Windsor, VT Homes

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  /49

  $1,595,000

  • 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 space, comfort, and classic Vermont charm. The expanded chef’s kitchen opens to a gracious gathering room ideal for entertaining, while 3 fireplaces—wood-burning, brick, and gas-ready—provide cozy warmth throughout. Upstairs, find 3–4 bedrooms including one with its own fireplace, plus a private guest room or

  Keri Cole Williamson Group Sothebys Intl. Realty

  1522 Barnard Rd, Woodstock, VT 05091
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  /23

  $1,995 per month

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

  36 Happy Valley Rd, Woodstock, VT 05091

  Lovely one bedroom unit in a Historic home, located in the Hamlet of Woodstock Vermont. Space is fully furnished or you may request it to be unfurnished if necessary. If you need a quiet place to come on the weekends, ski for the winter or simply have a new home this is your place. Heat, Electric, Water, Sewer, Trash, On site Parking, snow removal all included in rent.NO Pets, NO

  Gail Childs Covered Bridge RE

  36 Happy Valley Rd, Woodstock, VT 05091
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  /37

  $925,000 Sold Jul 31, 2025

  • 1,636 Sq Ft
  • $565/SF
  • 68 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1847

  4 River St, Woodstock, VT 05091

  This impeccably restored 1847 Woodstock village cape set upon a captivating river front landscape is truly magical! The complete and meticulous efficiency upgrades and renovations combined with the perfect village location offers an incomparable opportunity for those buyers coveting a village location. All new windows and red birch floors set the stage for the interior design. The sun-filled

  Mary Mayhew Snyder Donegan Real Estate Group

  4 River St, Woodstock, VT 05091
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  /39

  Est $1,152,009 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,507 Sq Ft

  433 Cowdrey Path, Woodstock, VT 05091

  433 Cowdrey Path, Woodstock, VT 05091
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  /48

  $1,749,000

  • 3 Beds
  • 3.5 Baths
  • 3,294 Sq Ft

  39 Elm St Unit B, Woodstock, VT 05091

  The Richmond House – Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a distinguished brick Federal with a softly weathered, rose-hued patina and elegant architectural details. Set on over an acre behind a classic white picket fence, this historic property—reimagined under the direction of Laurence Rockefeller—comprises three luxurious residences

  Zoe Hathorn Washburn Snyder Donegan Real Estate Group

  39 Elm St Unit B, Woodstock, VT 05091
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  /52

  $1,320,000 Sold Jul 25, 2025

  • 3,305 Sq Ft
  • $399/SF
  • 85 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1919

  11 College Hill Rd, Woodstock, VT 05091

  Welcome to 11 College Hill Road - Situated in the heart of Woodstock Village, this classic 1919 Gambrel offers space, charm, and incredible views of both the Ottauquechee River and the town's beloved Mount Tom. This beautifully maintained home is perched perfectly above the river with over a half an acre of landscaped outdoor space, including 50 feet of river frontage, mature fruit trees, and

  Zoe Hathorn Washburn Snyder Donegan Real Estate Group

  11 College Hill Rd, Woodstock, VT 05091
• 

  

  /23

  Not Listed For Sale

  0 Carlton Hill Rd Unit 4670150, Woodstock, VT 05091

  0 Carlton Hill Rd Unit 4670150, Woodstock, VT 05091
• 

  

  /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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  /41

  $1,075,000 Sold Jul 15, 2025

  • 3,060 Sq Ft
  • $351/SF
  • 353 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1985

  119 English Mills Way, Woodstock, VT 05091

  An expansive 5 bedroom home, in a private location, conveniently just a few minutes drive from Woodstock Village! Among often sought amenities are a ground floor primary bedroom suite with private bath, a dramatic great room with cathedral ceiling and wood burning fireplace, a generously sized lower level in-law/guest suite with kitchen, dining, living room and bedroom with bath, 3 additional

