Homes with Basements for Sale in Windham County, VT

244 homes

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ABOUT THIS HOME
Home with Basement for sale in Windham County, VT:
Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts. The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a seamless connection with the outdoors. A Pellet stove with the fieldstone fireplace adds warmth and character to the main living space. Just off the living area, a second living room with a sleeping area offers a perfect spot for a home office or guest wing while enjoying lake views. Upstairs, you'll find two

$1,040,000

5 beds4.5 baths3,363 sq ft

1189 Cole Pond Rd, Jamaica, VT 05343

Fieldstone chimney • Waterfront home • Lake views

ABOUT THIS HOME
Home with Basement for sale in Windham County, VT:
Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no matter the weather. Or you can relax in the hot tub after a long day and even enjoy the sounds of a local waterfall located just a short walk from the doorstep. A 1-bedroom apartment with a separate entrance gives this home more flexibility for family and friends to stay for extended visits. The two-c

$850,000

5 beds4 baths3,218 sq ft

4880 Pikes Falls Rd, Jamaica, VT 05343

Separate entrance • Open dining area • Hot tub

ABOUT THIS HOME
Home with Basement for sale in Windham County, VT:
Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers an excellent opportunity for investors. Two of the three units have been recently and extensively renovated, featuring brand-new flooring, fresh paint, modern baseboards, and updated plumbing and light fixtures. All three units are currently occupied, providing immediate cash flow. Unit 2 also benefits from a recently installed water heater. Enjoy peace of mind with separate utilities, state lead compliance, vinyl siding, and several replacement windows. Located in a highly walkable area—just steps from downtown, grocery stores, the hospital, and public transit—this property co

$284,000

5 beds3 baths2,360 sq ft

5 Reynolds Dr, Brattleboro, VT 05301

Modern baseboards • Fresh paint • New flooring

FLOOR PLAN

ABOUT THIS HOME
Home with Basement for sale in Windham County, VT:
STRONG RENTAL HISTORY & INVESTMENT OPPORTUNITY IN A TURN-KEY PROPERTY. Located in the heart of Grafton, Vermont, on a spacious one-acre, flat lot a quick stroll from town, this extensively renovated property offers exceptional flexibility and scale. The single family or multi-family property is configured to allow division into two condominium-style living spaces plus a separate artist loft or accessory dwelling, each with its own entrance, creating versatile possibilities for expansive residential living, multi-generational housing, a vacation retreat or investment opportunity with three rentable units. The home features six bedrooms, plus a loft, and has been thoughtfully updated wi

$999,000

6 beds4.5 baths5,828 sq ft

151 Townshend Rd, Grafton, VT 05146

Separate artist loft • New kitchens • Renovated bathrooms

ABOUT THIS HOME
Home with Basement for sale in Windham County, VT:
Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private lot in the Chimney Hill community on a quiet side road with easterly mountain views. Inside you will find a lovely open concept living space with vaulted ceilings and exposed woodwork, great natural light thanks to large windows, a spacious great room with wood burning fireplace, brick hearth, and

