Woodstock, VT Homes

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  $950,000 Under Contract

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

  34 Midsomer Meadows Ln, Woodstock, VT 05091

  Welcome to Starry Hill, a fully furnished, handcrafted, solid-timber Colonial privately nestled on 18.9 tranquil acres just 5 miles North of Woodstock. This 3-bedroom, 2.5 bath home was built over 4 years by a family of loggers and master craftsmen. Used recently as an AirBnB rental and ready for occupancy. This exceptional home features Eastern white pine walls, hemlock structural beams, and

  

  John Bassette

  Bassette Real Estate Group

  (802) 347-6383

  34 Midsomer Meadows Ln, Woodstock, VT 05091
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  /11

  $1,995 Per Month

  • 1 Bed
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  36 Happy Valley Rd, Woodstock, VT 05091

  This charming first-floor, one-bedroom apartment is located in the grand and historic Four Pillars, a classic Greek Revival home, in the quaint and peaceful hamlet of Taftsville, just outside the village of Woodstock, Vermont. The apartment features high ceilings, large sun-filled windows, and beautiful hardwood floors throughout. The spacious kitchen is fully equipped with modern appliances,

  Timothy Thompson Covered Bridge RE

  36 Happy Valley Rd, Woodstock, VT 05091
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  /53

  $798,000 Sold Oct 31, 2025

  392 Gully Rd, Woodstock, VT 05091

  • 2 Beds
  • 2 Baths
  • 1,308 Sq Ft
  • Built 2019

  Last Sold Summary

  • $610/SF
  • 28 Days On Market

  Current Estimated Value $758,277

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  392 Gully Rd, Woodstock, VT 05091
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  /20

  Est $3,036,925 Not Listed For Sale

  3086 South Rd, Woodstock, VT 05091

  • 4 Beds
  • 4.5 Baths
  • 3,550 Sq Ft
  • Built 1986

  3086 South Rd, Woodstock, VT 05091

  Last Sold Summary

  • 5% Above List Price
  • $817/SF
  • 0 Days On Market

  • Last Sold Price $2,900,000
  • May 05, 2025

  Last Listing Agent John Snyder Snyder Donegan Real Estate Group
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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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  /27

  $3,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,237 Sq Ft
  • 2 Bedroom in Woodstock

  51 Terrace St, Woodstock, VT 05091

  Welcome to the Furnished 2 Bedroom in Woodstock, a charming home nestled in the heart of Woodstock, VT. This home boasts two spacious bedrooms and two full bathrooms, perfect for those who value comfort and convenience. The updated kitchen and baths add a modern touch to the home, while the hardwood flooring throughout gives it a warm, inviting feel. The home is equipped with air conditioning,

  51 Terrace St, Woodstock, VT 05091
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  /36

  $655,000 Sold Nov 24, 2025

  4 Stanton St, Woodstock, VT 05091

  • 4 Beds
  • 2.5 Baths
  • 2,124 Sq Ft
  • Built 1901

  Last Sold Summary

  • 18% Above List Price
  • $308/SF
  • 7 Days On Market

  Current Estimated Value $609,874

  Last Listing Agent Nan Carroll Coldwell Banker LIFESTYLES - Hanover

  4 Stanton St, Woodstock, VT 05091
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  Not Listed For Sale

  6963 South Rd, Woodstock, VT 05071

  • 2 Beds
  • 1.5 Baths
  • 1,840 Sq Ft
  • Built 1970

  6963 South Rd, Woodstock, VT 05071

  Last Sold Summary

  • $408/SF
  • 43 Days On Market

  • Last Sold Price $750,000
  • May 01, 2025

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty
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  $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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  /25

  $3,200 Per Month

  • 2 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Apartment for Rent

  21 Central St, Woodstock, VT 05091

  Offered for lease is a luxury apartment in the very heart of Woodstock Village! The elevated location, above the hub of central village shopping, presents captivating views of village activity, as well as distant hills. The owners started with a blank slate, in a previously vacant space and have provided all of the benefits of wall to wall new construction. State of the art mechanical systems

  John Wetmore Wetmore Real Estate

  21 Central St, Woodstock, VT 05091
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  $1,625,000 Sold Oct 24, 2025

  7 North St, Woodstock, VT 05091

  • 2 Beds
  • 3 Baths
  • 2,106 Sq Ft
  • Built 1880

  Last Sold Summary

  • 12% Below List Price
  • $772/SF
  • 111 Days On Market

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty

  7 North St, Woodstock, VT 05091
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  /40

  Est $593,583 Not Listed For Sale

  105 Happy Valley Rd, Woodstock, VT 05091

  • 3 Beds
  • 1 Bath
  • 1,700 Sq Ft
  • Built 1848

  105 Happy Valley Rd, Woodstock, VT 05091

  Last Sold Summary

  • 3% Above List Price
  • $338/SF
  • 274 Days On Market

  • Last Sold Price $575,000
  • May 09, 2025

  Last Listing Agent John Bassette Bassette Real Estate Group
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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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  /40

