Homes for Sale in 05091

• 

  

  

  /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
• 

  

  

  /32

  $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
• 

  

  

  /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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  /38

  $750,000

  $45K PRICE DROP

  • 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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  /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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  /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
• 

  

  /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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  /41

  $1,495,000

  • 4 Beds
  • 1.5 Baths

  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 Sotheby's International Realty

  7 Slayton Terrace, Woodstock, VT 05091
• 

  

  /52

  $1,395,000

  $100K PRICE DROP

  • 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 the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add

  Keri Cole Williamson Group Sothebys Intl. Realty

  1522 Barnard Rd, Woodstock, VT 05091
• 

  

  /12

  $199,000

  • Land
  • 29 Acres
  • $6,862 per Acre

  00 Vermont 12, Barnard, VT 05031

  A beautiful and private 29 acre building lot on a mountainside in an area of Barnard populated by estate properties. A road to the potential building site is in and soil testing for septic will be completed as soon as snow clears. Views of the valley and local mountains currently cleared and can be expanded with additional clearing. The location is a short drive to Woodstock, a shorter drive to

  Stan Butler Four Seasons Sotheby's Int'l Realty

  00 Vermont 12, Barnard, VT 05031
• 

  

  /48

  $2,500,000

  • 6 Beds
  • 6 Baths
  • 7,019 Sq Ft

  5518 Vermont 12, Barnard, VT 05031

  This gracious 1796 Brick Federal homestead was transformed into a popular gathering spot more than 60 years ago. The Barnard Inn has long been considered among the finest dining and hospitality venues in Vermont. It is currently operated as an event destination by the chef-owner and his family. Now, with children grown and off on their own paths, it is time to pass stewardship of the historic

  Laird Bradley Williamson Group Sothebys Intl. Realty

  5518 Vermont 12, Barnard, VT 05031
• 

  

  /48

  $527,000

  • 4 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  88 Happy Valley Rd, Woodstock, VT 05091

  Step into a rare offering where timeless New England charm meets contemporary comfort. Originally built in 1846 and thoughtfully reimagined, this exceptional Taftsville, Vermont residence is set along Happy Valley Brook, creating a private sanctuary defined by peace, beauty, and understated elegance. Historic character is beautifully complemented by carefully curated upgrades, including

  Julie Davis KW Vermont Woodstock

  88 Happy Valley Rd, Woodstock, VT 05091
• 

  

  /21

  $99,000

  • Land
  • 1.52 Acres
  • $65,132 per Acre

  0 Gold Coast Rd Unit 5089928, Bridgewater, VT 05035

  For many years the owners have enjoyed the serenity of this beloved campsite, as their Vermont Summer retreat. Now the time has come to pass their property on, for new owners to establish vacation memories of their own. The 1.5 acre parcel is wonderfully diverse! Near the height of the land an open area could well be the site for constructing a cabin. When facing South from this area a pleasant

  John Wetmore Wetmore Real Estate

  0 Gold Coast Rd Unit 5089928, Bridgewater, VT 05035
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  /51

  $6,673,000

  • 5 Beds
  • 3.5 Baths
  • 4,165 Sq Ft

  2358 Long Hill Rd, Woodstock, VT 05091

  Framed by groves of mature birch trees, a winding drive descends into a private valley surrounded by pastures, apple orchards, a spring-fed pond, and sweeping mountain views, arriving at Birch Tree Farm. Spanning more than 465 acres, this extraordinary Vermont retreat offers an immersive four-season lifestyle -- from pressing fresh cider from the orchard and tapping maple trees for syrup to

  Story Jenks LandVest, Inc/Woodstock

  2358 Long Hill Rd, Woodstock, VT 05091
• 

  

  /19

  $450,000

  • Land
  • 69 Acres
  • $6,522 per Acre

  00 Vermont 12, Barnard, VT 05031

  A 69 acre mountaintop building lot with dramatic views of distant mountains in an area of Barnard populated with estate properties. The road is in to a potential building site at the height of the land. Soil testing for septic will be completed as soon as snow clears. Subdivision pending. This parcel is currently comprised of two parcels, one being 40+/- acres and the second being 29+/- which can

