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

250 homes

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ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Updated with fiber internet, new kitchen appliances, a heat pump water heater and mini split. 200 amp breaker- generator ready. Security system provides peace of mind when away with furnace & temperature monitoring, carbon monoxide & smoke detectors, glass breakage and door entry. Partially finished walk out basement. Single car garage built in. Open floor plan living room/dining area with cathedral ceiling and field stone fireplace. Private porch with tree top views. Property is bordered with beautiful stone wall. A short hike behind the house gets you to a seasonal overlook view of Mt. Ascutney. Access to VAST trail from Malagash Road. Located ~20 minutes to Okemo/Ludlow ski a

$425,000

3 beds2 baths1,540 sq ft

803 Malagash Rd, Reading, VT 05062

10 beautiful acres • Vermont log cabin • Open kitchen diner

VIDEO TOUR

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Experience slopeside convenience and resort-style comfort with this studio condominium located at the Jackson Gore Inn on Okemo Mountain. This end unit offers expansive valley and mountain views, creating the perfect year-round getaway. The open-concept layout features a queen bed, a sleep sofa, a gas fireplace, and a full kitchen, making it ideal for relaxing after a day on the slopes or trails. Enjoy the convenience of ski-on/ski-off access, plus a wealth of resort amenities, including a heated outdoor pool and hot tubs, and access to The Spring House—featuring an indoor pool and hot tub, fitness center, and yoga studio. In the warmer months, explore scenic hiking right from your do

$55,000

0 beds1 bath390 sq ft

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

Hot tubs • Heated outdoor pool • Indoor pool

VIDEO TOUR

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Experience the ultimate in mountain living with this top-floor one-bedroom, two-bathroom Jackson Gore Adams House condominium on Okemo Mountain. This quartershare ownership offers you a carefree, luxury resort lifestyle with direct ski-on/ski-off access and all the amenities of Jackson Gore Village. The spacious condo comfortably sleeps eight, featuring two fixed queen beds, a queen wall bed, and a queen sleep sofa, offering great flexibility for owners and guests. The lock-out design allows you to use one side while renting the other for added income potential. Enjoy a jetted bathtub, full kitchen, in-unit washer and dryer, and underground heated parking—everything you need for a rel

$74,000

1 bed2 baths1,011 sq ft

Jackson Gore Adams House Rd Unit 714/716 QIII, Ludlow, VT 05149

Full kitchen • Jetted bathtub • Outdoor hot tubs

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
This well positioned 3 bedroom home is central to skiing, golfing, town amenities, offering easy interstate access to northern and southern points. An updated kitchen includes stainless steel appliances, maple cabinetry, and breakfast bar with stone countertop. A separate dining area leads out to a private side deck through french doors for outdoor entertaining. A patio with firepit adjoins the side deck. The large living room is the perfect gathering space for friends and family. A generous main level bedroom is conveniently located next to one of two full baths. Private upper level layout consists of two well proportioned bedrooms with full bath. A finished lower level family room accente

$425,000

3 beds2 baths1,952 sq ft

41 Reservoir Rd, Springfield, VT 05156

Private side deck • Updated kitchen • Breakfast bar

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Discover this inviting condo in a fantastic location near the top of the ski hill. Nestled in a quiet setting, the home features fresh paint in the living room and kitchen, along with a brand-new stove, refrigerator, microwave, washer, and dryer for modern convenience. Three windows are scheduled for replacement in 2025, Association replaced roofing and siding, and new decks giving you peace of mind for years to come. Seller has paid all Special Assessment fees! Whether you’re seeking a year-round residence or a seasonal getaway, this condo is the perfect place to relax and enjoy everything Quechee has to offer—skiing, golf, hiking, lakes, and a vibrant community atmosphere.

$315,000

2 beds2.5 baths1,344 sq ft

1191 Baker Turn Unit 3C, Hartford, VT 05059

Fresh paint • Brand-new microwave • Quiet setting

Property at 42 Heritage Condo Way #22, Woodstock, VT 05091, 1 bed, 1 bath

$239,000

1 bed1 bath816 sq ft

42 Heritage Condo Way #22, Woodstock, VT 05091

Property at 127 Trombley Rd, Chester, VT 05143, 5 beds, 1 bath

$449,000

5 beds1 bath2,856 sq ft

127 Trombley Rd, 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 1782 Blackmer Blvd, Stockbridge, VT 05772, 2 beds, 1 bath

$425,000

2 beds1 bath1,092 sq ft

1782 Blackmer Blvd, Stockbridge, VT 05772

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

$429,000

4 beds2 baths2,554 sq ft

1806 Route 100 S, Rochester, VT 05767

Property at 111 Acton Pl, South Royalton, VT 05068, 1 bed, 1 bath

$65,000

1 bed1 bath342 sq ft

111 Acton Pl, South Royalton, VT 05068

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 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 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 525 Morgan Rd, Hartford, VT 05059, 2 beds, 2 baths

$390,000

2 beds2 baths1,344 sq ft

525 Morgan Rd, Hartford, VT 05059

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 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 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 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 145 Main St #210, Ludlow, VT 05149, 2 beds, 1 bath

$215,000

2 beds1 bath892 sq ft

145 Main St #210, Ludlow, VT 05149

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

$225,000

2 beds1.5 baths1,063 sq ft

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

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

$399,900

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

$429,000

3 beds2 baths1,428 sq ft

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

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

$389,000

3 beds2 baths1,488 sq ft

447 Elm St, Chester, VT 05143

Property at 454 Gidding St, North Springfield, VT 05150

$410,000

— beds— baths3,950 sq ft

454 Gidding St, North Springfield, VT 05150

Property at 3 Olney St, North Springfield, VT 05150

$410,000

— beds— baths2,381 sq ft

3 Olney St, North Springfield, VT 05150

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 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 221 A Southridge St, Springfield, VT 05156, 1 bed, 1 bath

$199,000

1 bed1 bath708 sq ft

221 A Southridge St, Springfield, VT 05156

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 143 VT Rte 100 S, Ludlow, VT 05149, 3 beds, 2 baths

$295,000

3 beds2 baths864 sq ft

143 VT Rte 100 S, Ludlow, VT 05149

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

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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 Sat Nov 29 2025 on the search page

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