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Woodstock VT Real Estate

Woodstock, VT is an idyllic destination for those looking to purchase real estate. From historic homes to modern condos, there are numerous options to fit any lifestyle. Located in the heart of Vermont, Woodstock offers stunning mountain views, spectacular skiing and snowboarding opportunities, and a vibrant community filled with countless activities and attractions. With easy access to key amenities such as transportation and shopping centers, Woodstock is a great place to buy real estate and begin creating your own dream home!

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353 Greene Road Woodstock VT 05071

Woodstock, VT353 Greene Road

Price$18,000,000

Est. Mortgage: $/month

MLS Number 4934539

  • Residential Single Family
  • Construction Existing
  • Square Feet 11,470
  • Bedrooms 7
  • Bathroom 10

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.

Listed by Christopher Lang of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2034 Long Hill Road Woodstock VT 05071

Woodstock, VT2034 Long Hill Road

Price$9,250,000

Est. Mortgage: $/month

MLS Number 4943673

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 8,921

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

Listed by T Story Jenks and Dia Jenks of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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587 Old River Road Woodstock VT 05091

Woodstock, VT587 Old River Road

Price$8,750,000

Est. Mortgage: $/month

MLS Number 4923048

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 6,799

Old Fitch Farm is one of New England's most extraordinary estates. This remarkable residence is sited graciously on a plateau with 1200' of frontage on the Ottauquechee River, and views to Mt Tom and Woodstock Village. The impeccably restored five-bedroom, six BA main residence, four-bedroom, 2 BA guest cottage and impressive three-story horse barn reflect Federal and Greek revival influences of architect Asher Benjamin. The stately foyer in the main residence is centered by a splendid 3-story mahogany staircase, a true testament to the tradition of quality and fine craftsmanship of the era. The formal common rooms on the main level are spacious, elegant and impeccably appointed. The kitchen is spectacular with Italian tumbled marble floors, custom Dutchmade cabinetry, exceptional appliances, and Butler's pantry with custom quartersawn-oak cabinetry. The Grand Primary Suite commands the second floor with a newly added, discreet elevator, his and hers dressing rooms, impeccably appointed bathrooms, and an office. The second level is further completed by two luxurious guest suites. The third level offers two additional guest rooms with a shared bathroom. Central AC, attached, heated three car garage. There is a spectacular hilltop riding ring with bridle paths lacing through the property. A short stroll to the shops, restaurants and galleries of Woodstock Village. Fifteen minutes to skiing. Two hours, fifteen minutes to Boston. Four and a half hours to NYC.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$4,500,000

Est. Mortgage: $/month

MLS Number 4895993

  • Residential Single Family
  • Square Feet 5,142
  • Bathroom 8
  • Bedrooms 6
  • Construction Existing

Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town's finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort and convenience. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980's, providing a Great Room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef's kitchen, all located on the main level. There is a guest suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and gardens.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2055 Church Hill Road Woodstock VT 05091

Woodstock, VT2055 Church Hill Road

Price$3,900,000

Est. Mortgage: $/month

MLS Number 4951694

  • Residential Single Family
  • Square Feet 6,403
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5

Designed in 1976 by AIA award-winning architect Lewis Davis, of the New York firm Davis Brody Bond, whose work ranged from modernist skyscrapers to the renovation of the Reading Room at the New York Public Library, High Birch's sleek white design is striking amid Vermont's green hills. Davis believed in the power of architecture to enrich life, and that ethos is evident in every aspect of this property. The drive winds through rolling meadows to elevated views: a serene sanctuary, only 2.5 miles from Woodstock village. The curving design captures the abundance of natural light flooding through the tall windows, illuminating the interior and framing the green of mountains and meadows. The multi-level design sets up intimate spaces for gathering and retreating: reading, reflection, or taking in nature. In winter, everyone can gather around the fireplace. In summer, the stone terrace is the venue for outdoor entertaining. Recent renovations by Studio Nexus brought the kitchen (a Deane design), living room, bathrooms, and offices into the 21st century, while honoring Lewis Davis' intent. The interior designer, Eric Roseff, added his sense of whimsy and delight. Raycroft Meyer Landscape Architects' designs for the outdoor spaces: perennials, a vegetable garden, and berries, complement the home's aesthetic. A pond near the house is a favorite spot for kids and dogs to swim. There is a two car attached garage, storage barn, and high speed internet. Fully furnished, move in ready.

