2,052

Windham, VT Homes

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  • /60

    $599,000

    • 3 Beds
    • 2 Baths
    • 3,000 Sq Ft

    121 Dover Hill Rd, Dover, VT 05341

    Priced to sell! Now priced at $599,000.This is your rare chance to own a versatile 5-acre retreat just minutes from Mount Snow, ready for fall foliage season, winter skiing, or year-round rental income. Whether you're dreaming of a second home, short-term rental, or homestead, this updated Vermont mini-farm delivers. A small barn with paddocks, a classic sugarhouse, vibrant gardens, and raspberry

    Nick Sicard EXP Realty

    121 Dover Hill Rd, Dover, VT 05341
  • /39

    $535,000 Sold Aug 14, 2025

    • 2,364 Sq Ft
    • $226/SF
    • 23 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1795

    408 Dover Rd, South Newfane, VT 05351

    This 1790's classic colonial farmhouse offers the ideal country setting in a small New England village location. Spacious rooms provide a gracious yet relaxed environment. The first floor offers the primary bedroom and living room - each with its own propane fireplace, updated chef's kitchen, and 3/4 bath. The dining room features floor to ceiling sliding French doors leading to a large deck

    David Brown Berkley & Veller Greenwood Country

    408 Dover Rd, South Newfane, VT 05351
    • /11

      Est $312,038 Not Listed For Sale

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

      48 Loop Rd, Newfane, VT 05345

      48 Loop Rd, Newfane, VT 05345
  • /60

    $565,000

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    7 Grassy Brook Rd, Brookline, VT 05345

    Welcome to The River House—a completely renovated, turn-key escape located directly on the scenic West River, complete with its own private beach. Whether you’re seeking a peaceful getaway, a year-round residence, or an investment property with proven short-term rental history, this home checks every box. Inside, the property has been thoughtfully updated from top to bottom: all-new flooring,

    Flex Realty Group Flex Realty

    7 Grassy Brook Rd, Brookline, VT 05345
  • /16

    $80,000 Sold Aug 14, 2025

    • Land
    • 10 Acres
    • $8,000 per Acre
    • 48 Days On Market

    Lot 4 North St, Dover, VT 05431

    Discover the perfect Vermont retreat on this 10.00 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape.Whether you

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 4 North St, Dover, VT 05431
    • /21

      Est $305,485 Not Listed For Sale

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

      443 Dover Rd, Newfane, VT 05351

      443 Dover Rd, Newfane, VT 05351
  • /26

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    78 Taft Brook Rd, East Dover, VT 05341

    Lovely country home that is being offered for the first time in 52 years. This special spot is 2 acres just off the Taft Brook in East Dover, a short drive from the Mount Snow ski resort, village of Wilmington, and Brattleboro. Enjoy complete privacy off the quiet country road, with beautiful landscaping, perennial gardens, natural stone work, level yard space, and direct access to walking and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    78 Taft Brook Rd, East Dover, VT 05341
  • /40

    $462,000 Sold Aug 08, 2025

    • 1,894 Sq Ft
    • $244/SF
    • 5 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1930

    34 Wiswall Hill Rd, Newfane, VT 05345

    BEST AND FINAL OFFERS DUE BY THURSDAY JULY 3rd at 9:00 AMThis country charmer blends the warmth and character of an antique cottage with tasteful modern updates for the perfect balance. Rich in personality, the home features exposed beams, brick hearths, wood floors, high ceilings, built-in bookshelves and dresser drawers, cozy corners, and spacious gathering areas. Just a few steps up from

    Jacki Murano Southern Vermont Realty Group

    34 Wiswall Hill Rd, Newfane, VT 05345
    • /33

      Est $225,326 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
  • /31

    $556,000

    • 3 Beds
    • 2 Baths
    • 1,522 Sq Ft

    174 Whites Hill Rd, Dover, VT 05356

    Nestled amidst over 20 acres of pristine land, this Moosehead log home offers the perfect blend of privacy and breathtaking views. Imagine living without the burden of an electric bill, as this property is equipped with a complete solar power system and a backup generator, ensuring you have all the modern conveniences while embracing a sustainable lifestyle.Whether you're working remotely

    Regina Perrotto Skihome Realty

    174 Whites Hill Rd, Dover, VT 05356
  • /40

    $270,000 Sold Aug 06, 2025

    • 1,240 Sq Ft
    • $218/SF
    • 81 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1930

    311 Dover Rd, Williamsville, VT 05362

    Charming Vermont home with 3 spacious bedrooms, and a bonus room with plenty of potential! With a first floor bedroom, bathroom and two bedrooms upstairs, this home can work well for most lifestyles and stages of life. The bonus room offers a tremendous amount of space that can be used as an office, yoga space, playroom or even converted into a bathroom to offer the perfect primary en-suite bath.

