Homes with Basements for Sale in Windsor County, VT

319 homes

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ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
HAVING A HARD TIME FINDING AN AFFORDABLE LIVING SITUATION? With multiple income streams already established, this property offers a rare opportunity to choose your living preference (2 Bdrms, 1 Bdrm, or Efficiency) and offset almost ALL of your living expenses while owning a historic small town landmark. Originally established as the North Pomfret Store & Post Office c. 1830, this classic 3-story New Englander blends historic charm, flexible living space, and established rental income. There are multiple owner-occupied living opportunities in the larger two bedroom unit, or one of the two additional residential apartment units: Consisting of one 1-bedroom apartment, and one efficienc

$475,000

5 beds4 baths3,036 sq ft

7868 Pomfret Rd, North Pomfret, VT 05053

1.84 acre lot • Built 1830 • Listed 130 days

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
MOTIVATED SELLER - PRICE REDUCTION - GREAT LOCATION - Check out this Circa 1840's Farmhouse with attached Garage and Shed on 1.98 acres with open meadows and woods. First floor features an Eat-In Kitchen, Full Bathroom, Laundry Room, Living Room, Bedroom and Den/Dining Room with Pellet Stove. Upstairs you'll find 4 Bedrooms that need some cosmetic work. Just 3/4 mile from Exit 8 for easy commute to Upper Valley and Short drive to Okemo Ski Resort. Make your appointment today!!

$229,000

4 beds1 bath1,738 sq ft

1009 Route 131, Springfield, VT 05030

Attached garage • Full bathroom • Open meadows

3D WALKTHROUGH

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
Welcome to Okemo Pines! Tucked away just moments from the slopes, 42 Cedar Drive stands as a premier example of elegant timber frame architecture. This luxurious 4-bedroom, 3.5-bath residence combines rustic Vermont character with modern, high-end finishes. Step inside to an open-concept main level adorned with premium white oak floors. The breathtaking great room serves as the heart of the home, where a towering cathedral ceiling and a dramatic fieldstone fireplace create a warm, inviting ambiance beneath walls of glass that frame the surrounding scenery. The epicurean kitchen is a chef’s dream, outfitted with custom cherry cabinetry, a farmhouse sink, and a walk-in pantry. For ultim

$1,350,000

4 beds3.5 baths5,960 sq ft

42 Cedar Dr, Ludlow, VT 05149

Fieldstone fireplace • Cathedral ceiling • Walls of glass

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
The ideal property for a SKI CLUB! 7 bedrooms! 6 bathrooms! An immaculate, professionally appointed commercial kitchen! Spacious common rooms and dining areas! A classic and inviting bar/lounge area! An interior with the true Vermont style appeal of exposed beams, wood floors and a stone faced fireplace! This inviting New England style building is perfectly situated midway between world class skiing at Killington and the numerous year round amenities of shopping, dining and cultural events of historic Woodstock Village! The highly visible and well known property is easily accessed year round off a well maintained paved road. Conveniently separated within this highly versatile complex is a c

$749,000

7 beds8 baths7,428 sq ft

52 Upper Rd, Bridgewater, VT 05035

Commercial kitchen • Year round amenities • Bar lounge area

VIDEO TOUR

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
Trailside Village on Okemo, Unit 9C, is a meticulously maintained three-bedroom plus loft, two-bath condominium with direct ski access to the Sachem Trail. Beautifully updated throughout, the home features a renovated kitchen and bathrooms, custom wood trim, solid wood interior doors, and a warm blend of hickory hardwood flooring, tile, and plush carpeting. Thoughtful upgrades include enhanced lighting, newer appliances, and a recently installed washer and dryer. The spacious lower-level family room provides the perfect gathering space after a day on the slopes. Step outside through the sliding doors to a future outdoor retreat, where association-approved plans for a 9' x 9' deck or patio a

