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Woodstock, VT Homes for Sale

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  • 26 Mount Peg Rd Unit B, Woodstock, VT 05091
    26 Mount Peg Rd Unit B, Woodstock, VT 05091
    26 Mount Peg Rd Unit B, Woodstock, VT 05091
    /31

    $995,000

    • 3 Beds
    • 3.5 Baths
    • 2,584 Sq Ft

    26 Mount Peg Rd Unit B, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit B, Woodstock, VT 05091
  • 26 Mount Peg Rd Unit C, Woodstock, VT 05091
    26 Mount Peg Rd Unit C, Woodstock, VT 05091
    26 Mount Peg Rd Unit C, Woodstock, VT 05091
    /28

    $995,000

    • 3 Beds
    • 3.5 Baths
    • 2,584 Sq Ft

    26 Mount Peg Rd Unit C, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit C, Woodstock, VT 05091
  • 1522 Barnard Rd, Woodstock, VT 05091
    1522 Barnard Rd, Woodstock, VT 05091
    1522 Barnard Rd, Woodstock, VT 05091
    /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
  • 26 Mount Peg Rd Unit D, Woodstock, VT 05091
    26 Mount Peg Rd Unit D, Woodstock, VT 05091
    26 Mount Peg Rd Unit D, Woodstock, VT 05091
    /31

    $1,195,000

    • 3 Beds
    • 3.5 Baths
    • 2,385 Sq Ft

    26 Mount Peg Rd Unit D, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit D, Woodstock, VT 05091
  • 39 Elm St Unit B, Woodstock, VT 05091
    39 Elm St Unit B, Woodstock, VT 05091
    39 Elm St Unit B, Woodstock, VT 05091
    /48

    $1,689,000

    • 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
  • 26 Mount Peg Rd Unit A, Woodstock, VT 05091
    26 Mount Peg Rd Unit A, Woodstock, VT 05091
    26 Mount Peg Rd Unit A, Woodstock, VT 05091
    /32

    $1,195,000

    • 3 Beds
    • 3.5 Baths
    • 2,592 Sq Ft

    26 Mount Peg Rd Unit A, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit A, Woodstock, VT 05091
  • 33 Mountain Ave, Woodstock, VT 05091
    33 Mountain Ave, Woodstock, VT 05091
    33 Mountain Ave, Woodstock, VT 05091
    /32

    $1,295,000

    • 2 Beds
    • 3.5 Baths
    • 2,280 Sq Ft

    33 Mountain Ave, Woodstock, VT 05091

    Welcome to 33 Mountain Avenue – a mid-century modern gem poised perfectly on the edge of Faulkner Park and at the foot of Mt. Tom and once part of the Marianne Faulkner Estate. The spacious one-level design provides a seamless connection between the indoor and outdoor living space which includes two ensuite bedrooms, living/dining room with fireplace, kitchen, family room, office and attached one

    Mary Mayhew Snyder Donegan Real Estate Group

    33 Mountain Ave, Woodstock, VT 05091
  • 115 Eastman Rd, Woodstock, VT 05091
    115 Eastman Rd, Woodstock, VT 05091
    115 Eastman Rd, Woodstock, VT 05091
    /47

    $8,000,000

    • 3 Beds
    • 3.5 Baths
    • 5,384 Sq Ft

    115 Eastman Rd, Woodstock, VT 05091

    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 Williamson Group Sothebys Intl. Realty

    115 Eastman Rd, Woodstock, VT 05091
  • 15 Central St, Woodstock, VT 05091
    15 Central St, Woodstock, VT 05091
    15 Central St, Woodstock, VT 05091
    /43

    $1,600,000

    • 4 Beds
    • 3 Baths
    • 6,014 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
  • 616 Rose Hill Rd, Woodstock, VT 05091
    616 Rose Hill Rd, Woodstock, VT 05091
    616 Rose Hill Rd, Woodstock, VT 05091
    /57

