1,876

Woodstock Town, VT Homes

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  • /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
  • /18

    $2,550 per month

    Brand New Duplex Properties For Rent In Wo...

    3 Beds

    2247 E Woodstock Rd, Woodstock, VT 05091

    Be the very first people to live in these brand new homes. Two amazing Duplex properties will be ready for new tenants between late June and early July. Both two bedroom and three bedroom configurations are available. Enjoy the perfect combination of location and comfort. Nestled on the banks of the Ottauquechee River you can enjoy the charm and quiet of Vermont living in these brand new

    2247 E Woodstock Rd, Woodstock, VT 05091
  • /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
    • /40

      Est $1,308,316 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
  • /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
  • /50

    $1,275,000 Sold Apr 02, 2025

    • 2,584 Sq Ft
    • $493/SF
    • 72 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1985

    1075 Westerdale Rd, Woodstock, VT 05091

    This lovingly maintained property with mountain views has been enjoyed by a single family since its construction in 1985. The open-concept layout is anchored by a stone Rumford fireplace, which along with the southern exposure warms the large easy-to-keep space. The first floor master boasts ample storage with a sliding door for quick access to the grounds. Across from the main house via a

    Keri Cole Williamson Group Sothebys Intl. Realty

    1075 Westerdale Rd, Woodstock, VT 05091
    • /39

      Est $953,432 Not Listed For Sale

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

      433 Cowdrey Path, Woodstock, VT 05091

      433 Cowdrey Path, 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
  • /35

    $475,000 Sold Mar 27, 2025

    • 1,424 Sq Ft
    • $334/SF
    • 144 Days On Market
    • 4 Beds
    • 1 Bath
    • Built 1971

    378 Fletcher Hill Rd, South Woodstock, VT 05071

    Privately located, in desirable South Woodstock! A comfortable home with the benefit of great outside spaces providing the opportunity for recreation, gardening or entertaining! South Woodstock is well known for the potential of having wonderful access to miles of trails enjoyed by equestrians, hikers and snowmobilers. The numerous amenities of historic Woodstock Village are just minutes away!

    John Wetmore Wetmore Real Estate

    378 Fletcher Hill Rd, South Woodstock, VT 05071
    • /23

      Not Listed For Sale

      0 Carlton Hill Rd Unit 4670150, Woodstock, VT 05091

      0 Carlton Hill Rd Unit 4670150, 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
  • /24

    $230,000 Sold Mar 26, 2025

    • 856 Sq Ft
    • $269/SF
    • 3 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1984

    29 Heritage Condos Unit 29D, Woodstock, VT 05091

    OPEN HOUSE CANCELLED.A desirable 1 bedroom condo in Woodstock! Just a short distance from the high school, Farmer's Market, and Thompson Senior Center and only a 3 minute drive from the Woodstock town green and less than 12 minutes to Saskadena Six for skiing. The condo association takes care of all the exterior maintenance (minus clearing off the balcony), and provides interior lockable

    Franchesca Collins Hall Collins Real Estate Group

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

      Est $866,932 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,956 Sq Ft

      3369 Hartland Hill Rd, Woodstock, VT 05091

      3369 Hartland Hill Rd, Woodstock, VT 05091
  • /41

    $1,150,000 Pending

    • 5 Beds
    • 4.5 Baths
    • 4,698 Sq Ft

    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
  • /43

    $700,000 Sold Feb 14, 2025

    • 2,616 Sq Ft
    • $268/SF
    • 15 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1988

    944 College Hill Rd, Woodstock, VT 05091

    PRIVATE- Cape Cod Home less than a mile to Historic Woodstock Village! This generous sized home consisting of 2616 squ ft. sits on 3.62 secluded acres. Built in 1988 and first time on the market- this home has been well maintained with an abundance of light, generous proportioned rooms with handsome hardwood floors. First floor consists of kitchen with quartz counters and soft neutral toned

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    944 College Hill Rd, Woodstock, VT 05091
    • /40

      Est $825,609 Not Listed For Sale

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

      3090 South Rd, Woodstock, VT 05091

      3090 South Rd, Woodstock, VT 05091
  • /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
  • /40

    $2,750,000 Sold Feb 13, 2025

    • 6,443 Sq Ft
    • $427/SF
    • 495 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1970

