3,950

Osterville Homes

Section Image
    • 727 Main St Unit B2, Osterville, MA 02655
      727 Main St Unit B2, Osterville, MA 02655
      727 Main St Unit B2, Osterville, MA 02655
      /40

      Est $598,926 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,088 Sq Ft

      727 Main St Unit B2, Osterville, MA 02655

      727 Main St Unit B2, Osterville, MA 02655
    • 320 Seapuit River Rd, Barnstable, MA 02655
      320 Seapuit River Rd, Barnstable, MA 02655
      320 Seapuit River Rd, Barnstable, MA 02655
      /46

      Est $4,598,065 Not Listed For Sale

      • 6 Beds
      • 7 Baths
      • 5,478 Sq Ft

      320 Seapuit River Rd, Barnstable, MA 02655

      320 Seapuit River Rd, Barnstable, MA 02655
    • 39 Tower Hill Rd, Osterville, MA 02655
      39 Tower Hill Rd, Osterville, MA 02655
      39 Tower Hill Rd, Osterville, MA 02655
      /26

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,278 Sq Ft

      39 Tower Hill Rd, Osterville, MA 02655

      39 Tower Hill Rd, Osterville, MA 02655
    • 727 Main St Unit 5G, Osterville, MA 02655
      727 Main St Unit 5G, Osterville, MA 02655
      727 Main St Unit 5G, Osterville, MA 02655
      /29

      Est $590,878 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 997 Sq Ft

      727 Main St Unit 5G, Osterville, MA 02655

      727 Main St Unit 5G, Osterville, MA 02655
    • 416 Osterville West Barnstable Rd, Barnstable, MA 02655
      416 Osterville West Barnstable Rd, Barnstable, MA 02655
      416 Osterville West Barnstable Rd, Barnstable, MA 02655
      /27

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 693 Sq Ft

      416 Osterville West Barnstable Rd, Barnstable, MA 02655

      416 Osterville West Barnstable Rd, Barnstable, MA 02655
    • 7 Bonnie Briar Dr, Barnstable, MA 02655
      7 Bonnie Briar Dr, Barnstable, MA 02655
      7 Bonnie Briar Dr, Barnstable, MA 02655
      /17

      Est $647,354 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,144 Sq Ft

      7 Bonnie Briar Dr, Barnstable, MA 02655

      7 Bonnie Briar Dr, Barnstable, MA 02655
    • 79 Sand Point Rd, Barnstable, MA 02655
      79 Sand Point Rd, Barnstable, MA 02655
      79 Sand Point Rd, Barnstable, MA 02655
      /32

      Est $7,992,317 Not Listed For Sale

      • 6 Beds
      • 5.5 Baths
      • 4,944 Sq Ft

      79 Sand Point Rd, Barnstable, MA 02655

      79 Sand Point Rd, Barnstable, MA 02655
    • 79 Sand Point, Barnstable, MA 02635
      79 Sand Point, Barnstable, MA 02635
      79 Sand Point, Barnstable, MA 02635
      /92

      Not Listed For Sale

      • 6 Beds
      • 5.5 Baths
      • 4,944 Sq Ft

      79 Sand Point, Barnstable, MA 02635

      79 Sand Point, Barnstable, MA 02635
    • 106 Wianno, Barnstable, MA 02655
      106 Wianno, Barnstable, MA 02655
      106 Wianno, Barnstable, MA 02655
      /30

      Est $2,004,790 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,702 Sq Ft

      106 Wianno, Barnstable, MA 02655

      106 Wianno, Barnstable, MA 02655
    • 20 Flowing Pond Cir, Osterville, MA 02655
      20 Flowing Pond Cir, Osterville, MA 02655
      20 Flowing Pond Cir, Osterville, MA 02655
      /45

      Est $622,897 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,346 Sq Ft

      20 Flowing Pond Cir, Osterville, MA 02655

      20 Flowing Pond Cir, Osterville, MA 02655
    • 345 Windswept Way, Osterville, MA 02655
      345 Windswept Way, Osterville, MA 02655
      345 Windswept Way, Osterville, MA 02655
      /66