    $817,000

    • 3 Beds
    • 2 Baths
    • 2,760 Sq Ft

    616 Rose Hill Rd, Woodstock, VT 05091

    This is a rare opportunity to own 10.1 acres of land in a coveted area of Woodstock that includes a 1988 Frizzell Builders house and a detached oversized garage with a second floor for storage . The property was part of the King Farm which is now in Vt. Land Trust as conserved land , until it was split off in the late 1980's when the Colby family came into ownership and built the existing house

    Carol Wood Williamson Group Sothebys Intl. Realty

    616 Rose Hill Rd, Woodstock, VT 05091
  • 0 Barnard Rd Unit 20.002, Woodstock, VT 05091
    0 Barnard Rd Unit 20.002, Woodstock, VT 05091
    0 Barnard Rd Unit 20.002, Woodstock, VT 05091
    /11

    $779,000

    • Land
    • 6.46 Acres
    • $120,588 per Acre

    0 Barnard Rd Unit 20.002, Woodstock, VT 05091

    A truly unique 6 acre parcel of land conveniently located in the heart of Woodstock! Tremendous development potential! Zoning allows both COMMERCIAL and RESIDENTIAL use! The 6 acres visually divide into 2 components with 2 diverse personalities. The 1st component is an extraordinary private building lot in the heart of Woodstock! Access to this 4 acre component initially leads through a pleasant

    John Wetmore Wetmore Real Estate

    0 Barnard Rd Unit 20.002, Woodstock, VT 05091
  • 16 Church St, Woodstock, VT 05091
    16 Church St, Woodstock, VT 05091
    16 Church 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
  • 00 Carlton Hill Rd Unit 27, Woodstock, VT 05091
    00 Carlton Hill Rd Unit 27, Woodstock, VT 05091
    00 Carlton Hill Rd Unit 27, Woodstock, VT 05091
    /11

    $149,000

    • Land
    • 3.54 Acres
    • $42,090 per Acre

    00 Carlton Hill Rd Unit 27, Woodstock, VT 05091

    Discover the beauty of Vermont from this diverse 3.5-acre parcel along Carlton Hill Road, set in a peaceful rural location amid a neighborhood of substantial properties. With level access from a well-maintained town road, this land offers an inviting blend of convenience and natural charm. Just minutes from the vibrant shops, dining, and cultural attractions of Woodstock Village, the property

    Sandy Reavill Real Broker LLC

    00 Carlton Hill Rd Unit 27, Woodstock, VT 05091
  • 7 Slayton Terrace, Woodstock, VT 05091
    7 Slayton Terrace, Woodstock, VT 05091
    7 Slayton Terrace, Woodstock, VT 05091
    /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
  • 61 Academy Cir, Woodstock, VT 05071
    61 Academy Cir, Woodstock, VT 05071
    61 Academy Cir, 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
  • 958 E Woodstock Rd, Woodstock, VT 05091
    958 E Woodstock Rd, Woodstock, VT 05091
    958 E Woodstock Rd, Woodstock, VT 05091
    /50

    $1,100,000

    • 3 Beds
    • 2.5 Baths
    • 2,220 Sq Ft

    958 E Woodstock Rd, Woodstock, VT 05091

    Just minutes from the heart of Woodstock, this 3-bedroom, 3-bath home with a dedicated office/family room has been transformed from the ground up into a modern, energy-efficient retreat. Taken down to the studs, the renovation was comprehensive—every system replaced, with all new wiring, plumbing, insulation, and mechanicals, along with a new roof, Pella windows, central heating, and air

    Keri Cole Williamson Group Sothebys Intl. Realty

    958 E Woodstock Rd, Woodstock, VT 05091
  • 1514 South Rd, Woodstock, VT 05091
    1514 South Rd, Woodstock, VT 05091
    1514 South Rd, Woodstock, VT 05091
    /43

    $595,000

    • 3 Beds
    • 2 Baths
    • 1,920 Sq Ft

    1514 South Rd, Woodstock, VT 05091

    This tidy, well maintained Mid-Century Ranch home is conveniently located just 1.5 miles from the Village Green. Perched on a sunny knoll with a southern valley view, this well maintained home features open concept kitchen/dining, a large, bright living room, three bedrooms all with oak floors, a walk out basement providing opportunity for guest accommodation, or a hobby/play room. The 2 car

