$1,249,950 $411 per sq.ft. Woodbury VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 3041  |  Acres: 218
Friday Sep 26, 2025
Description: Welcome to 187 East Hill Road, an extraordinary 218-acre estate in the serene town of Woodbury, Vermont. This remarkable property is a rare find, offering unparalleled natural beauty and luxurious rustic living. At the heart of this expansive estate lies a charming log cabin, meticulously crafted with exotic hardwoods that infuse warmth and character into every room. Flooring is Brazilian Cherry, the kitchen is custom crafted of Guyana Mahogany, the great room ceiling is finished in Spanish cedar, and the expansive decks and porches are made of luxurious Ipe decking. The cabin seamlessly blends with its surroundings, providing a cozy retreat while offering modern comforts. The property boasts extensive frontage on the pristine Woodbury Lake. Enjoy serene water views from your private dock, or while kayaking, fishing, and peaceful lakeside moments on your private beach, or your additional deeded access to the lake. The estate's vast network of trails invites you to explore the diverse landscape, whether by foot, horseback, or ATV, making it an outdoor enthusiast's dream. Trails follow waterfalls on one border of the property and will allow the perfect location for a zen / meditation garden allowing the opportunity to get lost in the sound of rushing water as your stress melts away. Whether you seek a private retreat, a family compound, or a nature lover's paradise, 187 East Hill Road offers endless possibilities. See MLS Property & Listing Details & 52 images. Includes a Virtual Tour

$1,195,000 $448 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2668  |  Acres: 8.32
Wednesday Feb 18, 2026
Description: 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, timeless materials, and an effortless sense of place. The interior is bright, welcoming, and designed for both everyday living and memorable gatherings. Wide board floors run throughout, while exposed beams lend texture and authenticity to the inviting den and spacious eat-in kitchen. A butler's pantry provides exceptional storage and service flow to the formal dining room, and multiple living spaces -- including a fireplaced living room with gas insert and a den warmed by a wood stove -- offer comfortable options for relaxing or entertaining in every season. Positioned on more than eight private acres, the setting feels peaceful and secluded, yet remains remarkably convenient: Woodstock's celebrated restaurants, boutiques, and cultural attractions are just minutes away, and premier skiing at Killington's Skyeship Base Lodge is under eight miles from your door. Outdoor living is equally compelling, with a large deck perfectly oriented toward the mountains, an in-ground pool for summer enjoyment, and an oversized garage/barn with storage above presenting exciting potential for a guest suite, studio, or party barn. A rare combination of location, quality, and lifestyle flexibility, this property is ideally suited as a full-time residence, seasonal retreat, or investment in Vermont living at its best. See MLS Property & Listing Details & 57 images.

$1,299,900 $313 per sq.ft. Woodstock NH Home »

5 Beds | 4 Baths |   Total Sq. Ft. 4148  |  Acres: 5
Saturday Feb 21, 2026
Description: Perched at the height of the land here in Woodstock, this sprawling home captures stunning views of Franconia Notch and the surrounding mountain ranges with a jaw dropping 90+ degrees of unobstructed sight line. This historic home features modern appurtenances paired with beautiful handmade finishes inside, setting the tone for private, luxurious mountain living. With 5 acres surrounding the home, you will never have a neighbor in sight. Located within 10 minutes of Loon Mountain, Lincoln, and Woodstock. Enjoy all that the bustling area has to offer while living high above and outside of the noise. The home itself is extremely versatile, with tri-plex arrangement attached through breezeways, you can host 18+ guests comfortably. A full kitchen in each three sections of the home makes for the utmost in privacy between families or even the option to rent out two units while living in one. The list of possibilities goes on and on with this property. Updates include but are not limited to standing seam metal roofing, stand-by (whole home) propane generator, up to date electrical systems, plumbing, and heating. 81 Meadow Ln is your sanctuary in the White Mountains, see for yourself the awe-inspiring sunsets over the mountain ranges, and the stunning beauty of a well kept historic home. See MLS Property & Listing Details & 57 images.

$1,300,000 $407 per sq.ft. Woodstock VT Home »

4 Beds | 5 Baths |   Total Sq. Ft. 3195  |  Acres: 1.07
Tuesday Nov 11, 2025
Description: 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 primary suite offers ease and convenience, with generous closet space and a private bath. With three additional bedrooms plus a dedicated office, the home offers plenty of room to spread out. The large finished basement provides flexible bonus space--perfect for a playroom, media room, fitness area, or hobbies. Central air conditioning ensures year-round comfort, while an oversized, heated garage and an in-ground irrigation system make this home convenient in every season. Step outside to a private patio, surrounded by terraced gardens and stonework that add character and curb appeal. Located in a quiet setting yet within easy reach of restaurants, shops, and the village green, this property offers modern convenience in one of Woodstock's most desirable walk-to-town locations. A rare opportunity to enjoy newer construction in the heart of Vermont's most charming village. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$1,895,000 $644 per sq.ft. Woodstock VT Home »

1000 Ft. of Waterfront on River Ottauquechee River
2 Beds | 3 Baths |   Total Sq. Ft. 2944  |  Acres: 14.9
Tuesday Apr 21, 2026
Description: 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 comprised of a large, open-format living space with gourmet kitchen, dining and living spaces, plus a first level bedroom with modern ensuite bath. Upstairs is another large open floor plan living space with a half-bath, and a full bedroom with ensuite bath. Each side of the upstairs living space has loft sleeping bunk-areas for kids (of all ages!). SEE DEDICATED PROPERTY WEBSITE FOR VIDEOS, VIRTUAL WALKTHROUGH, FLOORPLANS AND MORE. See MLS Property & Listing Details & 33 images. Includes a Virtual Tour

$2,599,000 $434 per sq.ft. Woodstock VT Home »

9 Beds | 11 Baths |   Total Sq. Ft. 5993  |  Acres: 0.46
Sunday Sep 21, 2025
Description: 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 maple-lined streets, stately homes, artisanal boutiques, and a warm and welcoming spirit. The town and assorted local organizations offer cultural and family fun activities offered throughout the year. Currently being used as a 7-room Inn boasting an additional 2-bedroom owner's quarters, this property could be returned to operating as a private residential property with zoning permit. Please contact for more information on making this beautiful place your dream home! See MLS Property & Listing Details & 54 images.

