Homes with Basements for Sale in Windsor County, VT

249 homes

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ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
Step into history with this beautifully maintained property in the heart of Proctorsville — formerly the Okemo Lantern Lodge and now a thriving short-term rental and family vacation retreat. Rich with character, this historic home showcases timeless woodwork, period details, and plenty of charm, while offering all the updates needed for today’s modern use. Located directly along the Okemo Shuttle Route and just across the street from the iconic Singleton’s General Store, this property puts you and your guests in the perfect spot to enjoy everything the area has to offer — from skiing and snowboarding at Okemo Mountain to exploring Vermont’s year-round recreatio

$799,000

11 beds10.5 baths5,102 sq ft

329 Main St, Proctorsville, VT 05153

Vermont history • Historic home • Detached garage

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
Bring your hammer and nails—this 4-bedroom, 2 bath Colonial is ready for its next chapter! Offering over 2,500 square feet of living space, this home combines classic character with plenty of potential. Tucked away at the end of the street, the home offers added privacy while still being close to town amenities. Inside, you’ll find spacious rooms filled with natural light, beautiful hardwood floors, and a traditional floor plan. The second-floor bedrooms have already been gutted, insulated, and drywalled, giving you a head start on the renovations. Currently used as a rental, the property offers flexibility whether you’re looking for a primary residence, investment, or pro

$200,000

4 beds1.5 baths1,482 sq ft

9 Fairview St, Springfield, VT 05156

In-ground pool • Added privacy • Inviting porches

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
Charming 4 bedroom farmhouse with attached barn/garage with lots of overhead storage is located across the road from the scenic Ottauquechee River. Minutes from Woodstock Village Green with all of its amenities and a short distance from Killington with its world renown Ski Resort. Year round activities abound ! The house has a sunny eat in kitchen, spacious dining room and a living room complete with a wood burning fireplace. A bedroom and full bath on the first floor adds to convenience of living . The charming front porch with views of Killington is a lovely place to enjoy relaxing and entertaining friends . Make an appointment today to view this lovely property .

$439,000

4 beds2 baths1,617 sq ft

5798 W Woodstock Rd, Woodstock, VT 05091

Attached barn • Spacious dining room • Sunny eat in kitchen

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
Your Vermont Mountain Retreat Awaits Discover 127 acres of pure Vermont beauty at the foot of Okemo Mountain, just 2 minutes from downtown Ludlow. This rare property offers expansive meadows, forested trails, and panoramic views of Okemo, Mount Ascutney and beyond. Enjoy direct access to cross country skiing, hiking, snowshoeing, the VAST trail system, and year-round outdoor adventure. The updated finished 3150 square ft 4 bedroom house with bonus rooms and barn is move-in ready. Perfect for your full-time home, vacation getaway, or guest house while you build your dream retreat elsewhere on the property. This is a once-in-a-lifetime chance to own one of Ludlow's last large undeveloped parc

$5,500,000

4 beds2 baths3,150 sq ft

85 Pallottas Hill Rd, Ludlow, VT 05149

Renovated farmhouse • Custom storage • Panoramic vistas

ABOUT THIS HOME
Home with Basement for sale in Windsor County, VT:
Endless Possibilities Await – Antique Home with Charm & Character. If you have an eye for potential, this charming antique home is your canvas. Bursting with character and nestled in one of the most desirable towns in Vermont's Upper Valley, it offers a rare opportunity to create something truly special. With plenty of space to design not just one, but two master suites—one on the main floor and another upstairs complete with a private balcony overlooking a babbling brook—this home invites creativity and vision. Wake up with your morning coffee surrounded by the lush, vibrant foliage Vermont is famous for. Set in a close-knit community known for its welcoming spirit,

$165,000

3 beds1 bath1,554 sq ft

89 route 12, Hartland, VT 05048

Two master suites • Private balcony • Babbling brook

Property at 3 Chester Rd, Springfield, VT 05156, 3 beds, 1 bath

$165,000

3 beds1 bath1,704 sq ft

3 Chester Rd, Springfield, VT 05156

Property at 66 Webster Rd, Hartland, VT 05048, 3 beds, 2.5 baths

$349,000

3 beds2.5 baths2,104 sq ft

66 Webster Rd, Hartland, VT 05048

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

$424,900

3 beds2 baths1,288 sq ft

31 Lakota Rd, Barnard, VT 05031

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 1312 Macintosh Hill Rd, Randolph, VT 05060, 5 beds, 2 baths

$795,000

5 beds2 baths2,500 sq ft

1312 Macintosh Hill Rd, Randolph, VT 05060

Property at 1500 Brownsville Hartland Rd, West Windsor, VT 05089, 2 beds, 1 bath

$115,000

2 beds1 bath720 sq ft

1500 Brownsville Hartland Rd, West Windsor, VT 05089

Property at 1004 Jericho Rd, White River Junction, VT 05001, 3 beds, 3.5 baths

$799,000

3 beds3.5 baths2,529 sq ft

1004 Jericho Rd, White River Junction, VT 05001

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 40 Union St, White River Junction, VT 05001, 4 beds, 2 baths

