Homes with Basements for Sale in Windsor County, VT

282 homes

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NEW 15 HRS AGOVIDEO TOUR

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
Step back in time with this charming brick Colonial home, built in 1830 and beautifully situated in the heart of Proctorsville Village. Rich in history and character, this residence offers the perfect blend of classic New England architecture and convenient village living—just steps from shops, schools, restaurants, and the village green that adds to its timeless charm. The main level welcomes you with a traditional layout featuring a spacious country kitchen, a formal dining room, and a large living room ideal for gatherings. A full bathroom on this level adds modern comfort and convenience. Upstairs, you’ll find four inviting bedrooms and a three-quarter bathroom, providing am

$249,000

4 beds2 baths2,016 sq ft

58 Depot St, Chester, VT 05153

Brick colonial home • Country kitchen • Attic space

NEW 17 HRS AGO

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
Almost there! This owner has taken this property to a new level. .. had the septic discovered and has a report, upgraded the electric entrance and added an EV station, laid flooring, opened up a wall for a much nicer open concept, cleaned and made into a little cottage for skiing, nature loving or just plain home. There are rain barrels for water, let nature fill them up or hire the local water company. Provision has been made for a spring in the back area. There is a seasonal stream bed next to the deck for a touch of nature. It is your turn, lift this affordable A frame to the next level. Seller has estimates for some of the upgrades. Or, use it as it is as a camp in Vermont.

$149,900

2 beds1 bath1,120 sq ft

4351 Vermont RT 11 W, Chester, VT 05143

Open concept • Ev station • Seasonal stream bed

NEW 17 HRS AGO

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
1806 Brick Cape in need of new owners prepared to build equity in this wonderful treasure with 18 acres on the edge of quaint E. Bethel Village. 'AS IS' CONDITION.

$225,000

3 beds1 bath1,591 sq ft

176 Store Hill Rd, Bethel, VT 05032

18 acre lot • Built 1806

NEW 18 HRS AGO

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
Bring your vision to this charming 3-bedroom, 1-bath farmhouse in the heart of Cavendish, a true opportunity for those looking to restore or reimagine a home with character. Set on a generous 1.6-acre lot, the property offers endless potential with plenty of space to expand, garden, or create your dream outdoor retreat. Inside, you’ll find original hardwood floors throughout and good bones that provide a solid foundation for updates and customization. The oversized detached garage is a major bonus, ideal for workshop space, storage, or hobby use. If you’re searching for a project with classic New England charm and room to grow, this is the one. Unlock the potential and make it y

$299,000

3 beds1 bath1,800 sq ft

50 Bates Rd, Cavendish, VT 05142

1.6-acre lot • 1.6 acre lot • 2 garage spots

NEW 22 HRS AGO

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
Situated in a serene country setting just moments from the conveniences of town, 215 Elm Hill Street offers the ideal combination of privacy, comfort, and understated elegance. This beautifully maintained home features over 2,200 square feet of bright and inviting living space, designed for both relaxation and effortless entertaining. The expansive 1.25 acre lot is level and open, creating a natural sense of space and tranquility. Spend your summer days by the sparkling in-ground pool or host gatherings on the lush lawn surrounded by mature trees and peaceful views. Inside, large sunlit rooms flow easily from one to the next, creating a warm and welcoming atmosphere throughout. A spacious b

$395,000

4 beds2.5 baths2,240 sq ft

215 Elm Hill St, Springfield, VT 05156

In-ground pool • 1.25 acre lot • Large sunlit rooms

Property at 27 Ash St, White River Junction, VT 05001, 4 beds, 3 baths

$499,000

4 beds3 baths2,400 sq ft

27 Ash St, White River Junction, VT 05001

Property at 1362 Barnard Rd, Woodstock, VT 05091, 4 beds, 2 baths

$2,600,000

4 beds2 baths3,000 sq ft

1362 Barnard Rd, Woodstock, VT 05091

Property at 51 Terrace St, Woodstock, VT 05091, 2 beds, 2 baths

$500,000

2 beds2 baths1,237 sq ft

51 Terrace St, Woodstock, VT 05091

Property at 1873 Old River Rd, White River Junction, VT 05001, 2 beds, 1 bath

$425,000

2 beds1 bath908 sq ft

1873 Old River Rd, White River Junction, VT 05001

Property at 650 Francis Rd, Barnard, VT 05031, 2 beds, 5.5 baths

$39,000,000

2 beds5.5 baths9,950 sq ft

650 Francis Rd, Barnard, VT 05031

Property at 1928 VT. Route 131, Springfield, VT 05156, 4 beds, 1.5 baths

$825,000

4 beds1.5 baths2,200 sq ft

1928 VT. Route 131, Springfield, VT 05156

Property at 61 Pleasant St, Ludlow, VT 05149, 8 beds, 6 baths

$499,000

8 beds6 baths3,683 sq ft

61 Pleasant St, Ludlow, VT 05149

Property at 483 South St, Springfield, VT 05156, 3 beds, 1 bath

$265,000

3 beds1 bath1,716 sq ft

483 South St, Springfield, VT 05156

Property at 76 Colonial Dr #13, White River Junction, VT 05001, 2 beds, 1.5 baths