  $1,625,000 Sold Sep 29, 2025

  441 Spruce Way, Woodstock, VT 05091

  • 4 Beds
  • 3 Baths
  • 2,619 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $620/SF
  • 6 Days On Market

  Current Estimated Value $1,591,365

  Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  441 Spruce Way, Woodstock, VT 05091
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  Est $1,142,113 Not Listed For Sale

  5274 W Woodstock Rd, Woodstock, VT 05091

  • 2 Beds
  • 2 Baths
  • 2,058 Sq Ft
  • Built 1972

  5274 W Woodstock Rd, Woodstock, VT 05091

  Last Sold Summary

  • 4% Below List Price
  • $581/SF
  • 15 Days On Market

  • Last Sold Price $1,195,000
  • Dec 12, 2024

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty
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  $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
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  /32

  $700,000 Sold May 30, 2025

  13 Golf Ave, Woodstock, VT 05091

  • 2 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Built 1880

  Last Sold Summary

  • $461/SF
  • 0 Days On Market

  Current Estimated Value $673,918

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

  13 Golf Ave, Woodstock, VT 05091
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  Est $908,558 Not Listed For Sale

  433 Cowdrey Path, Woodstock, VT 05091

  • 4 Beds
  • 4 Baths
  • 3,507 Sq Ft
  • Built 1986

  433 Cowdrey Path, Woodstock, VT 05091

  Last Sold Summary

  • 7% Below List Price
  • $278/SF
  • 207 Days On Market

  • Last Sold Price $975,000
  • Jul 31, 2023

  Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group
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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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  /22

  $618,500 Sold Oct 03, 2025

  187 Dana Rd, Woodstock, VT 05091

  • 3 Beds
  • 1.5 Baths
  • 1,468 Sq Ft
  • Built 1955

  Last Sold Summary

  • 8% Below List Price
  • $421/SF
  • 108 Days On Market

  Current Estimated Value $603,522

  Last Listing Agent Mary Mayhew Snyder Donegan Real Estate Group

  187 Dana Rd, Woodstock, VT 05091
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  /35

  Est $595,591 Not Listed For Sale

  93 Blackbriar Rd, Woodstock, VT 05091

  • 2 Beds
  • 1 Bath
  • 1,146 Sq Ft
  • Built 1950

  93 Blackbriar Rd, Woodstock, VT 05091

  Last Sold Summary

  • $519/SF
  • 38 Days On Market

  • Last Sold Price $595,000
  • Oct 11, 2024

  Last Listing Agent David Donegan Snyder Donegan Real Estate Group
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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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  $1,520,000 Sold Sep 30, 2025

  6196 Stage Rd, Woodstock, VT 05091

  • 4 Beds
  • 4 Baths
  • 2,408 Sq Ft
  • Built 2015

  Last Sold Summary

  • 2% Above List Price
  • $631/SF
  • 4 Days On Market

  Last Listing Agent Eric Johnston Four Seasons Sotheby's Int'l Realty

  6196 Stage Rd, Woodstock, VT 05091
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  Not Listed For Sale

  5 Mountain Ave Unit 4, Woodstock, VT 05091

  • 2 Beds
  • 2.5 Baths
  • 1,590 Sq Ft
  • Built 1880

  5 Mountain Ave Unit 4, Woodstock, VT 05091

  Last Sold Summary

  • $550/SF
  • 12 Days On Market

  • Last Sold Price $875,000
  • Dec 10, 2024

  Last Listing Agent Keri Cole Williamson Group Sothebys Intl. Realty
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  $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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  /15

  $120,000 Sold Apr 17, 2026

  00 Carlton Hill Rd, Woodstock, VT 05091

  • Land
  • 3.54 Acres
  • $33,898 per Acre

  Last Sold Summary

  • 19% Below List Price
  • 0 Days On Market

  Last Listing Agent Sandy Reavill

  00 Carlton Hill Rd, Woodstock, VT 05091
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  /40

  Not Listed For Sale

  318 Ebbin Lockwood Way, Woodstock, VT 05071

  • 3 Beds
  • 3.5 Baths
  • 6,047 Sq Ft
  • Built 1970

  318 Ebbin Lockwood Way, Woodstock, VT 05071

  Last Sold Summary

  • $455/SF
  • 495 Days On Market

  • Last Sold Price $2,750,000
  • Feb 13, 2025

  Last Listing Agent Story Jenks LandVest, Inc/Woodstock
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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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  $2,210,000 Sold Sep 24, 2025

