30,509

Windham County, VT Homes

Section Image
  • 0 W Hill Rd, Jamaica, VT 05343
    0 W Hill Rd, Jamaica, VT 05343
    0 W Hill Rd, Jamaica, VT 05343
    /11

    $495,000

    • Land
    • 68.89 Acres
    • $7,185 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 solid woods

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • 197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301
    197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301
    197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301
    /38

    $2,000 per month

    • 3 Beds
    • 1 Bath
    • 2,200 Sq Ft
    • Condo for Rent

    197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301

    Available December 1Spacious and sun-filled 3-bedroom apartment with an additional office, offering room to live, work, and relax. Enjoy a full dining room, large kitchen, comfortable living room, and your own private porch—perfect for morning coffee or unwinding at the end of the day.This home features new windows, clean carpeting, and excellent natural light from every direction. You’ll

    197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301
  • 188 Sugar Bush Rd, Londonderry, VT 05148
    188 Sugar Bush Rd, Londonderry, VT 05148
    188 Sugar Bush Rd, Londonderry, VT 05148
    /42

    $375,000 Sold Nov 25, 2025

    • 1,882 Sq Ft
    • $199/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1978

    188 Sugar Bush Rd, Londonderry, VT 05148

    Sitting above Londonderry Village, this 3-bedroom, 2-bathroom home offers the perfect blend of rustic character, privacy, and easy access to local amenities. Step inside through a spacious enclosed porch—ideal for a peaceful sitting area, storing firewood, or serving as a functional mudroom. The main level features exposed post-and-beam construction, wide-plank wood floors, and a stunning

    Rachel Febbie EXP Realty

    188 Sugar Bush Rd, Londonderry, VT 05148
    • 38 Summit Meadows Cir, Dover, VT 05356
      38 Summit Meadows Cir, Dover, VT 05356
      38 Summit Meadows Cir, Dover, VT 05356
      /17

      Est $475,350 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,309 Sq Ft

      38 Summit Meadows Cir, Dover, VT 05356

      38 Summit Meadows Cir, Dover, VT 05356
  • 0 W Hill Rd, Jamaica, VT 05343
    0 W Hill Rd, Jamaica, VT 05343
    0 W Hill Rd, Jamaica, VT 05343
    /7

    $195,000

    • Land
    • 15.27 Acres
    • $12,770 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
  • 67 Vermont Route 100, Jamaica, VT 05155
    67 Vermont Route 100, Jamaica, VT 05155
    67 Vermont Route 100, Jamaica, VT 05155
    /29

    $18,000 per month

    • 4 Beds
    • 3 Baths
    • 3,200 Sq Ft
    • House for Rent

    67 Vermont Route 100, Jamaica, VT 05155

    Discover the charm of this delightful rental nestled along a quintessential river in Vermont! With its prime location on a major road, you're just 7 miles away from the slopes of the Stratton Mountain ski resort, making it the perfect getaway for winter sports enthusiasts. This spacious home boasts multiple living areas, ensuring everyone has their own space to relax and unwind. With four

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    67 Vermont Route 100, Jamaica, VT 05155
  • 19 Village Lodge Rd Unit 209, Stratton, VT 05155
    19 Village Lodge Rd Unit 209, Stratton, VT 05155
    19 Village Lodge Rd Unit 209, Stratton, VT 05155
    /36

    $975,000 Sold Nov 24, 2025

    • 1,697 Sq Ft
    • $575/SF
    • 15 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2004

    19 Village Lodge Rd Unit 209, Stratton, VT 05155

    Ski-In/Ski-Out Luxury: The Landmark at Stratton Experience the quintessential Vermont lifestyle you've always dreamed of with this truly extraordinary residence at The Landmark at Stratton. Perfectly positioned, this condo places you at the heart of it all, where you are quite literally steps from the lifts, the charming Stratton Village, and every amenity the mountain has to offer. Forget

    Robin Apps Four Seasons Sotheby's Int'l Realty

    19 Village Lodge Rd Unit 209, Stratton, VT 05155
    • 79 Wilmington Heights, Wilmington, VT 05363
      79 Wilmington Heights, Wilmington, VT 05363
      79 Wilmington Heights, Wilmington, VT 05363
      /30

