30,390

Windham County, VT Homes

Section Image
  • /79

    $275,000

    • Land
    • 22.32 Acres
    • $12,321 per Acre

    81 Parish Hill Rd Unit 26, Newfane, VT 05345

    Tucked away in the quiet hills of South Newfane, Vermont, this property presents an excellent opportunity to own a secluded off-grid retreat with endless potential. Spanning 22.32 acres of mixed timberland, the land offers both natural beauty and outdoor recreation, while the cabin provides a comfortable base that is already well on its way to completion.The cabin itself measures 715 square feet

    Chad Bruyette

    81 Parish Hill Rd Unit 26, Newfane, VT 05345
  • /23

    $5,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • House for Rent

    923 Landgrove Rd, Londonderry, VT 05148

    This three-bedroom, three-bathroom cape is located in the exclusive rural town of Landgrove and it is absolutely darling. Situated on a huge parcel of land equipped with space for snowshoeing, cross-country skiing, and a pond. Enjoy your "tucked away" Norman Rockwell style winter/ski home this season and reap the benefits and ease of being just a short drive from Stratton, Bromely,

    Peggy O'neill Cummings & Co

    923 Landgrove Rd, Londonderry, VT 05148
  • /2

    $55,000 Sold Sep 12, 2025

    • Land
    • 1 Acre
    • $55,000 per Acre
    • 0 Days On Market

    235 Valley View Rd, Dover, VT 05356

    Lovely wooded 1 acre parcel with Wastewater permit (WW-2-7531) for a 3 bedroom single family residence.

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    235 Valley View Rd, Dover, VT 05356
    • /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
    • 51.93 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
  • /17

    $20,000 per month

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • House for Rent

    72 Depot St, Jamaica, VT 05343

    Seasonal Rental Available! Charming and cozy 1900 Cape available for winter rental from November through April. Located in a peaceful village setting, walk to the charming village of Jamaica. Only 15 minutes to Stratton Mountain. This 3-bedroom, 2-bath home offers the perfect ski-season escape with classic New England charm.

    Christina Dryden Berkshire Hathaway HomeServices Stratton Home

    72 Depot St, Jamaica, VT 05343
  • /13

    $269,141 Sold Sep 12, 2025

    • 956 Sq Ft
    • $282/SF
    • 6 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1929

    81 Oak Grove Ave, Brattleboro, VT 05301

    Welcome to this delightful 2-bedroom, 1-bathroom bungalow nestled in one of the most sought-after neighborhoods! Brimming with character and warmth, this cozy home offers a perfect blend of vintage charm and modern convenience. Many upgrades including a garage makeover, storage shed, roof, back porch, and so much more. Step inside to find a bright, inviting living space with hardwood floors,

    Claire Renaud Berkley & Veller Greenwood Country

    81 Oak Grove Ave, 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
  • /11

    $595,000

    • Land
    • 68.89 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
  • /32

    $40,000 per month

    • 4 Beds
    • 4 Baths
    • 3,500 Sq Ft
    • House for Rent

    896 Melendy Hill Rd, Londonderry, VT 05155

    Stunning, gorgeous, brand-new post-and-beam contemporary home for rent this season. Barely lived in, never rented. ALL NEW, EVERYTHING. 4 bedrooms, all with en-suite bathrooms. Huge living room with 2-story windows facing east and morning views of Magic. The house faces south, so it is sunny and gorgeous all day. Close to ALL 3 local ski areas! New Gourmet kitchen, marble counters, new

    Wilkie Bushby TPW Real Estate

    896 Melendy Hill Rd, Londonderry, VT 05155
  • /20

    $265,000 Sold Sep 12, 2025

    • 1,178 Sq Ft
    • $225/SF
    • 6 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1970

    17 Winter Ct, Brattleboro, VT 05301

    Classic Ranch Style Home! Just starting out or thinking of downsizing? This could be the one! Nestled in a sweet neighborhood, this charming ranch offers easy one-level living just minutes from downtown shopping, schools, and recreation. Set on a manageable 0.2 acre lot, this home features a bright enclosed porch/bonus room perfect for morning coffee, reading, or relaxing year-round. Continuing

    Liz LaVorgna Berkley & Veller Greenwood Country

    17 Winter Ct, Brattleboro, VT 05301
    • /21

      Est $325,333 Not Listed For Sale

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

      443 Dover Rd, Newfane, VT 05351

      443 Dover Rd, Newfane, VT 05351
  • /8

    $320,000

    • Land
    • 34.53 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
  • /13

    $2,350 per month

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft
    • Apartment for Rent

    4 Elliot St Unit 8, Brattleboro, VT 05301

    The National, featuring this 2 Bedroom apartment with bright sunlit rooms, amazing hardwood floors and views of downtown and the mountain. Coin operated Laundry is on site and off street parking is available in the parking garage. The building is pet friendly

