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Windsor County VT 2-Story Homes for Sale

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  • /51

    $1,199,000

    • 5 Beds
    • 2.5 Baths
    • 2,662 Sq Ft

    63 Shiloh Ln, Norwich, VT 05055

    Tucked away on magical Shiloh Lane, this 21.5-acre property offers a peaceful, park-like setting with beautifully landscaped grounds, two potential pond sites, horse barn, greenhouse, garden space and trails. Step inside from the covered front porch or the stone patio and discover a thoughtfully cared for home filled with warmth and character. The 2023 kitchen renovation includes striking Mexican

    Agent Photo

    Melissa Robinson

    Coldwell Banker LIFESTYLES - Hanover

    (802) 810-8665

    63 Shiloh Ln, Norwich, VT 05055
  • /36

    $945,000

    • 4 Beds
    • 3.5 Baths
    • 3,650 Sq Ft

    126 Primrose Ln, Hartford, VT 05047

    126 PRIMROSE LANE- Spacious, well-built, and updated colonial in desirable location just a few minutes from the Quechee Club. A newer premium kitchen with direct access to a large west facing deck that wraps the back of the house, abutting great room with a vaulted ceiling centered around a beautiful stone fireplace, and a formal dining room adjacent the kitchen make for an ideal layout for

    David Donegan Snyder Donegan Real Estate Group

    126 Primrose Ln, Hartford, VT 05047
  • /16

    $425,000

    • 6 Beds
    • 4 Baths
    • 2,243 Sq Ft

    3 MacE Hill Rd, Hartland, VT 05048

    Strong Cash Flow! Profitable Investment Opportunity! This fully leased three unit multifamily property is an excellent chance for investors to add a consistent cash flowing property to their portfolio or for an onsite owner to occupy one unit and let the extra additional rents help pay for your housing. A low maintenance property with nice updates over the years which include separate electrical

    Alex DeFelice The Clerkin Agency, P.C.

    3 MacE Hill Rd, Hartland, VT 05048
  • /40

    $2,299,000

    • 6 Beds
    • 6 Baths
    • 7,619 Sq Ft

    5518 Vt Route 12, Barnard, VT 05031

    An historic brick residence prominently located in an affluent and growing community! Conveniently situated within walking distance to the Elementary School, to year round recreation on beloved Silver Lake and to the classic Barnard General Store. All the amenities of Woodstock Village are just minutes away! World class medical care at Dartmouth Hitchcock Hospital and year round cultural events

    John Wetmore Wetmore Real Estate

    5518 Vt Route 12, Barnard, VT 05031
  • /34

    $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
  • /31

    $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
  • /34

    $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
  • /35

    $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

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit A, Woodstock, VT 05091
  • /41

    $924,900

    • 3 Beds
    • 3 Baths
    • 3,392 Sq Ft

    117 Horseshoe Dr, Brownsville, VT 05037

    Experience Vermont living at its finest in this custom-built home, thoughtfully designed by the builder for exceptional energy efficiency and year-round comfort. Perfect as a relaxing getaway, this property offers expansive sleeping spaces ideal for hosting family and friends. Spend your days exploring the nearby VAST Trail system or Ascutney Mountain, and your evenings unwinding by the

    Katie Ladue Gilbert KW Vermont Woodstock

    117 Horseshoe Dr, Brownsville, VT 05037
  • /55

    $949,000

    • 5 Beds
    • 3 Baths
    • 2,807 Sq Ft

    157 Dartt Hill Rd, Bethel, VT 05032

    Nestled on 102 acres in Bethel, Vermont, this property offers the perfect blend of privacy, natural beauty, and functionality. Rolling pastures, wooded trails, and breathtaking Green Mountain views create a serene backdrop for everyday living or a weekend retreat. The land is well-suited for equestrian or hobby farming pursuits, featuring multiple open fields, a four-stall run-in barn, and a

