Windsor, VT Homes

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  /43

  $2,600,000

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

  2 Pleasant St, Woodstock, VT 05091

  2 PLEASANT STREET- This stately brick Federal is a historic landmark property in the heart of Woodstock Village, home to many storied families in the town and state’s history, notably Julius Converse, Governor of Vermont in 1872, and Laurance Rockefeller. Though it has been well-renovated and maintained over the years, it retains many of its historic features to beautifully blend modern

  David Donegan Snyder Donegan Real Estate Group

  2 Pleasant St, Woodstock, VT 05091
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  /5

  $1,450 per month

  • 1 Bed
  • 1 Bath
  • 8,400 Sq Ft
  • Apartment for Rent

  36 Happy Valley Rd, Woodstock, VT 05091

  Spacious and charming second-floor studio in a beautiful Historic home in the hamlet of Taftsville, Woodstock Vermont. Convenient Commute to Dartmouth College and Dartmouth - Hitchcock Medical Center with skiing and outdoor activities nearby. Rent includes all utilities: Heat, Hot Water, Electric, Wifi, parking and plowing. NO DRUGSOwner is Licensed Real

  Gail Childs Covered Bridge RE

  36 Happy Valley Rd, Woodstock, VT 05091
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  /33

  $776,000 Sold Aug 25, 2025

  • 2,552 Sq Ft
  • $304/SF
  • 6 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1984

  3 Hathorn Hill St Unit 3, Woodstock, VT 05091

  Rare opportunity to own in Hathorn Hill Condos. Private, quiet with lovely fern grove and stonewalls with views to the East. This unit has an de-attached 2 bay garage with easy access to extra parking. Upper level consist of an open floor plan, abundance of natural light with slider doors across the front for nice views off balcony. Living room anchored by a handsome wood burning fireplace

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  3 Hathorn Hill St Unit 3, Woodstock, VT 05091
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  /39

  Est $1,072,540 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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  /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
• 

  

  /15

  $2,595 per month

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Townhouse for Rent

  2 Townhouse Way, Woodstock, VT 05091

  Available November 1 2025 through April 30th 2026Fully Furnished. All utilities plus internet included - you write one check each month.Hello Lovers of Vermont Fall and Winter! Here is your chance to escape the hustle and bustle of your busy life in Vermont's premier village of Woodstock! This Townhouse is peaceful and private, with all the amenities to keep you in comfort AND quick

  Matt DePrizio Covered Bridge RE

  2 Townhouse Way, Woodstock, VT 05091
• 

  

  /40

  $740,000 Sold Aug 18, 2025

  • 2,688 Sq Ft
  • $275/SF
  • 67 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  339 Gully Rd, Woodstock, VT 05091

  Peaceful Gully Road Retreat. Just minutes from Woodstock Village.Set on 5.1 private acres along quiet and desirable Gully Road, this beautifully updated four-bedroom, two and one-half bath home offers the perfect blend of peaceful country living and convenient proximity to Woodstock shops, restaurants, and schools.The main level features a light-filled, open-concept layout with a dramatic

  Derek Cosentino Four Seasons Sotheby's Int'l Realty

  339 Gully Rd, Woodstock, VT 05091
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  /23

  Not Listed For Sale

  0 Carlton Hill Rd Unit 4670150, Woodstock, VT 05091

  0 Carlton Hill Rd Unit 4670150, 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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  /40

  $2,425,000 Sold Aug 15, 2025

  • 5,017 Sq Ft
  • $483/SF
  • 0 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2003

  739 Westerdale Rd, Woodstock, VT 05091

  Absolutely stunning, newly renovated residence, privately situated towards the end of a quiet town road in Woodstock, in an area of other substantial homes. Lovely mountain views and 10+ acres of privacy. The present owners have completed over $1 million in documented renovations in the past three years, including a fabulous new gourmet kitchen, powder bath, new bamboo flooring throughout the

  John Snyder Snyder Donegan Real Estate Group

  739 Westerdale Rd, 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

  $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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  /55

  $1,145,000 Sold Aug 15, 2025

  • 2,710 Sq Ft
  • $423/SF
  • 5 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2020

  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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  /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
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  /60

  $1,495,000 Under Contract

  • 4 Beds
  • 4 Baths
  • 2,408 Sq Ft

  6196 Stage Rd, Woodstock, VT 05091

  Perched on the shores of Silver Lake, this exceptional lakefront retreat blends timeless Vermont charm with modern craftsmanship. Custom-built in 2015 by Ambrose Custom Builders, the primary residence is designed to maximize lake views and natural light. Expansive windows frame the water, while thoughtful finishes, vaulted ceilings, wood detailing, and custom millwork create a warm yet refined

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  6196 Stage Rd, Woodstock, VT 05091
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  /26

