Osterville Massachusetts Homes for Sale

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39 Tower Hill Road APT 1A Osterville, MA MLS# 22602099 - Image 1

39 Tower Hill Road APT 1A Osterville, MA MLS# 22602099 - Image 2

39 Tower Hill Road APT 1A Osterville, MA MLS# 22602099 - Image 3

39 Tower Hill Road APT 1A Osterville, MA MLS# 22602099 - Image 4

39 Tower Hill Road APT 1A Osterville, MA MLS# 22602099 - Image 5

39 Tower Hill Road APT 1A Osterville, MA MLS# 22602099 - Image 6

39 Tower Hill Road APT 1A Osterville, MA MLS# 22602099 - Image 7

Recently Listed

1 of 7

$625,000

Beds

2.0

Baths

1,159

Sq.Ft.

39 Tower Hill Road APT 1A

Osterville, MA

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 2

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 3

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 4

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 5

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 6

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 7

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 8

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 9

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 10

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 11

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 12

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 13

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 14

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 15

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 16

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 17

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 18

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 19

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 20

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 21

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 22

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 23

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 24

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 25

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 26

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 27

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 28

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 29

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55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 31

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 32

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 33

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 34

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 35

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 36

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 37

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 38

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 39

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 40

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 41

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 42

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 43

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 44

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 45

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 46

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 47

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 48

Recently Listed

1 of 48

$699,000

Beds

2.0

Baths

1,040

Sq.Ft.

55 Seth Goodspeed Way

Osterville, MA

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 2

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 3

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 4

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 5

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 6

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 7

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 8

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 9

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 10

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 11

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 12

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 13

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 14

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 15

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 16

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 17

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 18

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 19

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 20

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 21

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 22

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 23

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 24

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 25

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 26

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 27

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 28

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 29

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 30

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 31

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 32

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 33

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 34

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 35

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 36

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 37

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 38

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 39

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 40

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 41

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 42

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 43

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 44

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 45

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 46

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 47

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 48

30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 49

Recently Listed with Virtual Tour

1 of 49

$3,900,000

Beds

4.1

Baths

4,241

Sq.Ft.

30 Cockachoiset Lane

Osterville, MA

THE TIME TO SELL IS NOW!

12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 1

12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 2

12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 3

12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 4

12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 5

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12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 8

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12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 13

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12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 16

12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 17

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12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 35

12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 36

12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 37

12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 38

12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 39

12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 40

12 Cockachoiset Lane Osterville, MA MLS# 22601973 - Image 41

Recently Listed

1 of 41

$2,950,000

Beds

3.0

Baths

3,178

Sq.Ft.

12 Cockachoiset Lane

Osterville, MA

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 2

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 3

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 4

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 5

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 6

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 7

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 8

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 9

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 10

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 11

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 12

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 13

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 14

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 15

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 16

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 17

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 18

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 19

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 20

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 21

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 22

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 23

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 24

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 25

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 26

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 27

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 28

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 29

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 30

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 31

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 32

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 33

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 34

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 35

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 36

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 37

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 38

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 39

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 40

81 Osterville West Barnstable Road Osterville, MA MLS# 22601935 - Image 41

Recently Listed

1 of 41

$1,950,000

Beds

2.1

Baths

3,084

Sq.Ft.

81 Osterville West Barnstable Road

Osterville, MA

268 Parker Road Osterville, MA MLS# 22601763 - Image 2

268 Parker Road Osterville, MA MLS# 22601763 - Image 3

268 Parker Road Osterville, MA MLS# 22601763 - Image 4

268 Parker Road Osterville, MA MLS# 22601763 - Image 5

268 Parker Road Osterville, MA MLS# 22601763 - Image 6

268 Parker Road Osterville, MA MLS# 22601763 - Image 7

268 Parker Road Osterville, MA MLS# 22601763 - Image 8

268 Parker Road Osterville, MA MLS# 22601763 - Image 9

268 Parker Road Osterville, MA MLS# 22601763 - Image 10

268 Parker Road Osterville, MA MLS# 22601763 - Image 11

268 Parker Road Osterville, MA MLS# 22601763 - Image 12

268 Parker Road Osterville, MA MLS# 22601763 - Image 13

268 Parker Road Osterville, MA MLS# 22601763 - Image 14

268 Parker Road Osterville, MA MLS# 22601763 - Image 15

268 Parker Road Osterville, MA MLS# 22601763 - Image 16

268 Parker Road Osterville, MA MLS# 22601763 - Image 17

268 Parker Road Osterville, MA MLS# 22601763 - Image 18

1 of 18

$3,995,000

Beds

4.1

Baths

6,239

Sq.Ft.

