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Woodstock, VT Homes for Sale

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  • 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
  • 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
  • 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
    /34

    $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
    /31

    $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
  • 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
    /34

    $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
  • 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
    /35

    $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

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit A, 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
  • 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
    /40

    $1,295,000

    • 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
  • 17 Linden Hill, Wood Stock, VT 05091
    17 Linden Hill, Wood Stock, VT 05091
    17 Linden Hill, Wood Stock, VT 05091
    /35

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 2,736 Sq Ft

    17 Linden Hill, Wood Stock, VT 05091

    Open House! Saturday Oct 18 from 10-12. Once known as the Sunshine Nursery School, this home's history expands back to ~1870 and now it stands as a spacious and beautifully updated residence with an expansive terraced yard (one of the largest near the village) and elegant interiors. High ceilings, high-quality wood floors, and sun-filled rooms define the main level, where a gracious primary

    Holly Hall Hall Collins Real Estate Group

    17 Linden Hill, Wood Stock, VT 05091
  • 958 E Woodstock Rd, Woodstock, VT 05091
    958 E Woodstock Rd, Woodstock, VT 05091
    958 E Woodstock Rd, Woodstock, VT 05091
    /57

    $1,150,000

    • 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
  • 2394 Fletcher Hill Rd, Woodstock, VT 05091
    2394 Fletcher Hill Rd, Woodstock, VT 05091
    2394 Fletcher Hill Rd, Woodstock, VT 05091
    /33

    $1,900,000

    • 2 Beds
    • 2.5 Baths
    • 2,944 Sq Ft

    2394 Fletcher Hill Rd, Woodstock, VT 05091

    Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is

    John Snyder Snyder Donegan Real Estate Group

    2394 Fletcher Hill Rd, 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
  • 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
  • 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
  • 851 Riverside Park Rd, Woodstock, VT 05091
    851 Riverside Park Rd, Woodstock, VT 05091
    851 Riverside Park Rd, Woodstock, VT 05091
    /60

    $1,995,000

    • 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
  • 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

    Embrace the beauty of Vermont with this diverse 3.5-acre parcel of land, perfectly positioned in a desirable neighborhood of substantial homes. Offering level access from a well-maintained town road, this property provides a wonderful opportunity for building your dream residence.Nestled in a peaceful rural setting, this lot is just minutes from the charming amenities of Woodstock Village. Enjoy

    Sandy Reavill Real Broker LLC

    00 Carlton Hill Rd Unit 27, Woodstock, VT 05091
  • 2 Highland Ave, Woodstock, VT 05091
    2 Highland Ave, Woodstock, VT 05091
    2 Highland Ave, Woodstock, VT 05091
    /8

    $650,000

    • Land
    • 2.41 Acres
    • $269,710 per Acre

    2 Highland Ave, Woodstock, VT 05091

    An extraordinary opportunity to acquire a private building parcel overlooking the Marsh Billings Rockefeller National Park, Billing's Farm to the Connecticut River Valley in Woodstock Village. The secluded, elevated parcel combines an early homesite and a productive hayfield mowed by a family member within living memory. The access is level and intersects Highland Avenue with an extended line of

    Laird Bradley Williamson Group Sothebys Intl. Realty

    2 Highland Ave, 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
  • 355 Greene Rd, Woodstock, VT 05071
    355 Greene Rd, Woodstock, VT 05071
    355 Greene Rd, Woodstock, VT 05071
    /60

    $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
  • 1362 Barnard Rd, Woodstock, VT 05091
    1362 Barnard Rd, Woodstock, VT 05091
    1362 Barnard Rd, Woodstock, VT 05091
    /60

    $2,600,000

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

    1362 Barnard Rd, Woodstock, VT 05091

    Gilbert’s Hill is one of Vermont’s most celebrated properties and a national landmark for its contribution to the sport of alpine skiing. 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
  • 42 Heritage Condo Way Unit 22, Woodstock, VT 05091
    42 Heritage Condo Way Unit 22, Woodstock, VT 05091
    42 Heritage Condo Way Unit 22, Woodstock, VT 05091
    /23

    $242,500

    • 1 Bed
    • 1 Bath
    • 816 Sq Ft

    42 Heritage Condo Way Unit 22, Woodstock, VT 05091

    Bright and efficient 1-bedroom ground-level condo in the sought-after Heritage Way association, just one mile from Woodstock Village. This move-in-ready coveted end unit offers comfort, privacy, and numerous recent updates.Features include a new Rinnai furnace (2023), new Anderson sliding glass door and bedroom windows (2024), drop ceiling with added sound insulation, and full-size washer

    Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

    42 Heritage Condo Way Unit 22, Woodstock, VT 05091
  • 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
  • 5798 W Woodstock Rd, Woodstock, VT 05091
    5798 W Woodstock Rd, Woodstock, VT 05091
    5798 W Woodstock Rd, Woodstock, VT 05091
    /45

    $439,000

    • 4 Beds
    • 2 Baths
    • 1,617 Sq Ft

    5798 W Woodstock Rd, Woodstock, VT 05091

    Charming 4 bedroom farmhouse with attached barn/garage with lots of overhead storage is located across the road from the scenic Ottauquechee River. Minutes from Woodstock Village Green with all of its amenities and a short distance from Killington with its world renown Ski Resort. Year round activities abound ! The house has a sunny eat in kitchen, spacious dining room and a living room

