Homes for Sale near The Mountain School at Winhall

• 

  

  

  /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
• 

  

  

  /41

  $8,950,000

  • 6 Beds
  • 10 Baths
  • 13,393 Sq Ft

  370 Fischer Ln, Jamaica, VT 05343

  Accessible, but miles from the everyday. Camp Endo’s mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark

  Dia Jenks LandVest, Inc/Woodstock

  370 Fischer Ln, Jamaica, VT 05343
• 

  

  

  /15

  $775,000

  • Land
  • 51.93 Acres
  • $14,924 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
• 

  

  

  /11

  $595,000

  • Land
  • 68.89 Acres
  • $8,637 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
• 

  

  

  /8

  $320,000

  • Land
  • 34.53 Acres
  • $9,267 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
• 

  

  /7

  $235,000

  • Land
  • 15.27 Acres
  • $15,390 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

  Thom Milke Fountains Land Inc.

  0 W Hill Rd, Jamaica, VT 05343
• 

  

  /17

  $659,000

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  761 Stratton Mountain Access Rd Unit 130, Stratton, VT 05360

  Location Location Location! A premiere property in the ever popular Long Trail House at Stratton Mountain Resort, Vermont. This two bedroom two bathroom condominium located on the first floor has direct access to the outdoor year round pool and hot tubs. The walkout access includes an open air as well as a covered patio with direct mountain views. The southern exposure provides wonderful natural

  Timothy Mich Doddridge Stratton Real Estate

  761 Stratton Mountain Access Rd Unit 130, Stratton, VT 05360
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  /14

  $815,000

  • 2 Beds
  • 2 Baths
  • 1,263 Sq Ft

  19 Village Lodge Rd Unit 309, Stratton, VT 05155

  In the heart of the Stratton Mountain Village attached to the iconic Clock Tower, Landmark is prime location for all that that the Resort has to offer. This two bedroom floorplan is one of the largest in the community. Ample living and bedroom space as well as a nice separate dining area. Direct mountain views with southern exposure for warm light. Beautifully appointed furniture and ready for

  Timothy Mich Doddridge Stratton Real Estate

  19 Village Lodge Rd Unit 309, Stratton, VT 05155
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  /44

  $1,200,000

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

  70 Hunter Ln, Jamaica, VT 05343

  Discover a truly special Vermont retreat at 70 Hunter Lane, nestled in the private Cole Pond community of Jamaica. This exceptional residence offers over 4,200 square feet of living space, thoughtfully designed to blend comfort, luxury, and the natural beauty of its surroundings. Newer Stainless Steel appliances in kitchen!Featuring four spacious bedrooms, this home provides plenty of

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  70 Hunter Ln, Jamaica, VT 05343
• 

  

  /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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  /30

  $1,040,000

  • 5 Beds
  • 4.5 Baths
  • 3,363 Sq Ft

  1189 Cole Pond Rd, Jamaica, VT 05343

  Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts.The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  1189 Cole Pond Rd, Jamaica, VT 05343
• 

  

  /43

  $920,000

  • 5 Beds
  • 4 Baths
  • 2,238 Sq Ft

  8 E Birch Rd Unit 103, Stratton, VT 05360

  Rare 5BR/4BA Stratton Townhome | Ski-Back Access | Designer Furnished | Spacious, fully renovated 5-bedroom, 4-bath townhome at Stratton with ski-back access. Professionally designed and furnished by ACK Design, this move-in-ready home blends mountain charm with modern finishes. The main level features hardwood floors, a stunning floor-to-ceiling stone fireplace, and a granite kitchen

  Cheyanne Pugliese

  8 E Birch Rd Unit 103, Stratton, VT 05360
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  /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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  /33

  $995,000

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  19 Village Lodge Rd Unit 407, Stratton, VT 05155

