South Londonderry, VT Homes for Sale with Acreage

• 

  

  

  /55

  $495,000

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft

  935 Old Manchester Rd, Peru, VT 05152

  Cozy Off-Grid Cabin on 10 Private Acres – Peace, Privacy & Ski AccessEscape to your own woodland retreat with this charming 2-bed, 1-bath cabin nestled on 10 serene acres of open meadow and forest. Just 4.5 miles to Bromley Ski & Snowboarding Mountain, this property offers the perfect mix of off-grid living and outdoor adventure.Fully self-sufficient with solar power and propane generator

  

  Margretta Fischer

  Wohler Realty Group

  (802) 481-3493

  935 Old Manchester Rd, Peru, VT 05152
• 

  

  

  /20

  $2,425,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 4,536 Sq Ft

  6 Stone Lodge Rd, Winhall, VT 05340

  SHOWINGS BEGIN at Thursday February 12. Premier New Construction, offering 4500+ SF of luxury living on three levels, perched on 2.5 acres to maximize panoramic mountain and Bromley views. Just minutes to the Stratton Resort Base Lodge, this exceptional 4 bedroom/3.5 bath floor plan combines contemporary design, craftsmanship of the highest caliber and energy efficiency.Thoughtfully designed for

  Kim Morgan-Wohler Wohler Realty Group

  6 Stone Lodge Rd, Winhall, VT 05340
• 

  

  

  /60

  $849,000

  • 5 Beds
  • 4.5 Baths
  • 3,840 Sq Ft

  42 Blackberry Ln, Jamaica, VT 05343

  “Sweet Berry Farm” offers a compelling blend of Vermont character and functional living space, set on 5.7 acres in Jamaica just 12 minutes from Stratton. Originally built in the 1850s and expanded over time, the home delivers a flexible layout suited for both full-time use and weekend living.The main level features an open living and dining area with large windows, complemented by a generous

  MaryKate Grey Stratton Real Estate

  42 Blackberry Ln, Jamaica, VT 05343
• 

  

  

  /33

  $1,399,999

  • 6 Beds
  • 4 Baths
  • 3,800 Sq Ft

  121 High Meadow Rd, Winhall, VT 05340

  Bring the whole household to this great place with lots of room for fun. A 6-bedroom, 4-bathroom Adirondack-style Ski Chalet located in a neighborhood just minutes from the Stratton Mountain Ski Resort, with free door-to-mountain shuttle service on select days. Amenities include four (4) fireplaces, best hot-tub on the market, an in home gym, electric sauna, pool table, SuperChexx Bubble Hockey

  Ralph Harvey Listwithfreedom.com

  121 High Meadow Rd, Winhall, VT 05340
• 

  

  

  /50

  $1,800,000

  • 4 Beds
  • 5 Baths
  • 4,853 Sq Ft

  95 Middletown Rd, South Londonderry, VT 05155

  One-of-a-Kind Vermont Lifestyle PropertyHome, Income & Creative Opportunity Welcome to an exceptional Southern Vermont offering that blends refined country living with rare income and lifestyle flexibility. Set on 2.4 picturesque acres in South Londonderry, this beautifully restored 1865 property is first and foremost a warm and inviting 4-bedroom home—rich in character, thoughtfully updated,

  Eric Nathan Nathan Auction & Real Estate Inc.

  95 Middletown Rd, South Londonderry, VT 05155
• 

  

  /47

  $1,140,000

  • 4 Beds
  • 3 Baths
  • 4,193 Sq Ft

  70 Hunter Ln, Jamaica, VT 05343

  Discover a truly special Vermont hidden treasure at 70 Hunter Lane, set within the private Highland Forest community in the Cole Pond community . Just five minutes to Stratton Mountain Resort, this exceptional property offers the perfect balance of privacy, convenience, and year-round recreation. This 4,200 square foot home features four bedrooms and three Bathrooms. The generous living spaces

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  70 Hunter Ln, Jamaica, VT 05343
• 

  

  /60

  $1,160,000

  • 5 Beds
  • 4 Baths
  • 3,664 Sq Ft

  82 N Brookwood Rd, Stratton, VT 05360

  Location , Location , Location! Situated on North Brookwood just below the covered brige you'll enjoy easy access to the Wanderer ski trail as well as the resort shuttle that picks you up at your driveway! This iconic resort property features a great room with custom wood barrel cathedral ceilings, a wall of glass, wood burning fireplace and wrap around deck. Designed for the mountain enthusiast,

  Kim Morgan-Wohler Wohler Realty Group

  82 N Brookwood Rd, Stratton, VT 05360
• 

  

  /31

  $1,200,000

  • 1 Bath
  • 950 Sq Ft

  109 Winhall Hollow Rd, Winhall, VT 05340

  Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  109 Winhall Hollow Rd, Winhall, VT 05340
• 

