Windsor, VT Homes

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  /30

  $455,000

  • 3 Beds
  • 1.5 Baths
  • 1,582 Sq Ft

  7873 Pomfret Rd, North Pomfret, VT 05053

  Great location to both historic Woodstock and the Upper Valley. This charming cape has lots of antique characteristics with original wood floors and accented with hand hewn beams. The second floor was expanded with taller ceiling height, new windows and insulation. Kitchen flows to a large dining room with half bath and laundry on first floor. Large sunlit living room off the North end of the

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  7873 Pomfret Rd, North Pomfret, VT 05053
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  /40

  $731,250 Sold Jun 18, 2025

  • 2,390 Sq Ft
  • $306/SF
  • 0 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1944

  519 Cherry Hill Rd, Pomfret, VT 05084

  Imagine waking up to a view of the quintessential picture postcard of Vermont; rolling hills and a white church steeple in the valley below! This is the scene at Cherry Hill Chalet in beautiful N. Pomfret, located just 20 minutes from the Village of Woodstock and 25 minutes to Hanover, NH. Access to both I89 and I91 are also less than 30 minutes away. The Chalet is rich in local history and was

  David Donegan Snyder Donegan Real Estate Group

  519 Cherry Hill Rd, Pomfret, VT 05084
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  /14

  Est $278,190 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,088 Sq Ft

  1416 Allen Hill Rd, Pomfret, VT 05068

  1416 Allen Hill Rd, Pomfret, VT 05068
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  /37

  $699,000

  • Land
  • 52 Acres
  • $13,365 per Acre

  00 Granite Ledge, Pomfret, VT 05059

  Pristine Pomfret land with view of Ascutney! Build your dream home on this unspoiled parcel in one of Pomfret's most beautifully preserved and scenic locales. Surrounded by large landholdings and conserved farmland, but only ten minutes from Woodstock and with excellent access to Route 4 and Quechee, this land comprises historic rock walls, mature hardwoods, a stream, and offers the potential for

  Keri Cole Williamson Group Sothebys Intl. Realty

  00 Granite Ledge, Pomfret, VT 05059
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  /54

  $1,500,000 Sold Jun 09, 2025

  • 3,012 Sq Ft
  • $498/SF
  • 68 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1971

  22 Orchard Hill Rd, Woodstock, VT 05091

  LICHENVALE at 22 Orchard Hill Road in Pomfret is a traditional Royal Barry Wills designed cape situated to capture sweeping views south down the Pomfret Valley to Mt. Tom, and the hills surrounding Woodstock Village. The well-cared for dwelling is naturally landscaped with mature gardens, and stone walls and sited on a level plateau at the margins of an open meadow below and the forested hillside

  Laird Bradley Williamson Group Sothebys Intl. Realty

  22 Orchard Hill Rd, Woodstock, VT 05091
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  /29

  Est $616,211 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,105 Sq Ft

  104 Stage Rd, South Pomfret, VT 05067

  104 Stage Rd, South Pomfret, VT 05067
• 

  

  /36

  $846,000

  • 3 Beds
  • 3.5 Baths
  • 1,840 Sq Ft

  49 Vt Rt 12, Pomfret, VT 05053

  Discover the possibilities with this beautifully crafted three bedroom, three and one half bath home and versatile Post and Beam barn/studio, set between Woodstock and Silver Lake in scenic Barnard. The main residence features an airy great room with vaulted ceilings, warm wood accents, and expansive windows that invite natural light and frame peaceful views. Thoughtful design and quality

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  49 Vt Rt 12, Pomfret, VT 05053
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  /40

  $1,850,000 Sold Jun 06, 2025

  • 3,336 Sq Ft
  • $555/SF
  • 0 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1970

