2,654

Windham, VT Homes in ZIP Code 05155

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  • /33

    $995,000

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft

    19 Village Lodge Rd Unit 407, Stratton, VT 05155

    Rare opportunity to own in the heart of the Stratton Mountain Village! Come home to the Landmark community. Located attached to the iconic "Clocktower" at Stratton, Vermont. This homes boasts three spacious bedrooms and two full bathrooms with amazing mountain views and southern exposure. Enjoy the cozy gas burning fireplace after a hard day skiing or riding. Landmark provides ski lockers, an

    Timothy Mich Doddridge Stratton Real Estate

    19 Village Lodge Rd Unit 407, Stratton, VT 05155
  • /18

    $25,000 per month

    • 3 Beds
    • 2 Baths
    • 1,423 Sq Ft
    • House for Rent

    378 Tuttle Hill Rd, Londonderry, VT 05155

    Welcome to your turn-key home for the '25-'26 ski season! Fully renovated with attention to detail, this cheerful, sunny Scandinavian Modern space welcomes and inspires. 15 minutes to Stratton Base, 14 minutes to Bromley Village, and 10 minutes to Magic Mountain, you are in the middle of it all, with your choice to either explore or stick to your home mountain. The main floor includes a

    Jamie Luke TPW Real Estate

    378 Tuttle Hill Rd, Londonderry, VT 05155
  • /41

    $1,150,000 Sold Jul 25, 2025

    • 2,593 Sq Ft
    • $444/SF
    • 369 Days On Market
    • 4 Beds
    • 5.5 Baths
    • Built 1997

    35 Old Ridge Rd, Winhall, VT 05155

    Located in Stratton High Meadow, this four-bedroom six-bathroom home has everything you need and has a winter shuttle up to Stratton base area for skiing and snowboarding. Walking into the home, there is a large mudroom with bench and plenty of room to get gear organized and ready for the day on the mountain. The two-bay garage is off the right. Continuing, the living and dining areas have

    Mike England Michael England Real Estate

    35 Old Ridge Rd, Winhall, VT 05155
    • /20

      Est $656,822 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,036 Sq Ft

      78 Middle Ridge Rd Unit 102, Stratton, VT 05155

      78 Middle Ridge Rd Unit 102, Stratton, VT 05155
  • /38

    $1,499,999

    • 3 Beds
    • 3.5 Baths
    • 3,300 Sq Ft

    111 Hughes Ln, Jamaica, VT 05343

    Fully renovated in 2022, 450 ft of lake front footage on picturesque Cole Pond. Nestled on nearly 2 acres in Jamaica, VT, this stunning singlefamily home at 111 Hughes Lane was built in 1989 and offers a peaceful retreat for its next owners. With 3 bedrooms, 3 bathrooms, and 1 half bathroom, and 4 built-in adult size bunks for comfortable sleeping of 10, Air-conditioned master bedroom and

    Derek Greene Derek Greene

    111 Hughes Ln, Jamaica, VT 05343
  • /19

    $65,000 per month

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    16 Winterberry Heights, Stratton, VT 05360

    Best of the Best. Ski on Ski off. never rented before, pristine clean and original owners. Largest Treetops there is.. 4 bedroom/4 bath, den family room, amazing views, hot tub.. everything you want and need for an amazing winter season. Loads of room for family and guests and entertaining. Enjoy all that Stratton has to offer as well as all the other ski areas close by and Manchester shopping

    Wilkie Bushby TPW Real Estate

    16 Winterberry Heights, Stratton, VT 05360
  • /25

    $345,000 Sold Jun 30, 2025

    • 1,150 Sq Ft
    • $300/SF
    • 82 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1983

    75 E Birch Rd Unit 21, Stratton, VT 05360

    Discover the perfect mountain getaway with this 2-bedroom, 2-bath condo located just moments from all the action at Stratton Mountain. Whether you're hitting the slopes or enjoying the year-round amenities, this condo offers convenience and comfort at every turn.Step inside to a bright and inviting space with a cozy wood-burning fireplace, ideal for relaxing after a day on the trails. The

    Carrie Mathews Winhall Real Estate

    75 E Birch Rd Unit 21, Stratton, VT 05360
    • /30

      Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 2,088 Sq Ft

      30 Styles Branch Rd Unit 309, Stratton, VT 05360

      30 Styles Branch Rd Unit 309, Stratton, VT 05360
  • /59

    $2,800,000 Open Sat 10AM - 1PM

    • 3 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
  • /19

    $3,000 per month

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft
    • Condo for Rent

    47 Crown Point Dr Unit B-13, Stratton, VT 05155

    Need a place to get away this Summer or Fall? Look no further. This well-equipped condo has three bedrooms and three full baths. The main living area is the much-desired open concept style which is wonderful for entertaining. There is a second living room on the lower level which is fantastic for company. This condo has several mini splits which will conquer those humid nights that we get