  

  /39

  $1,750,000

  • 7 Beds
  • 5 Baths
  • 4,649 Sq Ft

  4669 Vermont Route 100, Londonderry, VT 05148

  Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with

  Story Jenks LandVest, Inc/Woodstock

  4669 Vermont Route 100, Londonderry, VT 05148
• 

  

  /28

  $729,000

  • 4 Beds
  • 2 Baths
  • 2,055 Sq Ft

  21 Burnt Hill Rd, Winhall, VT 05341

  Welcome to Gone Ski Inn, your cozy, all-season mountain retreat in the heart of Vermont! This charming home features four inviting bedrooms and two well-appointed bathrooms, offering plenty of space to unwind after a day of adventure. In the winter, cozy up by the crackling wood-burning fireplace , toasty wood stove or relax in the soothing hot tub under the stars. With ski trails just minutes

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  21 Burnt Hill Rd, Winhall, VT 05341
• 

  

  /59

  $2,800,000

  • 3 Beds
  • 3.5 Baths
  • 3,938 Sq Ft

  23 Valley View Rd, Winhall, VT 05340

  Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

  Kim Morgan-Wohler Wohler Realty Group

  23 Valley View Rd, Winhall, VT 05340
• 

  

  /55

  $2,950,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,762 Sq Ft

  59 Garden Loop Rd, Winhall, VT 05340

  Move into this brand new stunning custom contemporary set on over 3 acres in coveted Stratton ski country. This exceptional modern design offers elevated living with superior craftsmanship and sweeping endless views. Featuring four well appointed ensuites with polished baths boasting radiant heated floors, half bath, family room and dual laundry areas. The well designed kitchen with Italian

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  59 Garden Loop Rd, Winhall, VT 05340
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  /27

  $379,000

  • 4 Beds
  • 3 Baths
  • 1,720 Sq Ft

  292 Tallwood Cir, Londonderry, VT 05148

  Welcome to this charming chalet in the Sherwood Forest neighborhood of Londonderry! Come inside to a bright, open great room featuring living and dining areas, large windows, a cozy wood stove, and a breakfast bar that connects seamlessly to the kitchen. This inviting home is the perfect Vermont getaway for you or your guests. Just off the great room, the classic country kitchen offers an ideal

  The Malley Group KW Vermont

  292 Tallwood Cir, Londonderry, VT 05148
• 

  /2

  $125,000

  • Land
  • 1.45 Acres
  • $86,207 per Acre

  L/O River Rd, Winhall, VT 05340

  This 1.45+/- acre building lot offers a rare combination of privacy, recreation, and convenience. An approved Vermont wastewater permit for a 3-bedroom single-family home is already in place, streamlining the path toward building a year-round residence or mountain getaway. The property is located just one mile from the base of the Stratton Access Road and only twenty minutes from Manchester’s

  Cheyanne Pugliese

  L/O River Rd, Winhall, VT 05340
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  /9

  $185,000

  • Land
  • 8 Acres
  • $23,125 per Acre

  4441 Vermont 30, Jamaica, VT 05343

  Set amidst a peaceful woodland setting, this 8.0± acre parcel offers the perfect balance of seclusion and convenience—tucked away for privacy yet easily accessible year-round.. Currently being subdivided from a larger tract, this parcel presents a rare chance to shape your vision from the ground up.A five-bedroom Wastewater Permit has been approved, and a professional boundary survey is

  Helen Nault

  4441 Vermont 30, Jamaica, VT 05343
• 

  

  /37

  $690,000

  • 5 Beds
  • 3 Baths
  • 2,635 Sq Ft

  341 Under the Mountain Rd, Londonderry, VT 05148

  Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

  Andy Reed Four Seasons Sotheby's Int'l Realty

  341 Under the Mountain Rd, Londonderry, VT 05148
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  /12

  $450,000

  • Land
  • 10.26 Acres
  • $43,860 per Acre

  4.1 Pearl Buck Dr, Winhall, VT 05340

  One of the last significant VIEW lots available on the mountain , with unrivaled 360 degree views, including dead on views of Stratton Mountain trails. The pinnacle of this 10.26 acre lot is deserving of an exceptionally designed and expansive home in this premium location with commanding views.Prime for a legacy property in a most desirable location, just 5 minutes to the Stratton Base Area,

  Kim Morgan-Wohler Wohler Realty Group

  4.1 Pearl Buck Dr, Winhall, VT 05340
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  /38

  $375,000

  • Land
  • 1.23 Acres
  • $304,878 per Acre

  0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340

  Exceptional offering. This premier parcel defines phase II of Ravenwood, an enclave of distinctive and premier mountain residences. This notable site offers extraordinary mountain views, direct access from Winhall Hollow Road and still enjoys all the benefits and amenities of The Ravenwood Neighborhood Association. Combining, privacy, natural beauty and convenience, this well-established

