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. $1,595,000. 19 West Main Street, Chester. 4 Beds, 4 Baths, 3,545 SqFt, Single Family For Sale, MLS® # 24028627.
19 West Main Street, Chester

$1,595,000

Active

19 West Main Street, Chester

4 Beds 4 Baths 3,545 SqFt Single Family For Sale MLS® # 24028627

Coldwell Banker Realty

Listing. $1,449,900. 35-16 Castle View Drive, Chester. 3 Beds, 3 Baths, 2,006 SqFt, Single Family For Sale, MLS® # 170623499.
35-16 Castle View Drive, Chester

$1,449,900

↓ $100,000 Active

35-16 Castle View Drive, Chester

3 Beds 3 Baths 2,006 SqFt Single Family For Sale MLS® # 170623499

Silver and Oak Realty

Listing. $1,395,000. 16 Waterhouse Lane, Chester. 4 Beds, 5 Baths, 4,661 SqFt, Single Family For Sale, MLS® # 24019380.
16 Waterhouse Lane, Chester

$1,395,000

Active

16 Waterhouse Lane, Chester

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

Compass Connecticut, LLC

Listing. $850,000. 68 West Main Street, Chester. 6 Beds, 2 Baths, 3,518 SqFt, Single Family For Sale, MLS® # 24024772.
68 West Main Street, Chester

$850,000

Active

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. $849,000. 9 Old County Road, Chester. 4 Beds, 4 Baths, 4,361 SqFt, Single Family For Sale, MLS® # 24006823.
9 Old County Road, Chester

$849,000

Under Contract

9 Old County Road, Chester

4 Beds 4 Baths 4,361 SqFt Single Family For Sale MLS® # 24006823

William Pitt Sotheby's Int'l

New Listing. $670,000. 142 Main Street, Chester. 3 Beds, 2 Baths, 2,188 SqFt, Single Family For Sale, MLS® # 24034521.
New
142 Main Street, Chester

$670,000

Active

142 Main Street, Chester

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

Berkshire Hathaway NE Prop.

New Listing. $625,000. 25 Spring Street, Chester. 3 Beds, 3 Baths, 2,164 SqFt, Single Family For Sale, MLS® # 24027651.
New
25 Spring Street, Chester

$625,000

Under Contract

25 Spring Street, Chester

3 Beds 3 Baths 2,164 SqFt Single Family For Sale MLS® # 24027651

Berkshire Hathaway NE Prop.

New Listing. $500,000. 40 Gilbert Hill Road, Chester. 2 Beds, 3 Baths, 1,395 SqFt, Single Family For Sale, MLS® # 24019218.
New
40 Gilbert Hill Road, Chester

$500,000

Under Contract

40 Gilbert Hill Road, Chester

2 Beds 3 Baths 1,395 SqFt Single Family For Sale MLS® # 24019218

Coldwell Banker Realty

Listing. $450,000. 8 Bokum Road, Chester. 3 Beds, 2 Baths, 1,738 SqFt, Single Family For Sale, MLS® # 24013212.
8 Bokum Road, Chester

$450,000

Under Contract

8 Bokum Road, Chester

3 Beds 2 Baths 1,738 SqFt Single Family For Sale MLS® # 24013212

Puorro Realty Group