Homes with Basements for Sale in Windsor County, VT

292 homes

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ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's most desirable locations: a place where life slows and the beauty of the Vermont countryside takes center stage. At the end of a quiet road, the property combines sweeping mountain views, and exceptional privacy with a thoughtfully designed hand-crafted, timber frame home. Outside, perennial gardens give way to open pasture suitable for a few horses or sheep, woodland trails for riding, hiking, cross-country skiing, and snowshoeing and direct access to the GMHA trail system. Built in 2015, the three-bedroom residence is defined by soaring spaces, exposed fir beams,

$5,875,000

3 beds3.5 baths5,384 sq ft

115 Eastman Rd, South Woodstock, VT 05071

Soaring spaces • Gourmet kitchen • Exposed fir beams

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
This is one of those homes you simply have to experience in person. The views alone are worth the visit. Perched above the valley with commanding, panoramic views of Mount Ascutney, this exceptional custom-built home offers a front-row seat to some of Vermont's most breathtaking scenery. From sunrise over the mountains to spectacular evening sunsets, every window showcases a landscape that changes beautifully with the seasons. Designed for comfortable everyday living and effortless entertaining, this thoughtfully crafted four-bedroom, three-bath home features the convenience of a first-floor primary suite, while three spacious upstairs bedrooms provide room for family, guests, or dedicated

$574,900

4 beds3 baths3,200 sq ft

84 Old Barn Ln, Brownsville, VT 05037

Large open yard • 3.2 acre lot • 2 garage spots

$390,000

3 beds2 baths1,214 sq ft

54 Commonwealth Ave, Springfield, VT 05156

0.38 acre lot • Garage • Built 1952

3D WALKTHROUGH

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to detail create a residence as enduring as it is beautiful. A flexible floor plan offers five bedrooms and three baths, including an elegant first-floor primary suite with ensuite bath, complemented by additional main-level bedroom options ideal for guests, multi-generational living, or a dedica

$789,000

5 beds3 baths4,388 sq ft

223 Coach Rd, Chester, VT 05143

Handsome library • Mature gardens • Landscaped acres

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ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
If you are a skier, this is your hop-on-the shuttle to Okemo location. If you want to park your car and walk to restaurants and shops, this is a great home base to scoot out from. If you want to generate rental income, this is a property that can allow you to have your cake and eat it too. An easy keeper, without a lot of landscape to take care of, this large residence has hardwood floors and handsome antique details. The main and second floor each offer three bedrooms, two baths, kitchen, and, if needed, separate entrances. Recent improvements include a large enclosed hot tub room and a new heating system. The third floor features a play room, another bath and tons of bonus space. Lots of

