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Windsor County VT Homes for Sale

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  • /45

    $1,150,000

    • 5 Beds
    • 3 Baths
    • 3,065 Sq Ft

    240 Ghia Farm Rd, Ludlow, VT 05149

    Located just a few minutes walk from Okemo's Sachem trail, this two family spacious 5-bedroom, 3-bathroom multi-level home offers exceptional flexibility for year-round living, vacationing, or hosting family and friends. Lovingly owned for almost 30 years, this home is designed with a versatile multi-family layout. Each level provides its own inviting living space while maintaining the warmth and

    Joseph Karl William Raveis Real Estate Vermont Properties

    240 Ghia Farm Rd, Ludlow, VT 05149
  • /47

    $1,475,000

    $174K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,456 Sq Ft

    140 Echo View Dr, Ludlow, VT 05149

    New construction, exceptional scale, and a location designed for enjoying everything the Okemo Valley has to offer. Set on 2.21 private acres just minutes from Okemo and within easy reach of Killington, this striking contemporary residence offers 3,456 square feet of thoughtfully designed living space with the comfort and amenities expected of a luxury mountain home.The main level makes

    Mendi Michael Engel & Völkers Okemo

    140 Echo View Dr, Ludlow, VT 05149
  • /27

    $300,000

    • 2 Beds
    • 2 Baths
    • 994 Sq Ft

    894 E Ash Rd Unit L-9, Plymouth, VT 05056

    Fully renovated and tastefully appointed with Crate & Barrel furnishings, this turnkey Hawk Ledges condominium offers an easy-care Vermont getaway. Modest in size yet thoughtfully designed, it features two bedrooms, each with a private bath, a welcoming stone fireplace and convenient exterior storage. Explore Hawk’s extensive trail network right outside your door, swim at nearby Plymouth State

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    894 E Ash Rd Unit L-9, Plymouth, VT 05056
  • /36

    $579,000

    • 3,124 Sq Ft

    7015 US Route 4, Bridgewater, VT 05034

    Prime investment opportunity minutes to the Killington Skyeship Base Lodge/Gondola and the beautiful Village of Woodstock. This wonderful, lovingly maintained two unit home with loads of charm, light, high ceilings, and gorgeous wood floors is a must see. The 3 bedroom unit is the front portion of the home with a great kitchen, laundry area, spacious living room for family and friends to hang out

    Marni Rieger KW Vermont-Killington

    7015 US Route 4, Bridgewater, VT 05034
  • /48

    $415,000

    $85K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,558 Sq Ft

    501 Stoughton Pond Rd, Perkinsville, VT 05151

    Tucked into the charming village of Perkinsville on 3.8 acres, this unique residential and commercial property offers the perfect balance of opportunity, lifestyle, and connection. You will be moments away from Stoughton Pond, hiking trails, and within driving distance to some of Vermont’s most sought-after ski resorts. For years, this property has been a gathering place, Saturday nights around

    Marie Potter EXP Realty

    501 Stoughton Pond Rd, Perkinsville, VT 05151
  • /54

    $449,000

    • 3 Beds
    • 1 Bath
    • 1,242 Sq Ft

    23 Biscuit Hollow Rd, Woodstock, VT 05091

    This nicely updated ranch on a country acre is a rare opportunity to live in Woodstock without breaking the bank. Perfect for downsizing, one-level living, starting out, or even an easy-to-care for vacation home. There is plenty of storage for skis or other recreation equipment in the oversized two-plus car garage and two bay shed with a concrete floor. Sellers have spent 12 years gradually

    Tambrey Vutech KW Vermont Woodstock

    23 Biscuit Hollow Rd, Woodstock, VT 05091
  • /32

    $309,000

    $25K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 599 Sq Ft

    350 Mountain Rd Unit B303, Ludlow, VT 05149

    Fabulous ski-in/ski-out opportunity at the base of Okemo Mountain! This top-floor (3rd level) one-bedroom, one-bath condominium offers unbeatable convenience and beautiful views overlooking the Okemo Base Lodge and the A-B chair lifts. With a sleeper sofa for additional guests, it’s the perfect Vermont retreat for weekend getaways or extended stays. A new electric fireplace provides ambiance and

    McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

    350 Mountain Rd Unit B303, Ludlow, VT 05149
  • /55

    $3,975,000

    • 4 Beds
    • 6.5 Baths
    • 6,450 Sq Ft

    4777 Rush Meadow Rd, West Windsor, VT 05089

    Sheep Run Farm takes its name from the stone-walled lanes where a prosperous 19th-century farmer once moved his sheep between the barn and upper meadows. Nearly two centuries later, those walls still trace the landscape, framing a beautifully reimagined Vermont farmstead on 21± acres in West Windsor, 3 miles from South Woodstock and 8 miles from Woodstock Village.Drawing on the

    Dia Jenks LandVest, Inc/Woodstock

    4777 Rush Meadow Rd, West Windsor, VT 05089
  • /48

    $549,500

    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft

    1043 Town Farm Rd, Ludlow, VT 05149

    Discover the quintessential Vermont mountain getaway at this inviting 3 bedroom, 2-bath South Hill home, offered fully furnished and turnkey with a proven short-term rental history. Whether you’re looking for a private retreat, an income-producing property, or the best of both, this home is ready to enjoy from day one.Set in the heart of the Okemo Valley, the location offers exceptional

    Mendi Michael Engel & Völkers Okemo

    1043 Town Farm Rd, Ludlow, VT 05149
  • /49

    $535,000

    $15K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 2,727 Sq Ft

    1787 Route 100 N, Ludlow, VT 05149

    From location to layout, this home offers the best of Vermont living. Set along scenic Route 100 in the heart of the lakes region, you’ll enjoy year-round recreation just minutes from Okemo Mountain Resort, Killington Resort, and Plymouth State Park. This thoughtfully remodeled farmhouse blends classic charm with modern updates. Offering 3 bedrooms and 4 bathrooms, the home features generous

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    1787 Route 100 N, Ludlow, VT 05149
  • /12

    $389,000

    • Land
    • 4.73 Acres
    • $82,241 per Acre

    5209 Willard Rd, Hartford, VT 05059

    A thoughtfully assembled 4.73-acre homesite in Quechee Lakes’ Upper Willard Road neighborhood. Created from two combined lots, this property offers uncommon scale, privacy, and flexibility in one of the area’s more established settings. The land has been carefully curated by the current owner to take advantage of the natural Vermont landscape, with a mix of wooded surroundings and potential

    Richard Higgerson Higgerson & Company

    5209 Willard Rd, Hartford, VT 05059
  • /33

    $600,000

    $50K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,674 Sq Ft

    5863 Vermont Route 14, Royalton, VT 05068

    Dunrovin Manor is located at probably the most active area intersection, just off Exit 3, Royalton, Vt. Overlooking both the White River and Second Branch, this attractive older home is convenient to Vermont Law School and the quaint village of S. Royalton. Let the tenants pay your mortgage, while you occupy the main central area and open up the apartments. Annual projected net income to be

    Dean Goulet Dunrovin Real Estate

    5863 Vermont Route 14, Royalton, VT 05068
  • /33

    $264,900

    $15K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    572 Roberts Rd, Springfield, VT 05156

    *Back on the market due to buyer's financing* This contemporary, newly built, energy-efficient home is truly turn-key and ready for its new owners! This thoughtfully designed 700 sq. ft. tiny home was lovingly constructed with high-quality, eco-friendly materials, offering lasting durability and low-maintenance living. Inside, you'll find an inviting open-concept kitchen, living, and dining area,

    Chelsea Richardson Barrett and Valley Associates Inc.

    572 Roberts Rd, Springfield, VT 05156
  • /34

    $379,000

    $16K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 884 Sq Ft

    145 Okemo Trailside Extension Unit 23 B-L, Ludlow, VT 05149

    Recently updated large one-bedroom condominium at Trailside Village within easy walking distance to ski on / ski off access to the Sachem Trail.The open kitchen flows seamlessly into a separate dining area, creating a comfortable space for everyday living or entertaining. A sunken living room features a newly replaced wood-burning fireplace and new carpeting, offering a warm and inviting

    McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

    145 Okemo Trailside Extension Unit 23 B-L, Ludlow, VT 05149
  • /50

    $269,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,229 Sq Ft

    119 Merrill St, Springfield, VT 05156

    GOOD NEWS! A newly renovated, affordable, well maintained home for a reasonable price! Ask your agent for the list of improvements. It is expected that this home will EASILY MEET GOV'T LOAN FINANCING. This attractive home has easy access to downtown, shopping, parks, ski slopes, mountain hiking, river walks, interstate, and quiet living. The pleasantly comfortable yard offers reasonable privacy