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 8, Brattleboro, VT 05301
  • /44

    $655,000 Sold Sep 12, 2025

    • 1,530 Sq Ft
    • $428/SF
    • 7 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 2000

    1176 E Dover Rd, Wardsboro, VT 05355

    A True Vermont Retreat – Serene, Private, and Exceptional. Tucked away at the end of a winding private drive, this captivating cape-style home is simply flawless. Lovingly maintained for over 30 years, the property reflects a deep sense of care, dedication, and pride. Now, as the current owners prepare for their next chapter, a rare opportunity arises to become the next steward of s exceptional

    Thomas Dahlin Berkley & Veller Greenwood Country

    1176 E Dover Rd, Wardsboro, VT 05355
    • /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
  • /7

    $235,000

    • Land
    • 15.27 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
  • /12

    $2,200 per month

    • 2 Beds
    • 1 Bath
    • 790 Sq Ft
    • Apartment for Rent

    4 Elliot St Unit 6, Brattleboro, VT 05301

    The National, featuring this 2 Bedroom apartment with bright sunlit rooms, amazing hardwood floors and views of downtown and the mountain. Coin operated Laundry is on site and off street parking is available in the parking garage. The building is pet friendly

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 6, Brattleboro, VT 05301
  • /41

    $550,000 Sold Sep 12, 2025

    • 1,608 Sq Ft
    • $342/SF
    • 13 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1988

    11 Dutchman Ln Unit 4B, Wilmington, VT 05363

    Stylish Powderhorn Village Townhome – Prime Location Near Hermitage Club & Mount Snow.Welcome to this beautiful 3-bedroom, 2.5-bath townhome nestled in the sought-after Powderhorn Village community. The home has been thoughtfully updated throughout, with an inviting gas fireplace, open living space, and a private deck offering modern comfort with a mountain charm.This spacious home

    Lisa Mirando Deerfield Valley Real Estate

    11 Dutchman Ln Unit 4B, Wilmington, VT 05363
    • /40

      Est $559,174 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
  • /46

    $992,000

    • 4 Beds
    • 4.5 Baths
    • 3,100 Sq Ft

    33 Carinthia Rd, Dover, VT 05356

    3000+ Sq ft, 4 beds plus den, 4.5 baths, 3 fireplaces and an attached garage all in the Carinthia base area of Mount Snow Ski Resort!! This 4-bedroom, 4.5-bath home offers a versatile layout with multiple en-suite bedrooms, 3 wood burning fireplaces, and a sauna, just steps from the slopes. The main level showcases a spacious sunken living room with cathedral ceilings and soaring brick fireplace,

    Jacki Murano Southern Vermont Realty Group

    33 Carinthia Rd, Dover, VT 05356
  • /18

    $20,000 per month

    • 3 Beds
    • 2 Baths
    • 2,255 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
  • /10

    $585,000 Sold Sep 12, 2025

    • 1,679 Sq Ft
    • $348/SF
    • 17 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2016

    154 Haystack Rd, Wilmington, VT 05363

    Opportunity knocks to put your own touches to this Log home that is studded out and ready to move forward! Amazing location minutes to The Hermitage Club, Mount Snow and Haystack golf which offers golf, snowshoeing and weekend dining! Soaring great room with gas fireplace, three bedrooms, two and one half baths and a large unfinished basement offering many future options.Sale is subject to

    Heidi Zizza Four Seasons Sotheby's Int'l Realty

    154 Haystack Rd, Wilmington, VT 05363
    • /34

      Est $808,377 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
  • /39

    $481,675

    • 4 Beds
    • 2 Baths
    • 2,240 Sq Ft

    645 Stratton Arlington Rd, West Wardsboro, VT 05360

    Beautifully updated rustic log home nestled just 6 miles from Mount Snow and 10 miles from Stratton, offers the perfect mountain retreat or year-round residence. Boasting two spacious levels of living, the home includes a flexible lower level ideal for use as an in-law suite, guest quarters, or additional entertaining space.Step inside to find warm, inviting interior with all new

    Lisa Mirando Deerfield Valley Real Estate

    645 Stratton Arlington Rd, West Wardsboro, VT 05360
  • /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
  • /11

    $35,000 Sold Sep 11, 2025

    • Land
    • 2.21 Acres
    • $15,837 per Acre
    • 30 Days On Market

    Lot 2 Wellington Hill Rd W, Westminster, VT 05346

    2.21-acre parcel of land located in the town of Westminster, Vermont. This lot features classic Vermont stone walls, lovely trees and road frontage. The landowner notes that the flat portion of the lot has been cleared and that there are distant mountain views from the front section of the property when cleared. They also mention that the location may be suitable for a home, yurt, or tiny house

