Newest Homes for Sale in South Londonderry, VT

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  /9

  $500,000

  • Land
  • 20.2 Acres
  • $24,752 per Acre

  0 W Hill Rd, Jamaica, VT 05343

  Mike England Michael England Real Estate

  0 W Hill Rd, Jamaica, VT 05343
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  /54

  $3,495,000

  • 6 Beds
  • 6.5 Baths
  • 5,660 Sq Ft

  168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360

  Experience true mountain luxury in this stunning six bedroom six bathroom slope side single family home, perfectly positioned for effortless access to world-class skiing and snowboarding at the Stratton Mountain Resort. Designed with comfort and style in mind, this residence combines refined alpine architecture with modern amenities including a gym, steam shower, pool table that doubles as table

  Timothy Mich Doddridge Stratton Real Estate

  168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360
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  /23

  $695,000

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

  57 Pearl Buck Dr, Bondville, VT 05340

  Perched high on Pearl Buck Drive, this distinctive Vermont home is all about location—and the scenery is truly exceptional. Sweeping mountain vistas capture both Stratton and Bromley, creating a dramatic backdrop in every season, from autumn color and snow-covered peaks to long summer sunsets. The road also carries a special local connection to Pearl S. Buck, the Pulitzer- and Nobel Prize-winning

  Carrie Mathews Winhall Real Estate

  57 Pearl Buck Dr, Bondville, VT 05340
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  /60

  $1,150,000

  • 4 Beds
  • 5.5 Baths
  • 3,206 Sq Ft

  11 Spruce High Rd, Winhall, VT 05340

  Discover this truly exceptional Vermont Mountain Retreat just seven miles from Stratton Mountain, perfectly located for four-season living! Boasting an inviting open layout great for spending time together, southern exposure and an abundance of natural light this beautifully renovated home has been updated in a sophisticated Vermont rustic style with all the comforts. Enjoy the Luxurious primary

  Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

  11 Spruce High Rd, Winhall, VT 05340
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  /12

  $679,000

  • 3 Beds
  • 3 Baths
  • 1,830 Sq Ft

  G6 Cobble Ridge Rd Unit G6, Winhall, VT 05340

  This 3-bedroom,3-bathroom, Tri-level Piper Ridge "Tunbridge" Townhome/Condo has a full facing view of the face of Stratton Mountain. It is basically in original condition. It is completely empty and the interior has just been completely painted. The family is aware that some upgrades will be required to accommodate new owner's taste. The listed price of $679,000-below assessment- {$757,600} -

  Eric Nathan Nathan Auction & Real Estate Inc.

  G6 Cobble Ridge Rd Unit G6, Winhall, VT 05340
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  /30

  $995,000

  • 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
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  /15

  $119,000

  • Land
  • 10.9 Acres
  • $10,917 per Acre

  0 Under the Mountain Rd, South Londonderry, VT 05155

  10+ acres on beautiful Under the Mountain Road, home to horse farms, stone walls, and pure country charm! This property offers a blank slate to bring your vision to life; whether you are looking to build a small efficient home, a large country estate, or a self-sufficient homestead. There is a small rustic camp already on the property, and a small wetland area towards the back. Bordered by

  Rebecca Seymour Brattleboro Area Realty

  0 Under the Mountain Rd, South Londonderry, VT 05155
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  /39

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft

  18 Old Snow Valley Rd, Winhall, VT 05340

  ***Open House Sunday 9/6/26 11:00-1:00***Charming, comfortable, and ideally situated, this expanded 3-bedroom, 2-bath A-frame captures the essence of a Vermont retreat. Perfectly located just 6 minutes to Bromley, 8 minutes to Manchester Center, and aprox 15 minutes to Stratton Mountain, endless mountain recreation and dining are right at your doorstep.A spacious enclosed porch doubles as

  

  Lauren Behm

  Berkshire Hathaway HomeServices Stratton Home

  18 Old Snow Valley Rd, Winhall, VT 05340
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  /16

  $975,000

  • Land
  • 235.3 Acres
  • $4,144 per Acre

  00 Pratt Bridge Rd, Jamaica, VT 05343

  Enjoy Vermont in all the seasons!! This land has a number of options! With 235 acres to call your own! Build somewhere on the property. A stream runs through for your enjoyment! Part of the West River Trail passes through as well. Harvest timber from this lot and make some $$. Pratt Bridge Road is a close drive to Stratton, Magic or Bromley in the winter and enjoy spring, summer and fall

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  00 Pratt Bridge Rd, Jamaica, VT 05343
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  /43

