Recently Sold Homes in Windsor County, VT

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SOLD SEP 30, 2025

ABOUT THIS HOME
Recently Sold Home in Windsor County, VT:
Here's a hidden gem for you in the heart of Vermont's magical, tranquil and picturesque countryside. Situated on 22 acres of forest and field sits a modest ranch home that is simplistic in style but overflowing with warmth and contentment. Loved for 40k+ years, it will be hard to turn over to its next denizen. The home is a time capsule of 70's charm and with some updating, can be enhanced with a new timeless country feel. Bring your creativity to this lovely setting. The property is completed with Hubbard Brook meandering through along with parcels that might be subdivided off should you desire for others to set up their homestead. Showings are delayed until open house on Sunday, June 22nd

$299,000 Last sold price

2 beds1 bath1,332 sq ft

2505 County Rd, Windsor, VT 05089

SOLD AUG 28, 2025

ABOUT THIS HOME
Recently Sold Home in Windsor County, VT:
Welcome to this rejuvenated home with one car garage with recent updates including fresh paint and flooring, new kitchen counter tops and cabinets and light fixtures. There’s good interior space with a living room, dining room, family room, second floor laundry and 3 bedrooms upstairs as well as an enclosed front porch for evening relaxing. This is a great opportunity and should be on your short list!

$292,500 Last sold price

3 beds1.5 baths1,606 sq ft

32 Clough Ave, Windsor, VT 05089

SOLD NOV 13, 2025

ABOUT THIS HOME
Recently Sold Home in Windsor County, VT:
Step into the timeless appeal of this beautifully maintained 1920s home, ideally situated in the heart of Olde Windsor. The inviting front patio welcomes you into a charming entryway that opens to a cozy living room, perfect for relaxing evenings or entertaining guests. Gleaming hardwood floors flow through the entry and dining areas, adding warmth and character throughout. The spacious dining room connects seamlessly to a well-appointed kitchen, offering both functionality and charm. A conveniently located half bath on the main floor includes an integrated washer and dryer for added ease. From the dining area, step out to the back patio and take in serene views of the expansive backyard, i

$271,000 Last sold price

3 beds1.5 baths1,320 sq ft

10 McKenzie Dr, Windsor, VT 05089

SOLD AUG 25, 2025

ABOUT THIS HOME
Recently Sold Home in Windsor County, VT:
Nestled in a peaceful rural setting, this roomy 4-bedroom, 3-bathroom home offers incredible potential for those looking to create their dream country home. While the property is in need of some work, it features a generous layout and sits on a little over an acre, which allows for plenty of space to enjoy the beautiful setting. The home features hardwood floors, vinyl windows, a pellet stove, as well as nicely appointed kitchen and granite countertops. Whether you're an investor or a homeowner with a vision, this fixer upper is a rare opportunity to craft a customized living space in a serene countryside location. Showing requires 24-hour notice due to tenants, property is being sold &quot

$290,000 Last sold price

4 beds2.5 baths2,196 sq ft

1471 County Rd, Windsor, VT 05086

SOLD SEP 2, 2025

ABOUT THIS HOME
Recently Sold Home in Windsor County, VT:
PRICE JUST IMPROVED! Welcome to this beautifully maintained New Englander nestled in the historic town of Windsor — Vermont's first capital and a gem of the Upper Valley. This classic 3-bedroom, 2-bath home blends timeless charm with thoughtful updates, offering a perfect retreat in a vibrant, small-town setting. Located within walking distance to Windsor’s shops, restaurants, schools, and the picturesque Connecticut River — and just minutes from I-91 — this home combines small-town charm with accessibility.

