4 Bedroom homes for sale & real estate in Windham County, VT

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NEW 10 HRS AGO

ABOUT THIS HOME
4 Bedroom Homes for Sale in Windham County, VT
Nestled in the picturesque countryside of Jamaica, Vermont, this charming residence offers an idyllic retreat just a stone's throw away from renowned ski areas such as Stratton Mountain, Bromley, Magic Mountain, and Mount Snow. The property is situated on a private road, ensuring tranquility and seclusion, while boasting four bedrooms, bonus room on the 3rd floor and two and a half baths, complemented by a cozy fireplace that enhances the home's inviting atmosphere. The mountain view across the valley serve as a stunning backdrop, making it an ideal setting for nature enthusiasts. The proximity to Jamaica State Park provides ample opportunities for hiking and camping, while the West River T

$535,000

4 beds2.5 baths1,943 sq ft

98 Birch Ln, Jamaica, VT 05343

Private road • Townshend state park • Nearby ski resorts

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ABOUT THIS HOME
4 Bedroom Homes for Sale in Windham County, VT
Discover the quintessential Vermont country lifestyle on your own 80 acres in Townshend where timeless farmhouse charm meets exceptional versatility and beautifully maintained grounds. This inviting four-bedroom post and beam farmhouse has been impeccably cared for with many updates throughout, offering a wonderful blend of historic character, comfort, and modern convenience. Inside, warm and welcoming living spaces provide the perfect setting for gathering with family and friends, while the sunroom offers a peaceful place to relax and enjoy the beauty of the surrounding landscape in every season. The space provides endless possibilities, whether you envision a yoga or fitness studio, creat

$1,150,000

4 beds2.5 baths4,053 sq ft

1276 Windham Hill Rd, West Townshend, VT 05359

80 acre lot • Built 1805 • Listed 6 days

ABOUT THIS HOME
4 Bedroom Homes for Sale in Windham County, VT
LOCATION! This 4-bedroom, 1-bath home is located directly across from beautiful Harriman Reservoir and just outside the Village of Wilmington. A great opportunity to bring your vision in an unbeatable location. This home offers plenty of space and character, along with important updates including a new foundation installed in 1993 and new French drains recently installed for added peace of mind. Enjoy the convenience of being just outside downtown Wilmington, with its charming shops, restaurants, and local amenities, while having Harriman Reservoir right across the road for boating, swimming, fishing, and summer fun. Mount Snow is just a short drive away, offering skiing and year-round moun

$279,000

4 beds1 bath1,650 sq ft

481 VT Rte 9 W, Wilmington, VT 05363

New french drains • New foundation • Downtown wilmington

ABOUT THIS HOME
4 Bedroom Homes for Sale in Windham County, VT
IN THE HEART OF THE HAMLET that is South Londonderry, VT, sits this exquisitely charming 1820s home, where historic Vermont character meets thoughtful updates and remarkable future potential. From the moment you arrive, the curb appeal, spacious private lot, and classic architecture set the tone. Inside, freshly professionally refinished wood floors gleam alongside beautiful stained-glass windows, original woodwork, turned newel posts, period railings, and distinctive details that give this home a personality all its own. The updated kitchen brings a fresh feel to the heart of the home, while a slate-floor mudroom, wood and propane stoves, and generous living spaces add warmth and practical

$499,000

4 beds3 baths2,460 sq ft

215 Main St, South Londonderry, VT 05155

Period railings • Turned newel posts • Slate-floor mudroom

ABOUT THIS HOME
4 Bedroom Homes for Sale in Windham County, VT
Welcome to one of Guilford’s oldest houses. Built in 1796, this is a classic south-facing center chimney Cape, situated on 16.8 acres of mowed fields and wooded hillside terrain. This is one of those houses that the owners have taken good care of with many upgrades with an emphasis on preserving original features. The house has 4 Bedrooms, 2 ½ updated baths, kitchen with breakfast nook, dining room, front parlor and family room. The chimney in the main room has a large Rumford Fireplace with an original Bee Hive oven. There is also a mud room with storage and a covered welcoming stone porch. The properties’ several stone walls provide opportunities for flowers and gardeni