    318 Ebbin Lockwood Way, Woodstock, VT 05071

    Serene, private, contemporary: Sited on a ridge above South Woodstock village, the 54 acre property offers complete seclusion in an elegant setting with an extensive network of trails. The three bedroom main dwelling is sleek and elegant, with an open floor plan crafted to take in the beauty of the site with abundant use of organic material designed to integrate the design with the surrounding

    Story Jenks LandVest, Inc/Woodstock

    318 Ebbin Lockwood Way, Woodstock, VT 05071
    • /37

      Est $1,245,549 Not Listed For Sale

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

      326 Hall Cir, Woodstock, VT 05091

      326 Hall Cir, Woodstock, VT 05091
  • /36

    $1,800,000 Under Contract

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

    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
  • /2

    $1,175,000 Sold Jan 29, 2025

    • 2,660 Sq Ft
    • $442/SF
    • 186 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2014

    6453 South Rd, Woodstock, VT 05071

    Round Top Cottage is sited on a knoll just outside the village of South Woodstock on 20 acres, offering complete privacy and views of the rolling hills framing the Kedron Valley. This three-bedroom lodge, fully renovated in 2024, blends modern amenities with rustic elegance. The open floor plan features cathedral ceilings in the main living and dining area, creating an inviting space to gather

    Story Jenks LandVest, Inc/Woodstock

    6453 South Rd, Woodstock, VT 05071
    • /30

      Est $1,236,333 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
  • /28

    $495,000

    • 2 Beds
    • 3 Baths
    • 2,091 Sq Ft

    85 Townhouse Way Unit 14, Woodstock, VT 05091

    Fully furnished condo nestled in a small quiet community just 5 minutes from historic Woodstock. Super location! This unit is in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    85 Townhouse Way Unit 14, Woodstock, VT 05091
  • /40

    $4,205,000 Sold Jan 27, 2025

    • 5,939 Sq Ft
    • $708/SF
    • 121 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1797

    327 Fletcher Schoolhouse Rd, Woodstock, VT 05071

    ByBrook Farm: Reimagined, turnkey 1790s farmhouse set in one of Vermont's most loved valleys, perennial gardens, stone walls, a spring fed pond, a brook, and rolling meadows. Quiet luxury. Just outside the hamlet of South Woodstock on 25 acres, the 2-bedroom 4,667 sf farmhouse and the 2-bedroom 1,273 sf guest cottage are connected by a stone pathway through the gardens. In the recent renovations

    Story Jenks LandVest, Inc/Woodstock

    327 Fletcher Schoolhouse Rd, Woodstock, VT 05071
    • /40

      Est $1,205,309 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
  • /3

    $329,900

    • Land
    • 142 Acres
    • $2,323 per Acre

    00 Chateauguay Rd, Woodstock, VT 05091

    Prime land access off Chateauguay Rd with no zoning, HOA, or deed restrictions. Sub-dividable with well and septic needed; electricity nearby. Just 25 minutes from the town of Woodstock’s amenities, parks and historic sites. 20 minutes to Killington Ski Resort and Coolidge State Park, and 30 minutes to Pico Mountain Ski Resort and Lynches River County Park. Perfect for building your dream home or

    Derek Greene Derek Greene

    00 Chateauguay Rd, Woodstock, VT 05091
  • /37

    $975,000 Sold Jan 10, 2025

    • 2,944 Sq Ft
    • $331/SF
    • 28 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1994

    828 Deerbrook Way, Woodstock, VT 05091

    A gem of a property on 12 spectacular, mostly wooded, acres in the desirable Deerbrook Way area of Woodstock. Four+ miles to all the amenities of Woodstock Village and 8 miles to the Skyship Gondola at Killington. Built in 1994, this custom designed red oak Post and Beam Contemporary provides everything you would want in a primary residence or a get away vacation retreat. Situated on a 12+ acre

    Stan Butler Four Seasons Sotheby's Int'l Realty

    828 Deerbrook Way, Woodstock, VT 05091
    • /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
  • /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 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 vaulted