    Carol Wood Williamson Group Sothebys Intl. Realty

    5798 W Woodstock Rd, 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
  • 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
  • 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
  • 3961 Hartland Hill Rd, Woodstock, VT 05091
    3961 Hartland Hill Rd, Woodstock, VT 05091
    3961 Hartland Hill Rd, Woodstock, VT 05091
    /60

    $869,000

    • 5 Beds
    • 5 Baths
    • 3,886 Sq Ft

    3961 Hartland Hill Rd, Woodstock, VT 05091

    This lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting less than a mile to village shopping, schools, dining and recreation. Updated with modern finishes to enhance accessibility and one level living-while maintaining the warm, country charm. First floor features a

    Tambrey Vutech KW Vermont Woodstock

    3961 Hartland Hill Rd, Woodstock, VT 05091
  • 35 Mountain Ave, Woodstock, VT 05091
    35 Mountain Ave, Woodstock, VT 05091
    35 Mountain Ave, Woodstock, VT 05091
    /33

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 1,555 Sq Ft

    35 Mountain Ave, Woodstock, VT 05091

    Prime In-Village location on Mountain Avenue just steps to Faulkner Park, The Mt Tom trail system and Woodstock Rec Center. This classic New England duplex (eastern side) home serves perfectly as a full time residence, or an easy keep as a second home. Through a classic covered porch enter the foyer with gleaming hardwood floors and high ceilings. The spacious living room has a propane stove, and

    Danny Kogut Williamson Group Sothebys Intl. Realty

    35 Mountain Ave, Woodstock, 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
  • 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
  • 1782 Randall Rd, Woodstock, VT 05091
    1782 Randall Rd, Woodstock, VT 05091
    1782 Randall Rd, Woodstock, VT 05091
    /37

    $985,000

    • 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
  • 185 Riverbend Way, Woodstock, VT 05091
    185 Riverbend Way, Woodstock, VT 05091
    185 Riverbend Way, Woodstock, VT 05091
    /32

    $74,900

    • 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
  • 37 Atwood Ave, Woodstock, VT 05091
    37 Atwood Ave, Woodstock, VT 05091
    37 Atwood Ave, Woodstock, VT 05091
    /30

    $449,500

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    37 Atwood Ave, Woodstock, VT 05091

    Charming, updated, and perfectly located—this turnkey gem is your ticket to easy living in one of the area’s most adorable neighborhoods! With all the major systems recently upgraded - including a new furnace, hot water heater, Tesla Powerwall, and water purification system - this efficient home is move-in ready.Inside, you’ll love the fresh renovations: a modern kitchen with

    Keri Cole Williamson Group Sothebys Intl. Realty

    37 Atwood Ave, 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
  • 72 Oakridge Way, Woodstock, VT 05091
    72 Oakridge Way, Woodstock, VT 05091
    72 Oakridge Way, Woodstock, VT 05091
    /54

    $985,000

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

    72 Oakridge Way, Woodstock, VT 05091

    PRIME LOCATION! Tucked away at the end of a peaceful dead-end road in the Westerdale neighborhood is this Vermont Cape Cod home offers the perfect blend of privacy and convenience on just over 6 acres. Surrounded by mature trees and set on a wooded lot overlooking a tranquil pond, you’ll enjoy the calm of nature right outside your doorstep. The freshly installed deck provides a serene spot.

    Nancy Greenwood Watson Realty & Associates

    72 Oakridge Way, 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
  • 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

    $944,999

    • 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
  • 100 Pomfret Rd, Woodstock, VT 05091
    100 Pomfret Rd, Woodstock, VT 05091
    100 Pomfret Rd, Woodstock, VT 05091
    /50

    $895,000

    • 4 Beds
    • 2.5 Baths
    • 2,044 Sq Ft

    100 Pomfret Rd, Woodstock, VT 05091

    Charming, Unique, and Ideally Located! Welcome to 100 Pomfret Road—a beautifully updated farmhouse set on four level, picturesque acres just a short walk from Mt. Tom, Billings Farm, and the heart of downtown Woodstock. This rare find blends timeless character with everyday convenience in a peaceful, brookside setting.Inside, you’ll find a sun-drenched home featuring four

    Keri Cole Williamson Group Sothebys Intl. Realty

    100 Pomfret Rd, 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
  • 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

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 $1,542,585.
How many homes have sold over the last 12 months in Woodstock, VT?
57 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, 05001, 05071, 05048 and 05089.
How much do you need to make to afford a house in Woodstock?
The median home price in Woodstock is $985,000. If you put a 20% down payment of $197,000 and had a 30-year fixed mortgage with an interest rate of 6.19%, your estimated principal and interest payment would be $4,820 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $207K a year to afford the median home price in Woodstock.
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 96 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 $875,000, up 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$875,000
Median Single Family Sale Price
$975,000
Median 2 Bedroom Sale Price
$480,000
Median 1 Bedroom Sale Price
$234,500
Average Price Per Sq Ft
$490
Number of Homes for Sale
38
Last 12 months Home Sales
57
Months of Supply
8.00
Median List Price
$985,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
5%
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