30,390

Windham County, VT Homes

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  • /3

    $560,000

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

    162 Buttonwood 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

    162 Buttonwood Dr, Brattleboro, VT 05301
  • /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
  • /32

    $372,500 Sold Sep 10, 2025

    • 1,556 Sq Ft
    • $239/SF
    • 84 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1985

    886 Brook Rd, Halifax, VT 05358

    ALL NEW ENGINEERED SEPTIC SYSTEM BEING INSTALLED IN AUGUST!Welcome to this charming and authentic log cabin in Southern Vermont, nestled among evergreens just off a paved road. This cozy retreat features true log construction throughout and offers a warm, inviting atmosphere perfect for year-round enjoyment. Inside, you’ll find a spacious living room with a wood stove, a large kitchen and

    Monica Sumner BHG Masiello Brattleboro

    886 Brook Rd, Halifax, VT 05358
    • /11

      Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 612 Sq Ft

      3 Fox Meadow Ln Unit 3F, Dover, VT 05356

      3 Fox Meadow Ln Unit 3F, Dover, VT 05356
  • /32

    $675,000

    • 3 Beds
    • 3 Baths
    • 2,216 Sq Ft

    12 Three Streams Way, Wilmington, VT 05363

    Beautiful 2006 chalet in the Chimney Hill community just a short drive from the Mount Snow Ski Resort and village Wilmington. This meticulous turn key home has been completely renovated and upgraded, and sits on a on a private lot in the Chimney Hill community on a quiet side road with access to snowmobile trails and winter views. Inside is a gorgeous great room space with vaulted ceilings and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    12 Three Streams Way, Wilmington, VT 05363
  • /32

    $4,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,080 Sq Ft
    • House for Rent

    194 Main St, Grafton, VT 05146

    VACATION RENTAL. In the center of Grafton Village find the refined Phebe Frost house. Beautifully maintained and thoughtfully decorated, spend some special time in Vermont! Lovely features include wood floors, double sided fireplace in living and dining, comfortable family room/den and stocked pantry. Delightful master suite on main floor and two additional bedrooms bookend a full bath upstairs.

    Jessica Landers Barrett and Valley Associates Inc.

    194 Main St, Grafton, VT 05146
  • /60

    $868,000 Sold Sep 09, 2025

    • 3,685 Sq Ft
    • $236/SF
    • 28 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1994

    155 Hillwinds N, Brattleboro, VT 05301

    Situated in Brattleboro’s premier, rural neighborhood, this much-loved home is a masterclass in thoughtful design, meticulous construction, & refined living. A grand dbl-door foyer welcomes you into a soaring entry hall that flows seamlessly into a sunken, dbl-height ceiling LR - complete w/ granite-surround FP, custom blt-ins, & crowned by a dramatic balcony overlook. Light pours in from every

    Dan Normandeau Berkley & Veller Greenwood Country

    155 Hillwinds N, Brattleboro, VT 05301
    • /2

      Not Listed For Sale

      • 1 Bed
      • 1 Bath

      5 Town Farm Rd, Town of Rockingham, VT 05101

      5 Town Farm Rd, Town of Rockingham, VT 05101
  • /3

    $585,000

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

    161 Buttonwood 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

    161 Buttonwood Dr, Brattleboro, VT 05301
  • /59

    $1,395,000 Sold Sep 08, 2025

    • 4,200 Sq Ft
    • $332/SF
    • 3 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2015

    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
    • /24

      Est $268,657 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,240 Sq Ft

      7 Hassey Bend Unit 16, Wilmington, VT 05363

      7 Hassey Bend Unit 16, Wilmington, VT 05363
  • /39

    $625,000

    • 5 Beds
    • 4 Baths
    • 3,748 Sq Ft

    58 Oak St, Brattleboro, VT 05301

    Come experience the elegance and charm of this stunning in-town retreat! Close to the town common and vibrant downtown Brattleboro—home to fine dining, galleries, quaint shops, and live music venues. Step inside the main house and be welcomed by a country kitchen featuring a large island, ideal for gatherings. The home exudes Victorian character with soaring ceilings, hardwood floors, and

