South Woodstock, VT Homes

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  /54

  $2,599,000

  • 9 Beds
  • 11 Baths
  • 5,993 Sq Ft

  41 Pleasant St, Woodstock, VT 05091

  This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with

  

  Jennifer Falvey

  KW Vermont Woodstock

  (802) 347-9544

  41 Pleasant St, Woodstock, VT 05091
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  /25

  $3,200 per month

  • 2 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Apartment for Rent

  21 Central St, Woodstock, VT 05091

  Offered for lease is a luxury apartment in the very heart of Woodstock Village! The elevated location, above the hub of central village shopping, presents captivating views of village activity, as well as distant hills. The owners started with a blank slate, in a previously vacant space and have provided all of the benefits of wall to wall new construction. State of the art mechanical systems

  John Wetmore Wetmore Real Estate

  21 Central St, Woodstock, VT 05091
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  /2

  $4,350,000 Sold Dec 12, 2025

  700 Barton Rd, West Windsor, VT 05089

  • 3 Beds
  • 3.5 Baths
  • 3,884 Sq Ft
  • Built 2006

  Last Sold Summary

  • $1,120/SF
  • 0 Days On Market

  Last Listing Agent Story Jenks LandVest, Inc/Woodstock

  700 Barton Rd, West Windsor, VT 05089
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  /39

  Est $736,850 Not Listed For Sale

  6 Highland Ave, Woodstock, VT 05091

  • 1 Bed
  • 1 Bath
  • 1,052 Sq Ft
  • Built 1930

  6 Highland Ave, Woodstock, VT 05091

  Last Sold Summary

  • 80% Above List Price
  • $390/SF
  • 97 Days On Market

  Last Sold Price $410,000

  Last Listing Agent John Wetmore Wetmore Real Estate
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  $995,000

  • 3 Beds
  • 3.5 Baths
  • 2,584 Sq Ft

  26 Mount Peg Rd Unit C, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit C, Woodstock, VT 05091
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  /36

  $655,000 Sold Nov 24, 2025

  4 Stanton St, Woodstock, VT 05091

  • 4 Beds
  • 2.5 Baths
  • 2,124 Sq Ft
  • Built 1901

  Last Sold Summary

  • 18% Above List Price
  • $308/SF
  • 7 Days On Market

  Current Estimated Value $609,874

  Last Listing Agent Nan Carroll Coldwell Banker LIFESTYLES - Hanover

  4 Stanton St, Woodstock, VT 05091
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  /50

  Est $1,312,882 Not Listed For Sale

  1075 Westerdale Rd, Woodstock, VT 05091

  • 3 Beds
  • 3.5 Baths
  • 2,584 Sq Ft
  • Built 1985

  1075 Westerdale Rd, Woodstock, VT 05091

  Last Sold Summary

  • 3% Above List Price
  • $493/SF
  • 72 Days On Market

  Last Sold Price $1,275,000

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty
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  /31

  $1,195,000

  • 3 Beds
  • 3.5 Baths
  • 2,385 Sq Ft

  26 Mount Peg Rd Unit D, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit D, Woodstock, VT 05091
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  /59

  $1,625,000 Sold Oct 24, 2025

  7 North St, Woodstock, VT 05091

  • 2 Beds
  • 3 Baths
  • 2,106 Sq Ft
  • Built 1880

  Last Sold Summary

  • 12% Below List Price
  • $772/SF
  • 111 Days On Market

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  7 North St, Woodstock, VT 05091
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  /35

  Not Listed For Sale

  378 Fletcher Hill Rd, South Woodstock, VT 05071

  • 4 Beds
  • 1 Bath
  • 1,424 Sq Ft
  • Built 1971

  378 Fletcher Hill Rd, South Woodstock, VT 05071

  Last Sold Summary

  • $334/SF
  • 144 Days On Market

  Last Sold Price $475,000

  Last Listing Agent John Wetmore Wetmore Real Estate
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  /41

