Cheap homes for sale & real estate in Windsor County, VT

217 homes

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ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Take a look at this home in mid-Vermont- close to the premier Killington Mountain Ski Resort. This property is on an open 2 acre lot with plenty of sun and space for pets, gardens or greenhouses. An adjoining 1 acre house lot can be purchased for an additional 30k if interested now. This Stockbridge home has an extra living apartment below- accessible by a separate driveway. It provides options for extended family, renters or vacationers, and allows space for ski vacationers to spread out or mom and pop to have privacy. While technically it's a 2 bedroom, the layout could accommodate 6-8 with a little creativity. Or make it your forever home in the heart of Vermont with small towns Stockbri

$449,000

2 beds2.5 baths2,200 sq ft

339 Ranney Rd, Stockbridge, VT 05772

Open 2 acre lot • Separate driveway • 2.2 acre lot

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
1978 Saltbox on 10 acres of both open and wooded land. The home boasts wide plank floors throughout with 3 bedrooms, 2 baths, open floor plan on the main floor with spacious kitchen. A lovely home, a must see.

$369,000

3 beds2 baths1,911 sq ft

1846 Dartt Hill Rd, Bethel, VT 05032

Open floor plan • Spacious kitchen • 10 acres

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ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Downtown Ludlow Convenience - Welcome to Mill #212, a beautifully updated condo in the heart of Ludlow. Just minutes to Okemo Mountain and directly on the shuttle route, this furnished unit combines comfort with convenience. Inside, you’ll find exposed beams, modern updates throughout, and an open living space that flows seamlessly to a private deck overlooking the Black River. Enjoy the ease of being steps from shops, dining, and village amenities while still feeling tucked away. With a proven rental history, this home offers excellent rental potential as well as a perfect Vermont retreat. Visit the Okemo real estate community today. Taxes are based on the town assessment.

$220,000

2 beds1.5 baths1,019 sq ft

145 Main St #212, Ludlow, VT 05149

Private deck • Rental potential • Steps from shops

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Opportunity awaits! This property offers incredible potential and appears to have solid, well-maintained bones. The home showcases a wealth of original woodwork, including beautiful hardwood floors throughout the first level. Many newer windows and updated appliances enhance both comfort and appeal. While the main house could benefit from some cosmetic TLC, it features 3–4 bedrooms and 2 bathrooms, plus a studio apartment above the 1-car garage/workshop. Live in the home and rent out the apartment for extra income, perfect for offsetting your mortgage while you make improvements. A second outbuilding provides additional storage, making this property even more versatile. Property is be

$199,000

4 beds2.5 baths2,048 sq ft

79 Merrill St, Springfield, VT 05156

Updated appliances • Outbuilding • Newer windows

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Welcome to this beautifully updated Central Vermont home offering excellent potential as a primary residence or investment opportunity. This versatile property is ideally located less than 1 mile to Vermont Law School and just 0.5 miles to WRV Elementary and High Schools. Enjoy walking distance to the Village Green with year-round farmers markets and community events. The half-acre property features mature lilacs, a manicured lawn, and inviting firepit. The fully fenced backyard with deck provides perfect indoor-outdoor entertaining space. Step into the light-filled living area with vaulted ceilings and sliding glass doors opening to the deck. The open flow continues to the dining area and

