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:
Prime investment opportunity in Wilder, one of Hartford’s five thriving villages. This early-1900s multifamily, minutes from Upper Valley amenities, is ready for redevelopment with significant upside potential. The property features three units offering multiple strategies: renovate and lease all for strong cash flow, or occupy one while offsetting costs with rental income. Its location ensures consistent tenant demand, with recreation at Kilowatt Park, trails, and a boat launch nearby. An ideal project for investors seeking value-add potential in a high-demand market. Showings available now.

$247,000

5 beds3 baths3,100 sq ft

99 Depot St, Hartford, VT 05088

Recreation nearby • Trails • Three units

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
This 3-bedroom, 1-bathroom home sits on a manageable . 10-acre lot and offers the charm of a classic craftsman style. With upgraded electrical and a new water heater, the home is move-in ready while still leaving room for your finishing touches. It needs a little TLC, but the major systems are already in place. Conveniently located close to shopping, dining, and everyday amenities, a great opportunity for a starter home or investment.

$249,000

3 beds1 bath1,140 sq ft

226 N Main St, Bethel, VT 05032

Upgraded electrical • New water heater • Close to dining

VIDEO TOUR

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Jackson Gore area of Okemo– Adams House Quarter Share Ownership, Unit 625/627 Quarter III. Enjoy slopeside living with mountain views in this three-bedroom, three-bathroom condominium with just over 2000 square feet of living space. Located within The Adams House at Jackson Gore on Okemo, offering direct slope access. Enjoy luxury living with full access to The Spring House, which offers an indoor and heated outdoor pool, fitness center, and spa. Other amenities include underground parking, slopeside hot tub, and conveniently located ski lockers, just to name a few. This great open floor plan features a fully equipped kitchen, jetted bathtub, gas fireplace, and lock-out capabilities.

$210,000

3 beds3 baths2,011 sq ft

Jackson Gore Adams House Unit 625/627 Q3, Ludlow, VT 05149

Underground parking • Fitness center • Spa

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
This spacious walk-up condominium features 3 bedrooms and 3 full baths, with an inviting open-concept living and dining area anchored by a cozy fireplace. Step out onto your private deck overlooking the property. This vibrant community offers an unbeatable lifestyle with access to approximately 1,300 acres of outdoor fun, including mountain biking, hiking, cross-country skiing, snowshoeing, and affordable alpine skiing on natural snow. Fees include utilities!! 1726.00 quarterly for association fee and a variable 1163.00 quarterly fee for electric, heat, sewer, trash, water Perfectly situated, you're about 30 minutes from Woodstock, Ludlow, and Okemo, with Killington, Bromley, and

$207,000

3 beds3 baths1,604 sq ft

295 Hotel Rd Unit 10/10A, Brownsville, VT 05037

Private deck • Mountain biking • Cozy fireplace

ABOUT THIS HOME
Cheap Home for sale in Windsor County, VT:
Beautiful Weston! Just 2 miles from the town center, this 3 Bedroom, 2 Bath Ranch style home on 1.5 Acres offers easy access, just off Route 100, with single level living. Enter into a large Sunroom surrounded with windows, giving the feeling of being outdoors year round and enjoy the wonderful Pellet stove. The eat-in Kitchen, with granite counter tops, offers plenty of cabinet space. The adjacent Dining area has sliders to a covered deck. Another Pellet stove in the Living Room gives true Vermont warmth. Primary Bedroom has attached bath with dual sinks, while the other 2 bedrooms share the hallway bath. The additions of the Sun Room and vaulted ceiling Family Room, with wood walls and c

$299,000

3 beds2 baths1,400 sq ft

25 Felton Rd, Weston, VT 05161

Covered deck • Sunroom • Pellet stove

Property at 162 Okemo Trailside Ext Unit 22C-L, Ludlow, VT 05149, 1 bed, 1 bath

$375,000

1 bed1 bath884 sq ft

162 Okemo Trailside Ext Unit 22C-L, Ludlow, VT 05149

Property at 11 Blueberry Ledge Rdg Unit L-3, Plymouth, VT 05056, 3 beds, 3 baths

$445,000

3 beds3 baths1,918 sq ft

11 Blueberry Ledge Rdg Unit L-3, Plymouth, VT 05056

Property at 56 Furnace St, Springfield, VT 05156, 3 beds, 1 bath

$140,000

3 beds1 bath1,368 sq ft

56 Furnace St, Springfield, VT 05156

Property at Jackson Gore Adams House Unit 510/512 QIII, Ludlow, VT 05149, 2 beds, 3 baths

$99,000

2 beds3 baths1,369 sq ft

Jackson Gore Adams House Unit 510/512 QIII, Ludlow, VT 05149

Property at 2359 VT Route 107, Bethel, VT 05032, 2 beds, 2 baths

$235,995

2 beds2 baths1,076 sq ft

2359 VT Route 107, Bethel, VT 05032

Property at 807 Murphys Rd Unit 7D, Hartford, VT 05059, 1 bed, 2 baths

$388,888

1 bed2 baths884 sq ft

807 Murphys Rd Unit 7D, Hartford, VT 05059

Property at Jackson Gore Adams House Unit 606/608 QII, Ludlow, VT 05149, 2 beds, 3 baths