  $1,050,000

  • 4 Beds
  • 4 Baths
  • 2,380 Sq Ft

  20 W Branch Rd, Winhall, VT 05340

  Escape to the mountains and enjoy everything Stratton, Vermont has to offer in this fabulous 4 bedroom, 4 bath contemporary home, ideally located on a private cul-de-sac in the heart of Stratton Resort. Designed for gathering with family and friends, the home features a spacious open floor plan with a cathedral-ceiling living room, wood-burning fireplace, open kitchen and dining area, and plenty

  MaryKate Grey Stratton Real Estate

  20 W Branch Rd, Winhall, VT 05340
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  /30

  $289,000

  • 2 Beds
  • 1 Bath
  • 696 Sq Ft

  398 Tallwood Cir, Londonderry, VT 05148

  Welcome to 398 Tallwood Circle, a cozy Vermont retreat tucked into a quiet country setting in Londonderry. Set on 1.5 acres with a wooded backdrop, this 2-bedroom, 1-bath home offers privacy, character, and an ideal base for enjoying Southern Vermont.Inside, an inviting open living area features a vaulted wood ceiling, abundant natural light, and a wood stove for warmth and classic

  Grayson VanHendrick Flex Realty

  398 Tallwood Cir, Londonderry, VT 05148
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  /26

  $749,000

  • 3 Beds
  • 2 Baths
  • 976 Sq Ft

  7 Wood Rock Rd, Winhall, VT 05340

  A rare Stratton ownership opportunity with exceptional amenities and possibilities. The purchase presents an opportunity for the buyer to bypass the Stratton Mountain Club waiting list, subject to Club approval and payment of all associated fees.. Also included with the property is an active Stratton Mountain Homeowner Membership Bond, with the buyer responsible for the applicable transfer

  Jamie Wylie Stratton Real Estate

  7 Wood Rock Rd, Winhall, VT 05340
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  /60

  $2,430,000

  $270K PRICE DROP

  • 9 Beds
  • 7 Baths
  • 4,996 Sq Ft

  494-564 Goodaleville Rd, Jamaica, VT 05343

  TWO HOMES | 1BR BARN APARTMENT | RESTORED VINTAGE BARN | 13+ ACRES. A rare Vermont multi-residence estate offering two beautifully renovated homes, a separate 1BR barn apartment, a restored vintage barn, and more than 13 acres along the Winhall River. Thoughtfully renovated by Vermont Country Builders, Winhall River Farm blends authentic character, exceptional craftsmanship, and modern

  Cheyanne Pugliese

  494-564 Goodaleville Rd, Jamaica, VT 05343
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  /40

  $1,325,000

  • 4 Beds
  • 3.5 Baths
  • 3,400 Sq Ft

  11 W Round Rd, Winhall, VT 05340

  11 Round Tree Road, Winhall, VT 05340A landmark on Round Tree Road, this house has inviting curb appeal with its stone façade and archway. With 1.83 acres the house has a very private setting in back for the patio, fire pit and hot tub. Unique U-shaped driveway has plenty of room for friends and family. Appropriately sized mud room for all the gear. Downstairs family room with fireplace and

  Andrew King Stratton Real Estate

  11 W Round Rd, Winhall, VT 05340
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  /10

  $190,000

  • Land
  • 3.8 Acres
  • $50,000 per Acre

  148 Vt Route 30, Winhall, VT 05340

  This exceptional 3.8-acre, partially-cleared Winhall lot offers potentially unobstructed views of Stratton mountain, and is permitted for a 4BR home perched at the top of the lot's slope. Nestled in pines, spruces, birches and maple trees, this private Vermont retreat offers an enviable sense of seclusion and natural beauty away from it all, yet with easy proximity to four seasons of fun

  Jamie Luke TPW Real Estate

  148 Vt Route 30, Winhall, VT 05340
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  /47

  $1,465,000

  • 4 Beds
  • 4 Baths
  • 2,625 Sq Ft

  4 Basswood Row Unit 4A, Stratton, VT 05360

  Experience true resort living in this luxury 4 bedroom, 4 bathroom alpine residence in Stratton’s sought after Treetop community. Designed with sweeping mountain views and seamless ski home access, this townhouse eliminates the morning scramble so you can spend your days carving first tracks and your evenings unwinding in comfort.Imagine starting your morning in a snowy winter wonderland.

