2,703

Woodstock, VT Homes

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    • /20

      Est $2,411,790

      Not Listed For Sale

      3086 South Rd, Woodstock, VT 05091

      • 4 Beds
      • 4.5 Baths
      • 3,550 Sq Ft
      • Built 1986
      3086 South Rd, Woodstock, VT 05091

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  • /31

    $244,000

    • 1 Bed
    • 1 Bath
    • 856 Sq Ft

    42-18 Heritage Condo Way Unit 18D, Woodstock, VT 05091

    Easy living in this updated condo that is perfect for a primary or secondary residence. Located in a small condo community that is mostly owner occupied the setting offers a private living space. The deck looks out to well maintained grounds and woodlands. The updated kitchen and bathroom are well appointed. The main level has an open floor plan that includes the kitchen, dining area and living

    Carol Wood Williamson Group Sothebys Intl. Realty

    42-18 Heritage Condo Way Unit 18D, Woodstock, VT 05091
  • /50

    $875,000

    Sold Feb 10, 2026

    100 Pomfret Rd, Woodstock, VT 05091

    • 4 Beds
    • 2.5 Baths
    • 2,044 Sq Ft
    • Built 1930

    Last Sold Summary

    • 7% Below List Price
    • $428/SF
    • 163 Days On Market

    Current Estimated Value $863,823

    Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

    100 Pomfret Rd, Woodstock, VT 05091
    • /40

      Est $832,495

      Not Listed For Sale

      917 Carlton Hill Rd, Woodstock, VT 05091

      • 3 Beds
      • 2.5 Baths
      • 1,844 Sq Ft
      • Built 1975
      917 Carlton Hill Rd, Woodstock, VT 05091

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  • /5

    $850,000

    • Land
    • 1.47 Acres
    • $578,231 per Acre

    97 Valley View Rd, Woodstock, VT 05091

    The justifiably proud owner of this property points out these features: Potential "Barnominium." Conveniently located just 1/4 mile from Woodstock Village town line and just 40 minutes from Killington Ski area. Built for an auto collection. Full bathroom, blown in insulation in ceiling, foam spray insulation in walls (with bug mesh in walls.) 3/4" sheet rock! All electrical is done in 3/4'

    John Wetmore Wetmore Real Estate

    97 Valley View Rd, Woodstock, VT 05091
  • /26

    $205,000

    Sold Nov 21, 2025

    33 Heritage Condos Way Unit 33D, Woodstock, VT 05091

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

    Last Sold Summary

    • 2% Below List Price
    • $239/SF
    • 10 Days On Market

    Last Listing Agent Jennifer Falvey KW Vermont Woodstock

    33 Heritage Condos Way Unit 33D, Woodstock, VT 05091
    • /40

      Not Listed For Sale

      587 Old River Rd, Woodstock, VT 05091

      • 5 Beds
      • 5.5 Baths
      • 6,799 Sq Ft
      • Built 1850
      587 Old River Rd, Woodstock, VT 05091

      Last Sold Summary

      • 473 Days On Market

      Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  • /52

    $5,950,000

    New Construction $1M PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 5,087 Sq Ft

    412 Skyland Ln, Woodstock, VT 05091

    Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and

    Story Jenks LandVest, Inc/Woodstock

    412 Skyland Ln, Woodstock, VT 05091
  • /55

    $1,800,000

    Sold Feb 27, 2026

    74 Barber Hill Rd, Woodstock, VT 05091

    • 4 Beds
    • 3.5 Baths
    • 3,288 Sq Ft
    • Built 1938

    Last Sold Summary

    • 3% Above List Price
    • $547/SF
    • 7 Days On Market

    Current Estimated Value $1,838,000

    Last Listing Agent John Wetmore Wetmore Real Estate

    74 Barber Hill Rd, Woodstock, VT 05091
    • /38

      Est $833,519

      Not Listed For Sale

      506 Westerdale Rd, Woodstock, VT 05091

      • 3 Beds
      • 2 Baths
      • 1,492 Sq Ft
      • Built 1987
      506 Westerdale Rd, Woodstock, VT 05091

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  • /37

    $865,000

    $320K PRICE DROP
    • 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
  • /39

    $740,000

    Sold Oct 21, 2025

    1082 Greengate Rd, Woodstock, VT 05091

    • 3 Beds
    • 2.5 Baths
    • 1,878 Sq Ft
    • Built 1992

    Last Sold Summary

    • 5% Below List Price
    • $394/SF
    • 32 Days On Market

    Current Estimated Value $766,455

    Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

    1082 Greengate Rd, Woodstock, VT 05091
    • /6

      Not Listed For Sale

      7 Hathorn Hill Unit 7, Woodstock, VT 05091

      • 3 Beds
      • 3 Baths
      • 1,310 Sq Ft
      • Built 1984
      7 Hathorn Hill Unit 7, Woodstock, VT 05091

