Chester Homes For Sale

Chester is part of what the locals call the “Tri-Town Area” made up of Deep River, Essex, and Chester. With a population of about 3,800 and consisting of 16.8 square miles, Chester is located on the Western Bank of the Connecticut River in Middlesex County. Downtown Chester is picturesque and offers 19th-century charm with a melody of shops, eateries and a creative spirit that is captured by the artists, artisans and neighbors alike. The town of Chester also has lakes, ponds, cascading waterfalls, a state forest, marinas, and even a small airport. 

Property Results

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Listing. $1,499,000. 19 West Main Street, Chester. 4 Beds, 4 Baths, 3,545 SqFt, Single Family For Sale, MLS® # 24044453.
19 West Main Street, Chester

$1,499,000

Active

19 West Main Street, Chester

4 Beds 4 Baths 3,545 SqFt Single Family For Sale MLS® # 24044453

Coldwell Banker Realty

Listing. $1,395,000. 96 Middlesex Avenue, Chester. 4 Beds, 4 Baths, 3,153 SqFt, Single Family For Sale, MLS® # 24038493.
96 Middlesex Avenue, Chester

$1,395,000

Active

96 Middlesex Avenue, Chester

4 Beds 4 Baths 3,153 SqFt Single Family For Sale MLS® # 24038493

William Pitt Sotheby's Int'l

New Listing. $1,325,000. 35-16 Castle View Drive, Chester. 3 Beds, 3 Baths, 2,006 SqFt, Single Family For Sale, MLS® # 24038447.
New
35-16 Castle View Drive, Chester

$1,325,000

Under Contract

35-16 Castle View Drive, Chester

3 Beds 3 Baths 2,006 SqFt Single Family For Sale MLS® # 24038447

Silver and Oak Realty

Listing. $1,280,000. 16 Waterhouse Lane, Chester. 4 Beds, 5 Baths, 4,661 SqFt, Single Family For Sale, MLS® # 24019380.
16 Waterhouse Lane, Chester

$1,280,000

↓ $115,000 Active

16 Waterhouse Lane, Chester

4 Beds 5 Baths 4,661 SqFt Single Family For Sale MLS® # 24019380

Compass Connecticut, LLC

Listing. $789,000. 28 South Wig Hill Road, Chester. 2 Beds, 3 Baths, 3,091 SqFt, Single Family For Sale, MLS® # 24035876.
28 South Wig Hill Road, Chester

$789,000

Active

28 South Wig Hill Road, Chester

2 Beds 3 Baths 3,091 SqFt Single Family For Sale MLS® # 24035876

Seaport Real Estate Services

Listing. $779,000. 68 West Main Street, Chester. 6 Beds, 2 Baths, 3,518 SqFt, Single Family For Sale, MLS® # 24024772.
68 West Main Street, Chester

$779,000

↓ $71,000 Under Contract

68 West Main Street, Chester

6 Beds 2 Baths 3,518 SqFt Single Family For Sale MLS® # 24024772

William Pitt Sotheby's Int'l

Listing. $775,000. 108 Middlesex Avenue, Chester. 3 Beds, 5 Baths, 4,056 SqFt, Single Family For Sale, MLS® # 24040512.
108 Middlesex Avenue, Chester

$775,000

Active

108 Middlesex Avenue, Chester

3 Beds 5 Baths 4,056 SqFt Single Family For Sale MLS® # 24040512

Chiarito Real Estate LLC

Listing. $599,000. 142 Main Street, Chester. 3 Beds, 2 Baths, 2,188 SqFt, Single Family For Sale, MLS® # 24034521.
142 Main Street, Chester

$599,000

↓ $40,900 Active

142 Main Street, Chester

3 Beds 2 Baths 2,188 SqFt Single Family For Sale MLS® # 24034521

Berkshire Hathaway NE Prop.

Listing. $599,000. 71 Maple Street, Chester. 2 Beds, 2 Baths, 2,144 SqFt, Single Family For Sale, MLS® # 24037135.
71 Maple Street, Chester

$599,000

Active

71 Maple Street, Chester

2 Beds 2 Baths 2,144 SqFt Single Family For Sale MLS® # 24037135

Berkshire Hathaway NE Prop.