South Londonderry, VT Homes for Sale with Garage

/38
$495,000

$20K PRICE DROP
- 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

Alison Cummings

Cummings & Co

367 Stratton Gate Rd, Jamaica, VT 05343
/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
/55
$495,000

$60K PRICE DROP
- 2 Beds
- 1 Bath
- 1,344 Sq Ft
935 Old Manchester Rd, Peru, VT 05152

Two Bedroom One bath home on 10 Private Acres Peace, Privacy & Ski AccessEscape to your own woodland retreat nestled on 10 serene acres of open meadow and forest. Just moments to Bromley, Stratton & Magic Ski Mountain, this property offers the perfect mix of off-grid living and outdoor adventure. OFF GRID!Fully self-sufficient with solar power and propane generator backup, the home

Margretta Fischer

Wohler Realty Group

935 Old Manchester Rd, Peru, VT 05152
/16
$1,050,000
- 4 Beds
- 3.5 Baths
- 2,256 Sq Ft
16 Middle Ridge Rd Unit 22, Winhall, VT 05155

Unique four bedroom three and one half bath townhome, located directly across the street from the Stratton Village and ski area. Built in 1988, Fox Chapel is the second phase of the Village Chalet neighborhood. Only 27 of these properties exist. Although connected by a breezeway to the property next to it, feels very much like a stand alone home. Walking distance to shops, restaurants and all ski

John Sikes Stratton Real Estate

16 Middle Ridge Rd Unit 22, Winhall, VT 05155
/58
$2,399,000

New Construction $26K PRICE DROP
- 4 Beds
- 3.5 Baths
- 4,536 Sq Ft
33 Stone Lodge Rd, Winhall, VT 05340

Experience Premiere Luxury living in this newly built mountain residence with extraordinary panoramic views . Just minutes to Stratton Mountain'sTrails and move in ready, no detail has been overlooked with superior craftsmanship, energy efficiency and contemporary design. The handcrafted Timber Frame great room , defined by cathedral ceilings, wood burning stone hearth and expansive windows,

Kim Morgan-Wohler Wohler Realty Group

33 Stone Lodge Rd, Winhall, VT 05340
/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
/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
/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
/60
$1,650,000
- 3 Beds
- 4 Baths
- 5,072 Sq Ft
36 Beaver St, Bondville, VT 05340

Your Ultimate Vermont Mountain Retreat Awaits! Luxury log home plus a 2,250 sqft guest house! 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,

MaryKate Grey Stratton Real Estate

36 Beaver St, Bondville, VT 05340
/54
$1,895,000

$95K PRICE DROP
- 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

Jamie Wylie Stratton Real Estate

27 Mountain View Rd, Winhall, VT 05360
/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
/57
$2,500,000

New Construction $450K PRICE DROP
- 4 Beds
- 4.5 Baths
- 3,762 Sq Ft
59 Garden Loop Rd, Winhall, VT 05340

LABOR DAY WEEKEND BEGINS WITH A HUGE PRICE CHANGE! - 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

Terry Hill Berkshire Hathaway HomeServices Stratton Home

59 Garden Loop Rd, Winhall, VT 05340
/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
/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
/37
$600,000

$130K 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
$825,000

$25K PRICE DROP
- 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
/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
/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
/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
/26
$825,000

$25K PRICE DROP
- 3 Beds
- 3 Baths
- 2,598 Sq Ft
C-4 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

C-4 Ridge Rd Unit C-4, Winhall, VT 05340
/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
/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
/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
/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
/59
$1,100,000

$100K PRICE DROP
- 4 Beds
- 3 Baths
- 4,193 Sq Ft
70 Hunter Ln, Jamaica, VT 05343

Discover a truly unique four season home. In the summer, kayak and swim on a private pond. In the fall, hike the many trails that are available and enjoy the foliage. When the Winter comes, it's a ten minute trip to Stratton Mountain and afterwards, ice skate on your own back yard pond. In the spring, step outside to a private hot tub inviting you to to soak while overlooking the sprawling

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

70 Hunter Ln, Jamaica, VT 05343
/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
$1,500,000
- 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
/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
/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
/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
/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
/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
/41
$910,000

$40K PRICE DROP
- 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
/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
/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
/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
/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
/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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