  Rare opportunity to own in the heart of the Stratton Mountain Village! Come home to the Landmark community. Located attached to the iconic "Clocktower" at Stratton, Vermont. This homes boasts three spacious bedrooms and two full bathrooms with amazing mountain views and southern exposure. Enjoy the cozy gas burning fireplace after a hard day skiing or riding. Landmark provides ski lockers, an

  Timothy Mich Doddridge Stratton Real Estate

  19 Village Lodge Rd Unit 407, Stratton, VT 05155
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  /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
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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
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  /60

  $1,825,000

  • 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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  /60

  $899,000

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

  42 Blackberry Ln, Jamaica, VT 05343

  Idyllic, Picturesque, Expansive, Vast Family Farm with outbuildings and Large Farmhouse! Known to some as Sweet Berry Farm the blueberries and blackberries are plentiful along with many other productive fruits trees, a grove of 20 mature apple trees with many over 30 years old, , flowers and veggies in the gardens. This location just off of Route 30 is perfect for ALL of your Vermont dreams and

  Steve Goldfarb Deerfield Valley Real Estate

  42 Blackberry Ln, Jamaica, VT 05343
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  /38

  $980,000

  • 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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  /42

  $899,000

  • 4 Beds
  • 3 Baths
  • 3,551 Sq Ft

  1247 Cole Pond Rd, Jamaica, VT 05343

  A once-in-a-lifetime opportunity to own a large family home on Vermonts hidden gem! Cole Pond, a spectacular private lake surrounded by mountains and nestled between five ski areas - 5 minutes from Stratton and close to Bromley, Mount Snow, Okemo and Magic. Cole Pond homes rarely come on the market, and this one is one-of-a-kind, with a lake-front lawn, walk-in access to the water (also great

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  1247 Cole Pond Rd, Jamaica, VT 05343
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  /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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  /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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  /27

  $250,000

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft

  8365 Vermont 30, Jamaica, VT 05343

  Quintessential Vermont Log Cabin Seeks New Relationship. I'm an adorable 2 bedroom, 1 bath home, located just 2 short miles from Stratton Mountain. I'm open to a variety of possibilities, including a full-time or seasonal resident. I'd also be a great fit for an investor. What I lack in size, I make up for in character. My open kitchen and living room layout is where I shine, and my

  TG Glazer Winhall Real Estate

  8365 Vermont 30, Jamaica, VT 05343
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  /4

  $210,000

  • 6 Beds
  • 3.5 Baths
  • 1,224 Sq Ft

  440 Edie Ln, Jamaica, VT 05343

  Property to be sold as is.

  Timothy Mich Doddridge Stratton Real Estate

  440 Edie Ln, Jamaica, VT 05343
• 

  

  /28

  $589,000

  • 2 Beds
  • 2 Baths
  • 1,131 Sq Ft

  771 Stratton Mountain Access Rd Unit 457, Stratton, VT 05360

  This two bedroom, two bath Long Trail condo places you at the heart of Stratton with unmatched convenience. Just a short walk to the slopes, it features heated underground garage parking, a year-round heated pool, sauna and hot tubs, and a welcoming hearth room, every detail is designed for ease and comfort. When it comes to location and lifestyle, it doesn't get any simpler than this.

  MaryKate Grey Stratton Real Estate

  771 Stratton Mountain Access Rd Unit 457, Stratton, VT 05360
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  /52

  $1,725,000

  • 4 Beds
  • 3.5 Baths
  • 2,698 Sq Ft

  122 Sunbowl Ridge Rd, Stratton, VT 05360

  Solstice has long been considered the very finest townhome development at Stratton Mountain. With an unparalleled slope side location and private amenities such as heated pool and tub , private shuttle service. This four bedroom four bath townhome is the ultimate ski and summer getaway. Beautifully redone. One car heated garage, family room.

