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:
Tucked away along a quiet, town-maintained deadend road, this private 15-acre parcel offers a rare combination of seclusion, character, and natural beauty. Set high on a peaceful knoll, the property features an old homesite's stone foundation, open meadow areas, and several mature apple trees that hint at the land’s past, also a drilled well. A gentle babbling brook traces one boundary, adding to the tranquil setting and mountain-country charm. The driveway winds gradually upward to the homesite where the landscape opens to a mostly level field, an ideal setting for a future home, cabin, or retreat. With selective clearing, the property offers excellent potential for mountain views. B

$174,000

Land15.00 acres (lot)

491 Whitneyville Rd, Halifax, VT 05358

Open meadow areas • Drilled well

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Fantastic eastern views of NH mountains & valleys. A super roadway already exists, providing access to places around the 47 private acres. Several places to build, affording long range views & glorious sunrises. Perfect location for that magical place you've been waiting to build. Ski area resort amenities are a short drive right around the corner, while Brattleboro & the CT River Valley resources are just down the hill. Truly a convenient majestic site worthy and complementary of your new home!

$329,000

Land47.58 acres (lot)

0 Higley Hl, Dover, VT 05356

Long range views • Convenient site

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Affordable opportunities to own land in Southern Vermont are becoming increasingly hard to find. This 1.30+/- acre wooded parcel on Smead Road offers a gradual rise from the road, creating a private, natural setting to enjoy now or explore for the future. Conveniently located between Mount Snow and Stratton, the property is close to year-round recreation, including skiing, snowmobiling, hiking, mountain biking, fishing, kayaking, and the shops and restaurants of nearby Dover, Wardsboro, Wilmington, and Jamaica. Whether you're looking for a recreational retreat, an investment in Vermont land, or simply an affordable way to establish your own piece of the Green Mountains, this parcel is well

$20,000

Land1.30 acres (lot)

Smead Rd, Wardsboro, VT 05355

Wooded parcel • Close to hiking • Close to skiing

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Lovely pastoral parcel of land in Whitingham Vermont with mountain views. This parcel sits conveniently on the MA border for easy access into the Deerfield Valley or Heath area. The 45 acre parcel is about half pasture and half mature woodlands, with easy access of the quiet country road, old stone walls, views of the mountains to the west, and a serene setting.

$279,000

Land45.00 acres (lot)

0 Saddada Rd Lot 0, Whitingham, VT 05361

Quiet country road • Mature woodlands • Old stone walls

ABOUT THIS HOME
Cheap Home for sale in Windham County, VT:
Nestled just half a mile from the renowned Mount Snow Resort, this exquisite 4.50-acre property offers a remarkable opportunity to create your dream home in a prime location. With a cleared driveway and an essential permit already secured (Waste Water Permit for a mound wastewater disposal system and a Potable Water Permit for a drilled bedrock water supply), this lot is ready for development. The property is conveniently situated along Route 100, providing easy access to the towns of Dover and Wilmington, golf courses at Mount Snow and Haystack, and boating/kayaking at Harriman's Reservoir, Lake Raponda, and Grout Pond. A WW permit is secured for a 3-bedroom single-family residence, with e

$135,000

Land4.50 acres (lot)

0 Route 100, Dover, VT 05356

Waste water permit • Potable water permit • Picturesque setting

Property at 56 & 57 Boardman Loop, Wardsboro, VT 05355

$57,000

Land2.00 acres (lot)

56 & 57 Boardman Loop, Wardsboro, VT 05355

Property at 0 Rose Ln, Londonderry, VT 05148

$152,000

Land11.08 acres (lot)

0 Rose Ln, Londonderry, VT 05148

Property at 0 Huckle Hill Rd, Vernon, VT 05354

$70,000

Land2.01 acres (lot)

0 Huckle Hill Rd, Vernon, VT 05354

Property at 192 Pingree Park Ln, Londonderry, VT 05148

$135,000

Land2.19 acres (lot)

192 Pingree Park Ln, Londonderry, VT 05148

Property at Lot A Sweet Pond Rd Lot 1, Guilford, VT 05301

$165,000

Land1.90 acres (lot)

Lot A Sweet Pond Rd Lot 1, Guilford, VT 05301

Property at 9 Brown Rd, Wilmington, VT 05363

$149,000

Land16.74 acres (lot)

9 Brown Rd, Wilmington, VT 05363

Property at 925 Porcupine Ln Unit M-925, Wilmington, VT 05363

$60,000

Land0.59 acre (lot)

925 Porcupine Ln Unit M-925, Wilmington, VT 05363

Property at 69 Old Haven Ln, Putney, VT 05346

$100,000

Land2.50 acres (lot)

69 Old Haven Ln, Putney, VT 05346

Property at 00 Boynton Rd, Londonderry, VT 05148

$150,000

Land18.78 acres (lot)

