South Woodstock, VT Homes for Sale

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  /54

  $2,599,000

  • 9 Beds
  • 11 Baths
  • 5,993 Sq Ft

  41 Pleasant St, Woodstock, VT 05091

  This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with

  

  Jennifer Falvey

  KW Vermont Woodstock

  41 Pleasant St, Woodstock, VT 05091
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  /32

  $975,000

  $220K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,592 Sq Ft

  26 Mount Peg Rd Unit A, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit A, Woodstock, VT 05091
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  /31

  $875,000

  $120K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,584 Sq Ft

  26 Mount Peg Rd Unit B, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit B, Woodstock, VT 05091
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  /60

  $2,500,000

  • 4 Beds
  • 3.5 Baths
  • 5,127 Sq Ft

  114 Oak Ridge Way, Woodstock, VT 05091

  See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen—complete with a Sub-Zero

  Tami Sullivan Snyder Donegan Real Estate Group

  114 Oak Ridge Way, Woodstock, VT 05091
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  /59

  $3,500,000

  • 5 Beds
  • 4.5 Baths
  • 6,170 Sq Ft

  56 Cream Pot Rd, Hartland, VT 05048

  CREAMPOT FARM- Idyllic country estate with easy access to Woodstock Village. Set on 104+ acres, this pristine property offers private groomed trails, beautifully landscaped grounds, multiple ponds, and stunning southerly views toward Mount Ascutney. From the moment you enter the gated drive and wind through stone walls, there is an immediate sense of peace and privacy. Originally built by G.R.

  David Donegan Snyder Donegan Real Estate Group

  56 Cream Pot Rd, Hartland, VT 05048
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  /28

  $875,000

  $120K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,584 Sq Ft

  26 Mount Peg Rd Unit C, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit C, Woodstock, VT 05091
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  /33

  $1,895,000

  • 2 Beds
  • 2.5 Baths
  • 2,944 Sq Ft

  2394 Fletcher Hill Rd, Woodstock, VT 05091

  Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is

  John Snyder Snyder Donegan Real Estate Group

  2394 Fletcher Hill Rd, Woodstock, VT 05091
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  /31

  $975,000

  $220K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,385 Sq Ft

  26 Mount Peg Rd Unit D, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit D, Woodstock, VT 05091
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  /4

  $169,000

  • Land
  • 15.4 Acres
  • $10,974 per Acre

  0 Iver Johnson Way Unit 5095630, Woodstock, VT 05091

  Instant equity in Woodstock! Bring your vision to life on this exceptional parcel of raw land, nestled in one of Vermont’s most coveted and quintessential communities. Offered below its current town-assessed value and backed by a recent independent appraisal valuation, this property delivers significant instant equity from day one. Whether you envision a private, tucked-away country estate or a

  Chelsea Bevis KW Vermont Woodstock

  0 Iver Johnson Way Unit 5095630, Woodstock, VT 05091
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  /60

  $2,495,000

  • 3 Beds
  • 1.5 Baths
  • 2,476 Sq Ft

  232 Town Farm Hill Rd, Hartland, VT 05048

  The property is located on Town Farm Hill Rd, one of the most beautiful ridgeline Vermont roads with long range mountain views to the east and south. At certain times of the day the lighting brings out the true meaning of “purple mountain majesty”. Over the years the seller has acquired multiple parcels to create this beautiful sanctuary setting. The house is positioned to take in the mountain

  Terry Davis Williamson Group Sothebys Intl. Realty

  232 Town Farm Hill Rd, Hartland, VT 05048
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  /56

  $675,000

  • 2 Beds
  • 2 Baths
  • 1,536 Sq Ft

  793 Blood Hill Rd, West Windsor, VT 05089

  An efficient 2-bedroom chalet located in the foot hills of West Windsor. Over the years the sellers have completed a total gut renovation of the interior and exterior of the house. New windows, doors, hardwood flooring, built-ins, remodeled bathrooms and kitchen are just few upgrades to this charming home. A 2-car garage was added with a large heated bonus room above, which can be used as a

  Terry Davis Williamson Group Sothebys Intl. Realty

  793 Blood Hill Rd, West Windsor, VT 05089
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  /55

  $1,395,000

  • 4 Beds
  • 3 Baths
  • 3,306 Sq Ft

  2033 South Rd, Woodstock, VT 05091

  Historic character, beautifully reimagined for modern Vermont living.Minutes from Woodstock Village, this extensively renovated four-bedroom home pairs the warmth and authenticity of its 150-year-old wide-pine floors and exposed beams with a remarkable collection of recent improvements.At the heart of the home is a brand-new, high-end kitchen with Bosch appliances and newly installed