    Danny Kogut Williamson Group Sothebys Intl. Realty

    1514 South Rd, Woodstock, VT 05091
  • 442 E Woodstock Rd Unit 4A, Woodstock, VT 05091
    442 E Woodstock Rd Unit 4A, Woodstock, VT 05091
    442 E Woodstock Rd Unit 4A, Woodstock, VT 05091
    /6

    $239,000

    • 2 Beds
    • 1 Bath
    • 1,190 Sq Ft

    442 E Woodstock Rd Unit 4A, Woodstock, VT 05091

    Airy, tranquil and quiet, this former yoga studio space has been converted into a two bedroom condo. Sweeping views through the Palladian window, large living area with soaring vaulted ceiling, newer kitchen with granite counters and newer bath with walk in shower. Spacious entry can accommodate bikes, skis and more. Walking distance to shops, restaurants, entertainment and recreation in the

    Jane Darrach Martha E. Diebold/Hanover

    442 E Woodstock Rd Unit 4A, Woodstock, VT 05091
  • 403 Horse Shoe Way, Woodstock, VT 05071
    403 Horse Shoe Way, Woodstock, VT 05071
    403 Horse Shoe Way, Woodstock, VT 05071
    /37

    $845,000

    • 2 Beds
    • 1.5 Baths
    • 1,714 Sq Ft

    403 Horse Shoe Way, Woodstock, VT 05071

    Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials.The home was carefully, and

    Danny Kogut Williamson Group Sothebys Intl. Realty

    403 Horse Shoe Way, Woodstock, VT 05071
  • 1362 Barnard Rd, Woodstock, VT 05091
    1362 Barnard Rd, Woodstock, VT 05091
    1362 Barnard Rd, Woodstock, VT 05091
    /60

    $2,395,000

    • 4 Beds
    • 2 Baths
    • 3,000 Sq Ft

    1362 Barnard Rd, Woodstock, VT 05091

    Gilbert’s Hill: The birthplace of American skiing and one of Vermont's most celebrated properties for its contribution to the ski industry. Spanning 112.88± acres in Woodstock (79.31 acres) and Pomfret (33.57 acres), the farm is recognized as the birthplace of lift-served skiing in America, where the first rope tow was installed in 1934. Today, its open pastures, rolling terrain, and historic ski

    Chris Lang

    1362 Barnard Rd, Woodstock, VT 05091
  • 509 Church Hill Rd, Wood Stock, VT 05091
    509 Church Hill Rd, Wood Stock, VT 05091
    509 Church Hill Rd, Wood Stock, VT 05091
    /55

    $915,000

    • 3 Beds
    • 3 Baths
    • 2,150 Sq Ft

    509 Church Hill Rd, Wood Stock, VT 05091

    Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens.The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes ,

    Carol Wood Williamson Group Sothebys Intl. Realty

    509 Church Hill Rd, Wood Stock, VT 05091
  • 3364 W Woodstock Rd, Woodstock, VT 05091
    3364 W Woodstock Rd, Woodstock, VT 05091
    3364 W Woodstock Rd, Woodstock, VT 05091
    /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
  • 0 South Rd, Woodstock, VT 05071
    0 South Rd, Woodstock, VT 05071
    0 South Rd, Woodstock, VT 05071
    /24

    $646,500

    • Land
    • 37.85 Acres
    • $17,081 per Acre

    0 South Rd, Woodstock, VT 05071

    Country land at the south end of Woodstock reaching from RT 106 to the top of the ridge. Potential for views with clearing at several levels. Trails through the property with access to the GMHA network. Stonewalls and a stream.About two miles to GMHA and South Woodstock village, one mile to VAST trail.40 minutes to skiing at Killington, less to Okemos. Seven miles into Woodstock Village.

