$8,950,000 $1,147 per sq.ft. Woodstock VT Home »

4 Beds | 7 Baths |   Total Sq. Ft. 8921  |  Acres: 295.59
Listed on Tuesday Feb 21, 2023
Description: High up in the hills above South Woodstock, Little Baldy Hill Farm is set among rolling meadows with sweeping views of the Green and White Mountains. The 295 acre property offers complete privacy, miles of trails through spectacular classic Vermont landscapes, and a compound with every amenity carefully considered. Inspired by travels through Europe, the house was designed with a romantic, and very comfortable, take on country living. Arched windows and hallways, vaulted ceilings, a rounded tower and a great hall with a massive stone fireplace give context to spaces for gathering with friends and family and cozy nooks for reading. The property embraces its setting: taking in the views and light, with French doors inviting a walk in the courtyard gardens and the stone terrace, a splash in the pool, and quiet puttering in the greenhouse. The main house has four bedrooms en suite with a first floor primary and guest suite. The three-level carriage barn has a one bedroom guest apartment on the top floor. A ramp to the second floor allows for the storage of cars and carriages or makes for a great party barn or studio. Also on this level is a 5 stall stable with wash stall. The lower level houses a heated workshop and plenty of room for toys. The grounds include a tennis court, barn and pond and miles to explore. High speed internet. Surrounded by large landowners and yet close to GMHA and the South Woodstock Country Store. 2.5 hours to Boston. Delayed showings until 2.28.23 See Listing Details & 40 images. Includes a Virtual Tour

$4,300,000 $927 per sq.ft. Woodstock VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 5939  |  Acres: 25.8
Listed on Monday Apr 29, 2024
Description: ByBrook Farm: Reimagined, turnkey 1790s farmhouse set in one of Vermont's most loved valleys, perennial gardens, stone walls, a spring fed pond, a brook, and rolling meadows. Quiet luxury. Just outside the hamlet of South Woodstock on 25 acres, the 2-bedroom 4,667 sf farmhouse and the 2-bedroom 1,273 sf guest cottage are connected by a stone pathway through the gardens. In the recent renovations of the main house, an additional 825 feet were added on for the kitchen and an extension to the upstairs bedroom suite. Vernacular character: Hand-plastered walls reflect the Vermont light, hand-planed boards, hand-hewed beams and a dining room mural by the Hudson River painter, Kevin Paulsen. Comfortable living, beautifully done. Attached to the farmhouse are two parking bays and a bank barn. On the lower level of the post and beam barn is a large gym or studio space. A picnic area on the top of the knoll has views of the rounded hills and the Kedron Valley-- a landscape that has not changed much over the last 200 years. New geothermal system, solar array and a hook-up for an electric car. The main dwelling has whole house A/C. EC fiber high speed internet. 0.2 miles from Kedron Valley Inn/Ransom Tavern and South Woodstock Country Store and less than a mile from GMHA, the oldest horse club in the country. 26m from Killington and 40m from Okemo. 2h 19m from Boston. Showings begin May 10th. See Listing Details & 40 images. Includes a Virtual Tour

$3,500,000 $579 per sq.ft. Woodstock VT Home »

6 Beds | 7 Baths |   Total Sq. Ft. 6040  |  Acres: 38.93
Listed on Friday Mar 1, 2024
Description: "BENEDICT HILL" - sited on 38 acres on a quiet gravel road in a premier location in South Woodstock is this truly classic Vermont estate property. Excellent equestrian / horse potential with historic 5-stall barn and fencing for pastures/paddocks already in place. The land component is comprised of split-rail fence lined pastures, meadows, woodlands, giant maple trees, ancient stone walls and gardens. The main "Stone House" c. 1820 - with period details and 10' ceilings has 4 bedrooms, 3 full and 2 half-baths, gourmet kitchen, a library-den, a wonderful living room and 3 fireplaces on the main level. A stone patio/covered porch spans the rear of the house, and a 2-car attached garage. The original barn was renovated into a fully finished barn/guest house comprised of a fabulous great room with 30-foot ceilings and stone fireplace, kitchen and dining areas. Open stairs lead up to a loft primary-bedroom and bath. Downstairs is a rec/family room, 2 bedrooms and full bath. The present owners have just completed many renovations. This is a rare opportunity to acquire one of the most special, pastoral Vermont properties to come on the market in years - yet is just 5 mins to the hamlet of South Woodstock, 12 mins to the Woodstock village green, and 20-30 mins to I-89, Hanover/Dartmouth and points beyond. SEE FULL PROPERTY WEBSITE. See Listing Details & 40 images.