  John Wetmore Wetmore Real Estate

  119 English Mills Way, Woodstock, VT 05091
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  /27

  Est $827,352 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,579 Sq Ft

  7 Golf Ave, Woodstock, VT 05091

  7 Golf Ave, Woodstock, VT 05091
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  /40

  $2,299,000

  • 6 Beds
  • 6 Baths
  • 7,619 Sq Ft

  5518 Vermont 12, Woodstock, VT 05091

  An historic brick residence prominently located in an affluent and growing community! Conveniently situated within walking distance to the Elementary School, to year round recreation on beloved Silver Lake and to the classic Barnard General Store. All the amenities of Woodstock Village are just minutes away! World class medical care at Dartmouth Hitchcock Hospital and year round cultural events

  John Wetmore Wetmore Real Estate

  5518 Vermont 12, Woodstock, VT 05091
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  /51

  $1,300,000 Sold Jul 02, 2025

  • 4,228 Sq Ft
  • $307/SF
  • 91 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1980

  608 Fletcher Hill Rd, Woodstock, VT 05091

  Open House Sunday, April 13, 12:00 to 2:00 - Tucked away in the serene forests of Woodstock, Vermont, this beautifully remodeled 11-room home offers 4 bedrooms, 4 bathrooms, and 4,225 sq. ft. of luxurious living space on 5.4 private acres. The open-concept design is flooded with natural light, featuring a stunning chef’s kitchen with high-end stainless steel appliances, Vermont soapstone

  Sandy Reavill Real Broker LLC

  608 Fletcher Hill Rd, Woodstock, VT 05091
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  /30

  Est $973,995 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,423 Sq Ft

  12 High St, Woodstock, VT 05091

  12 High St, Woodstock, VT 05091
• 

  

  /22

  $645,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,468 Sq Ft

  187 Dana Rd, Woodstock, VT 05091

  This delightful gambrel cape offers a wonderful combination of thoughtful and charming updates, energy efficient upgrades, and a coveted and convenient location! An intelligent interior design offers an all-season functional flow for everyday living as well as entertaining. Step inside by way of a spacious entryway/mudroom that also has direct entry from the attached garage. One will find the

  Mary Mayhew Snyder Donegan Real Estate Group

  187 Dana Rd, Woodstock, VT 05091
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  /31

  $475,000 Sold Jun 16, 2025

  • 2,091 Sq Ft
  • $227/SF
  • 29 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1978

  85 Townhouse Way Unit 18, Woodstock, VT 05091

  Fully furnished and equipped condo nestled in a small quiet community just 5 minutes from historic Woodstock. This is an end unit in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. New windows throughout. Spacious living room anchored by a wood burning fireplace with hardwood floors. A couple of steps down takes you

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  85 Townhouse Way Unit 18, Woodstock, VT 05091
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  /38

  Est $553,300 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,020 Sq Ft

  39 South St, Woodstock, VT 05091

  39 South St, Woodstock, VT 05091
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  /40

  $1,650,000

  • 4 Beds
  • 3 Baths
  • 2,619 Sq Ft

  441 Spruce Way, Woodstock, VT 05091

  441 SPRUCE WAY - Easily accessible to the village, yet tucked away on over 24 acres is this unique, modern/contemporary residence designed by Boston architect Ken McKinzie and sited perfectly to take in south-facing long range mountain views. The house was designed to be perfect for two, with the primary bedroom suite on the main living level, yet with two bedrooms and a bath at the other end of

  John Snyder Snyder Donegan Real Estate Group

  441 Spruce Way, Woodstock, VT 05091
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  /54

  $1,500,000 Sold Jun 09, 2025

  • 3,012 Sq Ft
  • $498/SF
  • 68 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1971

  22 Orchard Hill Rd, Woodstock, VT 05091

  LICHENVALE at 22 Orchard Hill Road in Pomfret is a traditional Royal Barry Wills designed cape situated to capture sweeping views south down the Pomfret Valley to Mt. Tom, and the hills surrounding Woodstock Village. The well-cared for dwelling is naturally landscaped with mature gardens, and stone walls and sited on a level plateau at the margins of an open meadow below and the forested hillside

  Laird Bradley Williamson Group Sothebys Intl. Realty

  22 Orchard Hill Rd, Woodstock, VT 05091
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  /27

  Est $713,457 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft

  37 South St, Woodstock, VT 05091

  37 South St, Woodstock, VT 05091
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  /37

  $1,185,000

  • 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
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  /32

  $700,000 Sold May 30, 2025

  • 1,520 Sq Ft
  • $461/SF
  • 0 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1880

  13 Golf Ave, Woodstock, VT 05091

  Charming circa 1880 cape in Woodstock Village! Located on a quiet dead-end street across from Mt Peg trail head... Walk to all of towns amenities, shops, restaurants and events on Historic Woodstock Green. Championship golf, fly fishing and skiing near by. This lovely antique cottage has hardwood floors through out, open kitchen with first floor laundry. Adjacent is sitting area and dining.

