Greater Woodstock Area Homes Between $500K and $1 Million

The greater Woodstock, Vermont area (including the towns of Barnard, Bridgewater, Hartland, Pomfret, Reading, West Windsor, and Woodstock) offers diverse real estate opportunities. Whether you’re looking for a historic home, a home in town near shops and galleries and all the amenities you need, a family home, a secluded getaway with lots of land, a vacation home, or investment real estate, the greater Woodstock area has plenty of choices.

Apart from beautiful homes and real estate, the greater Woodstock area of Vermont hosts some great cultural institutions and events like the Hall Art Foundation in Reading, the Woodstock Film Series, and Taste of Woodstock. Summer and winter recreation opportunities abound at Suicide 6 ski area and Mount Ascutney. For horse lovers, the Green Mountain Horse Association (GMHA) in South Woodstock has activities and events all summer long.

Greater Woodstock VT Homes for Sale

The greater Woodstock VT area could be the perfect place for a family home, a vacation retreat, rental property or investment real estate. Explore the homes below, then give Bassette Real Estate Group a call at 802-457-2244. Our agents and buyer brokers would love to help you find your perfect new home.

1799 Pomfret Road Pomfret VT 05067

Pomfret, VT1799 Pomfret Road

Price$999,995

Est. Mortgage: $/month

Active With Contract

MLS Number 4703883

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 2,736

This is the perfect location! Adjacent to South Pomfret and just 2 miles from Woodstock, this well-thought-out home offers the privacy of its own covered bridge and 48 acres-complete with swimming pond, pasture, and 40 acres of wooded, trail-covered hillside that abut the Suicide Six ski area. Ski home, directly from the slopes! This family home has 5 bedrooms and 4 baths-over 2750 square feet of very livable space-and feels much larger. The open-concept first floor contains a gracious living room and a custom kitchen, complete with cathedral ceilings, a Lacanche range, and a wood-fired pizza oven. The kitchen opens onto the spacious family room, the wide front porch, and the screened dining porch. An attached two-car garage has direct access to the full basement-incredibly convenient in winter. Thoughtfully designed, this home has 12” cellulose insulation in the walls and 20” in the ceiling. An energy-efficient propane-fired boiler provides the primary heat; a back-up generator and fiber-optic Internet ensure comfort and connectivity. The three-stall barn and four-bay equipment shed ensure ample space for a variety of pursuits. A slate-roofed cottage near the house is presently a wood shop, but would make a wonderful studio or guest cottage. In addition to being next door to Suicide Six's skiing and mountain biking, the home is within an easy drive to all of Vermont's famous recreational activities. This is the quintessential Vermont playground!

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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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20 RIVER Street Woodstock VT 05091

Woodstock, VT20 RIVER Street

Price$995,000

Est. Mortgage: $/month

MLS Number 4707913

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5

A superbly renovated FEDERAL-STYLE FARMHOUSE sited overlooking a sloping lawn fronting on a tranquil stretch of the Ottauquechee River. Viewed from River Street, the front porch retains the appearance of the long time configueration as a 'twin home', before the two sides were graciously reconnected in a return to the original design and layout. The floor plan features spacious main level rooms with Master Suite, Eat-in-Country kitchen, living-dining room a secluded study and wonderful 'river room'. The second floor offers 4 bedrooms and two mirrored bathrooms. Privately situated and tastefully landscaped with native plants and shrubs. A classic Village home within walking distance of all popular amenities and activities.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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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57 River Street Woodstock VT 05091

Woodstock, VT57 River Street

Price$995,000

Est. Mortgage: $/month

MLS Number 4791575

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,075

Beautiful Woodstock home located in the heart of the village. The backyard adjoins Mountain Ave, the most prestigious street in Woodstock. Known as "The Prettiest Small Town in America." A Rockefeller town, renowned for it's rich history. This is a renovated 1826 home. The seller has updated and finished the property in the most remarkable way. His keen sense for detail, makes this property extremely unique. This home is filled with light, creating a very happy and peaceful atmosphere, and is move in ready. If you have been dreaming about purchasing a home in Vermont, then this is the one for you. 20 minutes to Killington, Okemo and to Dartmouth hospital. Call now to view this property!!!

Listed by Dorothea Mongulla, High End Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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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4662 Cloudland Road Woodstock VT 05091

Woodstock, VT4662 Cloudland Road

Price$985,000

Est. Mortgage: $/month

MLS Number 4781136

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,452

Premier location, location, location - on Cloudland Road just up from River Road and a pleasant walk to Billings Farm and downtown Woodstock for amazing bike riding, walking, and running right out the door. Privately situated in a well-landscaped setting is this immaculately maintained newer construction 3,154 sf 3 bedroom cape with vaulted ceiling mini-great room open to lovely gourmet kitchen with custom-made cherry cabinets. A charming dining area is next to kitchen. Half bath and mudroom at entrance. 1st level MBR with ensuite bath, two bedrooms a sitting room and full bath upstairs. Partially finished basement has a workout/TV area and office. Just across the driveway from the cape is a barn-garage with two bays of garage with overhead doors, a third covered bay for vehicles and equipment, and upstairs is a 1,298 sf fully finished in-law apartment with vaulted ceiling, kitchen, bath, dining, sitting area and bedroom with ensuite bath - all with its own entrance and two-level private deck area. Property has a brook flowing through it and is well landscaped with stonewalls, a charming patio, flower gardens and a garden shed with chicken coop. Excellent mechanicals in both buildings. Beautifully maintained, privately and peacefully sited on approximately 5 acres - exceptionally located less than three mins from the Village of Woodstock. This one is all about move-in-ready, and location location location.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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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1539 Gulf Road Barnard VT 05031

