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Windsor County VT Homes for Sale

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  • /55

    $1,595,000

    Open Sat 11AM - 1PM Coming Soon
    • 5 Beds
    • 5.5 Baths
    • 3,521 Sq Ft

    2615 North Rd, Barnard, VT 05031

    At 2615 North Road, the landscape is ever-present. Expansive decks and walls of windows invite the mountains into everyday life, from the first light across the hills to the rich colors of a Vermont sunset. Set along one of Barnard’s most coveted roads, this fully renovated five-bedroom, 5.5-bath home brings a sophisticated point of view to country living...beautifully considered, effortlessly

    Agent Photo

    Susan Hickey

    Snyder Donegan Real Estate Group

    2615 North Rd, Barnard, VT 05031
  • /43

    $419,900

    $5K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,982 Sq Ft

    176 Meadow Rd, Chester, VT 05143

    Welcome to this beautifully updated raised ranch, thoughtfully designed for both relaxed day-to-day living and effortless entertaining. Step inside to an open-concept main level bathed in natural light, anchored by rich hickory hardwood floors that flow throughout. At the heart of the home, the renovated kitchen shines with modern finishes, a classic apron-front farmhouse sink, and stainless

    Agent Photo

    Lauren Behm

    Berkshire Hathaway HomeServices Stratton Home

    176 Meadow Rd, Chester, VT 05143
  • /40

    $259,000

    • 3 Beds
    • 1 Bath
    • 1,489 Sq Ft

    32 Mark St, Springfield, VT 05156

    More photos are coming! This home has been loved and cared for 50 plus years by the same family and now it is ready for a new chapter. Located in a nice family friendly neighborhood that is perfect for evening strolls around the block. Home features newer windows, hardwood floors, a heated sunroom, and a large dining room. The living room flows nicely into the heated sunroom for lots of

    Agent Photo

    Julie Buffum

    Buffum Realty

    32 Mark St, Springfield, VT 05156
  • /17

    $75,000

    • 2 Beds
    • 1 Bath
    • 620 Sq Ft

    1144 Potash Brook Rd, Chester, VT 05143

    Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced with a permanent structure. Power, septic and electric on sight along with a 1 car garage. Home could be repaired, would also make a great spot for a snowbird wanting a spot in Vermont or anyone looking to park an RV. Property is sold AS IS CASH ONLY

    Agent Photo

    Julie Buffum

    Buffum Realty

    1144 Potash Brook Rd, Chester, VT 05143
  • /12

    $149,000

    • Land
    • 17.7 Acres
    • $8,418 per Acre

    0 Trebo Rd, Chester, VT 05143

    Discover the perfect setting for your Vermont dream home or future development on this picturesque rural parcel. Set along scenic Trebo Road, a quiet country road lined with historic homes, open fields, and mature woodlands, this nearly 18-acre property offers exceptional potential. Highlights include approximately 1,500 feet of road frontage, a charming pond, beautiful stone walls, and a Vermont

    Agent Photo

    Gail Beardmore

    Engel & Völkers Okemo

    0 Trebo Rd, Chester, VT 05143
  • /42

    $850,000

    Coming Soon
    • 4 Beds
    • 2 Baths
    • 2,352 Sq Ft

    208 Jarvis Rd, Perkinsville, VT 05151

    Delayed showings until 8/16. Motivated Seller! This exceptional four-bedroom home encompasses 11.5 pristine acres. The residence features light-filled, elegantly scaled principal rooms optimized for entertaining and daily living. There is a study/bedroom on the first floor with a three-quarter hall bath next to it. Upstairs, there are three bedrooms (one is being used as a study) and a generously

    Agent Photo

    Jennifer Falvey

    KW Vermont Woodstock

    208 Jarvis Rd, Perkinsville, VT 05151
  • /60

    $475,000

    $20K PRICE DROP
    • 3,036 Sq Ft

    7868 Pomfret Rd, North Pomfret, VT 05053

    CASH FLOW POSITIVE - GREAT VALUE! A rare opportunity to own a piece of Vermont history - The North Pomfret Store & Post Office, c.1830. This 3-story New Englander offers charm, character, and a solid income stream on 1.84 picturesque acres. With 5 total units, the property includes 3 residential apartments (one 2-bedroom, one 1-bedroom, and an Efficiency), a ground-floor commercial office space,