  Robin Apps Four Seasons Sotheby's Int'l Realty

  4 Basswood Row Unit 4A, Stratton, VT 05360
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  /11

  $240,000

  • Land
  • 10.06 Acres
  • $23,857 per Acre

  0 Stratton Gardens Rd Unit 35, Winhall, VT 05340

  This expansive building lot, situated just off the Stratton Access Road, offers breathtaking views of Bromley Mountain, presenting an ideal opportunity to construct your dream home in the picturesque setting of Stratton, Vermont. The property is designated for a five-bedroom residence, with the necessary State Waste permit (WW-2-1972-14) already in place, ensuring a smooth development process.

  Mike England Michael England Real Estate

  0 Stratton Gardens Rd Unit 35, Winhall, VT 05340
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  /40

  $535,000

  • 4 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  619 Main St, South Londonderry, VT 05155

  Set on 3 lovely acres in the heart of South Londonderry, this gracious four-bedroom, 2½-bath Victorian blends timeless character with thoughtful modern updates. Original floor-to-ceiling windows, soaring ceilings, hardwood floors, and classic Victorian details create a warm and inviting sense of history throughout the home.The newly renovated kitchen provides a fresh, functional gathering

  

  Alison Cummings

  Cummings & Co

  619 Main St, South Londonderry, VT 05155
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  /26

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  33 Burnt Hill Ln, Winhall, VT 05340

  Experience four season Vermont living at 33 Burnt Hill Road in Strattonwald, a recreational community in Winhall just minutes from Stratton Mountain. Set on 1.09 wooded acres, this three bedroom, two bath mountain home combines privacy and Vermont character with access to the Strattonwald swimming pond and beach, tennis courts and winter shuttle service to Stratton.Inside, natural wood,

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  33 Burnt Hill Ln, Winhall, VT 05340
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  /34

  $345,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  19 Winhall Condo Rd Unit 4, Winhall, VT 05340

  Tucked at the end of a quiet back road less than one mile from the Stratton Access Road, The Winhall Condos offer a peaceful mountain retreat with convenient access to both Stratton and Manchester. This updated 2-bedroom, 2-bath residence features an open-concept kitchen, living, and dining area, two elevated decks, and beautiful views of Stratton Mountain. Offered furnished and ready to enjoy,

  Cheyanne Pugliese

  19 Winhall Condo Rd Unit 4, Winhall, VT 05340
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  /54

  $875,000

  • 3 Beds
  • 3.5 Baths
  • 3,916 Sq Ft

  30 Fieldstone Way, Londonderry, VT 05155

  Set in the peaceful Vermont countryside of Londonderry, this contemporary home offers the perfect blend of spacious living, natural beauty, and convenient access to some of Southern Vermont’s ski areas. Situated on 1.58 acres between Magic Mountain, Bromley, and Stratton, the property is ideally positioned for year-round recreation and relaxation.Built in 2004, the 4,094-square-foot home

  David Shehadi Josiah Allen Real Estate, Inc.

  30 Fieldstone Way, Londonderry, VT 05155
• 

  

  /40

  $595,000

  $20K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  23 Loop Rd Unit 10, Bondville, VT 05340

  Set among sun-dappled woodlands along a peaceful country road, this distinctive post-and-beam home captures the charm of a Vermont sugar shack with the warmth of a classic ski-country retreat. This furnished three bedroom, two bath home offers 1,416 sq ft of inviting living space, thoughtfully designed for both full-time living and memorable getaways. Inside, the vaulted Great Room immediately

  Diana Stugger Four Seasons Sotheby's Int'l Realty

  23 Loop Rd Unit 10, Bondville, VT 05340
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  /24

  $829,000

  • 4 Beds
  • 2 Baths
  • 1,638 Sq Ft

  12 Ober Tal Dr Unit C/23C/24, Stratton, VT 05360

  Unmatched Comfort and Convenience at Stratton's Ober Tal - trailside propertyDiscover the ideal ski retreat in this bright, spacious, one-of-a-kind double unit at Ober Tal, Building C. Next to the Tamarack ski lift, you’ll enjoy unbeatable access to the slopes and all the amenities in Stratton Village.Close enough to swing back for a quick lunch, this condo lets you make the most

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  12 Ober Tal Dr Unit C/23C/24, Stratton, VT 05360
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  /32

  $765,000

  • 3 Beds
  • 3 Baths
  • 2,322 Sq Ft

  72 Benson Fuller Dr, Winhall, VT 05340

  Set among the trees just minutes from Stratton Resort, this spacious 3-bedroom, 3-bath mountain home combines beautiful views, flexible living spaces and plenty of room for family and friends. The dramatic main living area features soaring vaulted ceilings, warm wood accents, a floor-to-ceiling stone fireplace and an impressive wall of windows that fills the home with natural light and brings the

