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

244 homes

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ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Nestled on 10 private acres between the towns of Chester and Springfield Vermont, this property offers an exceptional opportunity to build your dream home in a peaceful country setting. A driveway has already been installed, providing easy access to the center of the property where several potential homesites offer the possibility of beautiful mountain and valley views with selective clearing. An existing trailer on the property provides a convenient place to live or use as a base while planning and constructing your new home. With a blend of privacy, natural beauty, and existing improvements, this property is ready for you to bring your vision to life while remaining just minutes from shop

$225,000

3 beds2 baths1,500 sq ft

3781 Flamstead Rd, Chester, VT 05143

Wood sided bathtub • Cedar wall panelling • 10.02 acre lot

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Located just 10 minutes from downtown Ludlow’s vibrant shopping and dining, and the world class slopes of Okemo Mountain, this property delivers the ultimate year round Vermont lifestyle. Escape to Your Cozy Southern Vermont Sanctuary Nestled in charming Cavendish. This 3 bedroom home seamlessly blends rustic character with modern comfort. Inside, gather around the wood burning stove or prepare delicious meals in the fully equipped kitchen featuring the farmhouse sink. The thoughtful layout offers flexible living with a main floor bedroom and bath alongside two bedrooms and a full bathroom upstairs. Outside you will find a carport with attached shed for plenty of storage, keep the woo

$415,000

3 beds2 baths1,864 sq ft

112 Johnson Rd, Proctorsville, VT 05153

Farmhouse sink • Fire pit • Wood burning stove

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
This charming Craftsman-style home is full of original character, solid craftsmanship, and endless potential. With great bones and years of careful maintenance, it's ready for its next owner to restore it to its former glory. While some cosmetic updates and unfinished projects remain, the home's original details shine through, including beautiful woodwork and the signature central staircase. Currently listed with a ¾ bath and a ½ bath, the home is actually plumbed for three bathroom locations, with the beginnings of a full bathroom having been started on the 2nd floor. The flexible floor plan presents a variety of possibilities. A separate entrance provides the opportunity to

$260,000

4 beds1.5 baths1,529 sq ft

32 Hartness Ave, Springfield, VT 05156

Central staircase • Solid craftsmanship • Eat-in kitchen

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Convenient Slopeside Location! Jackson Gore Inn, Unit 453 QIII. Quarter Ownership - thirteen deeded weeks per year. This one-bedroom slopeside residence has a top floor location featuring beautiful slope views! With a sleeper sofa and wall bed in the living room and a king bed in the master, this unit sleeps six. Conveniently located near the north elevator, with streamlined access to the Roundhouse and the Jackson Gore Courtyard. Other features include a large master bath offering his and her sinks, gas fireplace in the living area and a fully-equipped kitchen. The entry foyer provides extra space for all your gear. Unit B Features: 1 Bedroom with King bed, Queen sleep sofa, Queen wall bed

$69,000

1 bed2 baths775 sq ft

453 Qtr. I I I Jackson Gore Inn, Ludlow, VT 05149

His and her sinks • Gas fireplace • Slope views

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
This studio sleeps four with a Queen bed and a Queen sleep sofa. The galley kitchen is fully equipped. The full bath has jetted bath tub/shower. Enjoy the ambiance of a gas fireplace along with a nice view looking up the Jackson Gore Peak. A underground, heated parking spot along with access to all Jackson Gore amenities is included.