      Est $7,014,571 Not Listed For Sale

      • 5 Beds
      • 8 Baths
      • 6,104 Sq Ft

      345 Windswept Way, Osterville, MA 02655

      345 Windswept Way, Osterville, MA 02655
    • 290 N Bay Rd, Barnstable, MA 02655
      290 N Bay Rd, Barnstable, MA 02655
      290 N Bay Rd, Barnstable, MA 02655
      /38

      Est $6,034,047 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 4,099 Sq Ft

      290 N Bay Rd, Barnstable, MA 02655

      290 N Bay Rd, Barnstable, MA 02655
    • 416 Osterville West Barnstable Rd, Marstons Mills, MA 02648
      416 Osterville West Barnstable Rd, Marstons Mills, MA 02648
      416 Osterville West Barnstable Rd, Marstons Mills, MA 02648
      /27

      Est $458,996 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 693 Sq Ft

      416 Osterville West Barnstable Rd, Marstons Mills, MA 02648

      416 Osterville West Barnstable Rd, Marstons Mills, MA 02648
    • 34 & 52 Caillouet Ln, Barnstable, MA 02655
      34 & 52 Caillouet Ln, Barnstable, MA 02655
      34 & 52 Caillouet Ln, Barnstable, MA 02655
      /51

      Est $6,831,562 Not Listed For Sale

      • 8 Beds
      • 9 Baths
      • 8,230 Sq Ft

      34 & 52 Caillouet Ln, Barnstable, MA 02655

      34 & 52 Caillouet Ln, Barnstable, MA 02655
    • 186 Windswept Way, Barnstable, MA 02655
      186 Windswept Way, Barnstable, MA 02655
      186 Windswept Way, Barnstable, MA 02655
      /42

      Not Listed For Sale

      • 8 Beds
      • 8 Baths
      • 10,063 Sq Ft

      186 Windswept Way, Barnstable, MA 02655

      186 Windswept Way, Barnstable, MA 02655
    • 292 Grand Island Dr, Barnstable, MA 02655
      292 Grand Island Dr, Barnstable, MA 02655
      292 Grand Island Dr, Barnstable, MA 02655
      /36

      Est $3,780,706 Not Listed For Sale

      • 5 Beds
      • 5.5 Baths
      • 4,707 Sq Ft

      292 Grand Island Dr, Barnstable, MA 02655

      292 Grand Island Dr, Barnstable, MA 02655
    • 292 Grand Island Dr, Osterville, MA 2655
      292 Grand Island Dr, Osterville, MA 2655
      292 Grand Island Dr, Osterville, MA 2655
      /41

      Est $3,780,706 Not Listed For Sale

      • 6 Beds
      • 5.5 Baths
      • 4,707 Sq Ft

      292 Grand Island Dr, Osterville, MA 2655

      292 Grand Island Dr, Osterville, MA 2655
    • 99 Stone Horse Rd, Osterville, MA 2655
      99 Stone Horse Rd, Osterville, MA 2655
      99 Stone Horse Rd, Osterville, MA 2655
      /6

      Est $2,282,636 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,812 Sq Ft

      99 Stone Horse Rd, Osterville, MA 2655

      99 Stone Horse Rd, Osterville, MA 2655
    • 39 Fox Island Rd, Osterville, MA 2655
      39 Fox Island Rd, Osterville, MA 2655
      39 Fox Island Rd, Osterville, MA 2655
      /11

      Est $2,018,461 Not Listed For Sale

      • 2 Beds

      39 Fox Island Rd, Osterville, MA 2655

      39 Fox Island Rd, Osterville, MA 2655
    • 21 Darby Way, Osterville, MA 2655
      21 Darby Way, Osterville, MA 2655
      21 Darby Way, Osterville, MA 2655
      /33