    James Shibles Covered Bridge RE

    119 Merrill St, Springfield, VT 05156
  • /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
  • /48

    $795,000

    • 2 Beds
    • 3 Baths
    • 1,304 Sq Ft

    35 White Loop Unit B301, Ludlow, VT 05149

    Enjoy the best of the Okemo lifestyle at Winterplace B301, a tastefully updated slopeside condominium offering beautiful long-range mountain views and excellent rental potential. This inviting top-floor residence features two bedrooms plus a spacious loft, providing plenty of room for family and guests. The primary bedroom, second bedroom, and loft area each enjoy access to a private en-suite

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    35 White Loop Unit B301, Ludlow, VT 05149
  • /60

    $299,000

    • 2 Beds
    • 1 Bath
    • 1,152 Sq Ft

    466 Estey Ln, Windsor, VT 05089

    Embrace the ultimate Vermont lifestyle with this 1950s ranch, perfectly situated on 6.8 sprawling acres of versatile land at 466 Esty Lane in Windsor. Combining nostalgic mid-century charm with extraordinary future potential, this property is an absolute dream for investors, developers, or anyone looking to build their ideal country homestead. The existing home offers 1,152 square feet of

    Francis Duffy

    466 Estey Ln, Windsor, VT 05089
  • /39

    $399,000

    $51K PRICE DROP
    • Land
    • 251.5 Acres
    • $1,586 per Acre

    0 Peavine Blvd Unit 5046570, Bethel, VT 05032

    Discover a rare opportunity to own 253 acres of Vermont's finest landscape,encompassing a stunning blend of mature hardwood forest, open meadows, scenic overlooks, and long distant mountain views. This legacy property has been stewarded by the same family for generations, with the primary parcel held for more than 100 years. For the first time in four generations this exceptional acreage is

    Terry Davis Williamson Group Sothebys Intl. Realty

    0 Peavine Blvd Unit 5046570, Bethel, VT 05032
  • /48

    $1,795,000

    • 4 Beds
    • 3.5 Baths
    • 4,441 Sq Ft

    55 Stagecoach Rd, Norwich, VT 05055

    This meticulous & well cared for home welcomes your family and friends with its stately front porch designed by Anne Wilson. The main level is a terrific place for entertaining with large open rooms, 9’ ceilings, radiant heat, crown moldings, an abundance of windows and natural light, handsome fireplace, and lovely oak flooring throughout. Open the french doors to a comfortable private deck

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    55 Stagecoach Rd, Norwich, VT 05055
  • /10

    $299,000

    $50K PRICE DROP
    • Land
    • 60 Acres
    • $4,983 per Acre

    911 Waterman Rd, Royalton, VT 05068

    Explore the opportunity of this 60 Acre parcel which is beautifully wooded with awesome mountain view potential. Extensive walking trails throughout the land. Possible development options here or build your private dream retreat. VAST Snowmobile Trails run through the property and the backside of the land abuts the Second Branch of the White River. The land has never been percd for septic. Come

    Marni Rieger KW Vermont-Killington

    911 Waterman Rd, Royalton, VT 05068
  • /21

    $249,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    251 Quarry Rd, Perkinsville, VT 05151

    Open House Sunday 9/20 11-1 This beautifully restored four-season cottage-home in Perkinsville, a historic village within Weathersfield, Vermont is just minutes from the Black River and approximately two miles from the Downers Covered Bridge, this charming retreat offers an inviting connection to the landscape, history, and simple pleasures of Vermont. Lovingly renovated in 2020, the

    Sandy Reavill

    251 Quarry Rd, Perkinsville, VT 05151
  • /14

    $390,000

    • 3 Beds
    • 2 Baths
    • 1,214 Sq Ft

    54 Commonwealth Ave, Springfield, VT 05156

    This well maintained, charming ranch is located on a quiet dead-end street. No thru traffic means peaceful family gatherings on the back deck or private back yard. House features 3 bedrooms, 2 bathrooms and finished basement for children's escape.

