473 Not Listed For Sale

  513 Sykes Hollow Rd, Pawlet, VT 05761

  • 3 Beds
  • 1 Bath
  • 1,764 Sq Ft
  • Built 1930

  513 Sykes Hollow Rd, Pawlet, VT 05761

  Last Sold Summary

  • 20% Above List Price
  • $192/SF
  • 2 Days On Market

  Last Sold Price $338,500

  Last Listing Agent Donna Murray Varick Associates Ltd
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  /41

  $426,000 Sold Jun 04, 2025

  4690 Route 153, Rupert, VT 05776

  • 2 Beds
  • 2 Baths
  • 2,294 Sq Ft
  • Built 1985

  Last Sold Summary

  • 7% Above List Price
  • $186/SF
  • 52 Days On Market

  Last Listing Agent Kristin Comeau TPW Real Estate

  4690 Route 153, Rupert, VT 05776
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  /38

  Not Listed For Sale

  259 Watrous Rd, Rupert, VT 05776

  • 2 Beds
  • 2 Baths
  • 1,225 Sq Ft
  • Built 1964

  259 Watrous Rd, Rupert, VT 05776

  Last Sold Summary

  • $291/SF
  • 51 Days On Market

  Last Sold Price $356,000

  Last Listing Agent Margretta Fischer Wohler Realty Group
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  /54

  $660,000 Sold Nov 19, 2025

  1148 Kent Hollow Rd, West Rupert, VT 05776

  • 3 Beds
  • 2.5 Baths
  • 2,208 Sq Ft
  • Built 1985

  Last Sold Summary

  • 9% Below List Price
  • $299/SF
  • 40 Days On Market

  Current Estimated Value $672,553

  Last Listing Agent Margretta Fischer Wohler Realty Group

  1148 Kent Hollow Rd, West Rupert, VT 05776
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  /22

  Est $224,464 Not Listed For Sale

  61 East St, West Rupert, VT 05776

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 2005

  61 East St, West Rupert, VT 05776

  Last Sold Summary

  • 12% Above List Price
  • $116/SF
  • 92 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group
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  /29

  $435,000 Sold Jul 31, 2025

  100 Holly's Way, Rupert, VT 05768

  • 2 Beds
  • 2 Baths
  • 2,250 Sq Ft
  • Built 1991

  Last Sold Summary

  • 21% Below List Price
  • $193/SF
  • 278 Days On Market

  Last Listing Agent Charles Mauro Josiah Allen Real Estate, Inc.

  100 Holly's Way, Rupert, VT 05768
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  /5

  Est $289,613 Not Listed For Sale

  888 Ebenville Rd, Rupert, VT 05776

  • 2 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1972

  888 Ebenville Rd, Rupert, VT 05776

  Last Sold Summary

  • 26% Above List Price
  • $177/SF
  • 0 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Scott McChesney McChesney RE, Inc.
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  /59

  $300,000 Sold Oct 20, 2025

  3606 Kent Hollow Rd, Rupert, VT 05776

  • 2 Beds
  • 1 Bath
  • 890 Sq Ft
  • Built 1865

  Last Sold Summary

  • 11% Above List Price
  • $337/SF
  • 10 Days On Market

  Last Listing Agent Scott McChesney McChesney RE, Inc.

  3606 Kent Hollow Rd, Rupert, VT 05776
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  /33

  Est $574,140 Not Listed For Sale

  404 Kent Hollow Rd, Rupert, VT 05776

  • 5 Beds
  • 2 Baths
  • 2,455 Sq Ft
  • Built 1900

  404 Kent Hollow Rd, Rupert, VT 05776

  Last Sold Summary

  • 4% Above List Price
  • $226/SF
  • 23 Days On Market

  Last Sold Price $554,000

  Last Listing Agent Sara Buckley Josiah Allen Real Estate, Inc.
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  /34

