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

271 homes

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FLOOR PLAN

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Step into a piece of Jamaica Village history. Once home to the F. E. Smith Dry Goods, Ready-Made Clothing, and Grocery Store, this distinctive red-and-white building blends Greek Revival presence with Vermont farmhouse character and now serves as a year-round residence filled with history and personality. The classic façade features full-width double-decker porches, white picket railing, and bold corner pilasters. Inside, this C. 1860 building’s commercial past lives on in a dramatic great room with original built-in storefront shelving and drawer banks once used to display dry goods. Now a unique library, studio and sitting area, the space features wide-plank wood floors, expo

$249,000

3 beds2 baths2,062 sq ft

39 Pikes Falls Rd, Jamaica, VT 05343

Natural light • Year round residence • Exposed beams

NEW 6 HRS AGO

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
A once in a lifetime camp opportunity on beautiful Sunset Lake! One of only seven cottages on the entire lake, this special getaway offers peace, serenity, and the perfect spot to enjoy life alongside the local loons. With 75 feet of waterfront, a screened porch overlooking the lake, and a loft sleeping area, this cottage is ready for lake days and unforgettable summer memories. The kitchen features a refrigerator, stove top, and dishwasher, while a separate outbuilding offers additional storage and a 3/4 bathroom. Grab your kayaks, head down to the water, and enjoy the simple pleasures of summers at the lake for years to come!

$275,000

1 bed1 bath336 sq ft

311 Lake Rd, Marlboro, VT 05344

Separate outbuilding • Screened porch • Loft sleeping area

FLOOR PLAN

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
This charming 3 bedroom, 1 bathroom ranch in a quiet Dummerston neighborhood offers comfort, versatility, and plenty of indoor and outdoor space. The wide-open living area includes an updated kitchen, beautiful wood flooring, and ample natural light. A wood stove adds the perfect touch for cozy fall and winter evenings. There’s plenty of flexible space for hobbies, a home office, or whatever suits your needs. The basement features a photography darkroom, a partially finished bathroom, and great potential for additional finished living space. Outside, enjoy a spacious, level yard and a large deck perfect for relaxing or entertaining, along with an attached one-car garage. Just 5 minute

$349,000

3 beds1 bath1,741 sq ft

50 Sugar Maple Dr, East Dummerston, VT 05301

Large deck • Wood stove • Spacious level yard

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Welcome to this lovingly maintained country property situated on 5.5 acres in Whitingham, Vermont. Offering a wonderful combination of open pasture, wooded acreage, and privacy, this property has so much to offer. The two-story home has been thoughtfully cared for by its long-time owners and features abundant natural light throughout the main living level. A delightful sunroom provides additional living space with direct access to the deck, perfect for enjoying the peaceful surroundings. A walk-out basement adds flexible space with access to the front yard. Outside, you’ll find beautiful open fields, wooded areas, and a spacious two-story barn in excellent condition, complete with ele

$368,000

4 beds1.5 baths1,824 sq ft

1287 Wilmington Cross Rd, Whitingham, VT 05361

Open pasture • 5.5 acres • Sunroom

FLOOR PLAN

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Just right! All spiffed up, shinny and ready to move right in. Sweet aging in place home on one level, level back yard, and minutes from grocery stores, hospital and Memorial Park! Just starting out? 3 bedrooms gives you room for expansion, hobbies or an aging parent. This affordable home should go most programs, has lots of light, and is a perfect beginner home. Check it out and start a new chapter; leave the rentals behind and invest in your future!

