Windsor, VT Homes

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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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  /11

  $1,450 per month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  1711 W Woodstock Rd Unit 5, Woodstock, VT 05091

  2nd floor, one bedroom in a multi-family home in West Woodstock. The bedroom has two spacious closets, high ceilings and an additional cable hookup. The unit has a full bathroom with shower & tub. There is a washer and dryer in the unit. Off street parking. This property sits about 30 feet off of US rt 4. This unit is in the front of the building. Access from outdoor uncovered staircase. The

  Matt DePrizio Covered Bridge RE

  1711 W Woodstock Rd Unit 5, Woodstock, VT 05091
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  /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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  /40

  Est $1,410,277 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,440 Sq Ft

  4946 South Rd, South Woodstock, VT 05071

  4946 South Rd, South Woodstock, VT 05071
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  /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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  /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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  /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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  /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
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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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  /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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  /42

  $8,000,000

  • 3 Beds
  • 3.5 Baths
  • 6,096 Sq Ft

  115 Eastman Rd, South Woodstock, VT 05071

  Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

  Keri Cole

  115 Eastman Rd, South Woodstock, VT 05071
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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
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  /40

  Est $914,902 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 2,555 Sq Ft

  3090 South Rd, Woodstock, VT 05091

  3090 South Rd, 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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  /37

  Est $1,177,591 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,949 Sq Ft

  326 Hall Cir, Woodstock, VT 05091

  326 Hall Cir, Woodstock, VT 05091
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  /60

  $1,995,000

  • 3 Beds
  • 2.5 Baths
  • 5,422 Sq Ft

  2334 South Rd, Woodstock, VT 05091

  Offered for the first time, the exclusive private residence of one of Woodstock's most notable and prolific builders, Hank Savelberg. Located just five minutes from the Woodstock Village Green, this whimsical, private, contemporary hillside estate was lovingly constructed featuring well thought, connected open spaces with expansive glass walls and dramatic sweeping wooden ceilings. The entire

  Danny Kogut Williamson Group Sothebys Intl. Realty

  2334 South Rd, 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
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  /30

  Est $1,635,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,218 Sq Ft

  2409 South Rd, Woodstock, VT 05091

  2409 South Rd, Woodstock, VT 05091
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  /43

  $1,950,000

  • 5 Beds
  • 3.5 Baths
  • 3,502 Sq Ft

  4945 South Rd, Woodstock, VT 05071

  The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the area's earliest settlers, this stately Federal-style brick home has been thoughtfully restored to honor its historic charm while integrating modern comforts. Set on 2.7 acres, the property features 450 ft of frontage on Kedron

  Story Jenks LandVest, Inc/Woodstock

  4945 South Rd, Woodstock, VT 05071
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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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  /40

  Est $1,217,287 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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  /60

  $1,800,000

  • 4 Beds
  • 3.5 Baths
  • 5,000 Sq Ft

  2706 E Woodstock Rd, Woodstock, VT 05091

  INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store - Woodstock VT) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential downtown New England Village of Woodstock! Property includes storefront space (approved for restaurant, cafe, or retail store), Post Office (with current

  John Bassette Bassette Real Estate Group

  2706 E Woodstock Rd, Woodstock, VT 05091
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  /28

  $882,500 Sold Jun 18, 2025

  • 1,616 Sq Ft
  • $546/SF
  • 111 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  46 Stewart Ln Unit P-304, Ludlow, VT 05149

  Winterplace on Okemo Mountain – A One-of-a-Kind Opportunity! Discover the ultimate mountain retreat at Winterplace, one of Okemo's most sought-after condominium complexes. This exceptional top-floor, 3-bedroom plus loft condominium has been beautifully remodeled, blending modern comfort with classic alpine charm. The expanded loft has been transformed into a spacious second living area, perfect

  Katherine Burns William Raveis Real Estate Vermont Properties

  46 Stewart Ln Unit P-304, Ludlow, VT 05149
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  /40

  Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 4,510 Sq Ft

  5798 South Rd, Woodstock, VT 05071

  5798 South Rd, Woodstock, VT 05071
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  /40

  $1,875,000 Pending

  • 10 Beds
  • 12 Baths
  • 7,769 Sq Ft

  2709 W Woodstock Rd, Woodstock, VT 05091

  INVESTMENT, MULTI-GENERATIONAL, MULTI FAMILY AND COMMERCIAL OPPORTUNITY .. priced below appraised value on land and buildings providing instant equity. Experience the charm of Woodstock, VT with its quaint Main Street and enjoy the proximity to Killington Resort, just a short drive away. This exceptional property offers a unique blend of natural beauty and year-round recreational opportunities,

  Susan Bishop Four Seasons Sotheby's Int'l Realty

  2709 W Woodstock 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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  /40

  Est $1,575,566 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,329 Sq Ft

  282 Fletcher Hill Rd, Woodstock, VT 05091

  282 Fletcher Hill Rd, Woodstock, VT 05091
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  /38

  $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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  /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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  /32

  Est $540,777 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  35 White Loop Unit B-102, Ludlow, VT 05149

  35 White Loop Unit B-102, Ludlow, VT 05149
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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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  /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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  /34

  Est $585,073 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,196 Sq Ft

  1782 South Rd, Woodstock, VT 05091

  1782 South Rd, Woodstock, VT 05091
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  /39

  $619,000

  • 4 Beds
  • 2 Baths
  • 1,654 Sq Ft

  4165 Hartland Hill Rd, Woodstock, VT 05091

  A professionally renovated classic cape, in a convenient Woodstock location! The interior appeals as fresh and new! The property presents itself as truly turn-key ready for a next owner! With 4 bedrooms and 2 full baths, this cape can easily fill a role of weekend retreat, with room to accommodate visiting friends! As a primary residence, the practical floor plan provides a good combination of

  John Wetmore Wetmore Real Estate

  4165 Hartland Hill Rd, Woodstock, VT 05091
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  /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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  /38

  Est $1,559,560 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,350 Sq Ft

  2876 Hartland Hill Rd, Woodstock, VT 05091

  2876 Hartland Hill Rd, Woodstock, VT 05091
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  /18

  $239,500

  • 1 Bed
  • 1 Bath
  • 856 Sq Ft

  56 Heritage Condo Way Unit 9, Woodstock, VT 05091

  Lots of upgrades to this quiet, two level condo, with lovely views off back baloney. Bonus- new mini split heat pump providing both air conditioning and heat. Kitchen has some upgraded as well with a new dishwasher. This open floor concept condo provides lots of natural sunlight. Cozy up in the living room/dining room and read a book during the winter months overlooking the spacious

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  56 Heritage Condo Way Unit 9, 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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