Barnard, VT1539 Gulf Road

Price$950,000

Est. Mortgage: $/month

MLS Number 4694326

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 5,200

This is the perfect Vermont pastoral outdoor playground property: 84.4 acres, beautiful stone walls, and wide open lawns/birch groves which surround two massive swimming/fishing/kayaking ponds, which connect to each other via a stone waterfall right at the house. Direct access to the VAST trail for snowmobiling across Vermont to Canada. Newly built 2,900 sq. ft. fully insulated cement-floor barn-garage with multiple commercial overhead doors offers storage for 10+ motorized toys plus a large vehicle servicing workshop. The residence itself offers 5 bedrooms, 3 full baths, kitchen with wood burning fireplace and a downstairs rec/game/bunk room. Attached 2 car heated garage and private deck off the kitchen overlooks both ponds. Mechanicals include a newly installed whole house automatic generator. The property is very close to a paved road just 12 minutes to Woodstock, and 2 minutes to provisions and activities at Barnard Silver Lake / The Barnard General Store.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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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206 Meoki Way Woodstock VT 05091

Woodstock, VT206 Meoki Way

Price$929,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4799170

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,484

Wonderful, award-winning 4 BR, 4 BA newer construction VT barn house on 5.5 acres, located less than a mile from Woodstock Village Green. Winner of 3 top awards from the VT Assoc of Home Builders in 2012 including Best in Energy Efficiency, Best in Environmental Excellence, and Best Single Family Home. The Ambrose-built home is architecturally designed to maximize natural light throughout the living space. The interior decor blends reclaimed 150-year-old Vermont beams with totally modern amenities. It has large windows, eight foot doors, nine foot ceilings and an atrium open all the way to the cupola 35 feet above the first floor that floods light down through the interior spaces. A wood burning stove and first floor radiant heat keep it warm and cozy. Random width hard wood ash floors. Classic covered porch has views over a neighboring pond. The present owners did extensive renovations over the past 3 years including a new gourmet kitchen, appliances, upgraded bathrooms, and completely finished the lower level into finished living space with an additional bath. The exterior is designed for low maintenance. Extensive use of closed cell foam and blown cellulose insulation all contributed to making this a highly efficient home. Tesla vehicle charger is in place. The residence is being offered turn-key and fully furnished. All of the furnishings were purchased less than three years ago by the present owners, and are perfectly suited for the home.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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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1606 BRIDGEWATER CENTER Road Bridgewater VT 05035

MLS Number 4766474

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 4,794

Maple Lane Farm is one of the areas earliest homesteads with land used as a cornfield by a local farmer fronting on the North Branch of the Ottauquechee River. The historic 1790 Cape farmhouse and approximately 130 acres is located across the road in a cluster of historic barns and stonewalled gardens. The property rises to the height of Southgate Mountain, where a rustic cabin was built as a private retreat with sweeping views over the valley south and westerly. The warm patina of time and character remains throughout the home, which has been updated with modern mechanical systems, wiring and plumbing. The town of Bridgewater is midway between Woodstock Village, Killington and Okemo Ski areas, offering a rural experience within close proximity to popular shopping and recreational amenities.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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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1073 Bible Hill Road West Windsor VT 05037

MLS Number 4630300

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,317

Located less than 15 miles from Woodstock in the desirable Bible Hill region of West Windsor, this spectacular 1861 historic post and beam cape-style farmhouse is one of the area's finest residences. Sited on an elevated knoll to optimize a panoramic view of Mt Ascutney and down the CT River Valley, this very special period home has been lovingly stewarded and thoughtfully renovated to the highest standard achieving the perfect unification of sophistication, functionality, comfort and convenience. The seamless flow of generous spaces is ideal for entertaining and daily living. The fabulous well-appointed chef's kitchen is complete with top-quality appliances, a pantry, woodstove and casual dining area. The spacious Living Room and Dining Room each have a wood burning fireplace. The main level Grand Master Suite features a luxurious spa/wet room complete with soaking tub, glass shower, sauna, Jack and Jill walk-in closets and powder rooms and a gorgeous view from every window! Step onto the stone terrace from the heated private sun-room into the hot tub and outdoor shower. Excellent potential for a B&B, an income producing home occupation, or a small horse farm in the heart of West Windsor's trail system. Central AC, State-of-the-art mechanicals, Generator, Art Studio, Attached Greenhouse, Barn, Pasture. See attached details list for a complete description of all this very special property has to offer. Easy access to I-91, Hanover, Upper Valley, skiing and recreation.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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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362 UPPER Road Bridgewater VT 05035

