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

Click the links below to sort results by price range.

Sort by:
Listing. $1,600,000. 43 Liberty Street, Chester. 3 Beds, 3 Baths, 1,901 SqFt, Single Family For Sale, MLS® # 170607764.
43 Liberty Street, Chester

$1,600,000

Active

43 Liberty Street, Chester

3 Beds 3 Baths 1,901 SqFt Single Family For Sale MLS® # 170607764

William Pitt Sotheby's Int'l

Listing. $1,195,000. 248 Middlesex Avenue, Chester. 4 Beds, 4 Baths, 4,862 SqFt, Single Family For Sale, MLS® # 170606345.
248 Middlesex Avenue, Chester

$1,195,000

Active

248 Middlesex Avenue, Chester

4 Beds 4 Baths 4,862 SqFt Single Family For Sale MLS® # 170606345

William Pitt Sotheby's Int'l

Listing. $799,000. 22 Waterhouse Lane, Chester. 3 Beds, 3 Baths, 3,802 SqFt, Single Family For Sale, MLS® # 170610713.
22 Waterhouse Lane, Chester

$799,000

Active

22 Waterhouse Lane, Chester

3 Beds 3 Baths 3,802 SqFt Single Family For Sale MLS® # 170610713

REMAX Valley Shore

Listing. $724,000. 17 Kings Highway, Chester. 4 Beds, 3 Baths, 2,428 SqFt, Single Family For Sale, MLS® # 170607480.
17 Kings Highway, Chester

$724,000

Active

17 Kings Highway, Chester

4 Beds 3 Baths 2,428 SqFt Single Family For Sale MLS® # 170607480

William Raveis Real Estate

Listing. $575,000. 33 Liberty Street, Chester. 3 Beds, 1 Baths, 21,433 SqFt, Single Family For Sale, MLS® # 170595573.
33 Liberty Street, Chester

$575,000

Under Contract

33 Liberty Street, Chester

3 Beds 1 Bath 21,433 SqFt Single Family For Sale MLS® # 170595573

Castleton Realty Associates

Listing. $550,000. 7 Johnson Road, Chester. 3 Beds, 2 Baths, 2,584 SqFt, Single Family For Sale, MLS® # 170596812.
7 Johnson Road, Chester

$550,000

↓ $49,900 Under Contract

7 Johnson Road, Chester

3 Beds 2 Baths 2,584 SqFt Single Family For Sale MLS® # 170596812

William Pitt Sotheby's Int'l

Listing. $435,000. 6 Hickory Hill Drive, Chester. 3 Beds, 2 Baths, 1,821 SqFt, Single Family For Sale, MLS® # 170608414.
6 Hickory Hill Drive, Chester

$435,000

Under Contract

6 Hickory Hill Drive, Chester

3 Beds 2 Baths 1,821 SqFt Single Family For Sale MLS® # 170608414

Clermont Real Estate

Listing. $399,906. 165 West Main Street, Chester. 2 Beds, 1 Baths, 2,400 SqFt, Single Family For Sale, MLS® # 170589475.
165 West Main Street, Chester

$399,906

↓ $30,000 Active

165 West Main Street, Chester

2 Beds 1 Bath 2,400 SqFt Single Family For Sale MLS® # 170589475

Innovative Properties

Listing. $299,900. 21 Castle View Drive, Chester. 3 Beds, 1 Baths, 1,274 SqFt, Single Family For Sale, MLS® # 170607617.
21 Castle View Drive, Chester

$299,900

Under Contract

21 Castle View Drive, Chester

3 Beds 1 Bath 1,274 SqFt Single Family For Sale MLS® # 170607617

William Pitt Sotheby's Int'l