Woodstock, VT Homes

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  /40

  $1,295,000

  • 4 Beds
  • 3 Baths
  • 3,089 Sq Ft

  16 Church St, Woodstock, VT 05091

  16 Church has the most stunning view of the river from any house in the village that we have seen, perched up above a series of river rapids so the sounds of the river during the day or in the evening are incredibly peaceful and relaxing. Plus, 16 Church is privately nestled in, like a secret hideaway, yet steps to the village green (and a level walk to/from). And more unusual for the village,

  John Snyder Snyder Donegan Real Estate Group

  16 Church St, Woodstock, VT 05091
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  /44

  $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 $1,657,301

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  2090 Randall Rd, Woodstock, VT 05091
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  /40

  Est $820,577 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  25 Slayton Terrace, Woodstock, VT 05091

  25 Slayton Terrace, Woodstock, VT 05091
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  /11

  $149,000

  • Land
  • 3.54 Acres
  • $42,090 per Acre

  00 Carlton Hill Rd Unit 27, Woodstock, VT 05091

  Discover the beauty of Vermont from this diverse 3.5-acre parcel along Carlton Hill Road, set in a peaceful rural location amid a neighborhood of substantial properties. With level access from a well-maintained town road, this land offers an inviting blend of convenience and natural charm. Just minutes from the vibrant shops, dining, and cultural attractions of Woodstock Village, the property

  Sandy Reavill Real Broker LLC

  00 Carlton Hill Rd Unit 27, Woodstock, VT 05091
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  /40

  $2,750,000 Sold Feb 13, 2025

  318 Ebbin Lockwood Way, Woodstock, VT 05071

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

  Last Sold Summary

  • 20% Below List Price
  • $455/SF
  • 495 Days On Market

  Last Listing Agent Story Jenks LandVest, Inc/Woodstock

  318 Ebbin Lockwood Way, Woodstock, VT 05071
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  /40

  Est $986,314 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,136 Sq Ft

  77 Central St, Woodstock, VT 05091

  77 Central St, Woodstock, VT 05091
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  /41

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 2,532 Sq Ft

  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 Sothebys Intl. Realty

  7 Slayton Terrace, Woodstock, VT 05091
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  /57

  $1,710,000 Sold Dec 05, 2025

  20 The Green, Woodstock, VT 05091

  • 3 Beds
  • 2.5 Baths
  • 2,688 Sq Ft
  • Built 1826

  Last Sold Summary

  • 14% Below List Price
  • $636/SF
  • 139 Days On Market

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  20 The Green, Woodstock, VT 05091
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  /40

  Est $3,158,040 Not Listed For Sale

  • 7 Beds
  • 4.5 Baths
  • 5,306 Sq Ft

  4 Bond St, Woodstock, VT 05091

  4 Bond St, Woodstock, VT 05091
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  /40

  $3,500,000

  • 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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  /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 $615,524

  Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  40 Pomfret Rd, Woodstock, VT 05091
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  /35

  Not Listed For Sale

  • 7 Beds
  • 5.5 Baths
  • 6,472 Sq Ft

  3 Bond St, Woodstock, VT 05091

  3 Bond St, Woodstock, VT 05091
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  /50

  $1,100,000

  • 3 Beds
  • 2.5 Baths
  • 2,220 Sq Ft

  958 E Woodstock Rd, Woodstock, VT 05091

  Just minutes from the heart of Woodstock, this 3-bedroom, 3-bath home with a dedicated office/family room has been transformed from the ground up into a modern, energy-efficient retreat. Taken down to the studs, the renovation was comprehensive—every system replaced, with all new wiring, plumbing, insulation, and mechanicals, along with a new roof, Pella windows, central heating, and air

  Keri Cole Williamson Group Sothebys Intl. Realty

  958 E Woodstock Rd, Woodstock, VT 05091
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  $1,275,000 Sold Apr 02, 2025

  1075 Westerdale Rd, Woodstock, VT 05091

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

  Last Sold Summary

  • 9% Below List Price
  • $493/SF
  • 72 Days On Market

  Current Estimated Value $1,281,555

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  1075 Westerdale Rd, Woodstock, VT 05091
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  /40

  Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,488 Sq Ft

  28 Pleasant St, Woodstock, VT 05091

  28 Pleasant St, Woodstock, VT 05091
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  /43

  $595,000

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

  1514 South Rd, Woodstock, VT 05091

  This tidy, well maintained Mid-Century Ranch home is conveniently located just 1.5 miles from the Village Green. Perched on a sunny knoll with a southern valley view, this well maintained home features open concept kitchen/dining, a large, bright living room, three bedrooms all with oak floors, a walk out basement providing opportunity for guest accommodation, or a hobby/play room. The 2 car

  Danny Kogut Williamson Group Sothebys Intl. Realty

  1514 South Rd, Woodstock, VT 05091
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  /40

  $750,000 Sold May 01, 2025

  6963 South Rd, Woodstock, VT 05071

  • 2 Beds
  • 1.5 Baths
  • 1,840 Sq Ft
  • Built 1970

  Last Sold Summary

  • 6% Below List Price
  • $408/SF
  • 43 Days On Market

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  6963 South Rd, Woodstock, VT 05071
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  /21

  Est $530,469 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,060 Sq Ft

  193 Hartland Hill Rd, Woodstock, VT 05091

  193 Hartland Hill Rd, Woodstock, VT 05091
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  /6

  $239,000

  • 2 Beds
  • 1 Bath
  • 1,190 Sq Ft

  442 E Woodstock Rd Unit 4A, Woodstock, VT 05091

  Airy, tranquil and quiet, this former yoga studio space has been converted into a two bedroom condo. Sweeping views through the Palladian window, large living area with soaring vaulted ceiling, newer kitchen with granite counters and newer bath with walk in shower. Spacious entry can accommodate bikes, skis and more. Walking distance to shops, restaurants, entertainment and recreation in the

  Jane Darrach Martha E. Diebold/Hanover

  442 E Woodstock Rd Unit 4A, Woodstock, VT 05091
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  /51

  $1,300,000 Sold Jul 02, 2025

  608 Fletcher Hill Rd, Woodstock, VT 05091

  • 4 Beds
  • 3.5 Baths
  • 4,228 Sq Ft
  • Built 1980

  Last Sold Summary

  • 13% Below List Price
  • $307/SF
  • 91 Days On Market

  Current Estimated Value $1,226,755

  Last Listing Agent Sandy Reavill Real Broker LLC

  608 Fletcher Hill Rd, Woodstock, VT 05091
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  /40

  Est $1,159,112 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,130 Sq Ft

  8 Garvin Hill Rd, Woodstock, VT 05091

  8 Garvin Hill Rd, Woodstock, VT 05091
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  $525,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,557 Sq Ft

  144 Butternut Ln, Woodstock, VT 05091

  NEW PRICE!! Discover classic Vermont charm at The Harry Emmons House, an antique brick cape located in the village of Taftsville, ideally situated on a level, open lot. A traditional covered farm porch leads to a gathering room with a brick fireplace. The main level features bright, airy living spaces with high ceilings and exposed beams, comfortable rooms, a country kitchen, a sunny dining room,

  Scott Monahan Williamson Group Sothebys Intl. Realty

  144 Butternut Ln, Woodstock, VT 05091
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  /24

  $230,000 Sold Mar 26, 2025

  29 Heritage Condos Unit 29D, Woodstock, VT 05091

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

  Last Sold Summary

  • $269/SF
  • 3 Days On Market

  Last Listing Agent Franchesca Collins Hall Collins Real Estate Group

  29 Heritage Condos Unit 29D, Woodstock, VT 05091
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  /39

  Est $649,667 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,263 Sq Ft

  200 Garvin Hill Rd, Woodstock, VT 05091

  200 Garvin Hill Rd, Woodstock, VT 05091
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  /18

  $300,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft

  17 High St Unit 2, Woodstock, VT 05091

  Charming Woodstock Condo in Prime LocationLocated in the highly desirable High Street neighborhood of Woodstock, this 2-bedroom condo offers the perfect blend of convenience and charm. Just steps from cafes, restaurants, and village amenities, the property provides easy access to everything the village has to offer. A highlight of the home is the inviting screened porch, perched above the

  Terry Davis Williamson Group Sothebys Intl. Realty

  17 High St Unit 2, Woodstock, VT 05091
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  /34

  $679,000 Sold Aug 04, 2025

  294 Barberry Hill Rd, Woodstock, VT 05091

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

  Last Sold Summary

  • $319/SF
  • 49 Days On Market

  Current Estimated Value $668,934

  Last Listing Agent Bonnie Bergeron Snyder Donegan Real Estate Group

  294 Barberry Hill Rd, Woodstock, VT 05091
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  /40

  Est $844,563 Not Listed For Sale

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

  3090 South Rd, Woodstock, VT 05091

  3090 South Rd, Woodstock, VT 05091
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  $845,000

  • 2 Beds
  • 1.5 Baths
  • 1,714 Sq Ft

  403 Horse Shoe Way, Woodstock, VT 05071

  Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials.The home was carefully, and