$3,500,000 $644 per sq.ft. Woodstock VT Home »

6 Beds | 6 Baths |   Total Sq. Ft. 5433  |  Acres: 10
Listed on 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 10 acres comprises of lovely landscaping around the home and plenty of land for gardens and animals. The 18th century barn and corn crib lend much charm to the setting. 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 Listing Details & 40 images.

$3,425,000 $535 per sq.ft. Woodstock VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 6403  |  Acres: 74.65
Listed on Tuesday May 28, 2024
Description: Nestled among verdant rolling hills, High Birch is located in one of the area's most desirable regions at the midpoint between Woodstock and South Woodstock Villages. Designed in 1976 by prominent New York architect Lewis Davis, of Davis, Brody and Bond renowned for his modernist skyscrapers that impacted the skyline of New York City, the home contrasts sleek interior spaces to the surrounding natural landscape. Private and tranquil with pristine views in every direction through walls of tall windows and sweeping ceilings, the rooms are spacious, bright and inspiring- ideal for entertaining and daily living, and communicate directly with exterior spaces, terraces and decks. The kitchen and bathrooms have all been entirely renovated by Studio Nexus honoring and accentuating the original Davis design. The multi-level Great Room is anchored by a raised, polished gray marble fireplace. The Primary Suite is located on the 2nd level featuring a curved wall of windows offering a panoramic view of the neighboring valley farms, complete with a spectacular spa like wet-room, dressing room and laundry. The 2nd level is further completed by three additional bedrooms and 2 bathrooms. The lower level has direct access to the 2-car garage, an office, and spacious bunkroom. The surrounding terraces and grounds are lovely with established perennial beds. There is a swimming/skating pond and a barn for animals, storage, or to house your own sugaring operation. Offered fully furnished. See Listing Details & 40 images. Includes a Virtual Tour

$2,850,000 $471 per sq.ft. Woodstock VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 6443  |  Acres: 54.83
Listed on Wednesday Aug 23, 2023
Description: Serene, private, contemporary: Sited on a ridge above South Woodstock village, the 54 acre property offers complete seclusion in an elegant setting with an extensive network of trails. The three bedroom main dwelling is sleek and elegant, with an open floor plan crafted to take in the beauty of the site with abundant use of organic material designed to integrate the design with the surrounding Vermont countryside. The two bedroom guest cottage has its own garage and entrance off of Ebbin Lockwood Way. The 6,048 s/f main house and 1,584 s/f guest cottage were designed by architect, Michael Weinberger. The property was recently renovated: main house was upgraded and many new system improvements. From the stone terrace, there are views of a cascading waterfall flowing into a small Koi pond and perennial gardens. On the Northeast side, an outside sitting area takes in views of a long, rolling meadow with a pond and a glimpse of the local hills. The main house includes a detached garage with additional storage space. Less than 1/2 mile from South Woodstock Country Store and Kedron Valley Inn/Ransom Tavern and one mile from Green Mountain Horse Association. 25 min. from Mt. Ascutney mountain biking trails, 38 min. from Killington and 2:23 hrs. from Boston. See Listing Details & 40 images. Includes a Virtual Tour