  109 Windy Ln, Pomfret, VT 05067

  Windy Lane is nestled on 68 very private acres- with stunning mountains views overlooking a large pond stocked with trout for those fishing enthusiast. Expansive stone waterfall accents the swimming pond with a unique stone diving board and sandy beach for easy access to swim. Approx. 30 acres of open land, rolling meadows, antique stonewalls and exceptional perennials gardens. The main house

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  109 Windy Ln, Pomfret, VT 05067
• 

  

  /40

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 4,309 Sq Ft

  738 Stage Rd, South Pomfret, VT 05067

  738 Stage Rd, South Pomfret, VT 05067
• 

  

  /40

  $700,000 Sold Jun 03, 2025

  • 4,142 Sq Ft
  • $169/SF
  • 137 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1805

  8754 Pomfret Rd, Pomfret, VT 05084

  PRICES ARE FALLING WITH THOSE GORGEOUS LEAVES! Discover the perfect blend of vintage charm and modern amenities at The Rabbit Run Farm, a stunning 1805 farmhouse offering a lifestyle of comfort and elegance. This beautiful property features comfortably sized rooms filled with natural sunlight, showcasing the timeless appeal of classic architecture.A large addition provides a main bedroom

  Katie Ladue Gilbert KW Vermont Woodstock

  8754 Pomfret Rd, Pomfret, VT 05084
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  /17

  Est $1,413,068 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 4,860 Sq Ft

  2564 Stage Rd, South Pomfret, VT 05067

  2564 Stage Rd, South Pomfret, VT 05067
• 

  

  /22

  $775,000 Sold May 14, 2025

  • Land
  • 248 Acres
  • $3,121 per Acre

  • 77 Days On Market

  0 Stage Rd Unit 5030262, Pomfret, VT 05067

  A kingdom size 248 acres straddling hilltops connecting the towns of Pomfret and Barnard! Truly a parcel of a dynamic scope that would typically only be found in the more rural of locations! However, the numerous well known amenities of Woodstock Village are only 4.5 miles and just a few minutes away! Skiing at Saskadena 6 is little more than a mile away! The current owners who wisely assembled

  John Wetmore Wetmore Real Estate

  0 Stage Rd Unit 5030262, Pomfret, VT 05067
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  /40

  Est $923,829 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 2,743 Sq Ft

  737 Skyline Dr, Pomfret, VT 05068

  737 Skyline Dr, Pomfret, VT 05068
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  /56

  $3,250,000 Sold Apr 15, 2025

  • 3,100 Sq Ft
  • $1048/SF
  • 221 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1850

  501 Galaxy Hill Rd, North Pomfret, VT 05053

  MAPLE LANE FARM - With a sweeping, maple-lined drive, this property holds court in one of Pomfret's most beautiful neighborhoods. Seven perennial gardens offer beauty in every season - from the "Secret Shade Garden" (created during Covid spring) to the two 100' perennial borders to the "Dwarf Conifer Garden" (how they GREW!) - and nothing is more peaceful than a walk through the Paper Birch

  Keri Cole Williamson Group Sothebys Intl. Realty

  501 Galaxy Hill Rd, North Pomfret, VT 05053
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  /37

  Est $1,046,844 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,344 Sq Ft

  1075 Barber Hill Rd, Woodstock, VT 05091

  1075 Barber Hill Rd, Woodstock, VT 05091
• 

  

  /11

  $266,000 Sold Feb 14, 2025

  • Land
  • 38 Acres
  • $6,982 per Acre

  • 222 Days On Market

  00 Allen Hill Rd, Pomfret, VT 05068

  38.1 acres of wooded land with frontage on Allen Hill Road. A cleared area at the height of the land provides beautiful long distance views of local countryside and distant mountains. Two year round streams meander through the property. For many years the property had been used as the site for the Bogburn Cross Country Ski Race where upwards of 200 skiers would participate. The extensive trails

  Stan Butler Four Seasons Sotheby's Int'l Realty

  00 Allen Hill Rd, Pomfret, VT 05068
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  /40

  Est $721,920 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,128 Sq Ft

  167 Limey Ln, Pomfret, VT 05053

  167 Limey Ln, Pomfret, VT 05053
• 

  

