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Land for sale in Woodstock Vermont

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$6,900,000 468.36 acres 5 Beds | 4 Baths | 4165 sqft
2358 Long Hill Road, Woodstock, VT 05071 - Windsor County

468.36 acres Woodstock, VT

The 468-acre Birch Tree Farm is an unparalleled family recreational retreat offering privacy and a vast array of activities within eight miles of Woodstock. The five-bedroom main lodge offers a generous open floor plan with a well-appointed kitchen and a great room featuring an impressive floor-to-ceiling fieldstone fireplace and tall windows framing the Ottauquechee River Valley. An expansive deck faces the view overlooking the infinity pool, stocked pond, apple orchard and meadow. The three-level bank barn is finely finished in fir, oak and pine with 7 box stalls on the first level, and an extraordinary recreation and media room on the 2nd level. Miles of carriage-width trails connect to the GMHA trail networks, and to the top of 2,409 fo
$4,500,000 82.5 acres 4 Beds | 8 Baths | 6980 sqft
387 Benedict Road, Woodstock, VT 05071 - Windsor County

82.5 acres Woodstock, VT

"SUNNYSIDE" is one of the most perfectly designed and constructed brick Georgian Revival residences in New England - located on a prestigious South Woodstock hilltop on 82.5 acres, with beautiful panoramic views of the surrounding hills and offering absolute privacy. Construction was completed in 2002, with unparalleled attention to detail. And the property has been meticulously manicured and maintained. The 7,000 square foot main residence combines a formal elegance with a beautiful Vermont hilltop setting. The residence features four fireplaces, expansive living and dining rooms, a butternut paneled library, den, continuous flow swimming pool, three-story elevator and a large, beautifully appointed gourmet kitchen with adjoining pantry. T
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$3,900,000 75.1 acres 5 Beds | 6 Baths | 4936 sqft
630 Morgan Hill Rd, Woodstock, VT 05191 - Windsor County

75.1 acres Woodstock, VT

Glenmorgan is an iconic early 19th century turn-key estate with a 5-bedroom 1835 Brick Federal residence, 2-bedroom carriage house, antique bank barn, 3 car garage, cottage and 1 acre swimming pond on 75 acres located in a premier area in South Woodstock surrounded by major estates. The elegant residence is warm and inviting in a distinguished Vermont vernacular, with great light and flow. The carriage house is set up beautifully for guests or party space: the great room is centered on a stone fireplace next to a country kitchen, with a 2nd floor bunk room. The classic bank barn 1st level opens to a pastoral view of the pond and gardens, perfect for larger gatherings, studio or working barn. MacKenzie Hall, a tiny charming pondside cottage
$3,750,000 119.6 acres 5 Beds | 8 Baths | 6866 sqft
164 Hewitt Lane, Woodstock, VT 05091 - Windsor County

119.6 acres Woodstock, VT

A sophisticated country family retreat, Havenwood combines close-tothe-village location with end of the road privacy on 119.6+/- acres. Impeccably renovated and intelligently planned, the main house feels intimate yet expands to fit a crowd. The central open kitchen/family area is centered around a big fireplace with ample separation for a quiet study. Other gathering spaces include a beautiful screen porch and multiple outdoor terraces to enjoy the gorgeous landscape. The lower level has a fun game room as perfect recreation space that opens on to a stone terrace, and a sophisticated temperature controlled wine room. The gracious master suite is on the ground level, with 4 additional bedrooms on the second floor. The guest house-barn
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$2,950,000 55.76 acres 5 Beds | 4 Baths | 6500 sqft
1532 Happy Valley Road, Woodstock, VT 05091 - Windsor County

55.76 acres Woodstock, VT

This contemporary cape with classic Vermont lines is built on the history of two fully reconstructed antique post and beam frames. Architect designed, custom built, and unquestionably one of the nicest homes in Woodstock. There is beautiful interior space, newly created guest/extended family quarters, four fireplaces, and 55.76 acres of playground. Soaring cathedrals, a gourmet kitchen, a massive stone fireplace, magnificent P&B frames, and old wide plank floors make this a one of a kind Woodstock retreat. Happy Valley Road is on the easterly side of town with quicker access to major metro hubs and downtown Woodstock. Five (5) bedrooms and five (5) bathrooms and over 6,000 sqft of living space are finished to an exacting level of detail. Th
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$2,950,000 55.76 acres 5 Beds | 4 Baths | 6500 sqft
1532 Happy Valley Road, Woodstock, VT 05091 - Windsor County

