Newest Homes for Sale in South Londonderry, VT

/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
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/19
$63,000
- 2 Beds
- 1 Bath
- 672 Sq Ft
2022 Route 30, Jamaica, VT 05343

Looking for an easy escape to the mountains? This furnished 2-bedroom mobile home sits right on the banks of the West River in West River Park—an ideal spot for seasonal living in Southern Vermont. The park has 23 sites and allows homeowners to stay up to 6 months each year, making it a great option for summer adventures or a winter ski base or, a little bit of both!Stratton is just 20

Carrie Mathews Winhall Real Estate

2022 Route 30, Jamaica, VT 05343
/29
$825,000
- 4 Beds
- 3.5 Baths
- 1,993 Sq Ft
18 High Point Dr Unit 501, Stratton, VT 05360

Located just one mile from Stratton’s Base Lodge and Village, this 4-bedroom, 3-bath end-unit Styles Brook townhome offers the perfect combination of convenience, comfort, and year-round mountain living. Spanning three levels, Unit 501 enjoys the added privacy, extra windows, and abundant natural light that come with end-unit ownership. The main level is designed for gathering, featuring

Cheyanne Pugliese

18 High Point Dr Unit 501, Stratton, VT 05360
/31
$649,000
- 3 Beds
- 2.5 Baths
- 1,650 Sq Ft
28 Styles Branch Rd Unit 305, Stratton, VT 05360

Experience the ease of Stratton Mountain living from this inviting three-bedroom Styles Brook condominium, ideally located just moments from the lifts. Hop on the convenient winter shuttle or enjoy a pleasant walk to the base area, with Stratton's Sports Center, fitness facilities, and year-round amenities just a short stroll away.Designed for both comfort and entertaining, the spacious main

Carrie Mathews Winhall Real Estate

28 Styles Branch Rd Unit 305, Stratton, VT 05360
/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
/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
/34
$915,000

$34K PRICE DROP
- 3 Beds
- 3.5 Baths
- 1,800 Sq Ft
56 Shattarack Rd Unit D6, Stratton, VT 05360

Experience ultimate year-round luxury in this tastefully renovated townhome at Slopeside, featuring convenient trail access. Perfectly blending comfort and convenience, this inviting mountain retreat features an updated kitchen and baths, a cozy wood-burning fireplace, and mini-splits for efficient summer cooling. The spacious layout offers three bedrooms plus a private loft complete with its own

Christina Dryden Berkshire Hathaway HomeServices Stratton Home

56 Shattarack Rd Unit D6, Stratton, VT 05360
/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
/18
$535,000
- 2 Beds
- 1 Bath
- 850 Sq Ft
12 Ober Tal Dr Unit C14, Stratton, VT 05360

Opportunity awaits in this trailside condominium at Stratton Mountain Resort. Ideally positioned for convenient access to the Tamarack Chairlift and Stratton Village, this residence offers the mountain lifestyle buyers seek with direct access to skiing, dining, shopping, and year-round resort amenities. Inside, a wood-burning fireplace anchors the living area, creating an inviting space to gather

Timothy Mich Doddridge Stratton Real Estate

12 Ober Tal Dr Unit C14, Stratton, 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
/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
/38
$605,000

$20K PRICE DROP
- 3 Beds
- 2 Baths
- 2,288 Sq Ft
1 Beaver St, Bondville, VT 05340

Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minutes to Bromley, and 12 minutes to Manchester, you’ll enjoy easy access to skiing, dining, shopping, and year-round recreation.Inside, the home features a spacious living room filled with natural light, creating a warm and

Carrie Mathews Winhall Real Estate

1 Beaver St, Bondville, VT 05340
/39
$799,000

$40K PRICE DROP
- 5 Beds
- 4.5 Baths
- 3,840 Sq Ft
42 Blackberry Ln, Jamaica, VT 05343

Only 8 miles from Stratton Mountain, this extra-large expanded farmhouse provides ample space, quiet, and tons of classic Vermont charm. Set in a lush garden landscape surrounded by meadows, a stone wall, perennial gardens, an apple orchard, a barn, & multiple outbuildings, the home feels like old Vermont while being close to major amenities. The original home is from the 19th century but

