Old Saybrook Connecticut Homes for Sale

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

1333 Boston Post Road 1 Old Saybrook, CT MLS# 24139358 - Image 2

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

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

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 8

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 9

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 10

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

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 12

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 13

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 14

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 15

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 16

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 17

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 18

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 19

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 20

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 21

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11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 24

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 25

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11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 27

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11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 29

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 30

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 31

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11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 33

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 34

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 35

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11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 37

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 38

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 39

11 Kitteridge Hill Road Old Saybrook, CT MLS# 24197434 - Image 40

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

5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 6

5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 7

5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 8

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5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 11

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5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 16

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5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 18

5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 19

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5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 33

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5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 38

5 Connally Drive Old Saybrook, CT MLS# 24208801 - Image 39

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

Recently Listed

1 of 40

OPEN HOUSE: Saturday 10/10 11:00 AM - 2:00 PM

$699,000

Beds

3.0

Baths

2,606

Sq.Ft.

5 Connally Drive

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 40

1 of 40

$699,900

Beds

2.0

Baths

1,913

Sq.Ft.

6 Willard Street

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

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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

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

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1 of 32

$749,900

Beds

3.1

Baths

1,565

Sq.Ft.

25 Sunset Road 18

Old Saybrook, CT

25 Uncas Trail Old Saybrook, CT MLS# 24189175 - Image 3

25 Uncas Trail Old Saybrook, CT MLS# 24189175 - Image 4

25 Uncas Trail Old Saybrook, CT MLS# 24189175 - Image 5

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25 Uncas Trail Old Saybrook, CT MLS# 24189175 - Image 52

1 of 52

$750,000

Beds

2.0

Baths

1,760

Sq.Ft.

25 Uncas Trail

Old Saybrook, CT

71 Knollwood Drive Old Saybrook, CT MLS# 24200281 - Image 3

71 Knollwood Drive Old Saybrook, CT MLS# 24200281 - Image 4

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1 of 59

$750,000

Beds

1.1

Baths

1,856

Sq.Ft.

71 Knollwood Drive

Old Saybrook, CT

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

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1 of 41

$750,000

Beds

2.1

Baths

1,565

Sq.Ft.

100 Dudley Avenue F30

Old Saybrook, CT

Address not provided Old Saybrook, CT MLS# 24208703 - Image 3

Address not provided Old Saybrook, CT MLS# 24208703 - Image 4

Address not provided Old Saybrook, CT MLS# 24208703 - Image 5

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Address not provided Old Saybrook, CT MLS# 24208703 - Image 9

Address not provided Old Saybrook, CT MLS# 24208703 - Image 10

Address not provided Old Saybrook, CT MLS# 24208703 - Image 11

Address not provided Old Saybrook, CT MLS# 24208703 - Image 12

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Address not provided Old Saybrook, CT MLS# 24208703 - Image 14

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Address not provided Old Saybrook, CT MLS# 24208703 - Image 16

Address not provided Old Saybrook, CT MLS# 24208703 - Image 17

Address not provided Old Saybrook, CT MLS# 24208703 - Image 18

Address not provided Old Saybrook, CT MLS# 24208703 - Image 19

Address not provided Old Saybrook, CT MLS# 24208703 - Image 20

Address not provided Old Saybrook, CT MLS# 24208703 - Image 21

Address not provided Old Saybrook, CT MLS# 24208703 - Image 22

Address not provided Old Saybrook, CT MLS# 24208703 - Image 23

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Address not provided Old Saybrook, CT MLS# 24208703 - Image 25

Address not provided Old Saybrook, CT MLS# 24208703 - Image 26

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Address not provided Old Saybrook, CT MLS# 24208703 - Image 40

1 of 40

$780,000

Beds

2.0

Baths

1,593

Sq.Ft.