    Erica Reynolds Southern Vermont Realty Group

    Lot 2 Wellington Hill Rd W, Westminster, VT 05346
    • /33

      Est $197,373 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
  • /47

    $550,000

    • 4 Beds
    • 4 Baths
    • 2,372 Sq Ft

    187 Hillwinds Rd, Brattleboro, VT 05301

    Welcome home! Four bedroom, 4-bathroom home with dedicated office space is located in one of the area’s most desirable communities. Just minutes from Brattleboro, it offers the perfect blend of convenience, comfort, and outdoor living, with walking trails right nearby. The bright, open layout is ideal for everyday living and entertaining, featuring a welcoming kitchen, dining, and living area. A

    Claire Renaud Berkley & Veller Greenwood Country

    187 Hillwinds Rd, Brattleboro, VT 05301
  • /34

    $4,400 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
  • /34

    $520,000 Sold Sep 11, 2025

    • 3,213 Sq Ft
    • $162/SF
    • 5 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 1818

    3708 Vermont 30, Jamaica, VT 05343

    Located in the heart of downtown Jamaica, Vermont, this spacious and beautifully designed Colonial home offers the perfect blend of charm, comfort, and convenience. With 5 bedrooms and 5 bathrooms, there’s plenty of space for a large family or frequent guests. Just minutes from premier ski resorts—Stratton, Bromley, and Magic Mountain—this home is an ideal base for winter and summer adventures.

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    3708 Vermont 30, Jamaica, VT 05343
    • /37

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,655 Sq Ft

      3 Valley View Unit CHB004, Wilmington, VT 05363

      3 Valley View Unit CHB004, Wilmington, VT 05363
  • /14

    $815,000

    • 2 Beds
    • 2 Baths
    • 1,263 Sq Ft

    19 Village Lodge Rd Unit 309, Stratton, VT 05155

    In the heart of the Stratton Mountain Village attached to the iconic Clock Tower, Landmark is prime location for all that that the Resort has to offer. This two bedroom floorplan is one of the largest in the community. Ample living and bedroom space as well as a nice separate dining area. Direct mountain views with southern exposure for warm light. Beautifully appointed furniture and ready for

    Timothy Mich Doddridge Stratton Real Estate

    19 Village Lodge Rd Unit 309, Stratton, VT 05155
  • /14

    $17,500 per month

    • 4 Beds
    • 2 Baths
    • 1,950 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
  • /58

    $980,000 Sold Sep 11, 2025

    • 3,588 Sq Ft
    • $273/SF
    • 87 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2007

    524 Reilly Rd, Londonderry, VT 05148

    Are you looking for a home with spectacular winter views of Stratton Mountain and seated on a private lot? Look no further. This home has it all. Spectacular views, soaring spacious rooms and more in this stunning Vermont facade log home. Vaulted ceilings and a dramatic stone fireplace framed by multiple windows looking out at your full wrap around deck and the slopes of Stratton across the open

    Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

    524 Reilly Rd, Londonderry, VT 05148
    • /14

      Est $248,280 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,248 Sq Ft

      23 Robin Way, Brattleboro, VT 05301

      23 Robin Way, Brattleboro, VT 05301
  • /3

    $585,000

    • 2 Beds
    • 2 Baths
    • 1,775 Sq Ft

    24 Dogwood Dr, Brattleboro, VT 05301

    BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

    Dan Normandeau Berkley & Veller Greenwood Country

    24 Dogwood Dr, Brattleboro, VT 05301
  • /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
  • /59

    $1,125,000 Sold Sep 10, 2025

    • 4,503 Sq Ft
    • $250/SF
    • 15 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2025

    133 Howes Loop, Wilmington, VT 05363

    Just completed in July 2025, this striking 4-bedroom, 4-bathroom mountain modern home offers over 4,000 square feet of thoughtfully designed living space perched in the desirable Chimney Hill community in Wilmington, Vermont. Set on a 1 acre lot surrounded by mature trees, the home captures a glimpse of the Green Mountains and offers direct access to year-round recreation.Step inside to soaring

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    133 Howes Loop, Wilmington, VT 05363
    • /31

      Est $380,601 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,014 Sq Ft

      6 Timberview Rd, Dover, VT 05356

      6 Timberview Rd, Dover, VT 05356

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