Cheyanne Pugliese

42 Blackberry Ln, Jamaica, VT 05343
/9
$374,900
- Land
- 2.31 Acres
- $162,294 per Acre
0 Wall St, Winhall, VT 05340

Offered as a set, this property presents a rare opportunity to own two separately deeded parcels in a location that is only minutes from Stratton Mountain yet worlds away from the bustle of the resort. Totaling 2.31 acres, this land is situated high on River Road where neighboring homes enjoy spectacular views of Stratton. Conceptual rendering showing the potential view is based on the current

Cheyanne Pugliese

0 Wall St, Winhall, VT 05340
/16
$875,000
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
447 Rock Bottom Ln, Peru, VT 05152

Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the

Andy Reed Four Seasons Sotheby's Int'l Realty

447 Rock Bottom Ln, Peru, VT 05152
/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
/37
$1,295,000

$20K PRICE INCREASE
- 5 Beds
- 3.5 Baths
- 3,040 Sq Ft
4427 W Hill Rd S, Jamaica, VT 05343

A true Vermont lodge in every sense—warm, welcoming, beautifully appointed, and designed to bring people together. This exceptional mountain retreat combines the character and comfort buyers dream about in a Vermont home with the space, amenities, and proven rental history that make it equally appealing as an investment. The property has enjoyed a strong rental history with repeat guests who

Carrie Mathews Winhall Real Estate

4427 W Hill Rd S, 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
/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
/22
$595,000
- 4 Beds
- 2 Baths
- 1,430 Sq Ft
9 Mountain Acres Rd, Jamaica, VT 05343

Completely renovated and move-in ready, this stunning mountain home offers the perfect blend of comfort and convenience. The full interior renovation includes a brand-new kitchen and bathroom (as well as an updated second bath) , updated bedrooms, new doors, fresh paint, and beautiful new flooring throughout. A propane fireplace adds warmth and charm, while a newly installed mini-split system

Carrie Mathews Winhall Real Estate

9 Mountain Acres Rd, Jamaica, VT 05343
/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
/50
$1,800,000
- 4 Beds
- 5 Baths
- 4,853 Sq Ft
95 Middletown Rd, South Londonderry, VT 05155

One-of-a-Kind Vermont Lifestyle PropertyHome, Income & Creative Opportunity Welcome to an exceptional Southern Vermont offering that blends refined country living with rare income and lifestyle flexibility. Set on 2.4 picturesque acres in South Londonderry, this beautifully restored 1865 property is first and foremost a warm and inviting 4-bedroom home—rich in character, thoughtfully updated,

Eric Nathan Nathan Auction & Real Estate Inc.

95 Middletown Rd, South Londonderry, VT 05155
/60
$1,160,000
- 5 Beds
- 4 Baths
- 3,664 Sq Ft
82 N Brookwood Rd, Stratton, VT 05360

Location , Location , Location! Situated on North Brookwood just below the covered brige you'll enjoy easy access to the Wanderer ski trail as well as the resort shuttle that picks you up at your driveway! This iconic resort property features a great room with custom wood barrel cathedral ceilings, a wall of glass, wood burning fireplace and wrap around deck. Designed for the mountain enthusiast,

Kim Morgan-Wohler Wohler Realty Group

82 N Brookwood Rd, Stratton, VT 05360
/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
/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
/9
$195,000
- Land
- 1.2 Acres
- $162,500 per Acre
4769 Pikes Falls Rd, Jamaica, VT 05143

This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

Rachel Febbie EXP Realty

4769 Pikes Falls Rd, Jamaica, VT 05143
/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
/30
$429,000

$16K PRICE DROP
- 2 Beds
- 2 Baths
- 1,353 Sq Ft
49 High Point Dr Unit A-14, Stratton, VT 05360

Embrace the ultimate Stratton lifestyle in this turnkey, one-level 2BR/2BA condo designed for effortless mountain access. Located just moments from the Village and the Stratton training center, this home eliminates the logistics and maximizes the fun with a dedicated gear-ready mudroom and a complimentary shuttle that whisks you straight to the lifts. The interior features a bright, open-concept

Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

49 High Point Dr Unit A-14, Stratton, VT 05360
/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
/17
$729,000
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
778 Stratton Mountain Access Rd Unit 2103, Stratton, VT 05155

Ski-In/Ski-Out Perfection: Your Premier Stratton Mountain Retreat! Experience the ultimate Vermont lifestyle in this rare 2-bedroom, 2-bathroom condo, perfectly positioned for true ski-in/ski-out convenience. Located just steps from the Villager Chairlift and the bustling heart of Stratton Village, this residence offers a seamless transition from the slopes to your front door.Designed with

Robin Apps Four Seasons Sotheby's Int'l Realty

778 Stratton Mountain Access Rd Unit 2103, Stratton, VT 05155
/14
$629,000

$20K PRICE DROP
- 2 Beds
- 2 Baths
- 1,148 Sq Ft
792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155

Imagine Friday evening: you pull through the private gate, the tires of your car crunching over the paved lot, and you find that perfect spot right near the entrance. As you turn off the engine, a quiet stillness settles in. You won’t be reaching for those keys again until Monday.Welcome to your retreat at Village Watch.The ArrivalStep inside the dedicated mudroom, where there’s a

Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155
/13
$120,000
- Land
- 4.68 Acres
- $25,641 per Acre
8559 Vt Route 30, Jamaica, VT 05343

Double the Lots, Half the Drama.Why buy one lot when you can have two for the price of... well, this one? Here are 4.68 acres of "ready-to-go" land. Permits are secured for a 3 bedroom house on each lot, and the septic is already there, so you don't have to spend your weekends at town hall meetings. Build on both, or build on one and sell the other to that friend who always "forgets" their

TG Glazer Winhall Real Estate

8559 Vt Route 30, Jamaica, VT 05343
/9
$65,000

$10K PRICE INCREASE
- Land
- 1 Acre
- $65,000 per Acre
000F-320 Bourbon Run Rd, Jamaica, VT 05343

This 1-acre wooded lot in Jamaica permitted for a 3 bedroom , 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

Mike England Michael England Real Estate

000F-320 Bourbon Run Rd, Jamaica, VT 05343
/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
/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
/14
$450,000

$50K PRICE DROP
- Land
- 21.2 Acres
- $21,226 per Acre
56 Lower Taylor Hill Rd, Winhall, VT 05340

Set along Lower Taylor Hill Road in Winhall, this 21.2 +/- acre offering captures the privacy, natural beauty, and four-season lifestyle that define Southern Vermont living. Rolling terrain, mature woodland, and natural clearings create an exceptional setting for a private Vermont retreat, with the potential for Bromley Mountain views depending on house placement and design.Supported by a

Kevin Moran Four Seasons Sotheby's Int'l Realty

56 Lower Taylor Hill Rd, Winhall, VT 05340
/38
$375,000
- Land
- 1.23 Acres
- $304,878 per Acre
0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340

Exceptional offering. This premier parcel defines phase II of Ravenwood, an enclave of distinctive and premier mountain residences. This notable site offers extraordinary mountain views, direct access from Winhall Hollow Road and still enjoys all the benefits and amenities of The Ravenwood Neighborhood Association. Combining, privacy, natural beauty and convenience, this well-established

Kim Morgan-Wohler Wohler Realty Group

0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
/12
$450,000
- Land
- 10.26 Acres
- $43,860 per Acre
4.1 Pearl Buck Dr, Winhall, VT 05340

One of the last significant VIEW lots available on the mountain , with unrivaled 360 degree views, including dead on views of Stratton Mountain trails. The pinnacle of this 10.26 acre lot is deserving of an exceptionally designed and expansive home in this premium location with commanding views.Prime for a legacy property in a most desirable location, just 5 minutes to the Stratton Base Area,

Kim Morgan-Wohler Wohler Realty Group

4.1 Pearl Buck Dr, Winhall, VT 05340
/12
$150,000

$25K PRICE DROP
- Land
- 2.26 Acres
- $66,372 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-Private Shuttle Bus service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water Permit in place for approved

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

0 Stratton Gardens Rd Unit 5072896, 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

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