$349,000

3 beds2 baths1,453 sq ft

724 S Windsor St, South Royalton, VT 05068

Private balcony • Inviting firepit • Vaulted ceilings

Property at 2029 N Hill Rd, Chester, VT 05143, 5 beds, 1 bath

$369,000

5 beds1 bath2,243 sq ft

2029 N Hill Rd, Chester, VT 05143

Property at 531 Main St, Chester, VT 05143, 3 beds, 1 bath

$425,000

3 beds1 bath1,608 sq ft

531 Main St, Chester, VT 05143

Property at 2940 Route 103 #158, Cavendish, VT 05142, 1 bed, 1 bath

$210,000

1 bed1 bath675 sq ft

2940 Route 103 #158, Cavendish, VT 05142

Property at 789 Ski Tow Rd #3, Brownsville, VT 05037, 1 bed, 1 bath

$147,500

1 bed1 bath602 sq ft

789 Ski Tow Rd #3, Brownsville, VT 05037

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

$165,000

3 beds1 bath1,554 sq ft

89 route 12, Hartland, VT 05048

Property at 6120 Vermont Route 106, Weathersfield, VT 05151, 3 beds, 2 baths

$275,000

3 beds2 baths960 sq ft

6120 Vermont Route 106, Weathersfield, VT 05151

Property at 1806 Route 100 S, Rochester, VT 05767, 4 beds, 2 baths

$399,000

4 beds2 baths2,554 sq ft

1806 Route 100 S, Rochester, VT 05767

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

$280,000

5 beds3 baths3,474 sq ft

223 Route 100 S, Ludlow, VT 05149

Property at 318/320 Qtr. I Jackson Gore Inn, Ludlow, VT 05149, 1 bed, 2 baths

$69,000

1 bed2 baths775 sq ft

318/320 Qtr. I Jackson Gore Inn, Ludlow, VT 05149

Property at 42 Heritage Condo Way Unit 14D, Woodstock, VT 05091, 1 bed, 1 bath

$230,000

1 bed1 bath856 sq ft

42 Heritage Condo Way Unit 14D, Woodstock, VT 05091

Property at 402 Marsh Family Rd, Hartford, VT 05047, 2 beds, 2.5 baths

$399,000

2 beds2.5 baths2,332 sq ft

402 Marsh Family Rd, Hartford, VT 05047

Property at 253 Old Quechee Rd Unit 6D, White River Junction, VT 05059, 2 beds, 1.5 baths

$219,000

2 beds1.5 baths1,063 sq ft

253 Old Quechee Rd Unit 6D, White River Junction, VT 05059

Property at 103 Bear Hill Rd W, Ludlow, VT 05149, 1 bed, 1 bath

$299,000

1 bed1 bath320 sq ft

103 Bear Hill Rd W, Ludlow, VT 05149

Property at 25 Wilder Ln, Bethel, VT 05032-9181, 3 beds, 2 baths

$169,500

3 beds2 baths1,140 sq ft

25 Wilder Ln, Bethel, VT 05032-9181

Property at 46 Ledgeside Ter, White River Junction, VT 05001, 2 beds, 1 bath

$150,000

2 beds1 bath1,296 sq ft

46 Ledgeside Ter, White River Junction, VT 05001

Property at 1163 Baker Turn Rd Unit 2E, Hartford, VT 05059, 2 beds, 1.5 baths

$374,000

2 beds1.5 baths1,320 sq ft

1163 Baker Turn Rd Unit 2E, Hartford, VT 05059

Property at 106 Contro Rd, Chester, VT 05143, 2 beds, 2.5 baths

$289,000

2 beds2.5 baths1,475 sq ft

106 Contro Rd, Chester, VT 05143

Property at 36 Juniper Dr Unit 6B, White River Junction, VT 05001, 2 beds, 1.5 baths

$329,000

2 beds1.5 baths1,225 sq ft

36 Juniper Dr Unit 6B, White River Junction, VT 05001

Property at 4351 Vermont RT 11 W, Chester, VT 05143, 2 beds, 1 bath

$149,900

2 beds1 bath1,120 sq ft

4351 Vermont RT 11 W, Chester, VT 05143

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 722 fairview Ter, White River Junction, VT 05001, 3 beds, 1 bath

$290,000

3 beds1 bath1,536 sq ft

722 fairview Ter, White River Junction, VT 05001

Property at 291 Sugar Hill Ln Unit 1B, Hartford, VT 05059, 2 beds, 1.5 baths

$345,000

2 beds1.5 baths1,472 sq ft

291 Sugar Hill Ln Unit 1B, Hartford, VT 05059

Property at 3019 Popple Dungeon Rd, Chester, VT 05143, 1 bed, 1 bath

$169,000

1 bed1 bath200 sq ft

3019 Popple Dungeon Rd, Chester, VT 05143

Property at 454 Giddings St, North Springfield, VT 05150

$210,000

— beds— baths3,950 sq ft

454 Giddings St, North Springfield, VT 05150

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

$399,000

5 beds3.5 baths2,200 sq ft

109 Park Row, Rochester, VT 05767

Property at 107 Blueberry Ledge Rdg Unit L-45, Plymouth, VT 05056, 3 beds, 2 baths

$399,800

3 beds2 baths1,428 sq ft

107 Blueberry Ledge Rdg Unit L-45, Plymouth, VT 05056

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 105 Williams LN Unit 7f, Hartford, VT 05059, 3 beds, 2.5 baths

$435,000

3 beds2.5 baths1,352 sq ft

105 Williams LN Unit 7f, Hartford, VT 05059

Property at 224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149, 2 beds, 2 baths

$95,000

2 beds2 baths1,025 sq ft

224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149

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 143 Spoonerville Rd, Springfield, VT 05150, 3 beds, 2 baths

$369,000

3 beds2 baths1,320 sq ft

143 Spoonerville Rd, Springfield, VT 05150

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

$369,000

3 beds2 baths1,488 sq ft

447 Elm St, Chester, VT 05143

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Cheap Homes for Sale in Windsor County

There are currently 217 cheap homes 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 102 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 87 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 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 Thu Jan 01 2026 on the search page

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