Osterville Massachusetts Homes for Sale

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1112 Main Street STE 1 Osterville, MA MLS# 22605407 - Image 1

1112 Main Street STE 1 Osterville, MA MLS# 22605407 - Image 2

1112 Main Street STE 1 Osterville, MA MLS# 22605407 - Image 3

1112 Main Street STE 1 Osterville, MA MLS# 22605407 - Image 4

1112 Main Street STE 1 Osterville, MA MLS# 22605407 - Image 5

1112 Main Street STE 1 Osterville, MA MLS# 22605407 - Image 6

1112 Main Street STE 1 Osterville, MA MLS# 22605407 - Image 7

1112 Main Street STE 1 Osterville, MA MLS# 22605407 - Image 8

1112 Main Street STE 1 Osterville, MA MLS# 22605407 - Image 9

1112 Main Street STE 1 Osterville, MA MLS# 22605407 - Image 10

Recently Listed

1 of 10

$450,000

2,016

Sq.Ft.

1112 Main Street STE 1

Osterville, MA

15 South Street Osterville, MA MLS# 22605281 - Image 2

15 South Street Osterville, MA MLS# 22605281 - Image 3

15 South Street Osterville, MA MLS# 22605281 - Image 4

15 South Street Osterville, MA MLS# 22605281 - Image 5

15 South Street Osterville, MA MLS# 22605281 - Image 6

15 South Street Osterville, MA MLS# 22605281 - Image 7

15 South Street Osterville, MA MLS# 22605281 - Image 8

15 South Street Osterville, MA MLS# 22605281 - Image 9

15 South Street Osterville, MA MLS# 22605281 - Image 10

15 South Street Osterville, MA MLS# 22605281 - Image 11

15 South Street Osterville, MA MLS# 22605281 - Image 12

15 South Street Osterville, MA MLS# 22605281 - Image 13

15 South Street Osterville, MA MLS# 22605281 - Image 14

15 South Street Osterville, MA MLS# 22605281 - Image 15

15 South Street Osterville, MA MLS# 22605281 - Image 16

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15 South Street Osterville, MA MLS# 22605281 - Image 18

15 South Street Osterville, MA MLS# 22605281 - Image 19

15 South Street Osterville, MA MLS# 22605281 - Image 20

15 South Street Osterville, MA MLS# 22605281 - Image 21

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15 South Street Osterville, MA MLS# 22605281 - Image 24

15 South Street Osterville, MA MLS# 22605281 - Image 25

15 South Street Osterville, MA MLS# 22605281 - Image 26

15 South Street Osterville, MA MLS# 22605281 - Image 27

15 South Street Osterville, MA MLS# 22605281 - Image 28

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15 South Street Osterville, MA MLS# 22605281 - Image 30

15 South Street Osterville, MA MLS# 22605281 - Image 31

15 South Street Osterville, MA MLS# 22605281 - Image 32

15 South Street Osterville, MA MLS# 22605281 - Image 33

15 South Street Osterville, MA MLS# 22605281 - Image 34

Recently Listed

1 of 34

OPEN HOUSE: Saturday 10/31 11:00 AM - 2:00 PM

$775,000

Beds

2.0

Baths

1,170

Sq.Ft.

15 South Street

Osterville, MA

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 2

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 3

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 4

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 5

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 6

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 7

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 8

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 9

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 10

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 11

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 12

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 13

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 14

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 15

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 16

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 17

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 18

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 19

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 20

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 21

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 22

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 23

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 24

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 25

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 26

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 27

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 28

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 29

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 30

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 31

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 32

3040 Falmouth Road APT G3 Osterville, MA MLS# 22605245 - Image 33

Recently Listed

1 of 33

$299,900

Beds

1.0

Baths

412

Sq.Ft.

3040 Falmouth Road APT G3

Osterville, MA

THE TIME TO SELL IS NOW!

