Cheap homes for sale & real estate in Windham County, VT

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ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
This affordable Dummerston home is tucked away on 11 private acres. Built with personal privacy in mind, the primary bedroom is on one end and the other 2 bedrooms and bath are at the other, eliminating hallways and adding to the living area. Warm yourself and save on fuel with the large pellet stove in the living room. Abundant light with the picture window in the front and skylight over the work area in the kitchen. Huge eat in kitchen with tons of cabinets and good baking space. School is right around the corner, minutes to the Coop! Seller must find a place to move and is actively searching. Schedule showing the house is 10 am till 130 pm Monday-Thursday. Saturday morning 9 to 1. No Su

$325,000

3 beds2 baths1,232 sq ft

12 Autumn Gem Dr, Dummerston, VT 05301

11 acre lot • Built 2007 • Listed 116 days

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Dual charming updated cottages located conveniently between Mount Snow and Stratton with easy access off a paved public road for peace of mind and tremendous rentability. The current owners have lovingly updated these 2 cape style homes. One partially burned down and has been completely rebuilt and just completed. That larger home features an open concept kitchen and dining area, large great room with new kitchen and full bath, main floor bedroom and upstairs loft bedroom, large mudroom area for gear storage and laundry. The second cottage has a full open concept floor plan with gas fireplace, dining area, and kitchen with breakfast bar, a full bath, and two bedrooms upstairs. Great storage

$350,000

4 beds2 baths1,830 sq ft

4850 Route 100, Wardsboro, VT 05355

Open concept kitchen • Gas fireplace • Main floor bedroom

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. The building features a desirable unit mix with two 2-bedroom, 1-bath apartments and two 1-bedroom, 1-bath apartments. Recent improvements include a freshly painted exterior in 2025 and bathroom renovations completed in 2023, reflecting pride of ownership and minimizing near-term maintenance. Located in vibrant Brattleboro, tenants enjoy easy access to the town’s eclectic mix of restaurants, coffee shops, galleries, and local events, along with convenient access to Interstate 91 and nearby outdoor recreation. Known for its strong sense of community and thriving arts s

$422,000

6 beds4 baths3,756 sq ft

820 Western Ave, Brattleboro, VT 05301

Easy access • Outdoor recreation • Bathroom renovations

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Simple but elegant! Historic posts and wonderful beams define the magnificent open concept, giving visual shape and creating traditional options or whimsical uses for your new lifestyle. High ceilings and huge windows create a celebration of light, complementing the glowing antique floors magical in combination and truly beautiful. A home, an artist loft. .. so many uses, so unique, so inspiring. .. A Joy to own.

$255,000

1 bed1 bath1,320 sq ft

116 Birge St #2, Brattleboro, VT 05301

$220 HOA • Built 1890 • Listed 86 days

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Looking for an easy escape to the mountains? This furnished 2-bedroom mobile home sits right on the banks of the West River in West River Park—an ideal spot for seasonal living in Southern Vermont. The park has 23 sites and allows homeowners to stay up to 6 months each year, making it a great option for summer adventures or a winter ski base or, a little bit of both! Stratton is just 20 minutes away, and Mount Snow about 30, so you're never far from the slopes. In warmer months, enjoy fishing, swimming, or hiking nearby. The home has seen several recent updates, including new windows, a new chimney, oil tank, outdoor storage shed, and a propane stove for that cozy cabin feel. Park ren

$63,000

2 beds1 bath672 sq ft

2022 Route 30, Jamaica, VT 05343

Propane stove • Easy access • Seasonal living

Property at 1511 E Dover Rd, Wardsboro, VT 05355, 1 bed, 1 bath

$334,000

1 bed1 bath800 sq ft

1511 E Dover Rd, Wardsboro, VT 05355

Property at 8F Dover Green Loop Unit 8F, West Dover, VT 05356, 3 beds, 2 baths

$325,000

3 beds2 baths1,248 sq ft

8F Dover Green Loop Unit 8F, West Dover, VT 05356

Property at 1041 Moss Hollow Rd, Brattleboro, VT 05301, 1 bed, 1 bath

$250,000

1 bed1 bath884 sq ft

1041 Moss Hollow Rd, Brattleboro, VT 05301

Property at 19 Canal St, Brattleboro, VT 05301, 9 beds, 4 baths

$399,000

9 beds4 baths3,286 sq ft

19 Canal St, Brattleboro, VT 05301

Property at 343 Haystack Rd, Wilmington, VT 05363, 7 beds, 5 baths

$420,000

7 beds5 baths3,518 sq ft

343 Haystack Rd, Wilmington, VT 05363

Property at 555 VT route 9, Wilmington, VT 05363, 3 beds, 2 baths

$439,990

3 beds2 baths1,850 sq ft

555 VT route 9, Wilmington, VT 05363

Property at 34 Main St, Wardsboro, VT 05355, 3 beds, 3 baths

$325,000

3 beds3 baths1,750 sq ft

34 Main St, Wardsboro, VT 05355

Property at 3185 Higley Hill Rd, West Marlboro, VT 05363, 2 beds, 2 baths

$319,000

2 beds2 baths1,164 sq ft

3185 Higley Hill Rd, West Marlboro, VT 05363

Property at 52A Suntec Loop, West Dover, VT 05356, 3 beds, 3 baths

$385,000

3 beds3 baths1,768 sq ft

52A Suntec Loop, West Dover, VT 05356

Property at 136 Morningside Cmns, Brattleboro, VT 05301, 2 beds, 2.5 baths

$305,000

2 beds2.5 baths1,607 sq ft

136 Morningside Cmns, Brattleboro, VT 05301

Property at 429 VT Route 30, Newfane, VT 05345, 2 beds, 1 bath

$250,000

2 beds1 bath1,010 sq ft

429 VT Route 30, Newfane, VT 05345

Property at 15B Snow Tree Ln Unit Clovers B, West Dover, VT 05356, 3 beds, 2.5 baths