    Matthew Spittle Vermont Horse Country Real Estate

    0 South Rd, Woodstock, VT 05071
  • 513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091
    513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091
    513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091
    /42

    $1,250,000

    • 4 Beds
    • 2.5 Baths
    • 2,668 Sq Ft

    513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091

    This traditional New England Colonial, designed and custom built by Vermont Vernacular Builders, is sited to capture idyllic all-around mountain views and southern light. The spacious four-bedroom home features wide board floors, exposed beams, and a sun-filled chef’s kitchen and den. New Thor stainless steel 48" propane range installed October 2025.Privately set on over 8 acres, the property

    Chris Crowe Quechee Lakes Real Estate Center

    513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091
  • 37 South St, Woodstock, VT 05091
    37 South St, Woodstock, VT 05091
    37 South St, Woodstock, VT 05091
    /49

    $785,000

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

    37 South St, Woodstock, VT 05091

    New price! Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to playgrounds, ball

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    37 South St, Woodstock, VT 05091
  • 1054 W Woodstock Rd, Woodstock, VT 05091
    1054 W Woodstock Rd, Woodstock, VT 05091
    1054 W Woodstock 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
  • 3914 South Rd, Woodstock, VT 05091
    3914 South Rd, Woodstock, VT 05091
    3914 South Rd, Woodstock, VT 05091
    /40

    $725,000

    • 4 Beds
    • 3 Baths
    • 3,584 Sq Ft

    3914 South Rd, Woodstock, VT 05091

    This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont’s changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level.

    Laird Bradley Williamson Group Sothebys Intl. Realty

    3914 South Rd, Woodstock, VT 05091
  • 00 Long Hill Rd, Woodstock, VT 05071
    00 Long Hill Rd, Woodstock, VT 05071
    00 Long Hill Rd, Woodstock, VT 05071
    /58

    $549,000

    • Land
    • 20.2 Acres
    • $27,178 per Acre

    00 Long Hill Rd, Woodstock, VT 05071

    Discover the perfect blend of privacy and convenience with this exceptional 20.2-acre parcel, combining two lots into one remarkable opportunity. Featuring a 50 foot right-of-way for access, this wooded retreat offers multiple prime building sites. With selective clearing, you can take in breathtaking views in your choice of direction; east, south, north, or west.Located just minutes from

    Eric Johnston Four Seasons Sotheby's Int'l Realty

    00 Long Hill Rd, Woodstock, VT 05071
  • 1079 Fletcher Hill Rd, Woodstock, VT 05071
    1079 Fletcher Hill Rd, Woodstock, VT 05071
    1079 Fletcher Hill Rd, Woodstock, VT 05071
    /42

    $425,000

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    1079 Fletcher Hill Rd, Woodstock, VT 05071

    This charming 2-bedroom ranch house offers a nice layout for main floor living. Features include a sunroom entrance, two bedrooms, a full bath, laundry room, and a main living/dining area with a kitchen, all within a rural setting with ample natural light, local views, and a deck. Recent updates include a primary bedroom ensuite featuring a custom walk-in shower and double sinks, new flooring, a

    Terry Davis Williamson Group Sothebys Intl. Realty

    1079 Fletcher Hill Rd, Woodstock, VT 05071
  • 18 The Green, Woodstock, VT 05091
    18 The Green, Woodstock, VT 05091
    18 The Green, Woodstock, VT 05091
    /42

    $3,500,000

    • 6 Beds
    • 8 Baths
    • 5,142 Sq Ft

    18 The Green, Woodstock, VT 05091

    Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town’s finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort

    Danny Kogut Williamson Group Sothebys Intl. Realty

    18 The Green, Woodstock, VT 05091
  • 2706 E Woodstock Rd, Woodstock, VT 05091
    2706 E Woodstock Rd, Woodstock, VT 05091
    2706 E Woodstock Rd, Woodstock, VT 05091
    /60

    $1,750,000

    • 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, café, or retail store), Post Office (with current

    John Bassette Bassette Real Estate Group

    2706 E Woodstock Rd, Woodstock, VT 05091
  • 41 Pleasant St, Woodstock, VT 05091
    41 Pleasant St, Woodstock, VT 05091
    41 Pleasant St, Woodstock, VT 05091
    /54