      Est $1,368,296 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,098 Sq Ft

      21 Darby Way, Osterville, MA 2655

      21 Darby Way, Osterville, MA 2655
    • 290 N Bay Rd, Osterville, MA 2655
      290 N Bay Rd, Osterville, MA 2655
      290 N Bay Rd, Osterville, MA 2655
      /39

      Est $6,034,047 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 4,099 Sq Ft

      290 N Bay Rd, Osterville, MA 2655

      290 N Bay Rd, Osterville, MA 2655
    • 186 Windswept Way, Osterville, MA 2655
      186 Windswept Way, Osterville, MA 2655
      186 Windswept Way, Osterville, MA 2655
      /87

      Not Listed For Sale

      • 8 Beds
      • 8 Baths
      • 10,063 Sq Ft

      186 Windswept Way, Osterville, MA 2655

      186 Windswept Way, Osterville, MA 2655
    • 106 Wianno Ave, Osterville, MA 2655
      106 Wianno Ave, Osterville, MA 2655
      106 Wianno Ave, Osterville, MA 2655
      /36

      Est $2,004,790 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,702 Sq Ft

      106 Wianno Ave, Osterville, MA 2655

      106 Wianno Ave, Osterville, MA 2655
    • 350 Windswept Way, Barnstable, MA 02655
      350 Windswept Way, Barnstable, MA 02655
      350 Windswept Way, Barnstable, MA 02655
      /32

      Est $5,787,567 Not Listed For Sale

      • 5 Beds
      • 5.5 Baths
      • 5,924 Sq Ft

      350 Windswept Way, Barnstable, MA 02655

      350 Windswept Way, Barnstable, MA 02655
    • 49 4th Ave, Barnstable, MA 02655
      49 4th Ave, Barnstable, MA 02655
      49 4th Ave, Barnstable, MA 02655
      /40

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 750 Sq Ft

      49 4th Ave, Barnstable, MA 02655

      49 4th Ave, Barnstable, MA 02655
    • 81 & 73 Oyster Way, Barnstable, MA 02649
      81 & 73 Oyster Way, Barnstable, MA 02649
      81 & 73 Oyster Way, Barnstable, MA 02649
      /32

      Not Listed For Sale

      • 5 Beds
      • 8 Baths
      • 7,205 Sq Ft

      81 & 73 Oyster Way, Barnstable, MA 02649

      81 & 73 Oyster Way, Barnstable, MA 02649
    • 250 Windswept Way, Osterville, MA 02655
      250 Windswept Way, Osterville, MA 02655
      250 Windswept Way, Osterville, MA 02655
      /23

      Est $7,213,524 Not Listed For Sale

      • 6 Beds
      • 5 Baths
      • 4,235 Sq Ft

      250 Windswept Way, Osterville, MA 02655

      250 Windswept Way, Osterville, MA 02655
    • 123 Pineleigh Path, Osterville, MA 02655
      123 Pineleigh Path, Osterville, MA 02655
      123 Pineleigh Path, Osterville, MA 02655
      /23

      Est $4,770,701 Not Listed For Sale

      • 4 Beds
      • 6 Baths
      • 5,287 Sq Ft

      123 Pineleigh Path, Osterville, MA 02655

      123 Pineleigh Path, Osterville, MA 02655
    • 41 Osterville West Barnstable Rd, Osterville, MA 02655
      41 Osterville West Barnstable Rd, Osterville, MA 02655
      41 Osterville West Barnstable Rd, Osterville, MA 02655
      /60

      Est $2,246,451 Not Listed For Sale

      • 4 Beds
      • 6 Baths
      • 3,466 Sq Ft

      41 Osterville West Barnstable Rd, Osterville, MA 02655

      41 Osterville West Barnstable Rd, Osterville, MA 02655
    • 39 Blossom Ave Unit 6, Osterville, MA 02655
      39 Blossom Ave Unit 6, Osterville, MA 02655
      39 Blossom Ave Unit 6, Osterville, MA 02655
      /24