$239,900

2 beds1.5 baths1,072 sq ft

76 Colonial Dr #13, White River Junction, VT 05001

Property at 198 Depot St, Proctorsville, VT 05153, 5 beds, 3 baths

$415,000

5 beds3 baths1,976 sq ft

198 Depot St, Proctorsville, VT 05153

Property at 355 Greene Rd, South Woodstock, VT 05071, 7 beds, 8.5 baths

$18,000,000

7 beds8.5 baths12,520 sq ft

355 Greene Rd, South Woodstock, VT 05071

Property at 51 Depot St #8, Cavendish, VT 05142, 2 beds, 1 bath

$115,000

2 beds1 bath560 sq ft

51 Depot St #8, Cavendish, VT 05142

Property at 125 Redfield Proctor Rd, Hartford, VT 05059, 4 beds, 2 baths

$825,000

4 beds2 baths2,516 sq ft

125 Redfield Proctor Rd, Hartford, VT 05059

Property at 17 Linden Hl, Woodstock, VT 05091, 4 beds, 3 baths

$1,200,000

4 beds3 baths2,736 sq ft

17 Linden Hl, Woodstock, VT 05091

Property at 68 Passumpsic Ave, Hartford, VT 05088, 5 beds, 3 baths

$599,000

5 beds3 baths2,600 sq ft

68 Passumpsic Ave, Hartford, VT 05088

Property at 48 School St, North Springfield, VT 05150, 2 beds, 1 bath

$215,000

2 beds1 bath676 sq ft

48 School St, North Springfield, VT 05150

Property at 89 route 12, Hartland, VT 05048, 3 beds, 1 bath

$179,000

3 beds1 bath1,554 sq ft

89 route 12, Hartland, VT 05048

Property at 1079 Fletcher Hill Rd, Woodstock, VT 05071, 2 beds, 2 baths

$425,000

2 beds2 baths1,440 sq ft

1079 Fletcher Hill Rd, Woodstock, VT 05071

Property at 184 Hazen St, White River Junction, VT 05001, 3 beds, 1.5 baths

$319,000

3 beds1.5 baths1,408 sq ft

184 Hazen St, White River Junction, VT 05001

Property at 223 Route 100 S, Ludlow, VT 05149, 5 beds, 3 baths

$295,000

5 beds3 baths3,474 sq ft

223 Route 100 S, Ludlow, VT 05149

Property at 513 Deer Brook Way Lot 16, Woodstock, VT 05091, 4 beds, 2.5 baths

$1,295,000

4 beds2.5 baths2,668 sq ft

513 Deer Brook Way Lot 16, Woodstock, VT 05091

Property at 493 Kestrell Dr, Plymouth, VT 05056, 4 beds, 3.5 baths

$657,500

4 beds3.5 baths2,126 sq ft

493 Kestrell Dr, Plymouth, VT 05056

Property at 75 Whitney Rd, Springfield, VT 05156, 3 beds, 1 bath

$239,000

3 beds1 bath1,152 sq ft

75 Whitney Rd, Springfield, VT 05156

Property at 211 Wood Rd, Hartford, VT 05059, 3 beds, 2 baths

$795,000

3 beds2 baths1,940 sq ft

211 Wood Rd, Hartford, VT 05059

Property at 77 Winding Rd, Brownsville, VT 05037, 4 beds, 2 baths

$520,000

4 beds2 baths2,380 sq ft

77 Winding Rd, Brownsville, VT 05037

Property at 9 Fairview St, Springfield, VT 05156, 4 beds, 1.5 baths

$200,000

4 beds1.5 baths1,482 sq ft

9 Fairview St, Springfield, VT 05156

Property at 240 Piper Hill Rd, Weston, VT 05161, 5 beds, 6.5 baths

$2,950,000

5 beds6.5 baths8,056 sq ft

240 Piper Hill Rd, Weston, VT 05161

Property at 475 Twenty Mile Stream Rd, South Reading, VT 05062, 3 beds, 3 baths

$895,000

3 beds3 baths3,920 sq ft

475 Twenty Mile Stream Rd, South Reading, VT 05062

Property at 60 Spencer Hollow Rd, Springfield, VT 05156, 2 beds, 3 baths

$899,000

2 beds3 baths2,250 sq ft

60 Spencer Hollow Rd, Springfield, VT 05156

Property at 1001 Woodstock Rd, White River Junction, VT 05001, 2 beds, 2 baths

$379,900

2 beds2 baths1,584 sq ft

1001 Woodstock Rd, White River Junction, VT 05001

Property at 31 Lakota Rd, Barnard, VT 05031, 3 beds, 2 baths

$459,900

3 beds2 baths1,288 sq ft

31 Lakota Rd, Barnard, VT 05031

Property at 93 Blake Hill Rd Unit B, Woodstock, VT 05091, 3 beds, 2.5 baths

$598,000

3 beds2.5 baths2,100 sq ft

93 Blake Hill Rd Unit B, Woodstock, VT 05091

Property at 1452 Tyson Rd, Reading, VT 05062, 2 beds, 1 bath

$475,000

2 beds1 bath1,020 sq ft

1452 Tyson Rd, Reading, VT 05062

Property at 5798 W Woodstock Rd, Woodstock, VT 05091, 4 beds, 2 baths

$439,000

4 beds2 baths1,617 sq ft

5798 W Woodstock Rd, Woodstock, VT 05091

Property at 1607 Massey Rd, Springfield, VT 05156, 4 beds, 2 baths

$995,000

4 beds2 baths4,144 sq ft

1607 Massey Rd, Springfield, VT 05156

Property at 870 Cummings Rd, Chester, VT 05143, 3 beds, 1.5 baths

$329,000

3 beds1.5 baths1,525 sq ft

870 Cummings Rd, Chester, VT 05143

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Homes with Basements for Sale in Windsor County

There are currently 282 homes with basements for sale in Windsor County at a median listing price of $549K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windsor County stay on the market for 80 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 94 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 101 condos, 4 townhouses, and 25 multi-family units for sale in Windsor County last month. Find your dream home in Windsor 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 Windsor County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windsor County. If you're looking to sell your home in the Windsor County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windsor 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 Fri Oct 24 2025 on the search page

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