  /25

  $525,000 Sold Jan 31, 2025

  • Land
  • 22 Acres
  • $23,864 per Acre

  • 151 Days On Market

  0 Skyline Dr, Pomfret, VT 05053

  Rare opportunity to build your dream home on 22 magical acres on highly coveted Skyline Drive in Pomfret, VT. “Laughing Winds” has been lovingly stewarded by the same family for 24 years. The land was expertly sculpted to reveal beautiful long-range views which can easily be expanded on with minor clearing. The house site area and roughed-in semi-circular drive have been protected from the road

  Dan Noble Snyder Donegan Real Estate Group

  0 Skyline Dr, Pomfret, VT 05053
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  /40

  Est $670,730 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,100 Sq Ft

  243 White River Ln, Pomfret, VT 05084

  243 White River Ln, Pomfret, VT 05084
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  /8

  $575,000 Sold Dec 10, 2024

  • Land
  • 67 Acres
  • $8,627 per Acre

  • 167 Days On Market

  2568 Pomfret Rd, South Pomfret, VT 05067

  The 66-acre property is very privately sited high on a bluff with beautiful mountain views within 10 minutes of Woodstock. A quarter mile driveway crosses a stream and ends in a big meadow with 180-degree views, including Saskadena Six Ski Area. The c1970’s residence and barn with apartment are in poor condition. There is power, well and septic at the site. The property is being sold “As-Is”.

  Story Jenks LandVest, Inc/Woodstock

  2568 Pomfret Rd, South Pomfret, VT 05067
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  /6

  Est $67,532 Not Listed For Sale

  1092 Sessions Meadow, Woodstock, VT 05091

  1092 Sessions Meadow, Woodstock, VT 05091
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  /40

  $495,200 Sold Oct 28, 2024

  • 1,040 Sq Ft
  • $476/SF
  • 9 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1946

  474 Stage Rd, South Pomfret, VT 05067

  Charming Country Cape in a prime location. Step into this delightful home through an inviting mudroom that leads to a custom-designed kitchen with Ditra heated floors accented with modern drawer refrigeration and soap stone finishes. The main level is bathed in natural light, featuring hardwood floors and a cozy living room with a woodstove to warm your winter evenings. Upstairs, three vibrant

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  474 Stage Rd, South Pomfret, VT 05067
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  /13

  Not Listed For Sale

  00 Twin Pond Rd, Pomfret, VT 05068

  00 Twin Pond Rd, Pomfret, VT 05068
• 

  

  /19

  $1,850,000 Sold Oct 24, 2024

  • 1,800 Sq Ft
  • $1028/SF
  • 9 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1951

  433 Freeman Rd, Pomfret, VT 05084

  This stunning 604 acre parcel has been in the same family (the Freeman family) - and is offered for sale for the first time - in 75 years. The property includes miles of trails, woodlands, streams, stone walls, and three ponds - including one that is approx 3.5 acres, nearly a "lake". Much of the land is in a Current Land Use conservation program, but is not in permanent conservation. One

  John Snyder Snyder Donegan Real Estate Group

  433 Freeman Rd, Pomfret, VT 05084
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  /38

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  2000 High Pastures Rd, Pomfret, VT 05067

  2000 High Pastures Rd, Pomfret, VT 05067
• 

  

  /39

  $542,000 Sold Oct 01, 2024

  • 1,995 Sq Ft
  • $272/SF
  • 6 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1840

  346 Hewitt Hill Rd, Pomfret, VT 05053

  The "Obed Whipple house" is a charming colonial on a quiet gravel road that takes you back in history to the rural beauty of old-time, quintessential Vermont. The owners through the years have made timely renovations without losing the charm of this antique home. The room flow lends itself to all possibilities. One enters through a sunny, enclosed porch into a mudroom with an antique woodstove