$275,000

3 beds1 bath1,112 sq ft

43 Winter St, Brattleboro, VT 05301

Level back yard • 0.23 acre lot • Garage

Property at 19 View Rd, Wilmington, VT 05363, 3 beds, 2 baths

$335,000

3 beds2 baths1,400 sq ft

19 View Rd, Wilmington, VT 05363

Property at 105 School St, Whitingham, VT 05361, 3 beds, 1 bath

$199,000

3 beds1 bath1,400 sq ft

105 School St, Whitingham, VT 05361

Property at 286 Richards Rd, Grafton, VT 05146, 2 beds, 1.5 baths

$420,000

2 beds1.5 baths1,436 sq ft

286 Richards Rd, Grafton, VT 05146

Property at 139 Frost St, Brattleboro, VT 05301, 2 beds, 3 baths

$129,000

2 beds3 baths— sq ft

139 Frost St, Brattleboro, VT 05301

Property at 167 Silver Ln, Vernon, VT 05354, 2 beds, 2 baths

$339,000

2 beds2 baths2,412 sq ft

167 Silver Ln, Vernon, VT 05354

Property at 606 Franklin Rd, Vernon, VT 05354, 3 beds, 2 baths

$395,000

3 beds2 baths1,728 sq ft

606 Franklin Rd, Vernon, VT 05354

Property at 2747 Back Westminster Rd, Westminster, VT 05158, 2 beds, 1 bath

$65,000

2 beds1 bath750 sq ft

2747 Back Westminster Rd, Westminster, VT 05158

Property at 133 Valley Cemetery Rd, Athens, VT 05143, 2 beds, 1 bath

$139,000

2 beds1 bath672 sq ft

133 Valley Cemetery Rd, Athens, VT 05143

Property at 625 Black Mountain Rd, Brattleboro, VT 05301, 3 beds, 2 baths

$339,000

3 beds2 baths1,395 sq ft

625 Black Mountain Rd, Brattleboro, VT 05301

Property at 36 Ives Rd, Wilmington, VT 05363, 3 beds, 2 baths

$399,000

3 beds2 baths1,140 sq ft

36 Ives Rd, Wilmington, VT 05363

Property at 8 Winhall Station Rd, South Londonderry, VT 05155, 3 beds, 2 baths

$395,000

3 beds2 baths1,604 sq ft

8 Winhall Station Rd, South Londonderry, VT 05155

Property at 4054 Guilford Center Rd, Guilford, VT 05101, 3 beds, 1.5 baths

$375,000

3 beds1.5 baths2,094 sq ft

4054 Guilford Center Rd, Guilford, VT 05101

Property at 1107 Broad Brook Rd, Guilford, VT 05301, 3 beds, 2.5 baths

$148,000

3 beds2.5 baths2,376 sq ft

1107 Broad Brook Rd, Guilford, VT 05301

Property at 3 Lightning Ledge Way, Wilmington, VT 05363, 5 beds, 2.5 baths

$289,900

5 beds2.5 baths1,700 sq ft

3 Lightning Ledge Way, 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 135 Winterbell Dr, East Dummerston, VT 05346, 3 beds, 2.5 baths

$389,000

3 beds2.5 baths2,108 sq ft

135 Winterbell Dr, East Dummerston, VT 05346

Property at 41 Stratton Hill Rd, Newfane, VT 05351, 2 beds, 1.5 baths

$299,000

2 beds1.5 baths1,300 sq ft

41 Stratton Hill Rd, Newfane, VT 05351

Property at 36 Pine St, Brattleboro, VT 05301, 3 beds, 1.5 baths

$295,000

3 beds1.5 baths1,406 sq ft

36 Pine St, Brattleboro, VT 05301

Property at 256 Trail Rd, Putney, VT 05346, 3 beds, 2 baths

$400,000

3 beds2 baths1,296 sq ft

256 Trail Rd, Putney, VT 05346

Property at 12 River Front Dr, Bellows Falls, VT 05101, 2 beds, 1 bath

$225,000

2 beds1 bath1,352 sq ft

12 River Front Dr, Bellows Falls, VT 05101

Property at 481 VT Rte 9 W, Wilmington, VT 05363, 4 beds, 1 bath

$299,000

4 beds1 bath1,650 sq ft

481 VT Rte 9 W, Wilmington, VT 05363

Property at 3531 Route 5, Westminster, VT 05158, 5 beds, 2 baths

$429,000

5 beds2 baths2,982 sq ft

3531 Route 5, Westminster, VT 05158

Property at 190 Depot St, Jamaica, VT 05343, 2 beds, 2.5 baths

$425,000

2 beds2.5 baths1,257 sq ft

190 Depot St, Jamaica, VT 05343

Property at 113 Happy Haven Rd, Wilmington, VT 05363, 5 beds, 3 baths

$419,000

5 beds3 baths1,875 sq ft

113 Happy Haven Rd, Wilmington, VT 05363

Property at 60 E Brook Xing Unit C-201, Wilmington, VT 05363, 3 beds, 1.5 baths

$359,000

3 beds1.5 baths1,450 sq ft

60 E Brook Xing Unit C-201, Wilmington, VT 05363

Property at 272 Shearer Hill Rd, Wilmington, VT 05363, 3 beds, 3 baths

$419,000

3 beds3 baths2,300 sq ft

272 Shearer Hill Rd, Wilmington, VT 05363

Property at 627 Abbott Rd, Brattleboro, VT 05301, 3 beds, 1.5 baths

$310,000

3 beds1.5 baths1,536 sq ft

627 Abbott Rd, Brattleboro, VT 05301

Property at 81 Scandia Village Rd, Wardsboro, VT 05360, 2 beds, 1 bath

$150,000

2 beds1 bath916 sq ft

81 Scandia Village Rd, Wardsboro, VT 05360

Property at 51 Burbee Ln, Townshend, VT 05353, 2 beds, 2 baths

$449,000

2 beds2 baths2,405 sq ft

51 Burbee Ln, Townshend, VT 05353

Property at 311 Dover Rd, Newfane, VT 05351, 3 beds, 1 bath

$289,000

3 beds1 bath1,322 sq ft

311 Dover Rd, Newfane, VT 05351

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 397 Route 121, Westminster, VT 05158, 4 beds, 2 baths

$374,900

4 beds2 baths2,400 sq ft

397 Route 121, Westminster, VT 05158

Property at 672 Huckle Hill Rd, Vernon, VT 05354, 2 beds, 1 bath

$310,000

2 beds1 bath1,367 sq ft

672 Huckle Hill Rd, Vernon, VT 05354

Property at 29 Morningside Cmns, Brattleboro, VT 05301, 2 beds, 1.5 baths

$189,500

2 beds1.5 baths966 sq ft

29 Morningside Cmns, Brattleboro, VT 05301

Property at 226 E West Rd, East Dummerston, VT 05346, 3 beds, 2 baths

$189,000

3 beds2 baths1,334 sq ft

226 E West Rd, East Dummerston, VT 05346

Property at 37 Poplar Ln, Vernon, VT 05354, 3 beds, 2.5 baths

$395,000

3 beds2.5 baths1,404 sq ft

37 Poplar Ln, Vernon, VT 05354

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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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