  Christine Chovan

  72 Benson Fuller Dr, Winhall, VT 05340
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  /35

  $725,000

  • 2 Beds
  • 2 Baths
  • 1,071 Sq Ft

  771 Stratton Mountain Access Rd Unit 472, Stratton, VT 05360

  Hang up your keys for the weekend and enjoy one of Stratton’s most convenient locations. Walk to the slopes and Stratton Village for skiing, dining, shopping, and year-round activities. This quiet, top-floor end unit at Long Trail House is filled with natural light and offers wide mountain views, including the front face of Stratton. The desirable two-bedroom, two-bath layout is an ideal choice

  Cheyanne Pugliese

  771 Stratton Mountain Access Rd Unit 472, Stratton, VT 05360
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  /12

  $645,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  776 Stratton Mountain Access Rd Unit 1102, Stratton, VT 05155

  Immaculate two bedroom, two bath ski in, ski out condominium steps from the snow front and Stratton Village Square with its shops and restaurants. Ski home for lunch! Mudroom and full laundry facilities, serve through kitchen, two ensuite baths. One of Stratton resort's most sought after properties. Sold furnished, turnkey. Excellent rental potential.

  John Sikes Stratton Real Estate

  776 Stratton Mountain Access Rd Unit 1102, Stratton, VT 05155
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  /60

  $5,575,000

  • 7 Beds
  • 9.5 Baths
  • 9,915 Sq Ft

  159 Winhall Hollow Rd, Bondville, VT 05340

  Privately situated in a most beautiful setting, this grand Vermont estate commands a remarkable landscape, with Stratton Mountain rising majestically beyond the tree line. A sweeping private drive sets the tone for an extraordinary arrival; open meadows, a serene pond, and beautifully preserved grounds before revealing the 9915 SF residence itself and massive barn. There's an immediate sense of

  Kim Morgan-Wohler Wohler Realty Group

  159 Winhall Hollow Rd, Bondville, VT 05340
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  /25

  $1,200,000

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

  11 Founders Hill Rd, Winhall, VT 05360

  Selling very close to the assessed value of $1,126,100!!! This 2026 town assessment just made this property a REAL DEAL because the Owner wants 1,200,000. This property can be sold furnished or unfurnished with closing before the ski season is here. 6 bedrooms and 3.5 bathrooms to accommodate your family and guests. Enjoy 2 primary suites with attached baths and one is on the main floor. Walk in

  Derek Greene Derek Greene

  11 Founders Hill Rd, Winhall, VT 05360
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  /51

  $5,100,000

  • 10 Beds
  • 9.5 Baths
  • 6,648 Sq Ft

  15 Sawmill Rd, Stratton, VT 05155

  Location, Location, Location. Representing the pinnacle of Stratton Mountain trailside living, 15 Sawmill is a generational property where unrivaled ski-in/ski-out access creates one of Stratton's most exceptional legacy offerings. This is one of the few homes located along the trail - one you admire and wish was yours when you ski by it all winter season! Perfectly positioned directly on the ski

  Kim Morgan-Wohler Wohler Realty Group

  15 Sawmill Rd, Stratton, VT 05155
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  /42

  $1,115,000

  $135K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,022 Sq Ft

  564 Goodaleville Rd, Jamaica, VT 05343

  Set along a quiet back road on the Winhall River, this beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes from

  Cheyanne Pugliese

  564 Goodaleville Rd, Jamaica, VT 05343
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  /53

  $1,315,000

  $135K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 2,974 Sq Ft

  494-498 Goodaleville Rd, Jamaica, VT 05343

  4BR MAIN HOUSE, 1BR BARN APARTMENT, AND SEPARATE RESTORED VINTAGE BARN | Tucked along a quiet back road with the gentle sounds of the flowing Winhall River, this beautifully restored Vermont farmhouse feels worlds away, yet is just 10 minutes from Stratton Mountain Resort. Blending authentic character, exceptional craftsmanship, and modern comfort, the property offers a rare sense of privacy and

  Cheyanne Pugliese

  494-498 Goodaleville Rd, Jamaica, VT 05343
• 

  

  /40

  $1,699,000

  • 4 Beds
  • 4 Baths
  • 2,951 Sq Ft

  1949 South Rd, Peru, VT 05152

  Discover Berry Hill Farm, an exceptional Vermont estate where inspired design, extraordinary craftsmanship, and natural beauty come together in one remarkable setting. Offering privacy, versatility, and a deep connection to the landscape, this unique property encompasses 15.52 acres across two separately deeded parcels, creating a rare offering for a Southern Vermont retreat. The contemporary