  $1,495,000

  • 4 Beds
  • 1.5 Baths

  7 Slayton Terrace, Woodstock, VT 05091

  A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully

  Keri Cole Williamson Group Sotheby's International Realty

  7 Slayton Terrace, Woodstock, VT 05091
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  /40

  $1,625,000 Sold Sep 29, 2025

  441 Spruce Way, Woodstock, VT 05091

  • 4 Beds
  • 3 Baths
  • 2,619 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $620/SF
  • 6 Days On Market

  Current Estimated Value $1,591,365

  Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  441 Spruce Way, Woodstock, VT 05091
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  /24

  Not Listed For Sale

  29 Heritage Condos Unit 29D, Woodstock, VT 05091

  • 1 Bed
  • 1 Bath
  • 856 Sq Ft
  • Built 1984

  29 Heritage Condos Unit 29D, Woodstock, VT 05091

  Last Sold Summary

  • $269/SF
  • 3 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Franchesca Collins Hall Collins Real Estate Group
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  /32

  $1,195,000

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

  26 Mount Peg Rd Unit A, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit A, Woodstock, VT 05091
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  /32

  $700,000 Sold May 30, 2025

  13 Golf Ave, Woodstock, VT 05091

  • 2 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Built 1880

  Last Sold Summary

  • $461/SF
  • 0 Days On Market

  Current Estimated Value $673,918

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  13 Golf Ave, Woodstock, VT 05091
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  /48

  Est $1,131,632 Not Listed For Sale

  5274 W Woodstock Rd, Woodstock, VT 05091

  • 2 Beds
  • 2 Baths
  • 2,058 Sq Ft
  • Built 1972

  5274 W Woodstock Rd, Woodstock, VT 05091

  Last Sold Summary

  • 5% Below List Price
  • $581/SF
  • 15 Days On Market

  Last Sold Price $1,195,000

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty
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  /31

  $995,000

  • 3 Beds
  • 3.5 Baths
  • 2,584 Sq Ft

  26 Mount Peg Rd Unit B, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit B, Woodstock, VT 05091
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  /11

  $213,000 Sold Jun 06, 2025

  644 Vermont 12, Hartland, VT 05048

  • Land
  • 33.2 Acres
  • $6,416 per Acre

  Last Sold Summary

  • 23% Below List Price
  • 508 Days On Market

  Current Estimated Value $208,497

  Last Listing Agent Chris Crowe Quechee Lakes Real Estate Center

  644 Vermont 12, Hartland, VT 05048
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  Est $1,109,340 Not Listed For Sale

  433 Cowdrey Path, Woodstock, VT 05091

  • 4 Beds
  • 4 Baths
  • 3,507 Sq Ft
  • Built 1986

  433 Cowdrey Path, Woodstock, VT 05091

  Last Sold Summary

  • 14% Above List Price
  • $278/SF
  • 207 Days On Market

  Last Sold Price $975,000

  Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group
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  /60

  $1,300,000 Under Contract

  • 4 Beds
  • 5 Baths
  • 3,195 Sq Ft

  125 Shurtleff Ln, Woodstock, VT 05091

  Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for everyday living and entertaining, the main level features an open, light-filled layout, a well-appointed kitchen, and seamless access to a sunny three-season room overlooking the landscaped grounds. The sought-after first-floor

  Keri Cole Williamson Group Sothebys Intl. Realty

  125 Shurtleff Ln, Woodstock, VT 05091
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  /22

  $618,500 Sold Oct 03, 2025

  187 Dana Rd, Woodstock, VT 05091

  • 3 Beds
  • 1.5 Baths
  • 1,468 Sq Ft
  • Built 1955

  Last Sold Summary

  • 8% Below List Price
  • $421/SF
  • 108 Days On Market

  Current Estimated Value $603,522

  Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  187 Dana Rd, Woodstock, VT 05091
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  /35