$550,000

4 beds2.5 baths2,523 sq ft

220 Hale Rd, Guilford, VT 05301

Center chimney cape • Original features • Bee hive oven

Property at 845 Hall Rd, Brattleboro, VT 05358, 4 beds, 3.5 baths

$799,000

4 beds3.5 baths3,598 sq ft

845 Hall Rd, Brattleboro, VT 05358

Property at 90 Big Bend Loop, Wilmington, VT 05363, 4 beds, 3 baths

$599,000

4 beds3 baths2,352 sq ft

90 Big Bend Loop, Wilmington, VT 05363

Property at 52 North Rd, Wilmington, VT 05363-1812, 4 beds, 2 baths

$325,000

4 beds2 baths1,856 sq ft

52 North Rd, Wilmington, VT 05363-1812

Property at 165 Stone Hollow Rd, Londonderry, VT 05148, 4 beds, 2.5 baths

$699,000

4 beds2.5 baths3,959 sq ft

165 Stone Hollow Rd, Londonderry, VT 05148

Property at 24 Mowrey Rd, Jamaica, VT 05343, 4 beds, 4 baths

$519,000

4 beds4 baths3,075 sq ft

24 Mowrey Rd, Jamaica, VT 05343

Property at 47 Adams St, Westminster, VT 05158, 4 beds, 1.5 baths

$200,000

4 beds1.5 baths1,792 sq ft

47 Adams St, Westminster, VT 05158

Property at 230 Valley View Rd, West Dover, VT 05356, 4 beds, 2 baths

$465,900

4 beds2 baths2,199 sq ft

230 Valley View Rd, West Dover, VT 05356

Property at 49 High Point Dr Unit A-13, Stratton, VT 05155, 4 beds, 3 baths

$795,000

4 beds3 baths2,400 sq ft

49 High Point Dr Unit A-13, Stratton, VT 05155

Property at 354 Orchard St, Brattleboro, VT 05301, 4 beds, 2.5 baths

$585,000

4 beds2.5 baths2,212 sq ft

354 Orchard St, Brattleboro, VT 05301

Property at 5735 VT Route 11, Londonderry, VT 05148, 4 beds, 3 baths

$450,000

4 beds3 baths2,320 sq ft

5735 VT Route 11, Londonderry, VT 05148

Property at 176 Brophy Ln, Londonderry, VT 05155, 4 beds, 2 baths

$475,000

4 beds2 baths1,816 sq ft

176 Brophy Ln, Londonderry, VT 05155

Property at 619 Main St, South Londonderry, VT 05155, 4 beds, 2.5 baths

$489,000

4 beds2.5 baths2,100 sq ft

619 Main St, South Londonderry, VT 05155

Property at 170 Townshend Rd, Grafton, VT 05146, 4 beds, 2 baths

$699,000

4 beds2 baths2,613 sq ft

170 Townshend Rd, Grafton, VT 05146

Property at 116 Teacher Rd, Jamaica, VT 05343, 4 beds, 2.5 baths

$549,000

4 beds2.5 baths2,359 sq ft

116 Teacher Rd, Jamaica, VT 05343

Property at 12 Encore Pl, West Dover, VT 05356, 4 beds, 3.5 baths

$799,000

4 beds3.5 baths2,272 sq ft

12 Encore Pl, West Dover, VT 05356

Property at 51A Suntec Loop, West Dover, VT 05356, 4 beds, 3 baths

$497,500

4 beds3 baths2,200 sq ft

51A Suntec Loop, West Dover, VT 05356

Property at 33 Carinthia Dr, Mt Snow, VT 05356, 4 beds, 4.5 baths

$899,000

4 beds4.5 baths3,100 sq ft

33 Carinthia Dr, Mt Snow, VT 05356

Property at 1161 Little Pond Rd, Londonderry, VT 05148, 4 beds, 3 baths

$645,000

4 beds3 baths2,740 sq ft

1161 Little Pond Rd, Londonderry, VT 05148

Property at 1 Lower Highlands Rd, West Dover, VT 05356, 4 beds, 2.5 baths

$749,900

4 beds2.5 baths2,600 sq ft

1 Lower Highlands Rd, West Dover, VT 05356

Property at 6 High Point Dr #401, Stratton, VT 05155, 4 beds, 3.5 baths

$865,000

4 beds3.5 baths2,133 sq ft

6 High Point Dr #401, Stratton, VT 05155

Property at 954 Boardman Loop, West Wardsboro, VT 05360, 4 beds, 3 baths

$545,000

4 beds3 baths1,860 sq ft

954 Boardman Loop, West Wardsboro, VT 05360

