Bennington, VT Homes

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  /21

  $249,000

  • Land
  • 3.42 Acres
  • $72,807 per Acre

  0 Havoc Hill, Dorset, VT 05253

  Tranquility and Adventure Await on Havoc Hill. Discover 3.42 plus private, wooded acres nestled atop storied Havoc Hill in charming East Dorset, Vermont. Known for its rugged beauty and historic ties to early Vermont logging and farming communities, Havoc Hill offers a rare opportunity to own land rich in character and natural serenity. Set off the picturesque Mad Tom Road, this secluded parcel

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  0 Havoc Hill, Dorset, VT 05253
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  /31

  $6,500 per month

  • 4 Beds
  • 3.5 Baths
  • 2,340 Sq Ft
  • House for Rent

  294 Green Peak Orchard S, Dorset, VT 05253

  Escape to a stunning summer/winter retreat in Southern Vermont, featuring 4 spacious bedrooms and 3.5 baths. Nestled in the heart of nature, this property offers breathtaking mountain views, perfect for relaxation and outdoor adventures. Open-concept living/kitchen area with plenty of seating, a wood burning fireplace, and panoramic mountain views. Kitchen is fully equipped with modern

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 644-7034

  294 Green Peak Orchard S, Dorset, VT 05253
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  /29

  $350,000 Sold Jun 10, 2025

  • 1,362 Sq Ft
  • $257/SF
  • 46 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1920

  297 Mad Tom Rd, East Dorset, VT 05253

  Adorable Cape-style gem nestled beside the enchanting Mad Tom Brook. This bright and sunny 1.5-story home captures the essence of Vermont living, natural beauty, timeless charm, and thoughtfully updated comfort. Step inside to discover a charming interior that blends classic New England character with modern upgrades. The newly updated kitchen is appointed with elegant soapstone countertops and

  Sandy Reavill Real Broker LLC

  297 Mad Tom Rd, East Dorset, VT 05253
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  /33

  Est $455,272 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,020 Sq Ft

  885 Mad Tom Rd, East Dorset, VT 05253

  885 Mad Tom Rd, East Dorset, VT 05253
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  /25

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  393 Morse Hill Rd, East Dorset, VT 05253

  This beautifully maintained home is now available for the first time in 40 years.On the main level, you will find a generously sized eat-in kitchen with granite countertops that opens to a dining room. There are two additional rooms on the main level: a large living room and a bedroom. The main floor also boasts French door that leads out to a spacious deck, perfect for overlooking the

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  393 Morse Hill Rd, East Dorset, VT 05253
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  /55

  $655,000 Sold Jun 02, 2025

  • 2,700 Sq Ft
  • $243/SF
  • 44 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1988

  214 S End Rd, East Dorset, VT 05253

  A River Runs Through It! This Conservationist’s dream is perched on a knoll above the meandering Otter Creek and borders the Green Mountain National Forest on the east and west. The original three-bedroom Cape-style home was built in 1988 and expanded with a post-and-beam addition in 1999, offering a Great Room with an exquisite fireplace, two additional bedrooms, an oversized

  Kristin Comeau TPW Real Estate

  214 S End Rd, East Dorset, VT 05253
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  /23

  Est $345,601 Not Listed For Sale

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

  352 S End Rd, Danby, VT 05739

  352 S End Rd, Danby, VT 05739
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  /40

  $479,000

  • 4 Beds
  • 3.5 Baths
  • 3,861 Sq Ft

  120 Village St, East Dorset, VT 05253

  Antique charmer in the village of East Dorset was originally built in the 1850s by famous lumberman, F.G. Harwood. An addition was added in 1900, followed by several improvements over time the colonial farmhouse boasts approximately 3,861 sq. ft. including an oversized two car garage all on 1.1 acres. With a sprawling footprint that features a primary bedroom suite with oversized closet, 4

  Jill Simon Josiah Allen Real Estate, Manchester Branch Office

  120 Village St, East Dorset, VT 05253
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  /45

  $593,000 Sold Mar 18, 2025

  • 2,986 Sq Ft
  • $199/SF
  • 99 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1860

  109 Mad Tom Rd, East Dorset, VT 05253

  Discover timeless charm blended with modern comfort in this enchanting 4-bedroom, 2-bath home nestled amidst Vermont's scenic beauty. This residence boasts a newly painted exterior with a classic wrap-around porch that invites you to enjoy leisurely moments soaking in East Dorset's small town lifestyle complete with restored marble sidewalks. Step inside to a welcoming parlor where wood flooring

  Julie Citron RE/MAX Four Seasons

  109 Mad Tom Rd, East Dorset, VT 05253
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  /38

  Est $661,980 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,678 Sq Ft

  96 Mount Aeolus Ln, East Dorset, VT 05253

  96 Mount Aeolus Ln, East Dorset, VT 05253
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  /7

  $410,000 Sold Nov 23, 2024

  • Land
  • 5 Acres
  • $78,695 per Acre

  • 14 Days On Market

  737 Squirrel Hollow Rd, Dorset, VT 05253

  --- Premiere Building Lot with Driveway Built and Septic Installed --- Just minutes to Manchester and Dorset, this 5.21-acre building lot offers breathtaking mountain views and a peaceful Vermont setting. The property has been thoughtfully cleared, the driveway built and the septic system installed. Currently permitted for a 4BR main house with 1BR guest house, this septic system has the capacity

  Cheyanne Pugliese

  737 Squirrel Hollow Rd, Dorset, VT 05253
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  /37

  Est $309,574 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,412 Sq Ft

  188 Benedict Rd, East Dorset, VT 05253

  188 Benedict Rd, East Dorset, VT 05253
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  /26

  $275,000 Sold Aug 22, 2024

  • 1,964 Sq Ft
  • $140/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  392 S End Rd, East Dorset, VT 05253

