Windsor County Real Estate

9,202Results

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Windsor County is located along Vermont's eastern border with New Hampshire. It like many of its fellow counties has so much for avid outdoor enthusiasts. From skiing at Okemo Mountain and Suicide Six to flyfishing on the Connecticut River or golfing at the Quechee Club, there is something to do every season in Windsor County. Windsor County also contains many quintessential New England village squares. For instance, the Village of Woodstock features a retail block, a town square, and the historic Woodstock Inn. Not to be outdone though, the County also has other villages, such as Weston which has its own village square and features the famous Vermont Country Store. The largest towns in Windsor County are Hartford, Springfield, and Woodstock. Browse available Windsor County real estate below.

Newest

New Listing

$349,000

Hartford, VT

826 Hard Road, Unit B4

2 Beds
3 Baths
1,648 SqFt
0 Days on Market

Listed by Lisa Baldwin of Coldwell Banker LIFESTYLES - Hanover

MLS#: 5093632

New Listing

$249,000

Hartford, VT

292 Woodhaven Drive, Unit 9F

2 Beds
2 Baths
1,192 SqFt
0 Days on Market

Listed by Gerry Stark of RE/MAX Upper Valley

MLS#: 5093576

New Listing

$1,490,950

Hartford, VT

289 Taft Family Road, Unit 7118

5 Beds
4 Baths
1.01 Acre
2,709 SqFt
0 Days on Market

Listed by Richard Higgerson of Higgerson & Company

MLS#: 5093560

New Listing

$439,000

Bridgewater, VT

538 Bridgewater Center Road

4 Beds
3 Baths
0.93 Acres
2,066 SqFt
0 Days on Market

Listed by Mandolyn McIntyre Crow of Real Broker LLC

MLS#: 5093548

New Listing

$525,000

Ludlow, VT

18 Pleasant Street, Unit 3

4 Beds
3 Baths
2,407 SqFt
1 Day on Market

Listed by Joseph Karl of William Raveis Real Estate Vermont Properties

MLS#: 5093436

New Listing

$329,000

Hartford, VT

136 Horseshoe Avenue

3 Beds
2 Baths
0.18 Acres
2,338 SqFt
1 Day on Market

Listed by Chuck Clifford of Four Seasons Sotheby's Int'l Realty

MLS#: 5093382

New Listing

$75,000

Chester, VT

1144 Potash Brook Road

2 Beds
1 Bath
0.6 Acres
620 SqFt
2 Days on Market

Listed by Julie Buffum of Buffum Realty

MLS#: 5093286

New Listing

$349,900

Springfield, VT

295 Spencer Hollow Road

4 Beds
2 Baths
1.8 Acre
1,546 SqFt
2 Days on Market

Listed by Julie Buffum of Buffum Realty

MLS#: 5093267

New Listing

$109,000

Springfield, VT

17 Clement Road

3 Beds
2 Baths
0.17 Acres
1,185 SqFt
3 Days on Market

Listed by Patrick Kelley of Real Broker LLC

MLS#: 5093193

New Listing

$399,000

Woodstock, VT

1190 Long Hill Road

Land
11.58 Acres
3 Days on Market

Listed by Tara Reeves of Vermont Real Estate Company

MLS#: 5093182

New Listing

$399,000

Woodstock, VT

1190 Long Hill Road

Listed by Tara Reeves of Vermont Real Estate Company

MLS#: 5093181

New Listing

$895,000

Hartford, VT

193 Chester Arthur Road

5 Beds
4 Baths
2.7 Acres
3,631 SqFt
4 Days on Market

Listed by Derek Cosentino of Four Seasons Sotheby's Int'l Realty

MLS#: 5093068

Windsor County VT Homes for Sale

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Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated June 9, 2026 2:09 PM EDT