  Helen Nault

  1949 South Rd, Peru, VT 05152
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  /31

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,110 Sq Ft

  65 E Birch Rd Unit 43, Stratton, VT 05155

  Welcome to Your Stratton Mountain GetawayDiscover the ultimate in mountain convenience with this turnkey, ground level condo in the highly sought after Vantage Point community. Featuring a spacious 2 bedroom, 2 bathroom layout, this home boasts a bright, open concept living, dining, and kitchen area designed for effortless entertaining and relaxation. Positioned in an unbeatable location,

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  65 E Birch Rd Unit 43, Stratton, VT 05155
• 

  

  /3

  $735,000

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

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

  Incredible combination of location and amenities. Walk across the street to the ski slopes and Stratton Village with its shops, restaurants, and year-round activities. This top-floor condominium features soaring ceilings, abundant natural light, and a desirable two-bedroom, two-bath layout. Long Trail offers a year-round heated outdoor pool, hot tubs, and a sauna. Heated underground parking, ski

  Cheyanne Pugliese

  771 Stratton Mountain Access Rd Unit 457, Stratton, VT 05360
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  /4

  $20,000

  $30K PRICE DROP

  • Land
  • 43,124 Sq Ft
  • $20,202 per Acre

  0 Route 30 Unit 5099207, Winhall, VT 05340

  Wooded one acre parcel off Rt 30 in Winhall, just past the west entrance to French Hollow Rd. and by Green Mountain National Forest and VTRT 30. This is a sloping /wooded parcel that extends down to the Mill Brook. There seems to be a nice plateau/bench as a possible build site........All Buyers should/must do their Own due diligence.

  Mike England Michael England Real Estate

  0 Route 30 Unit 5099207, Winhall, VT 05340
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  /46

  $1,599,000

  • 6 Beds
  • 5.5 Baths
  • 5,568 Sq Ft

  144 High Meadow Rd, Winhall, VT 05340

  Expansive Stratton Mountain Resort Residence with exceptional floor plan and renovation! Featuring an upscale redesign of two top floor primary suite bathrooms, updated kitchen and expanded finished lower level, this home is ready for mountain living and endless entertaining! Designed with multiple gathering rooms and fireplaces, you'll enjoy apres ski with and an incredible open floor plan. Game

  Kim Morgan-Wohler Wohler Realty Group

  144 High Meadow Rd, Winhall, VT 05340
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  /31

  $680,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155

  Nestled right on the slopes of Stratton Mountain Resort, this two bedroom two ensuite bathroom condominium offers true ski-in/ski-out convenience for your winter getaway. You'll find yourself just steps from the Villager chairlift, beginner ski area as well as a stone's throw to the shops and restaurants in the Stratton Village. An open-concept living/dinning/kitchen area that features a stone

  Timothy Mich Doddridge Stratton Real Estate

  778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155
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  /52

  $565,000

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

  1886 Winhall Hollow Rd, South Londonderry, VT 05155

  Great Location, New Roof, New Septic, recent exterior painting! This turn key residence is ideally located between three ski areas and near schools and shopping. Gourmet kitchen, wood floors, upscale baths and a huge 3 car garage/ barn with finished office space. Tucked amidst the forest with views of Magic Mountain's ridge line, whether you are looking for a second home in the mountains or

  Kim Morgan-Wohler Wohler Realty Group

  1886 Winhall Hollow Rd, South Londonderry, VT 05155
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  /38

  $795,000

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

  25 Benson Fuller Dr, Bondville, VT 05340

  Where Mountains Meet Modern Living: Perched just moments from the energy of Stratton Mountain Resort, this contemporary mountain home reimagines what a Vermont getaway feels like. From the moment you step inside, the design does exactly what a great contemporary home should: it steps back and lets nature take center stage. Massive, soaring windows act as living art pieces, framing sweeping,

  Robin Apps Four Seasons Sotheby's Int'l Realty

  25 Benson Fuller Dr, Bondville, VT 05340
• 

  

  /21

  $152,000

  $8K PRICE DROP

  • Land
  • 11.08 Acres
  • $13,718 per Acre

  0 Rose Ln Unit 5097818, Londonderry, VT 05148

  This 11-acre parcel is situated near Cole Pond, only a few miles from the Stratton Mountain Access Road. The lot offers several potential building sites, including an elevated area that boasts stunning views, as well as a lower option. A driveway extends approximately halfway up the property, providing access to the upper site, which features a remarkable vista of Bromley Mountain. As one

  Mike England Michael England Real Estate

  0 Rose Ln Unit 5097818, Londonderry, VT 05148

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