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  • /47

    $395,000

    $44K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,617 Sq Ft

    5798 W Woodstock Rd, Woodstock, VT 05091

    Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors

    Carol Wood Williamson Group Sothebys Intl. Realty

    5798 W Woodstock Rd, Woodstock, VT 05091
  • /40

    $660,000

    Sold Apr 30, 2026

    3914 South Rd, Woodstock, VT 05091

    • 4 Beds
    • 3 Baths
    • 3,584 Sq Ft
    • Built 1984

    Last Sold Summary

    • 9% Below List Price
    • $184/SF
    • 142 Days On Market

    Current Estimated Value $713,570

    Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

    3914 South Rd, Woodstock, VT 05091
    • /36

      Est $1,914,580

      Not Listed For Sale

      484 Carlton Hill Rd, Woodstock, VT 05091

      • 4 Beds
      • 5 Baths
      • 4,100 Sq Ft
      • Built 2008
      484 Carlton Hill Rd, Woodstock, VT 05091

      Last Sold Summary

      • 61 Days On Market

      Last Listing Agent Jennifer Kirkman KW Vermont Woodstock

  • /22

    $350,000

    $49K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 536 Sq Ft

    1190 Long Hill Rd, Woodstock, VT 05071

    Tucked away on 11.58 private acres in the heart of South Woodstock, this peaceful Vermont retreat offers simplicity, seclusion, and endless potential. Located along scenic Long Hill Road, surrounded by rolling countryside, woodland trails, and some of the area’s most distinguished estates. The property features a cozy 1-bedroom, 1-bath home with an open, efficient layout designed for quiet

    Tara Reeves Vermont Real Estate Company

    1190 Long Hill Rd, Woodstock, VT 05071
  • /54

    $1,300,000

    Sold Nov 05, 2025

    687 S Perry Rd, Woodstock, VT 05091

    • 5 Beds
    • 4.5 Baths
    • 4,617 Sq Ft
    • Built 1970

    Last Sold Summary

    • 26% Below List Price
    • $282/SF
    • 107 Days On Market

    Current Estimated Value $1,369,999

    Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

    687 S Perry Rd, Woodstock, VT 05091
    • /40

      Est $739,389

      Not Listed For Sale

      588 Kendall Rd, Woodstock, VT 05091

      • 5 Beds
      • 2 Baths
      • 2,904 Sq Ft
      • Built 1870
      588 Kendall Rd, Woodstock, VT 05091

      Last Sold Summary

      • 92 Days On Market

      Last Listing Agent John Wetmore Wetmore Real Estate

  • /26

    $450,000

    $45K PRICE DROP
    • 2 Beds
    • 3 Baths
    • 2,091 Sq Ft

    85 Townhouse Way Unit 14, Woodstock, VT 05091

    Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! This unit is in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    85 Townhouse Way Unit 14, Woodstock, VT 05091
  • /42

    $400,000

    Sold Apr 07, 2026

    1079 Fletcher Hill Rd, Woodstock, VT 05071

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1957

    Last Sold Summary

    • 6% Below List Price
    • $278/SF
    • 147 Days On Market

    Last Listing Agent Terry Davis Williamson Group Sothebys Intl. Realty

    1079 Fletcher Hill Rd, Woodstock, VT 05071
    • /24

      Est $541,968

      Not Listed For Sale

      708 E Woodstock Rd, Woodstock, VT 05091

      • 3 Beds
      • 1 Bath
      • 1,034 Sq Ft
      • Built 1946
      708 E Woodstock Rd, Woodstock, VT 05091

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Karen DeMas Four Seasons Sotheby's Int'l Realty

  • /28

    $239,000

    Sold Sep 11, 2025

    42 Heritage Condo Way Unit 16, Woodstock, VT 05091

    • 1 Bed
    • 1 Bath
    • 816 Sq Ft
    • Built 1987

    Last Sold Summary

    • 4% Below List Price
    • $293/SF
    • 15 Days On Market

    Last Listing Agent Franchesca Collins Hall Collins Real Estate Group

    42 Heritage Condo Way Unit 16, Woodstock, VT 05091
    • /17

      Not Listed For Sale

      132 Riverbend Way, Woodstock, VT 05091

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 2011
      132 Riverbend Way, Woodstock, VT 05091

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Jenna Luce RE/MAX Upper Valley

  • /33

    $565,000

    Sold Dec 30, 2025

    35 Mountain Ave, Woodstock, VT 05091

    • 3 Beds
    • 2.5 Baths
    • 1,555 Sq Ft
    • Built 1856

    Last Sold Summary

    • 16% Below List Price
    • $363/SF
    • 69 Days On Market

    Current Estimated Value $616,095

    Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

    35 Mountain Ave, Woodstock, VT 05091
    • /40

      Est $1,593,912

      Not Listed For Sale

      612 Church Hill Rd, Woodstock, VT 05091

      • 5 Beds
      • 4 Baths
      • 3,042 Sq Ft
      • Built 2009
      612 Church Hill Rd, Woodstock, VT 05091