    Agent Photo

    John Bassette

    Bassette Real Estate Group

    7868 Pomfret Rd, North Pomfret, VT 05053
  • /2

    $129,000

    $10K PRICE DROP
    • 2,144 Sq Ft

    73 Union St, Springfield, VT 05156

    Nice sized in-town home and yard with large 2 car garage and shed. Lots of room for your toys. The home is currently a 2-unit home but was originally a single-family home and could be changed back into a one family without a lot of effort. Home does need some work so cash buyers only please. This could be your chance to get into rental business. Lots of possibilities for this home.Home is

    Agent Photo

    Julie Buffum

    Buffum Realty

    73 Union St, Springfield, VT 05156
  • /47

    $1,595,000

    $300K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,708 Sq Ft

    196 Cowdrey Outlook, Bethel, VT 05032

    For the first time in over half a century, this extraordinary 100+ acre estate-level property in Barnard is being offered for sale. Cherished by the same family for generations, the property presents a rare opportunity to own one of Vermont’s most scenic and versatile landscapes. Commanding long-range mountain views define the setting, while several picturesque spring-fed ponds, rolling meadows,

    Agent Photo

    Susan Hickey

    Snyder Donegan Real Estate Group

    196 Cowdrey Outlook, Bethel, VT 05032
  • /43

    $699,000

    • 2 Beds
    • 3 Baths
    • 1,364 Sq Ft

    193 Jackson Gore Unit 739/741, Ludlow, VT 05149

    Come and experience Vermont at its best! This condo is located in Jackson Gore on Okemo Mountain in Ludlow. This slope side condo unit has stunning views of the mountain and trails. This unit would serve well as a family retreat or rental investment property. It boasts a gas fireplace for cold winter nights. It has 2 bedrooms and 3 bathrooms and offers lock-out capability for separate rental

    Agent Photo

    John Napier

    TPW Real Estate

    193 Jackson Gore Unit 739/741, Ludlow, VT 05149
  • /39

    $949,000

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,183 Sq Ft

    63 Royall Tyler Rd, Hartford, VT 05001

    Settle into the farmers porch with a morning coffee and watch the seasons change across the Vermont hills. Inside, every detail speaks to quality craftsmanship — thoughtful appointments, warm finishes, and a layout designed for real family life. The yard has plenty of room for kids to run, explore, and make the kind of memories that bring families back to Vermont generation after

    Agent Photo

    Herb Hart

    Quechee Lakes Real Estate Center

    63 Royall Tyler Rd, Hartford, VT 05001
  • /3

    $170,000

    • Land
    • 10.04 Acres
    • $16,932 per Acre

    00 Will Dean Rd, Springfield, VT 05156

    Nice piece of land with some selected clearing done but more could be done with the potential of views. Land is both clear and wooded, level and sloping. Located on a quiet gravel road with a mix of single-family homes and small farms it is the perfect reflection of rural Vermont. Just minutes to I91and downtown Springfield makes this a great spot to set down roots.

    Agent Photo

    Julie Buffum

    Buffum Realty

    00 Will Dean Rd, Springfield, VT 05156
  • /24

    $89,000

    • 2 Beds
    • 2 Baths
    • 980 Sq Ft

    23 Family Cir, Hartland, VT 05001

    Affordable, low-maintenance living in a convenient Hartland location! This well-cared-for 1997 mobile home in Dales Homes Mobile Home Park offers 2 bedrooms, 2 full bathrooms, and a bright, comfortable layout. The home features a spacious living room, an eat-in kitchen, and a primary bedroom with a private bath. A paved driveway, attached carport, and storage shed provide added convenience and

    Agent Photo

    Melissa Robinson

    Coldwell Banker LIFESTYLES - Hanover

    23 Family Cir, Hartland, VT 05001
  • /29

    $469,000

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

    167 Chestnut St, Hartford, VT 05001

    Freshly painted inside and out, this beautifully renovated New Englander in Wilder Village blends timeless charm with modern updates, including a new roof, boiler, updated electric service, many new appliances, hardwood floors, and an upstairs washer and dryer. Situated on a rare, level 0.73-acre double lot with three garage bays, the property is just a short walk to the Connecticut River and

    Agent Photo

    Jeff Fogg

    Black House Real Estate

    167 Chestnut St, Hartford, VT 05001
  • /6

    $299,000

    • Land
    • 116.2 Acres
    • $2,573 per Acre

    00 Grout Rd, Weathersfield, VT 05153

    A large private parcel of land located in Cavendish on the Weathersfield line. This 116+- acres is a mix of woods and cleared areas that has beautiful mountain views that can be accessed from Grout road. There is road frontage on scenic vermont route 131 that can access the land with grading. These 2 lot have been surveyed and there are multiple possible building sites. This property is close to