    Prema Fitzpatrick Skihome Realty

    311 Dover Rd, Williamsville, VT 05362
    • /27

      Est $175,674 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 998 Sq Ft

      1277 Vt Route 30, Townshend, VT 05353

      1277 Vt Route 30, Townshend, VT 05353
  • /59

    $795,000

    • 2 Beds
    • 2 Baths
    • 2,190 Sq Ft

    85 Browns Rd, Newfane, VT 05345

    Timeless 1780 Colonial on 80 Acres with Modern Sustainability- A Rare Historic Gem! Own a piece of American history with this stunning circa 1780 Colonial home, set on 80 serene acres of meadows and forest. Featuring 2 bedrooms plus a dedicated bedroom/office ,2 full bathrooms, and over two centuries of character, this historic property offers unmatched charm- now enhanced with energy-efficient

    Janet Lucier Barrett & Valley Assoc. Inc

    85 Browns Rd, Newfane, VT 05345
  • /2

    $80,000 Sold Aug 01, 2025

    • 1,413 Sq Ft
    • $57/SF
    • 245 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1990

    100 Legion Rd, Newfane, VT 05345

    Take a trip back in time when it was easy to build your own home, create a light filled environment, and just sit on the deck with something to sip! Recapture the little bit of country living you are looking for by finishing the project started by someone with a dream! There is a huge kitchen with beautiful island counter top, 2 modest bedrooms, a huge living room with a cathedral ceiling for

    Christine Lewis Brattleboro Area Realty

    100 Legion Rd, Newfane, VT 05345
    • /40

      Est $483,618 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 4,024 Sq Ft

      129 Adams Hill Rd Unit 27, South Newfane, VT 05351

      129 Adams Hill Rd Unit 27, South Newfane, VT 05351
  • /44

    $645,000 Under Contract

    • 2 Beds
    • 1.5 Baths
    • 1,530 Sq Ft

    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
  • /38

    $109,000 Sold Jul 30, 2025

    • 1,400 Sq Ft
    • $78/SF
    • 6 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1938

    16 Jones Hill Rd, Newfane, VT 05362

    Property being sold 'as is', conveyed with clean title.Seller has not occupied property, so no disclosures are available.Dwelling does have 'good bones', garage is worthless.“This property is eligible under the Freddie Mac First Look Initiative through 07/26/2025.

    Robert Balewicz Evergreen Realty of Vermont

    16 Jones Hill Rd, Newfane, VT 05362
    • /34

      Est $545,893 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,208 Sq Ft

      112 Kent Rd, Wardsboro, VT 05355

      112 Kent Rd, Wardsboro, VT 05355
  • /16

    $139,000

    • Land
    • 3.48 Acres
    • $39,943 per Acre

    Lot 5 Hope Rd, Newfane, VT 05345

    Buildable Acreage with permits in place on the West River! This is your chance to own a true waterfront lot with clearing, underground power already in place, a 4-bedroom septic permit, and ample river frontage to call your own. Build your dream home on this private cul-de-sac with only 4 other property owners ( currently 2 other homes). Step out your back door with your swimsuit on and your

    Jacki Murano Southern Vermont Realty Group

    Lot 5 Hope Rd, Newfane, VT 05345
  • /17

    $25,000 Sold Jul 18, 2025

    • Land
    • 2.01 Acres
    • $12,438 per Acre
    • 30 Days On Market

    8 Brickyard Rd, Dover, VT 05341

    Escape to the Green Mountains and embrace the simple life on this 2-acre parcel tucked away at the end of a quiet public road in East Dover. Surrounded by forest and fresh mountain air, this peaceful setting offers the perfect spot for your rustic cabin or off-grid retreat. A structure remains on site, ready to be cleared to make way for your vision. Utilities are in place although no soil

    Chad Lackey Deerfield Valley Real Estate

    8 Brickyard Rd, Dover, VT 05341
    • /40

      Est $480,765 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft

      41 Pine Acres Rd, Townshend, VT 05353

      41 Pine Acres Rd, Townshend, VT 05353
  • /47

    $399,000 Open Mon 10AM - 12PM

    • 3 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    398 Vermont 30, Newfane, VT 05345