  Bobbi Dagger Bassette Real Estate Group

  346 Hewitt Hill Rd, Pomfret, VT 05053
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  /26

  Est $658,431 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,993 Sq Ft

  204 Hewitt Hill Rd, North Pomfret, VT 05053

  204 Hewitt Hill Rd, North Pomfret, VT 05053
• 

  

  /40

  $580,000 Sold Sep 24, 2024

  • 2,035 Sq Ft
  • $285/SF
  • 98 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1976

  898 Clay Rd, White River Junction, VT 05001

  Perched on a southeasterly-facing knoll with expansive mountain views is this unique home that is ideally situated to take advantage of natural sunlight throughout the day. Sited where the original 1700s home once stood, this more modern home offers spacious rooms and a design that is artistic and unique but has classic and historic elements sprinkled throughout. You'll enjoy the warm morning

  Rachel Arsenault Williamson Group Sothebys Intl. Realty

  898 Clay Rd, White River Junction, VT 05001
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  /25

  Est $280,653 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,120 Sq Ft

  172 Birch Tree Cir, Wood Stock, VT 05091

  172 Birch Tree Cir, Wood Stock, VT 05091
• 

  

  /25

  $730,000 Sold Aug 30, 2024

  • 2,466 Sq Ft
  • $296/SF
  • 76 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  717 Allen Hill Rd, Pomfret, VT 05053

  Beautiful setting and piece of land with extensive gardens, a lovely coursing brook and pastoral views located on a quiet road 1/2 mile from pavement (Howe Hill) and convenient to both Woodstock and Hanover/Norwich/Leb, which are about 20 mins in either direction. The house was built by the sellers and they loved it and lived in it for 50 years. It has an open floorplan with big stone-faced

  John Snyder Snyder Donegan Real Estate Group

  717 Allen Hill Rd, Pomfret, VT 05053
• 

  

  /35

  Not Listed For Sale

  tbd Pomfret Rd, Pomfret, VT 05053

  tbd Pomfret Rd, Pomfret, VT 05053
• 

  

  /27

  $475,000 Sold Sep 27, 2024

  • 1,212 Sq Ft
  • $392/SF
  • 0 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1947

  420 Stage Rd, South Pomfret, VT 05067

  Mary Mayhew Snyder Donegan Real Estate Group

  420 Stage Rd, South Pomfret, VT 05067
• 

  

  /24

  Est $987,297 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,350 Sq Ft

  8126 Pomfret Rd, Pomfret, VT 05053

  8126 Pomfret Rd, Pomfret, VT 05053
• 

  

  /33

  Est $634,261 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,806 Sq Ft

  5994 Broad Brook Rd, Pomfret, VT 05068

  5994 Broad Brook Rd, Pomfret, VT 05068
• 

  

  /6

  Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,302 Sq Ft

  1157 Blackmer Rd, Pomfret, VT 05067

  1157 Blackmer Rd, Pomfret, VT 05067
• 

  

  /38

  Est $498,540 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,638 Sq Ft

  3660 Royalton Turnpike Rd, Pomfret, VT 05068

  3660 Royalton Turnpike Rd, Pomfret, VT 05068
• 

  

  /4

  Not Listed For Sale

  0 Pomfret Rd Unit 4908761, Pomfret, VT 05053

  0 Pomfret Rd Unit 4908761, Pomfret, VT 05053
• 

  

  /40

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,729 Sq Ft

  1350 Vermont 12, Pomfret, VT 05053

  1350 Vermont 12, Pomfret, VT 05053
• 

  

  /20

  Not Listed For Sale

  0 Leonard Rd, Pomfret, VT 05068

  0 Leonard Rd, Pomfret, VT 05068
• 

  

  /9

  Est $807,927 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,695 Sq Ft

  408 Hidden Ridge Rd, Pomfret, VT 05068

  408 Hidden Ridge Rd, Pomfret, VT 05068

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