Woodstock Homes with Acreage

Woodstock, Vermont is often cited as one of the prettiest towns in America. Owning a home on a large-acre lot is your chance to own a part of this quintessential Vermont town.

Woodstock real estate provides residents with the opportunity to stroll the pedestrian downtown, visit galleries, and partake in a variety of outdoor activities like biking, hiking, skiing, fishing, and golfing. After an active day, dine at one of the town's many renown restaurants. You can catch first-run movies at Pentangle Arts, a concert at nearby Dartmouth College’s Hopkins Center for the Arts, or a play at White River Junction’s Northern Stage.

With a home on a large-acreage parcel, you can keep horses and other livestock, build a garden to your specifications, have pasture or woods. Much of the real estate sited on 10+ acres in Woodstock also has excellent long-range views of the surrounding mountains.  

Find your perfect Woodstock, VT home with a lot of acreage below or contact Bassette Real Estate. One of our experienced brokers or buyer agents will be happy to help you.

Woodstock, VT 05091

Price$5,450,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4720968

  • Residential Single Family
  • Listing Agent Name Christopher Lang
  • Construction Existing
  • Bathroom 8
  • Bedrooms 6

Located at the end of a private road in Woodstock, Vermont on a hilltop with long range views of the Green Mountains, is a stunning six-bedroom eight-bathroom residence that is exceptional in every detail. First is the land itself, 30.39 +/- acres that fold over the ridge on either side with fields, woodlands and miles of John Morton trails for fitness and recreation. At the height of the land is the home. Private and secluded, all you hear are the sounds of nature, and as you look out over the landscaped yard and swimming pool to the cascading ridges and mountains beyond, Feng Shui is omnipresent. It was the land - its views, privacy and serenity - that drew the owners to the property eight years ago and for good reason. Parcels like this are exceptionally hard to find let alone buy. Which explains why after using the property for several years the owners decided to completely remodel and expand the circa 2008 home. Finished in 2016, the transformation is extraordinary inside and out. Everything is top of the line with custom and trade-only finishes and fixtures throughout. The house is also fully automated and has high-speed Comcast Internet and great cell-phone reception. Using an iPad, you can control temperature, lights, speakers, shades, alarms and security cameras, onsite or remotely via the Internet. Simply put, this is one of the nicest offerings in Northern New England; a perfect house on a perfect parcel in a perfect location.

Listed by Christopher Lang, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.85% last updated on Oct 18, 2018
* 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 A VisitAsk A QuestionMore Details

153 Ribbett Way, Woodstock, VT 05091

Price$695,000

Est. Mortgage: $/month

MLS Number 4719234

  • Residential Single Family
  • Listing Agent Name Keri Cole
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4

Wonderful Private Retreat - Minutes from Woodstock Village! Sunny and magical, this Ken Mackenzie-designed four-bedroom home enjoys southerly views across open meadows, a spring-fed swimming pond, and year-round stream. Well situated on 16 acres, the three-level main house offers stunning custom-cut cherry floors, a marble and stainless kitchen with gourmet appliances, and gorgeously updated bathrooms - making this home a joy for living and entertaining. An expansive deck brings the outdoors in, and open-concept living spaces are made cozy with reclaimed architectural elements, a specially commissioned Barbara Kaufman ceramic hearth, and artisanal built-in cabinetry. Owned by the same family for 38 years, this Woodstock property will delight you with its tranquil end-of-road privacy and enchanting architecture.

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.85% last updated on Oct 18, 2018
* 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 A VisitAsk A QuestionMore Details

2 Carlton Hill Road, Woodstock, VT 05091

Price$995,000

Est. Mortgage: $/month

MLS Number 4717944

  • Residential Single Family
  • Listing Agent Name John Bassette
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3

