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

223 homes

Sort:

Recommended

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
This home truly checks all the boxes and what could be better than deciding on a new home just in time for the holidays? Thoughtfully set back from the road, the property offers expansive front and back yards, creating a sense of privacy and space. The two-car garage features automatic openers and an impressive workshop above with power. It is currently used for woodturning, but equally ideal for a private work-from-home office or creative studio, separate from the main living areas. Enjoy the convenience of a fully covered entry from the garage to the house; no snow shoveling required. Inside, a generous mudroom provides the perfect drop zone for boots and coats before leading into a brigh

$375,000

3 beds2 baths1,500 sq ft

400 Melody Ln, Springfield, VT 05030

Bright kitchen • Generous mudroom • Fully covered entry

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
This 2-bedroom Sugarhill Condo, perched up at the top of the hill, is a beautiful, bright, and peaceful place to be. With a large deck out back, you can enjoy this lovely time of year and see the ridgeline through the trees. As you step inside, the tile in the entryway is the perfect touch for all the seasons Vermont offers. The open-concept first-floor living room is an excellent space for families to gather and sit in front of the wood-burning fireplace after a day of enjoying all the Quechee Lakes amenities. The updated kitchen adds a warm, welcoming feel to the home. Upstairs, the cozy two bedrooms share a full bathroom, each with its own individual vanity. The large walk-in closet is a

$345,000

2 beds1.5 baths1,472 sq ft

291 Sugarhill Ln Unit 1B, Hartford, VT 05059

Large deck • Updated kitchen • Large walk-in closet

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
A Rare Find. .. 1 bedroom condominium at Castle Point, only 3 miles to Okemo Mountain Resort. This condo can be rented out or used whenever you like, it is a full ownership property and fully furnished. It is located in the back away from the hotel lobbies, but has access to the pool and gym facilities. On the first floor the condo has an open living room with a gas fireplace, dining room, and a kitchen with a primary bedroom/bath to the side. Easy maintenance with the HOA fees and front desk offering service to your potential tenants. Close to skiing, boarding, snowmobiling shops and restaurants.

$210,000

1 bed1 bath675 sq ft

2940 Route 103 #158, Cavendish, VT 05142

Open living room • Gas fireplace • Access to pool

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
This well-priced home is full of potential and ready for your cosmetic upgrades and a bit of sweat equity. Offering three bedrooms and two baths on a generous lot, it’s conveniently located near the hospital, shopping, and essential amenities. The spacious master bedroom features an ensuite bath, while the additional partially finished attic provides room for expansion or storage. Enjoy relaxing mornings and evenings on the grand wrap-around porch. A two-car garage and a new boiler add valuable practicality and peace of mind. With great bones and outstanding features, this is an excellent opportunity for affordable home ownership. OPEN HOUSE Sunday, Dec 14 11 am - 1 pm. Come and take

$199,000

3 beds2 baths1,792 sq ft

95 Union St, Springfield, VT 05156

New boiler • Wrap-around porch • 0.38 acre lot

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Come, enjoy the quiet charm of Andover in this inviting, private Vermont home—perfect for year-round living or a peaceful getaway. Nestled among evergreens with beautiful snowy views, this property offers easy access to Okemo Mountain, and is also close to Stratton, Magic, and Bromley for skiing, riding, and four-season adventure. Snowmobile enthusiasts will love the nearby VAST trails, and the villages of Chester, Weston, and Londonderry are just minutes away. The home has been thoughtfully updated with a brand-new 5-bedroom septic system, new well pump, and efficient heat pumps, giving you comfort and peace of mind. A standout feature is the very private sun deck, ideal for morning

$369,000

5 beds1 bath2,243 sq ft

2029 N Hill Rd, Chester, VT 05143

Private vermont home • Modern upgrades • Nearby vast trails

Property at 339 Ranney Rd, Stockbridge, VT 05772, 3 beds, 2.5 baths

$449,000

3 beds2.5 baths2,200 sq ft

339 Ranney Rd, Stockbridge, VT 05772

Property at 1846 Dartt Hill Rd, Bethel, VT 05032, 3 beds, 2 baths

$369,000

3 beds2 baths1,911 sq ft

1846 Dartt Hill Rd, Bethel, VT 05032

Property at 724 S Windsor St, South Royalton, VT 05068, 3 beds, 2 baths

$349,000

3 beds2 baths1,453 sq ft

724 S Windsor St, South Royalton, VT 05068

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 145 Main St #212, Ludlow, VT 05149, 2 beds, 1.5 baths

$220,000

2 beds1.5 baths1,019 sq ft

145 Main St #212, Ludlow, VT 05149

Property at 79 Merrill St, Springfield, VT 05156, 4 beds, 2.5 baths

$199,000

4 beds2.5 baths2,048 sq ft

79 Merrill St, Springfield, VT 05156

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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 58 Depot St, Chester, VT 05153, 4 beds, 2 baths

$249,000

4 beds2 baths2,016 sq ft

58 Depot St, Chester, VT 05153

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

$261,250

5 beds3 baths3,684 sq ft

115 Bethel Mountain Rd, Rochester, VT 05767

Property at 505 Back Mountain Rd #14, Windsor, VT 05089, 1 bed, 1 bath

$129,000

1 bed1 bath240 sq ft

505 Back Mountain Rd #14, Windsor, VT 05089

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 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 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 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 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 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 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 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 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

Viewing page 1 of 6

Cheap Homes for Sale in Windsor County

There are currently 223 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, 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.

More real estate resources for Windsor County, VT

Nearby Counties

Cities

Nearby Counties with Cheap Homes

Nearby Cities with Cheap Homes

More to explore in Windsor County, VT

How to buy a house in Windsor County, VT

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Vermont

Burlington homes for sale
$559,000
Stowe homes for sale
$1,124,500
Woodstock homes for sale
$1,195,000
Montpelier homes for sale
$350,000
Brattleboro homes for sale
$360,000
South Burlington homes for sale
$696,580
Shelburne homes for sale
$549,900
Waterbury homes for sale
$399,000
Rutland homes for sale
$275,000
Ludlow homes for sale
$595,000
Manchester homes for sale
$1,300,000
Middlebury homes for sale
$482,500
Barre homes for sale
$272,000
Bennington homes for sale
$272,000
Norwich homes for sale
$0

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 Sat Dec 27 2025 on the search page

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.