$100,000

2 beds3 baths1,367 sq ft

Jackson Gore Adams House Unit 606/608 QII, Ludlow, VT 05149

Property at 416 Qtr. I Jackson Gore Inn, Ludlow, VT 05149, 1 bed, 2 baths

$69,000

1 bed2 baths775 sq ft

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

Property at 9 Stryhas Trailer Ct, Ludlow, VT 05149, 3 beds, 2 baths

$179,000

3 beds2 baths1,120 sq ft

9 Stryhas Trailer Ct, Ludlow, VT 05149

Property at 1438 Gravelin Rd, Perkinsville, VT 05151, 2 beds, 1 bath

$169,500

2 beds1 bath1,500 sq ft

1438 Gravelin Rd, Perkinsville, VT 05151

Property at 32 Reed St, Springfield, VT 05156

$169,000

— beds— baths1,662 sq ft

32 Reed St, Springfield, VT 05156

Property at 396 S Main St, Bethel, VT 05032, 2 beds, 2 baths

$205,000

2 beds2 baths1,420 sq ft

396 S Main St, Bethel, VT 05032

Property at 807 Murphys RD Unit 7d, Quechee, VT 05059, 1 bed, 2 baths

$388,888

1 bed2 baths884 sq ft

807 Murphys RD Unit 7d, Quechee, VT 05059

Property at 513 Giddings St, North Springfield, VT 05150, 5 beds, 3 baths

$325,000

5 beds3 baths2,963 sq ft

513 Giddings St, North Springfield, VT 05150

Property at 6852 US Route 4, Bridgewater, VT 05034, 3 beds, 2 baths

$449,000

3 beds2 baths1,489 sq ft

6852 US Route 4, Bridgewater, VT 05034

Property at 104 Deer Run #13, Brownsville, VT 05037, 2 beds, 1.5 baths

$240,000

2 beds1.5 baths1,140 sq ft

104 Deer Run #13, Brownsville, VT 05037

Property at 78 Division St, Hartford, VT 05088, 2 beds, 2 baths

$339,000

2 beds2 baths1,451 sq ft

78 Division St, Hartford, VT 05088

Property at 185 Riverbend Way, Woodstock, VT 05091, 3 beds, 2 baths

$72,999

3 beds2 baths1,008 sq ft

185 Riverbend Way, Woodstock, VT 05091

Property at 1226 E Ash Rd Unit L34, Plymouth, VT 05056, 4 beds, 3 baths

$419,000

4 beds3 baths1,920 sq ft

1226 E Ash Rd Unit L34, Plymouth, VT 05056

Property at 37 Atwood Ave, Woodstock, VT 05091, 2 beds, 1 bath

$420,000

2 beds1 bath768 sq ft

37 Atwood Ave, Woodstock, VT 05091

Property at 101 Mount Vernon St, Springfield, VT 05156, 5 beds, 2 baths

$250,000

5 beds2 baths1,728 sq ft

101 Mount Vernon St, Springfield, VT 05156

Property at 842 Main St, Proctorsville, VT 05153, 3 beds, 2 baths

$289,000

3 beds2 baths1,232 sq ft

842 Main St, Proctorsville, VT 05153

Property at 64 Summer Hill St, Springfield, VT 05156, 3 beds, 2 baths

$389,900

3 beds2 baths2,776 sq ft

64 Summer Hill St, Springfield, VT 05156

Property at 9 Walnut St, Hartford, VT 05088, 2 beds, 2 baths

$96,232

2 beds2 baths777 sq ft

9 Walnut St, Hartford, VT 05088

Property at 11 Cubb Ct, Windsor, VT 05089, 2 beds, 2 baths

$96,232

2 beds2 baths777 sq ft

11 Cubb Ct, Windsor, VT 05089

Property at 23 Cubb Ct, Windsor, VT 05089, 1 bed, 1 bath

$87,826

1 bed1 bath643 sq ft

23 Cubb Ct, Windsor, VT 05089

Property at 132 Cubb Ct, Windsor, VT 05089, 2 beds, 2 baths

$96,232

2 beds2 baths777 sq ft

132 Cubb Ct, Windsor, VT 05089

Property at 84 Cubb Ct, Windsor, VT 05089, 3 beds, 2 baths

$98,995

3 beds2 baths880 sq ft

84 Cubb Ct, Windsor, VT 05089

Property at 517 Back Mountain Rd, Windsor, VT 05089, 2 beds, 2 baths

$96,232

2 beds2 baths777 sq ft

517 Back Mountain Rd, Windsor, VT 05089

Property at 7873 Pomfret Rd, North Pomfret, VT 05053, 3 beds, 1.5 baths

$434,500

3 beds1.5 baths1,582 sq ft

7873 Pomfret Rd, North Pomfret, VT 05053

Property at 121 E Lake Rd, Ludlow, VT 05149, 3 beds, 1 bath

$425,000

3 beds1 bath895 sq ft

121 E Lake Rd, Ludlow, VT 05149

Property at 919 Vermont Route 100 S, Rochester, VT 05767, 3 beds, 1 bath

$359,000

3 beds1 bath1,144 sq ft

919 Vermont Route 100 S, Rochester, VT 05767

Property at 365 Q4 Jackson Gore Inn Rd Unit 365 Q4, Ludlow, VT 05149, 1 bath

$49,000

0 beds1 bath390 sq ft

365 Q4 Jackson Gore Inn Rd Unit 365 Q4, Ludlow, VT 05149

Property at 419 Coach Rd, Chester, VT 05143, 3 beds, 1 bath

$239,000

3 beds1 bath1,440 sq ft

419 Coach Rd, Chester, VT 05143

Property at 355 Lyman Bacheller Rd Unit B, Quechee, VT 05059, 2 beds, 1.5 baths

$339,000

2 beds1.5 baths1,356 sq ft

355 Lyman Bacheller Rd Unit B, Quechee, VT 05059

Property at 160 Depot St, Chester, VT 05143, 3 beds, 1 bath

$225,000

3 beds1 bath1,327 sq ft

160 Depot St, Chester, VT 05143

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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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