Homes for Sale in 05091

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  /60

  $950,000

  • 3 Beds
  • 3 Baths
  • 2,794 Sq Ft

  34 Midsomer Meadows Ln, Woodstock, VT 05091

  Welcome to Starry Hill, a fully furnished and somewhat recent Airbnb rental. Handcrafted, solid-timber Colonial privately nestled on 18.9 tranquil acres just 5 miles North of Woodstock, built over 4 years by a family of loggers and master craftsmen. This exceptional home features Eastern white pine walls, hemlock structural beams, and pine ceilings/flooring sourced from the property. Warm,

  John Bassette Bassette Real Estate Group

  34 Midsomer Meadows Ln, Woodstock, VT 05091
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  /26

  $3,300,000

  • 3 Beds
  • 4.5 Baths
  • 3,682 Sq Ft

  249 Sawyer Rd, Woodstock, VT 05091

  Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary

  Andrew Bustin LandVest, Inc/Woodstock

  249 Sawyer Rd, Woodstock, VT 05091
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  /60

  $799,000

  • 7 Beds
  • 7 Baths
  • 4,581 Sq Ft

  7137 US Route 4, Bridgewater, VT 05034

  Welcome to the historic Bridgewater Inn — a rare, turn-key Vermont property perfectly positioned between Woodstock Village, Killington Resort, and Okemo Mountain. This unique offering features a spacious 3-bedroom, 3-bath main home along with four fully equipped guest suites, creating exceptional flexibility for full-time living, multi-generational use, or continued short-term rental success. The

  Benjamin Cote EXP Realty

  7137 US Route 4, Bridgewater, VT 05034
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  /60

  $1,300,000

  • 4 Beds
  • 5 Baths
  • 3,195 Sq Ft

  125 Shurtleff Ln, Woodstock, VT 05091

  Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for everyday living and entertaining, the main level features an open, light-filled layout, a well-appointed kitchen, and seamless access to a sunny three-season room overlooking the landscaped grounds. The sought-after first-floor

  Keri Cole Williamson Group Sothebys Intl. Realty

  125 Shurtleff Ln, Woodstock, VT 05091
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  /60

  $230,000

  • 1 Bed
  • 1 Bath
  • 856 Sq Ft

  42 Heritage Condo Way Unit 14D, Woodstock, VT 05091

  Welcome to your Woodstock affordable retreat! This inviting, end-unit, two-level townhouse in the sought-after Heritage Condominium community is nestled on a dead-end road just minutes west of the historic village of Woodstock. This bright 856 sq/ft two-level home offers an open-concept first floor with a carpeted living/dining area warmed by Empire gas heat (plus electric backup). From this

  John Bassette Bassette Real Estate Group

  42 Heritage Condo Way Unit 14D, Woodstock, VT 05091
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  /11

  $149,000

  • Land
  • 3.54 Acres
  • $42,090 per Acre

  00 Carlton Hill Rd Unit 27, Woodstock, VT 05091

  Discover the beauty of Vermont from this diverse 3.5-acre parcel along Carlton Hill Road, set in a peaceful rural location amid a neighborhood of substantial properties. With level access from a well-maintained town road, this land offers an inviting blend of convenience and natural charm. Just minutes from the vibrant shops, dining, and cultural attractions of Woodstock Village, the property

  Sandy Reavill Real Broker LLC

  00 Carlton Hill Rd Unit 27, Woodstock, VT 05091
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  /32

  $1,295,000

  • 2 Beds
  • 3.5 Baths
  • 2,280 Sq Ft

  33 Mountain Ave, Woodstock, VT 05091

  Welcome to 33 Mountain Avenue – a mid-century modern gem poised perfectly on the edge of Faulkner Park and at the foot of Mt. Tom and once part of the Marianne Faulkner Estate. The spacious one-level design provides a seamless connection between the indoor and outdoor living space which includes two ensuite bedrooms, living/dining room with fireplace, kitchen, family room, office and attached one

  Mary Mayhew Snyder Donegan Real Estate Group

  33 Mountain Ave, Woodstock, VT 05091
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  /40

  $725,000

  • 4 Beds
  • 3 Baths
  • 3,584 Sq Ft

  3914 South Rd, Woodstock, VT 05091

  This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont’s changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level.