  Discover the charm of countryside living with this exquisite property, a perfect blend of comfort and convenience. Nestled in a serene location, this home offers a unique chance to own a piece of tranquility. The residence boasts three well-proportioned bedrooms and two expansive bathrooms, providing ample space for relaxation and privacy. The walk-in basement is a testament to fine

  Eric Hier Northland Real Estate

  392 S End Rd, East Dorset, VT 05253
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  /16

  Est $525,046 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,129 Sq Ft

  85 Benedict Rd, East Dorset, VT 05253

  85 Benedict Rd, East Dorset, VT 05253
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  /31

  Est $730,770 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,592 Sq Ft

  161 Dorset Hill Rd, East Dorset, VT 05253

  161 Dorset Hill Rd, East Dorset, VT 05253
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  /19

  Est $453,843 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,168 Sq Ft

  255 Mad Tom Rd, East Dorset, VT 05253

  255 Mad Tom Rd, East Dorset, VT 05253
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  /40

  Est $851,500 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,050 Sq Ft

  425 Green Peak Orchard Rd, Dorset, VT 05253

  425 Green Peak Orchard Rd, Dorset, VT 05253
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  /40

  Est $1,570,392 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,480 Sq Ft

  167 Green Peak Orchard Rd N, Dorset, VT 05253

  167 Green Peak Orchard Rd N, Dorset, VT 05253
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  /20

  Not Listed For Sale

  Lots 7,8,9 Birchstone Ln, Dorset, VT 05253

  Lots 7,8,9 Birchstone Ln, Dorset, VT 05253
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  /35

  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,400 Sq Ft

  1902 Dorset Hill Rd, Dorset, VT 05253

  1902 Dorset Hill Rd, Dorset, VT 05253
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  /5

  Est $309,135 Not Listed For Sale

  • 2 Beds

  216 Village St, East Dorset, VT 05253

  216 Village St, East Dorset, VT 05253
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  /40

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,107 Sq Ft

  103 Read Farm Ln, Dorset, VT 05253

  103 Read Farm Ln, Dorset, VT 05253
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  /5

  Est $285,292 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  104 Morse Hill Rd, East Dorset, VT 05253

  104 Morse Hill Rd, East Dorset, VT 05253
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  /37

  Not Listed For Sale

  0 Dorset Hill Rd Unit 4902662, Dorset, VT 05253

  0 Dorset Hill Rd Unit 4902662, Dorset, VT 05253
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  /6

  Not Listed For Sale

  Lot 12 Birchstone Ln, Dorset, VT 05253

  Lot 12 Birchstone Ln, Dorset, VT 05253
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  /37

  Est $1,473,783 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 5,236 Sq Ft

  202 Uphill Ln, East Dorset, VT 05253

  202 Uphill Ln, East Dorset, VT 05253
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  /40

  Not Listed For Sale

  • 4 Beds
  • 7 Baths
  • 4,198 Sq Ft

  768 Sleighbell Ln, Dorset, VT 05253

  768 Sleighbell Ln, Dorset, VT 05253
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  /25

  Est $1,274,424 Not Listed For Sale

  • 5 Beds
  • 1.5 Baths
  • 2,400 Sq Ft

  1532 Morse Hill Rd, East Dorset, VT 05253

  1532 Morse Hill Rd, East Dorset, VT 05253
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  /19

  Est $773,905 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,447 Sq Ft

  227 Birchstone Ln, East Dorset, VT 05253

  227 Birchstone Ln, East Dorset, VT 05253
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  /40

  Est $762,394 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,577 Sq Ft

  239 Birchstone Ln, East Dorset, VT 05253

  239 Birchstone Ln, East Dorset, VT 05253
• 

  

  /33

  Est $1,003,287 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,246 Sq Ft

  121 Birchstone Ln, East Dorset, VT 05253

  121 Birchstone Ln, East Dorset, VT 05253
• 

  

  /19

  Est $310,618 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,032 Sq Ft

  45 Pleasant Street Extension, East Dorset, VT 05253

  45 Pleasant Street Extension, East Dorset, VT 05253
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  /21

  Est $408,478 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,576 Sq Ft

  386 Benedict Rd, East Dorset, VT 05253

  386 Benedict Rd, East Dorset, VT 05253
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  /40

  Est $439,636 Not Listed For Sale

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

  191 Pleasant Street Extension, East Dorset, VT 05253

  191 Pleasant Street Extension, East Dorset, VT 05253
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  /40

  Est $349,714 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,000 Sq Ft

  26 Overlook Rd, East Dorset, VT 05253

  26 Overlook Rd, East Dorset, VT 05253
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  /10

  Est $489,370 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  56 Pleasant Street Extension, East Dorset, VT 05253

  56 Pleasant Street Extension, East Dorset, VT 05253
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  /24

  Est $359,189 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,652 Sq Ft

  358 Benedict Rd, East Dorset, VT 05253

  358 Benedict Rd, East Dorset, VT 05253
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  /40

  Est $705,717 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,896 Sq Ft

  49 Morse Hill Rd, East Dorset, VT 05253

  49 Morse Hill Rd, East Dorset, VT 05253
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  /40

  Est $3,247,873 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 5,081 Sq Ft

  779 Wind Hill Rd, Dorset, VT 05251

  779 Wind Hill Rd, Dorset, VT 05251
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  /6

  Not Listed For Sale

  lot 11 Birchstone Ln, Dorset, VT 05253

  lot 11 Birchstone Ln, Dorset, VT 05253

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