Homes with Basements for Sale in Windham County, VT

203 homes

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ABOUT THIS HOME
Home with Basement for sale in Windham County, VT:
Welcome to the quaint Vermont village of Jamaica! Get ready to let your imagination take over. This historic property boasts two dwellings and a guest cottage. Looking for a family compound to get away from it all?This is your haven! Plenty of room to have friends and family come and stay! So many options. The Main House features 4 ensuite bedrooms! The living room is a late 1700"s delight, with an inviting fireplace to cozy around on cold winter nights. The formal dining room and library offer many options for you and your guests. The bonus room (formerly the Tavern) is perfect for entertaining young and old. The Depot Street house includes 4 bedrooms and 3 bathrooms on two floors. As

$975,000

9 beds8 baths5,480 sq ft

3732 Vt Route 30, Jamaica, VT 05343

Gazebo • Guest cottage • Updated kitchen

ABOUT THIS HOME
Home with Basement for sale in Windham County, VT:
Sage Hill offers the perfect blend of privacy and convenience, set along a scenic country road yet just minutes to groceries, gas, and skiing. This contemporary home is thoughtfully tucked back into the landscape, framed by classic stonewalls and majestic oak trees. Enter directly from the carport into a tiled mudroom with closet space, ideal for storing all your outdoor gear. The main living area features a soaring vaulted ceiling anchored by a striking fieldstone wood-burning fireplace, a cozy galley kitchen, and a spacious sunroom with its own woodstove to keep you warm on cool evenings. The home offers two en-suite bedrooms, each with a ¾ bath, plus an open loft overlooking the l

$479,000

2 beds2 baths2,016 sq ft

529 Finkel Rd, Wardsboro, VT 05355

Vaulted ceiling • Open loft • Tiled mudroom

ABOUT THIS HOME
Home with Basement for sale in Windham County, VT:
This recently renovated home is located on and with gorgeous views of the Connecticut River, frontage suitable for a wharf. Two bedrooms, two full baths and a beautifully crafted stone and brick fireplace. A large, private backyard, inviting family gatherings, just minutes to I91 and Okemo Mountain. Motivated Seller

$275,000

2 beds2 baths1,440 sq ft

10 Riverfront Dr, Bellows Falls, VT 05101

0.35 acre lot • Built 1950 • Listed 158 days

ABOUT THIS HOME
Home with Basement for sale in Windham County, VT:
This custom built 2018 log home, designed by RH Log Works and Hilderbrand Interiors, offers the ultimate in sophistication and luxury. Featured in Better Homes and Gardens, New England Home and Country Home magazines, this 5 bedroom, 4.5 bathroom sanctuary (plus extra bunk room) is nestled on 2.2 wooded acres with a river running alongside. Just 4 minutes from Hermitage Club and 10 minutes from Mt Snow. The 5,110 square feet of meticulously designed living space seamlessly blends modern elegance with timeless log cabin charm including a kitchen with Lacanche Citeaux range, tile backsplash, and custom steel-and-brass hood, great room with stunning stone fireplace, guest bath, primary suite w

$2,197,000

5 beds4.5 baths5,110 sq ft

14 Tarheel Trl, Wilmington, VT 05363

2.5 wooded acres • Tile backsplash • Custom built home

ABOUT THIS HOME
Home with Basement for sale in Windham County, VT:
3 Shannon Ridge Road, West Dover, VT Private Mountain Retreat Between Mount Snow and The Hermitage Club Experience the perfect fusion of luxury, privacy, and adventure in this beautifully renovated 4,950 sq ft home set on 1.62 acres of tranquil Vermont countryside. Ideally positioned between Mount Snow and the private Hermitage Club, this home offers a rare opportunity for refined mountain living with all-season access to premier skiing, hiking, and outdoor recreation. Over the course of a meticulous 20-month renovation, the property has been transformed into a modern mountain sanctuary designed for entertaining, relaxing, and enjoying the best of Vermont living.

$1,150,000

4 beds4.5 baths5,000 sq ft

3 Shannon Ridge Rd, West Dover, VT 05356

Premier skiing • All-season access • 1.62 acre lot

Property at 204 Meetinghouse Ln, Brattleboro, VT 05301, 4 beds, 2 baths

$579,000

4 beds2 baths2,656 sq ft

204 Meetinghouse Ln, Brattleboro, VT 05301

Property at 44 Tanglewood Ln Unit E, Dover, VT 05356, 3 beds, 2 baths

$475,000

3 beds2 baths2,016 sq ft

44 Tanglewood Ln Unit E, Dover, VT 05356

Property at 4448 Route 100, Wardsboro, VT 05355, 4 beds, 3 baths

$625,000

4 beds3 baths2,775 sq ft

4448 Route 100, Wardsboro, VT 05355

Property at 95 Melendy Hill Rd, South Londonderry, VT 05148, 6 beds, 3 baths

$639,000

6 beds3 baths2,825 sq ft

95 Melendy Hill Rd, South Londonderry, VT 05148

Property at 301 Maple St, Brattleboro, VT 05301, 4 beds, 2 baths

$515,000

4 beds2 baths3,090 sq ft

301 Maple St, Brattleboro, VT 05301

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 916 Wiswall Hill Rd, Townshend, VT 05353, 5 beds, 3.5 baths

