30,350

Windham, VT Homes

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  • /18

    $130,000

    • Land
    • 2.19 Acres
    • $59,361 per Acre

    192 Pingree Park Ln, Londonderry, VT 05148

    Discover this hidden gem in Londonderry. River frontage on pristine Utley Brook with headwaters flowing from the Green Mountain National Forest create a serene setting minutes from downtown. Full time residence or vacation home, you choose! Ready to build. Completely engineered- State and Town permits for a 4 bedroom home in place including septic permits, well and house placement, updated

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 444-8158

    192 Pingree Park Ln, Londonderry, VT 05148
  • /13

    $1,600 per month

    • 3 Beds
    • 1 Bath
    • 1,023 Sq Ft
    • Condo for Rent

    40 Green St Unit 1, Bellows Falls, VT 05101

    40 Green St Unit 1, Bellows Falls, VT 05101
  • /29

    $174,000 Sold Jul 30, 2025

    • 920 Sq Ft
    • $189/SF
    • 32 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1987

    71 Schoolbus Depot Rd, Bellows Falls, VT 05101

    If you want 13.5 acres of private, undeveloped, Vermont land with The Williams River accessible through a 12-minute walk through YOUR woods, 71 Schoolbus Depot Road is the property for you! The only thing separating your property from the river is a set of railroad tracks. This property was purchased in 1987, and at that time the mobile home was placed there along with the garage which has power.

    Heather Gleim CENTURY 21 North East

    71 Schoolbus Depot Rd, Bellows Falls, VT 05101
    • /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
  • /30

    $125,000

    • 1,968 Sq Ft

    10 Taylor St, Town of Rockingham, VT 05101

    INVESTER SPECIAL! This 2-unit property has separate utilities, 2-3 bedroom units on each floor depending on how the layout is set up. Rooms are generously sized, front and side porches for each unit, full basement and attic.This would make a nice generational or family home or a great starter home with rental potential.

    Agent Photo

    Julie Buffum

    Buffum Realty

    (802) 347-9139

    10 Taylor St, Town of Rockingham, VT 05101
  • /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
  • /18

    $335,000 Sold Jul 30, 2025

    • 1,174 Sq Ft
    • $285/SF
    • 36 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1956

    138 Cedar St, Brattleboro, VT 05301

    Welcome to this adorable 3-bedroom, 1-bath ranch-style home nestled in one of Brattleboro's most sought-after neighborhoods! Built in 1956, this lovingly cared for gem perfectly blends classic character with modern comfort. Many recent upgrades including CertainTeed Monogram vinyl siding and trim, freshly painted interior walls and so much more. The kitchen features a sleek Whirlpool glass top

    Claire Renaud Berkley & Veller Greenwood Country

    138 Cedar St, Brattleboro, VT 05301
    • /11

      Est $305,351 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,992 Sq Ft

      48 Loop Rd, Newfane, VT 05345

      48 Loop Rd, Newfane, VT 05345
  • /56

    $350,000

    • 6 Beds
    • 4.5 Baths
    • 3,042 Sq Ft

    2072 N Main St, Londonderry, VT 05148

    Rare Mixed-Use Opportunity in Downtown Londonderry, VT – Live, Work, or Invest! Unlock the full potential of this versatile and beautifully situated property in the heart of Londonderry’s vibrant downtown district. With major West River frontage, expansive lawn space, and prime visibility on North Main Street, this unique listing offers endless possibilities — perfect for residential, commercial,

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 441-6058

    2072 N Main St, Londonderry, VT 05148
  • /12

    $1,180 per month

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Townhouse for Rent

    995 Western Ave Unit 300, Brattleboro, VT 05301

    Kitchen/living room plus one bedroom on 3rd Floor.Walk to farmer’s market. Laundromat just across the street.Apartment is one of four units in quiet building, each with separate entrance.Lawn care and snow plowing provided.Balcony.Shower in bathroom (no bathtub). Large backyard with room to garden.One parking place only.No smoking.Pets

    995 Western Ave Unit 300, Brattleboro, VT 05301
  • /44

    $405,000 Sold Jul 28, 2025

    • 1,066 Sq Ft
    • $380/SF
    • 33 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1998

