Windham County, VT Homes

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  /46

  $449,999 Sold Jun 16, 2025

  • 1,438 Sq Ft
  • $313/SF
  • 15 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  1448 Cyrus Rd, Whitingham, VT 05361

  Welcome to your perfect escape. This home has been beautifully maintained by the owners for 34 years. It has 3-bedrooms and 2-bathrooms. The homes nestled on a sprawling 15.2 acres complete with private hiking and ATV trails, a tranquil pond just steps from your front door, and breathtaking sunrise views from the porch, along with a large horse barn that has been partially converted into a

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  1448 Cyrus Rd, Whitingham, VT 05361
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  /38

  Est $561,945 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,035 Sq Ft

  6 River Rd, Newfane, VT 05345

  6 River Rd, Newfane, VT 05345
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  /30

  $750,000

  • 3 Beds
  • 2 Baths
  • 2,198 Sq Ft

  340 Melendy Hill Rd, Londonderry, VT 05155

  340 Melendy Hill Road, South Londonderry, VT40 Acres | 3 Beds | 2 Baths | Expansive Barn | Mountain ViewsTucked away in the hills of South Londonderry, this charming three-bedroom, two-bath cabin offers the perfect balance of privacy, natural beauty, and quintessential Vermont living. Sited on 40 peaceful acres with sweeping mountain views, the property feels like a private

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  340 Melendy Hill Rd, Londonderry, VT 05155
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  /37

  $375,000 Sold Jun 16, 2025

  • 1,632 Sq Ft
  • $230/SF
  • 66 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1998

  146 Sherwood Cir, Brattleboro, VT 05301

  If you’re looking for privacy, space to roam, and the convenience of being just 3 miles from downtown Brattleboro, this charming Cape-style home is a must-see! Set on a beautifully landscaped 1.16-acre lot in a desirable neighborhood, this 3-bedroom, 1.5 bath home sits slightly elevated above the others, offering stunning mountain views and all-day natural sunlight. The open-concept kitchen and

  Kate Barry EXP Realty

  146 Sherwood Cir, Brattleboro, VT 05301
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  /40

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,996 Sq Ft

  141 River Rd, Newfane, VT 05345

  141 River Rd, Newfane, VT 05345
• 

  

  /39

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  156 Mountain View Rd, Wilmington, VT 05363

  This charming Cape-style home offers three bedrooms and two full baths across the first two floors, featuring bamboo hardwood floors throughout and abundant natural light. Upstairs bedrooms have built in dressers. The living room boasts a cozy gas fireplace and flows seamlessly into the open-concept kitchen and dining area. A MAJOR highlight is the deeded lake rights to the picturesque Lake

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  156 Mountain View Rd, Wilmington, VT 05363
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  /42

  $499,900 Sold Jun 16, 2025

  • 2,100 Sq Ft
  • $238/SF
  • 100 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1996

  38 Yeaw Rd, Dover, VT 05341

  Enjoy the beauty and serenity of Vermont from this lovely 3 bedroom, 2 bath secluded country home set back off the road on 1.93 acres with a circular drive. The home features: a Primary Suite on the second level with a sitting room/office area, spa tub, oversized walk-in closet and an additional finished storage space. There are two bedrooms and a guest bathroom on the first floor along with an

  Lisa Mirando Deerfield Valley Real Estate

  38 Yeaw Rd, Dover, VT 05341
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  /6

  Est $134,823 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft

  449 Vt Route 30, Newfane, VT 05345

  449 Vt Route 30, Newfane, VT 05345
• 

  

  /39

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,957 Sq Ft

  256 Potter Rd, Wardsboro, VT 05355

  Built with a decade of love and care, this custom 3-bedroom, 2-bath hybrid timber frame home showcases quality craftsmanship and a deep connection to nature. Designed with natural materials to harmonize with the surrounding landscape, this inviting home offers peace and comfort both inside and out. Fall asleep to the soothing sound of the river that flows the length of the property. The main

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  256 Potter Rd, Wardsboro, VT 05355
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  /43

  $490,000 Sold Jun 16, 2025

  • 1,204 Sq Ft
  • $407/SF
  • 239 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1982

  132 Pingree Park Ln, Londonderry, VT 05148

  The interior footprint of this home is over 3900 sq feet! The original 1200 finished sq feet is enhanced by an addition needing interior finishing only. The large main floor of the addition (595 sq ft) has top quality construction, lots of natural light and an open floor plan. The 595 sq ft space above will make a stunning primary suite. Situated on a lovely parcel of land you will find