  Stan Butler Four Seasons Sotheby's Int'l Realty

  00 Vermont 12, Barnard, VT 05031
• 

  

  /17

  $825,000

  $10K PRICE DROP

  • Land
  • 150 Acres
  • $5,500 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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  /40

  $479,000

  $21K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  7429 US Route 4, Bridgewater, VT 05034

  THE SUGAR HOUSE — Beautifully renovated in 2007, this light-filled Vermont home is ideally located in the heart of historic Bridgewater, just 10 minutes from the charm, dining, and culture of the village of Woodstock. Offering the perfect balance of four-season recreation and classic New England character, the property is equally suited as a primary residence, weekend retreat, or investment

  Keri Cole Williamson Group Sothebys Intl. Realty

  7429 US Route 4, Bridgewater, VT 05034
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  /46

  $718,500

  $31K PRICE DROP

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

  37 South St, Woodstock, VT 05091

  Great new price! Nestled in the vibrant heart of Woodstock Village, this beautifully renovated residence offers the ultimate "walk-to-all" lifestyle. Stepping inside, newly installed pine flooring guides you through an inviting main level designed for both daily living and effortless entertaining. The cozy living room anchors the home with its warm gas fireplace, while the spacious dining area

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  37 South St, Woodstock, VT 05091
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  /44

  $650,000

  • 2 Beds
  • 2 Baths
  • 1,044 Sq Ft

  35 White Loop Unit B101, Ludlow, VT 05149

  Winterplace on Okemo Mountain. This is a must see condominium at an unbeatable location on Okemo. Located at the top of the A & B quad which brings you directly to the Sunburst Six summit chairlift. Natural light fills the bright living space with an open floor plan for the living room, kitchen, and dining area. There is plenty of space for family and friends to gather. A few key features include

  Katherine Burns William Raveis Real Estate Vermont Properties

  35 White Loop Unit B101, Ludlow, VT 05149
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  /57

  $3,749,000

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

  5685 Vermont 12, Barnard, VT 05031

  “HIGHLAND GLEN” – Rarely does a property capture the essence of Vermont as beautifully as Highland Glen. Set on twelve picturesque acres in the charming town of Barnard, this extraordinary estate blends timeless New England character with exceptional comfort, privacy, and recreation.Arrive by the iconic red barn and discover stunning gardens, apple orchard, meandering stone walls, flowing

  John Snyder Snyder Donegan Real Estate Group

  5685 Vermont 12, Barnard, VT 05031
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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 spacce), 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
• 

  

  /11

  $695,000

  • 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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  /41

  $4,250,000

  • 7 Beds
  • 9 Baths
  • 9,615 Sq Ft

  5893 Stage Rd, Barnard, VT 05031

  Set on 54 exceptionally private acres, Long Way Hill is a a quietly luxurious Vermont country retreat overlooking a half-acre pond, with sweeping lawns, gardens, fields, and woodland trails. It is located minutes from Silver Lake and Twin Farms, and 15 minutes from Woodstock. Designed by David Beilman and built by Savelberg Construction in 2006, the home is defined by its high

  Story Jenks LandVest, Inc/Woodstock

  5893 Stage Rd, Barnard, VT 05031
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  /45

  $675,000

  $14K PRICE DROP

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

  598 E Woodstock Rd, Woodstock, VT 05091

  Historic Woodstock, Vermont – Spacious Home on Nearly 3 Acres. Welcome to a rare opportunity in the heart of Woodstock, one of Vermont’s most picturesque and sought-after villages. This expansive home offers generous living space with many rooms, providing flexibility for a large household, home offices, guest quarters, or the potential to create multiple apartments (buyer to verify local

  Erika Smith Coldwell Banker LIFESTYLES - Hanover

  598 E Woodstock Rd, Woodstock, VT 05091
• 

  

  /39

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  1821 Chateauguay Rd, Bethel, VT 05032

  This sunny residence has been a beloved home to several generations of the same Vermont family. The location invites recreational activities! A snowmobile trail passes nearby, for winter excursions and the property is bounded by the cascading waters of Locust Creek, for cooling off in the Summer! The country road that passes by leads to the extraordinary Chateauguay-No Town conservation region,

  John Wetmore Wetmore Real Estate

  1821 Chateauguay Rd, Bethel, VT 05032
• 

  