  Keri Cole Williamson Group Sothebys Intl. Realty

  2033 South Rd, Woodstock, VT 05091
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  /56

  $2,300,000

  • 5 Beds
  • 6 Baths
  • 3,489 Sq Ft

  915 Peterkin Hill Rd, South Woodstock, VT 05071

  Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5 bedroom, 4 bathroom extended cape styled home was renovated approx 15 years ago with handsome hardwood floors throughout. Large kitchen with Calcutta Marble, Electrolux stainless appliances and ample storage that opens into the dining room- The formal

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  915 Peterkin Hill Rd, South Woodstock, VT 05071
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  /33

  $774,000

  $25K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,004 Sq Ft

  1326 Curtis Hollow Rd, Woodstock, VT 05091

  If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends,

  Mandolyn McIntyre Crow Real Broker LLC

  1326 Curtis Hollow Rd, Woodstock, VT 05091
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  /28

  $395,000

  • Land
  • 8 Acres
  • $49,375 per Acre

  0 Vermont 106, South Woodstock, VT 05071

  Rare opportunity to own 8 +/- acres of land in South Woodstock Village with easy access off of Rt. 106. This parcel is being divided off of a 10.87 acre lot. There is a wonderful , open site ideal for building your dream home offering privacy , trails and a short walk to the South Woodstock Country Store, Kedron Valley Inn , dining at the Ransom Tavern and a swim in the Kedron pond ! 5 miles into

  Carol Wood Williamson Group Sothebys Intl. Realty

  0 Vermont 106, South Woodstock, VT 05071
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  /22

  $799,999

  $5K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  3036 W Woodstock Rd, Woodstock, VT 05091

  On a small hill, amongst trees and beautiful gardens, sits this beautifully maintained log cabin with sweeping views of the surrounding mountains and river valley. Just a short drive outside of Woodstock Village, this cabin offers the perfect blend of privacy and convenience. Built in 1996, this thoughtfully crafted home features approximately 2,600 square feet of living space on 2.9 acres. The

  Jennifer Kirkman KW Vermont Woodstock

  3036 W Woodstock Rd, Woodstock, VT 05091
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  /57

  $449,000

  • 3 Beds
  • 1 Bath
  • 1,242 Sq Ft

  23 Biscuit Hollow Rd, Woodstock, VT 05091

  This nicely updated ranch on a country acre is a rare opportunity to live in Woodstock without breaking the bank. Perfect for downsizing, one-level living, starting out, or even an easy-to-care for vacation home. There is plenty of storage for skis or other recreation equipment in the oversized two-plus car garage and two bay shed with a concrete floor. Sellers have spent 12 years gradually

  Tambrey Vutech KW Vermont Woodstock

  23 Biscuit Hollow Rd, Woodstock, VT 05091
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  /55

  $3,975,000

  • 4 Beds
  • 6.5 Baths
  • 6,450 Sq Ft

  4777 Rush Meadow Rd, West Windsor, VT 05089

  Sheep Run Farm takes its name from the stone-walled lanes where a prosperous 19th-century farmer once moved his sheep between the barn and upper meadows. Nearly two centuries later, those walls still trace the landscape, framing a beautifully reimagined Vermont farmstead on 21± acres in West Windsor, 3 miles from South Woodstock and 8 miles from Woodstock Village.Drawing on the

  Dia Jenks LandVest, Inc/Woodstock

  4777 Rush Meadow Rd, West Windsor, VT 05089
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  /33

  $695,000

  $55K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,285 Sq Ft

  47 Pleasant St, Woodstock, VT 05091

  Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living space), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used

  John Snyder Snyder Donegan Real Estate Group

  47 Pleasant St, Woodstock, VT 05091
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  /45

  $595,000

  $100K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,288 Sq Ft

  11 Maple St, Woodstock, VT 05091

  A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently

  John Wetmore Wetmore Real Estate

  11 Maple St, Woodstock, VT 05091
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  /38

  $1,325,000

  • 2 Beds
  • 1.5 Baths
  • 1,817 Sq Ft

  171 Delano Rd, Reading, VT 05062

  Constructed in 2025, and located in the desirable Rush Meadow region of West Windsor, this impeccably orchestrated Yankee Barn Post and Beam home features superb materials, old world craftsmanship and detailed fit and finish. Custom milled cabinetry and built-ins throughout. The rooms are filled with natural light with stunning bucolic views from every window. The home is centered by a dramatic