$329,000

4 beds2 baths1,373 sq ft

40 Union St, White River Junction, VT 05001

Property at 696 Route 100 N, Ludlow, VT 05149, 2 beds, 1 bath

$415,000

2 beds1 bath1,100 sq ft

696 Route 100 N, Ludlow, VT 05149

Property at 8 Okemo Acres Rd, Ludlow, VT 05194, 3 beds, 3.5 baths

$1,050,000

3 beds3.5 baths2,390 sq ft

8 Okemo Acres Rd, Ludlow, VT 05194

Property at 1668 Hartford Ave, Hartford, VT 05001, 4 beds, 2 baths

$379,000

4 beds2 baths1,296 sq ft

1668 Hartford Ave, Hartford, VT 05001

Property at 1979 N Hill Rd, Chester, VT 05143, 3 beds, 2 baths

$429,000

3 beds2 baths1,872 sq ft

1979 N Hill Rd, Chester, VT 05143

Property at 56 Grace Dr, North Springfield, VT 05150, 3 beds, 3 baths

$299,000

3 beds3 baths1,260 sq ft

56 Grace Dr, North Springfield, VT 05150

Property at 28 Fairview Ter, South Royalton, VT 05068, 3 beds, 2.5 baths

$530,000

3 beds2.5 baths4,020 sq ft

28 Fairview Ter, South Royalton, VT 05068

Property at 187 Hopson Rd, Norwich, VT 05055, 4 beds, 2.5 baths

$1,495,000

4 beds2.5 baths2,710 sq ft

187 Hopson Rd, Norwich, VT 05055

Property at 22 Birchwood Dr, Perkinsville, VT 05151, 3 beds, 2 baths

$435,000

3 beds2 baths1,440 sq ft

22 Birchwood Dr, Perkinsville, VT 05151

Property at 37 South St, Woodstock, VT 05091, 3 beds, 2 baths

$785,000

3 beds2 baths1,660 sq ft

37 South St, Woodstock, VT 05091

Property at 447 Elm St, Chester, VT 05143, 3 beds, 2 baths

$369,000

3 beds2 baths1,488 sq ft

447 Elm St, Chester, VT 05143

Property at 1514 South Rd, Woodstock, VT 05091, 3 beds, 2 baths

$595,000

3 beds2 baths1,920 sq ft

1514 South Rd, Woodstock, VT 05091

Property at 454 Gidding St, North Springfield, VT 05150

$210,000

— beds— baths3,950 sq ft

454 Gidding St, North Springfield, VT 05150

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

$850,000

4 beds3.5 baths2,970 sq ft

1877 Willard Rd, Hartford, VT 05059

Property at 4074 Tichenor Rd #4074, Hartford, VT 05059, 4 beds, 3 baths

$1,350,000

4 beds3 baths2,277 sq ft

4074 Tichenor Rd #4074, Hartford, VT 05059

Property at 4071 Tichenor Rd #4071, Hartford, VT 05059, 5 beds, 4.5 baths

$1,675,000

5 beds4.5 baths3,837 sq ft

4071 Tichenor Rd #4071, Hartford, VT 05059

Property at 4070 Tichenor Rd #4070, Hartford, VT 05059, 3 beds, 4.5 baths

$1,495,000

3 beds4.5 baths3,120 sq ft

4070 Tichenor Rd #4070, Hartford, VT 05059

Property at 289 Taft Family Rd #7118, Hartford, VT 05059, 3 beds, 2.5 baths

$1,199,000

3 beds2.5 baths1,608 sq ft

289 Taft Family Rd #7118, Hartford, VT 05059

Property at 7074 Robert Frost Ln #7074, Hartford, VT 05059, 5 beds, 4 baths

$1,625,000

5 beds4 baths3,837 sq ft

7074 Robert Frost Ln #7074, Hartford, VT 05059

Property at 5677 Hendee Way #5677, Hartford, VT 05059, 4 beds, 4 baths

$1,525,500

4 beds4 baths2,752 sq ft

5677 Hendee Way #5677, Hartford, VT 05059

Property at 158 Macintosh Hill Rd, Bethel, VT 05032, 3 beds, 2 baths

$399,000

3 beds2 baths2,446 sq ft

158 Macintosh Hill Rd, Bethel, VT 05032

Property at 152 Parkview Rd, Springfield, VT 05156, 3 beds, 3 baths

$685,000

3 beds3 baths3,589 sq ft

152 Parkview Rd, Springfield, VT 05156

Property at 46 Runnals Rd, White River Junction, VT 05001, 4 beds, 4 baths

$585,000

4 beds4 baths3,934 sq ft

46 Runnals Rd, White River Junction, VT 05001

Property at 115 Bethel Mountain Rd, Rochester, VT 05767, 5 beds, 3 baths

$299,900

5 beds3 baths3,684 sq ft

115 Bethel Mountain Rd, Rochester, VT 05767

Property at 891 Route 100, Weston, VT 05161, 2 beds, 1 bath

$245,000

2 beds1 bath864 sq ft

891 Route 100, Weston, VT 05161

Property at 436 Mountain View Loop, Rochester, VT 05767, 3 beds, 1.5 baths

$299,000

3 beds1.5 baths1,248 sq ft

436 Mountain View Loop, Rochester, VT 05767

Property at 60 Fletcher Ln, Hartford, VT 05059, 3 beds, 2.5 baths

$399,000

3 beds2.5 baths1,918 sq ft

60 Fletcher Ln, Hartford, VT 05059

Property at 157 Dartt Hill Rd, Bethel, VT 05032, 5 beds, 3 baths

$949,000

5 beds3 baths2,807 sq ft

157 Dartt Hill Rd, Bethel, VT 05032

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Homes with Basements for Sale in Windsor County

There are currently 249 homes with basements for sale in Windsor County at a median listing price of $550K. 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 100 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 86 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 94 condos, 4 townhouses, and 27 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 Wed Dec 10 2025 on the search page

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