  Laird Bradley Williamson Group Sothebys Intl. Realty

  3914 South Rd, Woodstock, VT 05091
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  /48

  $689,000

  • 4 Beds
  • 3 Baths
  • 3,190 Sq Ft

  598 E Woodstock Rd, Woodstock, VT 05091

  Discover the charm of historic Woodstock, Vermont in this spacious, light-filled home just minutes from the village green. Blending timeless New England character with modern comfort, this property offers an abundance of space and versatility — ideal as a full-time residence or a relaxing ski-season getaway.This inviting home features hardwood floors, custom cherry built-ins, and two fireplaces,

  Erika Smith RE/MAX Upper Valley

  598 E Woodstock Rd, Woodstock, VT 05091
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  /60

  $2,395,000

  • 6 Beds
  • 5 Baths
  • 3,645 Sq Ft

  1362 Barnard Rd, Woodstock, VT 05091

  Gilbert’s Hill, the very best of Vermont living - Iconic, 112-acre estate with a storybook history as the first “modern” ski run in the US. Located two miles from the village center of Woodstock, the “prettiest small town in America", experience rural peace with convenient access to great restaurants and shops. Turnkey, fully-restored Vermont farmstead - a picturesque family compound with 7

  Chris Lang

  1362 Barnard Rd, Woodstock, VT 05091
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  /24

  $299,000

  • Land
  • 4.3 Acres
  • $69,535 per Acre

  00 Chateauguay Rd, Barnard, VT 05031

  A rare and beautiful parcel of land that is cleared, level and ready to be built upon with over 1200 feet of frontage along the North Branch of Locust Creek.Locust Creek runs year round with water falls and deep pools, not only pleasant to look at, but fun to play in.Site prep costs for a parcel like this will be considerably lower than wooded lots that require clearing and excavation.

  Stan Butler Four Seasons Sotheby's Int'l Realty

  00 Chateauguay Rd, Barnard, VT 05031
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  /31

  $995,000

  • 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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  $995,000

  • 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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  $1,195,000

  • 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

  $1,195,000

  • 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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  /42

  $1,250,000

  • 4 Beds
  • 2.5 Baths
  • 2,668 Sq Ft

  513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091

  This traditional New England Colonial, designed and custom built by Vermont Vernacular Builders, is sited to capture idyllic all-around mountain views and southern light. The spacious four-bedroom home features wide board floors, exposed beams, and a sun-filled chef’s kitchen and den. New Thor stainless steel 48" propane range installed October 2025.Privately set on over 8 acres, the property

  Chris Crowe Quechee Lakes Real Estate Center

  513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091
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  /42

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  1079 Fletcher Hill Rd, Woodstock, VT 05071

  This charming 2-bedroom ranch house offers a nice layout for main floor living. Features include a sunroom entrance, two bedrooms, a full bath, laundry room, and a main living/dining area with a kitchen, all within a rural setting with ample natural light, local views, and a deck. Recent updates include a primary bedroom ensuite featuring a custom walk-in shower and double sinks, new flooring, a

  Terry Davis Williamson Group Sothebys Intl. Realty

  1079 Fletcher Hill Rd, Woodstock, VT 05071
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  /45

  $439,000

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

  5798 W Woodstock Rd, Woodstock, VT 05091

  Charming 4 bedroom farmhouse with attached barn/garage with lots of overhead storage is located across the road from the scenic Ottauquechee River. Minutes from Woodstock Village Green with all of its amenities and a short distance from Killington with its world renown Ski Resort. Year round activities abound ! The house has a sunny eat in kitchen, spacious dining room and a living room

  Carol Wood Williamson Group Sothebys Intl. Realty

  5798 W Woodstock Rd, 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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  /50

  $1,100,000

  • 3 Beds
  • 2.5 Baths
  • 2,220 Sq Ft

  958 E Woodstock Rd, Woodstock, VT 05091

  Just minutes from the heart of Woodstock, this 3-bedroom, 3-bath home with a dedicated office/family room has been transformed from the ground up into a modern, energy-efficient retreat. Taken down to the studs, the renovation was comprehensive—every system replaced, with all new wiring, plumbing, insulation, and mechanicals, along with a new roof, Pella windows, central heating, and air

  Keri Cole Williamson Group Sothebys Intl. Realty

  958 E Woodstock Rd, Woodstock, VT 05091
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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

  (802) 347-9544

  41 Pleasant St, Woodstock, VT 05091
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  /49

  $749,000

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft

  37 South St, Woodstock, VT 05091

  Holiday price reduction! Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  37 South St, Woodstock, VT 05091
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  /43

