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Single Family Homes for Sale in Vermont

Scroll down to browse single family homes for sale in the Woodstock region of Vermont. Contact Williamson Group Sotheby’s International Realty if you have any questions or if you would like to schedule a time to visit a home. Create an account to save your favorite homes and to receive email notifications when similar listings become available. 

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
  • Bathroom 6
  • Bedrooms 5
  • Construction Existing
  • Square Feet 5,412

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: 6.29% last updated on Sep 22, 2022
* 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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290 Hanover Center Road Hanover NH 03755

Hanover, NH290 Hanover Center Road

Price$8,387,500

Est. Mortgage: $/month

MLS Number 4917483

  • Residential Single Family
  • Bathroom 6
  • Construction Existing
  • Bedrooms 5
  • Square Feet 11,881

Greystone is one of the region's finest examples of American Shingle Style architecture and one of only a handful of truly world-class homes in Hanover, New Hampshire. Conveniently located within 15 minutes of Dartmouth College and only six miles to downtown Hanover, the property takes full advantage of the privacy and panoramic southerly views afforded by the finely landscaped 13-acre parcel. Established gardens, extensive stonework, and beautiful outdoor spaces distinguish the design. Employing natural wood finishes, generous porches, and asymmetrical structural features to integrate with the natural surroundings, it takes advantage of light, views, and breezes. The multiple levels of the home feature a dramatic central stairwell that culminates in a rooftop observation deck. The five bedrooms, four full and two half baths as well as a perfectly executed guest suite and bunk room combine with both formal and informal gathering spaces that include a magnificent great room, handsomely appointed home offices, a home theater, family rooms, and a workshop. The roughly 12,000+/- square feet of interiors executed at the highest level of fit and finish always feels as inviting and as intimate as the Inglenook that connects the dining area to the main foyer. A covered breezeway attaches the main house to an oversize, three-car studio/garage with a finished heated second floor with a barrel-vaulted ceiling, a full bath, and currently, a large in-home gym.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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159 Howard Road New London NH 03257

New London, NH159 Howard Road

Price$7,500,000

Est. Mortgage: $/month

Pending

MLS Number 4917001

  • Residential Single Family
  • Bedrooms 9
  • Construction Existing
  • Bathroom 4
  • Square Feet 5,716

Sought after, very special Lake Sunapee property, set on 8.9 +/- private acres with 412.5 feet of west facing shoreline. Enjoy your summer days on one of the finest sandy beaches, with sandy bottom swimming for all ages. Boaters in the family will love the expansive dock that has room for multiple boats. Take in the panoramic views, including both Herrick Cove lighthouse and Loon Island lighthouse. Property includes a beach house with changing rooms and ample space for equipment and beach toys. The stately 8- bedroom main house is set up off the water, overlooking the lake and beach. It features beautiful hardwood floors, 4 wood burning fireplaces, spacious walk-in pantry, a game room with views from your windows seats and so much more. Spend Summer evenings dining on the large screened porch as you watch the magnificent sunset, then proceed back down to the water for a swim and campfire on the beach. Plenty of room for guests including a quaint guest house just steps away boasts its own screen porch. The carriage house offers parking for cars and a golf cart, a shop, and game-room and office space upstairs. The playhouse offers an additional retreat. Don't miss out on this rare opportunity on beautiful Lake Sunapee!

Listed by Jessica Dolan and Anthony Dolan of Dolan Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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1583 Westerdale Road Woodstock VT 05091

Woodstock, VT1583 Westerdale Road

Price$7,495,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4913355

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Square Feet 8,225
  • Bathroom 8

SUGAREE - Incomparably situated at the peak of Woodstock's fabled Western Dale, this exceptional residence is nothing short of superb. Built with the finest materials and an exquisite eye for detail, the six-bedroom, eight-bathroom home overlooks the Green Mountains with a breathtaking southern view. The thirty-acre landholding comprises open meadows, forests, miles of John Morton trails, and a gorgeous swimming pool. Splendidly private and tranquil, but just ten minutes from Woodstock village, the house was comprehensively transformed in 2016 by the area's finest craftsmen with custom and trade-only finishes and fixtures. Fully automated with high-speed internet and strong cell reception, the house lends itself beautifully to full or part-time enjoyment. Well appointed to accommodate friends and family with ease, this home is being sold fully furnished and poised for the next adventure - from the Simon Pearce flatware to the Shackleton Thomas bedroom suite to the Polaris gator. A delight in every season, Sugaree is simply one of Vermont's finest properties.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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249 Bragg Hill Norwich VT 05055