  Danny Kogut Williamson Group Sothebys Intl. Realty

  403 Horse Shoe Way, Woodstock, VT 05071
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  /36

  $1,800,000 Sold May 23, 2025

  484 Carlton Hill Rd, Woodstock, VT 05091

  • 4 Beds
  • 5 Baths
  • 4,100 Sq Ft
  • Built 2008

  Last Sold Summary

  • $439/SF
  • 61 Days On Market

  Current Estimated Value $1,792,539

  Last Listing Agent Jennifer Kirkman KW Vermont Woodstock

  484 Carlton Hill Rd, Woodstock, VT 05091
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  /37

  Est $1,109,201 Not Listed For Sale

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

  326 Hall Cir, Woodstock, VT 05091

  326 Hall Cir, Woodstock, VT 05091
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  $2,395,000

  • 4 Beds
  • 2 Baths
  • 3,000 Sq Ft

  1362 Barnard Rd, Woodstock, VT 05091

  Gilbert’s Hill: The birthplace of American skiing and one of Vermont's most celebrated properties for its contribution to the ski industry. Spanning 112.88± acres in Woodstock (79.31 acres) and Pomfret (33.57 acres), the farm is recognized as the birthplace of lift-served skiing in America, where the first rope tow was installed in 1934. Today, its open pastures, rolling terrain, and historic ski

  Chris Lang

  1362 Barnard Rd, Woodstock, VT 05091
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  /20

  $2,900,000 Sold May 05, 2025

  3086 South Rd, Woodstock, VT 05091

  • 4 Beds
  • 4.5 Baths
  • 3,550 Sq Ft
  • Built 1986

  Last Sold Summary

  • 12% Above List Price
  • $817/SF
  • 0 Days On Market

  Current Estimated Value $3,033,611

  Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  3086 South Rd, Woodstock, VT 05091
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  /30

  Est $1,129,928 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,758 Sq Ft

  2409 South Rd, Woodstock, VT 05091

  2409 South Rd, Woodstock, VT 05091
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  /60

  $869,000 Under Contract

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

  3961 Hartland Hill Rd, Woodstock, VT 05091

  This lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting less than a mile to village shopping, schools, dining and recreation. Updated with modern finishes to enhance accessibility and one level living-while maintaining the warm, country charm. First floor features a

  Tambrey Vutech KW Vermont Woodstock

  3961 Hartland Hill Rd, Woodstock, VT 05091
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  /31

  $920,000 Sold Nov 17, 2025

  348 Laughlin Rd, Woodstock, VT 05091

  • 4 Beds
  • 3 Baths
  • 2,882 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $319/SF
  • 7 Days On Market

  Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  348 Laughlin Rd, Woodstock, VT 05091
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  /40

  Est $1,149,412 Not Listed For Sale

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

  513 Deer Brook Way, Woodstock, VT 05091

  513 Deer Brook Way, Woodstock, VT 05091
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  /55

  $915,000

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

  509 Church Hill Rd, Wood Stock, VT 05091

  Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens.The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes ,

  Carol Wood Williamson Group Sothebys Intl. Realty

  509 Church Hill Rd, Wood Stock, VT 05091
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  /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
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  /40

  Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 3,910 Sq Ft

  5798 South Rd, Woodstock, VT 05071

  5798 South Rd, Woodstock, VT 05071
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  /35

  $549,000

  • 4 Beds
  • 3 Baths
  • 2,470 Sq Ft

  3364 W Woodstock Rd, Woodstock, VT 05091

  Welcome to this lovingly updated antique Cape, set on two open, level acres across from the sparkling Ottauquechee River. Just five minutes from Woodstock Village and perfectly positioned on the west side for quick trips to Killington and Pico, this home makes the ideal Vermont getaway.Inside, you’ll find four comfortable bedrooms and a warm, inviting layout designed for making memories.

  Keri Cole Williamson Group Sothebys Intl. Realty

  3364 W Woodstock Rd, Woodstock, VT 05091

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