    Rebecca Seymour Brattleboro Area Realty

    58 Oak St, Brattleboro, VT 05301
  • /23

    $150,000 Sold Sep 05, 2025

    • 810 Sq Ft
    • $185/SF
    • 4 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1972

    586 S Wardsboro Rd, Wardsboro, VT 05355

    This timeless cottage features an eat-in kitchen, a cozy living room, one full bathroom, and two bedrooms on the first level. Upstairs, there are two bonus rooms that offer additional space. There is fresh paint throughout and the bathroom has been updated with new flooring and a new vanity. Enjoy river frontage along the south Wardsboro brook which provides a picturesque backdrop for outdoor

    Michelle O'Neil Deerfield Valley Real Estate

    586 S Wardsboro Rd, Wardsboro, VT 05355
    • /22

      Est $947,128 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 3,227 Sq Ft

      389 Cobble Hill Rd, Londonderry, VT 05148

      389 Cobble Hill Rd, Londonderry, VT 05148
  • /60

    $599,000

    • 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 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 board, and

    Erica Reynolds Southern Vermont Realty Group

    794 White Rd, Windham, VT 05359
  • /35

    $439,000 Sold Sep 05, 2025

    • 2,339 Sq Ft
    • $188/SF
    • 8 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1985

    401 Crane Mountain Rd, Townshend, VT 05353

    Well maintained spacious log home located on 3 + acres in a beautiful country setting. Open concept living /dining area with woodburning stove, double siders open to a large wrap around deck with winter mountain views. This comfortable home offers a cozy eat - in kitchen with sweet access window to dining room. The flexible floorplan has a convenient first floor bedroom and bathroom. The second

    Janet Lucier Barrett & Valley Assoc. Inc

    401 Crane Mountain Rd, Townshend, VT 05353
    • /30

      Est $534,881 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,600 Sq Ft

      4 Robin Hill Rd, Townshend, VT 05353

      4 Robin Hill Rd, Townshend, VT 05353
  • /43

    $615,000

    • 3 Beds
    • 2.5 Baths
    • 2,720 Sq Ft

    58 Buckboard Dr, Dover, VT 05356

    58 Buckboard | Dover, VermontSet on 1.46 private acres with sweeping mountain views, this beautifully updated 3 bedroom, 3 bath home offers a perfect blend of modern style and Vermont warmth.Inside, the heart of the home is the newly renovated kitchen, featuring a center island with quartz countertops, stainless steel appliances, and open shelving. The kitchen flows seamlessly into the

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    58 Buckboard Dr, Dover, VT 05356
  • /20

    $245,000 Sold Sep 05, 2025

    • 2,168 Sq Ft
    • $113/SF
    • 18 Days On Market
    • Built 1915

    14-16 Valley St, Brattleboro, VT 05301

    Perfectly situated on a quiet street close to downtown, stores, and schools, this well cared for duplex is a rare opportunity for owner-occupants or investors alike. Each spacious unit offers 3 bedrooms and 1 full bath, with a host of updates and energy-efficient upgrades throughout. Many recent upgrades include Solar panels, Finished and insulated attics, Partially finished basements, Gas

    Claire Renaud Berkley & Veller Greenwood Country

    14-16 Valley St, Brattleboro, VT 05301
    • /6

      Est $86,185 Not Listed For Sale

      13 Edelweiss, Dover, VT 05356

      13 Edelweiss, Dover, VT 05356
  • /60

    $495,000

    • 6 Beds
    • 3 Baths
    • 3,954 Sq Ft

    430 Huckle Hill Rd, Vernon, VT 05354

    Perfect EXTENDED FAMILY OR IN-LAW set up!! This spacious and inviting property offers the perfect blend of privacy and comfort. Nestled in a peaceful wooded setting, surrounded by classic stone walls and a year-round stream, it provides the Vermont lifestyle you’ve been dreaming of. Inside, the main level features gleaming hardwood floors with radiant heat and an open-concept layout with vaulted

    Carol Slocum Keller Williams Realty Metro-Keene

    430 Huckle Hill Rd, Vernon, VT 05354
  • /46

    $65,000 Sold Sep 05, 2025

    • 1,271 Sq Ft
    • $51/SF
    • 48 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1998

