Winhall, VT Homes

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  /15

  $115,000

  • Land
  • 2.9 Acres
  • $39,655 per Acre

  Lot 3 Route 11 30, Winhall, VT 05340

  Spectacular West and Southerly Views over Manchester Valley and boasts a bird's eye view across to the Equinox Mountain!Located on the Manchester side of Winhall, this property is at the end of a private lane offering privacy... engineered and offering VT Waste Water and Potable Water Supply Permit: WW-2-3614, design for 3 BR single family residence. Bordered by the Green Mountain Nat'l

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 808-6197

  Lot 3 Route 11 30, Winhall, VT 05340
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  /40

  $13,000 per month

  • 5 Beds
  • 4.5 Baths
  • 5,080 Sq Ft
  • House for Rent

  21 Valley View Rd, Winhall, VT 05255

  Spectacular 5 bedroom, 5 bathroom house with panoramic mountain views!!! Entry level offers a 2 car garage, laundry room, powder room and large eat in kitchen. Beautiful views out the back sun room! Kitchen opens up to cathedral ceilings in the great room with center stone fireplace, formal dining room, foyer and den. Expansive primary suite on the first floor over looking the back deck with hot

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 328-9426

  21 Valley View Rd, Winhall, VT 05255
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  /24

  $1,025,000 Sold Oct 10, 2025

  • 2,160 Sq Ft
  • $475/SF
  • 5 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1988

  10 Middle Ridge Rd, Winhall, VT 05155

  Fox Chapel luxury townhome at Stratton. This four bedroom, four bathroom home is offered with the ability to skip the wait list at the Stratton Mountain Club. Renovated bathrooms and air conditioning make this the year round place to be. Prime location next to the ‘Chapel of the Snows’ and the Commons, walk to the Stratton village for ski access, dining, shopping, and resort amenities. Watch the

  Christiane Carroccio TPW Real Estate

  10 Middle Ridge Rd, Winhall, VT 05155
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  /31

  Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,888 Sq Ft

  12 Stratton Rd W Unit 12, Winhall, VT 05340

  12 Stratton Rd W Unit 12, Winhall, VT 05340
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  /35

  $359,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  33 Aspen Ln, Bondville, VT 05340

  Minutes from Stratton Mountain, this cozy chalet offers the perfect mountain escape with timeless character and room to make it your own. Featuring a classic chalet style floor to ceiling stone fireplace and wood interior, this home exudes vintage alpine charm. There are three bedrooms, two baths and an open concept living space, providing plenty of room for gatherings or weekend getaways.

  

  Alison Cummings

  Cummings & Co

  (802) 424-9210

  33 Aspen Ln, Bondville, VT 05340
• 

  

  /19

  $37,000 per month

  • 3 Beds
  • 3 Baths
  • 2,920 Sq Ft
  • House for Rent

  2 Aspen Ln, Winhall, VT 05340

  Stratton views, sunlight, space, and location: this chalet-style log cabin has it all! The open floor plan of the main level brings everyone together around the spacious kitchen, dining area, and living room, under a vaulted cathedral ceiling and with a wall of windows overlooking the forest below and Stratton's peak ahead. Front deck offers dining area and a grill for the most outdoorsy of

  Jamie Luke TPW Real Estate

  2 Aspen Ln, Winhall, VT 05340
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  /27

  $440,000 Sold Oct 03, 2025

  • 1,400 Sq Ft
  • $314/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  6 Moose Maple Rd, Winhall, VT 05340

  Located in the desirable Moose Maple section of Birch Hill, this well-maintained 3-bedroom, 2-bath Co-Op offers some of the best direct views of Stratton Mountain, along with the convenience of a community shuttle and close proximity to the newly rebuilt seasonal pool. Freshly painted and thoughtfully updated, the condo features flexible living spaces including a lower-level bedroom with a custom

