South Woodstock, VT Homes for Sale with Acreage

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

See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen—complete with a Sub-Zero

Tami Sullivan Snyder Donegan Real Estate Group

CREAMPOT FARM- Idyllic country estate with easy access to Woodstock Village. Set on 104+ acres, this pristine property offers private groomed trails, beautifully landscaped grounds, multiple ponds, and stunning southerly views toward Mount Ascutney. From the moment you enter the gated drive and wind through stone walls, there is an immediate sense of peace and privacy. Originally built by G.R.

David Donegan Snyder Donegan Real Estate Group

The property is located on Town Farm Hill Rd, one of the most beautiful ridgeline Vermont roads with long range mountain views to the east and south. At certain times of the day the lighting brings out the true meaning of “purple mountain majesty”. Over the years the seller has acquired multiple parcels to create this beautiful sanctuary setting. The house is positioned to take in the mountain

Terry Davis Williamson Group Sothebys Intl. Realty

An efficient 2-bedroom chalet located in the foot hills of West Windsor. Over the years the sellers have completed a total gut renovation of the interior and exterior of the house. New windows, doors, hardwood flooring, built-ins, remodeled bathrooms and kitchen are just few upgrades to this charming home. A 2-car garage was added with a large heated bonus room above, which can be used as a

Terry Davis Williamson Group Sothebys Intl. Realty

Historic character, beautifully reimagined for modern Vermont living.Minutes from Woodstock Village, this extensively renovated four-bedroom home pairs the warmth and authenticity of its 150-year-old wide-pine floors and exposed beams with a remarkable collection of recent improvements.At the heart of the home is a brand-new, high-end kitchen with Bosch appliances and newly installed

Keri Cole Williamson Group Sothebys Intl. Realty

Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5 bedroom, 4 bathroom extended cape styled home was renovated approx 15 years ago with handsome hardwood floors throughout. Large kitchen with Calcutta Marble, Electrolux stainless appliances and ample storage that opens into the dining room- The formal

Gretchjen Smith Williamson Group Sothebys Intl. Realty

If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends,

Mandolyn McIntyre Crow Real Broker LLC

On a small hill, amongst trees and beautiful gardens, sits this beautifully maintained log cabin with sweeping views of the surrounding mountains and river valley. Just a short drive outside of Woodstock Village, this cabin offers the perfect blend of privacy and convenience. Built in 1996, this thoughtfully crafted home features approximately 2,600 square feet of living space on 2.9 acres. The

Jennifer Kirkman KW Vermont Woodstock

This nicely updated ranch on a country acre is a rare opportunity to live in Woodstock without breaking the bank. Perfect for downsizing, one-level living, starting out, or even an easy-to-care for vacation home. There is plenty of storage for skis or other recreation equipment in the oversized two-plus car garage and two bay shed with a concrete floor. Sellers have spent 12 years gradually

Tambrey Vutech KW Vermont Woodstock

Sheep Run Farm takes its name from the stone-walled lanes where a prosperous 19th-century farmer once moved his sheep between the barn and upper meadows. Nearly two centuries later, those walls still trace the landscape, framing a beautifully reimagined Vermont farmstead on 21± acres in West Windsor, 3 miles from South Woodstock and 8 miles from Woodstock Village.Drawing on the

Dia Jenks LandVest, Inc/Woodstock

Constructed in 2025, and located in the desirable Rush Meadow region of West Windsor, this impeccably orchestrated Yankee Barn Post and Beam home features superb materials, old world craftsmanship and detailed fit and finish. Custom milled cabinetry and built-ins throughout. The rooms are filled with natural light with stunning bucolic views from every window. The home is centered by a dramatic

Danny Kogut Williamson Group Sothebys Intl. Realty

Two buildings on one parcel in desirable Hartland, Vermont! This flexible and well-maintained property includes a single-family home and a duplex, offering outstanding potential for owner occupancy, multi-generational living, or investment income. Ideally situated just 25 minutes from Hanover, NH, and 10 minutes from Woodstock, VT, this location provides the perfect balance of convenience and

Loren Wehmeyer Tesla Realty Group, LLC

This unique one-of-a-kind property will inspire your creativity. "The Silo House" is located on a tranquil, private lot in the desirable Rush Meadow region of West Windsor with frontage on the Willow Brook and rear access to the local trail system. There are two bedrooms, a LR/DR combination and a large shaded deck overlooking the brook. Perfect for full time living, or a great second home

Danny Kogut Williamson Group Sothebys Intl. Realty

Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx 32 acres. This stunning extended antique post and beam cape is complete with a large traditional 4 story barn with 6 horse stables and equipment sheds offers everything one could wish for in a country property. The grounds include gracious old maples, beautiful

Gretchjen Smith Williamson Group Sothebys Intl. Realty

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

Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's most desirable locations: a place where life slows and the beauty of the Vermont countryside takes center stage. At the end of a quiet road, the property combines sweeping mountain views, and exceptional privacy with a thoughtfully designed hand-crafted, timber frame

Story Jenks LandVest, Inc/Woodstock

Rare opportunity to own one of the most unique compound properties in West Windsor. "The Dome" and The "Silo House" share a lovely 13.9 AC secluded and tranquil parcel fronting the Willow Brook in the desirable Rush Meadow region of West Windsor with rear access to the extensive local trail system.Beautiful established gardens, and mature plantings. Excellent rental investment potential. Both

Danny Kogut Williamson Group Sothebys Intl. Realty

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

Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm

Wade Treadway Wade I Treadway Real Estate

Nestled in the highly desirable Woodstock area, this property offers the perfect canvas for your vision. Featuring an older mobile home and a spacious barn, the possibilities are there for those looking to create a country retreat, hobby farm, workshop space, or future building site.The barn provides valuable storage or recreational use, while the existing mobile home offers a starting

Daniel Preston KW Vermont Woodstock

Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 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

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 a

Gretchjen Smith Williamson Group Sothebys Intl. Realty

Discover the possibilities at Wise Pines, an extraordinary 40± acre property in the heart of Hartland, Vermont, ideally located between Woodstock and Quechee. Surrounded by rolling hills, mature forests, and tranquil walking trails, this unique property was thoughtfully created as a sustainable wellness retreat and offers an exceptional opportunity for its next owner. Wise Pines began its journey

Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout including a brand-new kitchen, refreshed flooring, modernized bathrooms, fresh interior paint, a new garage door, an automatic full-house generator, and more. The property is offered FULLY TURNKEY, with nearly all furniture and furnishings conveying with the sale (artwork excluded). Privately sited in

John Snyder Snyder Donegan Real Estate Group