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® # 24001628.
19 West Main Street, Chester

$1,499,000

↓ $140,000 Active

19 West Main Street, Chester

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

Coldwell Banker Realty

New Listing. $1,050,000. 248 Middlesex Avenue, Chester. 4 Beds, 4 Baths, 4,862 SqFt, Single Family For Sale, MLS® # 24016366.
New
248 Middlesex Avenue, Chester

$1,050,000

Active

248 Middlesex Avenue, Chester

4 Beds 4 Baths 4,862 SqFt Single Family For Sale MLS® # 24016366

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

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 Under Contract

25 Deep Hollow Road, Chester

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

REMAX Valley Shore

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

Active

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

Active

8 Bokum Road, Chester

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

Puorro Realty Group

New Listing. $379,900. 42 West Main Street, Chester. 4 Beds, 2 Baths, 1,766 SqFt, Single Family For Sale, MLS® # 24015650.
New
42 West Main Street, Chester

$379,900

Under Contract

42 West Main Street, Chester

4 Beds 2 Baths 1,766 SqFt Single Family For Sale MLS® # 24015650

William Pitt Sotheby's Int'l

Listing. $375,000. 33 Castle View Drive, Chester. 3 Beds, 1 Baths, 1,080 SqFt, Single Family For Sale, MLS® # 24008480.
33 Castle View Drive, Chester

$375,000

↓ $24,900 Under Contract

33 Castle View Drive, Chester

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

REMAX Valley Shore