      Est $606,967 Not Listed For Sale

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

      79 Wilmington Heights, Wilmington, VT 05363

      79 Wilmington Heights, Wilmington, VT 05363
  • 0 W Hill Rd, Jamaica, VT 05343
    0 W Hill Rd, Jamaica, VT 05343
    0 W Hill Rd, Jamaica, VT 05343
    /15

    $650,000

    • Land
    • 51.93 Acres
    • $12,517 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 unique, and

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • 950 Western Ave, Brattleboro, VT 05301
    950 Western Ave, Brattleboro, VT 05301
    950 Western Ave, Brattleboro, VT 05301
    /9

    $2,500 per month

    • 2 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Townhouse for Rent

    950 Western Ave, Brattleboro, VT 05301

    This spacious townhouse is in the back of an historic building situated just off the common in West Brattleboro. Enjoy a quiet living spot surrounded by beautiful stone walls and gardens. Two large bedrooms and two full baths, with an additional room for office or hobbies. Open concept living room / kitchen with vaulted ceiling. A wood paneled dining area done in pub (Stube) style.

    950 Western Ave, Brattleboro, VT 05301
  • 275 Pams Hill Rd, Wardsboro, VT 05355
    275 Pams Hill Rd, Wardsboro, VT 05355
    275 Pams Hill Rd, Wardsboro, VT 05355
    /29

    $495,000 Sold Nov 21, 2025

    • 1,500 Sq Ft
    • $330/SF
    • 59 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1969

    275 Pams Hill Rd, Wardsboro, VT 05355

    Absolutely meticulous and renovated gambrel chalet with private parcel and easy access to both Mount Snow and Stratton. This home exudes the vibe of a true Vermont ski retreat. Inside you are treated to extensive upgrades throughout making it truly turn key. There is a large great room with expansive windows, natural woodwork, great natural light, and efficient gas stove, a beautiful updated

    Adam Palmiter Berkley & Veller Greenwood/Dover

    275 Pams Hill Rd, Wardsboro, VT 05355
    • 30 Styles Branch Rd Unit 309, Stratton, VT 05360
      30 Styles Branch Rd Unit 309, Stratton, VT 05360
      30 Styles Branch Rd Unit 309, 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
  • 9A Dover Springs Ln, Dover, VT 05356
    9A Dover Springs Ln, Dover, VT 05356
    9A Dover Springs Ln, Dover, VT 05356
    /35

    $875,000

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

    9A Dover Springs Ln, Dover, VT 05356

    Greenspring townhome across the street from the Mount Snow ski resort with stunning direct views of the ski trails. This 4 bedroom, 4 bath unit is being offered by the original owners and has been well maintained and never rented. It features an an open concept floor plan with living room with vaulted ceiling and wood burning two sided fireplace, large kitchen with breakfast bar on the island,

    Adam Palmiter Berkley & Veller Greenwood/Dover

    9A Dover Springs Ln, Dover, VT 05356
  • 1070 Hells Peak Rd, Londonderry, VT 05148
    1070 Hells Peak Rd, Londonderry, VT 05148
    1070 Hells Peak Rd, Londonderry, VT 05148
    /23

    $5,000 per month

    • 3 Beds
    • 1.5 Baths
    • 2,092 Sq Ft
    • House for Rent

    1070 Hells Peak Rd, Londonderry, VT 05148

    Charming Antique Home on 60 Acres – Hell’s Peak Road, Londonderry, Vermont Set on 60 rolling acres in the quaint hamlet of Londonderry, this beautiful antique home offers the perfect Vermont retreat. With availability for the upcoming 2025–26 ski season, it’s an ideal opportunity for those seeking both seasonal enjoyment and year-round serenity. Located near three premier ski areas with a direct

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    1070 Hells Peak Rd, Londonderry, VT 05148
  • 202 Pratt Bridge Rd, Jamaica, VT 05343
    202 Pratt Bridge Rd, Jamaica, VT 05343
    202 Pratt Bridge Rd, Jamaica, VT 05343
    /41

    $785,000 Sold Nov 21, 2025

    • 2,800 Sq Ft
    • $280/SF
    • 28 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1966