  $375,000 Sold Mar 31, 2025

  2438 Route Vt 30, Rupert, VT 05761

  • 4 Beds
  • 1 Bath
  • 2,280 Sq Ft
  • Built 1805

  Last Sold Summary

  • 10% Below List Price
  • $164/SF
  • 131 Days On Market

  Last Listing Agent Flex Realty Group Flex Realty

  2438 Route Vt 30, Rupert, VT 05761
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  /40

  Not Listed For Sale

  1081 Route 153, Rupert, VT 05776

  • 5 Beds
  • 2.5 Baths
  • 3,342 Sq Ft
  • Built 1836

  1081 Route 153, Rupert, VT 05776

  Last Sold Summary

  • $139/SF
  • 4 Days On Market

  Last Sold Price $465,465

  Last Listing Agent Scott McChesney McChesney RE, Inc.
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  /22

  $180,000 Sold Jul 10, 2025

  3375 Rt 153, Rupert, VT 05761

  • 1 Bed
  • 1.5 Baths
  • 672 Sq Ft
  • Built 1975

  Last Sold Summary

  • $268/SF
  • 1 Day On Market

  Current Estimated Value $235,500

  Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group

  3375 Rt 153, Rupert, VT 05761
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  /6

  Not Listed For Sale

  152 Danforth Dr, Dorset, VT 05251

  152 Danforth Dr, Dorset, VT 05251

  Last Sold Summary

  • 0 Days On Market

  Last Sold Price $575,000

  Last Listing Agent Scott McChesney McChesney RE, Inc.
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  /25

  $290,000 Sold Feb 10, 2026

  942 Rt 315 Route, Rupert, VT 05768

  • Land
  • 26.5 Acres
  • $10,943 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 61 Days On Market

  Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.

  942 Rt 315 Route, Rupert, VT 05768
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  /40

  Not Listed For Sale

  592 Antone Mountain View Rd, Rupert, VT 05768

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • Built 2010

  592 Antone Mountain View Rd, Rupert, VT 05768

  Last Sold Summary

  • $261/SF
  • 90 Days On Market

  Last Sold Price $600,000

  Last Listing Agent Scott McChesney McChesney RE, Inc.
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  /39

  Not Listed For Sale

  598 Sandgate Rd, Arlington, VT 05250

  • 1 Bed
  • 1 Bath
  • 576 Sq Ft
  • Built 1967

  598 Sandgate Rd, Arlington, VT 05250

  Last Sold Summary

  • $495/SF
  • 30 Days On Market

  Last Sold Price $285,000

  Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.
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  /40

  Est $685,207 Not Listed For Sale

  229 Antone Mountain View Rd, Rupert, VT 05776

  • 3 Beds
  • 3 Baths
  • 2,580 Sq Ft
  • Built 2000

  229 Antone Mountain View Rd, Rupert, VT 05776

  Last Sold Summary

  • 5% Below List Price
  • $281/SF
  • 2 Days On Market

  Last Sold Price $725,000

  Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.
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  /37

  Not Listed For Sale

  63 Sykes Hollow Rd, Rupert, VT 05776

  • 3 Beds
  • 3.5 Baths
  • 3,060 Sq Ft
  • Built 2017

  63 Sykes Hollow Rd, Rupert, VT 05776

  Last Sold Summary

  • $433/SF
  • 4 Days On Market

  Last Sold Price $1,325,000

  Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.
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  /11

  Not Listed For Sale

  0 Hebron Rd, Rupert, VT 05776

  • 1 Bed
  • Built 1950

  0 Hebron Rd, Rupert, VT 05776

  Last Sold Summary

  • $140/SF
  • 17 Days On Market

  Last Sold Price $105,000

  Last Listing Agent Scott McChesney McChesney RE, Inc.
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  /39

  Not Listed For Sale

  915 Vermont 153, Rupert, VT 05776

  • 3 Beds
  • 1 Bath
  • 1,565 Sq Ft
  • Built 1905

  915 Vermont 153, Rupert, VT 05776

  Last Sold Summary

  • $61/SF
  • 105 Days On Market

  Last Sold Price $95,000

  Last Listing Agent Amy Hill EXP Realty
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  /40

  Est $317,000 Not Listed For Sale

  5932 Rt 153, Rupert, VT 05768

  • 4 Beds
  • 2 Baths
  • 2,542 Sq Ft
  • Built 1850

  5932 Rt 153, Rupert, VT 05768

  Last Sold Summary

  • 41% Above List Price
  • $89/SF
  • 260 Days On Market

  Last Sold Price $225,000

  Last Listing Agent Scott McChesney McChesney RE, Inc.
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  /11

