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.

1606 BRIDGEWATER CENTER Road Bridgewater VT 05035
Active With Contract

MLS Number 4766474

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 6,120

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: 3.04% last updated on Apr 15, 2021
* 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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9295 Pomfret Road Pomfret VT 05053

Pomfret, VT9295 Pomfret Road

Price$944,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4829953

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,584

Own a historic 1809 schoolhouse that has grown into a custom-designed country home. The living room is accented with new hickory floors, plenty of windows, and a brick fireplace with a woodstove. The spacious country kitchen features cathedral ceilings, antique beams, large windows, a grand center butcher block island, and wood cookstove. The ground floor ensuite bedroom boasts a bathroom with a large jetted tile tub, walk-in shower, sauna, and radiant heat. The cozy artistic dining room is wonderfully decored with a life-size chess board mural, and track lighting to set the mood. Relax in the family room with its fireplace, a great place to study, or retreat. The unique upper-level bedrooms are centered around a charming play space and Dutch doors to the individual bedrooms. This home's far side offers two more bedroom spaces and a screened porch to relax and view the heated pool, gardens, and barn. This pool is heated, the yard is fenced, and a barn with storage, room for animals, and an open second-floor recreation space ample for a studio, fitness center, or even indoor basketball. The extensive garden space has an active asparagus patch, raised beds, berry bushes, and plenty of tillable space to grow your choice vegetables. This Home is nestled high above the road on a knoll and is located conveniently within minutes of the Upper Valley and pleasantly accessible to Pomfret/Woodstock. You'll be pleasantly welcomed on your visit of this property and all it has to offer.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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3575 Route 106 Reading VT 05062

Reading, VT3575 Route 106

Price$895,000

Est. Mortgage: $/month

MLS Number 4855055

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 5,800

ESCAPING TO VERMONT! Charming restored 1794 - 4 bedrooms (en-suite)/5.5 bath, 5,500+/-sqft, antique oversized Cape, high-speed Fiber-optic, indoor heated saltwater pool (40x20), 2 car garage, 5 working fireplaces, attached 2 story post & beam barn, & fabulous Recreation room. Character and history fill this home with wide pine & hardwood floors, exposed hand-hewn beams, 5 Rumford fireplaces, and all the conveniences of 21st century living. Fabulous modern kitchen with commercial gas Garland 6 burner double-oven range/griddle for the master chef. Plenty of soapstone counterspace for prep work, an efficient pantry, & lovely views of a nicely landscaped & fenced back yard. The kitchen eating area is perfect for intimate meals and the gracious dining room lends an opportunity to host more formal dinner parties. Add to this a "killer rec room" in the barn, a home office, an extra family room & study, a gracious living room, and a fabulous steam/shower & private exercise room with the Master Bedroom. Practicals? Extra wood boiler 2011, 60% of roofs redone 2011-2015, foam insulation in basement 2017, a new 2019 whole house high efficiency propane boiler that keeps the home warm & cozy. Beautiful old maples frame the house, lots of level yard for play & garden, fire pit, & your choice of two brooks to relax by. Less than 15 minutes to Woodstock and there is a great AirBnB opportunity in this former B&B. Ideal spot for the outdoor enthusiast for hiking, biking, skiing, & snowmobiling.

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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3759 Royalton Turnpike Barnard VT 05031

Barnard, VT3759 Royalton Turnpike

Price$895,000

Est. Mortgage: $/month

MLS Number 4856192

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 3,316

True to form. True to history. The deep-rooted story behind the "recreation" of this classic Vermont hill farm begins with a ca. 1815 center chimney Cape painstakingly disassembled and relocated from the shores of Novia Scotia to the current position in the funky country enclave of Barnard, Vermont. Original whitewashed wood ceilings, mantles, moldings, and hardware have all been retained. The residence features a classic design with a massive center chimney with four working masonry fireplaces and a Vermont Castings wood stove in the kitchen's eat-in area. The gourmet kitchen is equipped with a La Cornue dual fuel range and an expansive walk-in pantry. The full bath on this level has been well-incorporated within the house's original footprint and is located in such a way as to make the addition of a first-floor full bath relatively easy. The 25 acres of Vermont countryside include dramatic long-range views up the valley, prime agriculture soils, open pastures, a naturalist's and wildlife fan's paradise, extensive wetlands, and three different beaver ponds. Completing the property is a dramatic and spaciously proportioned three-story post and beam bank barn with ample storage and access via a sturdy quay from the Turnpike and a ca. 1790 English frame-scribe-ruled hay barn. The property is located a short distance from the world-renowned Twin Farms Resort & Spa, known today as one of the Nation's finest luxury resorts, Silver Lake, Woodstock, and Suicide 6