$599,999

6 beds5 baths4,184 sq ft

49 Pleasant St, Ludlow, VT 05149

Walk to restaurants • Play room • Shuttle to okemo

Property at 100 Riverside Ln, South Royalton, VT 05068, 3 beds, 2 baths

$425,000

3 beds2 baths1,344 sq ft

100 Riverside Ln, South Royalton, VT 05068

Property at 168 Chandler Rd, Chester, VT 05143, 3 beds, 2 baths

$649,000

3 beds2 baths2,204 sq ft

168 Chandler Rd, Chester, VT 05143

Property at 90 Limey Ln, North Pomfret, VT 05053, 3 beds, 1 bath

$499,500

3 beds1 bath1,024 sq ft

90 Limey Ln, North Pomfret, VT 05053

Property at 1522 Barnard Rd, Woodstock, VT 05091, 5 beds, 3.5 baths

$1,395,000

5 beds3.5 baths3,648 sq ft

1522 Barnard Rd, Woodstock, VT 05091

Property at 55 County Rd, Windsor, VT 05089, 3 beds, 3 baths

$1,625,000

3 beds3 baths4,922 sq ft

55 County Rd, Windsor, VT 05089

Property at 188 Wall St, Springfield, VT 05156, 3 beds, 2 baths

$359,000

3 beds2 baths2,100 sq ft

188 Wall St, Springfield, VT 05156

Property at 473 Kendall Rd, South Woodstock, VT 05071, 4 beds, 3 baths

$2,225,000

4 beds3 baths3,867 sq ft

473 Kendall Rd, South Woodstock, VT 05071

Property at 826 Hard Rd Unit B4, Quechee, VT 05059, 2 beds, 2.5 baths

$339,000

2 beds2.5 baths1,648 sq ft

826 Hard Rd Unit B4, Quechee, VT 05059

Property at 1821 Chateauguay Rd, Barnard, VT 05031, 3 beds, 2 baths

$379,000

3 beds2 baths1,635 sq ft

1821 Chateauguay Rd, Barnard, VT 05031

Property at 41 Lawrence Hill Rd, Weston, VT 05161, 7 beds, 5.5 baths

$699,000

7 beds5.5 baths4,642 sq ft

41 Lawrence Hill Rd, Weston, VT 05161

Property at 62 Okemo Trailside Ext Unit 9C, Ludlow, VT 05149, 3 beds, 2 baths

$579,000

3 beds2 baths1,470 sq ft

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

Property at 2706 E Woodstock Rd, Woodstock, VT 05091, 4 beds, 3.5 baths

$1,695,000

4 beds3.5 baths4,800 sq ft

2706 E Woodstock Rd, Woodstock, VT 05091

Property at 58 Lakeshore Dr, Ludlow, VT 05149, 4 beds, 3 baths

$3,500,000

4 beds3 baths2,571 sq ft

58 Lakeshore Dr, Ludlow, VT 05149

Property at 30 Densmore Dr, Bethel, VT 05032, 5 beds, 3 baths

$350,000

5 beds3 baths2,476 sq ft

30 Densmore Dr, Bethel, VT 05032

Property at 47 Pleasant St, Woodstock, VT 05091, 3 beds, 1.5 baths

$695,000

3 beds1.5 baths2,285 sq ft

47 Pleasant St, Woodstock, VT 05091

Property at 63 Royall Tyler Rd, Hartford, VT 05059, 4 beds, 2.5 baths

$949,000

4 beds2.5 baths3,183 sq ft

63 Royall Tyler Rd, Hartford, VT 05059

Property at 328 Gravelin Rd, Perkinsville, VT 05151, 4 beds, 4.5 baths

$1,600,000

4 beds4.5 baths4,636 sq ft

328 Gravelin Rd, Perkinsville, VT 05151

Property at 2404 Tarbell Hill Rd, Cavendish, VT 05142, 4 beds, 1.5 baths

$176,000

4 beds1.5 baths2,214 sq ft

2404 Tarbell Hill Rd, Cavendish, VT 05142

Property at 88 Summer St, Springfield, VT 05156, 5 beds, 2.5 baths

$649,000

5 beds2.5 baths4,306 sq ft

88 Summer St, Springfield, VT 05156

Property at 300 Great Hawk Rd, Rochester, VT 05767, 4 beds, 3 baths

$829,000

4 beds3 baths2,158 sq ft

300 Great Hawk Rd, Rochester, VT 05767

Property at 719 Walker Hill Rd, Barnard, VT 05031, 3 beds, 4 baths

$2,195,000

3 beds4 baths4,329 sq ft

719 Walker Hill Rd, Barnard, VT 05031

Property at 62 Moon Shadow Dr, Ludlow, VT 05149, 5 beds, 4.5 baths

$4,999,000

5 beds4.5 baths9,170 sq ft

62 Moon Shadow Dr, Ludlow, VT 05149

Property at 5893 Stage Rd, Barnard, VT 05031, 7 beds, 8 baths

$3,750,000

7 beds8 baths9,615 sq ft

5893 Stage Rd, Barnard, VT 05031

Property at 156 Main St, Ludlow, VT 05149, 10 beds, 7 baths

$1,550,000

10 beds7 baths7,566 sq ft

156 Main St, Ludlow, VT 05149

Property at 192 Birch Hill Rd, Bethel, VT 05032, 5 beds, 3 baths

$625,000

5 beds3 baths2,830 sq ft

192 Birch Hill Rd, Bethel, VT 05032

Property at 10 W Hill St, Ludlow, VT 05149, 3 beds, 1 bath

$405,000

3 beds1 bath1,239 sq ft

10 W Hill St, Ludlow, VT 05149

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 530 West Rd, Barnard, VT 05031, 3 beds, 2 baths

$569,000

3 beds2 baths1,924 sq ft

530 West Rd, Barnard, VT 05031

Property at 574 Willard Rd Unit 3F, Hartford, VT 05059, 2 beds, 1 bath

$239,000

2 beds1 bath880 sq ft

574 Willard Rd Unit 3F, Hartford, VT 05059

Property at 1641 W Hill Rd, Rochester, VT 05767, 3 beds, 3 baths

$640,000

3 beds3 baths2,697 sq ft

1641 W Hill Rd, Rochester, VT 05767

Property at 366 Crimson Hawk Rd Unit S1-24, Plymouth, VT 05056, 3 beds, 2 baths

$475,000

3 beds2 baths1,308 sq ft

366 Crimson Hawk Rd Unit S1-24, Plymouth, VT 05056

Property at 1319 Brandon Mountain Rd, Rochester, VT 05767, 3 beds, 3 baths

$399,000

3 beds3 baths2,184 sq ft

1319 Brandon Mountain Rd, Rochester, VT 05767

Property at 683 Reservoir Rd, White River Junction, VT 05001, 3 beds, 2.5 baths

$1,395,000

3 beds2.5 baths2,112 sq ft

683 Reservoir Rd, White River Junction, VT 05001

Property at 764 Upper Sparrow Hawk Rd, Rochester, VT 05767, 3 beds, 2.5 baths

$1,125,000

3 beds2.5 baths2,520 sq ft

764 Upper Sparrow Hawk Rd, Rochester, VT 05767

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

$25,000,000

2 beds5.5 baths9,950 sq ft

650 Francis Rd, Barnard, VT 05031

Property at 177 Old Tavern Rd, Weston, VT 05161, 3 beds, 3.5 baths

$850,000

3 beds3.5 baths2,913 sq ft

177 Old Tavern Rd, Weston, VT 05161

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Homes with Basements for Sale in Windsor County

There are currently 292 homes with basements for sale in Windsor County at a median listing price of $569K. 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 70 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 63 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 99 condos, 0 townhouses, and 21 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 Tue Aug 25 2026 on the search page

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