$62,000

Studio1 bath390 sq ft

219 Qtr. I V Jackson Gore Inn, Ludlow, VT 05149

Underground parking • Galley kitchen • Access to amenities

Property at 17 Clement Rd, Springfield, VT 05156, 3 beds, 1.5 baths

$99,000

3 beds1.5 baths1,185 sq ft

17 Clement Rd, Springfield, VT 05156

Property at 434 Qtr. I I I Jackson Gore Inn, Ludlow, VT 05149, 1 bed, 2 baths

$67,000

1 bed2 baths775 sq ft

434 Qtr. I I I Jackson Gore Inn, Ludlow, VT 05149

Property at 109 Okemo Ridge Rd Unit C-307, Ludlow, VT 05149, 1 bed, 1 bath

$355,000

1 bed1 bath599 sq ft

109 Okemo Ridge Rd Unit C-307, Ludlow, VT 05149

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

$350,000

4 beds3 baths2,180 sq ft

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

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

$450,000

3 beds2 baths1,308 sq ft

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

Property at 136 Store Hill Rd, Bethel, VT 05032, 3 beds, 2 baths

$130,000

3 beds2 baths1,359 sq ft

136 Store Hill Rd, Bethel, VT 05032

Property at 1440 Stevens Rd, Bridgewater Corners, VT 05035, 1 bed

$199,000

1 bed— baths448 sq ft

1440 Stevens Rd, Bridgewater Corners, VT 05035

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

$349,000

4 beds2 baths1,617 sq ft

5798 W Woodstock Rd, Woodstock, VT 05091

Property at 81 Main St, Chester, VT 05143, 5 beds, 4 baths

$445,000

5 beds4 baths3,865 sq ft

81 Main St, Chester, VT 05143

Property at 185 Wall St, Springfield, VT 05156, 3 beds, 1.5 baths

$249,000

3 beds1.5 baths1,551 sq ft

185 Wall St, Springfield, VT 05156

Property at 126 Red Bridge Rd, Ludlow, VT 05149, 1.5 baths

$405,000

Studio1.5 baths— sq ft

126 Red Bridge Rd, Ludlow, VT 05149

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 145 Okemo Trailside Ext Unit 23BL, Ludlow, VT 05149, 1 bed, 1 bath

$349,000

1 bed1 bath884 sq ft

145 Okemo Trailside Ext Unit 23BL, Ludlow, VT 05149

Property at 99 Heather Dr Unit 8F, White River Junction, VT 05001, 2 beds, 1.5 baths

$345,000

2 beds1.5 baths1,225 sq ft

99 Heather Dr Unit 8F, White River Junction, VT 05001

Property at 1144 Potash Brook Rd, Chester, VT 05143, 2 beds, 1 bath

$75,000

2 beds1 bath620 sq ft

1144 Potash Brook Rd, Chester, VT 05143

Property at 421 QIV Jackson Gore Inn Unit 421 Q4, Ludlow, VT 05149, 1 bath

$63,000

Studio1 bath496 sq ft

421 QIV Jackson Gore Inn Unit 421 Q4, Ludlow, VT 05149

Property at 2055 & 2071 Main & 28 Pleasant St, Cavendish, VT 05142, 7 beds, 2 baths

$399,000

7 beds2 baths2,496 sq ft

2055 & 2071 Main & 28 Pleasant St, Cavendish, VT 05142

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 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 466 Estey Ln, Windsor, VT 05089, 2 beds, 1 bath

$299,000

2 beds1 bath1,152 sq ft

466 Estey Ln, Windsor, VT 05089

Property at 501 Stoughton Pond Rd, Perkinsville, VT 05151, 3 beds, 2.5 baths

$415,000

3 beds2.5 baths1,558 sq ft

501 Stoughton Pond Rd, Perkinsville, VT 05151

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 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 445 Old Quechee Rd Unit 10C, Quechee, VT 05059, 2 beds, 1.5 baths

$230,000

2 beds1.5 baths1,063 sq ft

445 Old Quechee Rd Unit 10C, Quechee, VT 05059

Property at 4 Pine Brook Ln, North Springfield, VT 05150, 3 beds, 2 baths

$245,000

3 beds2 baths1,234 sq ft

4 Pine Brook Ln, North Springfield, VT 05150

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

$235,000

2 beds1 bath832 sq ft

574 Willard Rd Unit 2C, Hartford, VT 05059

Property at 2940 Route 103 #254, Cavendish, VT 05142, 1 bed, 1 bath

$175,000

1 bed1 bath675 sq ft

2940 Route 103 #254, Cavendish, VT 05142

Property at 4 Pine Brook Ln Apt B6, North Springfield, VT 05150, 3 beds, 2 baths

$275,000

3 beds2 baths1,234 sq ft

4 Pine Brook Ln Apt B6, North Springfield, VT 05150

Property at 31 Amsden Hollow Rd, Perkinsville, VT 05151, 3 beds, 2 baths

$99,900

3 beds2 baths2,321 sq ft

31 Amsden Hollow Rd, Perkinsville, VT 05151

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 240 Qtr. I I Jackson Gore Inn, Ludlow, VT 05149, 1 bath

$55,000

Studio1 bath390 sq ft

240 Qtr. I I Jackson Gore Inn, 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 36 Okemo Trailside Ext Unit 6D, Ludlow, VT 05149, 1 bed, 1 bath

$315,000

1 bed1 bath858 sq ft

36 Okemo Trailside Ext Unit 6D, Ludlow, VT 05149

Property at 139 Pleasant Valley Rd, Springfield, VT 05156, 3 beds, 1 bath

$279,000

3 beds1 bath1,331 sq ft

139 Pleasant Valley Rd, Springfield, VT 05156

Property at 122 Quechee Hollow Ln Unit 4A, Quechee, VT 05059, 1 bed, 1 bath

$225,000

1 bed1 bath720 sq ft

122 Quechee Hollow Ln Unit 4A, Quechee, VT 05059

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

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Cheap Homes for Sale in Windsor County

There are currently 244 cheap homes 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 92 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 102 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 113 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 Mon Nov 09 2026 on the search page

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