13 South Street Osterville, MA MLS# 22605144 - Image 1

13 South Street Osterville, MA MLS# 22605144 - Image 2

13 South Street Osterville, MA MLS# 22605144 - Image 3

13 South Street Osterville, MA MLS# 22605144 - Image 4

13 South Street Osterville, MA MLS# 22605144 - Image 5

13 South Street Osterville, MA MLS# 22605144 - Image 6

13 South Street Osterville, MA MLS# 22605144 - Image 7

13 South Street Osterville, MA MLS# 22605144 - Image 8

13 South Street Osterville, MA MLS# 22605144 - Image 9

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13 South Street Osterville, MA MLS# 22605144 - Image 11

13 South Street Osterville, MA MLS# 22605144 - Image 12

13 South Street Osterville, MA MLS# 22605144 - Image 13

13 South Street Osterville, MA MLS# 22605144 - Image 14

13 South Street Osterville, MA MLS# 22605144 - Image 15

13 South Street Osterville, MA MLS# 22605144 - Image 16

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13 South Street Osterville, MA MLS# 22605144 - Image 18

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13 South Street Osterville, MA MLS# 22605144 - Image 20

13 South Street Osterville, MA MLS# 22605144 - Image 21

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13 South Street Osterville, MA MLS# 22605144 - Image 25

13 South Street Osterville, MA MLS# 22605144 - Image 26

13 South Street Osterville, MA MLS# 22605144 - Image 27

13 South Street Osterville, MA MLS# 22605144 - Image 28

13 South Street Osterville, MA MLS# 22605144 - Image 29

13 South Street Osterville, MA MLS# 22605144 - Image 30

13 South Street Osterville, MA MLS# 22605144 - Image 31

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13 South Street Osterville, MA MLS# 22605144 - Image 33

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13 South Street Osterville, MA MLS# 22605144 - Image 35

13 South Street Osterville, MA MLS# 22605144 - Image 36

13 South Street Osterville, MA MLS# 22605144 - Image 37

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13 South Street Osterville, MA MLS# 22605144 - Image 39

13 South Street Osterville, MA MLS# 22605144 - Image 40

13 South Street Osterville, MA MLS# 22605144 - Image 41

13 South Street Osterville, MA MLS# 22605144 - Image 42

13 South Street Osterville, MA MLS# 22605144 - Image 43

1 of 43

OPEN HOUSE: Saturday 10/31 11:00 AM - 2:00 PM

$795,000

Beds

1.1

Baths

1,170

Sq.Ft.

13 South Street

Osterville, MA

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 2

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 3

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 4

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 5

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 6

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 7

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 8

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 9

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 10

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 11

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 12

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 13

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 14

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 15

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 16

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 17

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 18

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 19

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 20

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 21

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 22

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 23

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 24

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 25

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 26

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 27

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 28

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 29

39 Tower Hill Road BLDG 1 UNIT 1A Osterville, MA MLS# 22604652 - Image 30

1 of 30

$685,000

Beds

2.0

Baths

1,159

Sq.Ft.

39 Tower Hill Road BLDG 1 UNIT 1A

Osterville, MA

111 Westwind Circle Osterville, MA MLS# 22604019 - Image 2

111 Westwind Circle Osterville, MA MLS# 22604019 - Image 3

111 Westwind Circle Osterville, MA MLS# 22604019 - Image 4

111 Westwind Circle Osterville, MA MLS# 22604019 - Image 5

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111 Westwind Circle Osterville, MA MLS# 22604019 - Image 8

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111 Westwind Circle Osterville, MA MLS# 22604019 - Image 11

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111 Westwind Circle Osterville, MA MLS# 22604019 - Image 16

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111 Westwind Circle Osterville, MA MLS# 22604019 - Image 31

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111 Westwind Circle Osterville, MA MLS# 22604019 - Image 35

111 Westwind Circle Osterville, MA MLS# 22604019 - Image 36

111 Westwind Circle Osterville, MA MLS# 22604019 - Image 37

1 of 37

$795,000

Beds

2.0

Baths

1,248

Sq.Ft.

