Woodstock, VT Homes

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  /60

  $1,695,000

  • 4 Beds
  • 3.5 Baths
  • 4,800 Sq Ft

  2706 E Woodstock Rd, Woodstock, VT 05091

  Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, upgraded systems, and fully furnished. Also included, is an additional 2,500+/- sq/ft (total) of an AirBNB rental/In-Law apartment, along with an active US Postal Service rental space, and generous storefront space in the former

  

  John Bassette

  Bassette Real Estate Group

  2706 E Woodstock Rd, Woodstock, VT 05091
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  /13

  $1,595 Per Month

  • 1 Bed
  • 1 Bath
  • 1,400 Sq Ft
  • Apartment for Rent

  36 Happy Valley Rd, Woodstock, VT 05091

  Lovely studio efficiency kitchen area, located in a Historic Hamlet of Woodstock Vermont.7 miles to I89 and the Upper Valley. The house is beautiful and studio is on the second floor. Spacious, furnished, charming. Couch, full size bed, table and 2 chairs. Heat, electric, water, sewer, high speed internet , off street parking all included in rent.Quiet, easy living. Security background

  Gail Childs Covered Bridge RE

  36 Happy Valley Rd, Woodstock, VT 05091
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  /53

  $798,000

  Sold Oct 31, 2025

  392 Gully Rd, Woodstock, VT 05091

  • 2 Beds
  • 2 Baths
  • 1,308 Sq Ft
  • Built 2019

  Last Sold Summary

  • $610/SF
  • 28 Days On Market

  Current Estimated Value $781,992

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  392 Gully Rd, Woodstock, VT 05091
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  /55

  Est $1,174,227

  Not Listed For Sale

  2 Maple St, Woodstock, VT 05091

  • 4 Beds
  • 3.5 Baths
  • 2,710 Sq Ft
  • Built 2020

  2 Maple St, Woodstock, VT 05091

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty
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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

  41 Pleasant St, Woodstock, VT 05091
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  /27

  $3,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,237 Sq Ft
  • House for Rent

  51 Terrace St, Woodstock, VT 05091

  Welcome to the Furnished 2 Bedroom in Woodstock, a charming home nestled in the heart of Woodstock, VT. This home boasts two spacious bedrooms and two full bathrooms, perfect for those who value comfort and convenience. The updated kitchen and baths add a modern touch to the home, while the hardwood flooring throughout gives it a warm, inviting feel. The home is equipped with air conditioning,

  51 Terrace St, 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 $685,878

  Last Listing Agent Nan Carroll Coldwell Banker LIFESTYLES - Hanover

  4 Stanton St, Woodstock, VT 05091
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  /52

  Est $562,548

  Not Listed For Sale

  1613 W Woodstock Rd, Woodstock, VT 05091

  • 3 Beds
  • 1.5 Baths
  • 2,240 Sq Ft
  • Built 1944

  1613 W Woodstock Rd, Woodstock, VT 05091

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Holly Hall Hall Collins Real Estate Group
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  /28

  $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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  /8

  $1,575 Per Month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  1711 W Woodstock Rd Unit 5, Woodstock, VT 05091

  Enjoy the comfort and convenience of this charming second-floor, one-bedroom apartment located in a well-maintained multi-family home in desirable West Woodstock. Filled with natural light, the apartment features high ceilings, a spacious bedroom with two large closets and an additional cable hookup, a full bathroom with a tub and shower, and the convenience of an in-unit washer and dryer. The

  Matt DePrizio Covered Bridge RE

  1711 W Woodstock Rd Unit 5, 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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  /26

  Not Listed For Sale

  11A Prospect St, Woodstock, VT 05091

  • 2 Beds
  • 1.5 Baths
  • 930 Sq Ft
  • Built 1860

  11A Prospect St, Woodstock, VT 05091

  Last Sold Summary

  • 98 Days On Market

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty
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  /33

  $1,895,000

  • 2 Beds
  • 2.5 Baths
  • 2,944 Sq Ft

  2394 Fletcher Hill Rd, Woodstock, VT 05091

  Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is

  John Snyder Snyder Donegan Real Estate Group

  2394 Fletcher Hill Rd, Woodstock, VT 05091
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  /25

  $4,500 Per Month

  • 3 Beds
  • 2 Baths
  • 2,142 Sq Ft
  • House for Rent

  1193 Prosper Rd, Woodstock, VT 05091

  3 bedroom, 2 bathroom home in Woodstock, Vermont, featuring an open-concept layout, hardwood floors throughout, and abundant natural light. Set on 4 acres that offer privacy and a connection to nature, the property includes a chicken coop and raised garden beds for easy homesteading. Trails are nearby and skiing is close by, while Central Street is a short distance away for dining and shopping.