    156 Sherwood Cir, Brattleboro, VT 05301

    YOU CAN GET THERE FROM HERE! NEW ENGLAND CHARM AND FLEXIBLE SPACES...YOUR LUSH RETREAT AWAITS! A short drive to the cultural and foodie hub of southeastern Vermont, this slice of heaven is where your dreams take root. Follow a scenic road to a vibrant green lot where a terraced rock wall dotted with ferns and hostas signals your arrival. A large covered porch invites you to pull up a chair,

    Fine Homes Group International Keller Williams Realty-Metropolitan

    156 Sherwood Cir, Brattleboro, VT 05301
    • /33

      Est $670,295 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,700 Sq Ft

      40 Kingswood Rd, Dover, VT 05356

      40 Kingswood Rd, Dover, VT 05356
  • /10

    $185,000

    • Land
    • 8 Acres
    • $23,125 per Acre

    4441 Vt Route 30, Jamaica, VT 05343

    Discover the potential of this serene and wooded 8.0± acre parcel, offering a peaceful setting and natural beauty just minutes from the heart of Jamaica Village. Currently being subdivided from a larger tract, the lot features a 5 Bedroom Wastewater Permit pending state approval and a survey in progress to finalize boundaries—laying the foundation for your future plans. An existing electric

    Agent Photo

    Trent Stephens

    Wohler Realty Group

    (802) 808-6056

    4441 Vt Route 30, 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
  • /23

    $356,000 Sold Jul 28, 2025

    • 1,550 Sq Ft
    • $230/SF
    • 38 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1929

    122 Marlboro Ave, Brattleboro, VT 05301

    122 Marlboro Avenue is in a highly sought out, in-town neighborhood known for its peace and quiet, friendly neighbors, and super-convenient location. This solid, 3-4 bedroom, 2 bath home sits attractively on a sunny and level lot and comes with an oversized garage and attached workshop (and potential to add additional living space). This home provides a completely renovated and modernized

    Stephanie Peduzzi-Baker Brattleboro Area Realty

    122 Marlboro Ave, Brattleboro, VT 05301
    • /33

      Est $239,750 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 856 Sq Ft

      849 Mcmillan Rd, Halifax, VT 05342

      849 Mcmillan Rd, Halifax, VT 05342
  • /14

    $120,000

    • Land
    • 2.07 Acres
    • $57,971 per Acre

    191 Pingree Park Ln, Londonderry, VT 05148

    Discover this hidden gem in Londonderry. River frontage on pristine Utley Brook with headwaters flowing from the Green Mountain National Forest create a serene setting minutes from downtown. Full time residence or vacation home, you choose! Ready to build. Completely engineered- State and Town permits for a 4 bedroom home in place including septic permits, well and house placement, updated

    Agent Photo

    Alison Cummings

    Cummings & Co

    (802) 848-6904

    191 Pingree Park Ln, Londonderry, VT 05148
  • /2

    $1,300 per month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    498 Marlboro Rd Unit N35, Brattleboro, VT 05301

    Property Id: 15107811 bed, 1 bath apartment in Brattleboro, VT! This unit features modern amenities like a microwave, oven, and refrigerator. Enjoy off-street parking, on-site laundry, and a beautiful lawn. Pets are welcome! Don't miss out on this gem for $1,300/month. Book your viewing today!

    498 Marlboro Rd Unit N35, Brattleboro, VT 05301
  • /26

    $347,000 Sold Jul 25, 2025

    • 1,435 Sq Ft
    • $242/SF
    • 22 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1890

    157 Pine St, Brattleboro, VT 05301

    Be impressed by this stately in-town Victorian home with an airy and open-concept feel, handsome historical features, and many thoughtful and attractive upgrades. Enter this lovely home loaded with charm and character and be prepared to be wowed with high ceilings and the gorgeous hardwood floors! A highlight of the house is an attractive kitchen with appealing custom cabinetry, granite and

    Stephanie Peduzzi-Baker Brattleboro Area Realty

    157 Pine St, Brattleboro, VT 05301
    • /8

      Est $727,112 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,244 Sq Ft

      438 River Rd, Guilford, VT 05301

      438 River Rd, Guilford, VT 05301
  • /60

    $620,000

    • 3 Beds
    • 2 Baths
    • 2,700 Sq Ft

    121 Dover Hill Rd, Dover, VT 05341

    Price reduced! Discover this Vermont countryside retreat offering an unbeatable blend of equestrian haven, homestead, and ski getaway, all on 5 private acres in desirable Dover. Enjoy perennial gardens bursting with color, abundant raspberry canes, and asparagus beds for beauty and bounty year-round. Step inside to vaulted ceilings, hardwood floors, and custom inlay bookshelves that add warmth