$489,000

3 beds2 baths2,003 sq ft

12 Lilla Ln, Wilmington, VT 05363

Private lot • Nearby hiking areas • Vaulted ceilings

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

$690,000

5 beds3 baths2,635 sq ft

341 Under The Mountain Rd, South Londonderry, VT 05155

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

$428,000

4 beds3.5 baths2,015 sq ft

29 First Ln #17, Wilmington, VT 05363

Property at 794 White Rd, Chester, VT 05359, 2 beds, 2 baths

$549,000

2 beds2 baths850 sq ft

794 White Rd, Chester, VT 05359

Property at 135 Overlook Dr, Londonderry, VT 05148, 5 beds, 3 baths

$425,000

5 beds3 baths1,440 sq ft

135 Overlook Dr, Londonderry, VT 05148

Property at 2170 N Main St, Londonderry, VT 05148

$675,000

— beds— baths6,144 sq ft

2170 N Main St, Londonderry, VT 05148

Property at 628 Townshend Rd, Grafton, VT 05146, 3 beds, 2.5 baths

$549,000

3 beds2.5 baths2,782 sq ft

628 Townshend Rd, Grafton, VT 05146

Property at 195 Mann Rd #12, Wilmington, VT 05356, 3 beds, 3.5 baths

$425,000

3 beds3.5 baths2,814 sq ft

195 Mann Rd #12, Wilmington, VT 05356

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

$2,495,000

6 beds6 baths6,400 sq ft

56 Handle Rd, West Dover, VT 05356

Property at 925 Hinesburg Rd, Brattleboro, VT 05301, 5 beds, 6.5 baths

$899,800

5 beds6.5 baths7,430 sq ft

925 Hinesburg Rd, Brattleboro, VT 05301

Property at 14A Grouse Ln Unit 14A, Dover, VT 05356, 4 beds, 3 baths

$679,000

4 beds3 baths2,600 sq ft

14A Grouse Ln Unit 14A, Dover, VT 05356

Property at 39D Dover Springs Ln, Dover, VT 04356, 4 beds, 4 baths

$799,000

4 beds4 baths3,200 sq ft

39D Dover Springs Ln, Dover, VT 04356

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

$389,900

2 beds2 baths1,250 sq ft

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

Property at 14 High Top Rd Unit B124, Wilmington, VT 05363, 3 beds, 3 baths

$535,000

3 beds3 baths2,397 sq ft

14 High Top Rd Unit B124, Wilmington, VT 05363

Property at 10B Grouse Ln, West Dover, VT 05356, 4 beds, 3 baths

$649,000

4 beds3 baths2,600 sq ft

10B Grouse Ln, West Dover, VT 05356

Property at 33D White Oaks Loop #38, West Dover, VT 05356, 3 beds, 3 baths

$469,000

3 beds3 baths2,016 sq ft

33D White Oaks Loop #38, West Dover, VT 05356

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 25 Upper Handle Rd Unit A, West Dover, VT 05356, 3 beds, 2 baths

$350,000

3 beds2 baths1,400 sq ft

25 Upper Handle Rd Unit A, West Dover, VT 05356

Property at 32 Old Town Rd, West Dover, VT 05356, 5 beds, 3 baths

$799,000

5 beds3 baths3,306 sq ft

32 Old Town Rd, West Dover, 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

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

$435,000

4 beds2 baths1,344 sq ft

27 Country Ct, Wilmington, VT 05363

Property at 36 Woffenden Rd, Wilmington, VT 05363, 6 beds, 2 baths

$2,699,000

6 beds2 baths3,309 sq ft

36 Woffenden Rd, Wilmington, VT 05363

Property at 109 Central St, Brattleboro, VT 05301, 4 beds, 2 baths

$350,000

4 beds2 baths1,808 sq ft

109 Central St, Brattleboro, VT 05301

Property at 15B Boulder Ridge Dr, West Dover, VT 05356, 4 beds, 4 baths

$949,000

4 beds4 baths3,100 sq ft

15B Boulder Ridge Dr, West Dover, VT 05356

Property at 233 Poverty Row, Whitingham, VT 05361, 3 beds, 4 baths

$699,000

3 beds4 baths3,796 sq ft

233 Poverty Row, Whitingham, VT 05361

Property at 25 Cottage St, Brattleboro, VT 05301, 6 beds, 4 baths

$380,000

6 beds4 baths3,264 sq ft

25 Cottage St, Brattleboro, VT 05301

Property at 556 S Main St, Brattleboro, VT 05301, 6 beds, 2 baths

$250,000

6 beds2 baths2,112 sq ft

556 S Main St, Brattleboro, VT 05301

Property at 662 Howe Farm Rd, Jamaica, VT 05343, 4 beds, 4.5 baths

$2,399,000

4 beds4.5 baths3,569 sq ft

662 Howe Farm Rd, Jamaica, VT 05343

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

$1,050,000

5 beds4.5 baths4,040 sq ft

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

Property at 16 Tenth Ln #40, Wilmington, VT 05363, 4 beds, 3.5 baths

$450,000

4 beds3.5 baths1,800 sq ft

16 Tenth Ln #40, Wilmington, VT 05363

Property at 136 Vermont Route 100, West Dover, VT 05356, 7 beds, 6.5 baths

$825,000

7 beds6.5 baths1,152 sq ft

136 Vermont Route 100, West Dover, VT 05356

Property at 41 Two Brook Dr, Wilmington, VT 05363, 4 beds, 3.5 baths

$798,000

4 beds3.5 baths3,420 sq ft

41 Two Brook Dr, Wilmington, VT 05363

Property at 36A Boulder Ridge Dr, Mt Snow, VT 05356, 5 beds, 4.5 baths

$1,560,000

5 beds4.5 baths4,100 sq ft

36A Boulder Ridge Dr, Mt Snow, VT 05356

Property at 10 Birge St, Brattleboro, VT 05301, 5 beds, 4 baths

$350,000

5 beds4 baths3,002 sq ft

10 Birge St, Brattleboro, VT 05301

Property at 573 S Main St, Brattleboro, VT 05301, 2 beds, 4 baths

$350,000

2 beds4 baths3,312 sq ft

573 S Main St, Brattleboro, VT 05301

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Homes with Basements for Sale in Windham County

There are currently 244 homes with basements for sale in Windham County at a median listing price of $479K. 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 66 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 85 condos, 0 townhouses, and 18 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 Tue Aug 25 2026 on the search page

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