    Eric Johnston Four Seasons Sotheby's Int'l Realty

    157 Dartt Hill Rd, Bethel, VT 05032
  • /53

    $1,495,000

    • 4 Beds
    • 3.5 Baths
    • 4,204 Sq Ft

    411 Wood Rd, Hartford, VT 05001

    Open House Sunday 10/12 from 11:00 to 1:00 - Set On 35 acres, This hilltop contemporary captures sweeping long-range views of the Quechee Valley, the Woodstock hills, and the Quechee Ski Hill. With over 4,000 sq. ft. of finely crafted living space, the home showcases quality throughout - custom trim, warm wood and tile floors, radiant heat, and walls of glass designed to frame Vermont’s beauty

    Sandy Reavill Real Broker LLC

    411 Wood Rd, Hartford, VT 05001
  • /38

    $795,000

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

    6077 Vt Route 12, Barnard, VT 05031

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

    David Donegan Snyder Donegan Real Estate Group

    6077 Vt Route 12, Barnard, VT 05031
  • /42

    $1,365,000

    • 5 Beds
    • 3.5 Baths
    • 3,925 Sq Ft

    18 Elm St, Norwich, VT 05055

    Charming Norwich Village Farmhouse Blending Historic Character with Modern ComfortLocated in the heart of Norwich Village, this timeless Vermont farmhouse—originally built in 1810—has been thoughtfully renovated to preserve its rich history while incorporating modern conveniences. From original exposed beams and antique doors to tucked-away nooks, every detail tells a story.The

    Julie Davis KW Vermont Woodstock

    18 Elm St, Norwich, VT 05055
  • /42

    $15,000,000

    • 5 Beds
    • 10 Baths
    • 9,679 Sq Ft

    3147 Mount Hunger Rd, Barnard, VT 05031

    Honey Hill Farm is a rare and distinguished Vermont estate, encompassing over 300 acres of pastoral beauty, panoramic mountain views, trails, and a spring-fed pond. The main residence has been masterfully reimagined with a full-scale renovation, marrying timeless craftsmanship with the highest standard of modern luxury. At its heart lies an expansive gourmet kitchen—designed with custom marble

    Keri Cole Williamson Group Sothebys Intl. Realty

    3147 Mount Hunger Rd, Barnard, VT 05031
  • /50

    $945,000

    • 3 Beds
    • 3 Baths
    • 3,362 Sq Ft

    150 Trombley Rd, Springfield, VT 05156

    Set on 104 scenic acres in Springfield, Vermont, 150 Trombly Road offers a rare combination of comfort, natural beauty, and agricultural potential. This three-bedroom, three-bath home features 3,362 square feet of inviting living space surrounded by open fields, wooded areas, and beautiful local mountain views. Perfect for equestrian or farming pursuits, the property includes a three-stall barn

    Kate Cassidy Four Seasons Sotheby's Int'l Realty

    150 Trombley Rd, Springfield, VT 05156
  • /17

    $825,000

    • 4 Beds
    • 1.5 Baths
    • 2,200 Sq Ft

    1928 Vermont 131, Springfield, VT 05156

    COUNTRY LIVING ON 118 ACRES WITH FULLY APPLIANCED, 4 BR's, 1.5 BATH HOME WITH ATTACHED GARAGE WITH 2ND FLOOR, A STATE-OF-THE ART PELLET BOILER, ROOF TOP SOLAR SYSTEM, SMALL POND, BARN AND STORAGE BUILDINGS. THE LAND BOAST ONE OF THE MOST BEAUTIFUL AND PLENTIFUL SUGAR BUSH IN THE STATE THAT EASILY ACCOMADATES OVER 4500 TAPS. SEVERAL WELL-MAINTAINED WOOD-LAND TRAILS TRAVERSE THE ACREAGE AND THE