    202 Pratt Bridge Rd, Jamaica, VT 05343

    Your slice of heaven awaits! Leave your worries behind and step into a beautiful Southern Vermont home that's truly turnkey. This well-designed, fully furnished, 3 bedroom, 2.5 bath home on 1.8+/- professionally landscaped acres offers privacy and convenience to the area's premier slopes, trails and natural beauty. The heart of the home is an expansive chef’s kitchen where country cabinetry and

    Geralyn Donohue Engel & Völkers Okemo

    202 Pratt Bridge Rd, Jamaica, VT 05343
    • 1 Wildwood Dr, West Brattleboro, VT 05301
      1 Wildwood Dr, West Brattleboro, VT 05301
      1 Wildwood Dr, West Brattleboro, VT 05301
      /26

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 962 Sq Ft

      1 Wildwood Dr, West Brattleboro, VT 05301

      1 Wildwood Dr, West Brattleboro, VT 05301
  • 12 Lilla Ln, Wilmington, VT 05363
    12 Lilla Ln, Wilmington, VT 05363
    12 Lilla Ln, Wilmington, VT 05363
    /21

    $489,000

    • 3 Beds
    • 2 Baths
    • 2,003 Sq Ft

    12 Lilla Ln, Wilmington, VT 05363

    Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private

    Adam Palmiter Berkley & Veller Greenwood/Dover

    12 Lilla Ln, Wilmington, VT 05363
  • 566 S Main St Unit 566 South Main Street, Brattleboro, VT 05301
    566 S Main St Unit 566 South Main Street, Brattleboro, VT 05301
    566 S Main St Unit 566 South Main Street, Brattleboro, VT 05301
    /12

    $1,700 per month

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Condo for Rent

    566 S Main St Unit 566 South Main Street, Brattleboro, VT 05301

    Naturally sunlight 3 bedroom apartment with off street parking (2spots) within walking distances to Main Street, grocery stores, hospital, gym, restaurant, high school, middle school, career center, elementary school, and Fort Dummer State Park hiking trails.

    566 S Main St Unit 566 South Main Street, Brattleboro, VT 05301
  • 871 Streeter Hill Rd, Whitingham, VT 05361
    871 Streeter Hill Rd, Whitingham, VT 05361
    871 Streeter Hill Rd, Whitingham, VT 05361
    /36

    $380,000 Sold Nov 21, 2025

    • 1,456 Sq Ft
    • $261/SF
    • 79 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1989

    871 Streeter Hill Rd, Whitingham, VT 05361

    This Real Log Home is situated on nearly 16 acres at the end of a gravel road within two miles of two lakes (Harriman Reservoir and Lake Sadawga) and their boat launches, less than 30 minutes to Mt Snow and Stratton Resorts and also has access to thousands of acres of Green Mountain National Forest in the immediate area for hiking/biking snowshoeing and much more. The main VAST snowmobile trail

    Chris Long BHG Masiello Brattleboro

    871 Streeter Hill Rd, Whitingham, VT 05361
    • 97 Stratton Dr, Townshend, VT 05353
      97 Stratton Dr, Townshend, VT 05353
      97 Stratton Dr, Townshend, VT 05353
      /32

      Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 3,529 Sq Ft

      97 Stratton Dr, Townshend, VT 05353

      97 Stratton Dr, Townshend, VT 05353
  • 42 Blackberry Ln, Jamaica, VT 05343
    42 Blackberry Ln, Jamaica, VT 05343
    42 Blackberry Ln, Jamaica, VT 05343
    /60

    $875,000

    • 5 Beds
    • 4.5 Baths
    • 3,840 Sq Ft

    42 Blackberry Ln, Jamaica, VT 05343

    Welcome to "Sweet Berry Farm", a charming Vermont homestead blending 1850s character with a spacious modern addition. Set on 5.7 private acres in Jamaica, this property offers abundant natural beauty—mature apple trees, blueberry and blackberry bushes and vibrant seasonal gardens. The expanded farmhouse provides exceptional space for living and entertaining. The main floor features an open living

    MaryKate Grey Stratton Real Estate

    42 Blackberry Ln, Jamaica, VT 05343
  • 4 Elliot St Unit 7, Brattleboro, VT 05301
    4 Elliot St Unit 7, Brattleboro, VT 05301
    4 Elliot St Unit 7, Brattleboro, VT 05301
    /7