  Danny Kogut Williamson Group Sothebys Intl. Realty

  171 Delano Rd, Reading, VT 05062
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  /31

  $646,500

  • Land
  • 37.85 Acres
  • $17,081 per Acre

  0 South Rd, Woodstock, VT 05071

  Country land at the south end of Woodstock reaching from RT 106 to the top of the ridge. Potential for views with clearing at several levels. Trails through the property with access to the GMHA network. Stonewalls and a stream.About two miles to GMHA and South Woodstock village, one mile to VAST trail.40 minutes to skiing at Killington, less to Okemos. About 20 minutes to Ascutney

  Matthew Spittle Vermont Horse Country Real Estate

  0 South Rd, Woodstock, VT 05071
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  /24

  $452,600

  • 2,915 Sq Ft

  282 Skunk Hollow Rd, Hartland, VT 05048

  Two buildings on one parcel in desirable Hartland, Vermont! This flexible and well-maintained property includes a single-family home and a duplex, offering outstanding potential for owner occupancy, multi-generational living, or investment income. Ideally situated just 25 minutes from Hanover, NH, and 10 minutes from Woodstock, VT, this location provides the perfect balance of convenience and

  Loren Wehmeyer Tesla Realty Group, LLC

  282 Skunk Hollow Rd, Hartland, VT 05048
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  /28

  $475,000

  • 2 Beds
  • 1 Bath
  • 2,304 Sq Ft

  1958 Rush Meadow Rd, West Windsor, VT 05089

  This unique one-of-a-kind property will inspire your creativity. "The Silo House" is located on a tranquil, private lot in the desirable Rush Meadow region of West Windsor with frontage on the Willow Brook and rear access to the local trail system. There are two bedrooms, a LR/DR combination and a large shaded deck overlooking the brook. Perfect for full time living, or a great second home

  Danny Kogut Williamson Group Sothebys Intl. Realty

  1958 Rush Meadow Rd, West Windsor, VT 05089
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  /19

  $479,000

  $100K PRICE DROP

  • Land
  • 60.57 Acres
  • $7,908 per Acre

  0 Noah Wood Rd, Woodstock, VT 05071

  Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower

  Dan Noble Snyder Donegan Real Estate Group

  0 Noah Wood Rd, Woodstock, VT 05071
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  /58

  $2,950,000

  • 8 Beds
  • 8 Baths
  • 6,200 Sq Ft

  5798 South Rd, Woodstock, VT 05071

  Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx 32 acres. This stunning extended antique post and beam cape is complete with a large traditional 4 story barn with 6 horse stables and equipment sheds offers everything one could wish for in a country property. The grounds include gracious old maples, beautiful

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  5798 South Rd, Woodstock, VT 05071
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  /54

  $1,600,000

  • 3 Beds
  • 3.5 Baths
  • 3,294 Sq Ft

  39 Elm St Unit B, Woodstock, VT 05091

  The Richmond House Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a proud brick Federal distinguished by its softly weathered rose-hued patina and refined architectural detail. Set on more than an acre behind a classic white picket fence and thoughtfully reimagined under the direction of Laurence Rockefeller, the property comprises three

  Derek Cosentino Four Seasons Sotheby's Int'l Realty

  39 Elm St Unit B, Woodstock, VT 05091
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  /60

  $525,000

  $70K PRICE DROP

  • Land
  • 20.2 Acres
  • $25,990 per Acre

  00 Long Hill Rd, Woodstock, VT 05071

  Discover the perfect blend of privacy and convenience with this exceptional 20.2-acre parcel, combining two lots into one remarkable opportunity. Featuring a 50 foot right-of-way for access, this wooded retreat offers multiple prime building sites. With selective clearing, you can take in breathtaking views in your choice of direction; east, south, north, or west. Located just minutes from South

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  00 Long Hill Rd, Woodstock, VT 05071
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  /29

  $5,875,000

  • 3 Beds
  • 3.5 Baths
  • 5,384 Sq Ft

  115 Eastman Rd, Woodstock, VT 05091

  Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's most desirable locations: a place where life slows and the beauty of the Vermont countryside takes center stage. At the end of a quiet road, the property combines sweeping mountain views, and exceptional privacy with a thoughtfully designed hand-crafted, timber frame

  Story Jenks LandVest, Inc/Woodstock

  115 Eastman Rd, Woodstock, VT 05091
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  /60

  $1,195,000

  $180K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,979 Sq Ft

  16 Church St, Woodstock, VT 05091

  This wonderful Vermont Cape-style home is a peaceful hideaway with amazing views upriver towards Killington is within walking distance of Village shops, restaurants, and resort amenities. The home has overlooked the Ottauquechee River and the former Woodstock woolen mill since 1890. The old mill has long since been repurposed as a children’s daycare center surrounded by community pools,

