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

271 homes

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ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Light-filled and full of cottage charm, this beautifully updated 2-bedroom, 1-bath home sits on 3.4 level acres with a shared pond, offering a peaceful country setting just minutes from the heart of Wilmington. Originally designed as a 3-bedroom home, the upper level has been roughed in and plumbed, providing an incredible opportunity to create a spacious primary ensuite, additional bedrooms, or expanded living space. The walkout basement features high ceilings and excellent potential for future finishing, while also offering convenient storage for tools, outdoor gear, and recreational toys. Outside, mature gardens add color and character throughout the seasons, while a quaint sugarhouse ad

$389,000

2 beds1 bath1,036 sq ft

456 Route 100, Wilmington, VT 05363

Mature gardens • Shared pond • Walkout basement

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Priced to sell, on the Hill, End of the Road, Double Lot, built in 2024, Attached Garage, 3-bedroom 2 baths, Primary Suite with Ensuite Bath, Woodstove, Gas Cook Stove, Furnished, and Move-in Ready! Start enjoying all the amenities Chimney Hill offers within its 1,200-Acre Campus. Truly the most complete All-Season Resort in the Deerfield Valley with its exclusive members-only Clubhouse located at 2,000' on the Hill, featuring year-round swimming, new hot tub, fitness room, arcade room, playroom, community room, fully equipped members kitchen, reading nook, après ski lounge, 3 tennis court areas plus basketball court, extensive multi-use trail system, snowmobiling, ice skating, pic

$449,000

3 beds2 baths1,200 sq ft

47 Upper Howes Rd Unit A-23, Wilmington, VT 05363

Move-in ready • Double lot • Woodstove

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Rustic Hunting Cabin on 1+/- Acres. Spring water supply and a holding tank for septic in place. Several sleeping areas including a loft. One full bathroom. Kitchen with stove, ,microwave, refrigerator, stove, pellet stove, wood stove, 2 mini splits, washer & dryer. Plan your weekend runaway now!

$219,000

3 beds1 bath1,136 sq ft

279 North St, East Dover, VT 05341

Kitchen with stove • Wood stove • Washer and dryer

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Investment opportunity! This beautiful ski country compound offers 3 potential streams of rental income, or a home where you can enjoy sweeping views of the West River Valley just minutes away from Magic Mountain skiing and a surprising array of amenities in Londonderry’s town center. A barn apartment over a garage with a 3/4 bath, and an upstairs and downstairs unit with a full bath each, are all equipped with their own kitchen and come with paying tenants. Keep the property in its current configuration, or combine the main house into one living area, with the barn as an in-law suite. A septic design exists for a subdivision of the property which, if the subdivision is obtained and

$375,000

5 beds3 baths1,440 sq ft

135 Overlook Dr, Londonderry, VT 05148

In-law suite • Barn apartment • Septic design

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Owners will consider reasonable offers. Private 2004 country chalet in the Chimney Hill community just outside the village of Wilmington. Hiking trails, snowmobile trail access, and convenient nearby snowmobile trailer parking, make this super convenient for the outdoorsy. This home sits on a rare double lot, just up from the beautifully renovated Chimney Hill clubhouse, Lake Whitingham, and Mount Snow ski resort, affording year round enjoyment. Inside features include a large open living space with vaulted ceiling, wood burning stove, large open kitchen and dining area, main floor primary suite, main floor guest bedroom and full tiled bath, den/tv loft, and second floor bunk room with half

$439,000

3 beds2.5 baths1,548 sq ft

28 Lightning Ledge Way, Wilmington, VT 05363

Renovated clubhouse • Double lot • Hiking trails

Property at 246 Mann Rd, Wilmington, VT 05363, 1 bed

$249,000

1 bed— baths468 sq ft

246 Mann Rd, Wilmington, VT 05363

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 2074 VT RT 30, Jamaica, VT 05343, 1 bed, 1 bath

$140,000

1 bed1 bath400 sq ft

2074 VT RT 30, Jamaica, VT 05343

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 2022 Route 30, Jamaica, VT 05343, 2 beds, 1 bath

$63,000

2 beds1 bath672 sq ft

2022 Route 30, Jamaica, VT 05343

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 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 219 High St #3, Brattleboro, VT 05301, 1 bed, 1 bath

$139,000

1 bed1 bath592 sq ft

219 High St #3, Brattleboro, VT 05301

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

$305,000

3 beds2 baths1,280 sq ft

550 S Main St, Brattleboro, VT 05301

Property at 33 Oak St, Brattleboro, VT 05301

$375,000

— beds— baths4,116 sq ft

33 Oak St, Brattleboro, VT 05301

Property at 12 Par Dr #12, Wilmington, VT 05363, 3 beds, 3.5 baths

$319,000

3 beds3.5 baths2,000 sq ft

12 Par Dr #12, Wilmington, VT 05363

Property at 2036 VT RT 30, Jamaica, VT 05343, 2 beds, 1 bath

$57,000

2 beds1 bath844 sq ft

2036 VT RT 30, Jamaica, VT 05343

Property at 5D Snow Mountain Vlg #124, Dover, VT 05356, 1 bed, 1 bath

$275,000

1 bed1 bath576 sq ft

5D Snow Mountain Vlg #124, Dover, VT 05356

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 33 W Main St, Wilmington, VT 05363, 1 bed, 2.5 baths

$425,000

1 bed2.5 baths2,076 sq ft

33 W Main St, 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 49 West Rd, Wilmington, VT 05363, 3 beds, 2 baths

$425,000

3 beds2 baths1,510 sq ft

49 West Rd, Wilmington, VT 05363

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 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 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 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 5 Reynolds Dr, Brattleboro, VT 05301, 5 beds, 3 baths

$284,000

5 beds3 baths2,360 sq ft

5 Reynolds Dr, Brattleboro, VT 05301

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 9F Brumms Way Unit 9F, West Dover, VT 05356, 2 beds, 2 baths

$384,900

2 beds2 baths1,250 sq ft

9F Brumms Way Unit 9F, West Dover, VT 05356

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

$375,000

7 beds5 baths3,460 sq ft

733 Rt 121, Westminster, VT 05158

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

Property at 204/206 Qtr 2 Grand Summit Way Unit 204/206 Qtr 2, West Dover, VT 05356, 1 bed, 2 baths

$22,500

1 bed2 baths771 sq ft

204/206 Qtr 2 Grand Summit Way Unit 204/206 Qtr 2, West Dover, VT 05356

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 274/76Qtr. 1 Grand Summit Way, West Dover, VT 05356, 2 beds, 2 baths

$52,000

2 beds2 baths1,098 sq ft

274/76Qtr. 1 Grand Summit Way, West Dover, VT 05356

Property at 40 Ellis Brook Rd, West Dover, VT 05356, 4 beds, 2 baths

$375,000

4 beds2 baths1,512 sq ft

40 Ellis Brook Rd, West Dover, VT 05356

Property at 27 Country Ct, Wilmington, VT 05363, 4 beds, 2 baths

$389,000

4 beds2 baths1,344 sq ft

27 Country Ct, Wilmington, VT 05363

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

$449,000

3 beds3 baths1,726 sq ft

4A Suntec Loop Unit 4A, West Dover, VT 05356

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 24 Antler Loop, West Dover, VT 05356, 3 beds, 2 baths

$450,000

3 beds2 baths1,943 sq ft

24 Antler Loop, West Dover, VT 05356

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Cheap Homes for Sale in Windham County

There are currently 271 cheap homes for sale in Windham County at a median listing price of $475K. 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 84 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 114 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 16 2026 on the search page

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