00 Boynton Rd, Londonderry, VT 05148

Property at 000 Hinkley Brook Rd, Grafton, VT 05146

$49,900

Land0.50 acre (lot)

000 Hinkley Brook Rd, Grafton, VT 05146

Property at 0 Townshend Dam Rd, Wardsboro, VT 05355

$225,000

Land54.80 acres (lot)

0 Townshend Dam Rd, Wardsboro, VT 05355

Property at 251 Phillips Hill Rd, Halifax, VT 05358

$137,000

Land20.10 acres (lot)

251 Phillips Hill Rd, Halifax, VT 05358

Property at 00 Howe Farm Rd, Jamaica, VT 05343

$219,000

Land16.90 acres (lot)

00 Howe Farm Rd, Jamaica, VT 05343

Property at 28 Upper Howes Way Unit 00CHA028.000, Wilmington, VT 05363

$25,000

Land0.60 acre (lot)

28 Upper Howes Way Unit 00CHA028.000, Wilmington, VT 05363

Property at 00 W Hill Rd S, Jamaica, VT 05343

$450,000

Land30.00 acres (lot)

00 W Hill Rd S, Jamaica, VT 05343

Property at 45 Mowing Way, Wilmington, VT 05363

$45,000

Land0.25 acre (lot)

45 Mowing Way, Wilmington, VT 05363

Property at 00 E Putney Brook Rd #2, Putney, VT 05346

$160,000

Land9.30 acres (lot)

00 E Putney Brook Rd #2, Putney, VT 05346

Property at 191 Pingree Park Ln, Londonderry, VT 05148

$122,000

Land2.07 acres (lot)

191 Pingree Park Ln, Londonderry, VT 05148

Property at 16 Overlook Dr, West Dover, VT 05356

$250,000

Land7.80 acres (lot)

16 Overlook Dr, West Dover, VT 05356

Property at 000 Green Mountain Tpke, Chester, VT 05143

$249,000

Land84.00 acres (lot)

000 Green Mountain Tpke, Chester, VT 05143

Property at 402 Fox Mt. Rd Unit 00CHM402.000, CHM403.000, Wilmington, VT 05363

$85,000

Land1.02 acres (lot)

402 Fox Mt. Rd Unit 00CHM402.000, CHM403.000, Wilmington, VT 05363

Property at 00 E Hill Rd, Wardsboro, VT 05355

$135,000

Land16.05 acres (lot)

00 E Hill Rd, Wardsboro, VT 05355

Property at 1270 Melendy Hill Rd, Guilford, VT 05301

$259,900

Land29.20 acres (lot)

1270 Melendy Hill Rd, Guilford, VT 05301

Property at 19 Stone Ridge Loop #12, West Dover, VT 05356

$199,595

Land4.20 acres (lot)

19 Stone Ridge Loop #12, West Dover, VT 05356

Property at 8559 VT Route 30 Lot 2 & 3, Jamaica, VT 05343

$120,000

Land4.68 acres (lot)

8559 VT Route 30 Lot 2 & 3, Jamaica, VT 05343

Property at 000F-320 Bourbon Run, Jamaica, VT 05343

$65,000

Land1.00 acre (lot)

000F-320 Bourbon Run, Jamaica, VT 05343

Property at 00 Creamery Rd, Guilford, VT 05301

$105,000

Land1.30 acres (lot)

00 Creamery Rd, Guilford, VT 05301

Property at #4 Margeaux Ln Lot 4, Stratton Mountain, VT 05155

$375,000

Land5.54 acres (lot)

#4 Margeaux Ln Lot 4, Stratton Mountain, VT 05155

Property at 31 Woodsman Rd, West Dover, VT 05356

$55,000

Land1.05 acres (lot)

31 Woodsman Rd, West Dover, VT 05356

Property at Pond Rd #1, East Dummerston, VT 05346

$350,000

Land5.28 acres (lot)

Pond Rd #1, East Dummerston, VT 05346

Property at 170 Maple Dr, Wardsboro, VT 05355

$68,500

Land1.00 acre (lot)

170 Maple Dr, Wardsboro, VT 05355

Property at 24 Summit Cir, Brattleboro, VT 05301

$80,000

Land1.97 acres (lot)

24 Summit Cir, Brattleboro, VT 05301

Property at 4125 Chester Rd, Grafton, VT 05146

$150,000

Land23.40 acres (lot)

4125 Chester Rd, Grafton, VT 05146

Property at 00 Route 100, Jamaica, VT 05343

$210,000

Land35.00 acres (lot)

00 Route 100, Jamaica, VT 05343

Property at 4769 Pikes Falls Rd, Jamaica, VT 05143

$195,000

Land1.20 acres (lot)

4769 Pikes Falls Rd, Jamaica, VT 05143

Property at Scattered Timber Rd, Wilmington, VT 05363

$140,000

Land1.40 acres (lot)

Scattered Timber Rd, Wilmington, VT 05363

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Cheap Homes for Sale in Windham County

There are currently 270 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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