Osterville Massachusetts Homes for Sale

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30 Cockachoiset Lane Osterville, MA MLS# 22601972 - Image 1

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

Virtual Tour

1 of 49

$3,900,000

Beds

4.1

Baths

4,241

Sq.Ft.

30 Cockachoiset Lane

Osterville, MA

93 Oyster Way Osterville, MA MLS# 22601594 - Image 2

93 Oyster Way Osterville, MA MLS# 22601594 - Image 3

93 Oyster Way Osterville, MA MLS# 22601594 - Image 4

93 Oyster Way Osterville, MA MLS# 22601594 - Image 5

93 Oyster Way Osterville, MA MLS# 22601594 - Image 6

93 Oyster Way Osterville, MA MLS# 22601594 - Image 7

93 Oyster Way Osterville, MA MLS# 22601594 - Image 8

93 Oyster Way Osterville, MA MLS# 22601594 - Image 9

93 Oyster Way Osterville, MA MLS# 22601594 - Image 10

93 Oyster Way Osterville, MA MLS# 22601594 - Image 11

93 Oyster Way Osterville, MA MLS# 22601594 - Image 12

93 Oyster Way Osterville, MA MLS# 22601594 - Image 13

93 Oyster Way Osterville, MA MLS# 22601594 - Image 14

93 Oyster Way Osterville, MA MLS# 22601594 - Image 15

93 Oyster Way Osterville, MA MLS# 22601594 - Image 16

93 Oyster Way Osterville, MA MLS# 22601594 - Image 17

93 Oyster Way Osterville, MA MLS# 22601594 - Image 18

93 Oyster Way Osterville, MA MLS# 22601594 - Image 19

93 Oyster Way Osterville, MA MLS# 22601594 - Image 20

93 Oyster Way Osterville, MA MLS# 22601594 - Image 21

93 Oyster Way Osterville, MA MLS# 22601594 - Image 22

93 Oyster Way Osterville, MA MLS# 22601594 - Image 23

93 Oyster Way Osterville, MA MLS# 22601594 - Image 24

Virtual Tour

1 of 24

$4,795,000

Beds

4.0

Baths

4,964

Sq.Ft.

93 Oyster Way

Osterville, MA

804 Main Street Osterville, MA MLS# 22500909 - Image 2

804 Main Street Osterville, MA MLS# 22500909 - Image 3

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804 Main Street Osterville, MA MLS# 22500909 - Image 49

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804 Main Street Osterville, MA MLS# 22500909 - Image 56

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804 Main Street Osterville, MA MLS# 22500909 - Image 65

1 of 65

$5,900,000

19,304

Sq.Ft.

804 Main Street

Osterville, MA

THE TIME TO SELL IS NOW!

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 1

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 2

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 3

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 4

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 5

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 6

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 7

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 8

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 9

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 10

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 11

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 12

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 13

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 14

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 15

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 16

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179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 37

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179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 39

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 40

179 Pineleigh Path Osterville, MA MLS# 22602488 - Image 41

Recently Listed

1 of 41

$5,950,000

Beds

5.3

Baths

8,740

Sq.Ft.

179 Pineleigh Path

Osterville, MA

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 2

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 3

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 4

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 5

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 6

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 7

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 8

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440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 11

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440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 15

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 16

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440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 41

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 42

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 43

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 44

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 45

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 46

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 47

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 48

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440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 55

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 56

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 57

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440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 63

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440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 65

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440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 67

440 Grand Island Drive Osterville, MA MLS# 22502682 - Image 68

Virtual Tour

1 of 68

$7,750,000

Beds

9.2

Baths

11,546

Sq.Ft.

440 Grand Island Drive

Osterville, MA

255 Bayberry Way Osterville, MA MLS# 22601177 - Image 2

255 Bayberry Way Osterville, MA MLS# 22601177 - Image 3

255 Bayberry Way Osterville, MA MLS# 22601177 - Image 4

255 Bayberry Way Osterville, MA MLS# 22601177 - Image 5

255 Bayberry Way Osterville, MA MLS# 22601177 - Image 6

255 Bayberry Way Osterville, MA MLS# 22601177 - Image 7

255 Bayberry Way Osterville, MA MLS# 22601177 - Image 8

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255 Bayberry Way Osterville, MA MLS# 22601177 - Image 11

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255 Bayberry Way Osterville, MA MLS# 22601177 - Image 13

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255 Bayberry Way Osterville, MA MLS# 22601177 - Image 16

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255 Bayberry Way Osterville, MA MLS# 22601177 - Image 18

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255 Bayberry Way Osterville, MA MLS# 22601177 - Image 21

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255 Bayberry Way Osterville, MA MLS# 22601177 - Image 39

255 Bayberry Way Osterville, MA MLS# 22601177 - Image 40

255 Bayberry Way Osterville, MA MLS# 22601177 - Image 41

255 Bayberry Way Osterville, MA MLS# 22601177 - Image 42

255 Bayberry Way Osterville, MA MLS# 22601177 - Image 43

255 Bayberry Way Osterville, MA MLS# 22601177 - Image 44

1 of 44

$7,900,000

Beds

6.0

Baths

4,896

Sq.Ft.

255 Bayberry Way

Osterville, MA

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 2

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 3

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 4

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 5

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 6

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 7

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 8

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 9

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 10

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 11

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 12

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 13

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 14

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 15

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 16

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 17

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 18

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 19

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 20

850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 21

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850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 24

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850 Sea View Avenue Osterville, MA MLS# 22504438 - Image 70

Virtual Tour

1 of 70

$7,950,000

Beds

7.2

Baths

7,350

Sq.Ft.