  $480,000 Sold Aug 15, 2025

  • 930 Sq Ft
  • $516/SF
  • 98 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1860

  11A Prospect St, Woodstock, VT 05091

  Walk to everything Woodstock village has to offer from this sunny condo! Within an easy stroll of the Woodstock Inn, downtown restaurants, farmer's markets, and the Marsh Billings Rockefeller National Park, 11A Prospect is ideal for enjoying the charms of village living. Elevated above the Route 4 on a bucolic neighborhood side street, this well-kept home offers historic details with modern

  Keri Cole Williamson Group Sothebys Intl. Realty

  11A Prospect St, 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
• 

  

  /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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  /44

  $1,700,000 Sold Aug 15, 2025

  • 2,423 Sq Ft
  • $702/SF
  • 177 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2007

  2090 Randall Rd, Woodstock, VT 05091

  Constructed in 2007 with a nod to the Gothic Style Vermont Farmhouse vernacular, this beautifully composed country home creatively integrates curated period detail with modern conveniences and systems. Conveniently located at the end of a picturesque tree lined dirt road just minutes from the Villages of both Woodstock and South Woodstock offering privacy and tranquility. The interior spaces of

  Danny Kogut Williamson Group Sothebys Intl. Realty

  2090 Randall Rd, Woodstock, VT 05091
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  /27

  Est $695,515 Not Listed For Sale

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

  37 South St, Woodstock, VT 05091

  37 South St, Woodstock, VT 05091
• 

  

  /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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  /52

  $545,000 Sold Aug 06, 2025

  • 1,344 Sq Ft
  • $406/SF
  • 53 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1944

  1613 W Woodstock Rd, Woodstock, VT 05091

  OPEN HOUSE SUNDAY JUNE 15 FROM 12-3! Welcome to this turn-key, thoughtfully renovated home featuring a fully updated kitchen with granite countertops, stainless steel appliances, a gas stove, and a sliding glass door that opens to a covered porch—perfect for overlooking the spacious backyard. The main level offers a comfortable bedroom and a nearby full bath, while upstairs you'll find two

  Holly Hall Hall Collins Real Estate Group

  1613 W Woodstock Rd, Woodstock, VT 05091
• 

  

  /31

  Est $1,011,186 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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  /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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  /34

  $679,000 Sold Aug 04, 2025

  • 2,128 Sq Ft
  • $319/SF
  • 49 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1968

  294 Barberry Hill Rd, Woodstock, VT 05091

  Discover this delightful 3-bedroom, 2.5-bath home nestled on 1.8 acres at the end of a peaceful dead-end road. Conveniently located near Woodstock Middle/High School, the Thompson Senior Center, and the popular Woodstock Farmers’ Market.This home offers a spacious and functional layout, the welcoming mudroom features generous storage space and a laundry area cleverly tucked behind sliding

  Bonnie Bergeron Snyder Donegan Real Estate Group

  294 Barberry 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
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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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  /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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  /40

  Est $1,910,235 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 3,997 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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  /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
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  /40

  Est $576,510 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
• 

  

  /59

  $1,745,000

  • 2 Beds
  • 3 Baths
  • 2,106 Sq Ft

  7 North St, Woodstock, VT 05091

  Stunning Renovated Antique Cape in the Heart of Woodstock Village!Tucked away on over an acre of beautifully landscaped land directly abutting the Marsh-Billings-Rockefeller National Park, this fully renovated antique Cape offers the rare combination of historic charm, modern efficiency, and unbeatable walkability. Located in the heart of Woodstock Village, you can stroll to the village

  Keri Cole Williamson Group Sothebys Intl. Realty

  7 North St, Woodstock, VT 05091
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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
• 

  

  /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
• 

  

  /35

  $1,895,000

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

  10 College Hill Rd, Woodstock, VT 05091

  10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in

  John Snyder Snyder Donegan Real Estate Group

  10 College Hill Rd, 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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  /39

  Est $3,408,450 Not Listed For Sale

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

  3 Church St, Woodstock, VT 05091

  3 Church St, Woodstock, VT 05091
• 

  

  /39

  $610,000

  • 2 Beds
  • 2 Baths
  • 2,248 Sq Ft

  2456 Cox District Rd Unit 250.32.02.01, Woodstock, VT 05091

  This is a beautiful spacious Ranch. NEW Bosch furnace. New floors in basement. Basement has family room, and 2 large rooms with large windows and separate doors.Living room looks out to beautiful country settings. Large deck off living room.Dining room, eat in kitchen and BRAND NEW large custom bathroom on main floor, just finished yesterday!! This property has a pond and plush lawns.

  Dorothea Mongulla High End Realty

  2456 Cox District Rd Unit 250.32.02.01, 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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