  1193 Prosper Rd, 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 $1,649,473

  Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  441 Spruce Way, Woodstock, VT 05091
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  /40

  Est $2,614,393

  Not Listed For Sale

  739 Westerdale Rd, Woodstock, VT 05091

  • 4 Beds
  • 4.5 Baths
  • 5,017 Sq Ft
  • Built 2003

  739 Westerdale Rd, Woodstock, VT 05091

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent John Snyder Snyder Donegan Real Estate Group
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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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  /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 $610,046

  Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  187 Dana Rd, Woodstock, VT 05091
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  /44

  Est $1,776,093

  Not Listed For Sale

  2090 Randall Rd, Woodstock, VT 05091

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

  2090 Randall Rd, Woodstock, VT 05091

  Last Sold Summary

  • 177 Days On Market

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty
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  /58

  $2,650,000

  $450K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,843 Sq Ft

  66 Hollow Farm Rd, Woodstock, VT 05071

  CURTIS HOLLOW FARM, Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows

  David Donegan Snyder Donegan Real Estate Group

  66 Hollow Farm Rd, Woodstock, VT 05071
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  /60

  $1,520,000

  Sold Sep 30, 2025

  6196 Stage Rd, Woodstock, VT 05091

  • 4 Beds
  • 4 Baths
  • 2,408 Sq Ft
  • Built 2015

  Last Sold Summary

  • 2% Above List Price
  • $631/SF
  • 4 Days On Market

  Last Listing Agent Eric Johnston Four Seasons Sotheby's Int'l Realty

  6196 Stage Rd, Woodstock, VT 05091
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  /34

  Est $712,350

  Not Listed For Sale

  294 Barberry Hill Rd, Woodstock, VT 05091

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft
  • Built 1968

  294 Barberry Hill Rd, Woodstock, VT 05091

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Bonnie Bergeron Snyder Donegan 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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  /15

  $120,000

  Sold Apr 17, 2026

  00 Carlton Hill Rd, Woodstock, VT 05091

  • Land
  • 3.54 Acres
  • $33,898 per Acre

  Last Sold Summary

  • 19% Below List Price
  • 0 Days On Market

  Last Listing Agent Sandy Reavill

  00 Carlton Hill Rd, Woodstock, VT 05091
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  /48

  Est $1,102,759

  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

  • 15 Days On Market

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty
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  /48

  $1,695,000

  • 4 Beds
  • 2.5 Baths
  • 3,542 Sq Ft

  353 Cabot Rd, Woodstock, VT 05091

  "BLISS HOUSE" Privately nestled on a picturesque hillside just minutes from the Woodstock Village Green, this beautifully renovated residence offers exceptional privacy, sweeping long-range mountain views, open meadows, mature gardens, a swimming pool, hot tub, and the perfect blend of Vermont charm and modern comfort. A thoughtful renovation transformed the kitchen and dining areas into a

  John Snyder Snyder Donegan Real Estate Group

  353 Cabot Rd, Woodstock, VT 05091
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  /38

  $870,000

  Sold Jun 25, 2026

  51 River St, Woodstock, VT 05091

  • 4 Beds
  • 1.5 Baths
  • 1,580 Sq Ft
  • Built 1853

  Last Sold Summary

  • 3% Below List Price
  • $551/SF
  • 10 Days On Market

  Current Estimated Value $831,773

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  51 River St, Woodstock, VT 05091
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  /35

  Est $610,610

  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

  • 38 Days On Market

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

  • 495 Days On Market

  Last Listing Agent Story Jenks LandVest, Inc/Woodstock
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  /60

  $2,500,000

  • 4 Beds
  • 3.5 Baths
  • 5,127 Sq Ft

  114 Oak Ridge Way, Woodstock, VT 05091

  See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen—complete with a Sub-Zero

  Tami Sullivan Snyder Donegan Real Estate Group

  114 Oak Ridge 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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  /8

  Not Listed For Sale

  1028 Fairbanks Turn, Woodstock, VT 05091

  1028 Fairbanks Turn, Woodstock, VT 05091

  Last Sold Summary

  • 162 Days On Market

  Last Listing Agent Heather Ashline BHHS Verani Upper Valley
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  /58

  $1,395,000

  $100K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,648 Sq Ft

  1522 Barnard Rd, Woodstock, VT 05091

  Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add

  Keri Cole Williamson Group Sothebys Intl. Realty

  1522 Barnard Rd, Woodstock, VT 05091
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  /57

  $775,000

  Sold Jul 01, 2026

  616 Rose Hill Rd, Woodstock, VT 05091

  • 3 Beds
  • 2 Baths
  • 2,760 Sq Ft
  • Built 1988

  Last Sold Summary

  • 21% Below List Price
  • $281/SF
  • 202 Days On Market

  Current Estimated Value $892,933

  Last Listing Agent Carol Wood Williamson Group Sothebys Intl. Realty

  616 Rose Hill Rd, Woodstock, VT 05091
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  /32

  Est $750,931

  Not Listed For Sale

  13 Golf Ave, Woodstock, VT 05091

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

  13 Golf Ave, Woodstock, VT 05091

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty
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  /4

  $169,000

  • Land
  • 15.4 Acres
  • $10,974 per Acre

  0 Iver Johnson Way Unit 5095630, Woodstock, VT 05091

  Instant equity in Woodstock! Bring your vision to life on this exceptional parcel of raw land, nestled in one of Vermont’s most coveted and quintessential communities. Offered below its current town-assessed value and backed by a recent independent appraisal valuation, this property delivers significant instant equity from day one. Whether you envision a private, tucked-away country estate or a

  Chelsea Bevis KW Vermont Woodstock

  0 Iver Johnson Way Unit 5095630, 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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  /27

  Est $971,322

  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

  • 47 Days On Market

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

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