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  13 Golf Ave, Woodstock, VT 05091
• 

  

  /31

  Est $974,978 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,970 Sq Ft

  10 Linden Hill, Woodstock, VT 05091

  10 Linden Hill, 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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  /36

  $1,800,000 Sold May 23, 2025

  • 4,100 Sq Ft
  • $439/SF
  • 61 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 2008

  484 Carlton Hill Rd, Woodstock, VT 05091

  Make this unique Adirondack-style home, with its rich stone and timber frame, and perfect location along the banks of the Ottauquechee River, your new Vermont retreat. Every window offers a stunning view of Mt. Tom, and the rushing river, making it a nature lover's paradise. The fieldstone fireplace soars two stories high in the great room, which is flooded with natural light through expansive

  Jennifer Kirkman KW Vermont Woodstock

  484 Carlton Hill Rd, Woodstock, VT 05091
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  /40

  Est $1,701,467 Not Listed For Sale

  • 6 Beds
  • 6 Baths
  • 3,892 Sq Ft

  28 The Green Unit 30, Woodstock, VT 05091

  28 The Green Unit 30, Woodstock, VT 05091
• 

  

  /27

  $1,200,000

  • 5 Beds
  • 4.5 Baths
  • 2,686 Sq Ft

  19 Church St Unit EX, Woodstock, VT 05091

  Bright and spacious five bedroom, five bath in-village residence with Ottauquechee River frontage and less than 1-minute walk to the Woodstock Green. 2-car attached garage enters into the kitchen via a mud-laundry room. Eat-in kitchen with stainless appliances, granite countertops and a large sunny bay window leads to the formal dining room, and also opens to the patio, perfect for entertaining

  John Snyder Snyder Donegan Real Estate Group

  19 Church St Unit EX, Woodstock, VT 05091
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  /49

  $875,000 Sold May 16, 2025

  • 2,034 Sq Ft
  • $430/SF
  • 19 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1992

  19 Linden Hill St, Woodstock, VT 05091

  Perched along scenic Linden Hill, this stunning village home offers exceptional privacy, comfort, and spacious interiors. A paved driveway leads to a one-car garage with a covered entrance, ensuring effortless access in all seasons.Inside, a generous mudroom provides a practical transition into the inviting living room, featuring a cozy propane fireplace, or the well-appointed kitchen with sleek

  Holly Hall Hall Collins Real Estate Group

  19 Linden Hill St, Woodstock, VT 05091
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  /40

  Est $1,781,111 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 5,897 Sq Ft

  2 Border Ln, Woodstock, VT 05091

  2 Border Ln, Woodstock, VT 05091
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  /54

  $1,690,000

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

  687 S Perry Rd, Woodstock, VT 05091

  Privately sited on a knoll to capture sweeping North Westerly views, this expanded Classic Cape has been lovingly stewarded and tastefully updated over the years. Enter through the formal foyer with wainscot, or a convenient mudroom with powder room. Superior craftsmanship throughout featuring a beautifully appointed chef's kitchen with Viking range-top, wall ovens and best quality appliances,

  Danny Kogut Williamson Group Sothebys Intl. Realty

  687 S Perry Rd, Woodstock, VT 05091
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  /17

  $86,500 Sold May 16, 2025

  • 1,120 Sq Ft
  • $77/SF
  • 86 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2011

  132 Riverbend Way, Woodstock, VT 05091

  Wonderful Woodstock location!!! 3 bedroom single wide mobile home ready for the new owner! Open concept kitchen and living room with plenty of closet space. Outside there is a large storage shed, a front porch and a deck under the tree. This home sits on a large corner lot! Only 13 miles to I-89!!

