$3,499,000 $538 per sq.ft. Winhall VT Home »

6 Beds | 7 Baths |   Total Sq. Ft. 6500  |  Acres: 40.8
Listed on Friday Mar 17, 2023
Description: Your 40 acre Mountain Playground and Stratton Mountain Estate is nothing short of EXTRAORDINARY! Recently expanded and renovated this grand lodge now boasts 4 en suite bedrooms, three stone fireplaces, huge lodge room with large beams, walls of glass and VIEWS, VIEWS, VIEWS. Gourmet kitchen, plus a 2 BR/2BA Guest House - each with unrivaled views of Stratton Mountain's trails.You'll be captivated by commanding southerly views of Stratton Mountain, surrounding ridge lines and sunset views to the west. This property is without comparison and the last rare parcel of this size near the resort. Enjoy a world of privacy and tranquility. Just minutes to the Base Lodge, you'll come home to endless outdoor fun. Bring your ATVs, snowmobiles and in summer there's a pond and tennis court. Patios, Stonework, outdoor spaces enhance the stunning location. Situated in the heart of everything the region has to offer throughout the seasons. World Class professional theater, the Manchester Music Festival, The Dorset Summer Equestrian Festival. Hiking, biking, kayaking, shopping and dining. Fall foliage, first tacks on powder days and the glorious Green Mountain Summers beckon. This one of a kind property has the essence of a true mountain lodge, set into its surroundings with a tranquil and peaceful vantage point. Adventure is at your doorstep.Additional land parcels available. Make plans to visit this newly expanded and renovated property. 8 Bedroom septic. You'll be enthralled! See Listing Details & 38 images.

$1,430,000 $467 per sq.ft. Woodstock VT Home »


Price Change! Reduced by $20,000 down 1% on June 11th 2024
5 Beds | 5 Baths |   Total Sq. Ft. 4698  |  Acres: 5.1
Listed on Friday Apr 12, 2024
Description: An expansive 5 bedroom home, in a private location, conveniently just a few minutes drive from Woodstock Village! Among often sought amenities are a ground floor primary bedroom suite with private bath, a dramatic great room with cathedral ceiling and wood burning fireplace, a generously sized lower level in-law/guest suite with kitchen, dining, living room and bedroom with bath, 3 additional upper level bedrooms with 2 full baths, a family room with an attractive soap stone wood burning stove, a bright kitchen with cherry cabinets and an attached 2 car garage. The well conceived design presents the practical opportunity for single level living utilizing the gracious ground floor bedroom suite. Alternatively, the 5 bedrooms, on 3 levels, can satisfy a whole gang! The lower level private suite could present comfortable accommodations for an in-residence caregiver. Outside, a large wrap around deck transitions to pleasant sunny lawn areas with perennial gardens. Within walking distance are Mt. Tom's hiking trails! The property benefits from owner's who have taken pride in maintaining their beloved home! An attractive home that benefits from a thoughtful interior design! Equally suited for use as a well located year round residence or to be the vacation home that can accommodate friends and family alike! Skiing at Suicide Six as well as all the well known Woodstock Village amenities of shopping, dining and cultural events are just minutes away! Truly a great Woodstock property! See Listing Details & 40 images.

$1,495,000 $704 per sq.ft. Woodstock VT Home »

Waterfront on River Ottauquechee River
4 Beds | 3 Baths |   Total Sq. Ft. 3089  |  Acres: 0.52
Listed on Monday Jun 10, 2024
Description: 16 Church has the most stunning view of the river from any house in the village that we have seen, perched up above a series of river rapids so the sounds of the river during the day or in the evening are incredibly peaceful and relaxing. Plus, 16 Church is privately nestled in, like a secret hideaway, yet steps to the village green (and a level walk to/from). And more unusual for the village, it has a two-car garage with a covered walkway into the mudroom entryway (plus more outside parking). The spacious kitchen/dining area opens to the vaulted-ceiling living room, which has an INCREDIBLE view up-river. A side door leads to the side-deck that has the same view and sound of the river for outdoor dining above the river. There is a propane woodstove in the living room and woodstove in the kitchen/dining. A 1st floor bedroom has an ensuite bath and small stack washer-dryer. Upstairs is a large bedroom looking out through the great room to the river, a smaller bedroom, a bath and lovely loft area above the living room. Downstairs is a large den/rec/office, a bedroom, a bathroom, the main laundry room and mechanical room, all renovated 11 years, post the Irene storm, when the river waters came up into the lower level. There are beautiful gardens in the front and rear of the house. SEE PROPERTY WEBSITE FOR 16 CHURCH ST WOODSTOCK FOR MORE DETAILS, FLOORPLANS HI REZ PHOTOS AND MORE. See Listing Details & 40 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.

New Listing! Woodstock VT Home for sale $1,675,000 $630 per sq.ft.

$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

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.

$1,775,000 $626 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2836  |  Acres: 1.33
Listed on Monday Jun 24, 2024
Description: "The Schoolhouse," is a turn-key village home overflowing with charm and character. Sited on a hill overlooking the picturesque village of South Woodstock, this light-filled residence offers a unique blend of historical significance and modern luxury. Originally an elementary school from 1903 to 1960, this Queen Anne-style building was beautifully renovated in 2024, preserving its historic soul while incorporating contemporary comforts. The home boasts an impressive 11'7" ceilings, tall windows, and spacious rooms that invite natural light to dance across the interiors. With 2,836 square feet, the home features three en suite bedrooms (two on the first floor), each thoughtfully designed to offer privacy and comfort. The new kitchen is equipped with modern appliances, marble counters and plenty of storage, making it perfect for culinary adventures. Living in this delightful home invites participation in a vibrant community: walking distance to the swimming pond, the inviting porch at Ransom Tavern for dinner, and the South Woodstock Country Store. Special events like contra-dancing at the Green Mountain Perkins Academy add to the village's appeal. Less than a mile away is GMHA, and the region offers endless opportunities for gravel biking and outdoor exploration. High-speed internet. Additionally, there is available land for sale for a guest house or barn, providing ample space for grazing animals. 15-34 min to Saskadena, Killington or Okemo. Showings begin June 27. See Listing Details & 28 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.

$1,895,000 $786 per sq.ft. Woodstock VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2411  |  Acres: 32.11
Listed on Wednesday Jun 5, 2024
Description: Travel a mile south of Woodstock Village on Church Hill Road and you'll discover a rural refuge that combines seclusion with proximity to village life. Two dwellings, a modern home and a separate cottage sheltered by woodland are discreetly sited overlooking a sparkling two-acre spring-fed pond. Each residence offers three bedrooms and two baths with open floor plans and single level living. The 2400 square-foot main house was designed to integrate indoors with the outdoors with light-filled rooms stepping out to lovely established gardens and a terrace paved with massive stones above the pond. The great room with cathedral ceiling and a bright, spacious kitchen both provide welcoming gathering spaces. A screened porch with built-in grill cove can be enjoyed during three seasons. The 1500 square-foot cozy cottage is centered on a relaxed family room with a fireplace adapted for more efficient woodstove use. From its hilltop position, the cottage's expansive deck offers views over an open meadow and down the valley to Mt. Tom. A detached workshop studio and a light-filled writer's cabin further complete the property's serene setting. See Listing Details & 40 images. Includes a Virtual Tour

$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

$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 offer 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.

$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.

$2,695,000 $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.

$2,850,000 $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

$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

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