Old Saybrook Connecticut Homes for Sale

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37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 1

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 2

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 3

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 4

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 5

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 6

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 7

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 8

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 9

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 10

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 11

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 12

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 13

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 14

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 15

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 16

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 17

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 18

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 19

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 20

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 21

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 22

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 23

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 24

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 25

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 26

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 27

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 28

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 29

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 30

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 31

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 32

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 33

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 34

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 35

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 36

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 37

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 38

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 39

37 Woodland Drive Old Saybrook, CT MLS# 24186222 - Image 40

1 of 40

$1,075,000

Beds

2.0

Baths

1,426

Sq.Ft.

37 Woodland Drive

Old Saybrook, CT

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 3

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 4

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 5

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 6

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 7

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 8

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 9

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 10

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 11

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 12

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 13

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 14

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 15

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 16

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 17

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 18

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 19

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 20

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 21

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 22

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 23

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 24

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 25

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 26

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 27

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 28

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 29

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 30

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 31

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 32

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 33

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 34

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 35

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 36

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 37

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 38

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 39

93 Elm Street Old Saybrook, CT MLS# 24167568 - Image 40

1 of 40

$1,050,000

2.0

Baths

6,897

Sq.Ft.

93 Elm Street

Old Saybrook, CT

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 3

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 4

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 5

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 6

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 7

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 8

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 9

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 10

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 11

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 12

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 13

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 14

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 15

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 16

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 17

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 18

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 19

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 20

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 21

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 22

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 23

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 24

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 25

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 26

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 27

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 28

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 29

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 30

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 31

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 32

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 33

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 34

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 35

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 36

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 37

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 38

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 39

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 40

95 Middletown Avenue Old Saybrook, CT MLS# 24176978 - Image 41

1 of 41

$1,049,900

Beds

2.0

Baths

1,566

Sq.Ft.

95 Middletown Avenue

Old Saybrook, CT

THE TIME TO SELL IS NOW!

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 1

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 2

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 3

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 4

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 5

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34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 8

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 9

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34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 11

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 12

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 13

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 14

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 15

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 16

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 17

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 18

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 19

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 20

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 21

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 22

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 23

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34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 27

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34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 31

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34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 33

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 34

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 35

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 36

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 37

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 38

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 39

34 Briarcliffe Trail Old Saybrook, CT MLS# 24182838 - Image 40

Virtual Tour

1 of 40

$999,900

Beds

3.0

Baths

3,720

Sq.Ft.

34 Briarcliffe Trail

Old Saybrook, CT

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 3

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 4

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 5

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 6

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 7

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 8

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 9

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 10

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 11

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 12

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 13

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 14

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 15

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 16

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6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 18

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 19

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6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 21

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6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 25

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6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 27

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 28

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 29

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 30

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 31

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 32

6 Trolley Crossing Old Saybrook, CT MLS# 24177743 - Image 33

1 of 33

$997,000

Beds

2.1

Baths

3,917

Sq.Ft.

6 Trolley Crossing

Old Saybrook, CT

25 Sheffield Street 3 Old Saybrook, CT MLS# 24167074 - Image 3

25 Sheffield Street 3 Old Saybrook, CT MLS# 24167074 - Image 4

25 Sheffield Street 3 Old Saybrook, CT MLS# 24167074 - Image 5

25 Sheffield Street 3 Old Saybrook, CT MLS# 24167074 - Image 6

25 Sheffield Street 3 Old Saybrook, CT MLS# 24167074 - Image 7

25 Sheffield Street 3 Old Saybrook, CT MLS# 24167074 - Image 8

25 Sheffield Street 3 Old Saybrook, CT MLS# 24167074 - Image 9

25 Sheffield Street 3 Old Saybrook, CT MLS# 24167074 - Image 10

25 Sheffield Street 3 Old Saybrook, CT MLS# 24167074 - Image 11

25 Sheffield Street 3 Old Saybrook, CT MLS# 24167074 - Image 12

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25 Sheffield Street 3 Old Saybrook, CT MLS# 24167074 - Image 21

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25 Sheffield Street 3 Old Saybrook, CT MLS# 24167074 - Image 37

25 Sheffield Street 3 Old Saybrook, CT MLS# 24167074 - Image 38

1 of 38

$968,800

Beds

2.1

Baths

2,823

Sq.Ft.