    Agent Photo

    John Napier

    TPW Real Estate

    00 Grout Rd, Weathersfield, VT 05153
  • /30

    $75,000

    • 1,440 Sq Ft

    178 Church St, Bethel, VT 05032

    Looking for a Summer Project? Put your ambition and skills to work in this unfinished, single-story 30' x 24'+ wood framed shell constructed with beefy rough-cut lumber. Electric service provided by Green Mountain Power (meter on building). Public water service to, and public sewage disposal from, are available on site. Currently, there is no electrical wiring, plumbing pipes, nor fixtures, but

    Agent Photo

    Lori Holt

    BHHS Vermont Realty Group/Montpelier

    178 Church St, Bethel, VT 05032
  • /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
  • /59

    $1,690,000

    • 10 Beds
    • 8 Baths
    • 7,566 Sq Ft

    156 Main St, Ludlow, VT 05149

    In the heart of the ever-popular Ludlow, Vermont, sits an 11,409 square foot commercial building with 7,566 square feet of finished space. Built in 1990, it is situated in a prime location on Main Street in the center of the village providing it with excellent visibility, walkability, and proximity to Ludlow’s charming boutiques and local dining. It is full of investment possibilities with seven

    Agent Photo

    John Napier

    TPW Real Estate

    156 Main St, Ludlow, VT 05149
  • /49

    $2,195,000

    • 3 Beds
    • 3 Baths
    • 2,997 Sq Ft

    9671 Vt Route 12, Barnard, VT 05031

    SPRING HILL FARM – A Storied Vermont Estate with Timeless Appeal. Set amidst the rolling hills of Barnard, Vermont, Spring Hill Farm is a distinguished country estate where historic charm and thoughtful stewardship come together across 207 acres of beautifully maintained landscape. Anchoring the property is a stately brick residence dating to 1795, offering a refined sense of heritage and

    Agent Photo

    Susan Hickey

    Snyder Donegan Real Estate Group

    9671 Vt Route 12, Barnard, VT 05031
  • /30

    $279,000

    • 3 Beds
    • 1 Bath
    • 1,331 Sq Ft

    139 Pleasant Valley Rd, Springfield, VT 05156

    Original 1800's cape style home situated conveniently between Springfield and Chester. Home has seen updates over the years but continues to show original charm of an 1800's period home, exposed beams in primary bedroom, mixed wood floors, post and beam shed/garage with usable and accessible second floor. The enclosed front porch leads you to the comfortable, sunlit eat in country kitchen which

    Agent Photo

    Julie Buffum

    Buffum Realty

    139 Pleasant Valley Rd, Springfield, VT 05156
  • /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

    Agent Photo

    Jennifer Falvey

    KW Vermont Woodstock

    41 Pleasant St, Woodstock, VT 05091
  • /52

    $499,000

    $200K PRICE DROP
    • 2.5 Baths
    • 7,445 Sq Ft

    66 Duttonsville School Dr, Cavendish, VT 05142

    Where History Meets Possibility. An 1862 Schoolhouse Reimagined. Step back in time and into opportunity. Built in 1862, this remarkable historic schoolhouse has been lovingly preserved, its character and craftsmanship thoughtfully maintained while seamlessly supporting modern use.Since 1973, the building has served as the home of a thriving distribution business, proof of its adaptability,

    Agent Photo

    Gail Beardmore

    Engel & Völkers Okemo

    66 Duttonsville School Dr, Cavendish, VT 05142
  • /60

    $500,000

    Open Thu 5PM - 7PM
    • 4 Beds
    • 4 Baths
    • 960 Sq Ft

    544 Vulture Mountain Rd, Stockbridge, VT 05772

    Welcome to Camp Treetops, a one-of-a-kind mountaintop estate perched high above the White River Valley. This fully operating, high-performing retreat conveys COMPLETELY FURNISHED and turnkey, with panoramic mountain and White River views, total privacy, and a proven income stream already in place. At its heart is the original Sears Roebuck kit hunting cabin, beautifully renovated with warm wood

    Agent Photo

    Jacob Barnes

    EXP Realty

    544 Vulture Mountain Rd, Stockbridge, VT 05772
  • /58

    $1,350,000

    $50K PRICE DROP
    • 6 Beds
    • 5 Baths
    • 4,571 Sq Ft

    505 Deweys Mills Rd, Hartford, VT 05047

    The Dewey House joins timeless elegance with contemporary convenience. Situated on a quiet road adjacent to the Quechee Gorge waterfall in the charming town of Quechee, this property offers easy access to I-89, I-91, and Route 4. Nearby walking trails and direct water access lend themselves to outdoor pursuits, while the views from the house and its decks over the mill pond and hills create the

    Agent Photo

    Jennifer Falvey

    KW Vermont Woodstock

    505 Deweys Mills Rd, Hartford, VT 05047
  • /2

    $54,900

    • Land
    • 3 Acres
    • $18,300 per Acre

    00 Comstock Ave, Weathersfield, VT 05030

    3.00 +/- lot located just minutes from I91, Claremont, Windsor, Springfield and the upper valley. If you have been looking for an untouched piece of land this is your opportunity.

