77

Recently Sold Osterville Homes

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  • /4

    $10,500,000

    Sold Dec 16, 2025

    391 Sea View Ave, Osterville, MA 02655

    • 6 Beds
    • 7 Baths
    • 6,830 Sq Ft
    • Built 2020

    Last Sold Summary

    • 30% Below List Price
    • $1,537/SF
    • 134 Days On Market

    Last Listing Agent Gene Orloff Sotheby's International Realty

    391 Sea View Ave, Osterville, MA 02655
  • /37

    $810,000

    Sold Jun 24, 2025

    106 Hickory Hill Cir, Osterville, MA 02655

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • Built 1971

    Last Sold Summary

    • 1% Above List Price
    • $491/SF
    • 5 Days On Market

    Current Estimated Value $804,373

    Last Listing Agent Eileen Prisco Prisco's Five Star Real Estate

    106 Hickory Hill Cir, Osterville, MA 02655
  • /26

    $625,000

    Sold Apr 30, 2026

    369 Bumps River Rd, Osterville, MA 02655

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1984

    Last Sold Summary

    • 11% Below List Price
    • $543/SF
    • 164 Days On Market

    Current Estimated Value $638,467

    Last Listing Agent Eric Dufault Keller Williams Realty

    369 Bumps River Rd, Osterville, MA 02655
  • /7

    $410,000

    Sold Dec 08, 2025

    39 Tower Hill Rd Unit 15B, Osterville, MA 02655

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Built 1979

    Last Sold Summary

    • 9% Below List Price
    • $325/SF
    • 4 Days On Market

    Current Estimated Value $681,547

    Last Listing Agent Witter & Witter Boston/Cape Cod Compass

    39 Tower Hill Rd Unit 15B, Osterville, MA 02655
  • /38

    $2,500,000

    Sold Jul 02, 2025

    47 Great Bay Rd, Osterville, MA 02655

    • 3 Beds
    • 3 Baths
    • 1,960 Sq Ft
    • Built 1950

    Last Sold Summary

    • 4% Above List Price
    • $1,276/SF
    • 10 Days On Market

    Current Estimated Value $2,420,169

    Last Listing Agent Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    47 Great Bay Rd, Osterville, MA 02655
  • /2

    $540,000

    Sold Apr 15, 2026

    31 Galahad Cir, Osterville, MA 02655

    • 3 Beds
    • 3 Baths
    • 1,940 Sq Ft
    • Built 1978

    Last Sold Summary

    • 10% Below List Price
    • $278/SF
    • 13 Days On Market

    Current Estimated Value $601,421

    Last Listing Agent Tanya Chadwick Today Real Estate

    31 Galahad Cir, Osterville, MA 02655
  • /42

    $4,400,000

    Sold Oct 31, 2025

    38 Beach Plum Hill Rd, Osterville, MA 02655

    • 5 Beds
    • 4.5 Baths
    • 3,802 Sq Ft
    • Built 1985

    Last Sold Summary

    • 27% Below List Price
    • $1,157/SF
    • 231 Days On Market

    Current Estimated Value $4,251,660

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    38 Beach Plum Hill Rd, Osterville, MA 02655
  • /14