  Andy Reed Four Seasons Sotheby's Int'l Realty

  6 Moose Maple Rd, Winhall, VT 05340
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  /28

  Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 5,896 Sq Ft

  27 Mountain View Rd, Winhall, VT 05360

  27 Mountain View Rd, Winhall, VT 05360
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  /42

  $1,100,000

  • 5 Beds
  • 4.5 Baths
  • 4,453 Sq Ft

  6 Old Ridge Rd, Winhall, VT 05340

  Welcome to High Meadow, one of Stratton’s most desirable neighborhoods. This expansive residence at 6 Old Ridge Road offers over 4,600 sq. ft. across three finished levels, combining mountain convenience with comfort, privacy, and style. The main level features an open kitchen, dining and vaulted living room with fireplace, plus a sunroom, screened porch, stone patio, and a private primary suite.

  

  Trent Stephens

  Wohler Realty Group

  (802) 213-9409

  6 Old Ridge Rd, Winhall, VT 05340
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  /44

  $80,000 per month

  • 5 Beds
  • 3.5 Baths
  • 4,017 Sq Ft
  • House for Rent

  11 Founders Hill Rd, Winhall, VT 05360

  Stratton Mountain location for full time or vacation style living! Spacious home that you can walk to Village, gondola, golf and Sports center. Corner lotjust down the street from the Stratton Mountain Club and the Base Lodge. Home has five bedrooms with a chefs kitchen that has Viking Stove, ice-maker and three dishwashers for entertaining guests. Living room and dining room are graced with

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  11 Founders Hill Rd, Winhall, VT 05360
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  /32

  $560,000 Sold Sep 26, 2025

  • 1,400 Sq Ft
  • $400/SF
  • 13 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  35 Glendon Hills Rd, Bondville, VT 05340

  Discover your dream home in Glendon Hills! A truly rare opportunity, this property is the first to become available in this coveted neighborhood in over a decade. Imagine owning a private 1-acre sanctuary with your own picturesque, thriving pond. Inside, experience the joy of cooking in a well-appointed chef's kitchen and the comfort of an open-concept design centered around a charming stacked

  Robin Apps Four Seasons Sotheby's Int'l Realty

  35 Glendon Hills Rd, Bondville, VT 05340
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  /31

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,215 Sq Ft

  6 Black Birch Rd, Winhall, VT 05340

  6 Black Birch Rd, Winhall, VT 05340
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  /45

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 4,200 Sq Ft

  9 Lower Taylor Hill Rd, Winhall, VT 05340

  Come home to your own Vermont playground! Situated on 8.75 private acres at the base of Stratton Mountain Resort access road, this recently renovated single family residence has all the amenities that your family needs. Explore the grounds, play in the Winhall river, hike the surrounding trails, and enjoy the mountain views. Property has easy access to the VAST snowmobile trails directly from the

  Timothy Mich Doddridge Stratton Real Estate

  9 Lower Taylor Hill Rd, Winhall, VT 05340
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  /12

  $4,600 per month

  • 3 Beds
  • 1.5 Baths
  • 1,948 Sq Ft
  • House for Rent

  10 Rocky Rd, Winhall, VT 05340

  Location, location location..... This three-bedroom gem is located in one of the most desirable areas in the tri-mountain area. Centrally located between Stratton and Manchester; you will find yourself less than a 15-minute drive to each. Bromley is around the corner. The perfect chalet to come home to after a fun day of skiing. Sit by the roaring fire with a cup of cocoa and

  Peggy O'neill Cummings & Co

  10 Rocky Rd, Winhall, VT 05340
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  /39

  $2,250,000 Sold Sep 25, 2025

  • 6,471 Sq Ft
  • $348/SF
  • 88 Days On Market

  • 8 Beds
  • 8.5 Baths
  • Built 2009

  69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155

  This extraordinary Stratton Mountain Retreat, just minutes to the slopes, offers glorious long range views and a very private setting. This impressive home was masterfully constructed in 2009 and includes a separate barn, 11.55 acres of land, 2 covered porches, a built in barbecue and an outdoor fireplace, hot tub and fire pit.The main level of the home features a Gourmet Kitchen, grand

  Sara Buckley Josiah Allen Real Estate, Inc.

