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, 4,205 SqFt, Single Family For Sale, MLS® # 24054425.
19 West Main Street, Chester

$1,499,000

Active

19 West Main Street, Chester

4 Beds 4 Baths 4,205 SqFt Single Family For Sale MLS® # 24054425

Compass Connecticut, LLC

Listing. $1,375,000. 96 Middlesex Avenue, Chester. 4 Beds, 4 Baths, 3,153 SqFt, Single Family For Sale, MLS® # 24038493.
96 Middlesex Avenue, Chester

$1,375,000

Under Contract

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

New Listing. $869,000. 6 Old County Road, Chester. 4 Beds, 3 Baths, 2,680 SqFt, Single Family For Sale, MLS® # 24068350.
New
6 Old County Road, Chester

$869,000

Active

6 Old County Road, Chester

4 Beds 3 Baths 2,680 SqFt Single Family For Sale MLS® # 24068350

William Pitt Sotheby's Int'l

Listing. $764,000. 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

$764,000

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. $635,000. 67 West Main Street, Chester. 3 Beds, 2 Baths, 1,916 SqFt, Single Family For Sale, MLS® # 24059398.
67 West Main Street, Chester

$635,000

Under Contract

67 West Main Street, Chester

3 Beds 2 Baths 1,916 SqFt Single Family For Sale MLS® # 24059398

Coldwell Banker Realty

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.

Listing. $545,000. 5 Marina View Drive, Chester. 3 Beds, 4 Baths, 2,037 SqFt, Single Family For Sale, MLS® # 24050368.
5 Marina View Drive, Chester

$545,000

Under Contract

5 Marina View Drive, Chester

3 Beds 4 Baths 2,037 SqFt Single Family For Sale MLS® # 24050368

William Pitt Sotheby's Int'l

Listing. $446,000. 2 Sypher Road, Chester. 4 Beds, 3 Baths, 2,278 SqFt, Single Family For Sale, MLS® # 24056839.
2 Sypher Road, Chester

$446,000

Under Contract

2 Sypher Road, Chester

4 Beds 3 Baths 2,278 SqFt Single Family For Sale MLS® # 24056839

William Pitt Sotheby's Int'l