Own the fabulous Carlton Reservoir as your own swimming, fishing, and boating pond. Fantastic location with additional building lot for boat house, guest house, artist studio, or caretakers house. Beautiful stone walls, flat level building lot, and awesome zipline on approximately 10 acres of land and pond. Just around the corner is the fully renovated 3 bedroom/2.5 bath 3,165 sq. ft. contemporary cape with an additional finished 864 sq. ft. private media room for "wide screen TV movie nights". The house sits on an additional 13.75 acres. There is over 4,800 sq. ft. of heated space for living and home projects! The house enjoys magnificent views of rolling meadows and the hills of Marsh Billings Rockefeller National Park. There is a newly built GeoBarn with a custom workshop and private media room with high end finishes in both flooring and extra touches. We even have a tree house for the "kid". There is a spacious three car garage close to the home & lovely landscaped grounds make this home a beautiful place to escape from the hustle and bustle of life. An excellent opportunity to develop a family compound, vacation retreat, or handsome estate. Own you own little corner of heaven! Four minutes to WUHS, seven to downtown Woodstock, and 20 minutes to Killington. An ideal location for family or a vacation retreat. For full details on the home or to purchase the home with a smaller piece of land (without the pond), see MLS #4717399 at 76 Grove Hill Road, Woodstock.

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.85% last updated on Oct 18, 2018
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

76 Grove Hill Road, Woodstock, VT 05091

Price$755,000

Est. Mortgage: $/month

MLS Number 4717399

  • Residential Single Family
  • Listing Agent Name John Bassette
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3

DESIRABLE NEIGHBORHOOD! Fully renovated 3 bedroom/2.5 bath 3,165 sq ft contemporary cape with an additional finished 864 sq ft private media room for "wide screen TV movie nights". There is over 4,800 sqft of heated space for living and home projects! The house enjoys magnificent views of rolling meadows and the hills of Marsh Billings Rockefeller National Park. There is a newly built GeoBarn with a custom workshop and private media room with high end finishes in both flooring and extra touches. There are numerous home living spaces (Craft Room, (2) Family Rooms, Living Room, Media Room, Office, & Dining Room). The modern 2004 kitchen renovation has plenty of cupboards for storage and there are newer 2013 Kitchen Aid appliances. There is a private master bedroom suite with built-in double closets, air conditioning, and a newly redone tiled master bath. Two additional bedrooms with hardwood floors share a common bath. The large family room has a gracious fireplace (and woodstove) to stay warm and cozy during those cold winter months. Lovely private porch and patio can accommodate large gatherings to enjoy the views as you eat a relaxing meal. We even have a tree house for the "kid". There is a spacious three car garage close to the home & lovely landscaped grounds make this home a beautiful place to retreat from the hustle and bustle of life. Four minutes to WUHS, seven to downtown Woodstock, and 20 minutes to Killington. An ideal location for family or a vacation retreat.

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.85% last updated on Oct 18, 2018
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

343 Spruce Way, Woodstock, VT 05091

Price$1,250,000

Est. Mortgage: $/month

MLS Number 4710997

  • Residential Single Family
  • Listing Agent Name Danny Kogut
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4

This is one that you absolutely have to see! Pictures simply cannot capture the warmth, functionality and tranquility of this very special property. Located on a private dead-end road in the Cox District region of Woodstock just 8 minutes from the Village Green. The pristine long-range views can be appreciated from every room. Every inch of this lovely post and beam cape has been tastefully renovated to the highest standard with new chef's kitchen, bathrooms, systems, solar and generator. Each of the four bedrooms has it's own private bathroom. Lovely screened porch and deck overlooking stone walls, perennial beds and the view beyond. Brand new barn with separate farm road entrance, open pasture and a magnificent interior trail system. Walk out lower level with family room, office and guest accommodation. Spacious, private heated room above the attached three car garage for studio, recreation room or for home occupation. Excellent equine potential.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.85% last updated on Oct 18, 2018
* 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 A VisitAsk A QuestionMore Details

6656 South Road, Woodstock, VT 05071

Price$699,000

Est. Mortgage: $/month

MLS Number 4704059

  • Residential Single Family
  • Listing Agent Name Gretchjen Smith
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4

This pre-Civil War farmstead is located on the southerly side of South Woodstock across from the Green Mt. Horse Association and with access to miles of horse riding trails. This property offers very good potential for economic or home business use in a separate Vermont-style building with heat, electrical service and 1/2 bath. A handsome timber frame is revealed with 9' ceilings above the spacious living-dining room. The country kitchen is an ideal place for friends and family to gather and enjoy a morning meal. The combination family room and library opens onto a broad patio, gardens and playground. Fiber optic cable access expands the possibilities to include IT endeavors and other enterprises requiring the ultimate in high-speed internet connectivity. The historic horse barn with paddocks is 'right sized' for recreational horse activity. Verdant, level fields and forested land enrolled in Current Use invite traditional Vermont pursuits. The homestead includes a guest apartment periodically rented and additional 'possibility' spaces for income and creative uses.