$579,000

3 beds2 baths1,470 sq ft

62 Okemo Trailside Ext Unit 9C, Ludlow, VT 05149

Direct ski access • Renovated kitchen • Custom wood trim

Property at 366 Knapp Pond Rd, Cavendish, VT 05142, 4 beds, 2 baths

$1,200,000

4 beds2 baths1,908 sq ft

366 Knapp Pond Rd, Cavendish, VT 05142

Property at 117 Horseshoe Dr, West Windsor, VT 05089, 3 beds, 3 baths

$779,000

3 beds3 baths3,392 sq ft

117 Horseshoe Dr, West Windsor, VT 05089

Property at 441 Rhoades Hill Rd, Barnard, VT 05031, 3 beds, 3 baths

$689,000

3 beds3 baths2,423 sq ft

441 Rhoades Hill Rd, Barnard, VT 05031

Property at 1036 N Main St, Bethel, VT 05031, 5 beds, 4.5 baths

$1,150,000

5 beds4.5 baths3,370 sq ft

1036 N Main St, Bethel, VT 05031

Property at 399 Bentley Rd, Hartford, VT 05059, 5 beds, 3.5 baths

$1,490,950

5 beds3.5 baths3,358 sq ft

399 Bentley Rd, Hartford, VT 05059

Property at 97 Okemo Trailside Ext Unit 15C, Ludlow, VT 05149, 3 beds, 3 baths

$625,000

3 beds3 baths1,376 sq ft

97 Okemo Trailside Ext Unit 15C, Ludlow, VT 05149

Property at 4205 Route 131, Perkinsville, VT 05151, 3 beds, 1.5 baths

$619,900

3 beds1.5 baths1,938 sq ft

4205 Route 131, Perkinsville, VT 05151

Property at 41 Pleasant St, Woodstock, VT 05091, 9 beds, 11 baths

$2,599,000

9 beds11 baths5,993 sq ft

41 Pleasant St, Woodstock, VT 05091

Property at 1057 Brockway Mills Rd, Springfield, VT 05156, 3 beds, 1 bath

$350,000

3 beds1 bath2,128 sq ft

1057 Brockway Mills Rd, Springfield, VT 05156

Property at 240 Ghia Farm Rd, Ludlow, VT 05149, 5 beds, 3 baths

$1,150,000

5 beds3 baths3,065 sq ft

240 Ghia Farm Rd, Ludlow, VT 05149

Property at 133 Stagecoach Rd, Norwich, VT 05055, 2 beds, 1 bath

$470,000

2 beds1 bath1,144 sq ft

133 Stagecoach Rd, Norwich, VT 05055

Property at 1787 Route 100 N, Ludlow, VT 05149, 3 beds, 4 baths

$535,000

3 beds4 baths2,727 sq ft

1787 Route 100 N, Ludlow, VT 05149

Property at 3578 Royalton Turnpike Rd, Barnard, VT 05031, 2 beds, 1 bath

$369,000

2 beds1 bath1,140 sq ft

3578 Royalton Turnpike Rd, Barnard, VT 05031

Property at 72 Wood Rd, Hartford, VT 05001, 3 beds, 2 baths

$1,300,000

3 beds2 baths2,334 sq ft

72 Wood Rd, Hartford, VT 05001

Property at 85 Townhouse Way #14, Woodstock, VT 05091, 2 beds, 3 baths

$450,000

2 beds3 baths2,091 sq ft

85 Townhouse Way #14, Woodstock, VT 05091

Property at 36 Lower IV A Unit 48B, Ludlow, VT 05149, 4 beds, 2.5 baths

$739,000

4 beds2.5 baths1,844 sq ft

36 Lower IV A Unit 48B, Ludlow, VT 05149

Property at 919 VT Route 100 S, Rochester, VT 05767, 3 beds, 1 bath

$339,000

3 beds1 bath1,144 sq ft

919 VT Route 100 S, Rochester, VT 05767

Property at 66 Duttonsville School Dr, Cavendish, VT 05142, 2.5 baths

$499,000

Studio2.5 baths7,445 sq ft

66 Duttonsville School Dr, Cavendish, VT 05142

Property at 178 Church St, Bethel, VT 05032, 1 bath

$50,000

Studio1 bath— sq ft

178 Church St, Bethel, VT 05032

Property at 6852 US Route 4, Bridgewater, VT 05034, 3 beds, 2 baths

$449,000

3 beds2 baths1,489 sq ft