    Peggy O'neill Cummings & Co

    47 Crown Point Dr Unit B-13, Stratton, VT 05155
  • /26

    $593,500 Sold Jun 17, 2025

    • 1,607 Sq Ft
    • $369/SF
    • 75 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2003

    2513 Thompsonburg Rd Unit 3A, South Londonderry, VT 05155

    Welcome to this well-cared-for, one-owner home in the charming town of Londonderry, VT. Nestled on a private, beautifully landscaped lot, this property offers both tranquility and convenience, with easy access to three major ski areas—perfect for outdoor enthusiasts.This bright and inviting home features an open layout that maximizes natural light throughout. The spacious main floor boasts a cozy

    Carrie Mathews Winhall Real Estate

    2513 Thompsonburg Rd Unit 3A, South Londonderry, VT 05155
    • /19

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,130 Sq Ft

      43 High Point Dr Unit D23, Stratton, VT 05360

      43 High Point Dr Unit D23, Stratton, VT 05360
  • /12

    $995,000

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft

    4 Dogwood Trail, Stratton, VT 05360

    Ski back home to this beautiful three bedroom plus loft, three bath condominium. Located in the Treetop community, just off the Home Run ski trail. Enlarged patio with hot tub, one car detached garage. Very nice private neighborhood. Sold furnished.

    John Sikes Stratton Real Estate

    4 Dogwood Trail, Stratton, VT 05360
  • /54

    $970,000 Sold Jun 17, 2025

    • 2,672 Sq Ft
    • $363/SF
    • 120 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1994

    13 Windtree Rd, Bondville, VT 05340

    OPEN HOUSE SATURDAY , February 22nd-11:00-3:00.Showings begin 2/20Exceptional Stratton Mountain Resort location on Windtree Road in the desirable North Brookwood neighborhood with Shuttle from your driveway to the Base Lodge! Enjoy this wonderful deck house open floor plan with great winter views, vaulted ceilings, 2 wood burning fireplaces and multiple decks. Well designed for apres ski

    Kim Morgan-Wohler Wohler Realty Group

    13 Windtree Rd, Bondville, VT 05340
    • /31

      Est $733,018 Not Listed For Sale

      • 2 Beds
      • 3 Baths
      • 1,375 Sq Ft

      78 Middle Ridge Rd Unit 106, Stratton, VT 05155

      78 Middle Ridge Rd Unit 106, Stratton, VT 05155
  • /30

    $795,000

    • 3 Beds
    • 3 Baths
    • 1,350 Sq Ft

    771 Stratton Mountain Access Rd Unit 456/458, Stratton, VT 05360

    Very unique three bedroom three bathroom in the ever popular Long Trail House community. Originally a studio and two bedroom unit preconstruction, this premiere condominium has been converted into a family retreat. The home was completely renovated a few years back with wood laminate flooring, granite counter tops, new appliances and renovated bathrooms. The studio was turned into a primary suite

    Timothy Mich Doddridge Stratton Real Estate

    771 Stratton Mountain Access Rd Unit 456/458, Stratton, VT 05360
  • /30

    $275,000 Sold Jun 11, 2025

    • 1,350 Sq Ft
    • $204/SF
    • 48 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1962

    5 Snow Drift Ln Unit 6, Londonderry, VT 05155

    Are you looking to add a little Magic to your life? Then, this is the place for you! Located just off the base area of Vermont’s beloved Magic Mountain in Londonderry, this small, welcoming condo development has just 6 units and embodies the spirit of its nearby mountain with a closeknit and friendly community. Walk to the lifts and ski home in the winter months, wander over to the base area for

    Claudia Harris Mary Mitchell Miller Real Estate

    5 Snow Drift Ln Unit 6, Londonderry, VT 05155
    • /40

      Est $951,472 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,536 Sq Ft

      1751 Under the Mountain Rd, South Londonderry, VT 05155

      1751 Under the Mountain Rd, South Londonderry, VT 05155
  • /49

    $1,350,000

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

    732 Under the Mountain Rd, South Londonderry, VT 05155

    Londonderry’s Under the Mountain Road is one of the area’s most beautiful roads, meandering along the edge of Glebe Mountain (home to Magic Mtn) and thousands of acres of conserved land. Here you’ll find “Fairmount”, featuring one of the best panoramic views in southern Vermont overlooking the West River Valley and majestic Green Mountains between Stratton and Bromley. The 1810 farmhouse was