55.76 acres Woodstock, VT

This contemporary cape with classic Vermont lines is built on the history of two fully reconstructed antique post and beam frames. Architect designed, custom built, and unquestionably one of the nicest homes in Woodstock. There is beautiful interior space, newly created guest/extended family quarters, four fireplaces, and 55.76 acres of playground. Soaring cathedrals, a gourmet kitchen, a massive stone fireplace, magnificent P&B frames, and old wide plank floors make this a one of a kind Woodstock retreat. Happy Valley Road is on the easterly side of town with quicker access to major metro hubs and downtown Woodstock. Five (5) bedrooms and five (5) bathrooms and over 6,000 sqft of living space are finished to an exacting level of detail. Th
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$2,750,000 53.2 acres 5 Beds | 6 Baths | 4887 sqft
113 Pomfret Rd, Woodstock, VT 05091 - Windsor County

53.2 acres Woodstock, VT

Elegant modern design, evocative of Vermont vernacular, serene, private setting, close to Woodstock village: This AIA award winning design by Ertel Associates is centered around the repurposed hand hewn post & beam barn enhanced by modernist elements of the kitchen. The interior design of the 4,800 sf, five-bedroom home features clean lines and high end finishes. The first floor master wing has windows on all sides with a barrel vaulted ceiling. The ivy covered stone garage with walled roof garden grounds the design in the hillside. Sited on 53 acres high on a west-facing hillside the property includes exceptional views and a series of stone walls and grass terraces that anchor the residence into the landscape in a simple, elegant style.
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$2,450,000 137.39 acres 4 Beds | 3 Baths | 3614 sqft
585 Brown Hill Rd, Woodstock, VT 05071 - Windsor County

137.39 acres Woodstock, VT

Fieldstone is the quintessential Vermont country property: a stone cape built c.1810 and renovated to fine condition, privately sited at the end of a gravel road, with views to distant hills over meadows and three cascading spring-fed ponds on 137+/- acres. The 3,600 square foot, 4-bedroom main residence combines period details with updated finishes: exposed hand-hewed beams and handsome pine and cherry floors, deep inset 12/12 windows, and two brick fireplaces. Kitchen offers beautiful birch cabinets, high quality stainless appliances and granite counters. Family room opens to a stone terrace surrounded by perennial gardens and a tranquil orchard. Bedrooms are generous, including a main level bedroom with fireplace. A 3-bedroom guesthouse
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$1,800,000 82.9 acres 4 Beds | 4 Baths | 3832 sqft
299 Grassy Lane, Woodstock, VT 05091 - Windsor County

82.9 acres Woodstock, VT

HONEY HILL FARM- Simply one of the nicer estates in Woodstock. This is the quintessential Vermont Country Home. Only five minutes from Woodstock Village in the prestigious Prosper Hill area. There are 82 splendid acres with a stunningly renovated historic home & addition. There are views into the Quechee hills to the east, and a wonderful trail network that meanders around the whole property and hits the high point of the land with more spectacular views. There is a lovely barn with cupola, a pond, and a sophisticated private swimming pool. The interiors are immediately comfortable and perfectly laid out. The great room connects to an artisan brick patio with pergola, and to a magnificent screened in porch that is perched over a running bro
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$1,800,000 82.9 acres 4 Beds | 4 Baths | 3832 sqft
299 Grassy Lane, Woodstock, VT 05091 - Windsor County

82.9 acres Woodstock, VT

HONEY HILL FARM- Simply one of the nicer estates in Woodstock. This is the quintessential Vermont Country Home. Only five minutes from Woodstock Village in the prestigious Prosper Hill area. There are 82 splendid acres with a stunningly renovated historic home & addition. There are views into the Quechee hills to the east, and a wonderful trail network that meanders around the whole property and hits the high point of the land with more spectacular views. There is a lovely barn with cupola, a pond, and a sophisticated private swimming pool. The interiors are immediately comfortable and perfectly laid out. The great room connects to an artisan brick patio with pergola, and to a magnificent screened in porch that is perched over a running bro
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$1,549,000 2.19 acres 4 Beds | 5 Baths | 3123 sqft
17 Mountain Ave, Woodstock, VT 05091 - Windsor County