    Nick Sicard EXP Realty

    121 Dover Hill Rd, Dover, VT 05341
  • /34

    $4,800 per month

    • 3 Beds
    • 2 Baths
    • 1,342 Sq Ft
    • House for Rent

    4027 Vermont Route 100, Wardsboro, VT 05355

    Enjoy the natural beauty of the Wardsboro Brook right in your backyard while warming up after a day on the slopes by the firepit. After warming up, soothe any tension away in your muscles in the outdoor hot tub and top it off with time in the sauna.The open floor plan of the main living area has vaulted ceilings, a full kitchen and dining room with a partially opened wall equipped for a

    Peggy O'neill Cummings & Co

    4027 Vermont Route 100, Wardsboro, VT 05355
  • /19

    $250,000 Sold Jul 25, 2025

    • 900 Sq Ft
    • $278/SF
    • 45 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1971

    373 Brookline Rd, Athens, VT 05143

    Tucked away on 16 wooded acres in the quiet hills of Athens, Vermont, this unique property offers the kind of peace that’s getting harder to find. At its center is a simple, charming cabin with an open floor plan and vaulted ceiling, set just above a beaver pond that draws in wildlife and reflects the changing sky. It’s quiet here—really quiet. The kind of place where time slows down and the

    Daire Gibney Barrett and Valley Associates Inc.

    373 Brookline Rd, Athens, VT 05143
    • /24

      Est $222,822 Not Listed For Sale

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

      1751 Rockingham Rd, Rockingham, VT 05143

      1751 Rockingham Rd, Rockingham, VT 05143
  • /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
  • /12

    $2,000 per month

    • 1 Bed
    • 1 Bath
    • 535 Sq Ft
    • Apartment for Rent

    215 Main St Unit 203, Brattleboro, VT 05301

    This amazing apartment is available immediately. The view from the large windows in the kitchen and living room are of downtown Brattleboro. Recently renovated this space offers shared living room and kitchen with a large one bedroom apartment. The building has designated off street parking, and elevator in the building, along with laundry facilities and additional storage as well. Schedule

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    215 Main St Unit 203, Brattleboro, VT 05301
  • /50

    $469,000 Sold Jul 25, 2025

    • 1,346 Sq Ft
    • $348/SF
    • 47 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 2003

    2194 Mowrey Rd, Jamaica, VT 05343

    Diamond in the rough! Don't miss this opportunity to own a property in Jamaica, Vermont that has so much to offer! This property has been absolutely stunning in the past! Perched on a hill overlooking a private pond, fields that used to be pastures where your animals can roam and you can take in the local ridgeline view of the beautiful Green Mountains of Vermont! This is a true log home with

    Julie Lowe Lowe's Real Estate, LLC

    2194 Mowrey Rd, Jamaica, VT 05343
    • /14

      Not Listed For Sale

      5 Lahar Rd, Marlboro, VT 05351

      5 Lahar Rd, Marlboro, VT 05351
  • /60

    $849,000 Under Contract

    • 4 Beds
    • 4.5 Baths
    • 3,056 Sq Ft

    91 E Hill Rd, Wilmington, VT 05363

    Welcome to your dream escape! This beautifully renovated 4BR/5BA home is set on 4 private acres in the desirable Spruce Lake community, offering the perfect balance of comfort, nature, and year-round recreation. Thoughtfully updated in 2015, the home features a stunning addition that created a spacious primary suite with ensuite bath and generous walk-in closet. That same year, the first floor

    Donna Cote Four Seasons Sotheby's Int'l Realty

    91 E Hill Rd, Wilmington, VT 05363
  • /14

    $17,500 per month

    • 4 Beds
    • 2 Baths
    • 1,550 Sq Ft
    • House for Rent

    4591 Vermont 30, Jamaica, VT 05343

    This is a delightful Winter retreat...After a long fun day of skiing come home to this warm and cozy, meticulously maintained 4 bedroom home that is in great shape. Just 8 minutes from Stratton access Rd.Upstairs there are 2.5 bedrooms , kitchen, and living room with wood burning fireplace. Downstairs is another full bedroom and a 2nd kitchen, full bath, laundry and family room with TV,

