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Woodstock, VT Houses for Sale

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  • /51

    $1,995,000

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

    20 The Green, Woodstock, VT 05091

    Stunning antique cape! Located in the 'heart' of Woodstock. Originally located on Central Street- this home was moved in the 1960's to this location and had an extensive renovation in 2011. The antique brick section was built in 1826- it boasts a spacious living room anchored with a large wood burning fireplace, original wide pine floors and lots of space for entertaining. Adjacent find a

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    20 The Green, Woodstock, VT 05091
  • /35

    $1,999,000

    • 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
  • /54

    $1,695,000

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

    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
  • /40

    $2,250,000

    • 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
  • /53

    $1,399,000

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

    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
  • /60

    $2,450,000

    • 4 Beds
    • 3.5 Baths
    • 5,573 Sq Ft

    851 Riverside Park Rd, Woodstock, VT 05091

    "All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style home, just over five minutes from Woodstock Village via Route 4 and the Lincoln Covered Bridge, sits high on a knoll above the Ottauquechee River with views to Killington. A veritable mini-resort, the property offers

    Richard Higgerson Higgerson & Company

    851 Riverside Park Rd, Woodstock, VT 05091
  • /60

    $2,000,000

    • 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) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential New England Village of Woodstock! Property includes store with bath (approved for restaurant, café, or retail store), Post Office (with current lease), Apartment 1

    John Bassette Bassette Real Estate Group

    2706 E Woodstock Rd, Woodstock, VT 05091
  • /40

    $775,000

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

    339 Gully Rd, Woodstock, VT 05091

    Peaceful Gully Road Retreat – Just minutes from Woodstock VillageSet 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’s 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
  • /60

    $615,000

    • 4 Beds
    • 3 Baths
    • 2,678 Sq Ft

    20 Gully Rd, Woodstock, VT 05091

    AGGRESSIVE PRICE REDUCTION - Classic Vermont Antique Farmhouse just outside of Woodstock Village! c.1903 Dormered Cape set on approx. 2.6 acres of level, open land bordered by a tranquil brook. The property offers a picturesque setting with extensive perennial gardens, a patio by the stream, firepits, covered front porch, rear porch, and deck—perfect for relaxing or entertaining. Inside, the home

    John Bassette Bassette Real Estate Group

    20 Gully Rd, Woodstock, VT 05091
  • /19

    $669,000

    • 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
  • /48

    $795,000

    • 3 Beds
    • 2 Baths
    • 1,694 Sq Ft

    25 Linden Hill St, Woodstock, VT 05091

    This classic early 20th Century farmhouse with 3 sunny bedrooms and two baths is sited on a quiet Village Street uphill above the Woodstock Elementary School and across from the public playground at Vail Field and the Woodstock Country Club golf course. The home has benefitted from the thoughtful additions of an eat-in kitchen and a front porch where you can enjoy long summer evenings. A

    Laird Bradley Williamson Group Sothebys Intl. Realty

    25 Linden Hill St, Woodstock, VT 05091
  • /46

    $599,000

    • 3 Beds
    • 1.5 Baths
    • 1,344 Sq Ft

    1613 W Woodstock Rd, Woodstock, VT 05091

    WOODSTOCK-TURNKEY AND CONVENIENT! This totally renovated, move-in ready home located a few minutes to Woodstock Village, 20 minutes to Killington, 30 minutes to DHMC. Enjoy loads of recreational trails of all kinds, just minutes away.  Excellent spot with walking distance to the abutting Woodstock Union Middle School/High School. Newly Renovated inside and out. Spacious open concept living on

    Marni Rieger KW Vermont-Killington

    1613 W Woodstock Rd, Woodstock, VT 05091
  • /54

    $3,750,000

    • 3 Beds
    • 4.5 Baths
    • 3,865 Sq Ft

    249 Sawyer Rd, Woodstock, VT 05091

    This extraordinary residence offers breathtaking views of Billings Farm Preserve and the Green Mountains from nearly every corner, with Vermont's only national park directly in sight. The charming town of Woodstock, known for its boutiques and dining, is just a short walk away. Nestled at the end of a quiet road, the property offers unobstructed west-facing views for spectacular sunsets,

    Elevations Team Real Broker LLC

    249 Sawyer Rd, Woodstock, VT 05091
  • /32

    $899,500

    • 4 Beds
    • 3 Baths
    • 3,190 Sq Ft

    598 E Woodstock Rd, Woodstock, VT 05091

    This stately, rambling gambrel home offers privacy, convenience, antique charm, and room for everyone. Walking distance to the east end of Woodstock village, on 2.9 lush acres including a fenced backyard, a fenced vegetable garden, and extensive perennial beds. The home is a stunning mixture of antique touches and modern functionality, with beautiful built-ins and closet spaces at every turn. The

    Geoff Eckler Real Broker LLC

    598 E Woodstock Rd, Woodstock, VT 05091
  • /39

    $699,000

    • 3 Beds
    • 2.5 Baths
    • 1,958 Sq Ft

    5851 South Rd, Woodstock, VT 05071

    This charming home is an amazing opportunity to own a piece of history in the lovely village of South Woodstock , Vermont. Starting its life as the garage and home of Clyde Wood it has evolved over time with the present owners into a beautiful , meticulous residence. Much attention to detail can be found in every room from wide pine flooring to cathedral ceiling in the great room. The home is

    Carol Wood Williamson Group Sothebys Intl. Realty

    5851 South Rd, Woodstock, VT 05071
  • /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
  • /40

    $2,675,000

    • 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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