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.85% last updated on Oct 18, 2018
* 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 A VisitAsk A QuestionMore Details

1096 Prosper Road, Woodstock, VT 05091

Price$1,495,000

Est. Mortgage: $/month

MLS Number 4699235

  • Residential Single Family
  • Listing Agent Name John Snyder
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3

Fabulous private timberframe residence on 34.29 acres with long-range south-facing views and direct walking access to the Marsh-Billings-Rockefeller National Park, which abuts to the east. The residence was completed in 2005 and boasts an oak timberframe and reclaimed barnboard floors. The great room has vaulted ceilings, two fireplaces, looks out at the long-range view and opens to the gourmet kitchen, beyond which is the mudroom and powder bath. With a four-bedroom septic in place, the house is currently designed as a three-bedroom residence, with each bedroom having an ensuite bath. Wonderful south-facing covered porch, side screen porch and detached 2-car garage. All expected modern mechanicals including backup generator, radiant heat throughout (except MBR), a fire sprinkler system, security system. Totally privately situation yet easy access - just 2 minutes to the Woodstock Farmers Market, 5 mins to Woodstock Green and 20 mins to the Killington Skyship.

Listed by John Snyder and Andrew Holson, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.85% last updated on Oct 18, 2018
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

1018 Deerbrook Way, Woodstock, VT 05091

Price$1,595,000

Est. Mortgage: $/month

Pending

MLS Number 4694036

  • Residential Single Family
  • Listing Agent Name John Snyder
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4

1018 Deerbrook Way offers the perfect Vermont getaway with end-of-road privacy on 26 +/- acres, a FABULOUS long-range mountain view overlooking the swimming pond, and a beautifully constructed and well-maintained getaway residence. Constructed in 2009 with substantial recent upgrades including kitchen renovation, upgraded insulation, Hunter Douglas window treatments, new generator and more. All the amenities you are seeking in a second home - including an open floor plan, gourmet kitchen that opens to a vaulted ceiling great room with stone fireplace and exceptional views! Two pairs of french doors open from the great room out to the expansive south and west facing wrap-around deck that looks out over the pond to the long-range mountain views. First level master bedroom, three other bedrooms, three full baths and one half bath. The downstairs was recently fully renovated into a hang-out den/rec/TV/game room plus other spaces for workout equipment, and painting/writing studios/office space. Mechanicals include a two-car attached, heated garage, whole-house UNICO AC/heating system, full automatic backup generator and high-speed fiber optic internet - so you can get away but be fully wired when required. The property is located at the top/end of a private road and is just 15 minutes to Killington and 8 minutes to the Woodstock Green - so very easy access. This house is quite simply the perfect turnkey Vermont getaway house that has it all!

Listed by John Snyder and Andrew Holson, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.85% last updated on Oct 18, 2018
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

326 Hall Circle, Woodstock, VT 05091

Price$689,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4691364

  • Residential Single Family
  • Listing Agent Name Laird Bradley
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4

Privately sited and superbly maintained, this timber-framed New England style home offers incredible southerly views over the Ottauquechee River Valley. You can enjoy watching the lights of Woodstock Village a mile distant from every room. The home was constructed by one the areas finest post and beam builders using traditional mortise and tenon joinery on display throughout. Spacious common areas all open onto patios and decks on each level of the residence. Generously sized bedrooms and well-appointed baths provide private space for family and guests. This wonderful and quiet country setting is just minutes from restaurants, recreation offerings at Suicide Six Ski area, Woodstock's Golf Course, Athletic Club and all resort amenities.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.85% last updated on Oct 18, 2018
* 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 A VisitAsk A QuestionMore Details

914 Deerbrook Way, Woodstock, VT 05091

Price$499,500

Est. Mortgage: $/month

MLS Number 4689416

  • Residential Single Family
  • Listing Agent Name Mary Mayhew
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3