  John Sikes Stratton Real Estate

  122 Sunbowl Ridge Rd, Stratton, VT 05360
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  /42

  $1,150,000

  • 3 Beds
  • 3 Baths
  • 2,121 Sq Ft

  4 Hardwood Hill, Stratton, VT 05360

  Welcome to your mountain retreat in the exclusive TreeTop community at Stratton Resort. This upscale 3 level, 3 BR, 3 BA + bonus loft room townhome offers the perfect blend of alpine charm & modern comfort. Perched on the mountain with panoramic vistas, enjoy year-round views from your private stone patio & spacious deck. Step outside & take advantage of ski-back access right to your door, plus a

  Kim Morgan-Wohler Wohler Realty Group

  4 Hardwood Hill, Stratton, VT 05360
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  /39

  $650,000

  • 5 Beds
  • 3.5 Baths
  • 2,468 Sq Ft

  17 Signal Hill Rd, Winhall, VT 05340

  17 Signal Hill Road offers Vermont charm in a secluded mountain setting. With over 2,400 square feet of living space, this five-bedroom, three-and-a-half-bath home has been thoughtfully maintained and move-in ready. The main level features a spacious living room with a dramatic fieldstone fireplace, vaulted ceilings, and skylights that fill the home with natural light. A loft overlooking

  Christiane Carroccio TPW Real Estate

  17 Signal Hill Rd, Winhall, VT 05340
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  /33

  $59,900

  • 2 Beds
  • 0.5 Baths
  • 414 Sq Ft

  33 W River St, Londonderry, VT 05155

  Welcome to the “Love Shack,” a rustic riverfront cabin nestled along the banks of the West River in the heart of South Londonderry, Vermont. This one-of-a-kind retreat offers a rare chance to unplug and embrace the simple joys of cabin living while staying close to everything southern Vermont has to offer. Located just six minutes from Magic Mountain and within easy reach of Bromley, Stratton,

  Christine Chovan

  33 W River St, Londonderry, VT 05155
• 

  

  /29

  $465,000

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft

  132 Pratt Bridge Rd, Jamaica, VT 05343

  Welcome to this charming Vermont getaway, custom - built and lovingly maintained by the original owners. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley and Magic for a full season of winter adventure. In the warmer months, enjoy nearby lakes perfect for swimming, paddling, or simply relaxing by the water.Inside, the home offers 3 bedrooms and 2 full

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  132 Pratt Bridge Rd, Jamaica, VT 05343
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  /21

  $465,000

  • 4 Beds
  • 2 Baths
  • 1,337 Sq Ft

  3 Old Town Rd, Bondville, VT 05340

  This house is a must see for anyone looking for a small home in Vermont. Located between Stratton and Bromley and just minutes away from Magic Mountain, the location is prime ski country often referred to as the Golden Triangle.With four bedrooms and an open concept living room and kitchen, this home is cozy and inviting. Fully renovated and turnkey. Fenced in yard with hot tub. Fire

  Andrew King Stratton Real Estate

  3 Old Town Rd, Bondville, VT 05340
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  /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.

  Andrew King Stratton Real Estate

  4 Gold Medal Cir, Stratton, VT 05343
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  /40

  $615,000

  • 3 Beds
  • 3 Baths
  • 1,886 Sq Ft

  4A Ridge, Winhall, VT 05340

  4A Ridge Court is a welcoming townhouse in the highly desirable Piper Ridge community, just minutes from Stratton Mountain Base lodge and everything the area has to offer. This 3-bedroom, 3-bath furnished home features en-suite bedrooms, providing comfort and privacy for family and guests. The main level features a bright living room with wood-beamed cathedral ceilings, a wood-burning fireplace,

  Christiane Carroccio TPW Real Estate

  4A Ridge, Winhall, VT 05340
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  /10

  $360,000

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft

  85 E Birch Rd Unit 15, Stratton, VT 05360

  Neighboring the Stratton Training and Fitness Center, Vantage Point offers two bedroom, two bath condominiums coveted for their convenience and southern exposure. Complete with large windows, wood burning fireplaces, full kitchens, and ample closet space, these units are perfect for growing families and couples who like to entertain. Residents enjoy private parking and complimentary shuttle to