  69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155
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  /35

  Est $613,598 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,577 Sq Ft

  10 Pond View Rd, Winhall, VT 05340

  10 Pond View Rd, Winhall, VT 05340
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  /45

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 2,028 Sq Ft

  7 N Brookwood Rd, Winhall, VT 05340

  OPEN HOUSE SUNDAY OCTOBER 12TH 11:00AM-1:00PM!Escape to the mountains in this enchanting 4 bedroom, 3.5 bath home just moments from Stratton Resort in one of the areas most sought after neighborhoods! Offering classic chalet charm and convenience, this well-appointed home includes winter weekend/holiday shuttle service to the Stratton. After a day on the mountain, enjoy a walk to Stratton

  Lauren Behm Berkshire Hathaway HomeServices Stratton Home

  7 N Brookwood Rd, Winhall, VT 05340
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  /20

  $5,800 per month

  • 3 Beds
  • 2 Baths
  • 2,348 Sq Ft
  • House for Rent

  8 Rocky Rd, Winhall, VT 05340

  Located in one of the most sought-after spots in the area. This three-bedroom "mid-century vibed" beauty is just a 10-minute drive to the Stratton Access Road and a 12-minute drive to Manchester. Bromley is literally around the corner and Magic is a quick 15-minute drive.There is a beautiful stream in the backyard that adds additional "802" ambiance to the property. Truly a peaceful setting

  Peggy O'neill Cummings & Co

  8 Rocky Rd, Winhall, VT 05340
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  /3

  $26,000 Sold Sep 19, 2025

  • Land
  • 1.1 Acres
  • $23,636 per Acre

  • 656 Days On Market

  0 Deepwoods Rd Unit 4976604, Winhall, VT 05340

  Discover the perfect spot for your next adventure with this prime piece of land in Winhall. Imagine placing a charming tiny home on this property and owning your own slice of Vermont paradise. The land comes with preliminary septic design information, making it easier for you to start your new chapter. Enjoy the best of all worlds: live amidst the breathtaking mountains in a cozy, manageable

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  0 Deepwoods Rd Unit 4976604, Winhall, VT 05340
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  /40

  Est $755,679 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 4,000 Sq Ft

  386 Winhall Hollow Rd, Bondville, VT 05340

  386 Winhall Hollow Rd, Bondville, VT 05340
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  /43

  $1,100,000

  • 5 Beds
  • 4 Baths
  • 4,788 Sq Ft

  6 Chad Cir, Winhall, VT 05340

  Tucked away at the end of a private cul-de-sac and just minutes from Stratton's slopes, this beautifully designed mountain home offers the perfect blend of comfort and luxury. The open-concept floor plan features a chef’s kitchen with granite countertops, a 6-burner professional gas stove, double ovens, a farm sink, and a wet bar with ice maker—ideal for entertaining. Wide pine floors and a

  Carrie Mathews Winhall Real Estate

  6 Chad Cir, Winhall, VT 05340
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  /14

  $27,000 per month

  • 3 Beds
  • 2 Baths
  • 2,486 Sq Ft
  • House for Rent

  36 Glendon Hills Rd, Bondville, VT 05340

  Seasonal Rental Near Stratton Mountain – $27,000Enjoy the ultimate Vermont winter escape with this charming 3-bedroom, 2-bath seasonal rental located just minutes from Stratton Mountain Resort and only 15 minutes to Manchester. Whether you're a skier, snowboarder, or simply love cozy mountain living, this home checks all the boxes.