  Est $595,591 Not Listed For Sale

  93 Blackbriar Rd, Woodstock, VT 05091

  • 2 Beds
  • 1 Bath
  • 1,146 Sq Ft
  • Built 1950

  93 Blackbriar Rd, Woodstock, VT 05091

  Last Sold Summary

  • $519/SF
  • 38 Days On Market

  Last Sold Price $595,000

  Last Listing Agent David Donegan Snyder Donegan Real Estate Group
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  /37

  $985,000

  • 4 Beds
  • 3 Baths
  • 2,785 Sq Ft

  1782 Randall Rd, Woodstock, VT 05091

  This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

  Wade Treadway Wade I Treadway Real Estate

  1782 Randall Rd, Woodstock, VT 05091
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  /34

  $2,210,000 Sold Sep 24, 2025

  15 Hathorn Hill Street Extension, Woodstock, VT 05091

  • 4 Beds
  • 3.5 Baths
  • 3,564 Sq Ft
  • Built 2009

  Last Sold Summary

  • 1% Above List Price
  • $620/SF
  • 68 Days On Market

  Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  15 Hathorn Hill Street Extension, Woodstock, VT 05091
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  /34

  Not Listed For Sale

  5 Mountain Ave Unit 4, Woodstock, VT 05091

  • 2 Beds
  • 2.5 Baths
  • 1,590 Sq Ft
  • Built 1880

  5 Mountain Ave Unit 4, Woodstock, VT 05091

  Last Sold Summary

  • $550/SF
  • 12 Days On Market

  Last Sold Price $875,000

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty
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  /57

  $1,195,000

  • 4 Beds
  • 2.5 Baths
  • 2,668 Sq Ft

  513 Deer Brook Way, Woodstock, VT 05091

  Set on a sun-bathed hillside between Woodstock Village and the renowned slopes of Killington and Pico, this custom-built Colonial captures what buyers seek most in Vermont: privacy, craftsmanship, and striking mountain views that feel close enough to touch. Thoughtfully designed by the respected Vermont Vernacular Builders, the home reflects classic regional architecture with refined proportions,

  Keri Cole Williamson Group Sothebys Intl. Realty

  513 Deer Brook Way, Woodstock, VT 05091
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  /60

  $1,650,000 Sold Nov 08, 2025

  2334 South Rd, Woodstock, VT 05091

  • 3 Beds
  • 2.5 Baths
  • 5,422 Sq Ft
  • Built 1972

  Last Sold Summary

  • 25% Below List Price
  • $304/SF
  • 94 Days On Market

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  2334 South Rd, Woodstock, VT 05091
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  Not Listed For Sale

  00 Weed Rd, Hartland, VT 05049

  00 Weed Rd, Hartland, VT 05049

  Last Sold Summary

  • 15 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Dia Jenks LandVest, Inc/Woodstock
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  /57

  $817,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,760 Sq Ft

  616 Rose Hill Rd, Woodstock, VT 05091

  This is a rare opportunity to own 10.1 acres of land in a coveted area of Woodstock that includes a 1988 Frizzell Builders house and a detached oversized garage with a second floor for storage . The property was part of the King Farm which is now in Vt. Land Trust as conserved land , until it was split off in the late 1980's when the Colby family came into ownership and built the existing house

  Carol Wood Williamson Group Sothebys Intl. Realty

  616 Rose Hill Rd, Woodstock, VT 05091
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  /39

  $613,000 Sold Sep 10, 2025

  5851 South Rd, Woodstock, VT 05071

  • 3 Beds
  • 2.5 Baths
  • 1,958 Sq Ft
  • Built 1920

  Last Sold Summary

  • 19% Below List Price
  • $313/SF
  • 302 Days On Market

  Last Listing Agent Carol Wood Williamson Group Sothebys Intl. Realty

  5851 South Rd, Woodstock, VT 05071
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  /40

  Not Listed For Sale

  318 Ebbin Lockwood Way, Woodstock, VT 05071

  • 3 Beds
  • 3.5 Baths
  • 6,047 Sq Ft
  • Built 1970

  318 Ebbin Lockwood Way, Woodstock, VT 05071

  Last Sold Summary

  • $455/SF
  • 495 Days On Market

  Last Sold Price $2,750,000

  Last Listing Agent Story Jenks LandVest, Inc/Woodstock
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  /11