  Jenna Luce RE/MAX Upper Valley

  132 Riverbend Way, Woodstock, VT 05091
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  /40

  Est $587,072 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,368 Sq Ft

  1 Border Ln, Woodstock, VT 05091

  1 Border Ln, Woodstock, VT 05091
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  /34

  $2,199,000

  • 4 Beds
  • 3.5 Baths
  • 3,564 Sq Ft

  15 Hathorn Hill Street Extension, Woodstock, VT 05091

  An incredibly rare combination of in-Village and country living. 4+ acres and privacy with a pond and heated in-ground pool, yet walk-to-the Green. The residence, designed and built by the well-respected design-build firm Ambrose Construction, offers modern amenities, appliances and construction with a “Vermont Farmhouse” aesthetic. The vaulted ceiling timber frame great-gathering room has

  John Snyder Snyder Donegan Real Estate Group

  15 Hathorn Hill Street Extension, Woodstock, VT 05091
• 

  

  /40

  $575,000 Sold May 09, 2025

  • 1,700 Sq Ft
  • $338/SF
  • 274 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1848

  105 Happy Valley Rd, Woodstock, VT 05091

  PRICE REDUCTION!! A Quintessential Historic 3 Bedroom, 1,700 sq/ft. Home in Woodstock's coveted Taftsville Village. The "Levi D. Hall House" was built in 1848 by D. Taft & Sons and has been a loved and well-maintained home by the same family for nearly 70 years. Enter into beautiful natural light and a home in pristine condition throughout. The classic country kitchen has high ceilings with

  John Bassette Bassette Real Estate Group

  105 Happy Valley Rd, Woodstock, VT 05091
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  /40

  Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,305 Sq Ft

  11 College Hill Rd, Woodstock, VT 05091

  11 College Hill Rd, Woodstock, VT 05091
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  /43

  $1,395,000

  • 4 Beds
  • 3 Baths
  • 4,864 Sq Ft

  15 Central St, Woodstock, VT 05091

  15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The property has adapted to changes of the course of its long history of uses including residential shop owner, a barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building

  Laird Bradley Williamson Group Sothebys Intl. Realty

  15 Central St, Woodstock, VT 05091
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  /20

  $2,900,000 Sold May 05, 2025

  • 3,550 Sq Ft
  • $817/SF
  • 0 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1986

  3086 South Rd, Woodstock, VT 05091

  Beautifully and extensively renovated residence, newer construction barn-garage with five overhead doors and an attached one-bedroom apartment (ADU). The land component offers over a mile of private trails perfect for walking, horseback, snowshoeing and biking, including a coursing stream with waterfalls, open meadows, a sledding hill and beautiful landscaping. Detached screened porch and stone

  John Snyder Snyder Donegan Real Estate Group

  3086 South Rd, Woodstock, VT 05091
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  /39

  Est $3,387,678 Not Listed For Sale

  • 10 Beds
  • 15 Baths
  • 10,206 Sq Ft

  3 Church St, Woodstock, VT 05091

  3 Church St, Woodstock, VT 05091
• 

  

  /55

  $1,095,000 Pending

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

  2 Maple St, Woodstock, VT 05091

  Located in the Heart of Woodstock Village- fantastic location at the foot of the Mtn Peg trail system with easy access to Vail field and all of towns amenities. This beautifully renovated home is completely new. Handsome farmhouse vernacular style home with traditional slate floors, sliding barn doors and wood floors throughout first floor with an open concept for entertaining and all new

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  2 Maple St, Woodstock, VT 05091
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  /40

  $750,000 Sold May 01, 2025

  • 1,840 Sq Ft
  • $408/SF
  • 43 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1970

  6963 South Rd, Woodstock, VT 05071

  Enchanting cottage perched on a private knoll with short range views. This property consist of 33 acres with a mixture of open meadow and woods for those looking for an afternoon of walking or snowshoeing. It is currently enrolled in the Current Use Forestry program. Stunning perennial gardens enhance the handsome stone walls and stone walk way to the residence. It's a Garden enthusiasts

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  6963 South Rd, Woodstock, VT 05071
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  /40

  Est $1,580,609 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 3,719 Sq Ft

  26 River St, Woodstock, VT 05091

  26 River St, Woodstock, VT 05091

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