South Londonderry, VT Homes for Sale

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  $559,000

  • 3 Beds
  • 3 Baths
  • 2,704 Sq Ft

  4138 W Hill Rd S, Jamaica, VT 05343

  Nestled on 2.37 private acres in a serene mountain setting just minutes from skiing, this custom-built three-bedroom, three-bath log home offers the perfect blend of rustic charm and comfort. Constructed with double tongue-and-groove logs, the home showcases the rich wood interior and craftsmanship you would expect in a classic mountain retreat.The open-concept main level centers around a

  Patricia Fitzpatrick Skihome Realty

  4138 W Hill Rd S, Jamaica, VT 05343
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  /39

  $895,000

  • 4 Beds
  • 4 Baths
  • 2,673 Sq Ft

  F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340

  Own your piece of Piper Ridge, a prestigious condo complex, in Stratton, Vermont. This 4-bedroom, 4-bathroom townhome received significant improvements over the past two years, making it move-in ready for maximum relaxation in the mountains. This spacious open floor plan has been upgraded with new hardwood flooring on the first and second floors and kitchen renovations with new countertops and

  Mike England Michael England Real Estate

  F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340
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  /40

  $1,150,000

  • 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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  $175,000

  • Land
  • 2.26 Acres
  • $77,434 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-Shuttle service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water permit in place for a 4 bedroom home.

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

  0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
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  $890,000

  • 5 Beds
  • 3.5 Baths
  • 3,218 Sq Ft

  4880 Pikes Falls Rd, Jamaica, VT 05343

  This majestic log home offers peaceful mountain living with room for Everyone. Discover your tranquil 5-bedroom, 4-bathroom family retreat nestled just minutes from the year-round activities at Stratton Ski Resort. This authentic and expansive log cabin exudes classic Vermont charm. The inviting main living area is flooded with natural light, featuring an efficient wood stove to provide cozy

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  4880 Pikes Falls Rd, Jamaica, VT 05343
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  /36

  $998,500

  • 4 Beds
  • 3.5 Baths
  • 2,070 Sq Ft

  32 Shattarack Rd Unit B5, Stratton, VT 05360

  They say beauty is only skin deep, but not in the case of this meticulously renovated Slopeside residence, which offers a rare combination of quality, comfort, and location. With more than $500,000 invested, this home delivers far more than surface-level appeal — the kind of work that is not always seen but is most certainly felt. Every system and surface has been thoughtfully addressed. Unlike

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  32 Shattarack Rd Unit B5, Stratton, VT 05360
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  $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
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  /5

  $55,000

  • Land
  • 1 Acre
  • $55,000 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
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  /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
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  $555,000

  • 3 Beds
  • 3 Baths
  • 2,341 Sq Ft

  49 High Point Dr Unit A122, Stratton, VT 05360

  Crown Point, Stratton Vermont. Enjoy this two-level, three bedroom, three bath condo and BONUS "4th" room with direct access to bath. This home has an upper and lower entry, both with plenty of storage for outdoor gear. The upper level opens into the kitchen, dining area, and living room with wood burning fireplace and a small deck. The primary ensuite bedroom, with a jacuzzi tub, is also on the

  Mike England Michael England Real Estate

  49 High Point Dr Unit A122, Stratton, VT 05360
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  /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
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  $3,750,000

  • 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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  $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
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  /15

  $500,000

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

  56 Lower Taylor Hill Rd, Winhall, VT 05340

  A rare opportunity to create a private Vermont retreat on 21.2 +/- acres along Lower Taylor Hill Road in Winhall. The property is supported by a State-approved wastewater permit for a six (6) bedroom single-family residence, offering flexibility to design a substantial home within permitted limits. Rolling terrain, natural clearings, and mature woodland provide multiple potential building sites,

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  56 Lower Taylor Hill Rd, Winhall, VT 05340
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  $995,000

  • 5 Beds
  • 4.5 Baths
  • 2,321 Sq Ft

  24 N Branch Rd, Winhall, VT 05340

  Location says it all ! Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. This exceptional renovation offers an expanded floor plan with a third level.Beautiful upscale baths with tile work and craftsmanship of the highest caliber. Wood floors throughout. Open gourmet kitchen makes for premier apres ski gatherings. With 5 bedrooms/4 baths and multiple ensuite-

  Kim Morgan-Wohler Wohler Realty Group

  24 N Branch Rd, Winhall, VT 05340
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  $1,250,000

  • 4 Beds
  • 3.5 Baths
  • 3,516 Sq Ft

  732 Under the Mountain Rd, South Londonderry, VT 05155

  With 42+ stunning acres and unrivaled panoramic mountain (and sunset) views, this beautiful historic home seamlessly blends an extraordinary sense of history, grace, modern amenities, and will offer you the quintessential Vermont experience! Originally built in 1810 and artfully reimagined in 1987, the 5BR farmhouse features exposed beams, wide plank wood floors, and architectural character, and

  Claudia Harris Mary Mitchell Miller Real Estate

  732 Under the Mountain Rd, South Londonderry, VT 05155
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  $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
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  $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 seamless