    Claudia Harris Mary Mitchell Miller Real Estate

    732 Under the Mountain Rd, South Londonderry, VT 05155
  • /34

    $690,000 Sold May 30, 2025

    • 1,502 Sq Ft
    • $459/SF
    • 49 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1977

    22 Shattarack Rd Unit A-5, Stratton, VT 05360

    Slopeside A-5 at Stratton Mountain is a 3-level townhouse with direct access to the Tamarack ski lift via a short walk down a maintained trail. This offering features a generous ski room entry with powder room, main level living and dining with wood-burning fireplace and private deck, upper level primary suite, and lower level bunk room, guest bedroom with Queen bed, shared full bathroom, and

    Beth Vickers Vermont Real Estate Company

    22 Shattarack Rd Unit A-5, Stratton, VT 05360
    • /32

      Est $453,849 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 2,838 Sq Ft

      4232 Vt Route 11, Londonderry, VT 05148

      4232 Vt Route 11, Londonderry, VT 05148
  • /42

    $949,000

    • 4 Beds
    • 3 Baths
    • 3,551 Sq Ft

    1247 Cole Pond Rd, Jamaica, VT 05343

    A once-in-a-lifetime opportunity to own a large family home on Vermonts hidden gem! Cole Pond, a spectacular private lake surrounded by mountains and nestled between five ski areas - 5 minutes from Stratton and close to Bromley, Mount Snow, Okemo and Magic. Cole Pond homes rarely come on the market, and this one is one-of-a-kind, with a lake-front lawn, walk-in access to the water (also great

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    1247 Cole Pond Rd, Jamaica, VT 05343
  • /30

    $760,000 Sold May 23, 2025

    • 1,600 Sq Ft
    • $475/SF
    • 282 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1978

    15 Tamarack Rd Unit G-2, Stratton, VT 05360

    Discover the perfect blend of adventure and relaxation in this stunning 3-bedroom, 3-bathroom townhome, located on the slopes of Stratton Mountain Resort. Offering the ultimate in convenience, this property features ski-in/ski-out access, allowing you to hit the slopes in seconds and return home with ease.Inside, you'll find a spacious and inviting living area, complete with a cozy

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    15 Tamarack Rd Unit G-2, Stratton, VT 05360
    • /27

      Est $193,366 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,356 Sq Ft

      765 Thompsonburg Rd, South Londonderry, VT 05155

      765 Thompsonburg Rd, South Londonderry, VT 05155
  • /39

    $2,800,000 Open Sat 1PM - 3PM

    • 8 Beds
    • 8.5 Baths
    • 4,075 Sq Ft

    69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155

    This extraordinary Stratton Mountain Retreat, just minutes to the slopes, offers glorious long range views and a very private setting. This impressive home was masterfully constructed in 2009 and includes a separate barn, 11.55 acres of land, 2 covered porches, a built in barbecue and an outdoor fireplace, hot tub and fire pit.The main level of the home features a Gourmet Kitchen, grand

    Sara Buckley Josiah Allen Real Estate, Inc.

    69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155
  • /39

    $405,000 Sold May 16, 2025

    • 1,215 Sq Ft
    • $333/SF
    • 24 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1968

    5 Red Hickory Rd, Winhall, VT 05340

    The season is not over! Red Hickory 5 at Birch Hill is one of the best values today offered at Stratton. This ready to move into attractively appointed Co-Op townhome is located at the quiet end of popular Birch Hill street with views of the mountain. Three bedrooms, two baths, family room. Winter shuttle service to the base lodge. Brand new in ground pool for your summer enjoyment. This

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    5 Red Hickory Rd, Winhall, VT 05340
    • /4

      Est $335,082 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,600 Sq Ft

      283 Main St, South Londonderry, VT 05155

      283 Main St, South Londonderry, VT 05155
  • /12

    $1,050,000

    • 3 Beds
    • 3 Baths
    • 1,501 Sq Ft

    759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340

    Designed with the mountain enthusiast in mind, and located just a short walk from the Stratton Resort Village and ski slopes, this three bedroom three bath condominium offers quality and convenience. Private parking, pool, hot tub, sauna and shuttle to the slopes.

