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. $1,639,000. 19 West Main Street, Chester. 4 Beds, 4 Baths, 3,545 SqFt, Single Family For Sale, MLS® # 24001628.
19 West Main Street, Chester

$1,639,000

Active

19 West Main Street, Chester

4 Beds 4 Baths 3,545 SqFt Single Family For Sale MLS® # 24001628

Coldwell Banker Realty

Listing. $1,499,000. 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

$1,499,000

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. $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

Active

9 Old County Road, Chester

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

William Pitt Sotheby's Int'l

Listing. $795,000. 75 Pinnacle Lane, Chester. 4 Beds, 3 Baths, 3,033 SqFt, Single Family For Sale, MLS® # 24006945.
75 Pinnacle Lane, Chester

$795,000

Under Contract

75 Pinnacle Lane, Chester

4 Beds 3 Baths 3,033 SqFt Single Family For Sale MLS® # 24006945

Century 21 Clemens Group

Listing. $529,900. 25 Deep Hollow Road, Chester. 3 Beds, 3 Baths, 1,710 SqFt, Single Family For Sale, MLS® # 24004230.
25 Deep Hollow Road, Chester

$529,900

↓ $35,100 Active

25 Deep Hollow Road, Chester

3 Beds 3 Baths 1,710 SqFt Single Family For Sale MLS® # 24004230

REMAX Valley Shore

Listing. $499,900. 16 Middlesex Avenue, Chester. 3 Beds, 2 Baths, 1,963 SqFt, Single Family For Sale, MLS® # 170609851.
16 Middlesex Avenue, Chester

$499,900

↓ $15,100 Under Contract

16 Middlesex Avenue, Chester

3 Beds 2 Baths 1,963 SqFt Single Family For Sale MLS® # 170609851

KW Legacy Partners

Listing. $499,000. 26 Water Street, Chester. 1 Beds, 1 Baths, 1,521 SqFt, Single Family For Sale, MLS® # 170617490.
26 Water Street, Chester

$499,000

↓ $25,900 Under Contract

26 Water Street, Chester

1 Bed 1 Bath 1,521 SqFt Single Family For Sale MLS® # 170617490

William Pitt Sotheby's Int'l

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

$450,000

Active

8 Bokum Road, Chester

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

Puorro Realty Group

New Listing. $399,900. 33 Castle View Drive, Chester. 3 Beds, 1 Baths, 1,080 SqFt, Single Family For Sale, MLS® # 24008480.
New
33 Castle View Drive, Chester

$399,900

Active

33 Castle View Drive, Chester

3 Beds 1 Bath 1,080 SqFt Single Family For Sale MLS® # 24008480

REMAX Valley Shore