  $190,000

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  99 Safford Commons Way, Woodstock, VT 05091

  These 1200 sq. ft., 2-bedroom, 1.5-bathroom condos are being sold for less than half of their fair market value! Available for immediate move-in, each condo has an open-concept kitchen, dining room, and living room, which are on the airy and light-filled second floor. There is a small deck off the living room. The two cozy bedrooms are on the first floor. Electricity bills will be offset by solar

  Jane Darrach Martha E. Diebold/Hanover

  99 Safford Commons Way, Woodstock, VT 05091
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  /48

  $705,000 Sold Nov 26, 2025

  25 Linden Hill St, Woodstock, VT 05091

  • 3 Beds
  • 2 Baths
  • 1,694 Sq Ft
  • Built 1910

  Last Sold Summary

  • 11% Below List Price
  • $416/SF
  • 217 Days On Market

  Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

  25 Linden Hill St, Woodstock, VT 05091
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  /40

  Est $594,891 Not Listed For Sale

  21 Sportsmen Cove, Hartland, VT 05048

  • 3 Beds
  • 2 Baths
  • 1,980 Sq Ft
  • Built 2006

  21 Sportsmen Cove, Hartland, VT 05048

  Last Sold Summary

  • 10% Above List Price
  • $274/SF
  • 19 Days On Market

  Last Sold Price $542,500

  Last Listing Agent John Bassette Bassette Real Estate Group
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  /40

  $2,950,000

  • 6 Beds
  • 6 Baths
  • 5,433 Sq Ft

  61 Academy Cir, Woodstock, VT 05071

  Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The

  Carol Wood Williamson Group Sothebys Intl. Realty

  61 Academy Cir, Woodstock, VT 05071
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  /30

  $405,000 Sold Feb 17, 2026

  37 Atwood Ave, Woodstock, VT 05091

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1960

  Last Sold Summary

  • 16% Below List Price
  • $527/SF
  • 152 Days On Market

  Current Estimated Value $410,445

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  37 Atwood Ave, Woodstock, VT 05091
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  Not Listed For Sale

  7429 Us Route 4, Bridgewater, VT 05034

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1800

  7429 Us Route 4, Bridgewater, VT 05034

  Last Sold Summary

  • $253/SF
  • 25 Days On Market

  Last Sold Price $430,000

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty
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  /26

  $465,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  57 Townhouse Way Unit 9, Woodstock, VT 05091

  This beautiful Woodstock West Townhouse offers effortless, low-maintenance living in one of Vermont’s most charming four-season destinations. The main level welcomes you with a cozy living area centered around a fireplace, creating the perfect space to unwind. A sun-filled kitchen and dining area flow seamlessly onto a private deck—ideal for relaxing or entertaining. Upstairs, two generously

  Mary Mayhew Snyder Donegan Real Estate Group

  57 Townhouse Way Unit 9, Woodstock, VT 05091
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  $1,700,000 Sold Aug 15, 2025

  2090 Randall Rd, Woodstock, VT 05091

  • 3 Beds
  • 2.5 Baths
  • 2,423 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $702/SF
  • 177 Days On Market

  Current Estimated Value $1,699,354

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  2090 Randall Rd, Woodstock, VT 05091
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  /27

  Est $921,981 Not Listed For Sale

  7 Golf Ave, Woodstock, VT 05091

  • 5 Beds
  • 3 Baths
  • 3,579 Sq Ft
  • Built 1832

  7 Golf Ave, Woodstock, VT 05091

  Last Sold Summary

  • 68% Above List Price
  • $154/SF
  • 47 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

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