    $2,599,000

    • 9 Beds
    • 11 Baths
    • 5,993 Sq Ft

    41 Pleasant St, Woodstock, VT 05091

    This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with

    Jennifer Falvey KW Vermont Woodstock

    41 Pleasant St, Woodstock, VT 05091
  • 0 Noah Wood Rd, Woodstock, VT 05071
    0 Noah Wood Rd, Woodstock, VT 05071
    0 Noah Wood Rd, Woodstock, VT 05071
    /19

    $695,000

    • Land
    • 60.57 Acres
    • $11,474 per Acre

    0 Noah Wood Rd, Woodstock, VT 05071

    Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower

    Dan Noble Snyder Donegan Real Estate Group

    0 Noah Wood Rd, Woodstock, VT 05071
  • 185 Riverbend Way, Woodstock, VT 05091
    185 Riverbend Way, Woodstock, VT 05091
    185 Riverbend Way, Woodstock, VT 05091
    /32

    $72,999

    • 3 Beds
    • 2 Baths
    • 1,008 Sq Ft

    185 Riverbend Way, Woodstock, VT 05091

    Start your Vermont dream with this affordable 3-bedroom, 2-bath mobile home just minutes from downtown Woodstock, VT. Located in a quiet, private community with stunning mountain views and direct river frontage on the Ottauquechee, this home is a rare opportunity to enjoy scenic living at a budget-friendly price. Perfect as a first home, vacation getaway, or investment, this property is also

    Mendi Michael Engel & Völkers Okemo

    185 Riverbend Way, Woodstock, VT 05091
  • 34 Midsomer Meadows Ln, Woodstock, VT 05091
    34 Midsomer Meadows Ln, Woodstock, VT 05091
    34 Midsomer Meadows Ln, Woodstock, VT 05091
    /60

    $950,000

    • 3 Beds
    • 3 Baths
    • 2,794 Sq Ft

    34 Midsomer Meadows Ln, Woodstock, VT 05091

    Welcome to Starry Hill, a fully furnished Airbnb rental, handcrafted, solid-timber Colonial privately nestled on 18.9 tranquil acres just 5 miles North of Woodstock, built over 4 years by a family of loggers and master craftsmen. This exceptional home features Eastern white pine walls, hemlock structural beams, and pine ceilings/flooring sourced from the property. Warm, inviting living spaces

    John Bassette Bassette Real Estate Group

    34 Midsomer Meadows Ln, Woodstock, VT 05091
  • 598 E Woodstock Rd, Woodstock, VT 05091
    598 E Woodstock Rd, Woodstock, VT 05091
    598 E Woodstock Rd, Woodstock, VT 05091
    /48

    $795,000

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

    598 E Woodstock Rd, Woodstock, VT 05091

    Discover the charm of historic Woodstock, Vermont in this spacious, light-filled home just minutes from the village green. Blending timeless New England character with modern comfort, this property offers an abundance of space and versatility — ideal as a full-time residence or a relaxing ski-season getaway.This inviting home features hardwood floors, custom cherry built-ins, and two fireplaces,

    Erika Smith RE/MAX Upper Valley

    598 E Woodstock Rd, Woodstock, VT 05091
  • 355 Greene Rd, Woodstock, VT 05071
    355 Greene Rd, Woodstock, VT 05071
    355 Greene Rd, Woodstock, VT 05071
    /59

    $18,000,000

    • 7 Beds
    • 10 Baths
    • 12,520 Sq Ft

    355 Greene Rd, Woodstock, VT 05071

    Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and

    Chris Lang

    355 Greene Rd, Woodstock, VT 05071
  • 249 Sawyer Rd, Woodstock, VT 05091
    249 Sawyer Rd, Woodstock, VT 05091
    249 Sawyer Rd, Woodstock, VT 05091
    /24

    $3,300,000

    • 3 Beds
    • 4.5 Baths
    • 3,682 Sq Ft

    249 Sawyer Rd, Woodstock, VT 05091

    Tucked away just minutes from the shops, cafes, and restaurants of Woodstock Village, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, family gatherings, and endless outdoor recreation opportunities nearby. The 3-bedroom primary residence is perfectly sited to overlook Woodstock’s iconic Mount Tom and the Marsh-Billings Musuem, Vermont’s only National