    $1,700 per month

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

    4 Elliot St Unit 7, Brattleboro, VT 05301

    In town, one bedroom apartment, with bright sunlit rooms. The apartment is only three rooms and has a combined kitchen and living room, with a separate bedroom. This apartment is furnished. Coin operated laundry is on site, trash removal, and a secure building. Pet friendly building

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 7, Brattleboro, VT 05301
  • E9 Loon Circle Private, Londonderry, VT 05148
    E9 Loon Circle Private, Londonderry, VT 05148
    E9 Loon Circle Private, Londonderry, VT 05148
    /13

    $38,000 Sold Nov 21, 2025

    • Land
    • 2.3 Acres
    • $16,522 per Acre
    • 12 Days On Market

    E9 Loon Circle Private, Londonderry, VT 05148

    A 2.3-acre parcel of land offers a remarkable blend of accessibility and scenic beauty, accompanied by a wastewater system permit for a three-bedroom residence. It is situated just 5 minutes from Magic Mountain and 15-20 minutes from Stratton, Bromley, and Okemo. The VAST trail is nearby, providing opportunities for snowmobiling, while numerous hiking trails are only a short walk away. Lowell

    Mike England Michael England Real Estate

    E9 Loon Circle Private, Londonderry, VT 05148
    • 443 Dover Rd, Newfane, VT 05351
      443 Dover Rd, Newfane, VT 05351
      443 Dover Rd, Newfane, VT 05351
      /21

      Est $325,347 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft

      443 Dover Rd, Newfane, VT 05351

      443 Dover Rd, Newfane, VT 05351
  • 457 Ray Hill Rd, Wilmington, VT 05363
    457 Ray Hill Rd, Wilmington, VT 05363
    457 Ray Hill Rd, Wilmington, VT 05363
    /23

    $685,000

    • 3 Beds
    • 2.5 Baths
    • 1,874 Sq Ft

    457 Ray Hill Rd, Wilmington, VT 05363

    Lovely expanded farmhouse just up from the village of Wilmington and with mountain views and gorgeous exposure on 2.7 acres of private open land. This charming home is just a short drive to both the Mount Snow and Hermitage Club ski resorts, and nearby lakes, with easy access despite it's private location. The home sits on a pastoral lot with gorgeous westerly views over Haystack Mountain for

    Adam Palmiter Berkley & Veller Greenwood/Dover

    457 Ray Hill Rd, Wilmington, VT 05363
  • 995 Western Ave Unit 200, Brattleboro, VT 05301
    995 Western Ave Unit 200, Brattleboro, VT 05301
    995 Western Ave Unit 200, Brattleboro, VT 05301
    /13

    $1,800 per month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Townhouse for Rent

    995 Western Ave Unit 200, Brattleboro, VT 05301

    This full floor, renovated two-bedroom apartment is up a flight of steps on the 2nd floor. Amenities include eat-in kitchen with tile backsplash, dishwasher, windows on all sides, pantry or small office, a private, glassed-in porch with woods and mountain views, 1/2 open garage plus parking in the driveway for a second car, separate entrance, and a large backyard. Mowing, snow removal and heat

    995 Western Ave Unit 200, Brattleboro, VT 05301
  • 5997 Vermont 30, Jamaica, VT 05343
    5997 Vermont 30, Jamaica, VT 05343
    5997 Vermont 30, Jamaica, VT 05343
    /17

    $215,000 Sold Nov 21, 2025

    • 1,387 Sq Ft
    • $155/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1999

    5997 Vermont 30, Jamaica, VT 05343

    Nestled on 5.3 private acres, this charming 3-bedroom, 2-bath log home offers a classic Vermont retreat surrounded by nature. Enjoy the warmth and character of log construction, with inviting living spaces and plenty of room to relax after a day on the slopes. A convenient storage shed provides space for your outdoor gear and tools. Perfectly located just a short drive to Stratton, Bromley, and

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    5997 Vermont 30, Jamaica, VT 05343
    • 43 High Point Dr Unit D23, Stratton, VT 05360
      43 High Point Dr Unit D23, Stratton, VT 05360
      43 High Point Dr Unit D23, Stratton, VT 05360
      /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
  • 1375 Sheldon Hill Rd, Wardsboro, VT 05355
    1375 Sheldon Hill Rd, Wardsboro, VT 05355
    1375 Sheldon Hill Rd, Wardsboro, VT 05355
    /34

