Homes for Sale in 05155

/60
$2,700,000
- 4 Beds
- 3.5 Baths
- 3,938 Sq Ft
23 Valley View Rd, Winhall, VT 05340

Where Eagles Soar! This unsurpassed, top of the mountain panorama stretches for over 40 miles! Located comfortably between Stratton and Manchester on 28 acres perfecting privacy as it's gently rising paved approach sets the tone for this 4000 SF luxury retreat that shall call one back to Vermont over and over again! Memories are made here as this property proves ideal for entertaining or personal

Laura Beckwith Josiah Allen Real Estate, Inc.

23 Valley View Rd, Winhall, VT 05340
/18
$295,000
- 4 Beds
- 2 Baths
- 1,024 Sq Ft
3380 Under the Mountain Rd, Londonderry, VT 05155

Amazing opportunity to own 60 acres on desirable Under The Mountain Road. This location is perfect for nature and adventure lovers alike, with several ski areas nearby. Ski at Bromley, Magic, Stratton, or take advantage of the many hiking and biking trails. There is a barn on the property with a residence on the second floor offering 4 bedrooms with 2 bathrooms. Options to live in the barn/house

Rebecca Seymour Brattleboro Area Realty

3380 Under the Mountain Rd, Londonderry, VT 05155
/15
$415,000
- 1 Bed
- 1 Bath
- 560 Sq Ft
761 Stratton Mountain Access Rd Unit 333, Stratton, VT 05360

Enjoy the convenience of mountain living from this well-positioned residence in Long Trail House. Overlooking the peaceful Commons Pond, this home offers a relaxing setting while placing you directly across the street from Stratton Village and the ski slopes.The functional floor plan provides comfortable living with easy access to outdoor space, making it simple to enjoy every season. Whether

Jamie Wylie Stratton Real Estate

761 Stratton Mountain Access Rd Unit 333, Stratton, VT 05360
/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
/59
$2,350,000
- 5 Beds
- 3.5 Baths
- 4,752 Sq Ft
6 Sunset Ridge Rd, Winhall, VT 05340

Set within the exclusive High Meadow community, one of Stratton's most prestigious mountain enclaves, 6 Sunset Ridge is an extraordinary resort residence of post and beam architecture & impeccable craftsmanship. Positioned to capture sweeping views of Stratton Mountain, this exceptional residence offers an unparalleled lifestyle in one of Stratton's most sought-after luxury neighborhoods. From

Kim Morgan-Wohler Wohler Realty Group

6 Sunset Ridge Rd, Winhall, VT 05340
/38
$1,250,000
- 4 Beds
- 3 Baths
- 2,022 Sq Ft
564 Goodaleville Rd, Jamaica, VT 05343

OPEN HOUSE SATURDAY 8/1 FROM 3PM-5PM | 10 MINUTES TO STRATTON RESORT | 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.

Cheyanne Pugliese

564 Goodaleville Rd, Jamaica, VT 05343
/47
$1,450,000
- 5 Beds
- 4 Baths
- 2,974 Sq Ft
494-498 Goodaleville Rd, Jamaica, VT 05343

OPEN HOUSE SATURDAY 8/1 FROM 3PM-5PM |10 MINUTES TO STRATTON RESORT | 4BR main house, 1BR barn apartment, and separate restored vintage barn | Just minutes from Stratton Mountain Resort, this beautifully restored Vermont farmhouse blends authentic character, exceptional craftsmanship, and modern comfort. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the

Cheyanne Pugliese

494-498 Goodaleville Rd, Jamaica, VT 05343
/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
/18
$235,000

$4K PRICE DROP
- 2 Beds
- 1 Bath
- 1,356 Sq Ft
765 Thompsonburg Rd, South Londonderry, VT 05155

Perfectly positioned in the heart of Vermont's sought-after Golden Triangle, this charming two-bedroom plus loft home offers the ideal balance of year-round recreation and cozy mountain living. Just minutes from Magic Mountain, Bromley Mountain, and Stratton Mountain, you'll enjoy easy access to skiing, hiking, golf, shopping, dining, and all the outdoor adventures Southern Vermont has to

Carrie Mathews Winhall Real Estate

765 Thompsonburg Rd, South 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
/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
/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
/21
$160,000
- Land
- 11.08 Acres
- $14,440 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
/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
/16
$365,000

$25K PRICE DROP
- 4 Beds
- 2 Baths
- 1,536 Sq Ft
120 Green Mountain Trail, Londonderry, VT 05148