  Kim Morgan-Wohler Wohler Realty Group

  0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
• 

  

  /17

  $2,495,000

  • Land
  • 2.36 Acres
  • $1,057,203 per Acre

  4 Gold Medal Cir, Stratton, VT 05343

  This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont. Lot #4

  Andrew King Stratton Real Estate

  4 Gold Medal Cir, Stratton, VT 05343
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  /8

  $65,000

  • Land
  • 2 Acres
  • $32,500 per Acre

  585 Sawmill Rd, Stratton, VT 05360

  Ready to build! Nestled in the picturesque Snow Mountain Farms development, this prime 2 acre property offers the perfect canvas for your dream home. Situated in a great neighborhood with a convenient location, it provides easy access to both Mount Snow and Stratton. The property is equipped with a wastewater permit, septic design, an already cleared building envelope, and a driveway. Association

  Carrie Mathews Winhall Real Estate

  585 Sawmill Rd, Stratton, VT 05360
• 

  

  /4

  $400,000

  • Land
  • 8.01 Acres
  • $49,938 per Acre

  248 French Hollow Rd, Winhall, VT 05340

  Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

  Kim Morgan-Wohler Wohler Realty Group

  248 French Hollow Rd, Winhall, VT 05340
• 

  

  /13

  $120,000

  • Land
  • 4.68 Acres
  • $25,641 per Acre

  8559 Vt Route 30, Jamaica, VT 05343

  Double the Lots, Half the Drama.Why buy one lot when you can have two for the price of... well, this one? Here are 4.68 acres of "ready-to-go" land. Permits are secured for a 3 bedroom house on each lot, and the septic is already there, so you don't have to spend your weekends at town hall meetings. Build on both, or build on one and sell the other to that friend who always "forgets" their

  TG Glazer Winhall Real Estate

  8559 Vt Route 30, Jamaica, VT 05343
• 

  

  /12

  $325,000

  • Land
  • 3.42 Acres
  • $95,029 per Acre

  2366 Middletown Rd, Landgrove, VT 05148

  This property is within walking distance to the village of Londonderry and overlooks the town from its location approximately 500 paces up the hill on Middletown Road. The lot encompasses a hill that gives it privacy and security. Spring water flows to the base of the hill at one end of the propertyThe village commercial zoning gives the site options for multiple residential units (condos?),

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  2366 Middletown Rd, Landgrove, VT 05148
• 

  

  /60

  $8,200,000

  • 6 Beds
  • 10 Baths
  • 10,763 Sq Ft

  557 Trager Rd, Jamaica, VT 05343

  Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in

  Kim Morgan-Wohler Wohler Realty Group

  557 Trager Rd, Jamaica, VT 05343
• 

  

  /50

  $750,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  57 Pearl Buck Dr Unit 33, Bondville, VT 05340

  WAKE UP TO UNPRECEDENTED MOUNTAIN VIEWS once called Terra Bella with ownership over four decades and now this can be the Winhall/Stratton residence you have been searching for. From the moment you drive in you are captivated with incredible scenery off prestigious Pearl Buck Drive. Offered on 3.5 acres.The main level boasts newly refinished oak floors, two bedrooms, a den or living area with

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  57 Pearl Buck Dr Unit 33, Bondville, VT 05340
• 

  

  /15

  $530,000

  • Land
  • 30 Acres
  • $17,667 per Acre

  00 W Hill Rd S, Jamaica, VT 05343

  Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

  Jacki Murano Southern Vermont Realty Group

  00 W Hill Rd S, Jamaica, VT 05343
• 

  

  /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 chilly

  Robin Apps Four Seasons Sotheby's Int'l Realty

  25 Benson Fuller Dr, Jamaica, VT 05343
• 

  

  /12

  $299,999

  • Land
  • 10.05 Acres
  • $29,851 per Acre

  00 Garden Loop Rd, Winhall, VT 05340

  The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

  David White OwnerEntry.com

  00 Garden Loop Rd, Winhall, VT 05340
• 

  

  /9

  $195,000

  • Land
  • 1.2 Acres
  • $162,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
• 

  

  /8

  $150,000

  • Land
  • 2.26 Acres
  • $66,372 per Acre

  0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

  Welcome to the Stratton Gardens Community. Build your Vermont home on this 2+ acre parcel in Stratton Gardens. Ease of access right off the Stratton Mountain Access Road, and all the amenities of Stratton Gardens Association- highlights include-Private Shuttle Bus service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water Permit in place for approved

  Tara van de Velde Four Seasons Sotheby's Int'l Realty

  0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
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  /41