  15 Hathorn Hill Street Extension, Woodstock, VT 05091

  • 4 Beds
  • 3.5 Baths
  • 3,564 Sq Ft
  • Built 2009

  Last Sold Summary

  • 1% Above List Price
  • $620/SF
  • 68 Days On Market

  Last Listing Agent John Snyder Snyder Donegan Real Estate Group

  15 Hathorn Hill Street Extension, Woodstock, VT 05091
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  Not Listed For Sale

  1028 Fairbanks Turn, Woodstock, VT 05091

  1028 Fairbanks Turn, Woodstock, VT 05091

  Last Sold Summary

  • 162 Days On Market

  • Last Sold Price $110,000
  • Mar 21, 2025

  Last Listing Agent Heather Ashline BHHS Verani Upper Valley
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  /60

  $1,300,000 Under Contract

  • 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

  $1,650,000 Sold Nov 08, 2025

  2334 South Rd, Woodstock, VT 05091

  • 3 Beds
  • 2.5 Baths
  • 5,422 Sq Ft
  • Built 1972

  Last Sold Summary

  • 25% Below List Price
  • $304/SF
  • 94 Days On Market

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty

  2334 South Rd, Woodstock, VT 05091
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  /27

  Est $854,705 Not Listed For Sale

  7 Golf Ave, Woodstock, VT 05091

  • 5 Beds
  • 3 Baths
  • 3,579 Sq Ft
  • Built 1832

  7 Golf Ave, Woodstock, VT 05091

  Last Sold Summary

  • 55% Above List Price
  • $154/SF
  • 47 Days On Market

  • Last Sold Price $550,000
  • Oct 19, 2023

  Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty
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  $1,195,000 Under Contract

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

  513 Deer Brook Way, Woodstock, VT 05091

  Set on a sun-bathed hillside between Woodstock Village and the renowned slopes of Killington and Pico, this custom-built Colonial captures what buyers seek most in Vermont: privacy, craftsmanship, and striking mountain views that feel close enough to touch. Thoughtfully designed by the respected Vermont Vernacular Builders, the home reflects classic regional architecture with refined proportions,

  Keri Cole Williamson Group Sothebys Intl. Realty

  513 Deer Brook Way, Woodstock, VT 05091
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  $613,000 Sold Sep 10, 2025

  5851 South Rd, Woodstock, VT 05071

  • 3 Beds
  • 2.5 Baths
  • 1,958 Sq Ft
  • Built 1920

  Last Sold Summary

  • 19% Below List Price
  • $313/SF
  • 302 Days On Market

  Last Listing Agent Carol Wood Williamson Group Sothebys Intl. Realty

  5851 South Rd, Woodstock, VT 05071
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  Est $492,597 Not Listed For Sale

  24 High St, Woodstock, VT 05091

  • 5 Beds
  • 2 Baths
  • 2,996 Sq Ft
  • Built 1840

  24 High St, Woodstock, VT 05091

  Last Sold Summary

  • 7% Above List Price
  • $154/SF
  • 325 Days On Market

  • Last Sold Price $460,000
  • Apr 18, 2025

  Last Listing Agent Danny Kogut Williamson Group Sothebys Intl. Realty
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  $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
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  /48

  $705,000 Sold Nov 26, 2025

  25 Linden Hill St, Woodstock, VT 05091

  • 3 Beds
  • 2 Baths
  • 1,694 Sq Ft
  • Built 1910

  Last Sold Summary

  • 11% Below List Price
  • $416/SF
  • 217 Days On Market

  Last Listing Agent Laird Bradley Williamson Group Sothebys Intl. Realty

  25 Linden Hill St, Woodstock, VT 05091
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  /39

  Est $801,893 Not Listed For Sale

  6 Highland Ave, Woodstock, VT 05091

  • 1 Bed
  • 1 Bath
  • 1,052 Sq Ft
  • Built 1930

  6 Highland Ave, Woodstock, VT 05091

  Last Sold Summary

  • 96% Above List Price
  • $390/SF
  • 97 Days On Market

  • Last Sold Price $410,000
  • Apr 01, 2025

  Last Listing Agent John Wetmore Wetmore Real Estate
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  $895,000 Under Contract

  • 4 Beds
  • 1.5 Baths
  • 1,580 Sq Ft

  51 River St, Woodstock, VT 05091

  Beautiful residence with newer renovations...located in the heart of historic Woodstock. Sunlit rooms, open floor concept with handsome refinished original pine floors. Stunning kitchen with stainless appliances, oversized island and soapstone counters accent the new cabinetry. Large dining room for entertaining with lovely screened in porch with double doors that lead out to a privately enclosed

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  51 River St, Woodstock, VT 05091

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