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Windham, VT Houses for Sale

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  • /60

    $499,000

    • 3 Beds
    • 2 Baths
    • 2,416 Sq Ft

    756 Birch Hill Rd, West Townshend, VT 05359

    Tucked into the peaceful woods of Windham, Vermont, this cherished Timber Ridge residence offers a rare opportunity to own a piece of true Vermont legacy. Custom built and lovingly held by the same family across three generations, this home is filled with decades of storied memories, seasonal celebrations, and effortless mountain living.Set on a picturesque one acre wooded parcel, the home’s

    Agent Photo

    Alison Cummings

    Cummings & Co

    756 Birch Hill Rd, West Townshend, VT 05359
  • /31

    $253,000

    $6K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    51 Golding Rd, Windham, VT 05359

    This tidy log home is located 30 minutes or less from 5 ski areas! From Windham there are many directions to choose with activities like hiking and biking right out the door and restaurants, shops and recreation within a short drive. On a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in the

    Agent Photo

    Alison Cummings

    Cummings & Co

    51 Golding Rd, Windham, VT 05359
  • /51

    $799,000

    • 4 Beds
    • 5 Baths
    • 3,992 Sq Ft

    1035 Vermont 121, Windham, VT 05359

    Set on 17 private acres off Route 121, this Windham property delivers the space, flexibility, and access buyers are looking for in Southern Vermont. The open-concept main level is anchored by a grand living room with cathedral ceilings, hardwood floors, and a gas fireplace, flowing easily into a generous dining area designed to host large gatherings and a well-equipped kitchen with coffee bar. A

    Jamie Wylie Stratton Real Estate

    1035 Vermont 121, Windham, VT 05359
  • /60

    $549,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 850 Sq Ft

    794 White Rd, Windham, VT 05359

    Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

    Erica Reynolds Southern Vermont Realty Group

    794 White Rd, Windham, VT 05359
  • /31

    $375,000

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 3,502 Sq Ft

    715 Chase Rd, West Townshend, VT 05359

    In the heat of it all!! With 4 mountains within in about 1/2 hour, this is the perfect spot to get away for skiing and all the other Southern Vermont treasures. Nestled in a sweet meadow, with a wee bit of forest, this home is a perfect home base with plenty of room for everyone. With a lovely flat yard, huge private back deck and large above the ground pool, there are lots of options for

    Christine Lewis Brattleboro Area Realty

    715 Chase Rd, West Townshend, VT 05359
  • /51

    $569,000

    • 6 Beds
    • 5 Baths
    • 4,942 Sq Ft

    1113 Old Cheney Rd, West Townshend, VT 05359

    Set on a scenic country property in Windham, this expansive home offers exceptional space, flexibility and a setting with real character. Currently used as a large single-family residence, the home was originally built as a three-family property, with a common entrance serving two living areas and a separate entrance to the garden-level apartment. A central stairwell can connect the spaces,

    Daire Gibney Barrett and Valley Associates Inc.

    1113 Old Cheney Rd, West Townshend, VT 05359
  • /33

    $499,000

    • 2 Beds
    • 2 Baths
    • 3,320 Sq Ft

    5855 Windham Hill Rd, West Townshend, VT 05359

    Bring your vision to life on 33.34 acres in the scenic hills of Windham, Vermont. This partially completed home offers a rare opportunity to finish a thoughtfully designed residence surrounded by open meadows, established trails, and an idyllic rural setting.Designed with a 4 bedroom septic system, the home is ready for the next owner to complete the interior and exterior finishes. The

    Keith Nowak Four Seasons Sotheby's Int'l Realty

    5855 Windham Hill Rd, West Townshend, VT 05359
  • /33

    $695,000

    • 3 Beds
    • 2.5 Baths
    • 2,232 Sq Ft

    717 Horsenail Hill Rd, Windham, VT 05359

    Brand-new construction in beautiful Windham, Vermont! This thoughtfully designed three-bedroom home with an additional bonus room offers the comfort, efficiency, and ease of new construction paired with a peaceful Vermont setting. Filled with natural light, the home features bright, welcoming living spaces and a versatile floor plan designed for both everyday living and weekend escapes. The bonus

    Carrie Mathews Winhall Real Estate

    717 Horsenail Hill Rd, Windham, VT 05359
  • /42

    $795,000

    • 4 Beds
    • 2.5 Baths
    • 2,544 Sq Ft

    6694 Route 11, Londonderry, VT 05148

    Pride of ownership is evident throughout this exceptionally well cared for four-bedroom home, beautifully situated on more than four acres in desirable Londonderry. A long, welcoming driveway and a stately row of mature pines create a wonderful sense of arrival while providing year-round privacy. Offering an ideal blend of comfort, seclusion, and convenience, this inviting property is equally

    Carrie Mathews Winhall Real Estate

    6694 Route 11, Londonderry, VT 05148

Why Live in Windham

Windham, Vermont, is a small, scenic town nestled in the Green Mountains with a population of just over 400 residents. Established in 1795, Windham features the Windham Village Historic District, which includes Greek Revival buildings such as the Congregational Church, all listed on the National Register of Historic Places. The town's secluded environment offers hidden hiking trails and backyard tributaries, with residences often tucked away from the main road. Attractions in Windham include Hamilton Falls, a three-level waterfall with Class-A water, Lowell State Park with a 3.5-mile hiking trail around Lowell Lake, and Mollie Beattie State Forest, popular for summer hikes and winter snowshoeing. The Congregational Church serves as a community hub, hosting events like tag sales, chicken dinners, and yoga classes. Housing options range from quaint cottage camp homes to spacious Farmhouse Revivals, with rustic log cabins and New England colonial-style homes also available. Windham's proximity to five ski resorts makes it a desirable location for winter sports enthusiasts. For dining and shopping, residents often travel to nearby towns such as Londonderry and Grafton. Students attend Townshend School, which has a high rating, before advancing to Leland & Gray Middle and High School. Artistic retreats are supported by the Fourth Corner Foundation, which offers lodging and gallery space for artists. Windham Hill Road connects the town to Vermont Route 11 and Vermont Route 30, facilitating commutes to Albany, Hartford, and Boston.

Single Family Home Price Trends

Median Home Price
$475,000
Median 3-Bedroom Home Price
$432,500
Median 4-Bedroom Home Price
$799,000
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