    $620,000

    • 6 Beds
    • 4 Baths
    • 3,592 Sq Ft

    1375 Sheldon Hill Rd, Wardsboro, VT 05355

    Stunning unique 2024 renovated chalet with rare 2+ acre parcel and easy access to both Mount Snow and Stratton. This home exudes the vibe of a true Vermont ski retreat. Inside you are treated to a large open concept great room with vaulted ceilings, natural woodwork, and great natural light throughout thanks to large windows and transoms. There is a gas fireplace with stone hearth, upscale custom

    Adam Palmiter Berkley & Veller Greenwood/Dover

    1375 Sheldon Hill Rd, Wardsboro, VT 05355
  • 1138 River Rd, Jamaica, VT 05343
    1138 River Rd, Jamaica, VT 05343
    1138 River Rd, Jamaica, VT 05343
    /33

    $6,000 per month

    • 5 Beds
    • 3 Baths
    • 2,912 Sq Ft
    • House for Rent

    1138 River Rd, Jamaica, VT 05343

    WINTER MONTHLY RENTAL - $6,000/Month Plus prepaid utilities ($750/month) | Total due in Full Before Occupancy. Spend the winter in the mountains with this spacious and fully updated 5-bedroom, 3-bath home with a cozy loft in scenic Jamaica, VT. Nestled in a quiet wooded setting, this inviting retreat comfortably accommodates up to 12 guests. After a day on the slopes, relax by the fireplace with

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    1138 River Rd, Jamaica, VT 05343
  • 734 Missing Link Rd, Bellows Falls, VT 05101
    734 Missing Link Rd, Bellows Falls, VT 05101
    734 Missing Link Rd, Bellows Falls, VT 05101
    /20

    $180,000 Sold Nov 21, 2025

    • 1,008 Sq Ft
    • $179/SF
    • 3 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1980

    734 Missing Link Rd, Bellows Falls, VT 05101

    Welcome home to this peaceful retreat, set on nearly 3 acres with just the right amount of privacy. The exterior is almost complete with newer vinyl siding, replacement windows, and a standing seam roof already in place. Inside, you’ll find a space ready for your personal touch — the perfect opportunity to design the home you’ve always envisioned. Located in a quiet location with wonderful

    Linda Benoit Highland Realty

    734 Missing Link Rd, Bellows Falls, VT 05101
    • 2900 Route 121 E, Grafton, VT 05146
      2900 Route 121 E, Grafton, VT 05146
      2900 Route 121 E, Grafton, VT 05146
      /40

      Est $551,926 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,613 Sq Ft

      2900 Route 121 E, Grafton, VT 05146

      2900 Route 121 E, Grafton, VT 05146
  • 4880 Pikes Falls Rd, Jamaica, VT 05343
    4880 Pikes Falls Rd, Jamaica, VT 05343
    4880 Pikes Falls Rd, Jamaica, VT 05343
    /40

    $890,000

    • 5 Beds
    • 3.5 Baths
    • 3,218 Sq Ft

    4880 Pikes Falls Rd, Jamaica, VT 05343

    This majestic log home offers peaceful mountain living with room for Everyone. Discover your tranquil 5-bedroom, 4-bathroom family retreat nestled just minutes from the year-round activities at Stratton Ski Resort. This authentic and expansive log cabin exudes classic Vermont charm. The inviting main living area is flooded with natural light, featuring an efficient wood stove to provide cozy

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    4880 Pikes Falls Rd, Jamaica, VT 05343
  • 4669 Vermont Route 100, Londonderry, VT 05148
    4669 Vermont Route 100, Londonderry, VT 05148
    4669 Vermont Route 100, Londonderry, VT 05148
    /32

    $35,000 per month

    • 7 Beds
    • 4.5 Baths
    • 5,343 Sq Ft
    • House for Rent

    4669 Vermont Route 100, Londonderry, VT 05148

    GET THE BEST OF THE BEST. Just the 3 prime skiing months..JAN- MARCH. NOW AT A VERY REDUCED RATE!! Very Special rental opportunity... for 2 very lucky families. Sleeps 12+ easily. An amazing house, property, outbuildings, barns, land, total privacy.. to spend a totally fun enchanting winter together in Vermont heaven. This beautifully restored Vermont classic farmhouse has room for many, 2

