4,412

Windham, VT Homes

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  • /35

    $359,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    33 Aspen Ln, Bondville, VT 05340

    Minutes from Stratton Mountain, this cozy chalet offers the perfect mountain escape with timeless character and room to make it your own. Featuring a classic chalet style floor to ceiling stone fireplace and wood interior, this home exudes vintage alpine charm. There are three bedrooms, two baths and an open concept living space, providing plenty of room for gatherings or weekend getaways.

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 424-9210

    33 Aspen Ln, Bondville, VT 05340
  • /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
  • /27

    $1,300,000 Sold Jul 31, 2025

    • Land
    • 591 Acres
    • $2,200 per Acre
    • 136 Days On Market

    0 W Hill Rd S Unit 5006431, Jamaica, VT 05343

    Welcome to an exceptional opportunity in Jamaica, VT! College Hill, a 591-acre parcel, owned by the same family for 70 years, is a rare find in today's market. Unencumbered by permits or land use restrictions, this property offers limitless possibilities. The current owners have maintained its natural beauty, never logging the land, preserving its pristine condition. At the top of College Hill,

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    0 W Hill Rd S Unit 5006431, Jamaica, VT 05343
    • /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
  • /41

    $8,950,000

    • 6 Beds
    • 10 Baths
    • 13,393 Sq Ft

    370 Fischer Ln, Jamaica, VT 05343

    Accessible, but miles from the everyday. Camp Endo’s mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark

    Dia Jenks LandVest, Inc/Woodstock

    370 Fischer 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
  • /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
    • /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
  • /15

    $775,000

    • Land
    • 52 Acres
    • $14,924 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /35

    $9,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,908 Sq Ft
    • House for Rent

    43 Cranberry Hill Rd, Winhall, VT 05340

    First time available for a seasonal rental.Call 43 Strattonwald home for your 25-26 ski season. This recently updated modern, yet classic chalet has room for all. With four bedrooms, two of the primary bedrooms with en-suite bathrooms, there is ample room for everyone's comfort. The home has brand new bathrooms, modern decor and state of the art appliances. With several living areas

    Peggy O'neill Cummings & Co

    43 Cranberry Hill Rd, Winhall, VT 05340
  • /28

    $770,000 Sold Jul 18, 2025

    • 3,556 Sq Ft
    • $217/SF
    • 113 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1980

    5 Stratton Ridge Rd, Winhall, VT 05340

    Discover the ultimate Vermont ski retreat, just 2 miles from Stratton Mountain. This captivating home offers breathtaking mountain views across three spacious levels. The upper level features a private primary suite with a newly renovated bath and a cozy loft/office space — your peaceful sanctuary. The heart of the home, the main level, is perfect for gathering, with soaring cathedral ceilings,

    Carrie Mathews Winhall Real Estate

    5 Stratton Ridge Rd, Winhall, VT 05340
    • /31

      Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 1,888 Sq Ft

      12 Stratton Rd W Unit 12, Winhall, VT 05340

      12 Stratton Rd W Unit 12, Winhall, VT 05340
  • /11

    $595,000

    • Land
    • 69 Acres
    • $8,637 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /26

    $30,000 per month

    • 4 Beds
    • 3.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    197 Monadnock View Ln, Jamaica, VT 05343

    Perfect private location only minutes to Ski resorts.Home could accommodate two families comfortably. Hot Tub, fireplace, towels and linens. Sleeping space for up to 10. Close to shopping and to Interstate 91. Beautiful home to spend the winter season at!

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    197 Monadnock View Ln, Jamaica, VT 05343
  • /22

    $265,500 Sold Jul 15, 2025

    • 1,332 Sq Ft
    • $199/SF
    • 72 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1970

    18 Stratton Ridge Rd, Winhall, VT 05340

    Welcome to 18 Stratton West Road – a charming 3-bedroom, 2-bath ski condo located just minutes from Stratton Mountain Resort. This spacious unit features over 1,300 square feet of well-maintained living space, complete with a cozy wood-burning fireplace, updated bathrooms, and generous natural light throughout. The open-concept layout is perfect for entertaining, with a functional kitchen, dining

    Derek Greene Derek Greene

    18 Stratton Ridge Rd, Winhall, VT 05340
    • /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
  • /8

    $320,000

    • Land
    • 35 Acres
    • $9,267 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /48

    $7,000 per month

    • 5 Beds
    • 3.5 Baths
    • 3,858 Sq Ft
    • House for Rent

    20 Jamie Ln, Winhall, VT 05340

    Escape to the tranquility of Vermont with this stunning long-term rental at "Valley View." Nestled in a desirable neighborhood of Winhall, this spacious contemporary home offers unparalleled panoramic views of the surrounding mountains. Imagine waking up to the beauty of the Green Mountains every day in this expansive retreat!This meticulously maintained 5-bedroom, 3.5 bathroom home

    David Powers 42 North LP

    20 Jamie Ln, Winhall, VT 05340
  • /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
    • /28

      Not Listed For Sale

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

      27 Mountain View Rd, Winhall, VT 05360

      27 Mountain View Rd, Winhall, VT 05360
  • /7

    $235,000

    • Land
    • 15 Acres
    • $15,390 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /46

    $5,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,300 Sq Ft
    • House for Rent