    Don Chabot Town and Country Realty

    1928 Vermont 131, Springfield, VT 05156
  • /60

    $859,000

    • 2 Beds
    • 3 Baths
    • 2,250 Sq Ft

    60 Spencer Hollow Rd, Springfield, VT 05156

    *****OPEN HOUSE November 1st from 11am-1pm***** Experience timeless elegance and rural charm at this meticulously crafted country estate, featuring a historical reproduction Shaker-style home designed by renowned architect McKee Wing Roth and built in 1991. Set on 15 deeded acres of rolling pastures, this unique estate blends traditional design with modern sustainability. The main residence

    Kristen Breeden Southern Vermont Realty Group

    60 Spencer Hollow Rd, Springfield, VT 05156
  • /41

    $549,000

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    22 Rimrock Rd Unit 4B, Ludlow, VT 05149

    Affordable Okemo Trailside 3 bedroom plus den end unit. In great condition and ready to be your ski get-a-way this season. Updates include kitchen, main level bathroom and a brand new wood burning fireplace installed in the Fall of 2025. On 2 levels, there is an open kitchen/dining/living area, bath and bedroom on the main level, 2 bedrooms, bath, laundry and a cozy den finish the lower level.

    Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    22 Rimrock Rd Unit 4B, Ludlow, VT 05149
  • /40

    $1,295,000

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

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

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

    Chris Crowe Quechee Lakes Real Estate Center

    513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091
  • /56

    $795,000

    • 3 Beds
    • 2 Baths
    • 1,940 Sq Ft

    211 Wood Rd, Hartford, VT 05001

    100 ACRE WOODS!! - Complete turn-key package for vacation rentals and a second home. Tucked away on 96+ protected acres spanning Hartford/Quechee, and a portion of Hartland, this fully furnished 3-bedroom, 2-bath log home offers exceptional privacy, quiet, & year-round recreation....Including a robust (optional) rental program. The land has an existing subdivision in place if you ever decide to

    John Bassette Bassette Real Estate Group

    211 Wood Rd, Hartford, VT 05001
  • /35

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 2,736 Sq Ft

    17 Linden Hill, Wood Stock, VT 05091

    Open House! Saturday Oct 18 from 10-12. Once known as the Sunshine Nursery School, this home's history expands back to ~1870 and now it stands as a spacious and beautifully updated residence with an expansive terraced yard (one of the largest near the village) and elegant interiors. High ceilings, high-quality wood floors, and sun-filled rooms define the main level, where a gracious primary

    Holly Hall Hall Collins Real Estate Group

    17 Linden Hill, Wood Stock, VT 05091
  • /57

    $795,000

    • 5 Beds
    • 2 Baths
    • 2,500 Sq Ft

    1312 MacIntosh Hill Rd, Randolph, VT 05060

    Now offered at $795,000 – A Vermont farmhouse with a historic orchard, mountain views, and income potential. Set amid rolling hills and breathtaking mountain vistas, this classic Vermont farmhouse sits on one of the first Macintosh apple orchards in the country. Rich with history and surrounded by natural beauty, the property offers a rare blend of character, comfort, and opportunity. A

    Jason Saphire www.HomeZu.com

    1312 MacIntosh Hill Rd, Randolph, VT 05060
  • /57

    $1,150,000

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

    958 E Woodstock Rd, Woodstock, VT 05091

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

    Keri Cole Williamson Group Sothebys Intl. Realty

    958 E Woodstock Rd, Woodstock, VT 05091
  • /57

    $1,300,000

    • 4 Beds
    • 3 Baths
    • 2,892 Sq Ft

    145 Russell Rd, Cavendish, VT 05142

    Thinking of building your dream home, finding a perfect contractor & designer? Well skip the headaches. Move right in - Here are the keys! Tucked on 12.9 serene acres, custom built in 2024, this 4-bedroom, 3-bathroom amazing home combines expert craftsmanship and design with modern comfort and sweeping mountain VIEWS. Start your mornings with breathtaking vistas and end your evenings with family

    Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

    145 Russell Rd, Cavendish, VT 05142
  • /49

    $785,000

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

    37 South St, Woodstock, VT 05091

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

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    37 South St, Woodstock, VT 05091
  • /43

