29

South Londonderry, VT Homes for Sale with Garage

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  • /38

    $515,000

    • 4 Beds
    • 3 Baths
    • 2,115 Sq Ft

    367 Stratton Gate Rd, Jamaica, VT 05343

    Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer.Designed for gathering and relaxing, the home features two

    Agent Photo

    Alison Cummings

    Cummings & Co

    367 Stratton Gate Rd, Jamaica, VT 05343
  • /40

    $1,100,000

    • 5 Beds
    • 4.5 Baths
    • 4,453 Sq Ft

    6 Old Ridge Rd, Winhall, VT 05340

    Tucked into Stratton Mountain Resort’s sought after High Meadow neighborhood, 6 Old Ridge Road offers the rare combination of substantial square footage, significant recent exterior improvements, and the opportunity to personalize the interior aesthetic to your own taste. Encompassing over 4,600 sq. ft. across three finished levels, this expansive mountain home is designed for gathering,

    Trent Stephens Wohler Realty Group

    6 Old Ridge Rd, Winhall, VT 05340
  • /13

    $2,525,000

    New Construction $100K PRICE INCREASE
    • 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

    $1,650,000

    • 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

    MaryKate Grey Stratton Real Estate

    36 Beaver St, Bondville, VT 05340
  • /50

    $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
  • /32

    $1,850,000

    $125K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,212 Sq Ft

    74 N Brookwood Rd, Stratton, VT 05360

    PRIME LOCATION near the coveted STRATTON MOUNTAIN RESORT. This EXCEPTIONAL four bedroom three bathroom turn-key home is PRIVATELY SITUATED on 1.5 acres and READY TO BE ENJOYED YEAR ROUND. Snowmobile right from the house to access thousands of acres of pristine VAST snowmobile trails for ENDLESS WINTER ADVENTURE. Ski home to the Covered Bridge neighborhood or hop on the resort shuttle, which runs

    Paul Marino WWW.FLATFEEMLS4FREE.COM

    74 N Brookwood Rd, Stratton, VT 05360
  • /59

    $2,800,000

    • 4 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

    ****OPEN HOUSE - SATURDAY JULY 4TH 2 - 4 PM ****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

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    59 Garden Loop Rd, Winhall, VT 05340
  • /37

    $690,000

    $40K PRICE DROP
    • 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
  • /57

    $850,000

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

    4880 Pikes Falls Rd, Jamaica, VT 05343

    Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no

    Mike England Michael England Real Estate

    4880 Pikes Falls Rd, 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
  • /26

    $850,000

    • 3 Beds
    • 3 Baths
    • 2,598 Sq Ft

    46 Ridge Rd Unit C-4, Winhall, VT 05340

    Experience four-season Vermont living in this beautifully appointed end-unit townhome in the highly sought-after Highgate neighborhood at Piper Ridge, one of Stratton Mountain's premier resort communities. Ideally located in Winhall, Vermont, just minutes from Stratton Mountain Resort, this spacious 3-bedroom, 3-bath residence offers exceptional privacy, abundant natural light, The thoughtfully

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    46 Ridge Rd Unit C-4, Winhall, VT 05340
  • /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
  • /36

    $650,000

    • 3 Beds
    • 3.5 Baths
    • 2,678 Sq Ft

    177 Alwin Ln, Jamaica, VT 05343

    Nestled in a peaceful and private mountain setting, this beautifully maintained home offers a seamless blend of comfort, functionality, and timeless Vermont charm. Thoughtfully updated and designed for easy living.The main level features a spacious primary suite with custom built-in cabinetry, a convenient mudroom, and an updated kitchen highlighted by Vermont Verde marble countertops and

    Helen Nault

    177 Alwin Ln, Jamaica, VT 05343
  • /47

    $1,140,000

    $60K PRICE DROP
    • 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
  • /40

    $489,000

    • 4 Beds
    • 2 Baths
    • 1,560 Sq Ft

    494 W River St, Londonderry, VT 05155

    Welcome to 494 West River Street, a classic Vermont retreat nestled on more than 10 picturesque acres along the scenic West River in South Londonderry. Built in 1965, this four-bedroom, two-bath ranch-style home offers a rare opportunity to enjoy the natural beauty, privacy, and year-round recreation that make Southern Vermont such a sought-after destination. Set among mature trees and open

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    494 W River St, Londonderry, VT 05155
  • /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
  • /40