  $950,000

  • 4 Beds
  • 3.5 Baths
  • 3,031 Sq Ft

  7 Roundtree Rd, Winhall, VT 05340

  Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes—this property offers the best of Stratton living in every season.Step

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  7 Roundtree Rd, Winhall, VT 05340
• 

  

  /5

  $85,000

  • Land
  • 1 Acre
  • $85,000 per Acre

  000F-320 Bourbon Run Rd, Jamaica, VT 05343

  This 1-acre wooded lot in Jamaica, Vermont offers a unique opportunity for peaceful living in a quiet town with no zoning restrictions. Jamaica maintains its own roads and is home to a State Park that provides excellent camping and summer recreational activities. The property is conveniently located near major ski resorts including Stratton, Bromley, Magic Mountain, and Mount Snow, ideal for

  Mike England Michael England Real Estate

  000F-320 Bourbon Run Rd, Jamaica, VT 05343
• 

  

  /15

  $825,000

  • Land
  • 77.6 Acres
  • $10,631 per Acre

  0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340

  Large wooded parcel located in the heart of Southern Vermont’s ski country, just minutes from Stratton Mountain. This undeveloped Winhall property offers a rare opportunity for a variety of potential uses, from a private estate to recreational land or possible future development. The land consists primarily of wooded acreage with a gently rolling landscape and natural Vermont forest. Located on

  Trent Stephens Wohler Realty Group

  0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340
• 

  

  /21

  $379,000

  • Land
  • 12.05 Acres
  • $31,452 per Acre

  101 Catherine Rd, Jamaica, VT 05343

  Discover 12 scenic acres close to Stratton Mountain Resort with sweeping mountain views and endless potential. This unique property features a charming small treehouse and two Jamaica cottage structures set on permanent foundations ready to be finished. Cabin would be perfect for income producing tiny homes, storage, creative space, or future development. An active septic permit is already in

  Jamie Wylie Stratton Real Estate

  101 Catherine Rd, Jamaica, VT 05343
• 

  

  /15

  $500,000

  • Land
  • 21.2 Acres
  • $23,585 per Acre

  56 Lower Taylor Hill Rd, Winhall, VT 05340

  Set along Lower Taylor Hill Road in Winhall, this 21.2 +/- acre offering captures the privacy, natural beauty, and four-season lifestyle that define Southern Vermont living. Rolling terrain, mature woodland, and natural clearings create an exceptional setting for a private Vermont retreat, with the potential for Bromley Mountain views depending on house placement and design.Supported by a

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  56 Lower Taylor Hill Rd, Winhall, VT 05340
• 

  

  /6

  $229,000

  • Land
  • 1.57 Acres
  • $145,860 per Acre

  2 Gold Medal Cir, Stratton, VT 05343

  This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont. Find

  Andrew King Stratton Real Estate

  2 Gold Medal Cir, Stratton, VT 05343
• 

  

  /38

  $4,999,000

  • 6 Beds
  • 7.5 Baths
  • 8,720 Sq Ft

  454 Mountain Rd, Stratton, VT 05155

  Welcome to a one-of-a-kind 141-acre mountaintop retreat at Stratton Mountain Resort - an extraordinary sanctuary with panoramic views of Stratton, Mount Snow, and Bromley. Designed for elegance and ease, this home is a rare blend of architectural beauty, comfort, and sophistication. A gracious entryway opens to a sunlit living room and library anchored by an 18-foot stone fireplace. Expansive

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  454 Mountain Rd, Stratton, VT 05155
• 

  

  /5

  $375,000

  • Land
  • 5.54 Acres
  • $67,690 per Acre

  Lot #4 Margeaux Ln, Stratton, VT 05155

  Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you to begin

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  Lot #4 Margeaux Ln, Stratton, VT 05155
• 

  

  /16

  $139,000

  • Land
  • 1.62 Acres
  • $85,802 per Acre

  0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340

  wooded slightly elevated parcel. With clearing there should be some across valley views. Past soil test indicates proposed septic locations.Five-minute walk to Stratton snowmaking pond.

  Mike England Michael England Real Estate

  0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340
• 

  

  /60

  $979,000

  • 4 Beds
  • 3.5 Baths
  • 5,248 Sq Ft

  41-43 Cranberry Hill Rd, Winhall, VT 05340

  This is the ultimate modern Alpine chalet, fully renovated yet boasting the classic flat-sawn balusters characteristic of mountain homes in the Alps. Three expansive floors offer sunny, well-appointed space, beginning with a roomy mudroom, three bedrooms and two bathrooms (one en-suite). Head upstairs to join your friends and family in the open-concept European kitchen/living/dining room with

  Jamie Luke TPW Real Estate

  41-43 Cranberry Hill Rd, Winhall, VT 05340

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