Norwich, VT249 Bragg Hill

Price$6,000,000

Est. Mortgage: $/month

MLS Number 4883128

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 9
  • Square Feet 9,621

Huge views, big land, near everything: Hard to imagine that a nearly 200 acre hilltop estate is within walking distance of the village of Norwich. With the scale, sweeping views to the White Mountains, complete privacy and presence of one of the great Vermont country properties, Highlander is just over a mile to Dan & Whit's and the green. The home and barns are built on the site of an old hilltop farm with massive sugar maples, stone walls, hayfields, managed woodlands, and ponds for swimming and wildlife. The home is elegant and comfortable with an indoor/outdoor flow. Relax and take in the views on the patios and porches or supper in the summer room, which opens out to the pool. At the heart of the house is the capacious, recently renovated, kitchen. Extensive perennial gardens unfold throughout the summer, & an edible landscape yields apples, pears, peaches & berries. An active, outdoorsy family shaped the character of Highlander. Many sets were played on the tennis court and active equestrians grew from ponies to top-flight competitors in the roomy 6 stall stable and on the trails. Kids learned hard work bringing in the hay. The swimming pond converts to pond hockey in the winter, & the other 3 ponds host diverse wildlife all year round. The family hosted an annual cider pressing, skied on the trails & raced on sleds down the long meadows. 2 bedroom apartment over 4 bay equipment barn. Easy access to AT trail.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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266 Allis State Park Road Brookfield VT 05060

MLS Number 4926292

  • Residential Single Family
  • Bedrooms 6
  • Construction Existing
  • Bathroom 5
  • Square Feet 6,089

Exquisite privacy. On a hillside. Within a park. At a meadow's edge. Casual luxury. Wide open sun-filled living spaces. Expansive yet intimate. The biggest, broadest, deepest, and most far-ranging views. 7 peaks and a jewel-like lake. Gorgeous materials palette coupled with rock-solid detailing. 6 generous bedrooms with 5 suites on 3 levels. An irresistible gravity compels friends and family to come for new adventures, raucous celebrations, and quiet refuge. Everyone returns from the farmer's market and epic hike to create a feast and gather by the fire. Raging snowstorm and powder-day dreams come true. Welcoming cozy warmth. Wood, stone, and vast expanses of glass in superb composition. Painterly framed views. Essentially brand new. Definitely best-of-the-best. Fine-grained Douglas-Fir, stainless and raw steel, honed granite, and glass. Thoughtful layout and perfect flow. All surrounded by 625 acres of parklands. And just 3 miles to the village, 8 to Northfield, and 18 to Montpelier. Heated 3-car garage. Post and beam barn. Original 100-year old stone smokehouse, fireplaces and chimneys. Upper and lower level laundries. Toasty German ceramic tile floors. Triple-glazed fenestration. A forever standing seam metal roof. Media/hang-out/billiards space with a fully-equipped bar. Clouds Hill. Experience this magic. Escape and come home to this oasis.

Listed by Geoffrey Wolcott of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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5 Gates Road Hanover NH 03750

Hanover, NH5 Gates Road

Price$4,950,000

Est. Mortgage: $/month

MLS Number 4928064

  • Residential Single Family
  • Village Etna
  • Bedrooms 8
  • Square Feet 14,073
  • Construction Existing

Designed and constructed with the highest standards, no attention to detail spared, commercial mechanicals and electrical set the tone for this stunning opportunity. The kitchen is adorned with Wolf Range and warming drawers, two Sub-Zero refrigerators, floor to ceiling cabinetry, and a hand laid mosaic marble floor. The open concept kitchen/dining creates a entertaining space for large gatherings with access to the outdoor decks. Two bedrooms with mountain views serve as a private enclave for the owners suite and complete with outdoor space. The lower level presents opportunities for an indoor pool, hot tub, spa, fitness facility, and an unrivaled entertainment experience in this one-of-a-kind home. This once imagined dream is ripe for the next owner to create a multi-generational compound.