268 Parker Road

Osterville, MA

153 Hickory Hill Circle Osterville, MA MLS# 22601740 - Image 2

153 Hickory Hill Circle Osterville, MA MLS# 22601740 - Image 3

153 Hickory Hill Circle Osterville, MA MLS# 22601740 - Image 4

153 Hickory Hill Circle Osterville, MA MLS# 22601740 - Image 5

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153 Hickory Hill Circle Osterville, MA MLS# 22601740 - Image 7

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153 Hickory Hill Circle Osterville, MA MLS# 22601740 - Image 35

153 Hickory Hill Circle Osterville, MA MLS# 22601740 - Image 36

1 of 36

$899,000

Beds

2.1

Baths

2,585

Sq.Ft.

153 Hickory Hill Circle

Osterville, MA

162 Main Street Osterville, MA MLS# 22601704 - Image 2

162 Main Street Osterville, MA MLS# 22601704 - Image 3

162 Main Street Osterville, MA MLS# 22601704 - Image 4

162 Main Street Osterville, MA MLS# 22601704 - Image 5

162 Main Street Osterville, MA MLS# 22601704 - Image 6

162 Main Street Osterville, MA MLS# 22601704 - Image 7

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162 Main Street Osterville, MA MLS# 22601704 - Image 47

1 of 47

$1,785,000

Beds

2.1

Baths

2,048

Sq.Ft.

162 Main Street

Osterville, MA

42 Oak Lane Osterville, MA MLS# 22601668 - Image 2

42 Oak Lane Osterville, MA MLS# 22601668 - Image 3

42 Oak Lane Osterville, MA MLS# 22601668 - Image 4

42 Oak Lane Osterville, MA MLS# 22601668 - Image 5

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42 Oak Lane Osterville, MA MLS# 22601668 - Image 7

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1 of 66

$849,000

Beds

2.0

Baths

1,848

Sq.Ft.

42 Oak Lane

Osterville, MA

955 Main Street Osterville, MA MLS# 22601611 - Image 2

955 Main Street Osterville, MA MLS# 22601611 - Image 3

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1 of 52

$1,579,000

Beds

2.0

Baths

1,765

Sq.Ft.

955 Main Street

Osterville, MA

21 Cockachoisett Lane Osterville, MA MLS# 22601599 - Image 2

21 Cockachoisett Lane Osterville, MA MLS# 22601599 - Image 3

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21 Cockachoisett Lane Osterville, MA MLS# 22601599 - Image 9

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21 Cockachoisett Lane Osterville, MA MLS# 22601599 - Image 40

1 of 40

$2,900,000

Beds

3.1

Baths

3,015

Sq.Ft.

21 Cockachoisett Lane

Osterville, MA

441 Old Mill Road Osterville, MA MLS# 22601575 - Image 2

441 Old Mill Road Osterville, MA MLS# 22601575 - Image 3

441 Old Mill Road Osterville, MA MLS# 22601575 - Image 4

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1 of 16

$810,000

Beds

2.0

Baths

1,144

Sq.Ft.

441 Old Mill Road

Osterville, MA

39 Tower Hill Road APT 15B Osterville, MA MLS# 22601574 - Image 2

39 Tower Hill Road APT 15B Osterville, MA MLS# 22601574 - Image 3

39 Tower Hill Road APT 15B Osterville, MA MLS# 22601574 - Image 4

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39 Tower Hill Road APT 15B Osterville, MA MLS# 22601574 - Image 29

1 of 29

$719,000

Beds

2.0

Baths

1,260

Sq.Ft.