    Andrew Bustin LandVest, Inc/Woodstock

    249 Sawyer Rd, Woodstock, VT 05091
  • 42 Heritage Condo Way Unit 14D, Woodstock, VT 05091
    42 Heritage Condo Way Unit 14D, Woodstock, VT 05091
    42 Heritage Condo Way Unit 14D, Woodstock, VT 05091
    /60

    $230,000

    • 1 Bed
    • 1 Bath
    • 856 Sq Ft

    42 Heritage Condo Way Unit 14D, Woodstock, VT 05091

    Welcome to your Woodstock affordable retreat! This inviting, end-unit, two-level townhouse in the sought-after Heritage Condominium community is nestled on a dead-end road just minutes west of the historic village of Woodstock. This bright 856 sq/ft two-level home offers an open-concept first floor with a carpeted living/dining area warmed by Empire gas heat (plus electric backup). From this

    John Bassette Bassette Real Estate Group

    42 Heritage Condo Way Unit 14D, Woodstock, VT 05091
  • 1 Carlton Hill Rd, Woodstock, VT 05091
    1 Carlton Hill Rd, Woodstock, VT 05091
    1 Carlton Hill Rd, Woodstock, VT 05091
    /7

    $325,000

    • Land
    • 8 Acres
    • $40,625 per Acre

    1 Carlton Hill Rd, Woodstock, VT 05091

    Sweet Spot - 8 acre building lot located within minutes of the Woodstock Village Green! Driveway is in place and a lovely building site has been cleared and power is at site. Wonderful opportunity to build your Vermont getaway or primary residence. Enjoy access to four season recreation, Marsh-Billings-Rockefeller National Park, theatre, arts, dining, shopping and a short commute to all

    Mary Mayhew Snyder Donegan Real Estate Group

    1 Carlton Hill Rd, Woodstock, VT 05091

Showing Results 1 - 40, Page 1 of 2

Vermont Windsor County Woodstock

Real Estate & Homes for Sale in Woodstock, VT

Why Live in Woodstock

The town of Woodstock helps New England earn its reputation for quaint small towns. “Woodstock gets written up all the time as one of the prettiest small towns in America. It’s a Norman Rockwell-style town filled with charm,” says Gretchjen Smith, ...

Learn more about living in Woodstock

Frequently Asked Questions

What is the average home price in Woodstock, VT?
Homes for sale in Woodstock, VT have an average home price of $1,539,378.
Are home prices dropping in Woodstock?
Yes, home prices in Woodstock are down 4% in the last 12 months.
How many homes have sold over the last 12 months in Woodstock, VT?
66 homes have sold in Woodstock, VT over the last 12 months.
What are the most popular zip codes in Woodstock, VT?
The most popular zip codes in Woodstock, VT include 05091, 05067, 05001, 05071 and 05048.
How much do you need to make to afford a house in Woodstock?
The median home price in Woodstock is $995,000. If you put a 20% down payment of $199,000 and had a 30-year fixed mortgage with an interest rate of 6.18%, your estimated principal and interest payment would be $4,860 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $208K a year to afford the median home price in Woodstock. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Woodstock, VT?
Woodstock, VT has highly rated public and private schools. Some of the best schools in Woodstock based on Niche Grades are Woodstock Senior Uhsd #4, Woodstock Elementary School and Woodstock Union High School. Browse all the schools in Woodstock, VT to learn more.

Home Trends in Woodstock, VT

On average, homes in Woodstock, VT sell after 87 days on the market compared to the national average of 53 days. The median sale price for homes in Woodstock, VT over the last 12 months is $836,500, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$836,500
Median Single Family Sale Price
$1,100,000
Median Townhouse Sale Price
$499,000
Median 2 Bedroom Sale Price
$481,250
Median 1 Bedroom Sale Price
$230,000
Average Price Per Sq Ft
$492
Number of Homes for Sale
36
Last 12 months Home Sales
66
Months of Supply
6.50
Median List Price
$995,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-4%
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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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