$649,000

5 beds3.5 baths2,706 sq ft

916 Wiswall Hill Rd, Townshend, VT 05353

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 45 Dover Hill Rd, East Dover, VT 05341, 4 beds, 2 baths

$469,000

4 beds2 baths2,219 sq ft

45 Dover Hill Rd, East Dover, VT 05341

Property at 104 Karen Day Rd, Halifax, VT 05358, 4 beds, 1 bath

$579,000

4 beds1 bath1,560 sq ft

104 Karen Day Rd, Halifax, VT 05358

Property at 42 Airport Rd, Dover, VT 05356, 4 beds, 4 baths

$799,000

4 beds4 baths3,691 sq ft

42 Airport Rd, Dover, VT 05356

Property at 49 Joans Ridge Rd, West Dover, VT 05356, 3 beds, 4.5 baths

$949,000

3 beds4.5 baths2,800 sq ft

49 Joans Ridge Rd, West Dover, VT 05356

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 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 85 Browns Rd, Newfane, VT 05345, 2 beds, 2 baths

$795,000

2 beds2 baths2,190 sq ft

85 Browns Rd, Newfane, VT 05345

Property at 56 Handle Rd, West Dover, VT 05356, 6 beds, 6 baths

$2,889,000

6 beds6 baths6,400 sq ft

56 Handle Rd, West Dover, VT 05356

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 6036 Jacksonville Stage Rd, Halifax, VT 05358, 5 beds, 1 bath

$925,000

5 beds1 bath1,224 sq ft

6036 Jacksonville Stage Rd, Halifax, VT 05358

Property at 45 Blue Brook Rd, West Dover, VT 05356, 7 beds, 2 baths

$499,000

7 beds2 baths2,038 sq ft

45 Blue Brook Rd, West Dover, VT 05356

Property at 22 Lower Howes Rd Unit A89, Wilmington, VT 05363, 3 beds, 2 baths

$514,999

3 beds2 baths2,100 sq ft

22 Lower Howes Rd Unit A89, Wilmington, VT 05363

Property at 341 Under The Mountain Rd, South Londonderry, VT 05155, 5 beds, 3 baths

$730,000

5 beds3 baths2,635 sq ft

341 Under The Mountain Rd, South Londonderry, VT 05155

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 21 Main St, Saxtons River, VT 05154, 5 beds, 3 baths

$369,000

5 beds3 baths3,364 sq ft

21 Main St, Saxtons River, VT 05154

Property at 159 Westminster Rd, Putney, VT 05346, 4 beds, 3.5 baths

$699,000

4 beds3.5 baths4,540 sq ft

159 Westminster Rd, Putney, VT 05346

Property at 4B Hardwood Hl, Stratton, VT 05155, 3 beds, 3 baths

$1,150,000

3 beds3 baths2,121 sq ft

4B Hardwood Hl, Stratton, VT 05155

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 38B Greensprings Rd, Dover, VT 05356, 3 beds, 3.5 baths

$645,000

3 beds3.5 baths2,472 sq ft

38B Greensprings Rd, Dover, VT 05356

Property at 17A Boulder Ridge Dr Unit A, West Dover, VT 05356, 5 beds, 4.5 baths

$1,100,000

5 beds4.5 baths4,040 sq ft

17A Boulder Ridge Dr Unit A, West Dover, VT 05356

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 1189 Cole Pond Rd, Jamaica, VT 05343, 5 beds, 4.5 baths

$1,040,000

5 beds4.5 baths3,363 sq ft

1189 Cole Pond Rd, Jamaica, VT 05343

Property at 14 Johnson Hill Rd, West Dover, VT 05356, 3 beds, 3 baths

$649,000

3 beds3 baths2,170 sq ft

14 Johnson Hill Rd, West Dover, VT 05356

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

$310,000

4 beds2 baths2,408 sq ft

78-80 Central St, Brattleboro, VT 05301

Property at 3F Slalom Ln, West Dover, VT 05356, 4 beds, 4.5 baths

$1,249,000

4 beds4.5 baths3,500 sq ft

3F Slalom Ln, West Dover, VT 05356

Property at 5825 Route 30, Townshend, VT 05359, 6 beds, 4.5 baths

$929,000

6 beds4.5 baths3,500 sq ft

5825 Route 30, Townshend, VT 05359

Property at 18 New England Power Rd, Wilmington, VT 05363, 5 beds, 5 baths

$2,150,000

5 beds5 baths5,500 sq ft

18 New England Power Rd, Wilmington, VT 05363

Property at 28 Country Club Rd, West Dover, VT 05356, 4 beds, 3 baths

$497,500

4 beds3 baths1,776 sq ft

28 Country Club Rd, West Dover, VT 05356

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Homes with Basements for Sale in Windham County

There are currently 203 homes with basements for sale in Windham County at a median listing price of $498K. 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 85 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 100 condos, 6 townhouses, and 13 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 Mon Nov 24 2025 on the search page

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