$2,695,000 $681 per sq.ft. Woodstock VT Home »

4 Beds | 5 Baths |   Total Sq. Ft. 5017  |  Acres: 10.86
Listed on Tuesday Apr 30, 2024
Description: Absolutely stunning, newly renovated residence, privately situated towards the end of a quiet town road in Woodstock, in an area of other substantial homes. Lovely mountain views and 10+ acres of privacy. The present owners have completed over $1 million in documented renovations in the past three years, including a fabulous new gourmet kitchen, powder bath, new bamboo flooring throughout the open floorplan kitchen-dining-living area. They added a wood burning fireplace in the living room behind which was added a new, spacious screened porch that overlooks and listens to the sounds of the babbling brook below. The primary bedroom suite (with ensuite office) on the first floor received a bathroom renovation and a stack laundry washer and dryer. The lower level was renovated into a large recreation hangout room with bar, stone fireplace with a propane wood stove, pool table area, TV area, a full bath, a new full laundry area and a workout room, and added A/C throughout. In addition to the attached 3-car garage, they built a brand-new detached barn-garage with commercial overhead doors and room for ALL your motorized vehicles, toys, outdoor gear, workshop tools (or any other purpose you have in mind). 1st-rate mechanicals: Viesmann propane boiler system, automatic backup generator, radiant/radiator/mini-split heat and A/C on all levels and all bedrooms. Both the attached 3-bay garage and the detached barn-garage are insulated and heated. SEE FULL PROPERTY WEBSITE. See Listing Details & 40 images.

$2,395,000 $568 per sq.ft. Woodstock VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 4214  |  Acres: 1.07
Listed on Saturday Feb 24, 2024
Description: 10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in 2012 by the respected local architect David Bielman. The front door welcomes guests with a pair of dutch-doors in a center entrance foyer, flanked by a classic dining room and elegant living room (both with fireplaces). The classic butlers pantry leads to the gourmet kitchen and a wonderful, sunny eat-in breakfast area. There are 4 additional BRs upstairs, 2 have ensuite baths plus a 3rd hall bath. There are also powder baths on the first floor and in the lower (basement) area. All BRs have central air. Mechanicals have been updated and well-maintained. 2 other offices on 1st and 2nd floor, and the basement has living space, a workout room, safe room, and ample storage. Beyond the kitchen is a mud-laundry room that leads to the covered (heated) brick walkway from the garage. The 1.05 acre parcel has professionally designed and executed gardens, patios and stone walls including new stone steps that lead up to a second new stone patio that enjoys sweeping vistas across to Mt Tom and the Marsh-Billings-Rockefeller National park. SEE FULL PROPERTY WEBSITE. See Listing Details & 40 images.

$2,200,000 $561 per sq.ft. Woodstock VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 3925  |  Acres: 1.12
Listed on Wednesday Jun 26, 2024
Description: This historic home was built in 1904 by John Cotton Dana for his family around 1904. The Danas were a prominent family in Woodstock . The Dana House , home of the Woodstock Historical Society, is a major landmark in Woodstock. The house has recently undergone a comprehensive renovation. The large open rooms ,enveloped with light and lovely views , create a sophisticated yet cozy setting. The floor plan offers spaces for every age to enjoy. The first floor has a charming, spacious living room with fireplace , gracious dining room, gourmet kitchen , office and sunroom.The second floor offers 3 ensuite bedrooms and a large laundry room. The third floor offering two bedrooms , living room kitchen combination ,bath and laundry with a separate entrance is perfect for guests, or could be an independent rental apartment. The outside grounds are beautifully landscaped with extensive decks and patios for outdoor entertaining . It is an easy walk into Woodstock Village while providing a quiet , serene setting . Present property taxes are based on 2.2 acres . The new taxes will reflect the new size of 1.1 acres. One of the grandest properties in Woodstock . Call for an appointment for a viewing . See Listing Details & 34 images.

