Woodstock Town, VT Homes

• 

  

  

  /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
• 

  

  

  /26

  $2,000 Per Month

  • 1 Bed
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  44 Butternut Ln Unit 1, Wood Stock, VT 05091

  Enjoy the charm of village living in this beautifully furnished second-floor apartment located in a historic home in the heart of Taftsville, Vermont a hamlet of Woodstock. This bright and inviting apartment offers four spacious rooms, large windows, hard wood floors, a cozy pellet stove (pellets included), and a dedicated full-size office, making it ideal for remote professionals or anyone

  Matt DePrizio Covered Bridge RE

  44 Butternut Ln Unit 1, Wood Stock, VT 05091
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /14

  $1,800 Per Month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  44 Butternut Ln Unit 2, Wood Stock, VT 05091

  Enjoy the charm of village living in this beautifully furnished third-floor, one-bedroom apartment located in a historic home in the heart of Taftsville, Vermont, a hamlet of Woodstock. Bright and inviting, this apartment features large windows, hardwood floors, and an open-concept kitchen and dining area, creating a comfortable and welcoming living space ideal for professionals or anyone seeking

  Matt DePrizio Covered Bridge RE

  44 Butternut Ln Unit 2, Wood Stock, VT 05091
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /48

  $502,000

  $25K PRICE DROP Under Contract

  • 4 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  88 Happy Valley Rd, Woodstock, VT 05091

  Step into a rare offering where timeless New England charm meets contemporary comfort. Originally built in 1846 and thoughtfully reimagined, this exceptional Taftsville, Vermont residence is set along Happy Valley Brook, creating a private sanctuary defined by peace, beauty, and understated elegance. Historic character is beautifully complemented by carefully curated upgrades, including

  Julie Davis KW Vermont Woodstock

  88 Happy Valley Rd, Woodstock, VT 05091
• 

  

  /11

  $190,000

  Sold May 29, 2026

  99 Safford Commons Way, Woodstock, VT 05091

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 2025

  Last Sold Summary

  • $158/SF
  • 115 Days On Market

  Last Listing Agent Jane Darrach Martha E. Diebold/Hanover

  99 Safford Commons Way, Woodstock, VT 05091
• 

  

  /39

  Est $1,332,753

  Not Listed For Sale

  1548 Peterkin Hill Rd, South Woodstock, VT 05071

  • 4 Beds
  • 3.5 Baths
  • 3,934 Sq Ft
  • Built 1999

  1548 Peterkin Hill Rd, South Woodstock, VT 05071

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent John Snyder Snyder Donegan Real Estate Group
• 

  

  /51

  $6,673,000

  Pending

  • 5 Beds
  • 3.5 Baths
  • 4,165 Sq Ft

  2358 Long Hill Rd, Woodstock, VT 05091

  Framed by groves of mature birch trees, a winding drive descends into a private valley surrounded by pastures, apple orchards, a spring-fed pond, and sweeping mountain views, arriving at Birch Tree Farm. Spanning more than 465 acres, this extraordinary Vermont retreat offers an immersive four-season lifestyle -- from pressing fresh cider from the orchard and tapping maple trees for syrup to

  Story Jenks LandVest, Inc/Woodstock

  2358 Long Hill Rd, Woodstock, VT 05091
• 

  

  /11

  $190,000

  Sold May 15, 2026

  111 Safford Commons Way, Woodstock, VT 05091

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 2025

  Last Sold Summary

  • $158/SF
  • 101 Days On Market

  Last Listing Agent Jane Darrach Martha E. Diebold/Hanover

  111 Safford Commons Way, Woodstock, VT 05091
• 

  

  /40

  Est $1,462,487

  Not Listed For Sale

  3090 South Rd, Woodstock, VT 05091

  • 5 Beds
  • 5 Baths
  • 2,375 Sq Ft
  • Built 1884

  3090 South Rd, Woodstock, VT 05091

  Last Sold Summary

  • 343 Days On Market

  Last Listing Agent John Wetmore Wetmore Real Estate
• 

  

  /11

  $779,000

  $200K PRICE INCREASE Pending

  • Land
  • 6.46 Acres
  • $120,588 per Acre

  0 Barnard Rd Unit 20.002, Woodstock, VT 05091

  A truly unique 6 acre parcel of land conveniently located in the heart of Woodstock! Tremendous development potential! Zoning allows both COMMERCIAL and RESIDENTIAL use! The 6 acres visually divide into 2 components with 2 diverse personalities. The 1st component is an extraordinary private building lot in the heart of Woodstock! Access to this 4 acre component initially leads through a pleasant

  John Wetmore Wetmore Real Estate

  0 Barnard Rd Unit 20.002, Woodstock, VT 05091
• 

  

  /43

  $515,000

  Sold May 29, 2026

  1514 South Rd, Woodstock, VT 05091

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 1965

  Last Sold Summary

  • 26% Below List Price
  • $268/SF
  • 226 Days On Market

  Current Estimated Value $544,303

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  1514 South Rd, Woodstock, VT 05091
• 

  

  /28

  Est $908,412

  Not Listed For Sale

  46 Stewart Ln Unit P-304, Ludlow, VT 05149

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft
  • Built 1989

  46 Stewart Ln Unit P-304, Ludlow, VT 05149

  Last Sold Summary

  • 111 Days On Market

  Last Listing Agent Katherine Burns William Raveis Real Estate Vermont Properties
• 

  

  /40

  $2,500,000

  $1M PRICE DROP Under Contract

  • 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
• 

  

  /26

  $456,250

  Sold May 15, 2026

  57 Townhouse Way Unit 9, Woodstock, VT 05091

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Below List Price
  • $264/SF
  • 11 Days On Market

  Current Estimated Value $454,687

  Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  57 Townhouse Way Unit 9, Woodstock, VT 05091
• 

  

  /37

  Est $1,236,498

  Not Listed For Sale

  326 Hall Cir, Woodstock, VT 05091

  • 4 Beds
  • 3 Baths
  • 1,949 Sq Ft
  • Built 1988

  326 Hall Cir, Woodstock, VT 05091

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Carol Wood Williamson Group Sothebys Intl. Realty
• 

  

  /14

  $238,000

  $2K PRICE INCREASE

  • 1 Bed
  • 1 Bath
  • 856 Sq Ft

  42 Heritage Condo Way Unit 24, Woodstock, VT 05091

  Amazing opportunity to own a property that is perfect as a full time home or a vacation get away, in the highly desired Heritage Condo community. Quiet setting in a low density area. This end unit condo has had many updates and is ready for new owners to add their personal touch. A private deck looking out to woodlands and lawn. The bright kitchen is a pleasure to work in . Upstairs the den with

  Ara Cardew BHG Masiello Keene

  42 Heritage Condo Way Unit 24, Woodstock, VT 05091
• 

  

  /24

  $629,500

  Sold Sep 12, 2025

  40 Pomfret Rd, Woodstock, VT 05091

  • 3 Beds
  • 1.5 Baths
  • 1,650 Sq Ft
  • Built 1885

  Last Sold Summary

  • $382/SF
  • 17 Days On Market

  Current Estimated Value $644,109

  Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  40 Pomfret Rd, Woodstock, VT 05091

Showing Results 1 - 40, Page 1 of 18