    315, Qtr 1 89 Grand Summit Way, Dover, VT 05356

    Enjoy all the perks of slope-side living with no upkeep in this unique top-floor 2-bedroom, 2-bathroom quarter share suite at the Grand Summit Resort Hotel. This spacious condo is just one level below the penthouse, sleeps up to 10 people, and features a full kitchen, gas fireplace, and private deck with stunning views overlooking the ski slopes.The large primary suite offers a peaceful

    Patricia Fitzpatrick Skihome Realty

    315, Qtr 1 89 Grand Summit Way, Dover, VT 05356
    • /35

      Est $410,908 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 3,169 Sq Ft

      3796 Vt Route 30, Jamaica, VT 05343

      3796 Vt Route 30, Jamaica, VT 05343
  • /20

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    175 Sherwood Forest, Londonderry, VT 05148

    Nestled in the scenic beauty of Londonderry, Vermont, this delightful 3-bedroom, 2-bathroom home offers the perfect blend of comfort, convenience, and outdoor charm. With a thoughtfully designed layout that includes a bedroom and full bath on the main floor, this home is ideal for aging in place or accommodating guests.The heart of the home boasts an open living, dining, and kitchen area,

    Christiane Carroccio TPW Real Estate

    175 Sherwood Forest, Londonderry, VT 05148
  • /52

    $495,000 Sold Sep 05, 2025

    • 2,023 Sq Ft
    • $245/SF
    • 112 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1959

    6940 Coolidge Hwy, Guilford, VT 05301

    Located just north of the Massachusetts border, this home with two car detached garage is conveniently just 15 minutes from both Greenfield and Brattleboro.As you step inside to the mudroom you'll enter the coziest of kitchens radiating warmth and character. Featuring a wood stove, a stunning brick hearth with beehive oven, wooden beams adding rustic charm, while a cathedral ceiling keeps the

    Rebecca Seymour Brattleboro Area Realty

    6940 Coolidge Hwy, Guilford, VT 05301
    • /31

      Est $705,787 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
  • /29

    $514,900

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    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
  • /13

    $91,000 Sold Sep 04, 2025

    • 949 Sq Ft
    • $96/SF
    • 7 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1984

    7 Stonewall Dr Unit 60159.s07, Brattleboro, VT 05301

    This is a well cared for and improved affordable home. The airy open concept of the main space makes for a feeling of spaciousness. The primary bedroom has direct access to the full bath and laundry. The attached enclosed porch offers additional seasonal living space, The large corner lot offers good garden space and storage in the good sized storage shed.

    David Brown Berkley & Veller Greenwood Country

    7 Stonewall Dr Unit 60159.s07, Brattleboro, VT 05301
    • /40

      Est $2,005,776 Not Listed For Sale

      • 6 Beds
      • 6.5 Baths
      • 7,088 Sq Ft

      83 Overlook Dr, Dover, VT 05356

      83 Overlook Dr, Dover, VT 05356
  • /44

    $475,000

    • 4 Beds
    • 3 Baths
    • 3,314 Sq Ft

    76 Spruce St, Brattleboro, VT 05301

    Sweet! The perfect location...intown...backing up to the retreat trail system...and has a beautiful front porch and private back deck. This has been a much loved home, ready for a new generation to create their own music and harmony of life. The rooms are large, comfortable with lots of windows, real wood paneling reflecting the era, high ceilings, enough room to work from home (even an office

    Christine Lewis Brattleboro Area Realty

    76 Spruce St, Brattleboro, VT 05301
  • /33

    $182,000 Sold Sep 04, 2025

    • 1,000 Sq Ft
    • $182/SF
    • 80 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1968

    290 Old Mill Ln, Wilmington, VT 05363

    “The Camp” Are you looking for that special seasonal getaway? Look no further! This charming 1-bedroom on the main level and second bedroom upstairs sleeping loft is located in the beautiful town of Wilmington. Nestled in the woods, this cozy cabin offers a unique and special Vermont experience. Enjoy the covered front porch and large deck, perfect for entertaining friends and family. Just steps