    Derek Cosentino Four Seasons Sotheby's Int'l Realty

    339 Gully Rd, Woodstock, VT 05091
  • /60

    $1,499,000 Sold Jan 06, 2025

    • 3,001 Sq Ft
    • $500/SF
    • 181 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1985

    1133 Atwood Ln, Woodstock, VT 05091

    **Price Improvement**Beautiful country contemporary home offers the best of Vermont living.Private yet convenient,just 6 miles from Woodstock Village and within 30 min. drive to DHMC,Dartmouth College,& Upper Valley shopping, dining, arts and amenities.Set on 28.6 acres,the property feels like a private sanctuary w/ stunning views and southern exposure.Inside,warm wood floors & finishes flow

    Tambrey Vutech KW Vermont Woodstock

    1133 Atwood Ln, Woodstock, VT 05091
    • /40

      Est $1,472,827 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
  • /26

    $650,000

    • Land
    • 78 Acres
    • $8,366 per Acre

    0 Mecawee Rd, Woodstock, VT 05091

    Spectacular 77+ acre parcel on sought after Mecawee Rd. with a perfect combination of level, sloping and hilly terrain. There are multiple building sites including a large cleared area set back off the road with a driveway in place and utilities (electric & fiber optic) at the street. This past Fall, the Sellers went to great lengths to clear the land all the way down to the road opening up

    Dan Noble Snyder Donegan Real Estate Group

    0 Mecawee Rd, Woodstock, VT 05091
  • /32

    $692,000 Sold Dec 19, 2024

    • 2,527 Sq Ft
    • $274/SF
    • 195 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 1890

    1207 Church Hill Rd, Woodstock, VT 05091

    Historic Vermont cape house with easy access, only a mile to the Woodstock village center. There is a lot of history and character with beautiful old wood floors and beams. A covered walkway from the attached two-car garage comes into a mud-entry room and right into the classic farmhouse kitchen. Off the kitchen is a generous pantry/laundry room and a bath with shower. The spacious family

    John Snyder Snyder Donegan Real Estate Group

    1207 Church Hill Rd, Woodstock, VT 05091
    • /32

      Est $542,998 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
  • /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
  • /44

    $470,000 Sold Dec 17, 2024

    • 1,536 Sq Ft
    • $306/SF
    • 31 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1971

    2115 E Woodstock Rd, Woodstock, VT 05091

    This charming Woodstock home, with river views & versatile floor plan offers two levels of thoughtfully designed living space. This property is a fantastic opportunity for a short-term rental investment or the perfect family getaway for ski season! Upon entering, you’ll immediately notice the attractive wood finishes & natural light, capturing the beauty of the surroundings. The home has 3

    Isabella Luhrs BHG Masiello Keene

    2115 E Woodstock Rd, Woodstock, VT 05091
    • /34

      Est $586,530 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,300 Sq Ft

      1782 South Rd, Woodstock, VT 05091

      1782 South Rd, Woodstock, VT 05091
  • /9

    $275,000

    • Land
    • 0.43 Acre
    • $639,535 per Acre

    1054 W Woodstock Rd, Woodstock, VT 05091

    Ideally located parcel across West Woodstock Road from the Woodstock Farmers Market and 500 yards from the entry to Woodstock Union Middle & High School. Public water and sewer available with access off Prosper Road near the junction of US Road Route 4/West Woodstock Road. Building plans available. Multi-unit housing development potential in zero vacancy environment.

    Laird Bradley Williamson Group Sothebys Intl. Realty

    1054 W Woodstock Rd, Woodstock, VT 05091
  • /2

    $2,850,000 Sold Dec 16, 2024

    • 6,403 Sq Ft
    • $445/SF
    • 158 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1976

    2055 Church Hill Rd, Woodstock, VT 05091

    Nestled among verdant rolling hills, High Birch is located in one of the area’s most desirable regions at the midpoint between Woodstock and South Woodstock Villages. Designed in 1976 by prominent New York architect Lewis Davis, of Davis, Brody and Bond renowned for his modernist skyscrapers that impacted the skyline of New York City, the home contrasts sleek interior spaces to the surrounding

    Danny Kogut Williamson Group Sothebys Intl. Realty

    2055 Church Hill Rd, Woodstock, VT 05091
    • /38

      Est $1,523,383 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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