Old Saybrook Connecticut Homes for Sale

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100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 1

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 2

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 3

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 4

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 5

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 6

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 7

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 8

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 9

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 10

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 11

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 12

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 13

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 14

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 15

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 16

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 17

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 18

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 19

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 20

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 21

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 22

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 23

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 24

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 25

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 26

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 27

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 28

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 29

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 30

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 31

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 32

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 33

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 34

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 35

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 36

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 37

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 38

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 39

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 40

100 Dudley Avenue F30 Old Saybrook, CT MLS# 24200662 - Image 41

1 of 41

$750,000

Beds

2.1

Baths

1,565

Sq.Ft.

100 Dudley Avenue F30

Old Saybrook, CT

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 3

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 4

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 5

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 6

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 7

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 8

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 9

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25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 11

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 12

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 13

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 14

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 15

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 16

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 17

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 18

25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 19

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25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 24

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25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 26

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25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 28

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25 Sunset Road 18 Old Saybrook, CT MLS# 24205240 - Image 32

1 of 32

OPEN HOUSE: Sunday 10/4 11:00 AM - 1:00 PM

$749,900

Beds

3.1

Baths

1,565

Sq.Ft.

25 Sunset Road 18

Old Saybrook, CT

6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 3

6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 4

6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 5

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6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 7

6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 8

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6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 11

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6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 21

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6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 25

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6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 31

6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 32

6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 33

6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 34

6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 35

6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 36

6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 37

6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 38

6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 39

6 Nutmeg Circle Old Saybrook, CT MLS# 24204473 - Image 40

1 of 40

$749,000

Beds

2.1

Baths

2,205

Sq.Ft.

6 Nutmeg Circle

Old Saybrook, CT

THE TIME TO SELL IS NOW!

18 Shepard Street Old Saybrook, CT MLS# 24201611 - Image 1

18 Shepard Street Old Saybrook, CT MLS# 24201611 - Image 2

18 Shepard Street Old Saybrook, CT MLS# 24201611 - Image 3

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18 Shepard Street Old Saybrook, CT MLS# 24201611 - Image 40

1 of 40

$699,900

Beds

2.0

Baths

2,114

Sq.Ft.

18 Shepard Street

Old Saybrook, CT

6 Willard Street Old Saybrook, CT MLS# 24202240 - Image 3

6 Willard Street Old Saybrook, CT MLS# 24202240 - Image 4

6 Willard Street Old Saybrook, CT MLS# 24202240 - Image 5

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6 Willard Street Old Saybrook, CT MLS# 24202240 - Image 7

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6 Willard Street Old Saybrook, CT MLS# 24202240 - Image 37

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6 Willard Street Old Saybrook, CT MLS# 24202240 - Image 39

6 Willard Street Old Saybrook, CT MLS# 24202240 - Image 40

1 of 40

$699,900

Beds

2.0

Baths

1,913

Sq.Ft.

6 Willard Street

Old Saybrook, CT

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 3

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 4

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 5

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 6

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 7

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11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 41

1 of 41

$699,000

Beds

2.1

Baths

2,755

Sq.Ft.

11 Kitteridge Hill Road

Old Saybrook, CT

5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 3

5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 4

5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 5

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5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 40

1 of 40

$699,000

Beds

3.0

Baths

2,606

Sq.Ft.

5 Connally Drive

Old Saybrook, CT

1333 Boston Post Road 1 Old Saybrook, CT MLS# 24139358 - Image 3

1333 Boston Post Road 1 Old Saybrook, CT MLS# 24139358 - Image 4

1333 Boston Post Road 1 Old Saybrook, CT MLS# 24139358 - Image 5

1333 Boston Post Road 1 Old Saybrook, CT MLS# 24139358 - Image 6

1333 Boston Post Road 1 Old Saybrook, CT MLS# 24139358 - Image 7

1333 Boston Post Road 1 Old Saybrook, CT MLS# 24139358 - Image 8

1 of 8

$695,000

0.0

Baths

1333 Boston Post Road 1

Old Saybrook, CT

9 Old Colony Road Old Saybrook, CT MLS# 24190279 - Image 3

9 Old Colony Road Old Saybrook, CT MLS# 24190279 - Image 4

9 Old Colony Road Old Saybrook, CT MLS# 24190279 - Image 5

1 of 5

OPEN HOUSE: Sunday 10/4 11:00 AM - 1:00 PM

$675,000

Beds

2.0

Baths

1,344

Sq.Ft.

9 Old Colony Road

Old Saybrook, CT

96 Chalker Beach Road Old Saybrook, CT MLS# 24174666 - Image 3

96 Chalker Beach Road Old Saybrook, CT MLS# 24174666 - Image 4

96 Chalker Beach Road Old Saybrook, CT MLS# 24174666 - Image 5

96 Chalker Beach Road Old Saybrook, CT MLS# 24174666 - Image 6

96 Chalker Beach Road Old Saybrook, CT MLS# 24174666 - Image 7

96 Chalker Beach Road Old Saybrook, CT MLS# 24174666 - Image 8

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1 of 35

$649,900

Beds

1.0

Baths

968

Sq.Ft.

96 Chalker Beach Road

Old Saybrook, CT

8 Kenn Road Old Saybrook, CT MLS# 24196847 - Image 3

8 Kenn Road Old Saybrook, CT MLS# 24196847 - Image 4

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1 of 40

$649,000

Beds

2.0

Baths

1,040

Sq.Ft.