    Richard Caplan Deerfield Valley Real Estate

    290 Old Mill Ln, Wilmington, VT 05363
    • /12

      Est $232,007 Not Listed For Sale

      • 1 Bed
      • 420 Sq Ft

      3709 Windham Hill Rd, West Townshend, VT 05359

      3709 Windham Hill Rd, West Townshend, VT 05359
  • /32

    $559,000

    • 3 Beds
    • 3 Baths
    • 2,080 Sq Ft

    9 Greer Ct, Wilmington, VT 05363

    Charming 2007 home with recent renovations nestled in the Chimney Hill community just a short drive from the Mount Snow ski resort, country village of Wilmington, and nearby lakes and amenities. This home sits on a private dead end parcel and has unique privacy and curb appeal. Inside you are treated to a large vaulted great room with expansive windows, exposed natural wood ceilings, and great

    Adam Palmiter Berkley & Veller Greenwood/Dover

    9 Greer Ct, Wilmington, VT 05363
  • /33

    $725,000 Sold Sep 03, 2025

    • 3,431 Sq Ft
    • $211/SF
    • 31 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 1974

    389 Howard Hill Rd, Londonderry, VT 05148

    Showing to start July 7th. The Octagon at Powder Mill: An Exceptional Mountain GetawayThis extraordinary modern home is a true gem, offering a perfect blend of natural light, expansive space, and architectural elegance. With panoramic windows framing awe-inspiring mountain vistas from every corner, this property showcases a unique design that masterfully balances aesthetics with practicality.

    Carrie Mathews Winhall Real Estate

    389 Howard Hill Rd, Londonderry, VT 05148
    • /5

      Est $160,813 Not Listed For Sale

      2 Johnson Hill Rd, Dover, VT 05356

      2 Johnson Hill Rd, Dover, VT 05356
  • /47

    $570,000 Open Sun 10AM - 12PM

    • 4 Beds
    • 2 Baths
    • 1,937 Sq Ft

    149 Dix Ln, Whitingham, VT 05361

    Open House Sunday, September 21, 10:00 to noon - Tucked away on a quiet, town-maintained dead end road this Vermont country homestead offers the perfect blend of charm, privacy, and practicality. Set on 34+ acres, this property has woodlands, pasture and hay fields that have supported a working farm with livestock for the past 5 years. This property is well suited for those seeking a working

    Sandy Reavill Real Broker LLC

    149 Dix Ln, Whitingham, VT 05361
  • /10

    $54,000 Sold Sep 03, 2025

    • Land
    • 0.25 Acre
    • $216,000 per Acre
    • 387 Days On Market

    203 Fairview St, Brattleboro, VT 05301

    In-town lots are few and far between these days but are such a great option! Design your own low inpact, energy efficient home, your dream home! This is your spot! This neighborhood is friendly and convenient to schools, Memorial Park, shopping, hospitals and just minutes to 91. The .25 acre lot is cleared and ready to go with easy access to town water and sewer. House site is set back from the

    Rebecca Seymour Brattleboro Area Realty

    203 Fairview St, Brattleboro, VT 05301
    • /13

      Not Listed For Sale

      0 Middle Rd, Brattleboro, VT 05301

      0 Middle Rd, Brattleboro, VT 05301
  • /58

    $568,000

    • 3 Beds
    • 2 Baths
    • 2,066 Sq Ft

    192 Western Ave, Brattleboro, VT 05301

    Timeless 1855 classic with historic charm just minutes to downtown Brattleboro. Step back in time with this beautifully preserved home, offering a rare blend of vintage character and modern comfort. Featuring three bedrooms and two bathrooms, this home is perfect for those who appreciate craftsmanship and history. Thoughtful updates complement the historic features without compromising

    Claire Renaud Berkley & Veller Greenwood Country

    192 Western Ave, Brattleboro, VT 05301
  • /41

    $850,000 Sold Sep 02, 2025

    • 1,768 Sq Ft
    • $481/SF
    • 10 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1999

    2 Stratton Springs Rd Unit 2, Stratton, VT 05360

    Welcome to the exceptional Resort Townhome community of Stratton Springs with private shuttle, Stratton Sports Center access and convenient location near the Stratton Mountain Resort Village and lifts. These upscale floor plans offer a multi level great room with 2 story ceilings, walls of windows with natural light and commanding fireplace. The second level gourmet kitchen and dining area

    Kim Morgan-Wohler Wohler Realty Group

    2 Stratton Springs Rd Unit 2, Stratton, VT 05360

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