Listed by T Story Jenks and Dia Jenks of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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318 Ebbin Lockwood Way Woodstock VT 05071

Woodstock, VT318 Ebbin Lockwood Way

Price$3,450,000

Est. Mortgage: $/month

MLS Number 4966761

  • Residential Single Family
  • Bedrooms 3
  • Square Feet 6,443
  • Construction Existing
  • Bathroom 4

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.

Listed by T Story Jenks and Dia Jenks of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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144 & 232 Town Farm Road Woodstock VT 05071

Woodstock, VT144 & 232 Town Farm Road

Price$2,500,000

Est. Mortgage: $/month

MLS Number 4937127

  • Residential Single Family
  • Bedrooms 8
  • Construction Existing
  • Square Feet 3,748
  • Bathroom 5

Sense of place - the Lewis Farm: The classic Vermont farmstead with an iconic big red barn above Green Mountain Horse Association, the Lewis Farm's 130 acres of hayfields and woodlands span the Kedron Valley hillside just outside the village of South Woodstock. The legacy of stewardship by the Lewis family started in 1940: tending the land, restoring the spectacular barn and converting its lower level to well-planned stabling, conserving the most visible 30 acres along the road, and epitomizing the sense of community and engagement that characterizes South Woodstock and GMHA. Along with the 3-bedroom brick farmhouse, riding ring, smokehouse, hilltop cabin, a light-filled 2-bedroom contemporary takes in the views, and a south-facing studio is set into the hillside. The houses and studio invite thoughtful renovation to meet the quality of the site: the woodlands, hayfields, and farm pond, threaded by trails and farm roads to high meadows with valley views. The beauty of the land, authenticity, and character distinguish this generational offering.

Listed by T Story Jenks and Dia Jenks of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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144 & 232 Town Farm Road Woodstock VT 05071

Woodstock, VT144 & 232 Town Farm Road

Price$2,500,000

Est. Mortgage: $/month

MLS Number 4969259

  • Land
  • Acreage 130.39
  • Zoning Residential

Sense of place - the Lewis Farm: The classic Vermont farmstead with an iconic big red barn above Green Mountain Horse Association, the Lewis Farm's 130 acres of hayfields and woodlands span the Kedron Valley hillside just outside the village of South Woodstock. The legacy of stewardship by the Lewis family started in 1940: tending the land, restoring the spectacular barn and converting its lower level to well-planned stabling, conserving the most visible 30 acres along the road, and epitomizing the sense of community and engagement that characterizes South Woodstock and GMHA. Along with the 3-bedroom brick farmhouse, riding ring, smokehouse, hilltop cabin, a light-filled 2-bedroom contemporary takes in the views, and a south-facing studio is set into the hillside. The houses and studio invite renovation or new construction to meet the quality of the site: the woodlands, hayfields, and farm pond, threaded by trails and farm roads to high meadows with valley views. The beauty of the land, authenticity, and character distinguish this generational offering.