    15 Nearing Rd, Winhall, VT 05340

    Imagine waking up to inspiring vistas every day in this remarkable 3 bedroom, 3.5 bath saltbox home. Perched to capture stunning panoramic views of Stratton Mountain's trails, this classic contemporary ski home offers a truly special living experience. The property is settled upon a 1.63-acre knoll and abuts the Winhall Forest, offering peace and privacy.Embrace sustainable living with a

    David Powers 42 North LP

    15 Nearing Rd, Winhall, VT 05340
  • /22

    $360,000 Sold Jun 20, 2025

    • 1,430 Sq Ft
    • $252/SF
    • 112 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1960

    9 Mountain Acres Rd, Jamaica, VT 05343

    This charming ranch-style home, lovingly maintained for years, is ready for its next chapter. Ideally located at the entrance of the sought-after Mountain Acres neighborhood, it offers easy access to local activities while maintaining a peaceful retreat-like feel.Inside, five comfortable bedrooms and two baths provide ample space for family and guests. The open-concept living area, highlighted by

    Helen Nault

    9 Mountain Acres Rd, Jamaica, VT 05343
    • /38

      Est $750,833 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,081 Sq Ft

      80 Pond View Rd, Winhall, VT 05340

      80 Pond View Rd, Winhall, VT 05340
  • /24

    $970,000

    • 4 Beds
    • 3.5 Baths
    • 2,160 Sq Ft

    10 Middle Ridge Rd, Winhall, VT 05155

    Fox Chapel luxury townhome at Stratton. This four bedroom, four bathroom home is offered with the ability to skip the wait list at the Stratton Mountain Club. Renovated bathrooms and air conditioning make this the year round place to be. Prime location next to the ‘Chapel of the Snows’ and the Commons, walk to the Stratton village for ski access, dining, shopping, and resort amenities. Watch the

    Christiane Carroccio TPW Real Estate

    10 Middle Ridge Rd, Winhall, VT 05155
  • /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
    • /31

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,215 Sq Ft

      6 Black Birch Rd, Winhall, VT 05340

      6 Black Birch Rd, Winhall, VT 05340
  • /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
  • /32

    $14,000 per month

    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    14 Burnt Hill Rd, Winhall, VT 05340

    This modern Strattonwald gem is the ultimate plug-and-play Vermont summer house with location, style, convenience and a lake-side lifestyle to remember. Three living spaces -- one on each floor -- allow for plenty of overflow in the morning and afternoon, with two fireplaces ready for friends and family. Four bedrooms plus sleep loft with its own hang-out space lend space for the whole crew!

    Jamie Luke TPW Real Estate

    14 Burnt Hill Rd, Winhall, VT 05340
  • /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
    • /33

      Est $527,096 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,344 Sq Ft

      935 Old Manchester Rd, Peru, VT 05152

      935 Old Manchester Rd, Peru, VT 05152
  • /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
  • /17

    $27,500 per month

    • 3 Beds
    • 2 Baths
    • 1,570 Sq Ft
    • Condo for Rent

    5 Byington Ln, Winhall, VT 05340

    A classic Austrian chalet, this outdoors enthusiasts' home is structured for year-round fun! The living and entertaining space encompasses the main floor: The functional open kitchen/dining room is perfect for the gang before and after weekend adventures, with a spacious great room and stone fireplace. A cozy, irresistible loft awaits upstairs for moments curled up with a book, coffee and a thick

    Jamie Luke TPW Real Estate

    5 Byington Ln, Winhall, VT 05340
  • /29

    $363,825 Sold Jun 06, 2025

    • 1,215 Sq Ft
    • $299/SF
    • 19 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1968

    30 Birch Hill Rd Unit 8 Rock Maple, Winhall, VT 05340

    Discover the ease of Mountain living with the complimentary Birch Hill Shuttle, providing seamless access to winter adventures. This bright and welcoming end-unit townhouse offers plenty of space for family and friends to gather and unwind. With two inviting living areas, three comfortable bedrooms, and two well-appointed bathrooms, there's room for everyone to relax. The spacious entryway is

    Christine Chovan

    30 Birch Hill Rd Unit 8 Rock Maple, Winhall, VT 05340
    • /35

      Est $613,960 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,577 Sq Ft

      10 Pond View Rd, Winhall, VT 05340

      10 Pond View Rd, Winhall, VT 05340
  • /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
  • /29

    $30,000 per month

    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft
    • Townhouse for Rent

    90 Turkey Run Rd, Winhall, VT 05340

    Intervale Rental. Available for the winter 25-26 winter season. Also available for summer or fall monthly rental. Entry mud room for boot storage. Main floor has wood burning fire place, and the deck off the living room is a overlooks the pond. Main floor has primary suite. Two bedrooms plus a sleeping loft on the upper floor. One bedroom has an en suite bathroom, and a hallway full bathroom

    Christiane Carroccio TPW Real Estate

    90 Turkey Run Rd, Winhall, VT 05340
  • /30

    $510,000 Sold Jun 05, 2025

    • 1,459 Sq Ft
    • $350/SF
    • 170 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1977

    5600 Pikes Falls Rd, Jamaica, VT 05343

    Don't miss this amazing opportunity to own a cozy log cabin nestled in the woods off Pikes Falls road with close proximity to Stratton Mountain Resort. This home has been thoughtfully built, well maintained and loved for many years and is now awaiting its new owners. The property features 15 acres, a wood shed and a 19th century Pikes Falls School House, which can be used for extra storage or

    Jamie Wylie Stratton Real Estate

    5600 Pikes Falls Rd, Jamaica, VT 05343
    • /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

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