Woodstock, VT Homes for Sale

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

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

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

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

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

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

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

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

Gilbert’s Hill, the very best of Vermont living - Iconic, 112-acre estate with a storybook history as the first “modern” ski run in the US. Located two miles from the village center of Woodstock, the “prettiest small town in America", experience rural peace with convenient access to great restaurants and shops. Turnkey, fully-restored Vermont farmstead - a picturesque family compound with 7

Chris Lang

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

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

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

These 1200 sq. ft., 2-bedroom, 1.5-bathroom condos are being sold for less than half of their fair market value! Available for immediate move-in, each condo has an open-concept kitchen, dining room, and living room, which are on the airy and light-filled second floor. There is a small deck off the living room. The two cozy bedrooms are on the first floor. Electricity bills will be offset by solar

Jane Darrach Martha E. Diebold/Hanover

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

NEW PRICE! 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

Tambrey Vutech KW Vermont Woodstock

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

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. Gather

Keri Cole Williamson Group Sothebys Intl. Realty

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

Great location minutes from Woodstock Village, South Woodstock, and Green Mountain Horse Association. Kidder Brook runs along the North property boundary, and a sunny lawn area has multiple small gardens. The home is a well-cared for 1973 mobile home on a concrete slab, and there is a two-car detached garage which can be used for vehicles or a shop space. This approximately 1.95 acre lot has

Andrew Hubbell Vermont Real Estate Company

The Richmond House – Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a proud brick Federal distinguished by its softly weathered rose-hued patina and refined architectural detail. Set on more than an acre behind a classic white picket fence and thoughtfully reimagined under the direction of Laurence Rockefeller, the property comprises three

Derek Cosentino Four Seasons Sotheby's Int'l Realty

These 1200 sq. ft., 2-bedroom, 1.5-bathroom condos are being sold for less than half of their fair market value! Available for immediate move-in, each condo has an open-concept kitchen, dining room, and living room, which are on the airy and light-filled second floor. There is a small deck off the living room. The two cozy bedrooms are on the first floor. Electricity bills will be offset by solar

Jane Darrach Martha E. Diebold/Hanover

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

Welcome to Starry Hill, a fully furnished, handcrafted, solid-timber Colonial privately nestled on 18.9 tranquil acres just 5 miles North of Woodstock. This 3-bedroom, 2.5 bath home was built over 4 years by a family of loggers and master craftsmen. Used recently as an AirBnB rental and ready for occupancy. This exceptional home features Eastern white pine walls, hemlock structural beams, and

John Bassette Bassette Real Estate Group

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

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

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

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

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 complete

Carol Wood Williamson Group Sothebys Intl. Realty

Set on a sun-bathed hillside between Woodstock Village and the renowned slopes of Killington and Pico, this custom-built Colonial captures what buyers seek most in Vermont: privacy, craftsmanship, and striking mountain views that feel close enough to touch. Thoughtfully designed by the respected Vermont Vernacular Builders, the home reflects classic regional architecture with refined proportions,

Keri Cole Williamson Group Sothebys Intl. Realty