850 Sea View Avenue

Osterville, MA

46 Great Bay Road Osterville, MA MLS# 22602282 - Image 2

46 Great Bay Road Osterville, MA MLS# 22602282 - Image 3

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Recently Listed

1 of 54

$8,500,000

Beds

4.2

Baths

4,831

Sq.Ft.

46 Great Bay Road

Osterville, MA

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 2

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 3

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 4

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 5

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 6

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 7

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 8

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 9

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 10

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 11

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 12

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 13

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 14

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 15

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 16

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 17

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 18

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 19

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 20

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 21

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 22

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 23

207 Crystal Lake Road Osterville, MA MLS# 22600636 - Image 24

New Construction

1 of 24

$8,750,000

Beds

5.1

Baths

6,500

Sq.Ft.

207 Crystal Lake Road

Osterville, MA

168 Garrison Lane Osterville, MA MLS# 22505080 - Image 2

168 Garrison Lane Osterville, MA MLS# 22505080 - Image 3

168 Garrison Lane Osterville, MA MLS# 22505080 - Image 4

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168 Garrison Lane Osterville, MA MLS# 22505080 - Image 21

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168 Garrison Lane Osterville, MA MLS# 22505080 - Image 23

168 Garrison Lane Osterville, MA MLS# 22505080 - Image 24

168 Garrison Lane Osterville, MA MLS# 22505080 - Image 25

168 Garrison Lane Osterville, MA MLS# 22505080 - Image 26

168 Garrison Lane Osterville, MA MLS# 22505080 - Image 27

168 Garrison Lane Osterville, MA MLS# 22505080 - Image 28

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168 Garrison Lane Osterville, MA MLS# 22505080 - Image 36

168 Garrison Lane Osterville, MA MLS# 22505080 - Image 37

168 Garrison Lane Osterville, MA MLS# 22505080 - Image 38

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168 Garrison Lane Osterville, MA MLS# 22505080 - Image 40

168 Garrison Lane Osterville, MA MLS# 22505080 - Image 41

168 Garrison Lane Osterville, MA MLS# 22505080 - Image 42

168 Garrison Lane Osterville, MA MLS# 22505080 - Image 43

Virtual Tour

1 of 43

$8,995,000

Beds

5.1

Baths

7,565

Sq.Ft.

168 Garrison Lane

Osterville, MA

14 Indian Trail Osterville, MA MLS# 22503092 - Image 2

14 Indian Trail Osterville, MA MLS# 22503092 - Image 3

14 Indian Trail Osterville, MA MLS# 22503092 - Image 4

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14 Indian Trail Osterville, MA MLS# 22503092 - Image 43

Virtual Tour

1 of 43

$9,850,000

Beds

3.2

Baths

3,087

Sq.Ft.

14 Indian Trail

Osterville, MA

501 Eel River Road Osterville, MA MLS# 22404283 - Image 2

501 Eel River Road Osterville, MA MLS# 22404283 - Image 3

501 Eel River Road Osterville, MA MLS# 22404283 - Image 4

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501 Eel River Road Osterville, MA MLS# 22404283 - Image 50

Virtual Tour

1 of 50

$9,950,000

Beds

7.2

Baths

8,203

Sq.Ft.

501 Eel River Road

Osterville, MA

109 Eel River Road Osterville, MA MLS# 22602692 - Image 2

109 Eel River Road Osterville, MA MLS# 22602692 - Image 3

109 Eel River Road Osterville, MA MLS# 22602692 - Image 4

109 Eel River Road Osterville, MA MLS# 22602692 - Image 5

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109 Eel River Road Osterville, MA MLS# 22602692 - Image 7

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109 Eel River Road Osterville, MA MLS# 22602692 - Image 48

Recently Listed with Virtual Tour

1 of 48

$10,500,000

Beds

5.1

Baths

6,368

Sq.Ft.

109 Eel River Road

Osterville, MA

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 2

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 3

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 4

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 5

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 6

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 7

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 8

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 9

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 10

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 11

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 12

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 13

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 14

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 15

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 16

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48 Starboard Lane Osterville, MA MLS# 22602716 - Image 21

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48 Starboard Lane Osterville, MA MLS# 22602716 - Image 41

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48 Starboard Lane Osterville, MA MLS# 22602716 - Image 45

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 46

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 47

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 48

48 Starboard Lane Osterville, MA MLS# 22602716 - Image 49

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48 Starboard Lane Osterville, MA MLS# 22602716 - Image 61

Recently Listed

1 of 61

$11,950,000

Beds

6.2

Baths

8,387

Sq.Ft.

48 Starboard Lane

Osterville, MA

71 Sand Point Osterville, MA MLS# 22500873 - Image 2

71 Sand Point Osterville, MA MLS# 22500873 - Image 3

71 Sand Point Osterville, MA MLS# 22500873 - Image 4

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71 Sand Point Osterville, MA MLS# 22500873 - Image 45

Virtual Tour

1 of 45

$12,250,000

Beds

4.2

Baths

5,747

Sq.Ft.

71 Sand Point

Osterville, MA

About Osterville

Listings in Osterville, MA: 54
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	2
$600K - 700K	3
$700K - 800K	1
$800K - 900K	5
$900K - 1M	3
$1M - Max	39

Homes for Sale by Type in Osterville, MA

Property Type	Count
Single Family	43
Townhouse	0
Condo	5
Commercial	2
Rental	2
Lots and Land	4
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 6/7/2026)

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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 6/8/2026. All properties are subject to prior sale, changes, or withdrawal.

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