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. $3,495,000. 31 Parkers Point Road, Chester. 3 Beds, 4 Baths, 4,727 SqFt, Single Family For Sale, MLS® # 24082394.
31 Parkers Point Road, Chester

$3,495,000

Under Contract

31 Parkers Point Road, Chester

3 Beds 4 Baths 4,727 SqFt Single Family For Sale MLS® # 24082394

William Pitt Sotheby's Int'l

Listing. $1,299,000. 7 Old Depot Road, Chester. 4 Beds, 3 Baths, 3,149 SqFt, Single Family For Sale, MLS® # 24069434.
7 Old Depot Road, Chester

$1,299,000

Active

7 Old Depot Road, Chester

4 Beds 3 Baths 3,149 SqFt Single Family For Sale MLS® # 24069434

William Pitt Sotheby's Int'l

Listing. $1,150,000. 32 Gilbert Hill Road, Chester. 3 Beds, 3 Baths, 3,788 SqFt, Single Family For Sale, MLS® # 24091259.
32 Gilbert Hill Road, Chester

$1,150,000

Active

32 Gilbert Hill Road, Chester

3 Beds 3 Baths 3,788 SqFt Single Family For Sale MLS® # 24091259

Exclusive Properties

Listing. $1,100,000. 25 Gilbert Hill Road, Chester. 4 Beds, 5 Baths, 3,351 SqFt, Single Family For Sale, MLS® # 24059139.
25 Gilbert Hill Road, Chester

$1,100,000

Under Contract

25 Gilbert Hill Road, Chester

4 Beds 5 Baths 3,351 SqFt Single Family For Sale MLS® # 24059139

William Pitt Sotheby's Int'l

Listing. $985,000. 88 Winthrop Road, Chester. 2 Beds, 3 Baths, 2,240 SqFt, Single Family For Sale, MLS® # 24081139.
88 Winthrop Road, Chester

$985,000

Active

88 Winthrop Road, Chester

2 Beds 3 Baths 2,240 SqFt Single Family For Sale MLS® # 24081139

REMAX Valley Shore

Listing. $895,000. 79 Cedar Lake Road, Chester. 4 Beds, 3 Baths, 3,206 SqFt, Single Family For Sale, MLS® # 24090570.
79 Cedar Lake Road, Chester

$895,000

Active

79 Cedar Lake Road, Chester

4 Beds 3 Baths 3,206 SqFt Single Family For Sale MLS® # 24090570

William Raveis Real Estate

Listing. $895,000. 25 Spring Street, Chester. 3 Beds, 3 Baths, 2,164 SqFt, Single Family For Sale, MLS® # 24090759.
25 Spring Street, Chester

$895,000

Under Contract

25 Spring Street, Chester

3 Beds 3 Baths 2,164 SqFt Single Family For Sale MLS® # 24090759

William Pitt Sotheby's Int'l

New Listing. $819,000. 15 Gilbert Hill Road, Chester. 4 Beds, 3 Baths, 3,054 SqFt, Single Family For Sale, MLS® # 24077655.
New
15 Gilbert Hill Road, Chester

$819,000

Under Contract

15 Gilbert Hill Road, Chester

4 Beds 3 Baths 3,054 SqFt Single Family For Sale MLS® # 24077655

Berkshire Hathaway NE Prop.

Listing. $784,900. 43 North Main Street, Chester. 3 Beds, 2 Baths, 1,538 SqFt, Single Family For Sale, MLS® # 24091213.
43 North Main Street, Chester

$784,900

Active

43 North Main Street, Chester

3 Beds 2 Baths 1,538 SqFt Single Family For Sale MLS® # 24091213

William Pitt Sotheby's Int'l