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

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ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area — a practical entryway for Vermont living. The open kitchen and dining area provide plenty of room for gatherings, while the cozy living room invites relaxation after a long day. A full bathroom completes the main level for easy accessibility. Upstairs, you’ll find three comfortable bedrooms filled with natural light. The attached back barn offers exciting potenti

$425,000

3 beds1 bath1,608 sq ft

531 Main St, Chester, VT 05143

Attached back barn • Spacious mudroom • Fire pit

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Much more here than meets the eye. This home had heating efficiency completed with SEVCA, new siding, new hot water heater, chimney and furnace inspected and some new exterior paint. Nice level yard, attached two car garage PLUS detached barn! Close to downtown Chester and 15 minutes to Ludlow and Okemo/Vail resort. There is a large 3-season porch, two spacious bedrooms and large country kitchen. This little gem is just waiting for a little polish and it will make a wonderful home. Easy to view, improvements are listed in documents.

$239,000

2 beds1 bath1,222 sq ft

1374 VT Route 103 N, Chester, VT 05143

New siding • New exterior paint • Chimney inspected

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Experience Vermont's Premier Mountain Living Without Full Ownership Costs. Step directly onto Okemo's slopes from your slopeside retreat at Jackson Gore. This condo-tel quarter-share gives you deeded ownership of 13 weeks annually (25% of the year)—at a fraction of the cost of whole ownership. You own one of four deeded interests in this unit. You receive every fourth week on a rotating schedule, guaranteeing time across all seasons: winter ski weeks plus spring, summer, and fall. The rotation ensures fair distribution—over time, every owner enjoys premium holidays. Use your weeks or place them in the rental program. This isn't a timeshare—it's real property with a deed, a

$95,000

2 beds2 baths1,025 sq ft

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

Full kitchen • Gas fireplace • Jetted tub

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Opportunity Knocks! Bring Your Vision and Sweat Equity Discover the potential in this 3-bedroom, 1-bath single-level home, perfectly primed for your cosmetic upgrades. Major systems are already taken care of, including a brand-new boiler, oil tank, electrical panel, kitchen appliances, and a new sewer line from the house to town services. A huge head start for any buyer. The walkout basement offers even more possibilities, already framed for a family room, office, and additional bathroom. Whether you’re looking to expand your living space, potential to add a second unit, or create a home office setup, the groundwork is done. Conveniently located close to the VA and downtown White Riv

$290,000

3 beds1 bath1,536 sq ft

722 fairview Ter, White River Junction, VT 05001

New boiler • Walkout basement • New oil tank

3D WALKTHROUGH

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the Jiffy Mart and the General Dollar Store, there are many possibilities here for a commercial enterprise. Or you can use one unit for a nice business office and continue to rent the other two existing apartments. Presently, all three units are vacant. Easy to show! There is good road frontage for plenty of parking. Consider the options here and take a look today!

$299,000

— beds— baths2,702 sq ft

41 VT Route 103 S, Chester, VT 05143

Main street location • Plenty of parking • Good road frontage

Property at 713/715 Qtr. I I I Adams House, Ludlow, VT 05149, 3 beds, 3 baths

$210,000

3 beds3 baths2,001 sq ft

713/715 Qtr. I I I Adams House, Ludlow, VT 05149

Property at 336 Piper Hill Rd, Weston, VT 05161, 3 beds, 1.5 baths

$247,000

3 beds1.5 baths1,458 sq ft

336 Piper Hill Rd, Weston, VT 05161

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 228 Cavendish Gulf Rd, Cavendish, VT 05495, 3 beds, 2 baths

$395,000

3 beds2 baths1,312 sq ft

228 Cavendish Gulf Rd, Cavendish, VT 05495

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 29 Markham Ln, Weston, VT 05161, 2 beds, 1 bath

$299,000

2 beds1 bath750 sq ft

29 Markham Ln, Weston, VT 05161

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

$339,900

2 beds1.5 baths1,225 sq ft

36 Juniper Dr Unit 6B, 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 46A Barrister Dr #205, Hartford, VT 05001, 1 bed, 1 bath

