Woodstock Homes with Acreage

Home with Land in Woodstock VTWoodstock, 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.  

Woodstock VT Homes with Land for Sale

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.

View all Homes for Sale in Woodstock

217 Echo Ledge Road Woodstock VT 05091

Woodstock, VT217 Echo Ledge Road

Price$3,485,000

Est. Mortgage: $/month

MLS Number 4809703

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,799

Location, style, amenities: Just west of Woodstock Village, a hip renovation of a classic white clapboard farmhouse and big red barn, on 91 acres threaded with lovely trails, meadows, pond, gardens and thoughtful set up for horses. Completely renovated in 2004 and 2007, the 1850 farmhouse has a contemporary style by award winning AIA architect Michael Ertel and the texture and attention to detail of master builder Hank Savelberg. Sensitive to the integrity of the original farmhouse, integrating all modern amenities, there is an open floor plan with walls of windows that bathe the spaces in natural light. The master suite and 2 additional bedrooms are on the second floor, as well as additional expansion space. The 3-stall barn has a wide center aisle and heat throughout, except hay area and loft. The barn includes an office with high-speed internet. The farm, once part of thousands of acres owned by the Robinson family, was eventually split up and passed down through each generation. This house was owned by Jumbo Robinson who could lift and carry 2 heavy dairy cans down the hill to be picked up by the milk truck every day--the cans are still in the little corn crib with the original cider press. The edible landscape of today includes apples, plums and pear trees. Five minutes to Woodstock Farmer's Market, near skiing, golf and other recreational activities. 2.5 hours to Boston and 4.5 hours to New York. Virtual tour of the home and the barn available.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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2574 Garvin Hill Road Woodstock VT 05091

Woodstock, VT2574 Garvin Hill Road

Price$2,700,000

Est. Mortgage: $/month

MLS Number 4804667

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 6
  • Square Feet 6,545

"GARVIN HILL GETAWAY"- Newer custom built residence (that easily sleeps 15+) on 50 acres of farm pasture fields and woods with a fabulous long-range mountain view - just minutes from Woodstock village. Designed for family gatherings and entertaining friends, the residence also lives beautifully on one level. Wonderful open floor plan with high ceilings and large-proportioned rooms. The 1,200 sf great room / gathering area combines kitchen, dining and living room areas with stone fireplace that opens to an expansive wrap-around deck with its own indoor-outdoor entertaining space - with indoor and outdoor spaces all sharing the long-range mountain view over the pasture fields. A spacious first level master bedroom suite provides for 1-level living. Excellent mechanicals. Subject to current use conservation program. An oversized 3-car garage - for all your motorized toys bikes, skis, kayaks and other outdoor gear - walks into a mud-laundry room and into the house. Minimal gardens and landscaping make for a low-maintenance, super-fun gathering house on 50 acres with big views, just minutes and easy access on public roads from Woodstock village.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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1532 Happy Valley Road Woodstock VT 05091

Woodstock, VT1532 Happy Valley Road

Price$2,600,000

Est. Mortgage: $/month

Pending

MLS Number 4760962

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 6,500

This secure Vermont retreat sits high on a hill on 55 protected acres. Architect designed, a premier builder, and built on the history and character of two fully reconstructed antique post & beam frames. Unquestionably one of the nicest homes in Woodstock. Five (5) bedrooms, four (4) bathrooms, & over 6,000 sq-ft of living space finished to an exacting level of detail. There is beautiful interior space, private guest quarters, four working fireplaces, & high-end master bathroom finishes. Soaring cathedral ceilings, a gourmet kitchen with a huge walk-in pantry, 6 burner Wolf gas range, and a large Sub-Zero refrigerator. The massive central stone fireplace, magnificent P&B frames, and old wide plank floors are quintessential Vermont architecture. The grounds have a duck pond, old stone walls, mature maple trees, a four-car garage, & an impressive 4-stall timber frame horse barn. A newer cedar shake roof & re-sided cedar shingle in 2019 complement all the modern conveniences of the 21st century - high speed internet, whole house generator, underground power. Most of the neighbor's holdings include protected land in VT Current Use. Happy Valley Road is on the exclusive easterly side of town with quick access to, and away from, the major metro hubs of Boston & New York City. Did we mention the two snowmobiles & 6-wheeled Polaris Ranger included in the sale? Enjoy snowmobile trails, wandering the estate, biking & sledding on your secure Vermont domain! Check out the house video!

