2,804

Woodstock, VT Homes

Section Image
    • /40

      Not Listed For Sale

      327 Fletcher Schoolhouse Rd, Woodstock, VT 05071

      • 4 Beds
      • 3.5 Baths
      • 4,638 Sq Ft
      • Built 1797
      327 Fletcher Schoolhouse Rd, Woodstock, VT 05071

      Last Sold Summary

      • $907/SF
      • 121 Days On Market
      • Last Sold Price $4,205,000
      • Jan 27, 2025

      Last Listing Agent Story Jenks LandVest, Inc/Woodstock

  • /32

    $239,000 Under Contract

    • 1 Bed
    • 1 Bath
    • 856 Sq Ft

    42 Heritage Condo Way Unit 23 D, 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. The setting is serene in a low density area. This condo has had many updates and is ready for new owners to add their personal touch. The charming living room complete with wood floors , a stone accent wall and double glass doors leading to a private

    Carol Wood Williamson Group Sothebys Intl. Realty

    42 Heritage Condo Way Unit 23 D, Woodstock, VT 05091
  • /60

    $2,097,500 Sold Mar 13, 2026

    1362 Barnard Rd, Woodstock, VT 05091

    • 6 Beds
    • 5 Baths
    • 3,645 Sq Ft
    • Built 1855

    Last Sold Summary

    • 19% Below List Price
    • $575/SF
    • 128 Days On Market

    Current Estimated Value $2,352,667

    Last Listing Agent Chris Lang

    1362 Barnard Rd, Woodstock, VT 05091
    • /30

      Est $1,229,426 Not Listed For Sale

      2409 South Rd, Woodstock, VT 05091

      • 4 Beds
      • 2.5 Baths
      • 2,758 Sq Ft
      • Built 1920
      2409 South Rd, Woodstock, VT 05091

      Last Sold Summary

      • 9% Above List Price
      • $408/SF
      • 28 Days On Market
      • Last Sold Price $1,125,000
      • Oct 17, 2023

      Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  • /32

    $75,000

    • 3 Beds
    • 2 Baths
    • 1,008 Sq Ft

    185 Riverbend Way, Woodstock, VT 05091

    Seller is offering $10,000 towards closing costs and prepaids! Start your Vermont dream with this affordable 3-bedroom, 2-bath mobile home just minutes from downtown Woodstock, VT. Located in a quiet, private community with stunning mountain views and direct river frontage on the Ottauquechee, this home is a rare opportunity to enjoy scenic living at a budget-friendly price. Perfect as a first

    Mendi Michael Engel & Völkers Okemo

    185 Riverbend Way, Woodstock, VT 05091
  • /54

    $1,500,000 Sold Jun 09, 2025

    22 Orchard Hill Rd, Woodstock, VT 05091

    • 5 Beds
    • 3 Baths
    • 3,012 Sq Ft
    • Built 1971

    Last Sold Summary

    • 12% Below List Price
    • $498/SF
    • 68 Days On Market

    Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

    22 Orchard Hill Rd, Woodstock, VT 05091
    • /40

      Not Listed For Sale

      5798 South Rd, Woodstock, VT 05071

      • 5 Beds
      • 6 Baths
      • 3,910 Sq Ft
      • Built 1850
      5798 South Rd, Woodstock, VT 05071

      Last Sold Summary

      • $512/SF
      • 193 Days On Market
      • Last Sold Price $2,000,000
      • Apr 17, 2024

      Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  • /59

    $14,900,000

    • 7 Beds
    • 10 Baths
    • 12,520 Sq Ft

    355 Greene Rd, Woodstock, VT 05071

    Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and

    Chris Lang

    355 Greene Rd, Woodstock, VT 05071
  • /60

    $775,000 Sold May 11, 2026

    3961 Hartland Hill Rd, Woodstock, VT 05091

    • 5 Beds
    • 5 Baths
    • 3,886 Sq Ft
    • Built 1964

    Last Sold Summary

    • 16% Below List Price
    • $199/SF
    • 192 Days On Market

    Current Estimated Value $859,936

    Last Listing Agent Tambrey Vutech KW Vermont Woodstock

    3961 Hartland Hill Rd, Woodstock, VT 05091
    • /40

      Est $1,404,603 Not Listed For Sale

      282 Fletcher Hill Rd, Woodstock, VT 05091

      • 3 Beds
      • 3 Baths
      • 2,329 Sq Ft
      • Built 1986
      282 Fletcher Hill Rd, Woodstock, VT 05091

      Last Sold Summary

      • 6% Below List Price
      • $644/SF
      • 92 Days On Market
      • Last Sold Price $1,500,000
      • Oct 02, 2023

      Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

  • /28

    $3,300,000

    • 3 Beds
    • 4.5 Baths
    • 3,682 Sq Ft

    249 Sawyer Rd, Woodstock, VT 05091

    Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary

    Andrew Bustin LandVest, Inc/Woodstock

    249 Sawyer Rd, Woodstock, VT 05091
  • /55

    $892,500 Sold Apr 28, 2026

    509 Church Hill Rd, Wood Stock, VT 05091

    • 3 Beds
    • 3 Baths
    • 2,150 Sq Ft
    • Built 1940

    Last Sold Summary

    • 19% Below List Price
    • $415/SF
    • 279 Days On Market

    Current Estimated Value $955,927

    Last Listing Agent Carol Wood Williamson Group Sothebys Intl. Realty

    509 Church Hill Rd, Wood Stock, VT 05091
    • /33

      Est $468,937 Not Listed For Sale

      11 Church St Unit 2, Woodstock, VT 05091

      • 2 Beds
      • 1 Bath
      • 1,059 Sq Ft
      • Built 1823
      11 Church St Unit 2, Woodstock, VT 05091

      Last Sold Summary

      • 12% Below List Price
      • $500/SF
      • 8 Days On Market
      • Last Sold Price $530,000
      • Jun 11, 2024

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  • /19

    $345,000

    • Land
    • 6.48 Acres
    • $53,241 per Acre

    0 Oakridge Way, Woodstock, VT 05091

    Your dream home starts right here — with a blank canvas in one of Vermont's most coveted communities. This exceptional buildable lot on Oak Ridge Way presents a rare opportunity to design and construct your ideal residence on a quiet side road in Woodstock. Nestled within a highly sought-after neighborhood, surrounded by million dollar homes, this property offers the kind of setting that inspires

    Nancy Greenwood Watson Realty & Associates

    0 Oakridge Way, Woodstock, VT 05091
  • /40

    $740,000 Sold Aug 18, 2025

    339 Gully Rd, Woodstock, VT 05091

    • 4 Beds
    • 2.5 Baths
    • 2,688 Sq Ft
    • Built 1975

    Last Sold Summary

    • 5% Below List Price
    • $275/SF
    • 67 Days On Market

    Current Estimated Value $790,000

    Last Listing Agent Derek Cosentino Four Seasons Sotheby's Int'l Realty

    339 Gully Rd, Woodstock, VT 05091
    • /38

      Est $1,258,938 Not Listed For Sale

      2876 Hartland Hill Rd, Woodstock, VT 05091

      • 4 Beds
      • 3.5 Baths
      • 3,350 Sq Ft
      • Built 1807
      2876 Hartland Hill Rd, Woodstock, VT 05091

      Last Sold Summary

      • 20% Below List Price
      • $469/SF
      • 112 Days On Market
      • Last Sold Price $1,570,000
      • Feb 15, 2024

      Last Listing Agent Carol Wood Williamson Group Sothebys Intl. Realty

  • /7

    $325,000

    • Land
    • 8 Acres
    • $40,625 per Acre

    1 Carlton Hill Rd, Woodstock, VT 05091

    Sweet Spot - 8 acre building lot located within minutes of the Woodstock Village Green! Driveway is in place and a lovely building site has been cleared and power is at site. Wonderful opportunity to build your Vermont getaway or primary residence. Enjoy access to four season recreation, Marsh-Billings-Rockefeller National Park, theatre, arts, dining, shopping and a short commute to all

    Mary Mayhew Snyder Donegan Real Estate Group

    1 Carlton Hill Rd, Woodstock, VT 05091
  • /17

    $86,500 Sold May 16, 2025

    132 Riverbend Way, Woodstock, VT 05091

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 2011

    Last Sold Summary

    • 13% Below List Price
    • $77/SF
    • 86 Days On Market

    Last Listing Agent Jenna Luce RE/MAX Upper Valley

    132 Riverbend Way, Woodstock, VT 05091
    • /40

      Est $468,639 Not Listed For Sale

      1880 South Rd, Woodstock, VT 05091

      • 3 Beds
      • 2 Baths
      • 1,374 Sq Ft
      • Built 1900
      1880 South Rd, Woodstock, VT 05091

      Last Sold Summary

      • 34% Above List Price
      • $255/SF
      • 18 Days On Market
      • Last Sold Price $349,900
      • Sep 11, 2023

      Last Listing Agent Daniel Pol Killington Pico Realty

  • /48

    $6,750,000 New Construction

    • 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
  • /25

    $525,000 Sold Oct 16, 2025

    19 Prospect St, Wood Stock, VT 05091

    • 2 Beds
    • 2 Baths
    • 1,482 Sq Ft
    • Built 1970

    Last Sold Summary

    • $354/SF
    • 2 Days On Market

    Current Estimated Value $517,425

    Last Listing Agent Katie McFadden RE/MAX North Professionals

    19 Prospect St, Wood Stock, VT 05091
    • /26

      Est $1,398,337 Not Listed For Sale

      76 Grove Hill Rd, Woodstock, VT 05091

      • 3 Beds
      • 2.5 Baths
      • 2,443 Sq Ft
      • Built 1983
      76 Grove Hill Rd, Woodstock, VT 05091

