Middlesex Connecticut Homes for Sale

817 total properties
View 288 Middlesex Avenue Chester, CT MLS# 24166793
  • Virtual Tour
1 of 38
$3,150,000
4

Beds

4.2

Baths

4,926

Sq.Ft.

288 Middlesex Avenue

Chester, CT

View 2 Captains Lane Old Saybrook, CT MLS# 24182941
  • Recently Listed with Virtual Tour
1 of 40
$2,899,900
5

Beds

4.1

Baths

5,062

Sq.Ft.

2 Captains Lane

Old Saybrook, CT

View 99 Shore Road Clinton, CT MLS# 24177108
  • Virtual Tour
1 of 31
$2,850,000
3

Beds

3.1

Baths

2,900

Sq.Ft.

99 Shore Road

Clinton, CT

The time to sell is now! THE TIME TO SELL IS NOW!
View 153 Wallingford Road Durham, CT MLS# 24045388
  • Virtual Tour
1 of 13
$2,800,000
15

Beds

7.1

Baths

10,623

Sq.Ft.

153 Wallingford Road

Durham, CT

View 167 Shore Road Clinton, CT MLS# 24161457
  • Virtual Tour
1 of 40
$2,749,000
4

Beds

4.0

Baths

4,381

Sq.Ft.

167 Shore Road

Clinton, CT

View 47 Old Mail Trail Westbrook, CT MLS# 24169018
  • Virtual Tour
1 of 16
$2,700,000
3

Beds

2.0

Baths

1,800

Sq.Ft.

47 Old Mail Trail

Westbrook, CT

View 88 Main Street Essex, CT MLS# 24162042
  • Virtual Tour
1 of 84
$2,600,000
5

Beds

5.1

Baths

5,234

Sq.Ft.

88 Main Street

Essex, CT

View 5-A Loop Road 5A Clinton, CT MLS# 24175386
$2,600,000
3

Beds

3.0

Baths

2,436

Sq.Ft.

5-A Loop Road 5A

Clinton, CT

View 198-200 West Street Cromwell, CT MLS# 24170060
$2,500,000
3.0

Baths

4,378

Sq.Ft.

198-200 West Street

Cromwell, CT

View 192 Westbrook Road Essex, CT MLS# 24056735
$2,450,000
4.4

Baths

15,316

Sq.Ft.

192 Westbrook Road

Essex, CT

View 250-252 East Main Street Clinton, CT MLS# 24114067
$2,400,000
12,050

Sq.Ft.

250-252 East Main Street

Clinton, CT

View 18 Birch Mill Road Killingworth, CT MLS# 24183296
  • Recently Listed
1 of 65
$2,350,000
3

Beds

2.1

Baths

3,700

Sq.Ft.

18 Birch Mill Road

Killingworth, CT

View 668 Main Street Middletown, CT MLS# 24165225
$2,249,500
21.0

Baths

11,232

Sq.Ft.

668 Main Street

Middletown, CT

View 49 Hammock Road Clinton, CT MLS# 24181231
$2,200,000
4

Beds

2.1

Baths

2,197

Sq.Ft.

49 Hammock Road

Clinton, CT

View 108 Maple Avenue Old Saybrook, CT MLS# 24185410
  • Recently Listed with Virtual Tour
1 of 39
OPEN HOUSE: Sunday 7/5 10:30 AM - 12:00 PM
$2,200,000
4

Beds

2.2

Baths

3,188

Sq.Ft.

108 Maple Avenue

Old Saybrook, CT

View 47 East Kings Highway Chester, CT MLS# 24180698
  • Recently Listed
1 of 40
$2,200,000
4

Beds

3.1

Baths

3,957

Sq.Ft.

47 East Kings Highway

Chester, CT

View 134 Meadow Woods Road Deep River, CT MLS# 24185650
$2,200,000
Studio

Beds

0.0

Baths

134 Meadow Woods Road

Deep River, CT

View 134 Meadow Woods Road Deep River, CT MLS# 24185654
$2,200,000
3

Beds

2.0

Baths

1,591

Sq.Ft.

134 Meadow Woods Road

Deep River, CT

View Lot 2 - 160 Saybrook Road Essex, CT MLS# 24185405
  • Recently Listed
1 of 31
$2,200,000
5

Beds

4.1

Baths

4,750

Sq.Ft.

Lot 2 - 160 Saybrook Road

Essex, CT

View 125 Main Street Old Saybrook, CT MLS# 24138056
$2,195,000
1

Beds

1.1

Baths

7,985

Sq.Ft.

125 Main Street

Old Saybrook, CT

Information deemed reliable but not guaranteed.

Listing information has been assembled from various sources of varying degrees of reliability. Any information critical to a buying decision should be independently verified.

Information on this this page is provided by the Smart Multiple Listing Service, Inc. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

© Copyright 2026 Smart Multiple Listing Service, Inc.