    $1,500,000

    • 7 Beds
    • 7.5 Baths
    • 8,364 Sq Ft

    251 Pratt Bridge Rd, Jamaica, VT 05343

    Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

    TG Glazer Winhall Real Estate

    251 Pratt Bridge Rd, Jamaica, VT 05343
  • /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
  • /53

    $4,500,000

    • 5 Beds
    • 5.5 Baths
    • 5,700 Sq Ft

    24 Sawmill Rd, Stratton, VT 05360

    Experience the ultimate Stratton Mountain lifestyle from this exceptional ski home, perfectly positioned in one of the resort's most coveted locations. Offering the rare advantage of deeded access to Stratton's impeccably groomed ski trail, this extraordinary property places world-class skiing just steps from your front door—an amenity few homes can claim and even fewer can match.Designed for

    Carrie Mathews Winhall Real Estate

    24 Sawmill Rd, Stratton, VT 05360
  • /41

    $1,600,000

    $150K PRICE DROP
    • 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
  • /27

    $609,000

    • 4 Beds
    • 3 Baths
    • 1,650 Sq Ft

    60 Hilltop Rd Unit 60, Winhall, VT 05340

    Turn-key Stratton retreat in one of the area’s most desirable year-round communities. This 4-bedroom, 3-bath Intervale townhome offers the perfect blend of comfort and convenience—just minutes to the slopes with seasonal shuttle service right from the community. The open-concept living area is ideal for gathering after a day on the mountain, while five mini-split systems provide efficient heating

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    60 Hilltop Rd Unit 60, Winhall, VT 05340
  • /49

    $675,000

    • 3 Beds
    • 2 Baths
    • 2,204 Sq Ft

    11 Stratton View Rd, Bondville, VT 05340

    This is not your average chalet. Tucked in the quiet Stratton View neighborhood, just 1 mile from the base of the Stratton Access Road, this 3-bedroom, 2-bath home offers the warmth and character of a classic Vermont chalet with updated systems, thoughtful improvements, and the things you have been looking for but can’t seem to find: two living spaces and a garage — actually, two garages. Offered

    Cheyanne Pugliese

    11 Stratton View Rd, Bondville, VT 05340
  • /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 seamless

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    1189 Cole Pond Rd, Jamaica, VT 05343
  • /33

    $649,000

    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft

    39 Pond View Rd Unit 39, Winhall, VT 05340

    Set in a prime location along Stratton Access Road, this Intervale townhouse offers an easygoing mountain lifestyle with everything you need close at hand—including weekend and holiday winter shuttle service to the base lodge.The 3-bedroom + loft, 3-bath layout provides plenty of space for guests, while the open living area brings everyone together with a seamless flow between the kitchen,

    Carrie Mathews Winhall Real Estate

    39 Pond View Rd Unit 39, Winhall, VT 05340
  • /40

    $720,000

    $15K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,317 Sq Ft

    B2 Maple Ridge Rd, Winhall, VT 05155

    The Highgate Piper Ridge Townhome is ideally located just a short stroll from the exclusive sports center and provides convenient shuttle service to Stratton’s ski lifts during the winter season. This residence is filled with natural light and features a contemporary kitchen and bathrooms, polished hardwood floors, and elegant tile accents throughout. The one-car garage has been ingeniously

    Mike England Michael England Real Estate

    B2 Maple Ridge Rd, Winhall, 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
  • /54

    $1,990,000

    • 6 Beds
    • 6.5 Baths
    • 5,896 Sq Ft

    27 Mountain View Rd, Winhall, VT 05360

    Direct views of Stratton Mountain set the stage for this exceptional post-and-beam residence, offering a rare combination of luxury living, entertaining space, and rental flexibility. Handcrafted timber framing creates warmth and character throughout, while four fireplaces including a gas fireplace in the primary suite enhance the home's mountain atmosphere. Designed for gathering, the lower

    Jamie Wylie Stratton Real Estate

    27 Mountain View Rd, Winhall, VT 05360
  • /47

    $1,225,000

    • 4 Beds
    • 3 Baths
    • 3,357 Sq Ft

    153 High Meadow Rd, Winhall, VT 05340

    Located in Stratton Resort’s sought-after High Meadow community, this beautifully maintained and turnkey home offers the perfect blend of comfort, convenience, and mountain charm. Filled with natural light, the home features four bedrooms and three recently updated full baths, along with hardwood floors, cathedral ceilings, skylights, and a stunning floor-to-ceiling brick fireplace. Recent

    Britt Wohler

    153 High Meadow Rd, Winhall, VT 05340
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