$1,999,000 $257 per sq.ft. Woodstock VT Home »


Price Change! Reduced by $151,000 down 8% on June 28th 2024
10 Beds | 12 Baths |   Total Sq. Ft. 7769  |  Acres: 5.5
Listed on Friday Jun 7, 2024
Description: Vermont is calling you! Experience the charm of Woodstock, VT with its quaint Main Street and enjoy the proximity to Killington Resort, just a short drive away. This exceptional property offers a unique blend of natural beauty and year-round recreational opportunities, perfect for creating lasting memories. Whether you're looking for a family compound or a multi-family investment opportunity, this property offers versatility like no other providing privacy while fostering a sense of togetherness. An ideal setting for gatherings and celebrations of all sizes. The Inn building includes a commercial kitchen, several dining rooms, a tavern,and six ensuite guest rooms. The residence is perfect for a more intimate gathering with an open concept main level kitchen/living/dining experience with 3 ensuite bedrooms upstairs plus a main level, king bed suite with kitchenette while the motorcoach can be used to generate income and/or offers a special glamping experience with stunning mountain and water views of its own. Snowmobile right from your backyard! All this along the Otterquechee River on 5.5 acres in Woodstock VT! Unbelievable opportunity and location See Listing Details & 40 images. Includes a Virtual Tour

$1,895,000 $631 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 3001  |  Acres: 28.6
Listed on Wednesday May 29, 2024
Description: This lovely country contemporary home offers the very best of Vermont living. With its end-of-the-road location, just 6 miles from Woodstock Village-the location offers privacy and convenience in a desirable location with wonderful neighbors and significant sales. You'll feel as if you've entered your own private sanctuary here...The house was built to take advantage of the gorgeous views and southern exposure. Once you enter the door you cannot help but feel yourself relax. Warm wood floors and finishes throughout the open first floor gathering rooms. Updated kitchen and dining room with floor to ceiling windows, an expansive living room w/woodstove open onto a wonderful deck with a firepit under the shade of a great old maple to frame the mountain view. First floor office/study, mudroom with direct entry from oversized two car garage and lovely foyer complete the first floor.2nd floor bedrooms & bonus rooms/study offer flexibility & space for all plus an updated bath w/ soaking tub. Primary suite on 3rd floor faces view & features plentiful storage incl. cedar closet, whirlpool tub & sitting area.The 28.6 ac lot is a gardeners delight-with many fruit trees & bushes, mature perennials,garden shed,raised beds, gazebo & greenhouse.Enrolled in VT Land Use, there are trails for walking, x-country skiing & snowshoeing. Finished, heated studio barn w/1 BR apt., outdoor shower & deck.Generator & Solar(owned)too! A truly exceptional opportunity in an amazing Woodstock,VT location! See Listing Details & 40 images.

Under Contract Woodstock VT Home for sale $1,685,000 $937 per sq.ft.

$1,685,000 $937 per sq.ft. Woodstock VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1798  |  Acres: 5.18
Listed on Monday May 13, 2024
Description: Cloudland Aerie is an exceptionally rare offering of an unprecedented out parcel of Maplewood Farm, Woodstock, Vermonts most iconic farm property. The owner is the son of the previous owner of Maplewood Farm and was gifted this magnificent 5.18 acre parcel on which he built his 3 bedroom home. Accessed by Cloudland Road, the driveway is a scant quarter of a mile from Old River Road. The post and beam home was sited with southern exposure and direct views of Blake Hill and the surrounding farmlands. The elevated homesite is well above Cloudland Road to give complete privacy and yet is only 4 minutes from Woodstock Village. See Listing Details & 20 images.