  Edwin Kevil Stratton Real Estate

  85 E Birch Rd Unit 15, Stratton, VT 05360
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  /35

  $625,000

  • 3 Beds
  • 3 Baths
  • 2,939 Sq Ft

  282 Melendy Hill Rd, South Londonderry, VT 05155

  Perfectly situated in the heart of Southern Vermont, this immaculate country Cape in South Londonderry offers the best of four-season living. Just minutes to Stratton, Magic, and Bromley Mountains, the property provides effortless access to skiing and snowboarding in winter. In summer, enjoy kayaking at Lowell Lake, golf at Stratton, or live theater at the Weston Playhouse. Everyday conveniences

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  282 Melendy Hill Rd, South Londonderry, VT 05155
• 

  

  /15

  $485,000

  • 2 Beds
  • 2 Baths
  • 1,353 Sq Ft

  49 High Point Dr Unit A-14, Stratton, VT 05360

  49 High Point Drive, Crown Point A14, Stratton, VTIncredible opportunity to make Stratton Mountain Resort a place to call home. Nestled in the Green Mountains of Vermont, Crown Point offers easy condominium living close to the Stratton Mountain Resort Village. Shuttle service to the base area for skiing and riding. An outdoor pool and BBQ area is inviting for summer use. This one-level 2

  Andrew King Stratton Real Estate

  49 High Point Dr Unit A-14, Stratton, VT 05360
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  /9

  $84,900

  • Land
  • 1.78 Acres
  • $47,697 per Acre

  0000 Wonder Ln Unit Lot 18, Jamaica, VT 05343

  Prime 1.78-Acre Wooded Lot near Stratton Mountain Ski Resort and Golf Course---Nestled down a serene and private dirt road, this magnificent 1.78-acre wooded lot offers an unparalleled opportunity to build your dream home amidst Vermont's natural beauty. Located conveniently close to the renowned Stratton Mountain Ski Resort and Golf Course, this property promises year-round recreation and

  Rachel Febbie EXP Realty

  0000 Wonder Ln Unit Lot 18, Jamaica, VT 05343
• 

  

  /60

  $685,000

  • 3 Beds
  • 2.5 Baths
  • 2,034 Sq Ft

  3 Short Rd, Bondville, VT 05340

  Charming Vermont Homestead: Ideal for Ski Lovers or Those Seeking a Homesteading Lifestyle Escape to the serene beauty of Vermont with this renovated Cape located in Winhall, offering a perfect blend of rustic charm and modern updates. This home is ideal for anyone looking for a home near the slopes or a peaceful getaway with room to relax.Modern Updates Meet Classic Vermont

  Mike England Michael England Real Estate

  3 Short Rd, Bondville, VT 05340
• 

  

  /39

  $699,000

  • 6 Beds
  • 3 Baths
  • 2,825 Sq Ft

  95 Melendy Hill Rd, Londonderry, VT 05155

  A fully reimagined 1900’s farmhouse located in the heart of South Londonderry. This six-bedroom, three-bath home has been meticulously remodeled to blend timeless character with contemporary style. Sunlight pours through all-new windows, illuminating generous living spaces. Every detail has been thoughtfully upgraded, from the new heating system, engineered and installed septic, well, and

  Jessica Citera Cummings & Co

  95 Melendy Hill Rd, Londonderry, VT 05155
• 

  

  /20

  $590,000

  • 2 Beds
  • 2 Baths
  • 920 Sq Ft

  771 Stratton Mountain Access Rd Unit 361, Stratton, VT 05360

  Experience the best of mountain living at Long Trail House. This light-filled 2-bedroom, 2-bath condo offers comfort, convenience, and an unbeatable location just steps from Stratton’s lifts, shops, and restaurants. The open-concept living area features a gas fireplace, perfect for cozy apres-ski gatherings, and a well-equipped kitchen with a breakfast bar for casual dining. This corner unit has

  Christiane Carroccio TPW Real Estate

  771 Stratton Mountain Access Rd Unit 361, Stratton, VT 05360

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