Bennington, VT Homes

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  /15

  $115,000

  • Land
  • 2.90 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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  /35

  $3,500 per month

  • 3 Beds
  • 3 Baths
  • 1,312 Sq Ft
  • House for Rent

  3 Bromley Forest Rd, Winhall, VT 05340

  Adorable 3 bed, 3 bath ranch located on desirable Bromley Forest Road in Winhall, just over the border from Manchester. This fully furnished home offers a perfect blend of comfort and convenience in a peaceful, wooded setting. The main level features an open and inviting layout, including a spacious living room, a fully equipped kitchen, and a cozy dining area. The 1st floor primary bedroom

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 300-3940

  3 Bromley Forest Rd, Winhall, VT 05340
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  /26

  $575,000 Sold Aug 15, 2025

  • 2,448 Sq Ft
  • $235/SF
  • 17 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1981

  2 Spruce High Rd, Winhall, VT 05340

  Nestled in the desirable Vermont Ventures development, this stunning barn-style home blends rustic charm with modern comfort. Featuring soaring cathedral ceilings with exposed beams, the spacious open-concept kitchen, living, and dining areas are bathed in natural light, creating a warm and inviting atmosphere. Step outside to a large private deck with a hot tub—perfect for relaxing or

  Carrie Mathews Winhall Real Estate

  2 Spruce High Rd, Winhall, VT 05340
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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
• 

  

  

  /35

  $359,000

  • 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
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  /40

  $13,000 per month

  • 5 Beds
  • 4.5 Baths
  • 4,100 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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  /53

  $775,000 Sold Aug 13, 2025

  • 1,842 Sq Ft
  • $421/SF
  • 7 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1986

  E12 Rock Ridge Rd, Winhall, VT 05155

  Move right in and start enjoying the Vermont lifestyle at Piper Ridge E12 —an impeccably updated, fully furnished 3-bedroom plus den, 3-bath townhome just minutes from Stratton Mountain. Inside this turnkey home, you'll find bright and welcoming spaces designed for comfort and functionality. Every detail has been thoughtfully considered —a brand-new kitchen, stylishly renovated baths, new

  Cheyanne Pugliese

  E12 Rock Ridge Rd, Winhall, VT 05155
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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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  /37

  $2,400,000

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft

  115 Benson Fuller Dr, Jamaica, VT 05343

  Perched on 3.5 private acres with commanding views from Stratton’s iconic slopes to Bromley’s trails, this architecturally striking residence blends the serenity of the mountains with sophisticated modern design. A dramatic central staircase anchors the home, leading to a sleek custom kitchen and a vaulted great room where walls of glass frame panoramic vistas. A floor-to-ceiling stone fireplace

  Carrie Mathews Winhall Real Estate

  115 Benson Fuller Dr, Jamaica, VT 05343
• 

  

  /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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  /41

  $1,150,000 Sold Jul 25, 2025

  • 2,593 Sq Ft
  • $444/SF
  • 369 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1997

  35 Old Ridge Rd, Winhall, VT 05155

  Located in Stratton High Meadow, this four-bedroom six-bathroom home has everything you need and has a winter shuttle up to Stratton base area for skiing and snowboarding. Walking into the home, there is a large mudroom with bench and plenty of room to get gear organized and ready for the day on the mountain. The two-bay garage is off the right. Continuing, the living and dining areas have

  Mike England Michael England Real Estate

  35 Old Ridge Rd, Winhall, VT 05155
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  /38

  Est $762,685 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,081 Sq Ft

  80 Pond View Rd, Winhall, VT 05340

  80 Pond View Rd, Winhall, VT 05340
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  /60

  $1,825,000 Open House 8/30

  • 3 Beds
  • 4 Baths
  • 2,872 Sq Ft

  36 Beaver St, Bondville, VT 05340

  Your Ultimate Vermont Mountain Retreat Awaits! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape—crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a 10-minute

  MaryKate Grey Stratton Real Estate

  36 Beaver St, Bondville, VT 05340
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  /35

  $9,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,908 Sq Ft
  • House for Rent

  43 Cranberry Hill Rd, Winhall, VT 05340

  First time available for a seasonal rental.Call 43 Strattonwald home for your 25-26 ski season. This recently updated modern, yet classic chalet has room for all. With four bedrooms, two of the primary bedrooms with en-suite bathrooms, there is ample room for everyone's comfort. The home has brand new bathrooms, modern decor and state of the art appliances. With several living areas

  Peggy O'neill Cummings & Co

  43 Cranberry Hill Rd, Winhall, VT 05340
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  /28

  $770,000 Sold Jul 18, 2025

  • 3,556 Sq Ft
  • $217/SF
  • 113 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1980

