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:
Property is being sold "as is where is" and does need some TLC. The house is set back off the road quite a bit for total privacy and there is a pond on the property. There is a one car garage, a full daylight basement, and a sun room. Sellers have given permission to encourage all offers. Property was originally listed for $450,000 but the sellers have reduced the price to $350,000. The tax map indicates that are 16.6 acres while the deed indicates that there are 15+/-.

$330,000

4 beds3.5 baths2,575 sq ft

3730 Route 100, Wardsboro, VT 05355

Sun room • Full basement • Pond on the property

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please, only fully qualified with either proof of funds or a bank rehab loan prequel letter. Pets, so flexibility is needed for showing.

$90,000

3 beds1 bath1,030 sq ft

93 Clark St, Brattleboro, VT 05301

Off street parking • Walk to downtown • Bit of yard

3D WALKTHROUGH

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
A beautiful property needing someone to either do a barn to house conversion or build new on a scenic spot toward the back of the field which overlooks the barns, field, and hills beyond. This was a dairy farm years ago, and the barn still has some stanchions in place. Not a property for anyone to move right into since it needs finishing. This is more suited to a cash sale or special financing. Brockway Mills is a lightly traveled paved road just a half mile or so from Route 103. About equal distance between the scenic towns of Chester and Bellows Falls, and Springfield hospital and shopping is minutes away. Skiing is not far away at Okemo, and it's only 10 minutes from I-91 exit 6! This pr

$249,900

2 beds1 bath— sq ft

2137 Brockway Mills Rd, Chester, VT 05101

Brockway mills gorge • Overlooks the barns • 13 acre lot

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
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 provides cozy heat for those colder nights. Ideal for Vermont weekend getaways or year round simplicity and surrounded by mature perennials, a lush open lawn, and classic New England stone walls, the outdoor space invites you to unwind by the fire pit or explore the nearby woods. Two spacious she

$149,000

1 bed1 bath680 sq ft

1771 Townshend Dam Rd, Wardsboro, VT 05355

Open concept kitchen • Metal roof • Fire pit

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Quarter share (deeded interval 3) ownership at the Grand Summit offers 13 weeks of vacation per year on a rotating schedule that can be used, rented, or traded as you desire. Experience the mountain resort lifestyle affordably!! This first floor (Unit 152) with a sleep four studio is 407 sq ft and has a Murphy bed in the living area, a kitchen/dining area, and a full bath. This unit is located on the valley side of the hotel & just down the hallway from the spa, ski locker, health club, and pool. Enjoy the best ski-in/out location with access to all year-round amenities, including valet parking, owner's private lounge, library, deck, a full-service gym with sauna, spa, steam room, out

$20,000

0 beds1 bath407 sq ft

152 Qtr 3 89 Grand Summit Way #152, Mt Snow, VT 05356

Full service gym • On site restaurant • Ski in out location

Property at 1587 Upper Holbrook Rd, Whitingham, VT 05361, 3 beds, 2.5 baths

$445,000

3 beds2.5 baths2,872 sq ft

1587 Upper Holbrook Rd, Whitingham, VT 05361

Property at 876 Route 100, Wilmington, VT 05363, 3 beds, 2 baths

$295,000

3 beds2 baths1,328 sq ft

876 Route 100, Wilmington, VT 05363

Property at 8 Happy Haven Rd, Wilmington, VT 05363, 3 beds, 2 baths

$299,000

3 beds2 baths1,632 sq ft

8 Happy Haven Rd, Wilmington, VT 05363

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

$220,000

3 beds1 bath1,050 sq ft

5362 US Route 5, Westminster, VT 05158

Property at 152 Our Rd, Putney, VT 05158, 2 beds, 2 baths

$425,000

2 beds2 baths1,386 sq ft

152 Our Rd, Putney, VT 05158

Property at 81 Parish Hill Rd, Newfane, VT 05351, 2 beds, 1 bath

$275,000

2 beds1 bath— sq ft

81 Parish Hill Rd, Newfane, VT 05351

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 10 Riverfront Dr, Bellows Falls, VT 05101, 2 beds, 2 baths