Property at 364 Houghtonville Rd, Grafton, VT 05146, 4 beds, 3.5 baths

$1,150,000

4 beds3.5 baths3,649 sq ft

364 Houghtonville Rd, Grafton, VT 05146

Property at 52 Ruth Way, Wilmington, VT 05363, 4 beds, 3 baths

$399,000

4 beds3 baths2,345 sq ft

52 Ruth Way, Wilmington, VT 05363

Property at 10A Grouse Ln Unit 10A, West Dover, VT 05356, 4 beds, 3 baths

$549,000

4 beds3 baths2,600 sq ft

10A Grouse Ln Unit 10A, West Dover, VT 05356

Property at 2068 S Wardsboro Rd, Wardsboro, VT 05355, 4 beds, 1 bath

$349,000

4 beds1 bath1,608 sq ft

2068 S Wardsboro Rd, Wardsboro, VT 05355

Property at 4 Signal Pine Rd, Putney, VT 05346, 4 beds, 2.5 baths

$724,900

4 beds2.5 baths6,232 sq ft

4 Signal Pine Rd, Putney, VT 05346

Property at 54 Williams St, Bellows Falls, VT 05101, 4 beds, 2 baths

$125,000

4 beds2 baths2,644 sq ft

54 Williams St, Bellows Falls, VT 05101

Property at 37 Stowe Hill Rd, Wilmington, VT 05363, 4 beds, 2.5 baths

$624,900

4 beds2.5 baths2,904 sq ft

37 Stowe Hill Rd, Wilmington, VT 05363

Property at 21A Queen Anne's Way Unit 21A, West Dover, VT 05356, 4 beds, 3 baths

$569,000

4 beds3 baths2,067 sq ft

21A Queen Anne's Way Unit 21A, West Dover, VT 05356

Property at 14 Mill Rd, West Dover, VT 05356, 4 beds, 2 baths

$524,500

4 beds2 baths2,100 sq ft

14 Mill Rd, West Dover, VT 05356

Property at 54 Main St, Grafton, VT 05146, 4 beds, 2.5 baths

$639,000

4 beds2.5 baths2,128 sq ft

54 Main St, Grafton, VT 05146

Property at 7 Yodeling Ln, West Dover, VT 05356, 4 beds, 4.5 baths

$839,000

4 beds4.5 baths3,696 sq ft

7 Yodeling Ln, West Dover, VT 05356

Property at 29 Stable Rd, Wilmington, VT 05363, 4 beds, 1 bath

$149,000

4 beds1 bath2,710 sq ft

29 Stable Rd, Wilmington, VT 05363

Property at 7 Lightning Ledge Way, Wilmington, VT 05363, 4 beds, 2 baths

$534,000

4 beds2 baths1,776 sq ft

7 Lightning Ledge Way, Wilmington, VT 05363

Property at 816 Black Bear Rd, Jamaica, VT 05343, 4 beds, 5.5 baths

$3,995,000

4 beds5.5 baths5,500 sq ft

816 Black Bear Rd, Jamaica, VT 05343

Property at 15 Boulder Ridge Dr Unit 15A, West Dover, VT 05356, 4 beds, 4 baths

$990,000

4 beds4 baths3,100 sq ft

15 Boulder Ridge Dr Unit 15A, West Dover, VT 05356

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4 Bedroom Homes for Sale in Windham County

There are currently 80 4 bedroom homes in Windham County. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windham County stay on the market for 83 days. This map is refreshed with the newest listings in Windham County every 15 minutes.

In the past month, 58 homes have been sold in Windham County. In addition to houses in Windham County, there were also 115 condos, 0 townhouses, and 17 multi-family units for sale in Windham County last month. Find your dream home in Windham County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Windham County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windham County. If you're looking to sell your home in the Windham County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windham County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Copyright 2026 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Fri Oct 30 2026 on the search page

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