Listed by Richard Higgerson, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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738 Stage Road Pomfret VT 05067

Pomfret, VT738 Stage Road

Price$850,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4843827

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 4,309

Located on the old stagecoach road 4 miles north of the Woodstock Village Green, this 1780's expanded post and beam cape is a wealth of antique charm, character and history. Lovingly stewarded over centuries honoring the period detail, including original hand hewn beams, wide plank floors, solid oak walls and five fireplaces. The spacious country kitchen has an impressive walk-in fireplace with a pellet stove. The spacious, attached, antique carriage barn with cathedral ceiling is the perfect "great room" to entertain large gatherings. Relax on the spectacular "summer porch" connecting the main house to the barn complete with a wood stove and heat lamps overlooking The Barnard Brook, which laces through the grounds providing a tranquil background sound, and a cool escape on a summer day. There is a separate apartment/office over the barn. The property is an exceptional opportunity for a family compound, with a bucolic mix of level ground, verdant rolling hills, and wooded land with an impressive inventory of hardwoods and trails. Perfectly suited for horses, livestock, extensive gardening, and so much more. There are ancient apple trees, mature lilacs, copious, established perennial beds that run along the brook. The property abuts The Appalachian Trail park to the north and east for hiking and recreation. Walking distance to Suicide Six, Teago Store and PO, The Grange Theater and The Artistree. Abutting 3 AC parcel available.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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898 Barnard Road Woodstock VT 05091

Woodstock, VT898 Barnard Road

Price$849,000

Est. Mortgage: $/month

MLS Number 4843539

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,608

Prime location in Woodstock. Located a minute to Woodstock Village and Marsh-Billings-Rockefeller National Park. First time offered since 1975. Circa 1771 "Hillside" is a special property on over 31+ acres with beautiful views everywhere you look. The sprawling 5 bedroom/ 4 bath Farmhouse is the perfect place to entertain family and friends. The home has a mudroom/pantry that leads you into a large eat in kitchen. Walk out to the screened porch to sit back and enjoy your morning coffee and soak in the sweet views. The main level of the home has the original hand hewn wood beams and consists of a formal dining room, living room with wood burning fireplace, cozy library with hearth and fireplace, first floor guest room, and full bath with clawfoot tub. Take the main staircase to the second level where you will find a spacious primary bedroom suite, and two more bedrooms one which is being used as an office currently. The third level has a guest bedroom, hangout room and bathroom. The home has a spacious floor plan with the option to turn one area back to an in law suite. As you head outside you will enjoy the very private backyard with stone patio and gazebo. Stroll down to the 3 level barn and let your imagination fly. The barn is 3 barns that were merged together. This could be a great place to have a home business, artist studio or renovate it as extra recreation or sleeping space. Close to Suicide Six. Schedule a tour of this Woodstock property today. It will not last.

Listed by Marni Rieger, KW Vermont-Killington

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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
  • Bedrooms 13
  • Bathroom 11
  • 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: 3.04% last updated on Apr 15, 2021
* 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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628 Deer Brook Way Woodstock VT 05091

Woodstock, VT628 Deer Brook Way

Price$825,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4855582

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 3,817

Listed by Daphne Lowe, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 Linden Hill Woodstock VT 05091

Woodstock, VT5 Linden Hill

Price$799,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4852550

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 9
  • Bathroom 7

Well located, in a favorite neighborhood of Woodstock Village, is offered an antique 1850's home that is tastefully converted into 4 high quality residential units! The central largest residence (9 rooms, 4 bedrooms, 3 1/2 baths) occupies 3 levels of the original house. This residence benefits from graceful rooms with generous proportions. Fine interior finishes and high quality detailing include hardwood flooring, custom built cabinetry, central air conditioning and luxury fixtures. On the ground level is a living room with wood burning fireplace and built in book shelving, an entry foyer, a dining room with chandelier and a kitchen with attached laundry. On the second level is a sitting room that is flanked on either side by bedrooms with ensuite baths. A third level presents 2 additional bedrooms and a full bath. Apartments on either side of the main residence (one apartment has 7 rooms, 2 bedrooms, 1 bathroom; the other apartment has 3 rooms, 1 bedroom, 1 bathroom) have interconnected passage with the main residence to allow substantial quarters of three discrete spaces for family or friends, or the passages may be closed off for independent use. A fourth apartment (4 rooms, 2 bedrooms, 1 bathroom) has a separate entry off terraced private lawns in the rear. Each of the 4 apartments has a private entry, a complete kitchen, and each has a wood burning fireplace. A flexible floor plan presenting the opportunity for several generations to comfortably coexist with privacy!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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2317 North Road Barnard VT 05031