2.19 acres Woodstock, VT

It has been written that Woodstock, Vermont is prettiest small town in America. In keeping with its charm, history and appeal is this classic village cape located on the north side of bucolic Mountain Ave. With a white picket fence, extensive gardens, substantial yard and timeless taste both inside and out, this 4-bedroom 5-bathroom home is a rare and exceptional Woodstock offering. Bordered by town forest with views to the top of Mt. Tom, 17 Mountain Avenue is walking distance to all that the village has to offer yet is private and peaceful on 2.19 acres. For those who seek comfort and class surrounded by beauty and community with direct access to nature and village amenities, this property is a perfect fit. Broker related to seller.
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$1,395,000 45 acres 6 Beds | 4 Baths | 6900 sqft
747 Grove Hill, Woodstock, VT 05091 - Windsor County

45 acres Woodstock, VT

Three miles up in the hills above the village of Woodstock, at the end of a private road, Maplecrest Farm, situated at the edge of a vast high meadow, commands spectacular views to the north and to the west where the Green Mountains & Killington Mountain dominate the horizon. The property also has trail connections to GMHA in South Woodstock. The main, 4-bedroom house makes extraordinary use of towering windows to showcase the abundant flora, fauna, and magnificent sunsets. In addition to the organic garden, heirloom apple orchard, and infrared sauna, there are two delightful cottages with full kitchens for guests, in-laws or rental income. Since 1994, the woodlands have been managed as a successful maple sugaring operation. If maple sugari
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$1,250,000 21 acres 4 Beds | 4 Baths | 3582 sqft
340 Spruce Way, Woodstock, VT 05091 - Windsor County

21 acres Woodstock, VT

Set in complete privacy on a quiet hilltop on 21+/- acres just outside Woodstock village, this thoughtfully designed and beautifully constructed 2003, 4-bedroom 3,582- square-foot home captures the lovely views of the hills and valleys all the way to Mount Cardigan. The design also takes full advantage of the progression of light from mornings in the east-facing kitchen and screen porch to afternoons in the cozy family room and western deck. The floor plan expands to provide separable space for guests or open accommodation for small children, with additional expansion area on the walk-out ground floor. The house and grounds are beautifully done, yet simple to maintain. The land provides opportunity for horses and plenty of room to play in a
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$985,000 78.42 acres 3 Beds | 4 Baths | 4167 sqft
125 Hoadley Rd, Woodstock, VT 05091 - Windsor County

78.42 acres Woodstock, VT

In a superb location, this custom-built timber frame home is situated on 78 acres protected by conservation easements, and takes advantage of privacy & quiet. Overflowing spring-fed pond and year round brook with splendid solar exposure. LR/DR/kitchen all open to each other, providing an excellent space for entertaining and great access to four different decks opening to the pond, the brook, and attractive perennial plantings. Large gourmet kitchen opens to dining/living areas. Main level BR with bath en suite, a 2nd level MBR suite with bright sitting room overlooking pond, and lower level finished with BR area, full bath and kitchenette. This is a one-owner residence, built in 1989, is ready for the next owner to update with your own pers
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$699,000 5.21 acres 4 Beds | 4 Baths | 3349 sqft
492 Westerdale Road, Woodstock, VT 05091 - Windsor County

5.21 acres Woodstock, VT

This exciting property offers 4 bedrooms, 3.5 baths, and is a scant 3 miles to Woodstock village and minutes to skiing. There is a two stall horse barn with fenced pasture on this 5.2 acre level lot with power, water, and insulated tack room abutting riding/walking trails. This home features easy transitions between indoor and outdoor spaces and is perfect for entertaining: a screened lounge, country porch, patios and decks surround an in-ground pool. Professional landscaping has maintained the mature perennial beds. The spacious master bedroom takes full advantage of the beautiful pastoral view and has a Jacuzzi tub and walk-in closet. The generous, yet cozy, family room has a fireplace, pine floors and natural light from the many windows.
$699,000 3.38 acres 3 Beds | 3 Baths | 2196 sqft
229 Blankey Cottage Lane, Woodstock, VT 05091 - Windsor County

3.38 acres Woodstock, VT

What a View! Enjoy the amazing long distance views of Killington and the Green Mountains. The house is one level and handicap accessible. Direct entry from the attached heated two-car garage for easy access and convenience. A gourmet kitchen with plenty of storage and counter space, Center Island, and eat-in dining. Wonderful views of the Koi Pond from the living room, a beautiful stone fireplace, which is equipped with a gas insert for keeping you warm on those chilly nights; the fireplace can be converted back to wood. From the master suite you have direct access to the deck, two walk-in closets, and a walk-in shower with radiant heat. Two additional bedrooms, a full bathroom with radiant heat and Jacuzzi tub, 1/2 bath, mud room, sunroo
$699,000 3.38 acres 3 Beds | 3 Baths | 2196 sqft
229 Blankey Cottage Lane, Woodstock, VT 05091 - Windsor County