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  1189 Cole Pond Rd, Jamaica, VT 05343
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  $849,000

  • 4 Beds
  • 3 Baths
  • 2,797 Sq Ft

  13 Betty Johnson Ln, Bondville, VT 05340

  Experience the magic of Vermont in every season with this stunning four-bedroom, three-bathroom home directly on Stratton Mountain. Your ultimate year-round retreat. Nestled in the heart of Vermont, this property boasts two cozy fireplaces, perfect for warming up after a day of winter adventures or enjoying a crisp autumn evening. With two distinct living areas, you'll find the ideal spaces for

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  13 Betty Johnson Ln, Bondville, VT 05340
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  $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
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  $975,000

  • 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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  /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
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  /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
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  $979,000

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

  41-43 Cranberry Hill Rd, Winhall, VT 05340

  PUBLIC OPEN HOUSE Sunday, March 15 2:00-4:00pm. This is the ultimate Alpine chalet, fully renovated as a mountain modern gem but retaining the classic flat-sawn balusters characteristic of mountain homes in the Alps. Nestled in the coveted community of Strattonwald, this home offers Stratton shuttle access right from the driveway. The cherished private community area offers multi-season fun with

  Jamie Luke TPW Real Estate

  41-43 Cranberry Hill Rd, Winhall, VT 05340
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  $2,850,000

  • 4 Beds
  • 6 Baths
  • 5,082 Sq Ft

  41 Stark Farm Rd, Winhall, VT 05340

  41 Stark Farm is your next stop to happiness and joy. This one-of-a-kind property pairs a beautiful country farmhouse with an incredible party barn built for entertaining. Minutes from Stratton and Bromley to mention just a few major ski mountains and within a 15 minute drive of Manchester you cannot beat this location. On 7.8 landscaped acres with your own private pond large enough to host a

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  41 Stark Farm Rd, Winhall, VT 05340
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  $395,000

  • Land
  • 6.93 Acres
  • $56,999 per Acre

  lot#2 Margeaux Ln, Stratton, VT 05155

  This stunning 6.93-acre parcel offers the perfect setting to build the home of your dreams, just moments from the Sun Bowl at Stratton. Nestled in a serene wooded landscape, the property provides both privacy and tranquility while being ideally located for easy access to all that Stratton has to offer. With a septic permit already approved for a 4-bedroom home, this lot is ready for you to begin

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  lot#2 Margeaux Ln, Stratton, VT 05155
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  /14

  $649,000

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft

  792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155

  Maximize your time on the snow in this coveted two-bedroom village watch condo. Featuring a spacious, open layout, the interior boasts a classic wood-burning fireplace and a full kitchen perfect for entertaining. Forget the shuttle; enjoy the seamless convenience of a private ski locker and immediate access to both the lifts and the vibrant resort village. A perfect blend of convenience,

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155
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  $475,000

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

  7 Stratton West Rd Unit 7, Winhall, VT 05340

  This recently renovated 4/5 bedroom Stratton West home is located minutes to Stratton Resort for skiing, golf, and all your recreation activities. The new, custom-built kitchen offers an open layout with beautiful granite countertops. Front and back decks provides places to grill and relax on warm summer nights, or you can cozy up with the Harman pellet stove in the winter months. The first level

  Mike England Michael England Real Estate

  7 Stratton West Rd Unit 7, Winhall, VT 05340
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  $1,100,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 4.5 Baths
  • 4,279 Sq Ft

  3 Linscott Rd, Winhall, VT 05340

  Welcome to this exceptional Stratton contemporary, perfectly positioned just minutes from the Stratton base lodge while nestled in a quiet and private neighborhood setting. Meticulously maintained and thoughtfully updated, this home offers the ideal blend of comfort, sophistication, and mountain lifestyle living. Designed for both relaxation and entertaining, the open-concept floor plan creates a

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  3 Linscott Rd, Winhall, VT 05340
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  $775,000

  • 4 Beds
  • 3 Baths
  • 2,317 Sq Ft

  0 Maple Ridge Rd Unit B-2, Winhall, VT 05340

  Beautifully updated Piper Ridge townhouse just steps from the private sports center and offering weekend/holiday shuttle service to Stratton’s lifts in winter. This light-filled home features an updated kitchen and baths, gleaming hardwood floors, and elegant tilework throughout. The one-car garage has been thoughtfully converted into a spacious ski room plus a large storage or owner’s

  Carrie Mathews Winhall Real Estate

  0 Maple Ridge Rd Unit B-2, Winhall, VT 05340
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  $1,325,000

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

  11 Roundtree Rd, Bondville, VT 05340

  A landmark on Round Tree Road, this house has inviting curb appeal with its stone façade and archway. On the resort shuttle bus route. 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. Downstairs family room with kitchenette. Great living space and bedrooms throughout. Quality metal

  Andrew King Stratton Real Estate

  11 Roundtree Rd, Bondville, VT 05340
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  /24

  $849,000

  • 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 – Walk to LiftDiscover the ideal ski retreat in this bright, spacious, one-of-a-kind double unit at Ober Tal, Building C. Just a short walk 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

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

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

Showing Results 41 - 72, Page 2 of 2