    Agent Photo

    Julie Buffum

    Buffum Realty

    00 Comstock Ave, Weathersfield, VT 05030
  • /26

    $249,000

    • 3 Beds
    • 1 Bath
    • 1,203 Sq Ft

    42 Mark St, Springfield, VT 05156

    Delightful cape style home in a family friendly neighborhood. Large lot with detached single car garage, additional building for storage, lots of level space for a garden or to fence in. Home features a covered entry. This home has seen lots of updates thru its life including a newer roof, new wooden siding that has been freshly painted, interior of the home has also been freshly painted. Lots of

    Agent Photo

    Julie Buffum

    Buffum Realty

    42 Mark St, Springfield, VT 05156
  • /37

    $399,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,148 Sq Ft

    40 Fenton Rd, Chester, VT 05143

    This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of

    Agent Photo

    John Napier

    TPW Real Estate

    40 Fenton Rd, Chester, VT 05143
  • /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
  • /50

    $1,399,000

    $49K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    145 the Plateau, Windsor, VT 05089

    "The Plateau", originally part of the Kennedy Biscuit Co. (Nabisco) family estate, is nestled on a plateau at the end of a private road which greets you with open fields, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two

    Dan Noble Snyder Donegan Real Estate Group

    145 the Plateau, Windsor, VT 05089
  • /59

    $3,500,000

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

    56 Cream Pot Rd, Hartland, VT 05048

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

    David Donegan Snyder Donegan Real Estate Group

    56 Cream Pot Rd, Hartland, VT 05048
  • /58

    $450,000

    $25K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,865 Sq Ft

    81 Main St, Chester, VT 05143

    Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning

    Betsy Adamovich Real Broker LLC

    81 Main St, Chester, VT 05143
  • /28

    $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
  • /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
  • /60

    $2,200,000

    $295K PRICE DROP
    • 5 Beds
    • 9 Baths
    • 7,322 Sq Ft

    1497 Bowman Rd, Barnard, VT 05068

    Circa 1799 Vermont cape, thoughtfully restored and expanded to over 7,300 finished square feet on 12.5 private acres, minutes to Silver Lake and Woodstock village. Five bedrooms, nine baths, and a layout that balances everyday living with the ability to host. Original materials carry throughout, including wide pine floors, skim-coat plaster walls, hand-carved paneling, and period hardware, giving

    Richard Higgerson Higgerson & Company

    1497 Bowman Rd, Barnard, VT 05068
  • /57

    $1,450,000

    • 3 Beds
    • 3 Baths
    • 1,836 Sq Ft

    144 Lodge Rd Unit 1, Ludlow, VT 05149

    Welcome to South Face Village! True slopeside living at its best. This front-row, ski-in/ski-out 3-bedroom, 3-bath condo is literally on the slope. Walk out your front door, plop your skis or board down and head to the Sunshine lift. This gives you direct access to the South Face Express Quad. Inside this immaculate, turnkey unit is everything you'll want in your mountain château. Step in take

    Frank Provance Diamond Realty

    144 Lodge Rd Unit 1, Ludlow, VT 05149
  • /58

    $2,900,000

    $200K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,843 Sq Ft

    66 Hollow Farm Rd, Woodstock, VT 05071

    CURTIS HOLLOW FARM, Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows

    David Donegan Snyder Donegan Real Estate Group

    66 Hollow Farm Rd, Woodstock, VT 05071
  • /44

    $824,900

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,392 Sq Ft

    117 Horseshoe Dr, Brownsville, VT 05037

    Experience the best of Vermont living in this custom-built home in desirable West Windsor, where thoughtful craftsmanship, energy efficiency, and four-season recreation come together. Designed and built by its original builder, this home offers exceptional quality, low-maintenance living, and comfortable year-round enjoyment. Whether you're searching for a primary residence, a Vermont vacation

    Katie Ladue Gilbert BHHS Verani Upper Valley

    117 Horseshoe Dr, Brownsville, VT 05037
  • /28

    $849,900

    $39K PRICE DROP
    • 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
  • /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

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