$1,675,000 $457 per sq.ft. Village of Woodstock in Town of Woodstock VT Home »


Price Change! Reduced by $425,000 down 25% on May 25th 2024
6 Beds | 4 Baths |   Total Sq. Ft. 3668  |  Acres: 3.68
Listed on Sunday Sep 3, 2023
Description: Amazing opportunity to own a very special property on the market for the first time in over 50 years. Built in 1880, "Rose Hill" was one of the premier homes in the Woodstock Village area. The 6 bedroom 4 bath house sits on just under 4 private acres and is conveniently located less than a mile from the Village Green and the Woodstock Inn and only 1/4 of a mile from the Rec Center. Stone walkways, mature trees and old gardens dot the landscape. The over sized covered brick porch is waiting to reclaim the lovely views to the South. Inside, you are greeted by a large foyer that leads to the stately living room with a magnificent fireplace centering the room. To the left is the dining room which leads to the kitchen, and a window filled den is off to the right. There is a dutch door out to the porch and an eye catching staircase with a wood banister and ornate spindles that takes you upstairs. The 2nd floor is home to 6 bedrooms including a large center room with an elegant fireplace. In addition to the main house, there is a detached garage with a 2 bedroom apartment and a 2 bedroom cottage which includes a living room with fireplace, dining room, kitchen and bath. In need of updates and some renovations, this property is looking for the next steward to return the house to its former glory. Ideal as a primary residence, 2nd home getaway, or redevelopment investment. Short drive to the Woodstock CC and Saskadena 6, while Killington and Dartmouth are less than 30 minutes away. See Listing Details & 38 images.

$1,675,000 $630 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2660  |  Acres: 20.7
Listed on Wednesday Jul 3, 2024
Description: Round Top Cottage is sited on a knoll just outside the village of South Woodstock on 20 acres, offering complete privacy and views of the rolling hills framing the Kedron Valley. This three-bedroom lodge, fully renovated in 2024, blends modern amenities with rustic elegance. The open floor plan features cathedral ceilings in the main living and dining area, creating an inviting space to gather (or enjoy quiet time). The first floor primary suite has lovely light and a generous soaking tub. The second floor includes a sitting area, two bedrooms, and an office. In the summer, enjoy outdoor living with a fire pit for evening gatherings under the stars. Direct access to trails for all season exploration. Equestrians will appreciate the potential to build a small barn with a paddock, and the short hack over to Green Mountain Horse Association (GMHA). Close to skiing: 23 miles from Killington, 22 miles from Okemo, and 10 miles from Saskadena Six. See Listing Details & 31 images. Includes a Virtual Tour

New Listing! Woodstock VT Home for sale $1,500,000 $875 per sq.ft.

$1,500,000 $875 per sq.ft. Woodstock VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1714  |  Acres: 15.8
Listed on Friday Jul 12, 2024
Description: Discover an unparalleled woodland retreat nestled on a picturesque hilltop in South Woodstock, Vermont. This extraordinary timber frame home, a masterpiece of craftsmanship, offers breathtaking views of the pristine Green Mountain Horses Association show arenas and cross-country course. Each stone, beam, and timber has been meticulously and artfully placed by the current owner, reflecting a labor of love and dedication. This unique property has been cherished by the same family since 1965, imbuing it with a rich history and a profound connection to the land. The 2-bedroom, open-concept hillside retreat is enveloped by a serene hardwood forest, accessed via a private driveway aptly named Horseshoe Way. This path honors the farrier who envisioned and created this sanctuary as a tribute to a family of farmers who devoted their lives to their community. The home itself is a testament to Vermont's heritage, constructed from materials carefully curated from some of the state's most iconic early barns and sawmills. Every element of this residence tells a story, blending the past's rustic charm with modern comforts. Whether you seek a peaceful haven or a base for outdoor adventures, this South Woodstock retreat offers a unique opportunity to embrace a lifestyle of tranquility and natural beauty. Don't miss your chance to live on a parcel steeped in Vermont's history and create your own cherished memories in this remarkable woodland sanctuary. Delayed Showings - start 7/18. See Listing Details & 26 images. Includes a Virtual Tour

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