    Wilkie Bushby TPW Real Estate

    4669 Vermont Route 100, Londonderry, VT 05148
  • 14 Cherry Hill St, Bellows Falls, VT 05101
    14 Cherry Hill St, Bellows Falls, VT 05101
    14 Cherry Hill St, Bellows Falls, VT 05101
    /34

    $150,000 Sold Nov 21, 2025

    • 1,824 Sq Ft
    • $82/SF
    • 180 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1880

    14 Cherry Hill St, Bellows Falls, VT 05101

    Located in the heart of Bellows Falls, Vermont, this charming 1880's home showcases classic 19th-century architecture. Set on a 0.30+/-acre lot, the property includes three bedrooms and one full bathroom. The open concept living and dining areas provide a welcoming space for gatherings, while the adjoining family room offers extra room for an office or flexible use. The full bathroom is

    Rob Weltz Barrett and Valley Associates Inc.

    14 Cherry Hill St, Bellows Falls, VT 05101
    • 5 Rice Hill Rd, Dover, VT 05341
      5 Rice Hill Rd, Dover, VT 05341
      5 Rice Hill Rd, Dover, VT 05341
      /34

      Est $817,375 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,412 Sq Ft

      5 Rice Hill Rd, Dover, VT 05341

      5 Rice Hill Rd, Dover, VT 05341
  • 261 Handle Rd, Dover, VT 05356
    261 Handle Rd, Dover, VT 05356
    261 Handle Rd, Dover, VT 05356
    /37

    $874,000

    • 6 Beds
    • 3 Baths
    • 2,900 Sq Ft

    261 Handle Rd, Dover, VT 05356

    Slopeside 6 Bedroom Ski Chalet at Carinthia Base, Mount Snow This ski chalet is perfectly positioned at the base of Carinthia, offering true slopeside access and unmatched convenience. Step out your door and onto the trails, with the Carinthia Base Lodge, terrain parks, lifts, and all the action of the mountain just steps away. Inside, the home blends classic chalet character with thoughtful

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    261 Handle Rd, Dover, VT 05356
  • 1303 Goodaleville Rd, South Londonderry, VT 05155
    1303 Goodaleville Rd, South Londonderry, VT 05155
    1303 Goodaleville Rd, South Londonderry, VT 05155
    /24

    $40,000 per month

    • 5 Beds
    • 5 Baths
    • 3,000 Sq Ft
    • House for Rent

    1303 Goodaleville Rd, South Londonderry, VT 05155

    Stunning expansive farmhouse ready for your winter enjoyment. Just ten minutes from Stratton's access road entrance . Located on a beautiful country road. 5 attractive bedrooms , 3 full baths, 2 half baths. Yoga room. Sauna. Wood burning fireplace. Garage. This decorator appointed home is the perfect winter vacation respite for you and your family and friends. Utilities , Owners's

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    1303 Goodaleville Rd, South Londonderry, VT 05155
  • 123 Oak Hill Rd, West Wardsboro, VT 05360
    123 Oak Hill Rd, West Wardsboro, VT 05360
    123 Oak Hill Rd, West Wardsboro, VT 05360
    /24

    $290,000 Sold Nov 21, 2025

    • 1,188 Sq Ft
    • $244/SF
    • 9 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1988

    123 Oak Hill Rd, West Wardsboro, VT 05360

    Discover the perfect blend of comfort and tranquility in this three bedroom, 2 bath ranch-style home nestled within a peaceful wooded neighborhood. Conveniently location between two major ski areas, Mount Snow and Stratton Mountain. The open living and dining areas feature plenty of natural light, with vaulted ceilings and skylights, creating a warm and inviting space. Three comfortable sized

    Jamie Wylie Stratton Real Estate

    123 Oak Hill Rd, West Wardsboro, VT 05360
    • 951 Dover Rd, South Newfane, VT 05351
      951 Dover Rd, South Newfane, VT 05351
      951 Dover Rd, South Newfane, VT 05351
      /33

      Est $203,510 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,369 Sq Ft

      951 Dover Rd, South Newfane, VT 05351

      951 Dover Rd, South Newfane, VT 05351

Showing Results 41 - 80, Page 2 of 18

Vermont Windham County

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group