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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2352 Curtis Hollow Road Woodstock VT 05091

Woodstock, VT2352 Curtis Hollow Road

Price$1,975,000

Est. Mortgage: $/month

MLS Number 4754974

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 3
  • Square Feet 5,611

Wild Berry Farm artfully expresses the soul of Vermont country living in a very private setting mid-way between Woodstock Village and the recreational activities offered year-round at Killington's ski area. David Beilman AIA designed the home in close cooperation with the owners and supervised the renovation and creation of the Craftsman style residence around the core elements of an 1812 farmhouse. The rooms are spacious and filled with sunlight cascading through windows providing ample opportunity to enjoy views of the changing seasons. A deep water swimming pond, expansive perennial, herb and vegetable gardens surround the home. The various water courses and springs support a remarkable wild berry crop that sustains a variety of wildlife. The old farmstead is now covered in northern hardwoods with a patchwork of fields and natural meadows connected by a vast network of trails for hiking, biking or horseback riding. Fiber optic and a net-metering solar array provide 21st Century cutting-edge IT in a setting intended to preserve the virtues of a quiet rural life. A wonderfully tranquil place to restore yourself.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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2039 Randall Road Woodstock VT 05091

Woodstock, VT2039 Randall Road

Price$1,575,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4822404

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,800

A hidden gem at the magical “end of the road ” this classic 1840s stone Cape was constructed by Scots craftsmen of hewn stone quarried in nearby South Woodstock. Gently rolling meadows and northern hardwoods surround the homestead which is less than four miles from the public gathering space at the Village Green in Woodstock, often called the “prettiest town in America.” The National Register of Historic Places refers to this part of Windsor County as “the stone house belt of Vermont.” There is simply nothing quite like a stone house cool in summers and snug in harsh winter storms. The well-chosen farm site spreads out across 34 acres of southerly oriented landscape shaped by generations to provide sustenance and shelter. A deep, spring-fed pond serves as a refreshing swimming spot in the summer and perfect skating rink in the winter. The property includes an assemblage of outbuildings that appear like they were placed by a master painter within a frame. Under the current three-decade plus stewardship of a well-known local architect and his family, a purity of form has been retained during periodic renovations providing 21st Century comforts and updated mechanical systems, while honoring the history and embracing the quintessential Vermont vernacular of the house and setting.

Listed by Richard Higgerson and Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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675 College Hill Road Woodstock VT 05091

Woodstock, VT675 College Hill Road

Price$1,385,000

Est. Mortgage: $/month

MLS Number 4833519

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

This newly constructed, Ambrose design/build home is privately situated on 20+ acres just a short walk to the Woodstock Village Green and includes a separate 3.5-bedroom, 1.5-bath, 1,500-square foot farmhouse/guest house (currently rented for $1,700/mo) plus an historic barn, 4-bay shed-garage and swimming pond. The beautifully crafted main residence, built in 2016, features an open floor plan main living level with high ceilings and large windows which flood the kitchen/living/dining area with natural light. The main level also enjoys a generous pantry, mudroom with adjoining laundry, bedroom and 1/2 bath (to which a shower could easily be added). Upstairs is the master bedroom featuring a walk-in closet and full bath with a clawfoot tub, shower and double vanity, and two additional bedrooms and full bath. The finished lower level offers a wonderful rec/hangout room and another full bath. The house also features rooftop solar panels and is certified for excellence in energy-efficient design and construction through Efficiency Vermont. Well-maintained and beautifully landscaped grounds with a mix of lawn, gardens, a swimming pond, and woods, all of which can be enjoyed from the comfort of the covered wraparound porch. Newer, state-approved 7-bedroom septic, and a total of 4,200 sf between both homes. This is a prime opportunity for a private spot within walking distance of all of the many amenities Woodstock Village life has to offer.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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1210 Barnard Road Woodstock VT 05091

Woodstock, VT1210 Barnard Road

Price$949,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4825156

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,952

Custom designed and built in 2003, this 3 bedroom home (4 bed septic) on 14.5 acres wows you from the get go. As you wind your way up the driveway, you are greeted by stonework, gardens and a beautiful multi tiered Brazilian IPE Deck (675 sf) that looks out over the Green Mountains and Gilbert's Hill. The contemporary house welcomes you with Granite Masonry and Vermont Slate on the front as well as on the back porch. Inside, the house is bright with an open floor plan. Off the large foyer entry is a lovely den/office with builtin shelves that connects to the extensive master bedroom suite with huge walk-in closet. On the other side of the foyer is the kitchen dining area with Granite counters and a large island. The kitchen leads to a spectacular living room with Cathedral Pine ceilings, a Granite wood burning fireplace and more mountain views. The first floor also boasts a guest bedroom with 3/4 bath, a 1/2 bath, walk-in pantry and a laundry room. Upstairs is a two room loft which includes a great hangout space and a 3rd bedroom. The basement hosts a nice sized mudroom, heated 2 car garage, and ample storage space with "finishing" potential. Less than 2 miles from Woodstock Village and just minutes to skiing, hiking, and the National Park, this location is ideal as a primary or 2nd home getaway.