  /44

  $730,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  46 Fowler Rd Unit O-205, Ludlow, VT 05149

  Winterplace at Okemo Mountain - Experience the ultimate in slopeside convenience, widely regarded as one of the most accessible locations on the mountain, with rare access to five chairlifts and nearby trail connections that bring you directly onto the slopes. This inviting three-bedroom, two-bathroom condo features an open-concept living area highlighted by a wood-burning fireplace—perfect for

  Katherine Burns William Raveis Real Estate Vermont Properties

  46 Fowler Rd Unit O-205, Ludlow, VT 05149
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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
• 

  

  /11

  $299,000

  • Land
  • 40 Acres
  • $7,475 per Acre

  00 Vermont 12, Barnard, VT 05031

  A perfect opportunity to build in this dramatic and private mountaintop location with long range views to the east and south. An excellent Barnard location in an area of estate properties. Being sold as 40 +/- acres with an additional 29 acres available. Road to building site in and septic soil tests will be performed after snow melt. Subdivision pending. A short drive to Woodstock and an even

  Stan Butler Four Seasons Sotheby's Int'l Realty

  00 Vermont 12, Barnard, VT 05031
• 

  

  /17

  $325,000

  • Land
  • 51.59 Acres
  • $6,300 per Acre

  334 Log Cabin Dr, Pomfret, VT 05067

  334 Log Cabin Drive offers 51.59 acres of hardwood forest in South Pomfret, Vermont, with east and south-facing aspects through an open canopy. The stand lets light in all winter and turns into a cathedral in October. Mature birch, beech, and maple rise from a clean understory with good spacing, and scattered spruce and hemlock anchor the margins. Leaf-off views sweep across the ridgeline with no

  Richard Higgerson Higgerson & Company

  334 Log Cabin Dr, Pomfret, VT 05067
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  /32

  $75,000

  $5K PRICE DROP

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

  185 Riverbend Way, Woodstock, VT 05091

  Seller is offering $10,000 towards closing costs and prepaids! 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

  Mendi Michael Engel & Völkers Okemo

  185 Riverbend Way, Woodstock, VT 05091
• 

  

  /21

  $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
• 

  

  /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
• 

  

  /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
• 

  

  /60

  $510,000

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

  85 Townhouse Way Unit 18, Woodstock, VT 05091

  Enjoy the ease of townhouse living in this beautiful fully furnished end unit filled with natural light throughout. The setting is surrounded by woodlands and lovely landscaped grounds . The bright living room complete with wood burning fireplace steps down to a lovely kitchen with dining area .Walk out through double sliding doors onto a private deck for one of two outdoor living spaces. There

  Carol Wood Williamson Group Sothebys Intl. Realty

  85 Townhouse Way Unit 18, 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
• 

  

  /5

  $850,000

  • Land
  • 1.47 Acres
  • $578,231 per Acre

  97 Valley View Rd, Woodstock, VT 05091

  The justifiably proud owner of this property points out these features: Potential "Barnominium." Conveniently located just 1/4 mile from Woodstock Village town line and just 40 minutes from Killington Ski area. Built for an auto collection. Full bathroom, blown in insulation in ceiling, foam spray insulation in walls (with bug mesh in walls.) 3/4" sheet rock! All electrical is done in 3/4'

  John Wetmore Wetmore Real Estate

  97 Valley View Rd, Woodstock, VT 05091
• 

  

  /48

  $6,750,000

  New Construction $500K 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
• 

  

  /37

  $985,000

  $200K PRICE DROP

  • 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
• 

  

  /47

  $395,000

  $44K 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
• 

  

  /8

  $275,000

  • Land
  • 1.95 Acres
  • $141,026 per Acre

  3186 South Rd, Woodstock, VT 05091

  1.95 Acre lot minutes from Woodstock Village, South Woodstock, and Green Mountain Horse Association. Kidder Brook runs along the North property boundary, and a sunny lawn area has multiple small gardens. There is a large clearing, and a well-cared for 1973 mobile home on a concrete slab on the property. This lot has tremendous potential in a fantastic location. House is being sold As-is.

  Andrew Hubbell Vermont Real Estate Company

  3186 South Rd, Woodstock, VT 05091

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