    Wilkie Bushby TPW Real Estate

    4591 Vermont 30, Jamaica, VT 05343
  • /29

    $365,000 Sold Jul 25, 2025

    • 1,620 Sq Ft
    • $225/SF
    • 10 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 2006

    28 Greenleaf St, Brattleboro, VT 05301

    West Brattleboro contemporary cape situated on a large private partially fenced lot with fruit trees, raised bed gardens and plenty of outdoor recreational space. This sturdy, well-built house offers low maintenance and quality finishes like the standing seam metal roof and cement siding. Ample large windows bring the outside IN and provide lots of natural light. Interior features include: a

    Chris Long BHG Masiello Brattleboro

    28 Greenleaf St, Brattleboro, VT 05301
    • /36

      Est $513,951 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,050 Sq Ft

      208 Shady Ln, West Wardsboro, VT 05360

      208 Shady Ln, West Wardsboro, VT 05360
  • /59

    $1,395,000 Under Contract

    • 4 Beds
    • 4 Baths
    • 4,200 Sq Ft

    11 Corriveau Way, Wilmington, VT 05363

    Nestled in Vermont's Green Mountains, this stunning mountain home blends rustic beauty with modern luxury. Minutes from the exclusive Hermitage Club (property adjacent) in Wilmington, with private skiing, hiking, & a lifestyle enveloped in natural beauty. Built by Precision Craft Log & Timber Homes, the residence features hand-selected & hewned Idaho cedar logs & spans 4,125 square feet.

    Steve Goldfarb Deerfield Valley Real Estate

    11 Corriveau Way, Wilmington, VT 05363
  • /22

    $30,000 per month

    • 4 Beds
    • 2.5 Baths
    • 3,154 Sq Ft
    • House for Rent

    157 Old Sawmill Rd, Londonderry, VT 05148

    Wonderful Norwegian style chalet available for seasonal rental in southern VT ski country. Watch the snow cats on Magic Mountain from the home. Magic Mountain is 1.5 miles/4 minutes from the home. Stratton and Bromley Mountains are 20 minutes away. Okemo is 25 minutes away, and Killington is 55 minutes away. The VAST system for snowmobiling is accessible from the house, no need to trailer

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    157 Old Sawmill Rd, Londonderry, VT 05148
  • /27

    $487,500 Sold Jul 25, 2025

    • 1,618 Sq Ft
    • $301/SF
    • 12 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1985

    32 Christie Ln, Brattleboro, VT 05301

    This will be your favorite new listing. Tucked on a pocket of land, just beyond Memorial Park, you're in a neighborhood but it feels private, you see trees out every window. Custom-built home, 3 bedrooms, 2 1/2 updated baths, built in 1985. Incredibly warm and comfy. Cathedral ceiling with a wall of windows. Great kitchen for cooking, plenty of room for multiple chefs. Cozy nook for a small

    John Hatton Berkley & Veller Greenwood Country

    32 Christie Ln, Brattleboro, VT 05301
    • /17

      Est $450,109 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,609 Sq Ft

      38 Summit Meadows Cir, Dover, VT 05356

      38 Summit Meadows Cir, Dover, VT 05356
  • /54

    $645,000 Under Contract

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

    22 Hillside Dr, Wilmington, VT 05363

    This reimagined 1970s ski chalet blends timeless architecture with cutting-edge design, offering 4 bedrooms and 3 bathrooms across nearly 4 private acres. Thoughtfully curated for both personal enjoyment and short-term rental potential, the home is turnkey-ready—just bring your suitcase.The entry level features two ensuite bedrooms, each with fully renovated 3⁄4 baths, and a spacious lounge

    Lauren Niles Coldwell Banker LIFESTYLES - Quechee

    22 Hillside Dr, Wilmington, VT 05363
  • /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
  • /17

    $195,000 Sold Jul 25, 2025

    • 1,414 Sq Ft
    • $138/SF
    • 26 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1880

    2147 N Main St, Londonderry, VT 05148

    Terrific in-town location! Improvements include new roof and trim last year, 24kw Generator, serviced annually, new flooring on first level and new washer and dryer. Easy to maintain yard space, walk to the plaza for shopping and restaurants, minutes to 3 ski resorts!

    Lisa Kelley Cummings & Co

    2147 N Main St, Londonderry, VT 05148
    • /30

      Est $625,834 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,200 Sq Ft

      79 Wilmington Heights, Wilmington, VT 05363

      79 Wilmington Heights, Wilmington, VT 05363

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