    $925,000

    • 4 Beds
    • 3.5 Baths
    • 2,970 Sq Ft

    1877 Willard Rd, Hartford, VT 05047

    Stunning Deck House perfectly designed for light, views, and easy Vermont living. Soaring floor-to-ceiling glass in the entryway and stairwell connects all levels and creates a warm, treehouse-like feel, drenched in natural light. Honey-colored hardwood floors warm the main level, while wall-to-wall carpet and tile finish the rest of the spaces. The main level also features a striking stone

    Derek Cosentino Four Seasons Sotheby's Int'l Realty

    1877 Willard Rd, Hartford, VT 05047
  • /11

    $1,350,000

    • 4 Beds
    • 3 Baths
    • 2,277 Sq Ft

    4074 Tichenor Rd Unit 4074, Hartford, VT 05059

    To be built, Mountain Stream at Quechee Lakes seamlessly integrates new construction with the natural beauty of Vermont's premier four-season resort community. Offering over 200 homesites and five distinct home styles, Mountain Stream’s residences feature modern, open layouts, abundant natural light, and soaring ceilings. The exclusive designs establish a commitment to sustainable,

    Richard Higgerson Higgerson & Company

    4074 Tichenor Rd Unit 4074, Hartford, VT 05059
  • /55

    $747,000

    • 6 Beds
    • 5 Baths
    • 3,000 Sq Ft

    221 Grout Rd, Perkinsville, VT 05151

    Price reduced! The VT property that you have been waiting for! 49 acres with mature sugar maples and stone walls, a substantial converted barn and a lovely updated and expanded C. 1790 residence. Former home of the Weathersfield Rod and Gun Club, it has been thoroughly renovated into a grand residence. Five bedrooms and five baths, including a guest space with separate entry. Gracious country

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    221 Grout Rd, Perkinsville, VT 05151
  • /52

    $765,000

    • 4 Beds
    • 3.5 Baths
    • 2,828 Sq Ft

    119 Pine Hill Rd, Ludlow, VT 05149

    Nestled in the desirable Okemo Pines community, this 4-bedroom, 3.5-bath home offers the perfect blend of comfort, charm, and convenience, only minutes from Okemo Mountain Resort. Thoughtfully designed for year-round enjoyment, the home features multiple seasonal living areas, including a large deck with Okemo views, a sunroom, and a covered porch with mountain views. The house offers privacy

    Joseph Karl William Raveis Real Estate Vermont Properties

    119 Pine Hill Rd, Ludlow, VT 05149
  • /36

    $895,000

    • 3 Beds
    • 5 Baths
    • 3,590 Sq Ft

    1104 Main St, Cavendish, VT 05142

    Situated on the bank of the Black River at the edge of the Village Of Proctorsville is this three bedroom all ensuite, 5 bath log home. The Great Room boasts a floor to cathedral ceiling wood burning fireplace where you can sit and relax after a day on the slopes. Then take in river views from the formal dining room. Also on the first floor is a primary ensuite. Upstairs the huge lofted area is

    Frank Provance Diamond Realty

    1104 Main St, Cavendish, VT 05142
  • /57

    $817,000

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

    616 Rose Hill Rd, Woodstock, VT 05091

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

    Carol Wood Williamson Group Sothebys Intl. Realty

    616 Rose Hill Rd, Woodstock, VT 05091
  • /45

    $985,000

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

    72 Oakridge Way, Woodstock, VT 05091

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

    Nancy Greenwood Watson Realty & Associates

    72 Oakridge Way, Woodstock, VT 05091
  • /46

    $745,000

    • 5 Beds
    • 2.5 Baths
    • 2,717 Sq Ft

    1134 Route 106, Reading, VT 05062

    Timeless Stone Estate on 36 Acres with Modern Comforts & Rustic Elegance. Welcome to your private countryside retreat—an extraordinary 36-acre estate where historic charm meets modern-day living. Built in the 1800s and thoughtfully updated, this 5-bedroom, 2.5-bath stone home offers the kind of setting most only dream of: expansive rolling land, a private pond and multiple outbuildings for all