8 Kenn Road

Old Saybrook, CT

$599,500

1.0

Baths

4,157

Sq.Ft.

523 Boston Post Road

Old Saybrook, CT

46 Farview Avenue Old Saybrook, CT MLS# 24196117 - Image 3

46 Farview Avenue Old Saybrook, CT MLS# 24196117 - Image 4

46 Farview Avenue Old Saybrook, CT MLS# 24196117 - Image 5

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1 of 35

$599,000

Beds

2.0

Baths

1,552

Sq.Ft.

46 Farview Avenue

Old Saybrook, CT

61 Springbrook Road Old Saybrook, CT MLS# 24204068 - Image 3

61 Springbrook Road Old Saybrook, CT MLS# 24204068 - Image 4

61 Springbrook Road Old Saybrook, CT MLS# 24204068 - Image 5

61 Springbrook Road Old Saybrook, CT MLS# 24204068 - Image 6

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61 Springbrook Road Old Saybrook, CT MLS# 24204068 - Image 16

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61 Springbrook Road Old Saybrook, CT MLS# 24204068 - Image 18

61 Springbrook Road Old Saybrook, CT MLS# 24204068 - Image 19

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61 Springbrook Road Old Saybrook, CT MLS# 24204068 - Image 21

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61 Springbrook Road Old Saybrook, CT MLS# 24204068 - Image 24

61 Springbrook Road Old Saybrook, CT MLS# 24204068 - Image 25

1 of 25

OPEN HOUSE: Saturday 10/3 12:00 PM - 2:00 PM

$525,000

Beds

3.0

Baths

1,296

Sq.Ft.

61 Springbrook Road

Old Saybrook, CT

1324 Boston Post Road Old Saybrook, CT MLS# 24198488 - Image 3

1324 Boston Post Road Old Saybrook, CT MLS# 24198488 - Image 4

1324 Boston Post Road Old Saybrook, CT MLS# 24198488 - Image 5

1324 Boston Post Road Old Saybrook, CT MLS# 24198488 - Image 6

1324 Boston Post Road Old Saybrook, CT MLS# 24198488 - Image 7

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1324 Boston Post Road Old Saybrook, CT MLS# 24198488 - Image 20

1 of 20

$515,000

Beds

1.0

Baths

1,104

Sq.Ft.

1324 Boston Post Road

Old Saybrook, CT

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 3

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 4

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 5

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 6

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 7

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 8

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 9

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 10

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 11

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 12

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 13

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 14

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 15

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 16

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 17

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 18

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 19

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 20

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 21

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 22

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 23

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 24

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 25

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 26

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 27

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 28

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 29

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 30

256 Hidden Cove Road 256 Old Saybrook, CT MLS# 24180111 - Image 31

1 of 31

$510,000

Beds

1.1

Baths

1,557

Sq.Ft.

256 Hidden Cove Road 256

Old Saybrook, CT

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 3

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 4

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 5

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 6

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 7

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 8

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 9

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 10

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 11

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 12

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 13

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 14

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 15

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 16

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 17

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35 School House Road Old Saybrook, CT MLS# 24202909 - Image 21

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35 School House Road Old Saybrook, CT MLS# 24202909 - Image 31

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35 School House Road Old Saybrook, CT MLS# 24202909 - Image 33

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35 School House Road Old Saybrook, CT MLS# 24202909 - Image 37

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35 School House Road Old Saybrook, CT MLS# 24202909 - Image 39

35 School House Road Old Saybrook, CT MLS# 24202909 - Image 40

1 of 40

$499,999

Beds

1.0

Baths

2,718

Sq.Ft.

35 School House Road

Old Saybrook, CT

$499,995

2.0

Baths

369 Boston Post Road

Old Saybrook, CT

1 Briarcliffe Trail Old Saybrook, CT MLS# 24208270 - Image 3

1 Briarcliffe Trail Old Saybrook, CT MLS# 24208270 - Image 4

1 Briarcliffe Trail Old Saybrook, CT MLS# 24208270 - Image 5

1 Briarcliffe Trail Old Saybrook, CT MLS# 24208270 - Image 6

1 Briarcliffe Trail Old Saybrook, CT MLS# 24208270 - Image 7

1 Briarcliffe Trail Old Saybrook, CT MLS# 24208270 - Image 8

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1 Briarcliffe Trail Old Saybrook, CT MLS# 24208270 - Image 33

1 Briarcliffe Trail Old Saybrook, CT MLS# 24208270 - Image 34

Recently Listed

1 of 34

$499,900

Beds

1.0

Baths

1,373

Sq.Ft.

1 Briarcliffe Trail

Old Saybrook, CT

$495,000

0.0

Baths

0 Middlesex Turnpike

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: 68
Estimated median home price: $800,000

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	2
$200K - 300K	3
$300K - 400K	0
$400K - 500K	5
$500K - 600K	6
$600K - 700K	8
$700K - 800K	10
$800K - 900K	4
$900K - 1M	5
$1M - Max	24

Homes for Sale by Type in Old Saybrook, CT

Property Type	Count
Single Family	49
Townhouse	0
Condo	4
Commercial	9
Rental	41
Lots and Land	6
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 10/3/2026)

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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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