20

South Woodstock, VT Homes for Sale with Garage

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  • /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
  • /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
  • /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
  • /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
  • /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
  • /45

    $725,000

    • 5 Beds
    • 3 Baths
    • 3,028 Sq Ft

    137 Laughlin Rd, Woodstock, VT 05091

    Charming property located just minutes from historic Woodstock Green. The main house first floor features 3 bedrooms/ 1bath with formal dining room, living room and kitchen on first level anchored by an expansive deck for entertaining or enjoying the afternoon sun. Handsome hardwood floors throughout, stainless appliances in the kitchen accented with granite countertops. The lower level is walk

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    137 Laughlin Rd, Woodstock, 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
  • /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
  • /49

    $749,000

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

    37 South St, Woodstock, VT 05091

    Holiday price reduction! 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

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    37 South St, 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. The

    Laird Bradley Williamson Group Sothebys Intl. Realty

    3914 South Rd, Woodstock, VT 05091
  • /57

    $595,000

    • 4 Beds
    • 2 Baths
    • 2,212 Sq Ft

    298 Jenneville Rd, Windsor, VT 05089

    PRICE REDUCED! Welcome to "Valley Brook Farm", an historic cape in the middle of horse country on 12.92 acres with barns, rolling & level pasture, a swimming pond, and brook. Located in the heart of the nationally renowned Green Mountain Horse Association trail network. Nestled on scenic & bucolic Jenneville Road, this c. 1820 cape offers the warmth of wide pine floors, post-and-beam character,

    John Bassette Bassette Real Estate Group

    298 Jenneville Rd, Windsor, VT 05089
  • /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
  • /46

    $1,425,000

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

    4946 South Rd, South Woodstock, VT 05071

    Iconic 1854 Gothic Revival home, known as the Lilac Cottage is located in the heart of South Woodstock Village, just a short stroll to The Ransom Tavern at Kedron Valley Inn, The South Woodstock Store, and Kedron Pond. Many new state of the art updates and improvements throughout this versatile, turn-key home, all honoring and highlighting the period detail. The rooms are spacious, bright and

    Danny Kogut Williamson Group Sothebys Intl. Realty

    4946 South Rd, South 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
  • /26

    $3,300,000

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

    249 Sawyer Rd, Woodstock, VT 05091

    Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary

    Andrew Bustin LandVest, Inc/Woodstock

    249 Sawyer Rd, Woodstock, VT 05091
  • /60

    $1,300,000

    • 4 Beds
    • 5 Baths
    • 3,195 Sq Ft

    125 Shurtleff Ln, Woodstock, VT 05091

    Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for everyday living and entertaining, the main level features an open, light-filled layout, a well-appointed kitchen, and seamless access to a sunny three-season room overlooking the landscaped grounds. The sought-after first-floor

    Keri Cole Williamson Group Sothebys Intl. Realty

    125 Shurtleff Ln, Woodstock, VT 05091
  • /48

    $6,750,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 5,087 Sq Ft

    412 Skyland Ln, Woodstock, VT 05091

    Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 65 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and

    Story Jenks LandVest, Inc/Woodstock

    412 Skyland Ln, 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
  • /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
  • /45

    $895,000

    • 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
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