    Kevin Barnes William Raveis Real Estate Vermont Properties

    1134 Route 106, Reading, VT 05062
  • /60

    $825,000

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

    7137 Us Route 4, Bridgewater, VT 05034

    The historic Bridgewater Inn consists of a 3-bedroom, 3-bath spacious home excellent for families or groups. The home has two covered porches, a large eat-in kitchen, living room with gas fireplace and two game rooms. The house has new furniture, paint and floors along with new flush mounted mini splits.Attached are 4 turnkey suites with entrances separate form the home. The property is

    Laura Derderian Killington Valley Real Estate

    7137 Us Route 4, Bridgewater, VT 05034
  • /50

    $895,000

    • 4 Beds
    • 2.5 Baths
    • 2,044 Sq Ft

    100 Pomfret Rd, Woodstock, VT 05091

    Charming, Unique, and Ideally Located! Welcome to 100 Pomfret Road—a beautifully updated farmhouse set on four level, picturesque acres just a short walk from Mt. Tom, Billings Farm, and the heart of downtown Woodstock. This rare find blends timeless character with everyday convenience in a peaceful, brookside setting.Inside, you’ll find a sun-drenched home featuring four

    Keri Cole Williamson Group Sothebys Intl. Realty

    100 Pomfret Rd, Woodstock, VT 05091
  • /7

    $126,000

    • 6 Beds
    • 3 Baths
    • 2,377 Sq Ft

    6 Crescent St, Springfield, VT 05156

    This nicely laid out Two family plus carriage house has great potential! With key updates like updated roofing and double paned vinyl windows in the second floor unit. The carriage house boasts much potential with new siding materials on sight and currently the interior is being worked on for a renter that is already in place.

    Thaddeus Abare Barrett and Valley Associates Inc.

    6 Crescent St, Springfield, VT 05156
  • /9

    $249,000

    • 8 Beds
    • 4 Baths
    • 3,312 Sq Ft

    715 Giddings St, Springfield, VT 05150

    This Unique property features a large 3 unit building all featuring 2 bedrooms and 1 bathroom, with an additional carriage house with 2 bedrooms and 1 bathroom aswell. With a new heating system replaced in 2023 and many other key updates.

    Thaddeus Abare Barrett and Valley Associates Inc.

    715 Giddings St, Springfield, VT 05150
  • /7

    $249,000

    • 7 Beds
    • 4 Baths
    • 3,294 Sq Ft

    57 River St, Springfield, VT 05156

    This great property has a great central location in walking distance to downtown Springfield featuring all of the local amenities. The property overlooks the Black River and with good maintenance history on all systems this has the potential to be a great investment.

    Thaddeus Abare Barrett and Valley Associates Inc.

    57 River St, Springfield, VT 05156
  • /7

    $186,000

    • 6 Beds
    • 4 Baths
    • 2,304 Sq Ft

    51 Merrill St, Springfield, VT 05156

    This great property has so much to offer! With a large and expansive bottom floor unit featuring 3 bedrooms and 2 bathrooms with in unit laundry and a primary suite. Moving upstairs there is a great 2 bedroom 1 bathroom unit and adjacent to that unit is a 1 bed 1 bath unit. With an updated roof in 2020 and a newer heating unit that was put in in 2017.

    Thaddeus Abare Barrett and Valley Associates Inc.

    51 Merrill St, Springfield, VT 05156
  • /37

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    143 Spoonerville Rd, Springfield, VT 05150

    Are you looking for a home with a large open yard, a stream that runs along the property line, a treehouse, and a garage? If so, this updated home is waiting for you! The breezeway (also a finished mudroom) enables you to stay dry in the Vermont weather when you park in the garage. Power lines? Not here, as they are all buried. Many improvements have been made since purchasing, including new

    Heather Gleim CENTURY 21 North East

    143 Spoonerville Rd, Springfield, VT 05150

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