  5 Stratton Ridge Rd, Winhall, VT 05340

  Discover the ultimate Vermont ski retreat, just 2 miles from Stratton Mountain. This captivating home offers breathtaking mountain views across three spacious levels. The upper level features a private primary suite with a newly renovated bath and a cozy loft/office space — your peaceful sanctuary. The heart of the home, the main level, is perfect for gathering, with soaring cathedral ceilings,

  Carrie Mathews Winhall Real Estate

  5 Stratton Ridge Rd, Winhall, VT 05340
• 

  

  /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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  /55

  $2,225,000

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

  16 Hunter Ridge Rd, Bondville, VT 05340

  Custom built Wadsworth Design Build timber-frame mountain retreat blends luxury, craftsmanship, and convenience just minutes from Stratton Mountain Resort. Set on 2.66 acres and spanning 5,000± square feet, this 4-bedroom, 5-bath home includes two additional sleeping space ideal for hosting friends and family. A grand entry framed by oversized Douglas fir posts welcomes you into a lodge style

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  16 Hunter Ridge Rd, Bondville, VT 05340
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  /48

  $7,000 per month

  • 5 Beds
  • 3.5 Baths
  • 3,858 Sq Ft
  • House for Rent

  20 Jamie Ln, Winhall, VT 05340

  Escape to the tranquility of Vermont with this stunning long-term rental at "Valley View." Nestled in a desirable neighborhood of Winhall, this spacious contemporary home offers unparalleled panoramic views of the surrounding mountains. Imagine waking up to the beauty of the Green Mountains every day in this expansive retreat!This meticulously maintained 5-bedroom, 3.5 bathroom home

  David Powers 42 North LP

  20 Jamie Ln, Winhall, VT 05340
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  /22

  $265,500 Sold Jul 15, 2025

  • 1,332 Sq Ft
  • $199/SF
  • 72 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  18 Stratton Ridge Rd, Winhall, VT 05340

  Welcome to 18 Stratton West Road – a charming 3-bedroom, 2-bath ski condo located just minutes from Stratton Mountain Resort. This spacious unit features over 1,300 square feet of well-maintained living space, complete with a cozy wood-burning fireplace, updated bathrooms, and generous natural light throughout. The open-concept layout is perfect for entertaining, with a functional kitchen, dining

  Derek Greene Derek Greene

  18 Stratton Ridge Rd, Winhall, VT 05340
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  /35

  Est $623,746 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
• 

  

  /44

  $2,500,000

  • 5 Beds
  • 7 Baths
  • 6,625 Sq Ft

  19 Old Town Rd, Bondville, VT 05340

  Experience Vermont luxury at 19 Old Town Road, Winhall—a stunning 5-bedroom, 7-bathroom estate on 21.53 private acres. Built in 2000, this meticulously designed retreat offers unobstructed views of both Stratton Mountain and Magic Mountain.The spacious great room is the heart of the home, featuring soaring ceilings, a grand stone fireplace, and walls of windows that frame breathtaking

  Christiane Carroccio TPW Real Estate

  19 Old Town Rd, Bondville, VT 05340
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  /46

  $5,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  15 Nearing Rd, Winhall, VT 05340

  Imagine waking up to inspiring vistas every day in this remarkable 3 bedroom, 3.5 bath saltbox home. Perched to capture stunning panoramic views of Stratton Mountain's trails, this classic contemporary ski home offers a truly special living experience. The property is settled upon a 1.63-acre knoll and abuts the Winhall Forest, offering peace and privacy.Embrace sustainable living with a

  David Powers 42 North LP

  15 Nearing Rd, Winhall, VT 05340
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  /54

  $970,000 Sold Jun 17, 2025

  • 2,672 Sq Ft
  • $363/SF
  • 120 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1994

  13 Windtree Rd, Bondville, VT 05340

  OPEN HOUSE SATURDAY , February 22nd-11:00-3:00.Showings begin 2/20Exceptional Stratton Mountain Resort location on Windtree Road in the desirable North Brookwood neighborhood with Shuttle from your driveway to the Base Lodge! Enjoy this wonderful deck house open floor plan with great winter views, vaulted ceilings, 2 wood burning fireplaces and multiple decks. Well designed for apres ski

  Kim Morgan-Wohler Wohler Realty Group

  13 Windtree Rd, Bondville, VT 05340
• 

  

  /40

  Not Listed For Sale

  • 9 Beds
  • 8 Baths
  • 3,375 Sq Ft

  103 Winhall Hollow Rd, Bondville, VT 05340

  103 Winhall Hollow Rd, Bondville, VT 05340
• 

  

  /50

  $1,050,000

  • 5 Beds
  • 5.5 Baths
  • 4,729 Sq Ft

  83 Benson Fuller Dr, Bondville, VT 05340

  Just an 8-minute drive to Stratton, 83 Benson Fuller Drive sits atop the beautiful Forest Farms neighborhood, offering both serenity and convenience. This meticulously updated home is ready for you to move in and enjoy the best of Vermont living. Nestled on a quiet dirt road, it’s perfect for morning and evening strolls with the dog before or after a day on the slopes.Inside, this

  Christiane Carroccio TPW Real Estate

  83 Benson Fuller Dr, Bondville, VT 05340
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  /32

  $14,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • House for Rent

  14 Burnt Hill Rd, Winhall, VT 05340

  This modern Strattonwald gem is the ultimate plug-and-play Vermont summer house with location, style, convenience and a lake-side lifestyle to remember. Three living spaces -- one on each floor -- allow for plenty of overflow in the morning and afternoon, with two fireplaces ready for friends and family. Four bedrooms plus sleep loft with its own hang-out space lend space for the whole crew!