$219,000 Last sold price

3 beds2 baths1,743 sq ft

66 Union St, Windsor, VT 05089

Property at 9 Main St, Windsor, VT 05089, 4 beds, 1.5 baths

$200,001 Last sold price

4 beds1.5 baths2,310 sq ft

9 Main St, Windsor, VT 05089

Property at 58 Morningside Dr, Windsor, VT 05089, 3 beds, 1.5 baths

$395,900 Last sold price

3 beds1.5 baths1,680 sq ft

58 Morningside Dr, Windsor, VT 05089

Property at 968 Ski Tow Rd, West Windsor, VT 05037, 4 beds, 2.5 baths

$515,000 Last sold price

4 beds2.5 baths2,380 sq ft

968 Ski Tow Rd, West Windsor, VT 05037

Property at 65 Bergland Ln, West Windsor, VT 05037, 3 beds, 2 baths

$535,000 Last sold price

3 beds2 baths1,608 sq ft

65 Bergland Ln, West Windsor, VT 05037

Property at 204 High Ridge Rd, Brownsville, VT 05037, 4 beds, 3 baths

$1,000,000 Last sold price

4 beds3 baths3,796 sq ft

204 High Ridge Rd, Brownsville, VT 05037

Property at 586 Ski Tow Rd, Brownsville, VT 05037, 3 beds, 2 baths

$460,000 Last sold price

3 beds2 baths1,480 sq ft

586 Ski Tow Rd, Brownsville, VT 05037

Property at 929 Bible Hill Rd, Brownsville, VT 05037, 3 beds, 2 baths

$720,000 Last sold price

3 beds2 baths2,727 sq ft

929 Bible Hill Rd, Brownsville, VT 05037

Property at 2077 Sheddsville Rd, West Windsor, VT 05089, 3 beds, 3.5 baths

$1,150,000 Last sold price

3 beds3.5 baths2,424 sq ft

2077 Sheddsville Rd, West Windsor, VT 05089

Property at 1159 Ski Tow Rd, West Windsor, VT 05037, 3 beds, 2 baths

$315,000 Last sold price

3 beds2 baths1,656 sq ft

1159 Ski Tow Rd, West Windsor, VT 05037

Property at 578 E Barnard Rd, South Royalton, VT 05031, 1 bed, 2 baths

$572,000 Last sold price

1 bed2 baths1,384 sq ft

578 E Barnard Rd, South Royalton, VT 05031

Property at 1082 Greengate Rd, Woodstock, VT 05091, 3 beds, 2.5 baths

$740,000 Last sold price

3 beds2.5 baths1,878 sq ft

1082 Greengate Rd, Woodstock, VT 05091

Property at 411 Bennett Rd, Barnard, VT 05031, 4 beds, 3.5 baths

$1,450,000 Last sold price

4 beds3.5 baths3,018 sq ft

411 Bennett Rd, Barnard, VT 05031

Property at 2615 North Rd, Bethel, VT 05032, 5 beds, 4.5 baths

$399,900 Last sold price

5 beds4.5 baths6,236 sq ft

2615 North Rd, Bethel, VT 05032

Property at 6196 Stage Rd, Barnard, VT 05031, 4 beds, 3 baths

$1,520,000 Last sold price

4 beds3 baths2,408 sq ft

6196 Stage Rd, Barnard, VT 05031

Property at 687 S Perry Rd, Woodstock, VT 05091, 5 beds, 4.5 baths

$1,300,000 Last sold price

5 beds4.5 baths4,617 sq ft

687 S Perry Rd, Woodstock, VT 05091

Property at 42 Harrison Ln Unit M204, Ludlow, VT 05149, 3 beds, 2 baths

$613,000 Last sold price

3 beds2 baths1,296 sq ft

42 Harrison Ln Unit M204, Ludlow, VT 05149

Property at 74 Grouse Ln, Ludlow, VT 05149, 5 beds, 3.5 baths

$2,750,000 Last sold price

5 beds3.5 baths4,360 sq ft

74 Grouse Ln, Ludlow, VT 05149

Property at 7 Maple Ln, Ludlow, VT 05149, 2 beds, 1.5 baths

$249,000 Last sold price

2 beds1.5 baths960 sq ft

7 Maple Ln, Ludlow, VT 05149

Property at 80 Mountain View Dr, Ludlow, VT 05149, 5 beds, 3.5 baths