$225,000

1 bed1 bath801 sq ft

46A Barrister Dr #205, Hartford, VT 05001

Property at 6-8 Crescent St, Springfield, VT 05156, 6 beds, 3 baths

$126,000

6 beds3 baths2,377 sq ft

6-8 Crescent St, Springfield, VT 05156

Property at 715-717 Giddings St, North Springfield, VT 05150, 8 beds, 4 baths

$249,000

8 beds4 baths3,312 sq ft

715-717 Giddings St, North Springfield, VT 05150

Property at 57 River St, Springfield, VT 05156, 7 beds, 4 baths

$249,000

7 beds4 baths3,294 sq ft

57 River St, Springfield, VT 05156

Property at 37 Dee Haven Ln, Sharon, VT 05065, 4 beds, 2 baths

$299,000

4 beds2 baths1,992 sq ft

37 Dee Haven Ln, Sharon, VT 05065

Property at 51 Merrill St, Springfield, VT 05156, 6 beds, 4 baths

$186,000

6 beds4 baths2,304 sq ft

51 Merrill St, Springfield, VT 05156

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 7 Common St, Springfield, VT 05156, 8 beds, 15 baths

$379,000

8 beds15 baths4,936 sq ft

7 Common St, Springfield, VT 05156

Property at 3 Wall St, Springfield, VT 05156, 4 beds, 4 baths

$249,000

4 beds4 baths2,767 sq ft

3 Wall St, Springfield, VT 05156

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 68 Jarvis St, Windsor, VT 05089, 3 beds, 1 bath

$165,000

3 beds1 bath1,602 sq ft

68 Jarvis St, Windsor, VT 05089

Property at 254/256 Qtr. I Jackson Gore Inn, Ludlow, VT 05149, 1 bed, 2 baths

$72,000

1 bed2 baths775 sq ft

254/256 Qtr. I Jackson Gore Inn, Ludlow, VT 05149

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

$175,000

2 beds1 bath1,296 sq ft

46 Ledgeside Ter, White River Junction, VT 05001

Property at 1011 Quechee Hartland Rd, Hartford, VT 05059, 3 beds, 1.5 baths

$450,000

3 beds1.5 baths1,460 sq ft

1011 Quechee Hartland Rd, Hartford, VT 05059

Property at 226 Fellows Hill Rd, Springfield, VT 05156, 3 beds, 1 bath

$79,900

3 beds1 bath1,075 sq ft

226 Fellows Hill Rd, Springfield, VT 05156

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 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 50 Bates Rd, Cavendish, VT 05142, 3 beds, 1 bath

$299,000

3 beds1 bath1,800 sq ft

50 Bates Rd, Cavendish, VT 05142

Property at 215 Elm Hill St, Springfield, VT 05156, 4 beds, 2.5 baths

$379,000

4 beds2.5 baths2,240 sq ft

215 Elm Hill St, Springfield, VT 05156

Property at 418 Qtr. I I I Jackson Gore Inn, Ludlow, VT 05149, 1 bed, 2 baths

$74,000

1 bed2 baths775 sq ft

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

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 1873 Old River Rd, White River Junction, VT 05001, 2 beds, 1 bath

$425,000

2 beds1 bath908 sq ft

1873 Old River 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 238 Q1 Jackson Gore Inn Unit 238 Q1, Ludlow, VT 05149, 2 beds, 2 baths

$95,000

2 beds2 baths1,025 sq ft

238 Q1 Jackson Gore Inn Unit 238 Q1, Ludlow, VT 05149

Property at 15 Frederic St, Springfield, VT 05156, 2 beds, 1 bath

$229,000

2 beds1 bath1,228 sq ft

15 Frederic St, Springfield, VT 05156

Property at 803 Malagash Rd, Reading, VT 05062, 3 beds, 2 baths

$425,000

3 beds2 baths1,540 sq ft

803 Malagash Rd, Reading, VT 05062

Property at 212 QIII Jackson Gore Inn Unit 212 QIII, Ludlow, VT 05149, 1 bath

$55,000

0 beds1 bath390 sq ft

212 QIII Jackson Gore Inn Unit 212 QIII, Ludlow, VT 05149

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Cheap Homes for Sale in Windsor County

There are currently 250 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 89 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 103 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 105 condos, 4 townhouses, and 26 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 Fri Nov 28 2025 on the search page

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