Listed by Marco Day and Lochrane Gary of BHHS Verani Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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
  • Construction Existing
  • Bedrooms 6
  • Bathroom 8
  • Square Feet 5,142

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: 6.29% last updated on Sep 22, 2022
* 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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3 Church Street Woodstock VT 05091

Woodstock, VT3 Church Street

Price$4,250,000

Est. Mortgage: $/month

MLS Number 4917788

  • Residential Single Family
  • Construction Existing
  • Bedrooms 10
  • Bathroom 15
  • Square Feet 10,206

A handsome Federal Greek Revival built in 1831 by Joel Eaton, Three Church Street is at the heart of the picturesque village of Woodstock, voted the most beautiful town in America by Conde Nast Traveler. The house is rumored to have been a stop on the Underground Railroad and local lore has it that General Lafayette slept here. The east wing was added in the 1860s and was a recovery home for civil war veterans. Set on just under two acres with 249 feet on the Ottauquechee River, the exquisitely renovated house has maintained its historical integrity while adding modern amenities such as en-suite bedrooms and air conditioning. The two-acre property has been meticulously maintained and is in exceptional, move-in condition. It comes completely furnished and includes an in-law apartment and guest apartment. An expansive porch looks out over a private back lawn that gently slopes down to the river with views of Mt. Tom. The outdoor areas have a sense of space with the added pleasures of perennial gardens, a heated pool and fire pit. Head out the front door and walk to locavore eateries, theatre, the weekly summer farmer's market on the Green, shops and the Marsh-Billings-Rockefeller Historic Park with 20 miles of trails to explore on foot, by horse or snowshoes. A day of skiing at Suicide Six or Killington or gravel bike riding on the scenic dirt roads are all close by. Come home. Breathe. Relax. Rock on the porch. Cozy up by the fire. Shown by appt only with 24 hour notice

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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298 Holiday Farm Road Bridgewater VT 05035

Bridgewater, VT298 Holiday Farm Road

Price$3,950,000

Est. Mortgage: $/month

MLS Number 4929847

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3,757

The legacy property of OQ Farm (formerly known as the Holiday Farm) has been adapted several times throughout its historical past, most recently as a 481-acre short-term hospitality and retreat destination with an arts and spiritual focus. Featuring 8 different dwelling structures, OQ Farm offers a diverse range of accommodation options, from 1800s historic, a luxurious lodge retreat center, to sleek and modern eco-cottages, converted maple sugar shack, a studio cabin and caretaker's cabin, all taking advantage of unique views of the river valley and mountain range beyond. Boasting 1,200+ feet of river frontage along the North Branch and Ottauquechee Rivers, which flows into the Connecticut River; OQ Farm is situated equidistant between the Appalachian Trail and ski slopes of Killington and the quaint town of Woodstock - renowned as one of America's most beautiful towns. Several fenced pastures and barns provide for agricultural use beyond the sheep, alpacas, poultry and horses present currently. An extensive network of mountain biking, hiking and snowshoeing trails, and a large bonfire pit offer endless outdoor recreation and gathering opportunities.

Listed by Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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486 Benedict Road Woodstock VT 05071

Woodstock, VT486 Benedict Road

Price$3,750,000

Est. Mortgage: $/month

MLS Number 4925674

  • Residential Single Family
  • Bathroom 7
  • Square Feet 6,040
  • Construction Existing
  • Bedrooms 6

"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. 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. SHOWINGS WILL START SUNDAY AUGUST 21.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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301 VT Rte 12 Randolph VT 05060

Randolph, VT301 VT Rte 12

Price$3,700,000

Est. Mortgage: $/month

MLS Number 4929071

  • Residential Single Family
  • Square Feet 2,542
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

Ayers Brook Goat Dairy is a premiere farm located on some of the best farmland in Vermont and just minutes from downtown Randolph and I-89. Currently, they milk over 200 CAE-free goats and are raising 200 replacement doelings and breeding bucks. Ayers Brook has invested heavily in Saanen genetics over the years, importing from the top breeders worldwide. With facilities that can accommodate 600+ milkers year round, barns for young stock, and a beautiful, historic farmhouse on site, this farm is poised to become one of the largest goat dairies in the Northeast. Ayers Brook Goat Dairy presents a unique opportunity for dairy farmers in an expanding sector of agriculture. With ten years of trial and error behind them and European genetics that are found only at Ayers Brook, the farm is ready for new ownership and ready for expansion. Offerings like this are scarce, and any successful dairy farmer would be entering the playing field with a considerable head start. Main barn and milking facility: 27734 sq. ft., with poured slab and double 20 parlor, expandable to double 30.Yearling barn: 4263 sq. ft. with hayloft above Kidding barn: 3638 sq. ft. with elevated and heated feed floor Equipment Shed: 2332 sq. ft Compost Hoop Barn: 3200 sq. ft. with slab Commodity Shed: 576 sq. ft with slab and raised roof for dump trailer clearance Solar arrays: 174kWh Residence: 2500 sq. ft. 4 Bed/ 2 Bath brick farmhouse with 2 BR Farm Labor Apartment on 3rd floor

Listed by Kevin Channell of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 2022
* 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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Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. 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 September 27, 2022 3:54 PM EDT.