      Last Sold Summary

      • 1% Above List Price
      • $565/SF
      • 0 Days On Market
      • Last Sold Price $1,380,000
      • May 24, 2024

      Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  • /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
  • /43

    $2,350,000 Sold Dec 08, 2025

    2 Pleasant St, Woodstock, VT 05091

    • 4 Beds
    • 3.5 Baths
    • 3,998 Sq Ft
    • Built 1821

    Last Sold Summary

    • 10% Below List Price
    • $588/SF
    • 21 Days On Market

    Current Estimated Value $2,002,967

    Last Listing Agent David Donegan Snyder Donegan Real Estate Group

    2 Pleasant St, Woodstock, VT 05091
    • /40

      Est $845,385 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

      • 3% Below List Price
      • $475/SF
      • 8 Days On Market
      • Last Sold Price $875,000
      • Jul 25, 2024

      Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  • /47

    $395,000

    • 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
  • /36

    $1,300,000 Sold Nov 20, 2025

    13 College Hill Rd, Woodstock, VT 05091

    • 4 Beds
    • 3.5 Baths
    • 3,192 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Below List Price
    • $407/SF
    • 12 Days On Market

    Current Estimated Value $1,257,034

    Last Listing Agent Dail Frates Snyder Donegan Real Estate Group

    13 College Hill Rd, 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

      • $1,144/SF
      • 473 Days On Market
      • Last Sold Price $7,775,000
      • Dec 29, 2023

      Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  • /8

    $275,000

    • Land
    • 1.95 Acres
    • $141,026 per Acre

    3186 South Rd, Woodstock, VT 05091

    1.95 Acre lot minutes from Woodstock Village, South Woodstock, and Green Mountain Horse Association. Kidder Brook runs along the North property boundary, and a sunny lawn area has multiple small gardens. There is a large clearing, and a well-cared for 1973 mobile home on a concrete slab on the property. This lot has tremendous potential in a fantastic location. House is being sold As-is.

    Andrew Hubbell Vermont Real Estate Company

    3186 South Rd, Woodstock, VT 05091
  • /39

    $730,000 Sold Sep 26, 2025

    17 Golf Pond, Woodstock, VT 05091

    • 3 Beds
    • 2.5 Baths
    • 1,850 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Below List Price
    • $395/SF
    • 43 Days On Market

    Last Listing Agent Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

    17 Golf Pond, Woodstock, VT 05091
    • /38

      Est $1,164,034 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

      • 39% Above List Price
      • $563/SF
      • 5 Days On Market
      • Last Sold Price $840,000
      • Jan 05, 2024

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  • /26

    $479,000

    • 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
  • /33

    $776,000 Sold Aug 25, 2025

    3 Hathorn Hill St Unit 3, Woodstock, VT 05091

    • 3 Beds
    • 3 Baths
    • 2,552 Sq Ft
    • Built 1984

    Last Sold Summary

    • 1% Above List Price
    • $304/SF
    • 6 Days On Market

    Current Estimated Value $742,241

    Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

    3 Hathorn Hill St Unit 3, 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

      • $476/SF
      • 0 Days On Market
      • Last Sold Price $623,000
      • Jun 28, 2024

      Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  • /24

    $395,000 Open Fri 11AM - 2PM

    • 1 Bed
    • 1 Bath
    • 990 Sq Ft

    17 High St Unit 5, Woodstock, VT 05091

    Bathed in natural light from soaring skylights and perched above the rooftops of one of New England's most beloved villages, this charming one-bedroom condominium puts the very best of Woodstock, Vermont, at your doorstep. Just steps from the Woodstock Inn, the Village Green, and the town's finest restaurants and shops, this bright second-floor retreat offers a rare combination of walkable

    Dail Frates Snyder Donegan Real Estate Group

    17 High St Unit 5, 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 $866,621

    Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

    100 Pomfret Rd, Woodstock, VT 05091
    • /40

      Est $688,213 Not Listed For Sale

      3256 South Rd, Woodstock, VT 05091

      • 3 Beds
      • 2 Baths
      • 1,888 Sq Ft
      • Built 1884
      3256 South Rd, Woodstock, VT 05091

      Last Sold Summary

      • 10% Above List Price
      • $332/SF
      • 4 Days On Market
      • Last Sold Price $626,000
      • Jun 02, 2023

      Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  • /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

      Est $671,056 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

      • 36% Above List Price
      • $170/SF
      • 92 Days On Market
      • Last Sold Price $495,000
      • Oct 16, 2023

      Last Listing Agent John Wetmore Wetmore Real Estate

  • /55

    $1,145,000 Sold Aug 15, 2025

    2 Maple St, Woodstock, VT 05091

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

    Last Sold Summary

    • 5% Above List Price
    • $423/SF
    • 5 Days On Market

    Current Estimated Value $1,142,119

    Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

    2 Maple St, Woodstock, VT 05091

Showing Results 81 - 120, Page 3 of 18

How to Buy a Home How to Finance a Home How to Sell a Home