3.38 acres Woodstock, VT

Bungalow with a view! Enjoy the amazing long distance views of the Killington mountain range. The house is one level for easy access and convenience. Direct entry from the attached heated two-car garage will keep you dry. The gourmet kitchen has plenty of storage and counter space, Center Island, and eat-in dining. The living room fireplace is equipped with a gas insert for keeping you warm on those chilly nights. From the master suite you have direct access to the deck, two walk-in closets, and a walk-in shower. Two additional bedrooms, a full bathroom, 1/2 bath, and laundry room complete the main floor. On the lower walkout level youll find it partially finished with a plumbed bathroom and a large storage room for all the extras. To com
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$599,000 6.5 acres 4 Beds | 3 Baths | 2440 sqft
858 Cabot Road, Woodstock, VT 05091 - Windsor County

6.5 acres Woodstock, VT

Just minutes from the Woodstock Green, yet privately situated in the hills is this quiet, well-maintained Traditional Center Hall New England cape residence with a stunning long-range mountain view. Large open living room with beautiful woodburning fireplace and built-ins opens to pleasant deck with wonderful views.First floor also features a formal dining room, eat-in kitchen, and a den on first level.Mudroom entry with direct access to two car garage. Four bedrooms on the second floor, including the master bedroom with ensuite bath.Property features a lovely brook, gracious landscaping and abuts 174 conserved acres.Central Air throughout the house. Well maintained home, lovely long range views and easy access to the village.
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$599,000 20 acres 2 Beds | 1 Bath | 1000 sqft
281 North Barnard Road (Rte. 12) Street, Woodstock, VT 05091 - Windsor County

20 acres Woodstock, VT

Charming 2 bedroom home located within walking distance of the village of Woodstock. Situated on 20 private acres abutting the Marsh-Billings Rockefeller National Historic Park. The well maintained rooms vary in size, offering endless potential for commercial or multi-residential use and development. Ample off street parking, public restrooms and separate services.See also MLS #4510441
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$495,000 11.16 acres 3 Beds | 2 Baths | 2724 sqft
914 Deerbrook Way, Woodstock, VT 05091 - Windsor County

11.16 acres Woodstock, VT

Beautifully maintained and updated timberframe home in Deerbrook, privately situated on 11.16 acres, 10 mins to the Woodstock Green and 15 mins to the Killington Skyship. Kitchen with Jenn-Air rangetop with downdraft grill/griddle, newer stainless refrigerator and dishwasher appliances, and working island for easy workflow. Cozy and sunny morning eat-in kitchen nook; Open living/dining with exposed timberframe ceiling and large woodburning fireplace; 1st floor bedroom; Large master bedroom with deep closets; Third floor is a large space for extra beds, offices or for recreation/crafting; Large full basement for storage; Two car attached garage; Mudroom access with laundry room (newer front-loading W/D) easy access to garage and kitchen; Rec
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$465,000 6.33 acres 4 Beds | 2 Baths | 2188 sqft
60 Juniper Way, Woodstock, VT 05091 - Windsor County

6.33 acres Woodstock, VT

Four bedroom, six-acre property in convenient Woodstock, (Woodstock - One of the top 10 prettiest towns to retire). country neighborhood has ample room for projects, families, and visitors. Secluded, lush fenced-in grounds include established perennial beds and shrubs, large vegetable garden, and assorted berry bushes and fruit trees. Home includes massive center brick chimney with Vermont Castings woodstove insert and built-in brick oven grill. Beautiful exposed beams over living room and kitchen. Ample kitchen includes handsome Crown Point cabinetry, Shivakashi granite counters, and skylight. Family room with pine floor, office nook, and a functioning dark room with utility sink. Oversized, two car garage with plenty of storage, as well
$299,000 2.41 acres 5 Beds | 2 Baths | 2874 sqft
588 Kendall Road, Woodstock, VT 05071 - Windsor County

2.41 acres Woodstock, VT

In South Woodstock Vermont, just a few miles from the famed Woodstock Village and the prestigious Woodstock Country Club sits this modern, 1875 farmhouse thats been the mainstay of family vacations for many years. Used in all four seasons, this property is ready to be a year around home or just the same as it has been. There's 2.41 acres bordered on one side by a year around, babbling, high off the mountain, trout stream that can be listened to from the wrap around porch. On the other side of the property is a fabulous barn in good of shape as if it was built yesterday. The owner had used it as an antique shop and its purpose could be anything you could imagine. It is Vermont and picture perfect. The house features 5 bedrooms, 2 baths with
$219,000 10.1 acres
00 Deerbrook Way, Woodstock, VT 05091 - Windsor County