Listed by T Story Jenks and Dia Jenks of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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10 College Hill Road Woodstock VT 05091

Woodstock, VT10 College Hill Road

Price$2,444,000

Est. Mortgage: $/month

MLS Number 4945641

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,214

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.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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587 College Hill Road Woodstock VT 05091

Woodstock, VT587 College Hill Road

Price$2,395,000

Est. Mortgage: $/month

Pending

MLS Number 4966586

  • Residential Single Family
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 4,163
  • Construction Existing

Absolutely incredible location on 5+ acres with fabulous long range views yet only a short 10 min walk to the Woodstock village green. This newer and beautifully maintained timberframe features an open floorplan with a large gourmet kitchen and dining that connects to the vaulted timberframe ceiling great room with woodburning fireplace. A 1st floor primary bedroom suite connects to an office. Heated, attached 2-car garage, opens to large mud-pantry-laundry area and on into the kitchen. Privately situated 1st floor powder bath off foyer. Upstairs are 3 bedrooms with vaulted-timerberframe ceilings and oversized bath. Above the garage is a fully heated and finished private office space that could easily be converted into a separate bedroom (The house is on public water and sewer). Outside the kitchen and living room is a wonderful covered porch with views. Nearby on the property is a separate 2-bay barn-garage with fully-finished and heated workshop area upstairs, which could be converted into an accessory dwelling unit apartment on the property, or kept as-is for storage of all your motorized toys and outdoor recreation items such as bikes, canoes, kayaks. The basement of the main house has a radiant-heated cement floor, high ceilings and could easily be finished into a rec/game/theatre room. Superb and modern mechanicals include radiant heat on all levels of the main house and an automatic whole-house propane backup generator. One-owner house.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2018 Church Hill Road Woodstock VT 05091

Woodstock, VT2018 Church Hill Road

Price$2,275,000

Est. Mortgage: $/month

MLS Number 4969169

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Square Feet 4,610
  • Bathroom 4

Ideally oriented south and westerly this light-filled contemporary home engages you in the outdoors through expansive windows, decks and screened porch overlooking the spring-fed swimming pond. Designed for gracious country living the eat-in kitchen and generous great room are accented by a fieldstone fireplace and vaulted ceilings. The primary bedroom suite and two guest bedrooms are located on the main living level with a walk-out level offering an additional bedroom with media and exercise areas. A 'bonus room' used as a studio is available for many alternative pursuits. Fifty acres of private woodland and open meadows is laced with trails enabling access to nature year round. A small stable is a resource to take advantage of South Woodstock's network of horse trials and miles of gravel roads. A private retreat within minutes of Woodstock's Village Green or the South Woodstock and the Green Mountain Horse Association. The best of all possible worlds.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

5798 South Road Woodstock VT 05071

Woodstock, VT5798 South Road

Price$2,250,000

Est. Mortgage: $/month

MLS Number 4968227

  • Residential Single Family
  • Square Feet 4,510
  • Bedrooms 5
  • Bathroom 7
  • Construction Existing

For nearly two centuries the iconic Kedron Valley Farm has served as the gateway to the village of South Woodstock. Prominently sited on a knoll with lovely valley views in every direction, this warm and inviting post and beam home has been fully rejuvenated, honoring the classic period detail. The main house is ideal for entertaining with bright, generous rooms, and cozy spaces. The living room runs front to back, centered by a fireplace with pine surround and exposed beams. The kitchen is well suited with Thermador appliances, quartz counters and custom mahogany cabinetry. The spacious private primary suite features exposed beams, cathedral ceiling, new tandem bathrooms connected by a walk thru shower, plenty of closet space, laundry and AC. There are four additional guest suites, a TV and reading room w fireplace and built-ins, and clever loft spaces with offices. The charming, separate three-bedroom carriage house is perfect for guests, family or as an income producing rental unit. The property is anchored by a spectacular 4-story bank barn with six horse stalls, fenced paddocks and a run-in shed complete with power and water. The grounds are gorgeous with a beautiful brick terrace, level verdant lawns, grand, 175 year old maple trees, established perennial beds, a private swimming pond, apple orchard, and a fenced har-tru surfaced tennis court sited discreetly at the rear of the property. Seven minutes to Woodstock Village Green. Broker interest.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity 

Copyright 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated October 4, 2023 3:55 PM EDT