Address not provided

Old Saybrook, CT

5 Tudor Court East Old Saybrook, CT MLS# 24204260 - Image 3

5 Tudor Court East Old Saybrook, CT MLS# 24204260 - Image 4

5 Tudor Court East Old Saybrook, CT MLS# 24204260 - Image 5

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5 Tudor Court East Old Saybrook, CT MLS# 24204260 - Image 23

5 Tudor Court East Old Saybrook, CT MLS# 24204260 - Image 24

5 Tudor Court East Old Saybrook, CT MLS# 24204260 - Image 25

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5 Tudor Court East Old Saybrook, CT MLS# 24204260 - Image 39

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5 Tudor Court East Old Saybrook, CT MLS# 24204260 - Image 41

5 Tudor Court East Old Saybrook, CT MLS# 24204260 - Image 42

1 of 42

$795,000

Beds

1.0

Baths

2,002

Sq.Ft.

5 Tudor Court East

Old Saybrook, CT

3 Anchorage Lane Old Saybrook, CT MLS# 24205326 - Image 3

3 Anchorage Lane Old Saybrook, CT MLS# 24205326 - Image 4

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3 Anchorage Lane Old Saybrook, CT MLS# 24205326 - Image 38

3 Anchorage Lane Old Saybrook, CT MLS# 24205326 - Image 39

3 Anchorage Lane Old Saybrook, CT MLS# 24205326 - Image 40

Virtual Tour

1 of 40

OPEN HOUSE: Saturday 10/10 11:00 AM - 1:00 PM

$799,900

Beds

3.0

Baths

2,496

Sq.Ft.

3 Anchorage Lane

Old Saybrook, CT

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

119 Great Hammock Road Old Saybrook, CT MLS# 24189317 - Image 4

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119 Great Hammock Road Old Saybrook, CT MLS# 24189317 - Image 39

1 of 39

$799,999

Beds

2.0

Baths

1,834

Sq.Ft.

119 Great Hammock Road

Old Saybrook, CT

25 River Avenue Old Saybrook, CT MLS# 24183581 - Image 3

25 River Avenue Old Saybrook, CT MLS# 24183581 - Image 4

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25 River Avenue Old Saybrook, CT MLS# 24183581 - Image 23

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25 River Avenue Old Saybrook, CT MLS# 24183581 - Image 25

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25 River Avenue Old Saybrook, CT MLS# 24183581 - Image 38

Virtual Tour

1 of 38

OPEN HOUSE: Sunday 10/11 12:00 PM - 2:00 PM

$800,000

Beds

1.0

Baths

1,478

Sq.Ft.

25 River Avenue

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 282

$849,950

Beds

1.2

Baths

1,569

Sq.Ft.

18 Old South Cove Road

Old Saybrook, CT

86 Fenwood Drive Old Saybrook, CT MLS# 24211563 - Image 3

86 Fenwood Drive Old Saybrook, CT MLS# 24211563 - Image 4

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Recently Listed with Virtual Tour

1 of 39

$859,900

Beds

3.0

Baths

2,210

Sq.Ft.

86 Fenwood Drive

Old Saybrook, CT

30 Neptune Drive Old Saybrook, CT MLS# 24190267 - Image 3

30 Neptune Drive Old Saybrook, CT MLS# 24190267 - Image 4

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1 of 39

$899,000

Beds

1.1

Baths

1,706

Sq.Ft.

30 Neptune Drive

Old Saybrook, CT

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 3

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1 of 45

$900,000

Beds

2.1

Baths

2,128

Sq.Ft.

170 Old Post Road

Old Saybrook, CT

$925,000

4,256

Sq.Ft.

621 Boston Post Road

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: 67
Estimated median home price: $799,999

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	6
$500K - 600K	5
$600K - 700K	8
$700K - 800K	10
$800K - 900K	4
$900K - 1M	6
$1M - Max	22

Homes for Sale by Type in Old Saybrook, CT

Property Type	Count
Single Family	48
Townhouse	0
Condo	4
Commercial	9
Rental	37
Lots and Land	6
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 10/7/2026)

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06475

Information deemed reliable but not guaranteed.

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