10.1 acres Woodstock, VT

10.1+/- acre lot located at Deer Brook Farms in Woodstock. Sit back on the lot and take advantage of the views of Killington or sit closer to the road for local views of the hillside, you pick and choose your build site. Located at the cul-de-sac, this lot offers privacy as well as a wonderful opportunity to design and build your own home no matter where you place your house. Situate the house southwest on the property and you will be able to enjoy distant views of Killington. One of only a few remaining undeveloped lots at Deer Brook Farms, each existing home is privately situated. Conveniently located less than 5 miles from village of Woodstock and close to Killington for those looking to hit the slopes in the winter! DSL is available in
$219,000 10.1 acres
Deerbrook Way, Woodstock, VT 05091 - Windsor County

10.1 acres Woodstock, VT

10.1+/- acre lot located at Deer Brook Farms in Woodstock. Sit back on the lot and take advantage of the views of Killington or sit closer to the road for local views of the hillside, you pick and choose your build site. Located at the cul-de-sac, this lot offers privacy as well as a wonderful opportunity to design and build your own home no matter where you place your house. Situate the house southwest on the property and you will be able to enjoy distant views of Killington. One of only a few remaining undeveloped lots at Deer Brook Farms, each existing home is privately situated. Conveniently located less than 5 miles from village of Woodstock and close to Killington for those looking to hit the slopes in the winter! DSL is available in
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$159,000 6.69 acres 2 Beds | 1 Bath | 1042 sqft
3918 Densmore Hill Road, Woodstock, VT 05091 - Windsor County

6.69 acres Woodstock, VT

An affordable 2-bedroom chalet on 6.69 acres located in Woodstock. The property is private and yet close to the village of Woodstock. This would be a good opportunity for a starter home of a vacation/ski home. The septic system was repaired last fall and is in good working order. The house needs some maintenance and updating but has great potential, and is livable in its current state.
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$159,000 6.69 acres 2 Beds | 1042 sqft
3918 Densmore Hill Road, Woodstock, VT 05091 - Windsor County

6.69 acres Woodstock, VT

An affordable 2-bedroom chalet on 6.69 acres located in Woodstock. The property is private and yet close to the village of Woodstock. This would be a good opportunity for a starter home of a vacation/ski home. The septic system was repaired last fall and is in good working order. The house needs some maintenance and updating but has great potential, and is livable in its current state.
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$135,000 2 acres 3 Beds | 2 Baths | 1844 sqft
2540 Barnard Road, Woodstock, VT 05091 - Windsor County

2 acres Woodstock, VT

PRICE REDUCTION! House and 2 acre property on two lovely brooks, close to downtown Woodstock, and near the Prosper Road National Park recreation trails. This home is looking for someone with some remodeling skills who wants to enjoy great garden areas, a wonderfully sunny porch, and a 3-4 bedroom, 2 bath classic cape. Roof is a solid standing seam with mostly old pine flooring throughout and generous space for expansion. Explore how to restore this fine Woodstock home to it's earlier glory days. Extensive land is across the brook for enjoying after you wade across on those hot summer days. The Prosper Community House is your neighbor to the north and you are just two miles to downtown Woodstock. Come take a peek it's easy to show.
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$130,000 6.69 acres
2111 Austin Road, Woodstock, VT 05091 - Windsor County

6.69 acres Woodstock, VT

Exciting 6.69 acre building lot located on on the backside of Suicide Six Ski Area and accessible to VAST trails. other amenities include cleared building envelope, installed driveway, power on site and approved 4 bedroom septic design. Quality lots like this are few and far between!
$59,000 2 acres 3 Beds | 2 Baths | 1200 sqft
132 Riverbend Way, Woodstock, VT 05091-0488 - Windsor County

2 acres Woodstock, VT

SUPER clean, well maintained home that has many extras! Corner lot with large open yard. Cathedral ceilings, new appliances, large deck with automatic awning, storage shed, ice guards, central AC, efficient windows, super affordable starter home or low maintenance retirement and vacations home. Convent location to downtown Woodstock, farmers market, theater and many more. Come take a look
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$25,000 4.6 acres
0 Carlton Hill Road, Woodstock, VT 05091 - Windsor County

4.6 acres Woodstock, VT

4.6 acre site just 2 miles from Woodstock Village. Priced to sell this property has been surveyed and has a septic sesign. Located o a town road.