Osterville Massachusetts Homes for Sale

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727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 1

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 2

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 3

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 4

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 5

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 6

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 7

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 8

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 9

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 10

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 11

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 12

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 13

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 14

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 15

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 16

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 17

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 18

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 19

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 20

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 21

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 22

727 Main Street UNIT F3 Osterville, MA MLS# 22602373 - Image 23

1 of 23

$689,000

Beds

2.0

Baths

1,198

Sq.Ft.

727 Main Street UNIT F3

Osterville, MA

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 2

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 3

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 4

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 5

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 6

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 7

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 8

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 9

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 10

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 11

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 12

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 13

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 14

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 15

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 16

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 17

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 18

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 19

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 20

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 21

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 22

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 23

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 24

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 25

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 26

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 27

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 28

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 29

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 30

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 31

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 32

105 Parker Road UNIT B Osterville, MA MLS# 22602404 - Image 33

1 of 33

$800,000

Beds

2.1

Baths

1,954

Sq.Ft.

105 Parker Road UNIT B

Osterville, MA

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

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

46 Great Bay Road Osterville, MA MLS# 22602282 - Image 4

46 Great Bay Road Osterville, MA MLS# 22602282 - Image 5

46 Great Bay Road Osterville, MA MLS# 22602282 - Image 6

46 Great Bay Road Osterville, MA MLS# 22602282 - Image 7

46 Great Bay Road Osterville, MA MLS# 22602282 - Image 8

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46 Great Bay Road Osterville, MA MLS# 22602282 - Image 45

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

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46 Great Bay Road Osterville, MA MLS# 22602282 - Image 53

46 Great Bay Road Osterville, MA MLS# 22602282 - Image 54

1 of 54

$8,500,000

Beds

4.2

Baths

4,831

Sq.Ft.

46 Great Bay Road

Osterville, MA

THE TIME TO SELL IS NOW!

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 1

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

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 8

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 9

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 10

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

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 14

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 15

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 16

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 17

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 18

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 19

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 20

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 21

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 22

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 23

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 24

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 25

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 26

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 27

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 28

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 29

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 30

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 31

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 32

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 33

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 34

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

727 Main Street APT B1 Osterville, MA MLS# 22602304 - Image 36

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

$599,900

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 7

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

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

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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

1 of 48

$659,900

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

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

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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

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 41

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

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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

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

1 of 41

$1,950,000

Beds

2.1

Baths

3,084

Sq.Ft.

81 Osterville West Barnstable 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

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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

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162 Main Street Osterville, MA MLS# 22601704 - Image 54

1 of 54

$1,785,000

Beds

2.1

Baths

2,048

Sq.Ft.

162 Main Street

Osterville, MA

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

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

955 Main Street Osterville, MA MLS# 22601611 - Image 4

955 Main Street Osterville, MA MLS# 22601611 - Image 5

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1 of 52

$1,500,000

Beds

2.0

Baths

1,765

Sq.Ft.

955 Main Street

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

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

Virtual Tour

1 of 24

$4,495,000

Beds

4.0

Baths

4,964

Sq.Ft.

93 Oyster Way

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

441 Old Mill Road Osterville, MA MLS# 22601575 - Image 5

441 Old Mill Road Osterville, MA MLS# 22601575 - Image 6

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441 Old Mill Road Osterville, MA MLS# 22601575 - Image 17

1 of 17

$810,000

Beds

2.0

Baths

1,144

Sq.Ft.

441 Old Mill Road

Osterville, MA

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

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

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1 of 42

$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

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1 of 45

$1,199,000

Beds

2.1

Baths

2,190

Sq.Ft.

31 Falling Leaf Lane

Osterville, MA

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

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

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1 of 44

$7,900,000

Beds

6.0

Baths

4,896

Sq.Ft.

255 Bayberry Way

Osterville, MA

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

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

82 Crystal Lake Road Osterville, MA MLS# 22601140 - Image 4

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1 of 64

$3,475,000

Beds

3.2

Baths

4,364

Sq.Ft.

82 Crystal Lake Road

Osterville, MA

5 Briar Patch Road Osterville, MA MLS# 22600998 - Image 2

5 Briar Patch Road Osterville, MA MLS# 22600998 - Image 3

5 Briar Patch Road Osterville, MA MLS# 22600998 - Image 4

5 Briar Patch Road Osterville, MA MLS# 22600998 - Image 5

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5 Briar Patch Road Osterville, MA MLS# 22600998 - Image 29

Virtual Tour

1 of 29

$875,000

Beds

2.0

Baths

1,497

Sq.Ft.

5 Briar Patch Road

Osterville, MA

199 E Bay Road APT 12 Osterville, MA MLS# 22600859 - Image 2

199 E Bay Road APT 12 Osterville, MA MLS# 22600859 - Image 3

199 E Bay Road APT 12 Osterville, MA MLS# 22600859 - Image 4

199 E Bay Road APT 12 Osterville, MA MLS# 22600859 - Image 5

199 E Bay Road APT 12 Osterville, MA MLS# 22600859 - Image 6

199 E Bay Road APT 12 Osterville, MA MLS# 22600859 - Image 7

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199 E Bay Road APT 12 Osterville, MA MLS# 22600859 - Image 11

199 E Bay Road APT 12 Osterville, MA MLS# 22600859 - Image 12

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199 E Bay Road APT 12 Osterville, MA MLS# 22600859 - Image 21

199 E Bay Road APT 12 Osterville, MA MLS# 22600859 - Image 22

199 E Bay Road APT 12 Osterville, MA MLS# 22600859 - Image 23

199 E Bay Road APT 12 Osterville, MA MLS# 22600859 - Image 24

1 of 24

$2,200,000

Beds

3.1

Baths

3,118

Sq.Ft.

199 E Bay Road APT 12

Osterville, MA

414 Eel River Road Osterville, MA MLS# 22600750 - Image 2

414 Eel River Road Osterville, MA MLS# 22600750 - Image 3

414 Eel River Road Osterville, MA MLS# 22600750 - Image 4

414 Eel River Road Osterville, MA MLS# 22600750 - Image 5

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414 Eel River Road Osterville, MA MLS# 22600750 - Image 40

1 of 40

$3,499,999

Beds

7.1

Baths

6,905

Sq.Ft.

414 Eel River Road

Osterville, MA

About Osterville

Listings in Osterville, MA: 60
Estimated median home price: $2,225,000

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

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$100K - 200K	0
$200K - 300K	0
$300K - 400K	0
$400K - 500K	0
$500K - 600K	2
$600K - 700K	6
$700K - 800K	2
$800K - 900K	5
$900K - 1M	1
$1M - Max	43

Homes for Sale by Type in Osterville, MA

Property Type	Count
Single Family	49
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 6/29/2026)

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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 7/1/2026. All properties are subject to prior sale, changes, or withdrawal.

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