Bridgewater, VT362 UPPER Road

Price$835,000

Est. Mortgage: $/month

MLS Number 4741360

  • Residential Single Family
  • Construction Existing
  • Bathroom 11
  • Bedrooms 13
  • Square Feet 6,246

Perfectly suited for either residential or commercial use, this unique property is anchored around an antique cape farmhouse built when the township was founded. In an exceptional location, close to both the historic village of Woodstock and Killington Mountain Ski Resort, and within walking distance of the Long Trail Brewpub and the Bridgewater Corners Country Store; the beautifully landscaped four acre grounds feature an in-ground swimming pool with sheltered deck overlooking the Ottaquechee River Valley. The spacious, sunny, 6,200 square feet of living space is arranged into two sections connected by an enormous commercial grade kitchen. The larger section, continuously and profitably operated as October Country Inn since 1975, has 10 bedrooms, 11 baths, two large dining/meeting /game rooms, and a spacious living room. The other section, used as the innkeepers residence, has 3 bedrooms, 1 bath, office and private living area. A large semi-finished basement houses a commercial sized pantry, laundry area, large workshop and general storage. This property could easily be used as a private home for extended family, with room to grow into a special and affordable multi-generational family compound, or continued as a turn-key opportunity to step in and take over October Country Inn's long standing, excellent four decades long reputation for outstanding hospitality to the traveling public in the tradition of New England's country inns dating back over 200 years.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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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255 Delano Road West Windsor VT 05037

West Windsor, VT255 Delano Road

Price$825,000

Est. Mortgage: $/month

MLS Number 4798734

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 2,943

Equestrians take notice! Sited on just over 42 acres one has the ability to ride for hours from the property. There is access from the home to numerous trails maintained by the Green Mountain Horse Association (GMHA). Horses can graze in the fenced in areas and there is a chute that leads to an upper pasture. The grounds are bordered by stonewalls and there is a small apple orchard with views of Mt Ascutney in the backdrop. The barn has six stalls, a tack room, water, and electric. It is located just below the mid-century modern Main House. Architecturally designed by Charles Hood Helmer, the main house is divided into entertaining and sleeping spaces. Numerous windows allow the outdoor light to stream in. The front entry way leads to a beautiful living room that has built-in bookcases, exposed beams, and a wood burning fireplace. The kitchen opens to a wonderful family room that has a raised hearth with a Jutol wood burning stove insert. On the other side of the home there are three bedrooms that are all ensuite. Over the two car garage is an open space with the potential for expansion. Located below the barn is a small Caretaker's cottage that has 2 bedrooms, living room and full bath. Come see this wonderful home set in the middle of horse country.

Listed by Daphne Lowe, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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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6790 Broad Brook Road Barnard VT 05031

Barnard, VT6790 Broad Brook Road

Price$799,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4738350

  • Residential Single Family
  • Construction New Construction
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 3,791

Wonderfully open and light Post and Beam home! South facing with pleasing hillside views in a country setting. This four-bedroom home features high posted ceilings, stone fireplace, spacious ground floor master suite with adjacent sun room, flowing living/dining room, large chef's kitchen with double ovens and a wet island, upper bedroom suite with comfortable guest rooms, separate private room above the garage for studio or an office. Additionally the large lower walkout level adds more living space. Meander the country roads to Silver Lake, Suicide Six or the villages of Woodstock, Barnard and South Royalton.

Listed by Eric Johnston, Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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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8754 Pomfret Road Pomfret VT 05053

Pomfret, VT8754 Pomfret Road

Price$795,000

Est. Mortgage: $/month

MLS Number 4785578

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 6
  • Square Feet 4,319

"MILLBROOK FARM" - Equestrian property on approx 20 areas of flat rolling terrain with the main Millbrook farmhouse plus guest house/office Millbrook itself is a classic 1805 farmhouse, 5 BRs 4 1/2 BA, thoroughly renovated and insulated in 1997; The farmhouse is directly connected to a gorgeous 30x60 1800s hay barn with hand-hewn beams, perfect for a barn party! Or other events, The barn has 10 box stalls in lower level, rubber matting, heated tackroom, grainroom and sawdust storage; The historic barn is connected to a 75x150 INDOOR RIDING RING with dust-free/metal-free rubber footing. 15 acres of level pasture and hayfields, and a very special stream (the Mill Brook) bisecting the entire property; Several run-in sheds and pole barns; A newer 20x40 heated pool with 10x40 pool-house and full patio. A second 1-BR/1BA guest house (or office) is also on the property with separate access and parking. All located on paved road for easy access to for horse trailers. Full basement with game room, this property won't disappoint! Something for everyone.

Listed by Holly Hall, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.5% last updated on Mar 26, 2020
* 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 2020 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 March 29, 2020.