Windham County Real Estate

6,759Results

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Windham County is located in Southern Vermont and borders Massachusetts. It is home to some of the finest skiing in New England at Stratton Mountain. Windham County is also home to very well respected institutions such as Marlboro College and the Central Vermont Medical Center. The largest city and towns in Windham County are Brattleboro and Rockingham, which includes Bellows Falls and Saxtons River. Browse available Windham County real estate below.

Newest

New Listing

$425,000

Dover, VT

231B Route 100, Unit 23B

3 Beds
2 Baths
1,156 SqFt
1 Day on Market

Listed by Ellery Dopkins of Winhall Real Estate

MLS#: 5094849

New Listing

$559,000

Jamaica, VT

155 Pratt Bridge Road

4 Beds
3 Baths
2.5 Acres
2,000 SqFt
1 Day on Market

Listed by Terry Hill of Berkshire Hathaway HomeServices Stratton Home

MLS#: 5094845

New Listing

$499,000

Dover, VT

16A Snowtree Lane

3 Beds
3 Baths
1,707 SqFt
1 Day on Market

Listed by Sheila Joyce-Albano of Skihome Realty

MLS#: 5094774

New Listing

$380,000

Brattleboro, VT

15 Lawton Drive

3 Beds
2 Baths
0.36 Acres
1,056 SqFt
1 Day on Market

Listed by Christine Lewis of Brattleboro Area Realty

MLS#: 5094740

New Listing

$78,000

Brattleboro, VT

4 Reservoir Road

Listed by Victoria Woods of Brattleboro Area Realty

MLS#: 5094697

New Listing

$299,000

Brattleboro, VT

412 Western Avenue

3 Beds
3 Baths
0.22 Acres
1,872 SqFt
2 Days on Market

Listed by Keith Nowak of Four Seasons Sotheby's Int'l Realty

MLS#: 5094671

Open House

$449,000

Jamaica, VT

163 Howe Farm Road

NEXT OPEN HOUSE:

Sat 6/20 9:00 AM to 12:00 PM

3 Beds
3 Baths
2.7 Acres
1,980 SqFt
2 Days on Market

Listed by Julie Lowe of Lowe's Real Estate,LLC

MLS#: 5094647

New Listing

$545,000

Brattleboro, VT

211 Pleasant Valley Road

2 Beds
1 Bath
5.9 Acres
1,576 SqFt
2 Days on Market

Listed by Chris Long of BHG Masiello Brattleboro

MLS#: 5094642

New Listing

$425,000

Londonderry, VT

135 Overlook Drive

3 Baths
2.68 Acres
1,440 SqFt
3 Days on Market

Listed by Zachary Zupan of EXP Realty

MLS#: 5094565

New Listing

$2,500

Jamaica, VT

Clayton Lane

Land
0.18 Acres
3 Days on Market

Listed by Carrie Mathews of Winhall Real Estate

MLS#: 5094564

New Listing

$45,000

Jamaica, VT

West Hill Road

Land
1 Acre
3 Days on Market

Listed by Carrie Mathews of Winhall Real Estate

MLS#: 5094563

New Listing

$45,000

Jamaica, VT

Edie Lane

Land
1 Acre
4 Days on Market

Listed by Carrie Mathews of Winhall Real Estate

MLS#: 5094562

Windham 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 15, 2026 10:23 PM EDT