6852 US Route 4, Bridgewater, VT 05034

Property at 54 Commonwealth Ave, Springfield, VT 05156, 3 beds, 2 baths

$390,000

3 beds2 baths1,214 sq ft

54 Commonwealth Ave, Springfield, VT 05156

Property at 726 E Ash Rd, Plymouth, VT 05056, 6 beds, 7.5 baths

$850,000

6 beds7.5 baths5,588 sq ft

726 E Ash Rd, Plymouth, VT 05056

Property at 505 Deweys Mills Rd, Hartford, VT 05047, 6 beds, 5 baths

$1,275,000

6 beds5 baths4,571 sq ft

505 Deweys Mills Rd, Hartford, VT 05047

Property at 325 Cemetery Rd, West Windsor, VT 05089, 4 beds, 2 baths

$1,325,000

4 beds2 baths2,554 sq ft

325 Cemetery Rd, West Windsor, VT 05089

Property at 109 Park Row, Rochester, VT 05767, 5 beds, 3.5 baths

$319,000

5 beds3.5 baths2,200 sq ft

109 Park Row, Rochester, VT 05767

Property at 924 Okemo Ridge Rd Unit S 11, Ludlow, VT 05149, 7 beds, 6.5 baths

$4,775,000

7 beds6.5 baths6,624 sq ft

924 Okemo Ridge Rd Unit S 11, Ludlow, VT 05149

Property at 196 Cowdrey Outlook, Bethel, VT 05032, 3 beds, 1 bath

$1,595,000

3 beds1 bath1,708 sq ft

196 Cowdrey Outlook, Bethel, VT 05032

Property at 879 E Ash Rd #5, Plymouth, VT 05056, 4 beds, 3.5 baths

$499,000

4 beds3.5 baths2,436 sq ft

879 E Ash Rd #5, Plymouth, VT 05056

Property at 310 Pierce Hill Rd, Brownsville, VT 05037, 7 beds, 5 baths

$1,295,000

7 beds5 baths5,774 sq ft

310 Pierce Hill Rd, Brownsville, VT 05037

Property at 1877 Willard Rd, Hartford, VT 05059, 4 beds, 3.5 baths

$730,000

4 beds3.5 baths2,970 sq ft

1877 Willard Rd, Hartford, VT 05059

Property at 879 E Ash Rd Unit L-8, Plymouth, VT 05056, 4 beds, 3 baths

$360,000

4 beds3 baths2,180 sq ft

879 E Ash Rd Unit L-8, Plymouth, VT 05056

Property at 3341 Trebo Rd, Chester, VT 05143, 4 beds, 2.5 baths

$535,000

4 beds2.5 baths2,464 sq ft

3341 Trebo Rd, Chester, VT 05143

Property at 51 High St, Ludlow, VT 05149, 5 beds, 2.5 baths

$729,000

5 beds2.5 baths2,018 sq ft

51 High St, Ludlow, VT 05149

Property at 51 E Ash Rd, Plymouth, VT 05056, 7 beds, 8.5 baths

$2,650,000

7 beds8.5 baths13,410 sq ft

51 E Ash Rd, Plymouth, VT 05056

Property at 299 Latham Works Ln, White River Junction, VT 05001, 3 beds, 1 bath

$369,440

3 beds1 bath1,569 sq ft

299 Latham Works Ln, White River Junction, VT 05001

Property at 26 Mt Peg Rd Unit B, Woodstock, VT 05091, 3 beds, 3.5 baths

$875,000

3 beds3.5 baths2,584 sq ft

26 Mt Peg Rd Unit B, Woodstock, VT 05091

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Homes with Basements for Sale in Windsor County

There are currently 319 homes with basements for sale in Windsor County at a median listing price of $575K. 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 85 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 68 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 105 condos, 0 townhouses, and 17 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 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 Sat Oct 10 2026 on the search page

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