    3BD/3BA true log home on 2 acres with a grand main level that is open and light-filled. Soaring ceilings, wood floors, a country kitchen with farmhouse sink and gas range, dining area, pellet stove, and a half bath with laundry. The main floor also features a spacious primary suite with large closet space and a luxurious bath highlighted by a slate walk-in rain shower. Upstairs are two spacious

    Jacki Murano Southern Vermont Realty Group

    398 Vermont 30, Newfane, VT 05345
  • /39

    $565,000 Sold Jul 17, 2025

    • 2,252 Sq Ft
    • $251/SF
    • 126 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1995

    60 Robbins Rd, Dover, VT 05341

    Set on nearly 12 acres of rolling lawn and lush gardens, this bright and sunny Cape blends charm, comfort, and space to unwind. The open-concept living area is bathed in natural light, with large windows framing the beauty of the outdoors. The updated kitchen features a spacious island, stainless steel appliances, and a gas range—perfect for cooking and entertaining. The first-floor primary suite

    Patrice Schneider Southern Vermont Realty Group

    60 Robbins Rd, Dover, VT 05341
    • /16

      Est $385,490 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,325 Sq Ft

      964 State Forest Rd, Townshend, VT 05353

      964 State Forest Rd, Townshend, VT 05353
  • /22

    $349,000

    • 4 Beds
    • 1.5 Baths
    • 1,404 Sq Ft

    696 S Wardsboro Rd, Wardsboro, VT 05355

    Priced to Sell. Fabulous Southern Vermont Estate nestled between Mount Snow and Stratton Ski areas! You'll have Wardsboro Brook in your back yard & Grout pond down the street as well as hiking trails, Vast Appalachian Trail (AT) and long Trails. Plenty of back country outdoor experiences available all year round. They say Location is everything, this property has everything and More. Family room

    Kimberly Dubois Matson Keller Williams Realty

    696 S Wardsboro Rd, Wardsboro, VT 05355
  • /29

    $554,000 Sold Jul 16, 2025

    • 1,350 Sq Ft
    • $410/SF
    • 57 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1987

    103 Dover Hill Rd, East Dover, VT 05341

    Lovely custom home just outside the town of Dover, near the Mount Snow ski resort and village of Wilmington, and near Lake Whitingham, with easy access near a paved town road. This cozy Vermont retreat sits on 14+ acres with established walking trails, a large pond, perennial landscaping, gorgeous stone walls, and more. The custom home is being offered by the original owners and features a large

    Adam Palmiter Berkley & Veller Greenwood/Dover

    103 Dover Hill Rd, East Dover, VT 05341
    • /33

      Est $280,117 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,186 Sq Ft

      60 Riverdale Rd, Townshend, VT 05353

      60 Riverdale Rd, Townshend, VT 05353
  • /13

    $79,500

    • Land
    • 3.50 Acres
    • $22,714 per Acre

    0 Dover Rd Unit 5054979, Newfane, VT 05345

    Welcome to your future home in the heart of a picturesque Vermont village! These exquisite land lots, thoughtfully designed by the architect-owner, offer a unique opportunity to build your dream home in a setting that perfectly captures the quintessential charm of small-town Vermont. Each lot is meticulously planned to adhere to the timeless "Vermont Vernacular" style, ensuring that your new

    Keith Nowak Four Seasons Sotheby's Int'l Realty

    0 Dover Rd Unit 5054979, Newfane, VT 05345
  • /12

    $19,999 Sold Jul 15, 2025

    • Land
    • 2.00 Acres
    • $10,000 per Acre
    • 14 Days On Market

    14 Brickyard Rd, Dover, VT 05341

    Beautiful hillside parcel less than ten minutes from Mount Snow but outside the direct path of heavy tourist traffic. Brickyard Road is a winding packed-gravel road dotted sparsely with homes for full-time Dover residents, each with plenty of land and privacy.From the roadside the topography dips down about 5 feet, then quickly comes to a much more gradual slope which continues for

    David White OwnerEntry.com

    14 Brickyard Rd, Dover, VT 05341
    • /40

      Not Listed For Sale

      • 8 Beds
      • 6 Baths
      • 4,790 Sq Ft

      3031 Vt Route 30, Townshend, VT 05353

      3031 Vt Route 30, Townshend, VT 05353
  • /17

    $325,000

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft

    3021 Potter Rd, Wardsboro, VT 05355

    Set on two serene acres overlooking a tranquil neighboring pond, this inviting 4-bedroom, 2-bath home offers the quintessential Vermont lifestyle. Surrounded by expansive wildflower gardens, mature trees, and breathtaking natural beauty, this property is a private sanctuary with year-round appeal.Inside, the cozy and light-filled interior features warm wood accents, a spacious layout, and