  Alison Cummings Cummings & Co

  132 Pingree Park Ln, Londonderry, VT 05148
• 

  

  /37

  Est $339,973 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  458 Vt Route 30, Newfane, VT 05345

  458 Vt Route 30, Newfane, VT 05345
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  /32

  $539,000

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

  2B Queen Anne's Way Unit 2B, Dover, VT 05356

  Beautiful Kingswood townhouse ideally located between Mount Snow and Hermitage Club at Haystack Mountain. This Kingswood townhouse offers the perfect mountain getaway. The open-concept living area features vaulted ceiling and a stunning three-sided wood-burning fireplace with custom stone surround and wood mantle creating a warm, inviting atmosphere. Enjoy the well-appointed kitchen with center

  Monique White Deerfield Valley Real Estate

  2B Queen Anne's Way Unit 2B, Dover, VT 05356
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  /3

  $1,052,500 Sold Jun 13, 2025

  • 4,230 Sq Ft
  • $249/SF
  • 0 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2004

  28 Airport Rd, Dover, VT 05356

  Ideally situated between Mount Snow, Carinthia and the Hermitage Club, this custom-built home overlooks the Mount Snow Golf Club with winter views of Haystack and Mt. Snow ski trails. This turnkey home has direct access to snowmobiling and you can expand your winter fun with backyard access to snowshoeing, cross country skiing and sledding on the golf course directly behind the home. You enter

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  28 Airport Rd, Dover, VT 05356
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  /28

  Est $299,783 Not Listed For Sale

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

  55 Back St, Newfane, VT 05345

  55 Back St, Newfane, VT 05345
• 

  

  /31

  $499,000

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

  285 Chimney Hill Rd, Wilmington, VT 05363

  Contemporary retreat in the heart of Chimney Hill. Set on a double lot along a paved road offering the perfect balance of comfort, style and year round convenience. Located just minutes from Wilmington village, Lake Whitingham, Mount Snow and scenic trail that leads to the summit of Haystack Peak in the Green mountain National Forest. The bright, open concept interior is filled with natural

  Monique White Deerfield Valley Real Estate

  285 Chimney Hill Rd, Wilmington, VT 05363
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  /25

  $315,000 Sold Jun 13, 2025

  • 1,340 Sq Ft
  • $235/SF
  • 50 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1988

  71 Whetstone Dr, Brattleboro, VT 05301

  Tucked in a sweet newer neighborhood, this home is not to be missed. Perfect for one floor living and aging in place, but versatile enough for choosing an upstairs bedroom! There is a one car attached garage and sunny deck with a slider to the dining area. The open concept with a vaulted ceiling gives a spacious, light filled living area. Some tlc needed but well worth a painting party.

  Christine Lewis Brattleboro Area Realty

  71 Whetstone Dr, Brattleboro, VT 05301
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  /40

  Est $449,263 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,109 Sq Ft

  25 Woodlands Ln, Newfane, VT 05345

  25 Woodlands Ln, Newfane, VT 05345
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  /60

  $899,000

  • 5 Beds
  • 4.5 Baths
  • 5,000 Sq Ft

  42 Blackberry Ln, Jamaica, VT 05343

  Idyllic, Picturesque, Expansive, Vast Family Farm with outbuildings and Large Farmhouse! Known to some as Sweet Berry Farm the blueberries and blackberries are plentiful along with many other productive fruits trees, a grove of 20 mature apple trees with many over 30 years old, , flowers and veggies in the gardens. This location just off of Route 30 is perfect for ALL of your Vermont dreams and

  Steve Goldfarb Deerfield Valley Real Estate

  42 Blackberry Ln, Jamaica, VT 05343
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  /31

  $250,000 Sold Jun 13, 2025

  • 1,153 Sq Ft
  • $217/SF
  • 361 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1976

  82 Two Brook Dr, Wilmington, VT 05363

  This home is perfect if you like wood. The lot is loaded with trees and the house is a wood lovers dream. Neat and tidy, this location is a just a great spot for any home based activity oriented retreat. Ready to go for Ski Season, Summer, Fall activities. Close to 2 major ski areas, swimming and lake boating or fishing, golf, Green Mountain National Forest. Nearby access to snowmobile

  Tony Tribuno Skihome Realty

  82 Two Brook Dr, Wilmington, VT 05363
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  /35

  Est $650,992 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  365 Timson Hill Rd, Newfane, VT 05345

  365 Timson Hill Rd, Newfane, VT 05345

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