Set on 3.9 level acres in a quiet neighborhood just minutes from the village of Londonderry, this four-bedroom, two-bath chalet offers comfortable year-round living or an ideal Vermont getaway. The home features a functional floor plan with four bedrooms, generous living space, and family room Recent improvements include a brand-new roof (2026) and the added peace of mind of a fully operational

Wilkie Bushby TPW Real Estate

120 Green Mountain Trail, Londonderry, VT 05148
/34
$949,000
- 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
$850,000
- 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
/40
$469,000

$20K PRICE DROP
- 4 Beds
- 2 Baths
- 1,560 Sq Ft
494 W River St, Londonderry, VT 05155

This comfortable home is situated in a peaceful and open sunny meadow surrounded by mature trees and 10 acres of Vermont woods offering total privacy. A view of Magic Mountain is a bonus as is the close proximity to shopping and dining. An important feature of the home is the newly added Lochinvar high efficiency propane boiler with on demand hot water installed in November of 2025. The 4

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

494 W River St, Londonderry, VT 05155
/26
$299,000
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
57 Vartland Ridge, Londonderry, VT 05148

Set on 1.1 acres with access to VAST trails, this property offers a blend of recent upgrades, functional space, and future potential. Being sold as-is, the property offers the chance to update and customize while benefiting from several major upgrades already completed. Recent improvements include a new furnace and hot water heater installed in 2022, along with a new propane tank and updated

Jamie Wylie Stratton Real Estate

57 Vartland Ridge, Londonderry, VT 05148
/40
$499,000

$26K PRICE DROP
- 4 Beds
- 4 Baths
- 2,320 Sq Ft
5735 Vt Route 11, Londonderry, VT 05148

What do you get when two pioneers buy a beautiful colonial farmstead with the intention of sticking around quite a while, rehabilitate it for their long-term use, and then find out work will require them to relocate? You get this gorgeously renovated 4-bath-4-bed 1890 construction on over 2.5 lovely acres back on the market! Sellers are motivated due to having already relocated for work!

Zachary Zupan EXP Realty

5735 Vt Route 11, Londonderry, VT 05148
/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
/32
$1,795,000

$180K 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
/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
/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
$125,000
- Land
- 1.77 Acres
- $70,621 per Acre
997 Stratton Arlington Rd, Stratton, VT 05360

STRATTON & MOUNT SNOW - Build your dream ski home on this newly subdivided lot with 103' of road frontage and 1.77 private acres located only 10 minutes from both Stratton Mountain Ski Resort and Mount Snow Ski Resort. All the hard work has been done! Survey, septic design, site plan, state of VT wastewater and well approval, and driveway permit have all been approved and filed with the town.

Derek Greene Derek Greene

997 Stratton Arlington Rd, Stratton, VT 05360
/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
/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
$649,000
- 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 place

Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

792 Stratton Mtn Access Rd Unit 4310, Stratton, VT 05155
/41
$899,000

$301K PRICE DROP
- 4 Beds
- 3 Baths
- 3,252 Sq Ft
E1 Rock Ridge Rd, Winhall, VT 05155

Ideally situated near the renowned Stratton Mountain Resort and offering convenient shuttle service to the slopes, this spacious four-bedroom, three-bath ski condo is thoughtfully designed for year-round enjoyment. A true retreat for outdoor enthusiasts, the home provides effortless access to world-class skiing in the winter and outstanding hiking and mountain biking throughout the warmer months.

Christine Chovan

E1 Rock Ridge Rd, Winhall, VT 05155
/60
$565,000

$10K PRICE DROP
- 3 Beds
- 2 Baths
- 1,944 Sq Ft
3148 Route 11, Londonderry, VT 05148

Looking for useable acreage with so much potential? Looking for a piece of Vermont to call your own? Look no further then this beautiful home, situated on 14 acres, looking for new owners to love and enjoy it like the current owners have. Perfectly situated in Londonderry, Vermont near Bromley, Stratton, Okemo, and Magic Mountains. The sellers have done updates to the home and property but have

Erin Kendall EXP Realty

3148 Route 11, Londonderry, VT 05148
/14
$235,000
- Land
- 33.48 Acres
- $7,019 per Acre
0 Vt Route 100 Unit 5072614, Londonderry, VT 05155

Beautiful 33.48 acre building lot in Londonderry. Some views possible and some clearing has been done. There are some wetlands on property but various choices for building sites exist. South East Facing

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

0 Vt Route 100 Unit 5072614, Londonderry, VT 05155
/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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