Listed by Dan Noble, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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1880 Randall Road Woodstock VT 05091

Woodstock, VT1880 Randall Road

Price$885,000

Est. Mortgage: $/month

Pending

MLS Number 4825894

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,656

With New England ingenuity, this classic white farmhouse was picked up and moved to this lovely site at the end of a driveway off Randall Road and was totally renovated. Tucked on a hillside above a swimming pond that looks over the rolling hills of Woodstock, there is the potential to open the views up further. This four-bedroom, two bath farmhouse offers a comfortable place to stay, room for Zoom calls and close to the amenities of the village of Woodstock. The stone patio in back is great for summer gatherings, a two-bay detached garage has room for skis and gear and there is a tiny cabin down by the pond with a bunkbed.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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509 Darling Road Woodstock VT 05071

Woodstock, VT509 Darling Road

Price$795,000

Est. Mortgage: $/month

Pending

MLS Number 4811921

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,008

A very rare opportunity to own 60 acres of land with total privacy and majestic long range views that include Mt. Ascutney all the way to Mt. Sunapee. The land is bordered by protected land so there will be no development that will be seen from the house sites . 40 Acres are in the Current Use Program with a 2 acre house site exemption. There is a large spring fed pond accessed by a path through the woods. Darling Road is a dead end road so one is assured of a very quiet , peaceful setting . The cabin is very cozy with a large screened porch and deck. Access to Woodstock and South Woodstock are less than 15 minutes away and Skiing at Okemo and Killington are 40 minutes away. All types of sports for every season are readily available . This is truly a SPECIAL property !

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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965 Deer Brook Way Woodstock VT 05091

Woodstock, VT965 Deer Brook Way

Price$665,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4807039

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,192

House in the Sun is a perfect gem sited beautifully on 11.5 acres with spectacular long range views, a pristine pond, and forest area with trails and a stream. The cape style house is a tasteful architectural blend of classic Vermont charm and contemporary design. The open concept kitchen/living/dining area that opens to a deck is warm and inviting for gathering and entertaining while taking in the panoramic view. The main level also offers an office/den as well as a bedroom with full bath. The master bedroom suite on the second level is detailed with vaulted ceilings, exposed beams and lovely large windows that capture that view! There are two additional bedrooms and bath on the second level for family and guests. Enjoy all the seasons in Vermont swimming in the pond, exploring the stream, and hiking/snowshoeing the open field and forest paths. Private but conveniently located within minutes to dining, theatre and shopping in Woodstock Village and 15 minutes to Killington Mountain Resort.

Listed by Mary Mayhew, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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6656 South Road Woodstock VT 05071

Woodstock, VT6656 South Road

Price$599,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4756440

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,031

This classic Antique Cape style Farmhouse is located in Historic South Woodstock adjacent to the Green Mt. Horse Association, with direct access to miles of horse riding trails. Enjoy the warmth and charm of living in a classic antique VT farmhouse with the option to work from home with fiber optic, symmetrical speed internet up to 800 Mbps. There's a one bedroom In-law apartment to provide overflow accommodation, and additional income. The period detail is intact and a handsome timber frame is revealed with 9' ceilings above the spacious living-dining room. The bright, spacious country kitchen The family room/ library opens onto a broad stone terrace, lovely, established gardens and playground. Potential for economic or home business use in a separate Vermont-style building with heat, electrical service and 1/2 bath. The historic horse barn with paddocks is 'right sized' for recreational horse activity. Verdant, level fields ideal for pasturing. Perfect opportunity for a "Bed and Board" facility! 6 minutes to the Woodstock Village Green. Close proximity to skiing, hiking, biking and VAST trail system. Two and a half hours from Boston and five hours from NYC makes this property convenient for a full-time residence or a second home. Short drive to the rich cultural assets of Dartmouth College and easy access to Dartmouth Hitchcock Medical Center.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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3332 South Road Woodstock VT 05091

Woodstock, VT3332 South Road

Price$575,000

Est. Mortgage: $/month

MLS Number 4826681

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,508

FOLDING HILLS is a well maintained vintage 1960 ranch style mini farm waiting for a face lift. There are presently 2 bedrooms, however the new septic system is for 3 bedrooms. There is a 2 car attached garage, a garage door access and space for one car in the spacious basement / workshop. There are multiple out buildings for storage, animals, more cars, trucks and tractors and a heated office. There are fenced paddocks and pastures, apple trees and a field bordering the Kedron Brook. There is a fabulous HOUSE SITE to develop up on the hill behind the house. Sunny exposure, with view possibilities to the north east and the south. The road is roughed in and the septic site has perc'd. This is a unique building site halfway between South Woodstock and Woodstock Village.

Listed by Lynne Bertram, Lynne Bertram Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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 October 31, 2020.