Barnard, VT2317 North Road

Price$795,000

Est. Mortgage: $/month

MLS Number 4850716

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 3,224

Hy-Wynds Farm is a classic Vermont homestead on the desirable North Road in Barnard. The home has been carefully upgraded to contemporary luxury standards while retaining elements of historic charm and style. The mountain views, sunrises and sunsets are sublime! The first floor includes a gourmet kitchen with soapstone countertops and kitchen island, formal dining room, den/study and a Great Room with stone fireplace. Off the kitchen is a full bathroom, plus a large combination laundry/pantry with built-in desk showing sweeping pastoral views from the oversized window. Upstairs are 3 bedrooms and full bath plus sitting area. A huge mudroom connects the home to the 2-car attached garage. The property is further enriched by a large post and beam studio/workshop, so bring your imagination. The extensive gardens and animal barn with photovoltaics (net positive electric bill) lend themselves to a fully sustainable lifestyle. The current owners spent much effort enhancing the perennial beds, including an extensive array of Schreiner iris, David Austin roses and sweet peas from Floret Farm! The berry patch includes thornless Dorothy Thompson red raspberries, three kinds of currants & gooseberries. Other treasures are asparagus, rhubarb, and herb garden. You won't want to leave, but if you must, the farm is centrally located about half way between the quaint village of Woodstock and the convenience of I89. Glimmering Silver Lake and the Barnard General Store are a mere 2 miles away.

Listed by Susan Hickey, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 42nd Street Hartland VT 05048

Hartland, VT5 42nd Street

Price$765,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4812140

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 3,632

Well maintained and impressive antique colonial with accessory income earning dwellings situated on 41+ acres. The home is grand and gracious and has been well kept over the past 100 years. The main house has a large country kitchen with plenty of cupboards for storage and counter-tops for prep work, there is a quaint breakfast nook, a formal dining room, and spacious living room to host family and friends. Two large enclosed porches add to the available space for hosting as well as a lovely stone porch and a pergola covered deck. The location would be great for a home occupation and is directly off the Windsor Hartland Exit 9 off of Interstate 91. Live in the 5 bedroom/2.5 bath main house and offset your mortgage by receiving approximately $4,100/mnth rent from the accompanying 3 apartments and 2 mobile homes. The majority of the 41 acres is behind a hill, down a town road, and would support additional development. There is a very large barn on the property that can support a large trailer or heavy equipment, additional rental space, or workshop space, and excellent road frontage on RT 5 will support a thriving business if desired.

Listed by Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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46 Wemple Knoll Road Bridgewater VT 05035

Bridgewater, VT46 Wemple Knoll Road

Price$759,000

Est. Mortgage: $/month

MLS Number 4855263

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,426

Perched high on a hilltop this bright , light-filled custom designed home enjoys dramatic mountain views . The open spaces create an easy flow for entertaining and comfortable lifestyle. Enjoy gathering around the stone fireplace on cool winter evenings and entertaining on the wrap around deck on warm summer days. There is a 6 person hot tub in a lovely wood paneled room off of the kitchen. The grounds are generous with plenty of spaces for gardens and play areas. There is a year round stream running along the property. The solar panel system provides a hot water system to supplement the domestic hot water . 10Kw, grid-tied solar electric array (split between roof mount and pole mount panels ) ensures low electric bills. There are 3 Mitsubishi heat pumps that provide air conditioning through out the house. Also the house has a gas fired full house generator for the infrequent times of power outage . There is high speed fiber optic network for internet, cable television , landline and cell phone service . Only minutes away from world class skiing at Killington and Okemo. Less than 20 minutes from the historic village of Woodstock and all of its amenities. There is additional acreages available upon request. Please no drive bys

Listed by Daphne Lowe and Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 2021 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 April 18, 2021.