  $595,000

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  1514 South Rd, Woodstock, VT 05091

  This tidy, well maintained Mid-Century Ranch home is conveniently located just 1.5 miles from the Village Green. Perched on a sunny knoll with a southern valley view, this well maintained home features open concept kitchen/dining, a large, bright living room, three bedrooms all with oak floors, a walk out basement providing opportunity for guest accommodation, or a hobby/play room. The 2 car

  Danny Kogut Williamson Group Sothebys Intl. Realty

  1514 South Rd, Woodstock, VT 05091
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  /35

  $495,000

  • 4 Beds
  • 3 Baths
  • 2,470 Sq Ft

  3364 W Woodstock Rd, Woodstock, VT 05091

  Welcome to this lovingly updated antique Cape, set on two open, level acres across from the sparkling Ottauquechee River. Just five minutes from Woodstock Village and perfectly positioned on the west side for quick trips to Killington and Pico, this home makes the ideal Vermont getaway. Inside, you’ll find four comfortable bedrooms and a warm, inviting layout designed for making memories. Gather

  Keri Cole Williamson Group Sothebys Intl. Realty

  3364 W Woodstock Rd, Woodstock, VT 05091
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  /42

  $3,500,000

  • 6 Beds
  • 8 Baths
  • 5,142 Sq Ft

  18 The Green, Woodstock, VT 05091

  Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town’s finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort

  Danny Kogut Williamson Group Sothebys Intl. Realty

  18 The Green, Woodstock, VT 05091
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  /38

  $795,000

  • 4 Beds
  • 3 Baths
  • 2,099 Sq Ft

  6077 Vt Route 12, Barnard, VT 05031

  BARNARD VILLAGE CAPE- This elegant Cape sits in an ideal location in the idyllic village of Barnard, just a short walk to the Barnard General Store and Silver Lake. The perfect blend of original charm, sophistication, and modern amenities, the house is bright and welcoming with lovely natural woodwork and plenty of space for social gatherings or quiet privacy. A large central living room features

  David Donegan Snyder Donegan Real Estate Group

  6077 Vt Route 12, Barnard, VT 05031
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  /37

  $985,000

  • 4 Beds
  • 3 Baths
  • 2,785 Sq Ft

  1782 Randall Rd, Woodstock, VT 05091

  This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

  Wade Treadway Wade I Treadway Real Estate

  1782 Randall Rd, Woodstock, VT 05091
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  /32

  $72,999

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  185 Riverbend Way, Woodstock, VT 05091

  Start your Vermont dream with this affordable 3-bedroom, 2-bath mobile home just minutes from downtown Woodstock, VT. Located in a quiet, private community with stunning mountain views and direct river frontage on the Ottauquechee, this home is a rare opportunity to enjoy scenic living at a budget-friendly price. Perfect as a first home, vacation getaway, or investment, this property is also

  Mendi Michael Engel & Völkers Okemo

  185 Riverbend Way, Woodstock, VT 05091
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  /49

  $1,595,000

  • 5 Beds
  • 3.5 Baths
  • 3,648 Sq Ft

  1522 Barnard Rd, Woodstock, VT 05091

  Just 2 miles from Woodstock Village, this gracious brick cape on 6 open acres offers space, comfort, and classic Vermont charm. The expanded chef’s kitchen opens to a gracious gathering room ideal for entertaining, while 3 fireplaces—wood-burning, brick, and gas-ready—provide cozy warmth throughout. Upstairs, find 3–4 bedrooms including one with its own fireplace, plus a private guest room or

  Keri Cole Williamson Group Sothebys Intl. Realty

  1522 Barnard Rd, Woodstock, VT 05091
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  /57

  $817,000

  • 3 Beds
  • 2 Baths
  • 2,760 Sq Ft

  616 Rose Hill Rd, Woodstock, VT 05091

  This is a rare opportunity to own 10.1 acres of land in a coveted area of Woodstock that includes a 1988 Frizzell Builders house and a detached oversized garage with a second floor for storage . The property was part of the King Farm which is now in Vt. Land Trust as conserved land , until it was split off in the late 1980's when the Colby family came into ownership and built the existing house

  Carol Wood Williamson Group Sothebys Intl. Realty

  616 Rose Hill Rd, Woodstock, VT 05091
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  /41

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 2,532 Sq Ft

  7 Slayton Terrace, Woodstock, VT 05091

  A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully

  Keri Cole Williamson Group Sothebys Intl. Realty

  7 Slayton Terrace, Woodstock, VT 05091
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  /45

  $895,000

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft

  72 Oakridge Way, Woodstock, VT 05091

  PRIME LOCATION! Tucked away at the end of a peaceful dead-end road in the Westerdale neighborhood is this Vermont Cape Cod home offers the perfect blend of privacy and convenience on just over 6 acres. Surrounded by mature trees and set on a wooded lot overlooking a tranquil pond, you’ll enjoy the calm of nature right outside your doorstep. The freshly installed deck provides a serene spot.

