51

Homes for Sale in 05091

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  • /14

    $236,000

    Open Fri 4PM - 6PM
    • 1 Bed
    • 1 Bath
    • 856 Sq Ft

    42 Heritage Condo Way Unit 24, Woodstock, VT 05091

    Amazing opportunity to own a property that is perfect as a full time home or a vacation get away, in the highly desired Heritage Condo community. Quiet setting in a low density area. This end unit condo has had many updates and is ready for new owners to add their personal touch. A private deck looking out to woodlands and lawn. The bright kitchen is a pleasure to work in . Upstairs the den with

    Ara Cardew BHG Masiello Keene

    42 Heritage Condo Way Unit 24, Woodstock, VT 05091
  • /48

    $1,075,000

    • 3 Beds
    • 3 Baths
    • 3,030 Sq Ft

    648 Church Hill Rd, Wood Stock, VT 05091

    This superbly cared-for cape-style home has been thoughtfully and comprehensively updated, with all bathrooms tastefully renovated with quality fixtures and finishes. The home features a creative, livable floor plan with a mix of open gathering rooms and comfortable private spaces, accented with crown molding and 8 1/2-foot ceilings on the main level. The main level has two entries, with

    Laird Bradley Williamson Group Sothebys Intl. Realty

    648 Church Hill Rd, Wood Stock, VT 05091
  • /48

    $1,695,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 3,542 Sq Ft

    353 Cabot Rd, Woodstock, VT 05091

    "BLISS HOUSE" Privately nestled on a picturesque hillside just minutes from the Woodstock Village Green, this beautifully renovated residence offers exceptional privacy, sweeping long-range mountain views, open meadows, mature gardens, a swimming pool, hot tub, and the perfect blend of Vermont charm and modern comfort. A thoughtful renovation transformed the kitchen and dining areas into a

    John Snyder Snyder Donegan Real Estate Group

    353 Cabot Rd, Woodstock, VT 05091
  • /31

    $244,000

    • 1 Bed
    • 1 Bath
    • 856 Sq Ft

    42-18 Heritage Condo Way Unit 18D, Woodstock, VT 05091

    Easy living in this updated condo that is perfect for a primary or secondary residence. Located in a small condo community that is mostly owner occupied the setting offers a private living space. The deck looks out to well maintained grounds and woodlands. The updated kitchen and bathroom are well appointed. The main level has an open floor plan that includes the kitchen, dining area and living

    Carol Wood Williamson Group Sothebys Intl. Realty

    42-18 Heritage Condo Way Unit 18D, Woodstock, VT 05091
  • /60

    $1,375,000

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

    16 Church St, Woodstock, VT 05091

    This wonderful Vermont Cape-style home has overlooked the Ottauquechee River and the former Woodstock woolen mill (now the 'new' mill and community pools and recreation center) since 1890. On long summer days, the sounds of children enjoying the swimming holes and tubing in the rapid runs below float up. The floor plan has been adapted to modern lifestyles across three levels. The main level,

    Laird Bradley Williamson Group Sothebys Intl. Realty

    16 Church St, Woodstock, VT 05091
  • /53

    $1,500,000

    • 6 Beds
    • 6 Baths
    • 6,240 Sq Ft

    817 Gulf Rd, Barnard, VT 05031

    One of the best opportunities our firm has ever presented. 192 acres, mountain views, pond, stream and waterfall - and three dwelling structures plus many outbuildings, in desirable Barnard VT, just 13 minutes drive to Woodstock village green. This is an estate sale of the late owner. This land with the Old Dean House (a cape house on a pond) was purchased and owned by a prominent family in

    John Snyder Snyder Donegan Real Estate Group

    817 Gulf Rd, Barnard, VT 05031
  • /30

    $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 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. Built by Ennis Construction in 2015 on 68 acres, the three-bedroom home embodies the enduring appeal of timber frame architecture with soaring spaces, exposed fir beams, and

    Story Jenks LandVest, Inc/Woodstock

    115 Eastman Rd, Woodstock, VT 05091
  • /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
  • /58

    $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
  • /20

    $497,500

    • 3 Beds
    • 3 Baths
    • 2,268 Sq Ft

    121 Townhouse Way Unit 24, Woodstock, VT 05091

    Live Work Play, Retire and Play, or Just Play on the Weekends and Holidays!This wonderful 3 BR, 3 Bath Townhome/Condo has it all. Nestled in a small quiet wooded community less than 5 minutes from the Historic Woodstock Center and conveniently located within walking distance of Woodstock Union Middle & High School. It is also located only 30 minutes from Killington Ski Resort and Okemo Ski

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    121 Townhouse Way Unit 24, Woodstock, VT 05091
  • /60