  Christina Dryden Berkshire Hathaway HomeServices Stratton Home

  36 Glendon Hills Rd, Bondville, VT 05340
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  /22

  $445,000 Sold Sep 16, 2025

  • 1,590 Sq Ft
  • $280/SF
  • 13 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  163 Vt Route 30, Winhall, VT 05340

  Charming Restored Post & Beam Home with Commercial Zoning Near Stratton. Discover the perfect blend of rustic charm and modern functionality in this beautifully restored post and beam home ideally situated at the corner of Vermont Route 30 and scenic Kendall Farm Road. Featuring three bedrooms and two full baths, the home offers soaring vaulted ceilings, exposed beams, and an abundance of natural

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  163 Vt Route 30, Winhall, VT 05340
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  /25

  Est $742,403 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,600 Sq Ft

  110 Upper Taylor Hill Rd, Jamaica, VT 05343

  110 Upper Taylor Hill Rd, Jamaica, VT 05343
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  /58

  $975,000

  • 5 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  20 Jamie Ln, Winhall, VT 05340

  Get ready for ski season! Plenty of space for the whole family. Set up for fun with two living rooms, a hot tub and barrel sauna. Great rental history. Owner is Listing Broker.

  David Powers 42 North LP

  20 Jamie Ln, Winhall, VT 05340
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  /23

  $42,000 per month

  • 4 Beds
  • 3 Baths
  • 2,406 Sq Ft
  • House for Rent

  35 Strattonwald Rd, Winhall, VT 05340

  $42,000 Winter Rental Rate | Spend the winter in Vermont at this inviting 4-bedroom, 3-bath Strattonwald chalet, available mid-November through mid-April. Nestled among the woods yet just minutes from Stratton Mountain, this home offers a welcoming retreat and the perfect base for the ski season. The main living area features soaring vaulted ceilings and a pellet stove, creating a bright and cozy

  Cheyanne Pugliese

  35 Strattonwald Rd, Winhall, VT 05340
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  /47

  $822,500 Sold Sep 12, 2025

  • 2,598 Sq Ft
  • $317/SF
  • 18 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1983

  C1 Meadow Ridge Rd, Winhall, VT 05340

  WELCOME TO YOUR FAMILY'S PERFECT MOUNTAIN RETREAT..WELCOME TO PIPER RIDGE!! This spacious 4 bedroom/4 bath condo is designed for comfort, convenience and offers an exceptional blend of mountain charm and modern amenities! Enjoy two open concept living areas with cozy wood burning fireplaces, fully equipped kitchen, private balcony showcasing winter mountain views...Perfect for entertaining...With

  Sunny Breen Josiah Allen Real Estate, Inc.

  C1 Meadow Ridge Rd, Winhall, VT 05340
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  /35

  Est $397,000 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  15 Stratton View Rd, Bondville, VT 05340

  15 Stratton View Rd, Bondville, VT 05340
• 

  

  /37

  $999,000

  • 4 Beds
  • 3.5 Baths
  • 2,280 Sq Ft

  17 Roundtree Rd, Winhall, VT 05340

  Contemporary ski chalet on shuttle route located on a short cul-de-sac in the coveted North Brookwood neighborhood, a stone's throw from the Stratton base lodge. This 4 bedroom, 3 1⁄2 bath home boasts an open plan, walls of windows, and floor-to-ceiling stone fireplace in the Great Room. The pass-through kitchen was fully renovated in 2021 in addition to many other upgrades. Test your skills at

  Sarah Nichols Winhall Real Estate

  17 Roundtree Rd, Winhall, VT 05340
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  /17

  $27,500 per month

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • Condo for Rent

  5 Byington Ln, Winhall, VT 05340

  A classic Austrian chalet, this outdoors enthusiasts' home is structured for year-round fun! The living and entertaining space encompasses the main floor: The functional open kitchen/dining room is perfect for the gang before and after weekend adventures, with a spacious great room and stone fireplace. A cozy, irresistible loft awaits upstairs for moments curled up with a book, coffee and a thick

  Jamie Luke TPW Real Estate

  5 Byington Ln, Winhall, VT 05340
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  /10

  $385,000 Sold Sep 10, 2025

  • Land
  • 24.54 Acres
  • $15,689 per Acre

  • 28 Days On Market

  0 River Rd, Winhall, VT 05340

  24+ Acres in Winhall, VT — Private 1+ Acre Pond, River Frontage & Minutes from Stratton | Welcome to a rare opportunity in the heart of Vermont’s Green Mountains — a stunning 24+ acre parcel in Winhall offering a unique combination of convenience, privacy, natural beauty, and year-round adventure, just minutes from Stratton Resort. With a state-issued wastewater permit in place, the land is