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  • /44

    $1,900,000

    Sold Sep 05, 2025

    51 Watkins Way Unit 2, Woodstock, VT 05091

    • 3 Beds
    • 2.5 Baths
    • 3,227 Sq Ft
    • Built 2021

    Last Sold Summary

    • $589/SF
    • 0 Days On Market

    Current Estimated Value $1,919,570

    Last Listing Agent John King

    51 Watkins Way Unit 2, Woodstock, VT 05091
    • /40

      Not Listed For Sale

      6963 South Rd, Woodstock, VT 05071

      • 2 Beds
      • 1.5 Baths
      • 1,840 Sq Ft
      • Built 1970
      6963 South Rd, Woodstock, VT 05071

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  • /27

    $612,500

    Sold Mar 26, 2026

    0 Mecawee Rd, Woodstock, VT 05091

    • Land
    • 77.7 Acres
    • $7,883 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 217 Days On Market

    Last Listing Agent Dan Noble Snyder Donegan Real Estate Group

    0 Mecawee Rd, Woodstock, VT 05091
    • /49

      Not Listed For Sale

      19 Linden Hill St, Woodstock, VT 05091

      • 3 Beds
      • 3.5 Baths
      • 2,034 Sq Ft
      • Built 1992
      19 Linden Hill St, Woodstock, VT 05091

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Holly Hall Hall Collins Real Estate Group

  • /31

    $684,000

    Sold Oct 10, 2025

    13 Slayton Terrace, Woodstock, VT 05091

    • 3 Beds
    • 3 Baths
    • 1,550 Sq Ft
    • Built 1920

    Last Sold Summary

    • 13% Below List Price
    • $441/SF
    • 162 Days On Market

    Current Estimated Value $705,309

    Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

    13 Slayton Terrace, Woodstock, VT 05091
    • /54

      Not Listed For Sale

      22 Orchard Hill Rd, Woodstock, VT 05091

      • 5 Beds
      • 3 Baths
      • 3,012 Sq Ft
      • Built 1971
      22 Orchard Hill Rd, Woodstock, VT 05091

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

  • /32

    $230,000

    Sold Jun 12, 2026

    42 Heritage Condo Way Unit 23 D, Woodstock, VT 05091

    • 1 Bed
    • 1 Bath
    • 856 Sq Ft
    • Built 1987

    Last Sold Summary

    • 4% Below List Price
    • $269/SF
    • 43 Days On Market

    Current Estimated Value $229,999

    Last Listing Agent Carol Wood Williamson Group Sothebys Intl. Realty

    42 Heritage Condo Way Unit 23 D, Woodstock, VT 05091
    • /51

      Est $1,405,344

      Not Listed For Sale

      608 Fletcher Hill Rd, Woodstock, VT 05091

      • 4 Beds
      • 3.5 Baths
      • 4,228 Sq Ft
      • Built 1980
      608 Fletcher Hill Rd, Woodstock, VT 05091

      Last Sold Summary

      • 91 Days On Market

      Last Listing Agent Sandy Reavill

  • /18

    $230,000

    Sold Oct 15, 2025

    56 Heritage Condo Way Unit 9, Woodstock, VT 05091

    • 1 Bed
    • 1 Bath
    • 856 Sq Ft
    • Built 1989

    Last Sold Summary

    • 8% Below List Price
    • $269/SF
    • 40 Days On Market

    Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

    56 Heritage Condo Way Unit 9, Woodstock, VT 05091
    • /50

      Est $1,391,300

      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

      • 72 Days On Market

      Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  • /35

    $1,650,000

    Sold Nov 24, 2025

    10 College Hill Rd, Woodstock, VT 05091

    • 5 Beds
    • 4.5 Baths
    • 4,214 Sq Ft
    • Built 1916

    Last Sold Summary

    • 17% Below List Price
    • $392/SF
    • 79 Days On Market

    Current Estimated Value $1,705,914

    Last Listing Agent John Snyder Snyder Donegan Real Estate Group

    10 College Hill Rd, Woodstock, VT 05091
    • /14

      Not Listed For Sale

      1340 Oxbow Rd, Woodstock, VT 05091

      • 1 Bed
      • 1 Bath
      • 550 Sq Ft
      • Built 2017
      1340 Oxbow Rd, Woodstock, VT 05091

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Ara Cardew BHG Masiello Keene

  • /43

    $5,750,000

    Sold Jan 30, 2026

    37 Maxham Rd, Woodstock, VT 05091

    • 6 Beds
    • 6 Baths
    • 8,264 Sq Ft
    • Built 1790

    Last Sold Summary

    • 6% Below List Price
    • $696/SF
    • 39 Days On Market

    Current Estimated Value $371,002

    Last Listing Agent Story Jenks LandVest, Inc/Woodstock

    37 Maxham Rd, Woodstock, VT 05091
    • /14

      Est $727,980

      Not Listed For Sale

      16 Pomfret Rd, Woodstock, VT 05091

      • 3 Beds
      • 1.5 Baths
      • 1,656 Sq Ft
      • Built 1947
      16 Pomfret Rd, Woodstock, VT 05091

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

Showing Results 121 - 160, Page 4 of 18

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