Beautifully maintained and updated timberframe home in Deerbrook, privately situated on 11.16 acres, 10 mins to the Woodstock Green and 15 mins to the Killington Skyship. Kitchen with Jenn-Air rangetop with downdraft grill/griddle, newer stainless refrigerator and dishwasher appliances, and working island for easy workflow. Cozy and sunny morning eat-in kitchen nook; Open living/dining with exposed timberframe ceiling and large woodburning fireplace; 1st floor bedroom; Large master bedroom with deep closets; Third floor is a large space for extra beds, offices or for recreation/crafting; Large full basement for storage; Two car attached garage; Mudroom access with laundry room (newer front-loading W/D) easy access to garage and kitchen; Recently replaced/upgraded roof, well-pump, fridge, dishwasher, washer-dryer, french doors, skylight windows - it's move in ready! Naturalized landscaping, lovely gardens, and wonderful deck for outdoor entertaining!

Listed by Mary Mayhew, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.85% last updated on Oct 18, 2018
* 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 A VisitAsk A QuestionMore Details

486 Benedict Road, Woodstock, VT 05071

Price$1,645,000

Est. Mortgage: $/month

MLS Number 4675093

  • Residential Single Family
  • Listing Agent Name Terry Davis
  • Construction Existing
  • Bathroom 7
  • Bedrooms 6

“Spring Hill Farm” located in the heart of Vermont's equestrian region. The renowned Green Mountain Horse Association and all the events are just up the road. This amazing property offers a 3,040 sq. ft. vintage 1820 stone cape, which has been elegantly restored while keeping the authentic charm and architectural beauty. The gourmet kitchen has stainless steal appliances, brick flooring, and pantry, along with a fireplace keeping a true country feeling. The formal dining room walls have hand painted murals, and the large gathering room, perfect for entertaining, has vaulted ceilings with hand- hewn beams and built-ins. The house is set up with 4 bedrooms, 5 bathrooms, along with 5 wood burning fireplaces. The views of the barns and pastures can be had from most every room. Included is a 3,000 sq. ft. reclaimed barn of the same era that has been beautifully restored serving as a 3-bedroom guesthouse. The guest barn has a 2 story stone fireplace, wide pine floors, full kitchen, and a generous loft with a ¾ bathroom. On the lower lever are 2 additional bedrooms, a full bathroom, and a recreational room. To complete the package is a 5-stall barn with multiple fenced pastures. With over 6,000 sq. ft. of living space there is plenty of privacy for everyone. A truly idyllic piece of Vermont! The town office has the house listed as a 3 bedroom and the guest barn as a 2 bedroom; currently the house is set up with 4 sleeping areas and 3 in the guest barn.

Listed by Terry Davis, Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.85% last updated on Oct 18, 2018
* 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 A VisitAsk A QuestionMore Details

2304 Barnard Road, Woodstock, VT 05091

Price$699,000

Est. Mortgage: $/month

MLS Number 4674671

  • Residential Single Family
  • Listing Agent Name John Snyder
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5

Set high on a south-facing hillside just 4 mins from the historic Town Green in Woodstock, Vermont and close to the site of the first rope tow and the cradle of alpine skiing in North America, this property offers every amenity that one could want for the Vermont country lifestyle. The 2002 Colonial features an expansive farmer's porch overlooking the valley towards MarshBillingsRockefeller National Park, a 50-foot long mahogany deck with hot tub, an open first floor plan with a cook's kitchen accented by quality appliances and granite counter tops, four bedrooms and a detached and legally permitted one BR guest/in-law apartment with kitchen, bath and sitting room. There are two additional buildings for all of your cars, snowmobiles, boats or other motorized toys and vehicles: a larger 55' x 60' garage with 14 foot ceilings with attached 12' by 60' shed-bay, and a 2 car lower garage-workshop. Sited for privacy on 23 magnificent acres with full southern exposure and views.

Listed by John Snyder and Andrew Holson, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.85% last updated on Oct 18, 2018
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Broker Reciprocity

Copyright 2018 Northern 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. Subject to errors, omissions, prior sale, change or withdrawal without notice. This web site is updated daily.