    John Sikes Stratton Real Estate

    759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340
  • /39

    $2,200,000 Sold May 14, 2025

    • 2,244 Sq Ft
    • $980/SF
    • 10 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1997

    52 Snow Bridge Rd, Stratton, VT 05360

    Exclusive Snowbridge Trailside Retreat — With a premier snowfront location in Stratton’s coveted Snowbridge community, this unit provides true ski-in/ski-out access and walkability to the Stratton Village shops and restaurants. Gear up in the comfort of your home — go from slippers to ski boots, then take the Old Log Trail directly to the Main Base, Gondola, and Ski School. In addition to an

    Cheyanne Pugliese

    52 Snow Bridge Rd, Stratton, VT 05360
    • /38

      Est $548,807 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,856 Sq Ft

      116 Deerwood Hill, South Londonderry, VT 05155

      116 Deerwood Hill, South Londonderry, VT 05155
  • /40

    $1,450,000

    • 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
  • /15

    $159,500 Sold May 14, 2025

    • Land
    • 11 Acres
    • $14,395 per Acre
    • 440 Days On Market

    000 Rose Ln, Londonderry, VT 05148

    MOTIVATED SELLERS!!!! This 11 acre parcel is located just off Cole Pond, and is just a few miles to Stratton Mountain Access Road. One lot sits high in the sky with breathtaking views and all the serenity of nature. A well constructed driveway runs approximately halfway up the property where you will find a partial building site with an incredible view of Bromley Mountain, from there if you

    Rachel Febbie EXP Realty

    000 Rose Ln, Londonderry, VT 05148
    • /35

      Est $556,117 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,436 Sq Ft

      117 Adams Dr, Londonderry, VT 05148

      117 Adams Dr, Londonderry, VT 05148
  • /46

    $1,350,000

    • 4 Beds
    • 4 Baths
    • 4,640 Sq Ft

    33 Forest Haunts Rd, Winhall, VT 05340

    Discover Your Vermont Retreat Nestled amidst 20.8 private acres of tranquil woods, this French country manor offers an exceptional opportunity to own a piece of Vermont paradise. Situated near the serene North Branch Ball Mountain Brook, enjoy the soothing sounds of cascading water and the breathtaking beauty of nature. Property Highlights: Prime Location: Just minutes from Stratton Resort for

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    33 Forest Haunts Rd, Winhall, VT 05340
  • /39

    $1,750,000 Sold May 09, 2025

    • 2,653 Sq Ft
    • $660/SF
    • 87 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1986

    34 Mountain Reach Mews Rd, Stratton, VT 05155

    Incredible opportunity to own a stunning end unit just steps to Stratton Village and the Villager Lift! Walk right out your door and you are next to Stratton's delicious Firetower restaurant! This location cannot be beat. Unit has a young roof and is meticulously maintained. 4 Bedrooms and 4 bathrooms spread out over 4 floors makes for a great ski home that can accommodate sleeping 10-12 with

    Heidi Zizza Four Seasons Sotheby's Int'l Realty

    34 Mountain Reach Mews Rd, Stratton, VT 05155
    • /40

      Est $735,523 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,714 Sq Ft

      929 Middletown Rd, South Londonderry, VT 05155

      929 Middletown Rd, South Londonderry, VT 05155
  • /53

    $795,000 Under Contract

    • 3 Beds
    • 3 Baths
    • 1,842 Sq Ft

    E12 Rock Ridge Rd, Winhall, VT 05155

    Move right in and start enjoying the Vermont lifestyle at Piper Ridge E12 —an impeccably updated, fully furnished 3-bedroom plus den, 3-bath townhome just minutes from Stratton Mountain. Inside this turnkey home, you'll find bright and welcoming spaces designed for comfort and functionality. Every detail has been thoughtfully considered —a brand-new kitchen, stylishly renovated baths, new

    Cheyanne Pugliese

    E12 Rock Ridge Rd, Winhall, VT 05155
  • /16

    $195,000 Sold May 09, 2025

    • Land
    • 22 Acres
    • $8,667 per Acre
    • 152 Days On Market

    5734 Vermont 11, Landgrove, VT 05148

    MAKE YOUR MEMORIES HERE!! The possibilities are endless for turning this diversified property into your heart's desire. Loved, ownedby, gathered upon, and maintained by the same family for generations, and now it's your turn to make it your own haven. This 23.5 acre parcel is just fullof natural beauty, with an abundance of birds and wildlife. Some of the features include a stream-fed pond, 2

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    5734 Vermont 11, Landgrove, VT 05148
    • /21

      Est $676,333 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 5,754 Sq Ft

      3378 Under the Mountain Rd, South Londonderry, VT 05155

      3378 Under the Mountain Rd, South Londonderry, VT 05155
  • /56

    $1,330,500 Under Contract

    • 4 Beds
    • 4.5 Baths
    • 3,692 Sq Ft

    225 W Jamaica Rd, Stratton, VT 05360

    Perfectly situated between Mount Snow and Stratton Resort, and just a short drive to scenic Grout Pond and the National Forest, this Stratton, Vermont retreat offers the ideal balance of privacy, recreation, and comfort. Set on landscaped grounds with a tranquil pond, the main residence features four spacious bedrooms, two of which are en suite and four bathrooms. The open concept great room

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    225 W Jamaica Rd, Stratton, VT 05360

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