    $1,699,000

    • 4 Beds
    • 4.5 Baths
    • 3,788 Sq Ft

    184 Hartland Hill Rd, Hartland, VT 05048

    Discover the possibilities at Wise Pines, an extraordinary 40± acre property in the heart of Hartland, Vermont, ideally located between Woodstock and Quechee. Surrounded by rolling hills, mature forests, and tranquil walking trails, this unique property was thoughtfully created as a sustainable wellness retreat and offers an exceptional opportunity for its next owner. Wise Pines began its journey

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    184 Hartland Hill Rd, Hartland, VT 05048
  • /30

    $799,000

    • 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
  • /60

    $1,695,000

    • 4 Beds
    • 3.5 Baths
    • 4,800 Sq Ft

    2706 E Woodstock Rd, Woodstock, VT 05091

    Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, upgraded systems, and fully furnished. Also included, is an additional 2,500+/- sq/ft (total) of an AirBNB rental/In-Law apartment, along with an active US Postal Service rental space, and generous storefront space in the former

    Agent Photo

    John Bassette

    Bassette Real Estate Group

    2706 E Woodstock Rd, Woodstock, VT 05091
  • /28

    $889,000

    • 3 Beds
    • 3.5 Baths
    • 2,383 Sq Ft

    5723 Vt Rt 12 Route, Barnard, VT 05031

    Beautifully renovated, this Barnard Village Cape seamlessly blends modern energy- efficient upgrades with the timeless charm of a classic New England home. A spacious slate-floored mudroom welcomes you into a bright, inviting interior featuring all-new Renewal by Andersen windows and beautifully restored original maple floors. The thoughtfully designed main level includes a stylish kitchen with

    Mary Mayhew Snyder Donegan Real Estate Group

    5723 Vt Rt 12 Route, Barnard, VT 05031
  • /58

    $569,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,924 Sq Ft

    530 West Rd, Barnard, VT 05031

    Set just up West Road in Barnard, this inviting Cape-style home offers a classic Vermont setting: a peaceful wooded backdrop, warm interior character, and easy access to village life, Silver Lake, and the outdoors. The Barnard General Store and Silver Lake, with the town hall, town library, and newly constructed fire station, are nearby. West Road also serves as a way to head toward the

    Eric Johnston Four Seasons Sotheby's Int'l Realty

    530 West Rd, Barnard, VT 05031
  • /31

    $449,000

    $16K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,268 Sq Ft

    121 Townhouse Way Unit 20, Woodstock, VT 05091

    Spacious, immaculate, and beautifully maintained Federal-style brick townhouse located in the prestigious village of Woodstock, often recognized as one of America’s most beautiful small towns. Three finished levels, the larger size residence of 24 homes. Surrounded by mature woods, perennial gardens, & maple trees. A peaceful setting just minutes from Woodstock Village. The Woodstock Farmers’

    Dorothea Mongulla High End Realty

    121 Townhouse Way Unit 20, Woodstock, VT 05091
  • /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
  • /60

    $2,225,000

    • 4 Beds
    • 3 Baths
    • 3,867 Sq Ft

    473 Kendall Rd, Woodstock, VT 05091

    Nestled in amongst flowering lilacs, ancient apple trees, and terraced English perennial gardens, this lovingly restored classic antique stone cape has all the conveniences of modern living, while honoring and preserving the charming period detail. Built in 1860, the home is an impressive example of snecked ashlar stone construction, which was introduced to this region by Scottish immigrants in

    Danny Kogut Williamson Group Sothebys Intl. Realty

    473 Kendall Rd, Woodstock, 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
  • /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
  • /58

    $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
  • /39

    $649,000

    $46K 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /11

    $229,000

    $20K PRICE DROP
    • Land
    • 57.2 Acres
    • $4,003 per Acre

    0 Masterson Unit 5080891, Barnard, VT 05031

    Discover 57.2 acres of exceptional forestland offering the perfect blend of privacy and convenience—tucked away yet less than half a mile from Vermont Route 12. This property provides an ideal setting for a private home or recreational retreat, with easy access to Barnard Village and Interstate 89. The recently cleared build site sits in a wonderful location above, yet not too far from Masterson

    Sophie Roya Berry Hill Real Estate

    0 Masterson Unit 5080891, Barnard, VT 05031
  • /43

    $3,750,000

    $500K PRICE DROP
    • 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
  • /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
  • /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
  • /59

    $379,000

    $10K PRICE DROP
    • 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 endless 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

    John Wetmore Wetmore Real Estate

    1821 Chateauguay Rd, Bethel, VT 05032
  • /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
  • /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
  • /26

    $465,000

    $30K 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
  • /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
  • /21

    $2,950,000

    $350K PRICE DROP
    • 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
  • /16

    $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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