    Robert Alger Alger Real Estate Agency

    54 Commonwealth Ave, Springfield, VT 05156
  • /52

    $799,000

    • 6 Beds
    • 3.5 Baths
    • 2,737 Sq Ft

    21 Tapper St, Ludlow, VT 05149

    Welcome to Chapman House - a truly unique historic home with room for many friends and family.This property has been very fortunate to have owners who have consistently cared for and improved this amazing place. The current owners have added safety features including sprinklers and detectors and fire pulls with a system panel. These updates have allowed them to share this Victorian with

    Tyleen Murray Kelley Real Estate, Inc.

    21 Tapper St, Ludlow, VT 05149
  • /42

    $595,000

    $5K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft

    164 Pine View Ln, Cavendish, VT 05142

    Welcome to this charming, easy-care country home nestled on a private road in the heart of Cavendish, Vermont. Offering 4 bedrooms and two bathrooms, this inviting property combines comfortable living with the peaceful beauty of its natural surroundings. A covered front porch welcomes you into the foyer, where you'll immediately appreciate the open-concept floor plan designed for everyday living

    Joseph Karl William Raveis Real Estate Vermont Properties

    164 Pine View Ln, Cavendish, VT 05142
  • /21

    $299,000

    • Land
    • 54 Acres
    • $5,537 per Acre

    00 Skyview Ln, Bethel, VT 05032

    A rare opportunity to own 54 acres offering privacy, views, and flexibility! This offering consists of two adjoining, separately surveyed and subdivided 27-acre parcels, being sold together as one package. The property features an established road Skyview Lane, power and fiber-optic internet on site, wastewater permits in place, scenic views, and a desirable mix of open land and wooded sections.

    Eric Kenyon Rural Vermont Real Estate

    00 Skyview Ln, Bethel, VT 05032
  • /9

    $119,000

    $10K PRICE DROP
    • Land
    • 7.95 Acres
    • $14,969 per Acre

    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143

    Nestled in the picturesque hills of Chester, this inviting 7.95+/- acre property offers the perfect blend of privacy, beauty, and potential. Wander through a peaceful forest where moss covered stones, classic Vermont stone walls, and soft woodland light create a truly serene setting. With some thoughtful clearing, this parcel could open up to stunning views overlooking the charming fields and

    Thaddeus Abare Barrett and Valley Associates Inc.

    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
  • /20

    $169,000

    • 1 Bed
    • 1 Bath
    • 200 Sq Ft

    3019 Popple Dungeon Rd, Chester, VT 05143

    Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3019 Popple Dungeon Rd, Chester, VT 05143
  • /45

    $595,000

    $100K 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
  • /51

    $775,000

    • 4 Beds
    • 3 Baths
    • 2,967 Sq Ft

    451 Williams Ln Unit 4, Hartford, VT 05001

    A truly rare offering in Quechee Lakes, this four-bedroom residence is one of only three freestanding condominiums in Quechee. Located at the top of the Quechee ski hill, it offers an exceptional ski on/ski off setting with peaceful views overlooking the pond.The home’s open living space is filled with natural light from expansive windows, while soaring ceilings and a striking stone

    Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

    451 Williams Ln Unit 4, Hartford, VT 05001
  • /60

    $1,200,000

    $100K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft

    366 Knapp Pond Rd, Cavendish, VT 05142

    Did I read that right? 172 acres?! Impeccably renovated farmhouse on +-172 acres - what more could you ask for? ~131 acres of this property are located in Cavendish while the other ~41 are in Reading. Enjoy apples straight from the backyard. Listen and watch the brook babble down by the road and enjoy the peace that comes from this lovely home. All new Marvin Elevate windows, all new appliances,

    Franchesca Collins Hall Collins Real Estate Group

    366 Knapp Pond Rd, Cavendish, VT 05142
  • /60

    $795,000

    Open Sat 8:30AM - 11:30AM
    • 3 Beds
    • 2.5 Baths
    • 2,416 Sq Ft

    934 Heald Rd, Proctorsville, VT 05153

    Enjoy the best of Vermont living in this recently built 3-bedroom, 2.5 -bathroom country home in Cavendish. Designed with comfort and functionality in mind, this home welcomes you through a convenient mudroom with storage, perfect for all your year-round gear. Step into the open-concept living area featuring vaulted ceilings, a wood-burning fireplace, and a seamless flow between the kitchen,

    Joseph Karl William Raveis Real Estate Vermont Properties

    934 Heald Rd, Proctorsville, VT 05153
  • /11

    $87,826

    New Construction
    • 1 Bed
    • 1 Bath
    • 643 Sq Ft

    23 Cubb Ct, Windsor, VT 05089

    Welcome to 23 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 1 bedroom, 1 bathroom, and 643 sq. ft. (13'4"x48) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