  Cheyanne Pugliese

  0 River Rd, Winhall, VT 05340
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  /13

  Not Listed For Sale

  234 Mountain Rd, Stratton, VT 05155

  234 Mountain Rd, Stratton, VT 05155
• 

  

  /38

  $860,000

  • 4 Beds
  • 3.5 Baths
  • 4,104 Sq Ft

  25 Benson Fuller Dr, Jamaica, VT 05343

  Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape.Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for

  Robin Apps Four Seasons Sotheby's Int'l Realty

  25 Benson Fuller Dr, Jamaica, VT 05343
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  /29

  $30,000 per month

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft
  • Townhouse for Rent

  90 Turkey Run Rd, Winhall, VT 05340

  Intervale Rental. Available for the winter 25-26 winter season. Also available for summer or fall monthly rental. Entry mud room for boot storage. Main floor has wood burning fire place, and the deck off the living room is a overlooks the pond. Main floor has primary suite. Two bedrooms plus a sleeping loft on the upper floor. One bedroom has an en suite bathroom, and a hallway full bathroom

  Christiane Carroccio TPW Real Estate

  90 Turkey Run Rd, Winhall, VT 05340
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  /59

  $1,082,500 Sold Aug 29, 2025

  • 4,054 Sq Ft
  • $267/SF
  • 45 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2005

  4 Garden Loop Rd, Winhall, VT 05340

  Your Stratton Mountain retreat awaits! This beautiful turnkey mountain home just off the Stratton Mountain Road is the perfect location for family gatherings, ski trips, hiking and more. This three-bedroom, three-bath home on three levels includes a breathtaking great room with a stone fireplace and vaulted ceilings. Dining room and additional breakfast area next to the kitchen. A large open

  Lucy Ferrada Heney Realtors - Element Real Estate (Montpelier)

  4 Garden Loop Rd, Winhall, VT 05340
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  /27

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,268 Sq Ft

  22 Snowflake Ln, Winhall, VT 05340

  22 Snowflake Ln, Winhall, VT 05340
• 

  

  /31

  $949,000

  • 4 Beds
  • 4.5 Baths
  • 2,658 Sq Ft

  73 Cranberry Hill Rd, Winhall, VT 05340

  Nestled at the end of a quiet road in the highly sought-after Strattonwald community, 73 Cranberry Hill Road is the quintessential European-style ski house, offering the perfect Vermont retreat. This impeccably upgraded home has never been rented and is turn-key, ready for immediate enjoyment. It combines timeless charm with modern conveniences, featuring air conditioning for year-round comfort.

  Carrie Mathews Winhall Real Estate

  73 Cranberry Hill Rd, Winhall, VT 05340
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  /35

  $6,750 per month

  • 4 Beds
  • 3 Baths
  • 2,002 Sq Ft
  • House for Rent

  45 Benson Fuller Dr, Bondville, VT 05340

  David Powers 42 North LP

  45 Benson Fuller Dr, Bondville, VT 05340
• 

  

  /51

  $1,300,000 Sold Aug 25, 2025

  • 4,541 Sq Ft
  • $286/SF
  • 7 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2004

  33 Jamie Ln, Bondville, VT 05340

  Exceptional Log Home tucked away in the beautiful Green Mountains of Vermont. Welcome to 33 Jamie Lane a 12 acre sanctuary minutes to Stratton Mountain Resort. This extraordinary property offers true privacy surrounded by woods and nature. Features three finished levels of dramatic living space with floor to ceiling windows , soaring stone fireplace, and cherry floors. Open concept kitchen/dining

  Cynthia Mitrani Berkshire Hathaway HomeServices Stratton Home

  33 Jamie Ln, Bondville, VT 05340
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  /32

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  43 Middle Ridge Rd Unit 120, Winhall, VT 05155

  43 Middle Ridge Rd Unit 120, Winhall, VT 05155

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