$449,000

3 beds2.5 baths1,842 sq ft

15B Snow Tree Ln Unit Clovers B, West Dover, VT 05356

Property at 1192 Chapel Hill Rd, Whitingham, VT 05361, 3 beds, 2 baths

$309,000

3 beds2 baths1,840 sq ft

1192 Chapel Hill Rd, Whitingham, VT 05361

Property at 39 Brookside Dr #7, Brattleboro, VT 05301, 1 bed, 1 bath

$135,000

1 bed1 bath685 sq ft

39 Brookside Dr #7, Brattleboro, VT 05301

Property at 243 Newton Rd, Vernon, VT 05354, 3 beds, 2 baths

$347,000

3 beds2 baths1,392 sq ft

243 Newton Rd, Vernon, VT 05354

Property at 8E Dover Green Loop Unit 8E Dover Green Loop, West Dover, VT 05356, 3 beds, 2 baths

$289,000

3 beds2 baths1,248 sq ft

8E Dover Green Loop Unit 8E Dover Green Loop, West Dover, VT 05356

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

$425,000

4 beds3 baths2,345 sq ft

52 Ruth Way, Wilmington, VT 05363

Property at 137 Stratton Arlington Rd, West Wardsboro, VT 05360, 4 beds, 1.5 baths

$399,000

4 beds1.5 baths2,100 sq ft

137 Stratton Arlington Rd, West Wardsboro, VT 05360

Property at 319 River Rd S, Putney, VT 05346, 1 bed, 1 bath

$260,000

1 bed1 bath512 sq ft

319 River Rd S, Putney, VT 05346

Property at 6795 VT Route 100, Londonderry, VT 05148, 4 beds, 2 baths

$339,000

4 beds2 baths2,460 sq ft

6795 VT Route 100, Londonderry, VT 05148

Property at 550 S Main St, Brattleboro, VT 05301, 3 beds, 2 baths

$319,000

3 beds2 baths1,280 sq ft

550 S Main St, Brattleboro, VT 05301

Property at 102, Qtr 4 Grand Summit Way Unit 102, Qtr 4, West Dover, VT 05356, 1 bed, 1 bath

$18,000

1 bed1 bath589 sq ft

102, Qtr 4 Grand Summit Way Unit 102, Qtr 4, West Dover, VT 05356

Property at 1 Frog Holw, Wilmington, VT 05363, 3 beds, 2 baths

$349,000

3 beds2 baths1,200 sq ft

1 Frog Holw, Wilmington, VT 05363

Property at 49 High Point Dr Unit A-14, Stratton, VT 05155, 2 beds, 2 baths

$429,000

2 beds2 baths1,353 sq ft

49 High Point Dr Unit A-14, Stratton, VT 05155

Property at 733 Rt 121, Westminster, VT 05158, 7 beds, 5 baths

$389,000

7 beds5 baths3,460 sq ft

733 Rt 121, Westminster, VT 05158

Property at 8 Dorf Auf Radar Rd, Wilmington, VT 05363, 2 beds, 1 bath

$39,900

2 beds1 bath530 sq ft

8 Dorf Auf Radar Rd, Wilmington, VT 05363

Property at 88-90 Westminster St, Bellows Falls, VT 05101, 6 beds, 2.5 baths

$357,000

6 beds2.5 baths3,590 sq ft

88-90 Westminster St, Bellows Falls, VT 05101

Property at 9A Mountain Village Way #141, Mt Snow, VT 05356, 1 bed, 1 bath

$275,000

1 bed1 bath664 sq ft

9A Mountain Village Way #141, Mt Snow, VT 05356

Property at 36C N Access Rd #703, West Dover, VT 05356, 3 beds, 3 baths

$369,000

3 beds3 baths1,750 sq ft

36C N Access Rd #703, West Dover, VT 05356

Property at 16 Washington St, Brattleboro, VT 05301, 5 beds, 3 baths

$225,000

5 beds3 baths2,209 sq ft

16 Washington St, Brattleboro, VT 05301

Property at 5362 US Route 5, Westminster, VT 05158, 3 beds, 1 bath

$250,000

3 beds1 bath1,050 sq ft

5362 US Route 5, Westminster, VT 05158

Property at 2072 N Main St, Londonderry, VT 05148, 6 beds, 3 baths

$299,000

6 beds3 baths3,942 sq ft

2072 N Main St, Londonderry, VT 05148

Property at 39 Atwood St, Brattleboro, VT 05301, 3 beds, 2 baths

$320,000

3 beds2 baths1,152 sq ft

39 Atwood St, Brattleboro, VT 05301

Property at 29 First Ln #17, Wilmington, VT 05363, 4 beds, 3.5 baths

$428,000

4 beds3.5 baths2,015 sq ft

29 First Ln #17, Wilmington, VT 05363

Property at 2173 Route 8A, Whitingham, VT 05361, 4 beds, 2 baths

$225,000

4 beds2 baths2,000 sq ft

2173 Route 8A, Whitingham, VT 05361

Property at 442 McMillan Rd, Whitingham, VT 05361, 4 beds, 2 baths

$324,000

4 beds2 baths— sq ft

442 McMillan Rd, Whitingham, VT 05361

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Cheap Homes for Sale in Windham County

There are currently 247 cheap homes for sale in Windham County at a median listing price of $480K. 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 65 days. This map is refreshed with the newest listings in Windham County every 15 minutes.

In the past month, 76 homes have been sold in Windham County. In addition to houses in Windham County, there were also 85 condos, 0 townhouses, and 18 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 Sun Aug 30 2026 on the search page

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