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

$999,000

Beds

2.0

Baths

1,426

Sq.Ft.

37 Woodland Drive

Old Saybrook, CT

17 College Street Old Saybrook, CT MLS# 24208689 - Image 3

17 College Street Old Saybrook, CT MLS# 24208689 - Image 4

17 College Street Old Saybrook, CT MLS# 24208689 - Image 5

17 College Street Old Saybrook, CT MLS# 24208689 - Image 6

17 College Street Old Saybrook, CT MLS# 24208689 - Image 7

17 College Street Old Saybrook, CT MLS# 24208689 - Image 8

17 College Street Old Saybrook, CT MLS# 24208689 - Image 9

17 College Street Old Saybrook, CT MLS# 24208689 - Image 10

17 College Street Old Saybrook, CT MLS# 24208689 - Image 11

17 College Street Old Saybrook, CT MLS# 24208689 - Image 12

17 College Street Old Saybrook, CT MLS# 24208689 - Image 13

17 College Street Old Saybrook, CT MLS# 24208689 - Image 14

17 College Street Old Saybrook, CT MLS# 24208689 - Image 15

17 College Street Old Saybrook, CT MLS# 24208689 - Image 16

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17 College Street Old Saybrook, CT MLS# 24208689 - Image 18

17 College Street Old Saybrook, CT MLS# 24208689 - Image 19

17 College Street Old Saybrook, CT MLS# 24208689 - Image 20

17 College Street Old Saybrook, CT MLS# 24208689 - Image 21

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17 College Street Old Saybrook, CT MLS# 24208689 - Image 25

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17 College Street Old Saybrook, CT MLS# 24208689 - Image 40

17 College Street Old Saybrook, CT MLS# 24208689 - Image 41

17 College Street Old Saybrook, CT MLS# 24208689 - Image 42

17 College Street Old Saybrook, CT MLS# 24208689 - Image 43

Recently Listed

1 of 43

$999,000

Beds

3.0

Baths

1,960

Sq.Ft.

17 College Street

Old Saybrook, CT

12 Drummers Trail Old Saybrook, CT MLS# 24211855 - Image 3

12 Drummers Trail Old Saybrook, CT MLS# 24211855 - Image 4

12 Drummers Trail Old Saybrook, CT MLS# 24211855 - Image 5

12 Drummers Trail Old Saybrook, CT MLS# 24211855 - Image 6

12 Drummers Trail Old Saybrook, CT MLS# 24211855 - Image 7

12 Drummers Trail Old Saybrook, CT MLS# 24211855 - Image 8

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12 Drummers Trail Old Saybrook, CT MLS# 24211855 - Image 21

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12 Drummers Trail Old Saybrook, CT MLS# 24211855 - Image 37

12 Drummers Trail Old Saybrook, CT MLS# 24211855 - Image 38

12 Drummers Trail Old Saybrook, CT MLS# 24211855 - Image 39

12 Drummers Trail Old Saybrook, CT MLS# 24211855 - Image 40

Recently Listed

1 of 40

$995,000

Beds

3.1

Baths

3,277

Sq.Ft.

12 Drummers Trail

Old Saybrook, CT

THE TIME TO SELL IS NOW!

6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 1

6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 2

6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 3

6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 4

6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 5

6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 6

6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 7

6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 8

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6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 13

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6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 16

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6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 21

6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 22

6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 23

6 Overlook Drive Old Saybrook, CT MLS# 24207853 - Image 24

Recently Listed

1 of 24

$935,000

Beds

3.1

Baths

2,816

Sq.Ft.

6 Overlook Drive

Old Saybrook, CT

$925,000

4,256

Sq.Ft.

621 Boston Post Road

Old Saybrook, CT

65 Knollwood Drive Old Saybrook, CT MLS# 24191006 - Image 3

65 Knollwood Drive Old Saybrook, CT MLS# 24191006 - Image 4

65 Knollwood Drive Old Saybrook, CT MLS# 24191006 - Image 5

65 Knollwood Drive Old Saybrook, CT MLS# 24191006 - Image 6

65 Knollwood Drive Old Saybrook, CT MLS# 24191006 - Image 7

65 Knollwood Drive Old Saybrook, CT MLS# 24191006 - Image 8

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65 Knollwood Drive Old Saybrook, CT MLS# 24191006 - Image 31

65 Knollwood Drive Old Saybrook, CT MLS# 24191006 - Image 32

1 of 32

$925,000

Beds

2.1

Baths

2,153

Sq.Ft.

65 Knollwood Drive

Old Saybrook, CT

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

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 4

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 5

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 6

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 7

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 8

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 9

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 10

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 11

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 12

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 13

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 14

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 15

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 16

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170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 18

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170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 26

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170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 38

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 39

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170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 41

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 42

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 43

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 44

170 Old Post Road Old Saybrook, CT MLS# 24192820 - Image 45

1 of 45

$900,000

Beds

2.1

Baths

2,128

Sq.Ft.

170 Old Post Road

Old Saybrook, CT

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

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

30 Neptune Drive Old Saybrook, CT MLS# 24190267 - Image 5

30 Neptune Drive Old Saybrook, CT MLS# 24190267 - Image 6

30 Neptune Drive Old Saybrook, CT MLS# 24190267 - Image 7

30 Neptune Drive Old Saybrook, CT MLS# 24190267 - Image 8

30 Neptune Drive Old Saybrook, CT MLS# 24190267 - Image 9

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30 Neptune Drive Old Saybrook, CT MLS# 24190267 - Image 11

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30 Neptune Drive Old Saybrook, CT MLS# 24190267 - Image 39

1 of 39

$899,000

Beds

1.1

Baths

1,706

Sq.Ft.

30 Neptune Drive

Old Saybrook, CT

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

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

86 Fenwood Drive Old Saybrook, CT MLS# 24211563 - Image 5

86 Fenwood Drive Old Saybrook, CT MLS# 24211563 - Image 6

86 Fenwood Drive Old Saybrook, CT MLS# 24211563 - Image 7

86 Fenwood Drive Old Saybrook, CT MLS# 24211563 - Image 8

86 Fenwood Drive Old Saybrook, CT MLS# 24211563 - Image 9

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86 Fenwood Drive Old Saybrook, CT MLS# 24211563 - Image 11

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86 Fenwood Drive Old Saybrook, CT MLS# 24211563 - Image 39

Virtual Tour

1 of 39

$859,900

Beds

3.0

Baths

2,210

Sq.Ft.

86 Fenwood Drive

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

18 Old South Cove Road Old Saybrook, CT MLS# 24163559 - Image 5

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1 of 287

$849,950

Beds

1.2

Baths

1,569

Sq.Ft.

18 Old South Cove 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 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

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

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1 of 39

$799,999

Beds

2.0

Baths

1,834

Sq.Ft.

119 Great Hammock Road

Old Saybrook, CT

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

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Virtual Tour

1 of 40

$799,900

Beds

3.0

Baths

2,496

Sq.Ft.

3 Anchorage Lane

Old Saybrook, CT

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

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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

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Address not provided Old Saybrook, CT MLS# 24208703 - Image 38

Address not provided Old Saybrook, CT MLS# 24208703 - Image 39

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

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

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

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25 Uncas Trail Old Saybrook, CT MLS# 24189175 - Image 51

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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71 Knollwood Drive Old Saybrook, CT MLS# 24200281 - Image 59

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

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

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

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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

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

1 of 32

$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 40

1 of 40

$749,000

Beds

2.1

Baths

2,205

Sq.Ft.

6 Nutmeg Circle

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	7
$500K - 600K	4
$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	38
Lots and Land	6
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 10/9/2026)

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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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