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,188 Sq Ft

      39 Blossom Ave Unit 6, Osterville, MA 02655

      39 Blossom Ave Unit 6, Osterville, MA 02655
    • 44 Osterville West Barnstabl, Barnstable, MA 02655
      44 Osterville West Barnstabl, Barnstable, MA 02655
      44 Osterville West Barnstabl, Barnstable, MA 02655
      /26

      Est $1,264,888 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,238 Sq Ft

      44 Osterville West Barnstabl, Barnstable, MA 02655

      44 Osterville West Barnstabl, Barnstable, MA 02655
    • 20 Grand Island Dr, Barnstable, MA 02655
      20 Grand Island Dr, Barnstable, MA 02655
      20 Grand Island Dr, Barnstable, MA 02655
      /59

      Est $2,178,105 Not Listed For Sale

      • 8 Beds
      • 5 Baths
      • 2,811 Sq Ft

      20 Grand Island Dr, Barnstable, MA 02655

      20 Grand Island Dr, Barnstable, MA 02655
    • 299 Eel River Rd, Osterville, MA 02655
      299 Eel River Rd, Osterville, MA 02655
      299 Eel River Rd, Osterville, MA 02655
      /11

      Est $4,719,735 Not Listed For Sale

      • 6 Beds

      299 Eel River Rd, Osterville, MA 02655

      299 Eel River Rd, Osterville, MA 02655
    • 40 Woodland Ave, Osterville, MA 02655
      40 Woodland Ave, Osterville, MA 02655
      40 Woodland Ave, Osterville, MA 02655
      /36

      Est $2,943,707 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,904 Sq Ft

      40 Woodland Ave, Osterville, MA 02655

      40 Woodland Ave, Osterville, MA 02655
    • 143 Hickory Hill Cir, Osterville, MA 02655
      143 Hickory Hill Cir, Osterville, MA 02655
      143 Hickory Hill Cir, Osterville, MA 02655
      /34

      Est $1,066,012 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,802 Sq Ft

      143 Hickory Hill Cir, Osterville, MA 02655

      143 Hickory Hill Cir, Osterville, MA 02655
    • 195 Seth Goodspeed Way, Osterville, MA 02655
      195 Seth Goodspeed Way, Osterville, MA 02655
      195 Seth Goodspeed Way, Osterville, MA 02655
      /28

      Est $686,966 Not Listed For Sale

      • 2 Beds
      • 3 Baths
      • 1,200 Sq Ft

      195 Seth Goodspeed Way, Osterville, MA 02655

      195 Seth Goodspeed Way, Osterville, MA 02655
    • 94 Starboard Ln, Osterville, MA 02655
      94 Starboard Ln, Osterville, MA 02655
      94 Starboard Ln, Osterville, MA 02655
      /47

      Est $4,453,172 Not Listed For Sale

      • 4 Beds
      • 5.5 Baths
      • 4,575 Sq Ft

      94 Starboard Ln, Osterville, MA 02655

      94 Starboard Ln, Osterville, MA 02655
    • 352 Starboard Ln, Osterville, MA 02655
      352 Starboard Ln, Osterville, MA 02655
      352 Starboard Ln, Osterville, MA 02655
      /42

      Est $3,442,928 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,240 Sq Ft

      352 Starboard Ln, Osterville, MA 02655

      352 Starboard Ln, Osterville, MA 02655
    • 311 Starboard Ln, Osterville, MA 02655
      311 Starboard Ln, Osterville, MA 02655
      311 Starboard Ln, Osterville, MA 02655
      /15

      Est $1,810,798 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,000 Sq Ft

      311 Starboard Ln, Osterville, MA 02655

      311 Starboard Ln, Osterville, MA 02655
    • 10 Deerfield Rd, Osterville, MA 02655
      10 Deerfield Rd, Osterville, MA 02655
      10 Deerfield Rd, Osterville, MA 02655
      /31

      Est $919,075 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,718 Sq Ft

      10 Deerfield Rd, Osterville, MA 02655

      10 Deerfield Rd, Osterville, MA 02655

Showing Results 241 - 280, Page 7 of 18

Massachusetts Barnstable Osterville

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group