  Jamie Luke TPW Real Estate

  14 Burnt Hill Rd, Winhall, VT 05340
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  /29

  $363,825 Sold Jun 06, 2025

  • 1,215 Sq Ft
  • $299/SF
  • 19 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1968

  30 Birch Hill Rd Unit 8 Rock Maple, Winhall, VT 05340

  Discover the ease of Mountain living with the complimentary Birch Hill Shuttle, providing seamless access to winter adventures. This bright and welcoming end-unit townhouse offers plenty of space for family and friends to gather and unwind. With two inviting living areas, three comfortable bedrooms, and two well-appointed bathrooms, there's room for everyone to relax. The spacious entryway is

  Christine Chovan

  30 Birch Hill Rd Unit 8 Rock Maple, Winhall, VT 05340
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  /40

  Est $815,323 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
• 

  

  /40

  $1,450,000

  • 5 Beds
  • 3.5 Baths
  • 4,017 Sq Ft

  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 lot justdown 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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  /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
• 

  

  /39

  $405,000 Sold May 16, 2025

  • 1,215 Sq Ft
  • $333/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1968

  5 Red Hickory Rd, Winhall, VT 05340

  The season is not over! Red Hickory 5 at Birch Hill is one of the best values today offered at Stratton. This ready to move into attractively appointed Co-Op townhome is located at the quiet end of popular Birch Hill street with views of the mountain. Three bedrooms, two baths, family room. Winter shuttle service to the base lodge. Brand new in ground pool for your summer enjoyment. This

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  5 Red Hickory Rd, Winhall, VT 05340
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  /25

  Est $770,949 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,550 Sq Ft

  110 Upper Taylor Hill Rd, Jamaica, VT 05343

  110 Upper Taylor Hill Rd, Jamaica, VT 05343
• 

  

  /46

  $1,350,000

  • 4 Beds
  • 4 Baths
  • 4,640 Sq Ft

  33 Forest Haunts Rd, Winhall, VT 05340

  Discover Your Vermont Retreat Nestled amidst 20.8 private acres of tranquil woods, this French country manor offers an exceptional opportunity to own a piece of Vermont paradise. Situated near the serene North Branch Ball Mountain Brook, enjoy the soothing sounds of cascading water and the breathtaking beauty of nature. Property Highlights: Prime Location: Just minutes from Stratton Resort for

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  33 Forest Haunts Rd, Winhall, VT 05340
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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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  /29

  $750,000 Sold May 12, 2025

  • 3,084 Sq Ft
  • $243/SF
  • 82 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2003

  12 Jamie Ln, Jamaica, VT 05343

  Showings begin Saturday, February 22, 2025. Set in the heart of Vermont’s stunning landscape, this handcrafted Lincoln Log home offers the perfect blend of privacy and convenience. Surrounded by towering Maples and classic stone walls, it’s just minutes from Stratton’s ski slopes and a short drive to Bromley, Magic Mountain, and Manchester. Inside, a bright, open floor plan features soaring

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  12 Jamie Ln, Jamaica, VT 05343
• 

  

  /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
• 

  

  /59

  $1,200,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 4,054 Sq Ft

  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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  /30

  $330,000 Sold May 09, 2025

  • 1,088 Sq Ft
  • $303/SF
  • 115 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1970

  21 Stratton Ridge Rd, Winhall, VT 05340

  This charming 3-bedroom, 1.5-bathroom condo is the perfect getaway for ski enthusiasts and nature lovers alike. Conveniently located just minutes from Stratton Mountain, you'll enjoy year-round access to skiing, hiking, and all the village has to offer.Entry has a built-in storage area for all of your gear. The updated kitchen with radiant heat tile floors, features modern appliances, granite

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  21 Stratton Ridge 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

  $789,000

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

  44 Hilltop Rd, Winhall, VT 05340

  Four bedroom, four bathroom Intervale townhouse has all the space you need in a Stratton home. This is the largest Intervale floor plan, with a second living room and wet bar on the lower, walk out floor. The main floor has a mud room entry, living room with wood burning fireplace, and dining room open to kitchen. The primary suite is on the main floor, secondary suite is upstairs, and an

  Christiane Carroccio TPW Real Estate

  44 Hilltop Rd, Winhall, VT 05340

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