$1,090,000 Last sold price

5 beds3.5 baths3,775 sq ft

80 Mountain View Dr, Ludlow, VT 05149

Property at 26 Country Xing, Ludlow, VT 05149, 3 beds, 3 baths

$680,000 Last sold price

3 beds3 baths3,432 sq ft

26 Country Xing, Ludlow, VT 05149

Property at 109 Okemo Ridge Rd Unit C-301, Ludlow, VT 05149, 1 bed, 1 bath

$391,800 Last sold price

1 bed1 bath638 sq ft

109 Okemo Ridge Rd Unit C-301, Ludlow, VT 05149

Property at 360 Okemo Trailside Ext Unit 37C, Ludlow, VT 05149, 3 beds, 2.5 baths

$847,500 Last sold price

3 beds2.5 baths1,694 sq ft

360 Okemo Trailside Ext Unit 37C, Ludlow, VT 05149

Property at 161 Fishing Access Rd, Ludlow, VT 05149, 3 beds, 3.5 baths

$1,750,000 Last sold price

3 beds3.5 baths2,550 sq ft

161 Fishing Access Rd, Ludlow, VT 05149

Property at 37 Wright Rd, Ludlow, VT 05149, 3 beds, 2.5 baths

$250,000 Last sold price

3 beds2.5 baths2,072 sq ft

37 Wright Rd, Ludlow, VT 05149

Property at 17 Bixby Rd, Ludlow, VT 05149, 3 beds, 2 baths

$432,450 Last sold price

3 beds2 baths2,432 sq ft

17 Bixby Rd, Ludlow, VT 05149

Property at 102 Brooks Rd, Ludlow, VT 05149, 3 beds, 2 baths

$340,000 Last sold price

3 beds2 baths2,580 sq ft

102 Brooks Rd, Ludlow, VT 05149

Property at 30 Pond St #8, Ludlow, VT 05149, 2 beds, 2 baths

$212,000 Last sold price

2 beds2 baths780 sq ft

30 Pond St #8, Ludlow, VT 05149

Property at 721 N Hill Cross Rd, Ludlow, VT 05149, 2 beds, 1 bath

$225,000 Last sold price

2 beds1 bath979 sq ft

721 N Hill Cross Rd, Ludlow, VT 05149

Property at 57 Route 100 S, Ludlow, VT 05149, 4 beds, 2.5 baths

$499,000 Last sold price

4 beds2.5 baths2,570 sq ft

57 Route 100 S, Ludlow, VT 05149

Property at 19 Bear Ridge Rd, Ludlow, VT 05149, 3 beds, 2.5 baths

$650,000 Last sold price

3 beds2.5 baths1,966 sq ft

19 Bear Ridge Rd, Ludlow, VT 05149

Property at 54 Andover St, Ludlow, VT 05149, 4 beds, 3 baths

$425,000 Last sold price

4 beds3 baths3,004 sq ft

54 Andover St, Ludlow, VT 05149

Property at 2 Macdonald Ln, Ludlow, VT 05149, 3 beds, 3 baths

$715,000 Last sold price

3 beds3 baths2,630 sq ft

2 Macdonald Ln, Ludlow, VT 05149

Property at 22 Andover St, Ludlow, VT 05149, 3 beds, 1.5 baths

$260,000 Last sold price

3 beds1.5 baths1,546 sq ft

22 Andover St, Ludlow, VT 05149

Property at 30 Pond St #11, Ludlow, VT 05149, 2 beds, 2 baths

$260,000 Last sold price

2 beds2 baths806 sq ft

30 Pond St #11, Ludlow, VT 05149

Property at 32 Route 103 S Unit B8, Ludlow, VT 05149, 3 beds, 2 baths

$365,000 Last sold price

3 beds2 baths1,116 sq ft

32 Route 103 S Unit B8, Ludlow, VT 05149

Property at 8 Meadow St, Ludlow, VT 05149, 2 beds, 1 bath

$352,000 Last sold price

2 beds1 bath1,663 sq ft

8 Meadow St, Ludlow, VT 05149

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Recently Sold Homes in Windsor County

There are currently 451 recently sold 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 104 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 21 2025 on the search page

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