  Not Listed For Sale

  0 Sandgate Rd, Rupert, VT 05776

  0 Sandgate Rd, Rupert, VT 05776

  Last Sold Summary

  • 20 Days On Market

  Last Sold Price $24,500

  Last Listing Agent Scott McChesney McChesney RE, Inc.
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  /35

  Not Listed For Sale

  89 Main St, Rupert, VT 05768

  • 5 Beds
  • 2 Baths
  • 2,600 Sq Ft
  • Built 1850

  89 Main St, Rupert, VT 05768

  Last Sold Summary

  • $106/SF
  • 850 Days On Market

  Last Sold Price $275,000

  Last Listing Agent David Shehadi Josiah Allen Real Estate, Inc.
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  /39

  Not Listed For Sale

  5491 Vermont 315, Rupert, VT 05776

  • 3 Beds
  • 2.5 Baths
  • 2,654 Sq Ft
  • Built 1905

  5491 Vermont 315, Rupert, VT 05776

  Last Sold Summary

  • $217/SF
  • 88 Days On Market

  Last Sold Price $575,000

  Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty
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  /40

  Est $434,219 Not Listed For Sale

  3923 Kent Hollow Rd, Rupert, VT 05776

  • Built 1850

  3923 Kent Hollow Rd, Rupert, VT 05776

  Last Sold Summary

  • 64% Above List Price
  • $96/SF
  • 145 Days On Market

  Last Sold Price $264,000

  Last Listing Agent Hughes Group Team Casella Real Estate
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  /40

  Est $384,764 Not Listed For Sale

  151 Mill Rd, West Rupert, VT 05776

  • 5 Beds
  • 4 Baths
  • 2,552 Sq Ft
  • Built 1900

  151 Mill Rd, West Rupert, VT 05776

  Last Sold Summary

  • 33% Above List Price
  • $114/SF
  • 98 Days On Market

  Last Sold Price $290,000

  Last Listing Agent Robin Chesnut-Tangerman McChesney RE, Inc.
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  /40

  Est $542,950 Not Listed For Sale

  4075 Kent Hollow Rd, West Rupert, VT 05776

  • 3 Beds
  • 2 Baths
  • 2,450 Sq Ft
  • Built 1826

  4075 Kent Hollow Rd, West Rupert, VT 05776

  Last Sold Summary

  • 22% Above List Price
  • $182/SF
  • 2 Days On Market

  Last Sold Price $445,000

  Last Listing Agent Scott McChesney McChesney RE, Inc.
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  /39

  Est $849,946 Not Listed For Sale

  155 Rogers Rd, Dorset, VT 05251

  • 4 Beds
  • 3 Baths
  • 2,710 Sq Ft
  • Built 1989

  155 Rogers Rd, Dorset, VT 05251

  Last Sold Summary

  • 24% Above List Price
  • $253/SF
  • 9 Days On Market

  Last Sold Price $685,000

  Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.
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  /8

  Not Listed For Sale

  115 Watrous Rd, Rupert, VT 05768

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 1980

  115 Watrous Rd, Rupert, VT 05768

  Last Sold Summary

  • $291/SF
  • 0 Days On Market

  Last Sold Price $669,000

  Last Listing Agent Scott McChesney McChesney RE, Inc.
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  /28

  Est $321,244 Not Listed For Sale

  425 Hidden Valley Rd, West Rupert, VT 05776

  • 2 Beds
  • 1 Bath
  • 740 Sq Ft
  • Built 2013

  425 Hidden Valley Rd, West Rupert, VT 05776

  Last Sold Summary

  • 19% Above List Price
  • $365/SF
  • 14 Days On Market

  Last Sold Price $270,000

  Last Listing Agent Margretta Fischer Wohler Realty Group
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  /38

  Est $461,644 Not Listed For Sale

  3427 Rupert Rd, West Rupert, VT 05776

  • 4 Beds
  • 2 Baths
  • 1,770 Sq Ft
  • Built 1968

  3427 Rupert Rd, West Rupert, VT 05776

  Last Sold Summary

  • 54% Above List Price
  • $169/SF
  • 9 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Michael Campbell Michael Craig Campbell Realty

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