111 Westwind Circle

Osterville, MA

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 2

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 3

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 4

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 5

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 6

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 7

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 8

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 9

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177 Bayview Circle Osterville, MA MLS# 22603520 - Image 11

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 12

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 13

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 14

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177 Bayview Circle Osterville, MA MLS# 22603520 - Image 16

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 17

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177 Bayview Circle Osterville, MA MLS# 22603520 - Image 31

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177 Bayview Circle Osterville, MA MLS# 22603520 - Image 35

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 36

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 37

177 Bayview Circle Osterville, MA MLS# 22603520 - Image 38

1 of 38

$799,900

Beds

2.1

Baths

2,100

Sq.Ft.

177 Bayview Circle

Osterville, MA

295 Westwind Circle Osterville, MA MLS# 22603216 - Image 2

295 Westwind Circle Osterville, MA MLS# 22603216 - Image 3

295 Westwind Circle Osterville, MA MLS# 22603216 - Image 4

295 Westwind Circle Osterville, MA MLS# 22603216 - Image 5

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295 Westwind Circle Osterville, MA MLS# 22603216 - Image 7

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295 Westwind Circle Osterville, MA MLS# 22603216 - Image 11

295 Westwind Circle Osterville, MA MLS# 22603216 - Image 12

295 Westwind Circle Osterville, MA MLS# 22603216 - Image 13

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295 Westwind Circle Osterville, MA MLS# 22603216 - Image 16

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295 Westwind Circle Osterville, MA MLS# 22603216 - Image 29

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295 Westwind Circle Osterville, MA MLS# 22603216 - Image 31

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295 Westwind Circle Osterville, MA MLS# 22603216 - Image 33

295 Westwind Circle Osterville, MA MLS# 22603216 - Image 34

295 Westwind Circle Osterville, MA MLS# 22603216 - Image 35

295 Westwind Circle Osterville, MA MLS# 22603216 - Image 36

295 Westwind Circle Osterville, MA MLS# 22603216 - Image 37

1 of 37

$649,000

Beds

2.0

Baths

1,808

Sq.Ft.

295 Westwind Circle

Osterville, MA

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 2

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 3

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 4

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 5

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 6

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 7

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 8

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 9

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 10

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 11

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 12

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 13

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 14

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 15

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 16

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 17

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 18

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 19

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114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 21

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114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 23

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 24

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114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 26

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 27

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 28

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 29

114 King Arthur Drive Osterville, MA MLS# 22602806 - Image 30

1 of 30

$724,000

Beds

2.0

Baths

1,426

Sq.Ft.

114 King Arthur Drive

Osterville, MA

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 2

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 3

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 4

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 5

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 6

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 7

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727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 11

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 12

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 13

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727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 35

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727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 37

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 38

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 39

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 40

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 41

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 42

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 43

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 44

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 45

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 46

1 of 46

$589,900

Beds

1.1

Baths

1,088

Sq.Ft.

727 Main Street APT B1

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

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

55 Seth Goodspeed Way Osterville, MA MLS# 22601981 - Image 49

1 of 49

$629,900

Beds

2.0

Baths

1,040

Sq.Ft.

55 Seth Goodspeed Way

Osterville, MA

1 of 1

$85,000

120

Sq.Ft.

920A Main Street UNIT 14

Osterville, MA

About Osterville

Listings in Osterville, MA: 58
Estimated median home price: $2,887,500

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	1
$300K - 400K	0
$400K - 500K	1
$500K - 600K	1
$600K - 700K	3
$700K - 800K	5
$800K - 900K	2
$900K - 1M	4
$1M - Max	40

Homes for Sale by Type in Osterville, MA

Property Type	Count
Single Family	44
Townhouse	0
Condo	6
Commercial	4
Rental	0
Lots and Land	4
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 10/29/2026)

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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 10/30/2026. All properties are subject to prior sale, changes, or withdrawal.

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Osterville Massachusetts Homes for Sale

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Osterville Massachusetts Homes for Sale

About Osterville

Listings in Osterville, MA

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Homes for Sale by Price in Osterville, MA

Homes for Sale by Type in Osterville, MA

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