$2,950,000 $543 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $550,000 down 19% on March 13th 2026
6 Beds | 6 Baths |   Total Sq. Ft. 5433  |  Acres: 2
Friday Jun 28, 2024
Description: 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 back ell seamlessly ties into the original brick Federal and offers additional spaces for entertaining guests including the Pine Room with its' large fireplace for snowy winter nights. The brick Federal consists of formal living room, dining room, library and gourmet kitchen with walk in pantry. On the second floor there are 2 ensuite bedrooms,4 more bedrooms, 2 baths and large laundry room. The third floor offers the surprise of a family room that was originally a ballroom with curved ceiling. There is also a bright studio and half bath on that level. The new attached oversize 2 car garage is accessed from the Pine Room and the fully renovated basement. The 2+/- acres comprises of lovely landscaping around the home and plenty of land for gardens . The 18th century barn and corn crib lend much charm to the setting. There are 8 additional acres for sale if one would like to expand the property. Walk to the charming village store and enjoy dinner on the porch of the Ransom Tavern. Only 5 miles to Woodstock and a short drive to multiple ski areas. South Woodstock is truly a bucolic place to call home! Call today for a private viewing. See MLS Property & Listing Details & 40 images. Includes a Virtual Tour

$3,300,000 $896 per sq.ft. Woodstock VT Home »

3 Beds | 5 Baths |   Total Sq. Ft. 3682  |  Acres: 2.37
Monday Dec 15, 2025
Description: 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 residence is perfectly sited to overlook Woodstock's iconic Mount Tom and the Marsh-Billings Museum, Vermont's only National Park. The property sits at the end of a quiet road with only one other neighboring residence and is surrounded by over 400 acres of conserved land. There is a bedroom suite on each of the three levels, allowing family members or guests to claim their own space. The open living room on the main level is a natural gathering place, either by the fire in the winter, or out on the deck in the summertime to take in the views. The adjoining 1,040-sqft modern pool house was completed in 2023, providing a luxurious new extension of the home. Inside is an open floor plan, where floor-to-ceiling windows showcase unobstructed mountain views to the North and West. Thoughtfully designed with a custom Viking kitchen, spa-style walk-in shower, and guest bed, the pool house is ideal for entertaining guests, hosting family parties, or relaxing apres-ski. The outdoor heated pool is a centerpiece of the property, providing four-season enjoyment. See MLS Property & Listing Details & 28 images. Includes a Virtual Tour

$6,750,000 $1,327 per sq.ft. Woodstock VT Home »

4 Beds | 5 Baths |   Total Sq. Ft. 5087  |  Acres: 63.88
Wednesday Jun 4, 2025
Description: 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 Killington are viewed from nearly every room. Finished in 2024, this timber frame home channels modern farmhouse warmth with a clean, contemporary edge.The wall-to-wall glass in both gables frames the surrounding landscape like living artwork, while inside, 24-foot ceilings, radiant heat, A/C, and a sauna provide everyday indulgence and embrace. At the heart of the home is a chef's kitchen with Marinace granite, Wolf and SubZero appliances, and reclaimed hickory floors. Gently sloping meadows invite sledding in winter and lead to the barns below including a 6-stall stable, indoor riding arena with heated viewing area, and a spacious barn perfect for guest quarters, workshop or a car collection. Set between the twin gables, an elevated courtyard with a heated Soake pool creates a seamless indoor-outdoor connection, ideal for sunset reflections in the summer and stargazing in the winter. A 3-bay garage, and stream complete this offering. GMHA, and premier skiing nearby. See MLS Property & Listing Details & 48 images. Includes a Virtual Tour

$14,900,000 $1,190 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $3,100,000 down 21% on April 10th 2026
7 Beds | 10 Baths |   Total Sq. Ft. 12520  |  Acres: 183.7
Thursday Oct 16, 2025
Description: 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 located next to the swimming pond. The main residence, completed in 2010, consists of the center core with porch - for cooking, gathering and entertaining; the owner's quarters with a 2nd floor suite and 2 bedrooms below; the guest wing with 3 first-level bedrooms, second-floor game room and adjacent 8-bed bunk room and a 4-story octagon with wine cellar at the base and flexible multi-use spaces above. All 7 bedrooms are ensuite plus 3 powder rooms. The attached gambrel barn is a professional grade gymnasium with 6-car heated garage underneath. The interior is like a grand lodge in the American West while the exterior with shingles and gambrel barn is traditional New England. The systems and mechanicals are all commercial grade. The finishes and craftsmanship are consistently superb. The atmosphere is relaxed and fun. As a complete fully furnished package, each and every attribute at Star Hill Farm - the location, land, exposure, privacy, views, guest house, barn, pond, residence and gymnasium- is exceptional, creating one of the finest properties in Vermont. See MLS Property & Listing Details & 59 images. Includes a Virtual Tour