39 Tower Hill Road APT 15B

Osterville, MA

176 Bumps River RD Road Osterville, MA MLS# 22601545 - Image 2

176 Bumps River RD Road Osterville, MA MLS# 22601545 - Image 3

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Virtual Tour

1 of 54

$1,495,000

Beds

2.1

Baths

2,537

Sq.Ft.

176 Bumps River RD Road

Osterville, MA

170 Sturbridge Drive Osterville, MA MLS# 22601492 - Image 2

170 Sturbridge Drive Osterville, MA MLS# 22601492 - Image 3

170 Sturbridge Drive Osterville, MA MLS# 22601492 - Image 4

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170 Sturbridge Drive Osterville, MA MLS# 22601492 - Image 38

Recently Listed

1 of 38

OPEN HOUSE: Saturday 5/23 10:00 AM - 12:00 PM

$1,150,000

Beds

2.1

Baths

1,992

Sq.Ft.

170 Sturbridge Drive

Osterville, MA

31 Falling Leaf Lane Osterville, MA MLS# 22601349 - Image 2

31 Falling Leaf Lane Osterville, MA MLS# 22601349 - Image 3

31 Falling Leaf Lane Osterville, MA MLS# 22601349 - Image 4

31 Falling Leaf Lane Osterville, MA MLS# 22601349 - Image 5

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1 of 45

$1,199,000

Beds

2.1

Baths

2,190

Sq.Ft.

31 Falling Leaf Lane

Osterville, MA

82 Crystal Lake Road Osterville, MA MLS# 22601140 - Image 2

82 Crystal Lake Road Osterville, MA MLS# 22601140 - Image 3

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1 of 64

$3,475,000

Beds

3.2

Baths

4,364

Sq.Ft.

82 Crystal Lake Road

Osterville, MA

60 Linden Lane Osterville, MA MLS# 22601021 - Image 2

60 Linden Lane Osterville, MA MLS# 22601021 - Image 3

60 Linden Lane Osterville, MA MLS# 22601021 - Image 4

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60 Linden Lane Osterville, MA MLS# 22601021 - Image 23

1 of 23

$949,000

Beds

3.0

Baths

2,000

Sq.Ft.

60 Linden Lane

Osterville, MA

92 Wianno Circle Osterville, MA MLS# 22601032 - Image 2

92 Wianno Circle Osterville, MA MLS# 22601032 - Image 3

92 Wianno Circle Osterville, MA MLS# 22601032 - Image 4

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Virtual Tour

1 of 56

$1,600,000

Beds

3.0

Baths

2,459

Sq.Ft.

92 Wianno Circle

Osterville, MA

177 Bayview Circle Osterville, MA MLS# 22601044 - Image 2

177 Bayview Circle Osterville, MA MLS# 22601044 - Image 3

177 Bayview Circle Osterville, MA MLS# 22601044 - Image 4

177 Bayview Circle Osterville, MA MLS# 22601044 - Image 5

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177 Bayview Circle Osterville, MA MLS# 22601044 - Image 7

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1 of 41

$924,900

Beds

2.1

Baths

2,050

Sq.Ft.

177 Bayview Circle

Osterville, MA

About Osterville

Listings in Osterville, MA: 46
Estimated median home price: $2,747,500

Osterville MA Homes for Sale & Properties

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

Homes for Sale by Price in Osterville, MA

Price	Count
$0 - 100K	1
$100K - 200K	0
$200K - 300K	0
$300K - 400K	0
$400K - 500K	0
$500K - 600K	0
$600K - 700K	3
$700K - 800K	1
$800K - 900K	4
$900K - 1M	2
$1M - Max	35

Homes for Sale by Type in Osterville, MA

Property Type	Count
Single Family	37
Townhouse	0
Condo	3
Commercial	2
Rental	1
Lots and Land	4
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 5/16/2026)

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02655

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Weichert Realtors are marked with the BR Logo and detailed information about them includes the name of the listing broker company. Neither the listing broker nor Weichert Realtors shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

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.

Data is updated as of 5/19/2026. All properties are subject to prior sale, changes, or withdrawal.

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