$275,000

2 beds2 baths1,440 sq ft

10 Riverfront Dr, Bellows Falls, VT 05101

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

$359,000

3 beds2 baths1,840 sq ft

1192 Chapel Hill Rd, Whitingham, VT 05361

Property at 48 Villager Loop, West Dover, VT 05356, 3 beds, 2 baths

$385,000

3 beds2 baths1,600 sq ft

48 Villager Loop, West Dover, VT 05356

Property at 2015 Vermont Route 30, Townshend, VT 05353, 5 beds, 2 baths

$335,000

5 beds2 baths1,944 sq ft

2015 Vermont Route 30, Townshend, VT 05353

Property at 528 VT Route 121, Windham, VT 05148, 3 beds, 2 baths

$375,000

3 beds2 baths1,520 sq ft

528 VT Route 121, Windham, VT 05148

Property at 76 Spruce St, Brattleboro, VT 05301, 4 beds, 3 baths

$425,000

4 beds3 baths3,314 sq ft

76 Spruce St, Brattleboro, VT 05301

Property at 6 Gates Lake Raponda Ln, Wilmington, VT 05363, 2 beds, 1.5 baths

$449,000

2 beds1.5 baths1,416 sq ft

6 Gates Lake Raponda Ln, Wilmington, VT 05363

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

$65,000

2 beds1 bath672 sq ft

2022 Route 30, Jamaica, VT 05343

Property at 49 West Rd, Wilmington, VT 05363, 3 beds, 2 baths

$449,000

3 beds2 baths1,510 sq ft

49 West Rd, Wilmington, VT 05363

Property at 696 S Wardsboro Rd, Wardsboro, VT 05355, 4 beds, 1.5 baths

$339,000

4 beds1.5 baths1,404 sq ft

696 S Wardsboro Rd, Wardsboro, VT 05355

Property at 715 Chase Rd, West Townshend, VT 05359, 4 beds, 2 baths

$425,000

4 beds2 baths3,300 sq ft

715 Chase Rd, West Townshend, VT 05359

Property at 1469 Higley Hill Rd, West Marlboro, VT 05363, 4 beds, 2 baths

$399,000

4 beds2 baths1,768 sq ft

1469 Higley Hill Rd, West Marlboro, VT 05363

Property at 164 Chestnut St, Brattleboro, VT 05301, 3 beds, 1 bath

$309,900

3 beds1 bath1,323 sq ft

164 Chestnut St, Brattleboro, VT 05301

Property at 1177 Western Ave, Brattleboro, VT 05301, 4 beds, 2 baths

$279,900

4 beds2 baths1,733 sq ft

1177 Western Ave, Brattleboro, VT 05301

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

$275,000

4 beds2 baths2,000 sq ft

2173 Route 8A, Whitingham, VT 05361

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

$449,000

3 beds3 baths1,768 sq ft

52A Suntec Loop, West Dover, VT 05356

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

$449,000

4 beds3.5 baths2,015 sq ft

29 First Ln #17, Wilmington, VT 05363

Property at 4850 Route 100, Wardsboro, VT 05355, 4 beds, 2 baths

$399,000

4 beds2 baths1,830 sq ft

4850 Route 100, Wardsboro, VT 05355

Property at 78-80 Central St, Brattleboro, VT 05301, 4 beds, 2 baths

$295,000

4 beds2 baths2,408 sq ft

78-80 Central St, Brattleboro, VT 05301

Property at 230, Qtr 2 Grand Summit Way Unit 230, Qtr 2, West Dover, VT 05356, 1 bed, 2 baths

$27,900

1 bed2 baths941 sq ft

230, Qtr 2 Grand Summit Way Unit 230, Qtr 2, West Dover, VT 05356

Property at 1950 N Main St, Londonderry, VT 05148, 7 beds, 4 baths

$430,000

7 beds4 baths3,551 sq ft

1950 N Main St, Londonderry, VT 05148

Property at 247 VT Route 100, Wilmington, VT 05363, 6 beds, 2 baths

$379,000

6 beds2 baths1,920 sq ft

247 VT Route 100, Wilmington, VT 05363

Property at 20 Newell Hl, West Wardsboro, VT 05360, 4 beds, 2 baths

$329,000

4 beds2 baths2,202 sq ft

20 Newell Hl, West Wardsboro, VT 05360

Property at 394 Haystack Rd #2, Wilmington, VT 05363, 2 beds, 1.5 baths

$249,900

2 beds1.5 baths1,059 sq ft

394 Haystack Rd #2, Wilmington, VT 05363

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

$315,000

5 beds3 baths2,209 sq ft

16 Washington St, Brattleboro, VT 05301

Property at 8577 VT Route 30 Unit H, Jamaica, VT 05343, 2 beds, 1 bath

$199,000

2 beds1 bath844 sq ft

8577 VT Route 30 Unit H, Jamaica, VT 05343

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

$399,000

4 beds2 baths— sq ft

442 McMillan Rd, Whitingham, VT 05361

Property at 77 Griswold Dr, Bellows Falls, VT 05101, 3 beds, 1 bath

$235,000

3 beds1 bath1,144 sq ft

77 Griswold Dr, Bellows Falls, VT 05101

Property at 121 Happy Haven Rd, Wilmington, VT 05363, 3 beds, 1.5 baths

$255,000

3 beds1.5 baths1,728 sq ft

121 Happy Haven Rd, Wilmington, VT 05363

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Cheap Homes for Sale in Windham County

There are currently 212 cheap homes for sale in Windham County at a median listing price of $489K. 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 100 days. This map is refreshed with the newest listings in Windham County every 15 minutes.

In the past month, 61 homes have been sold in Windham County. In addition to houses in Windham County, there were also 85 condos, 6 townhouses, and 16 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 2025 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 Sat Dec 06 2025 on the search page

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