  Laird Bradley Williamson Group Sothebys Intl. Realty

  16 Church St, Woodstock, VT 05091
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  /54

  $950,000

  • 1,757 Sq Ft

  1956 Rush Meadow Rd, West Windsor, VT 05089

  Rare opportunity to own one of the most unique compound properties in West Windsor. "The Dome" and The "Silo House" share a lovely 13.9 AC secluded and tranquil parcel fronting the Willow Brook in the desirable Rush Meadow region of West Windsor with rear access to the extensive local trail system.Beautiful established gardens, and mature plantings. Excellent rental investment potential. Both

  Danny Kogut Williamson Group Sothebys Intl. Realty

  1956 Rush Meadow Rd, West Windsor, VT 05089
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  /59

  $14,900,000

  $3M PRICE DROP

  • 7 Beds
  • 10 Baths
  • 12,520 Sq Ft

  355 Greene Rd, Woodstock, VT 05071

  Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and

  Chris Lang

  355 Greene Rd, Woodstock, VT 05071
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  /32

  $400,000

  • 2 Beds
  • 1 Bath
  • 1,324 Sq Ft

  2556 Church Hill Rd, Wood Stock, VT 05091

  Once an old school house, this home features stone walls, beautiful gardens, and a nice level yard with a stone patio. The year-round brook cascades over rocks and winds along the back side of the property. A covered porch leads inside, where the main floor offers an eat-in kitchen, a large living room and a dining area with French doors to the outside. There are also two bedrooms, an office with

  Dan Noble Snyder Donegan Real Estate Group

  2556 Church Hill Rd, Wood Stock, VT 05091
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  /19

  $345,000

  • Land
  • 6.48 Acres
  • $53,241 per Acre

  0 Oakridge Way, Woodstock, VT 05091

  Your dream home starts right here — with a blank canvas in one of Vermont's most coveted communities. This exceptional buildable lot on Oak Ridge Way presents a rare opportunity to design and construct your ideal residence on a quiet side road in Woodstock. Nestled within a highly sought-after neighborhood, surrounded by million dollar homes, this property offers the kind of setting that inspires

  Nancy Greenwood Watson Realty & Associates

  0 Oakridge Way, Woodstock, VT 05091
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  /7

  $325,000

  • Land
  • 8 Acres
  • $40,625 per Acre

  1 Carlton Hill Rd, Woodstock, VT 05091

  Sweet Spot - 8 acre building lot located within minutes of the Woodstock Village Green! Driveway is in place and a lovely building site has been cleared and power is at site. Wonderful opportunity to build your Vermont getaway or primary residence. Enjoy access to four season recreation, Marsh-Billings-Rockefeller National Park, theatre, arts, dining, shopping and a short commute to all

  Mary Mayhew Snyder Donegan Real Estate Group

  1 Carlton Hill Rd, Woodstock, VT 05091
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  /14

  $845,000

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  234 Randall Rd, Wood Stock, VT 05091

  Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm

  Wade Treadway Wade I Treadway Real Estate

  234 Randall Rd, Wood Stock, VT 05091
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  /17

  $275,000

  • 3 Beds
  • 1 Bath
  • 903 Sq Ft

  5556 W Woodstock Rd, Wood Stock, VT 05091

  Nestled in the highly desirable Woodstock area, this property offers the perfect canvas for your vision. Featuring an older mobile home and a spacious barn, the possibilities are there for those looking to create a country retreat, hobby farm, workshop space, or future building site.The barn provides valuable storage or recreational use, while the existing mobile home offers a starting

  Daniel Preston KW Vermont Woodstock

  5556 W Woodstock Rd, Wood Stock, VT 05091
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  /52

  $5,950,000

  New Construction $1M PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 5,087 Sq Ft

  412 Skyland Ln, Woodstock, VT 05091

  Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg.Found at the end of a quiet lane, sweeping vistas of the Green Mountains and

  Story Jenks LandVest, Inc/Woodstock

  412 Skyland Ln, Woodstock, VT 05091
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  /47

  $349,000

  $90K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,617 Sq Ft

  5798 W Woodstock Rd, Woodstock, VT 05091

  Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors

  Carol Wood Williamson Group Sothebys Intl. Realty

  5798 W Woodstock Rd, Woodstock, VT 05091
• 

  

  /26

  $450,000

  $45K PRICE DROP

  • 2 Beds
  • 3 Baths
  • 2,091 Sq Ft

  85 Townhouse Way Unit 14, Woodstock, VT 05091

  Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! This unit is in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  85 Townhouse Way Unit 14, Woodstock, VT 05091

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