    Kate Barry EXP Realty

    23 Cubb Ct, Windsor, VT 05089
  • /34

    $619,900

    $105K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,938 Sq Ft

    4205 Vermont 131, Weathersfield, VT 05151

    Step into timeless New England charm with this historic circa-1760s expanded Cape, offering a wonderful blend of early craftsmanship, character, and modern-day livability. The home showcases classic timber frame construction with hand hewn beams, beautiful wide plank floors, and preserved period details that create warmth and authenticity throughout every room. With three bedrooms and two full

    Thaddeus Abare Barrett and Valley Associates Inc.

    4205 Vermont 131, Weathersfield, VT 05151
  • /23

    $125,000

    • Land
    • 10.3 Acres
    • $12,136 per Acre

    167 Leons Ln, Sharon, VT 05068

    Discover a rare development opportunity tucked away in the Vermont woods. Situated on a quiet, dead-end road, this stunning 10+ acre parcel offers the perfect canvas for your dream mountain sanctuary. The land features a serene mix of deciduous and evergreen trees and slopes upward, offering excellent potential for a home with a walk-out basement. While a rustic cabin shell currently sits on the

    Holly Hall Hall Collins Real Estate Group

    167 Leons Ln, Sharon, VT 05068
  • /24

    $399,999

    $25K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,239 Sq Ft

    10 W Hill St, Ludlow, VT 05149

    Opportunities like this are rare. Tucked into one of the most desirable locations near Okemo Mountain, this property offers exceptional access to year-round recreation, dining, shopping, and entertainment while avoiding the congestion of the main Access Road. Just under a half mile away, Witalec Road provides a convenient cut-through directly to the Access Road and mountain parking, helping you

    Mendi Michael Engel & Völkers Okemo

    10 W Hill St, Ludlow, VT 05149
  • /34

    $350,000

    • 1 Bed
    • 1 Bath
    • 599 Sq Ft

    318 Mountain Rd Unit A-304, Ludlow, VT 05149

    Okemo Mountain Lodge, come experience unbeatable convenience, ideally located at the base of Okemo Mountain Resort. This one-bedroom residence offers the ease of ownership with true ski-in/ski-out access. Easy access to the main base area, where ski services, lifts, dining, and après-ski options are all right outside your door. The unit comfortably sleeps four, making it perfect for personal

    Katherine Burns William Raveis Real Estate Vermont Properties

    318 Mountain Rd Unit A-304, Ludlow, VT 05149
  • /22

    $249,900

    • 2 Beds
    • 1 Bath
    • 930 Sq Ft

    3537 Popple Dungeon Rd, Chester, VT 05143

    Enjoy the beauty and charm of Vermont with this mobile home set on approximately 1 acre in Chester. Located across the road from a peaceful river, this property offers a wonderful setting for enjoying the outdoors and the natural beauty of the area. The property features an oversized 2 car garage with plenty of room for vehicles, recreational equipment, tools, and hobbies. Above the garage is

    Thaddeus Abare Barrett and Valley Associates Inc.

    3537 Popple Dungeon Rd, Chester, VT 05143
  • /55

    $539,000

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,436 Sq Ft

    879 E Ash Rd Unit 5, Plymouth, VT 05056

    Spanning four thoughtfully designed levels, this home features four bedrooms, 3.5 baths, a separate office, living room, dining room and game room-a combination that's hard to find between Okemo and Killington. This is one of the five larger units at The Ledges with its end unit position adding a full living room that the standard units don't have.In 2023 the original greenhouse wall in the

    McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

    879 E Ash Rd Unit 5, Plymouth, VT 05056
  • /40

    $749,000

    $50K PRICE DROP
    • 7 Beds
    • 9 Baths
    • 7,428 Sq Ft

    52 Upper, Bridgewater, VT 05035

    The ideal property for a SKI CLUB! 7 bedrooms! 6 bathrooms! An immaculate, professionally appointed commercial kitchen! Spacious common rooms and dining areas! A classic and inviting bar/lounge area! An interior with the true Vermont style appeal of exposed beams, wood floors and a stone faced fireplace! This inviting New England style building is perfectly situated midway between world class

    John Wetmore Wetmore Real Estate

    52 Upper, Bridgewater, VT 05035

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