  Nancy Greenwood Watson Realty & Associates

  72 Oakridge Way, Woodstock, VT 05091
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  /41

  $614,000

  • 3 Beds
  • 2 Baths
  • 1,908 Sq Ft

  530 West Rd, Barnard, VT 05031

  Conveniently located less than a mile from Barnard General Store and Silver Lake, this charming 3 bedroom cape sits on just over 3 acres of land with tiered stone walls and green lawn circling the house. Mature trees surround the yard and there is view potential with minor clearing and thinning. The full length back deck offers private outdoor space including a covered grilling area just steps

  Dan Noble Snyder Donegan Real Estate Group

  530 West Rd, Barnard, VT 05031
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  /55

  $915,000

  • 3 Beds
  • 3 Baths
  • 2,150 Sq Ft

  509 Church Hill Rd, Wood Stock, VT 05091

  Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens.The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes ,

  Carol Wood Williamson Group Sothebys Intl. Realty

  509 Church Hill Rd, Wood Stock, VT 05091
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  /48

  $6,750,000 New Construction

  • 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 65 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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  /33

  $3,945,000

  • 5 Beds
  • 5.5 Baths
  • 8,122 Sq Ft

  5685 Vermont 12, Barnard, VT 05031

  If you’ve been looking for the iconic Vermont home, rarely does an opportunity like this present itself. Welcome to HIGHLAND GLEN, an idyllic Vermont home situated on 12 picturesque acres in the quaint town of Barnard, VT. Upon arrival at Highland Glen, you'll immediately sense the special charm of this property, from the red barn to the mature apple orchard and sugar maples - your eyes will be

  John Snyder Snyder Donegan Real Estate Group

  5685 Vermont 12, Barnard, VT 05031
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  /17

  $835,000

  • Land
  • 150 Acres
  • $5,567 per Acre

  0 Walker Hill Rd Unit 5039522, Bridgewater, VT 05091

  150 acres of recreational paradise! Absolute and total privacy! Enjoy long views of mountain peaks showing criss crossed ski trails, pristine cascading streams with mesmerizing waterfalls over large rock outcroppings, mature woodland which hasn't been logged in over 50 years, a fully equipped camper trailer with propane fired generator for off grid living and even a 4 wheeler outfitted with

  John Wetmore Wetmore Real Estate

  0 Walker Hill Rd Unit 5039522, Bridgewater, VT 05091
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  /47

  $8,000,000

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

  115 Eastman Rd, Woodstock, VT 05091

  Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

  Keri Cole Williamson Group Sothebys Intl. Realty

  115 Eastman Rd, Woodstock, VT 05091
• 

  

  /6

  $239,000

  • 2 Beds
  • 1 Bath
  • 1,190 Sq Ft

  442 E Woodstock Rd Unit 4A, Woodstock, VT 05091

  Airy, tranquil and quiet, this former yoga studio space has been converted into a two bedroom condo. Sweeping views through the Palladian window, large living area with soaring vaulted ceiling, newer kitchen with granite counters and newer bath with walk in shower. Spacious entry can accommodate bikes, skis and more. Walking distance to shops, restaurants, entertainment and recreation in the

  Jane Darrach Martha E. Diebold/Hanover

  442 E Woodstock Rd Unit 4A, Woodstock, VT 05091
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  /9

  $275,000

  • Land
  • 0.43 Acre
  • $639,535 per Acre

  1054 W Woodstock Rd, Woodstock, VT 05091

  Ideally located parcel across West Woodstock Road from the Woodstock Farmers Market and 500 yards from the entry to Woodstock Union Middle & High School. Public water and sewer available with access off Prosper Road near the junction of US Road Route 4/West Woodstock Road. Building plans available. Multi-unit housing development potential in zero vacancy environment.

  Laird Bradley Williamson Group Sothebys Intl. Realty

  1054 W Woodstock Rd, Woodstock, VT 05091

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