25 Sheffield Street 3

Old Saybrook, CT

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 3

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 4

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 5

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 6

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 7

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 8

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 9

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 10

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 11

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 12

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 13

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 14

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 15

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 16

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28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 18

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28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 21

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 22

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28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 27

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28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 31

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28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 35

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28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 37

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28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 39

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 40

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 41

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 42

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28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 46

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28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 50

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28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 53

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28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 55

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 56

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28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 61

28 Gates Road Old Saybrook, CT MLS# 24184811 - Image 62

1 of 62

OPEN HOUSE: Sunday 8/2 1:00 PM - 3:00 PM

$949,000

Beds

1.1

Baths

1,208

Sq.Ft.

28 Gates Road

Old Saybrook, CT

25 Sheffield Street 7 Old Saybrook, CT MLS# 24171224 - Image 3

25 Sheffield Street 7 Old Saybrook, CT MLS# 24171224 - Image 4

25 Sheffield Street 7 Old Saybrook, CT MLS# 24171224 - Image 5

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25 Sheffield Street 7 Old Saybrook, CT MLS# 24171224 - Image 7

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25 Sheffield Street 7 Old Saybrook, CT MLS# 24171224 - Image 40

1 of 40

$940,000

Beds

2.2

Baths

2,151

Sq.Ft.

25 Sheffield Street 7

Old Saybrook, CT

$925,000

4,256

Sq.Ft.

621 Boston Post Road

Old Saybrook, CT

18 Old South Cove Road Old Saybrook, CT MLS# 24163559 - Image 3

18 Old South Cove Road Old Saybrook, CT MLS# 24163559 - Image 4

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1 of 169

$899,000

Beds

1.2

Baths

1,569

Sq.Ft.

18 Old South Cove Road

Old Saybrook, CT

119 Great Hammock Road Old Saybrook, CT MLS# 24189317 - Image 3

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Recently Listed

1 of 39

$899,000

Beds

2.0

Baths

1,834

Sq.Ft.

119 Great Hammock Road

Old Saybrook, CT

86 Fenwood Drive Old Saybrook, CT MLS# 24185294 - Image 3

86 Fenwood Drive Old Saybrook, CT MLS# 24185294 - Image 4

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Virtual Tour

1 of 39

$874,900

Beds

3.0

Baths

2,209

Sq.Ft.

86 Fenwood Drive

Old Saybrook, CT

9 Barley Hill Road Old Saybrook, CT MLS# 24177311 - Image 3

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1 of 39

$850,000

Beds

3.1

Baths

3,544

Sq.Ft.

9 Barley Hill Road

Old Saybrook, CT

28 Bellaire Drive Old Saybrook, CT MLS# 24188825 - Image 3

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1 of 40

$850,000

Beds

2.0

Baths

1,175

Sq.Ft.

28 Bellaire Drive

Old Saybrook, CT

3 Anchorage Lane Old Saybrook, CT MLS# 24189326 - Image 3

3 Anchorage Lane Old Saybrook, CT MLS# 24189326 - Image 4

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Virtual Tour

1 of 42

$849,900

Beds

3.0

Baths

2,496

Sq.Ft.

3 Anchorage Lane

Old Saybrook, CT

About Old Saybrook

The Long Island Sound community of Old Saybrook is well known as a summer vacation retreat, doubling the population in the warmer months. Westbrook extends four miles along the shore at the eastern end of Long Island Sound, with an inland boundary that reaches the towns of Essex and Deep River.

Listings in Old Saybrook, CT: 78
Estimated median home price: $912,000

Old Saybrook CT Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Old Saybrook, Connecticut real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Old Saybrook, CT.

Homes for Sale by Price in Old Saybrook, CT

Price	Count
$0 - 100K	1
$100K - 200K	1
$200K - 300K	1
$300K - 400K	2
$400K - 500K	4
$500K - 600K	10
$600K - 700K	10
$700K - 800K	4
$800K - 900K	6
$900K - 1M	6
$1M - Max	33

Homes for Sale by Type in Old Saybrook, CT

Property Type	Count
Single Family	58
Townhouse	0
Condo	6
Commercial	10
Rental	41
Lots and Land	4
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 7/28/2026)

Find Properties in Old Saybrook, CT

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06475

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.

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Old Saybrook Connecticut Homes for Sale

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