    Erika Weisenburger Kenneth

    3021 Potter Rd, Wardsboro, VT 05355
  • /27

    $399,000 Sold Jul 15, 2025

    • 1,726 Sq Ft
    • $231/SF
    • 48 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1965

    16 Miller Ln, Newfane, VT 05362

    Nestled on a quiet country road, this delightful 3-bedroom, 2-bath home offers peace, privacy, and classic Vermont charm. Surrounded by nature and beautiful mature perennial gardens, this is the perfect place for those seeking a slower pace of life. Step inside to find a spacious and versatile first floor layout featuring a bonus room—perfect as a home office, playroom, or cozy family space. The

    Mike Masters Four Seasons Sotheby's Int'l Realty

    16 Miller Ln, Newfane, VT 05362
    • /36

      Est $355,130 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,481 Sq Ft

      1871 W Hill Rd, Townshend, VT 05353

      1871 W Hill Rd, Townshend, VT 05353
  • /21

    $159,000

    • 1 Bed
    • 1 Bath
    • 680 Sq Ft

    1771 Townshend Dam Rd, Townshend, VT 05353

    Embrace the simplicity of cabin living, tucked away on just over 2 peaceful acres, this charming country retreat offers a nice balance of comfort and nature. Inside, you’ll find a cozy one bedroom layout, with an additional den, perfect for overflow sleeping or an office area. The home is open concept kitchen/living/dining area, and a bath. The added antique charm of the potbellied wood stove

    Prema Fitzpatrick Skihome Realty

    1771 Townshend Dam Rd, Townshend, VT 05353
  • /2

    $210,000 Sold Jul 15, 2025

    • 1,619 Sq Ft
    • $130/SF
    • 412 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1820

    5 Baker Brook Rd, Newfane, VT 05362

    This unique 1820's home sits pretty by a babbling brook and just oozes old-world charm. Sit on the large porch and drift away to the sounds of the stream. Featuring 3 bedrooms and an office on the main floor this could be a great family home or vacation hideaway! With close proximity to ski resorts and endless hiking and biking, this charmer is ideally located. An extra 1/2 acre is also available

    Daire Gibney Barrett and Valley Associates Inc.

    5 Baker Brook Rd, Newfane, VT 05362
    • /40

      Est $567,697 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,895 Sq Ft

      128 Duke Rd, Williamsville, VT 05362

      128 Duke Rd, Williamsville, VT 05362
  • /38

    $1,750,000

    • 4 Beds
    • 3.5 Baths
    • 2,862 Sq Ft

    161 Depot Rd, Williamsville, VT 05362

    Perched high above the enchanting hills of Newfane, VT, lies a truly one-of-a-kind property. This meticulously crafted home offers an off-grid, private retreat with breathtaking views of the surrounding landscape. Constructed in 2003, the post and beam design incorporates wood and stone harvested from its expansive219-acre setting, showcasing a harmonious blend of nature and architecture. This

    Keith Nowak Four Seasons Sotheby's Int'l Realty

    161 Depot Rd, Williamsville, VT 05362
  • /44

    $500,000 Sold Jul 07, 2025

    • 3,588 Sq Ft
    • $139/SF
    • 40 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1840

    19 Grimes Hill Rd, Newfane, VT 05345

    Distinctive in authenticity & charm this captivating 1840’s farmhouse hasstunning grounds, consisting of rolling meadows, fields, a barn, & an adorable outbuilding. The 7 acres surround the property offer privacy and protection. This property has been nurtured by the family for decades with numerous blueberry bushes, a spring-fed pond, & collections of gardens. (complete list attached under

    Kristen Ziter Taylor Brattleboro Area Realty

    19 Grimes Hill Rd, Newfane, VT 05345
    • /18

      Est $290,385 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,800 Sq Ft

      254 Depot Rd, Williamsville, VT 05362

      254 Depot Rd, Williamsville, VT 05362
  • /8

    $35,000

    • Land
    • 5.00 Acres
    • $7,000 per Acre

    0 Ober Hill Rd, Townshend, VT 05353

    Escape to your own private piece of Vermont with this beautiful 5-acre sloping wooded property. Located off the beaten path, yet conveniently close to route 30, you’ll find a peaceful forest of mature Oak, Ash and Pine trees. Whether you're a camping enthusiast or seeking a serene hideaway, this land offers a spectacular setting. Property is accessed at the end of an old town road that is no

    Rebecca Hiam Southern Vermont Realty Group

    0 Ober Hill Rd, Townshend, VT 05353

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