    $1,570,000

    Sold Apr 14, 2026

    117 Parsley Ln, Osterville, MA 02655

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft
    • Built 1970

    Last Sold Summary

    • 7% Below List Price
    • $839/SF
    • 51 Days On Market

    Current Estimated Value $1,561,041

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

    117 Parsley Ln, Osterville, MA 02655
  • /76

    $2,210,000

    Sold Oct 08, 2025

    162 Starboard Ln, Osterville, MA 02655

    • 4 Beds
    • 3.5 Baths
    • 3,510 Sq Ft
    • Built 1971

    Last Sold Summary

    • 37% Below List Price
    • $630/SF
    • 390 Days On Market

    Current Estimated Value $2,506,036

    Last Listing Agent Michelle Tucker William Raveis Real Estate & Home Services

    162 Starboard Ln, Osterville, MA 02655
  • /32

    $1,165,000

    Sold Sep 15, 2025

    50 Deerfield Rd, Osterville, MA 02655

    • 4 Beds
    • 3 Baths
    • 2,098 Sq Ft
    • Built 1972

    Last Sold Summary

    • 7% Below List Price
    • $555/SF
    • 110 Days On Market

    Current Estimated Value $1,165,139

    Last Listing Agent Joan Witter Compass Massachusetts, LLC

    50 Deerfield Rd, Osterville, MA 02655
  • /34

    $1,220,000

    Sold Sep 03, 2025

    120 Robbins St, Osterville, MA 02655

    • 3 Beds
    • 3.5 Baths
    • 3,226 Sq Ft
    • Built 1989

    Last Sold Summary

    • 18% Below List Price
    • $378/SF
    • 164 Days On Market

    Current Estimated Value $1,221,272

    Last Listing Agent Joan Witter Compass Massachusetts, LLC

    120 Robbins St, Osterville, MA 02655
  • /49

    $1,492,500

    Sold Mar 18, 2026

    29 Oak Ridge Rd, Osterville, MA 02655

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 1990

    Last Sold Summary

    • 6% Below List Price
    • $574/SF
    • 4 Days On Market

    Current Estimated Value $1,562,714

    Last Listing Agent James Murphy, Jr Murphy Real Estate

    29 Oak Ridge Rd, Osterville, MA 02655
  • /40

    $2,700,000

    Sold May 14, 2026

    18 Winfield Way, Osterville, MA 02655

    • 3 Beds
    • 3 Baths
    • 3,055 Sq Ft
    • Built 1953

    Last Sold Summary

    • 10% Below List Price
    • $884/SF
    • 7 Days On Market

    Current Estimated Value $2,964,802

    Last Listing Agent Nicole Callahan Silverstone Capeside Realty Group

    18 Winfield Way, Osterville, MA 02655
  • /26

    $665,000

    Sold Mar 06, 2026

    30 Pond St, Osterville, MA 02655

    • 3 Beds
    • 1 Bath
    • 974 Sq Ft
    • Built 1900

    Last Sold Summary

    • 1% Below List Price
    • $683/SF
    • 15 Days On Market

    Current Estimated Value $680,874

    Last Listing Agent Aidas Kupcinskas Foran Realty, Inc.

    30 Pond St, Osterville, MA 02655
  • /57

    $1,075,000

    Sold Mar 16, 2026

    89 Swift Ave, Osterville, MA 02655

    • 4 Beds
    • 2 Baths
    • 2,674 Sq Ft
    • Built 1970

    Last Sold Summary

    • 10% Below List Price
    • $402/SF
    • 204 Days On Market

    Current Estimated Value $1,142,637

    Last Listing Agent Laurie Jacobson eXp Realty, LLC

    89 Swift Ave, Osterville, MA 02655
  • /40

    $2,900,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,015 Sq Ft

    21 Cockachoisett Ln, Osterville, MA 02655

    A custom home in the quaint seaside Village of Osterville! Perfectly nestled alongside Crosby Boat Yard, Nauticus Marina, Oyster Harbors Marina, The Chart Room and well-known West Bay, you will find this top of line crafted 4 bedroom, 3.5 bathroom home. Hand-selected flooring and natural lighting fill the open-concept entertaining spaces and private rooms, creating an elevated living experience.

    Cynthia Houlihan Berkshire Hathaway HomeServices Robert Paul Properties

    21 Cockachoisett Ln, Osterville, MA 02655
  • /21

    $3,200,000

    Sold May 14, 2026

    125 Wianno Cir, Osterville, MA 02655

    • 4 Beds
    • 4.5 Baths
    • 2,752 Sq Ft
    • Built 2019

    Last Sold Summary

    • 3% Above List Price
    • $1,163/SF
    • 1 Day On Market

    Current Estimated Value $3,058,935

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

    125 Wianno Cir, Osterville, MA 02655
  • /24

    $3,400,000

    Sold Oct 03, 2025

    780 Sea View Ave, Osterville, MA 02655

    • 4 Beds
    • 5 Baths
    • 5,460 Sq Ft
    • Built 1987

    Last Sold Summary

    • 3% Below List Price
    • $623/SF
    • 1 Day On Market

    Current Estimated Value $3,523,741

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

    780 Sea View Ave, Osterville, MA 02655
  • /12

    $2,550,000

    Sold Dec 04, 2025

    64 Bay St, Osterville, MA 02655

    • 4 Beds
    • 5 Baths
    • 2,812 Sq Ft
    • Built 2002

    Last Sold Summary

    • 27% Below List Price
    • $907/SF
    • 78 Days On Market

    Current Estimated Value $2,508,197

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    64 Bay St, Osterville, MA 02655
  • /28

    $850,000

    Sold May 07, 2026

    64 Falling Leaf Ln, Osterville, MA 02655

    • 2 Beds
    • 2 Baths
    • 1,667 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Above List Price
    • $510/SF
    • 7 Days On Market

    Current Estimated Value $835,435

    Last Listing Agent Maggie Fearn Sotheby's International Realty

    64 Falling Leaf Ln, Osterville, MA 02655
  • /88

    $2,487,500

    Sold Apr 16, 2026

    98 Bunker Hill Rd, Osterville, MA 02655

    • 5 Beds
    • 4.5 Baths
    • 4,715 Sq Ft
    • Built 1978

    Last Sold Summary

    • 14% Below List Price
    • $528/SF
    • 377 Days On Market

    Current Estimated Value $2,720,795

    Last Listing Agent Shaelyn Hegarty Frank A Sullivan Real Estate

    98 Bunker Hill Rd, Osterville, MA 02655
  • /27

    $3,000,000

    Sold Nov 06, 2025

    355 Bridge St, Osterville, MA 02655

    • 4 Beds
    • 3.5 Baths
    • 3,720 Sq Ft
    • Built 1998

    Last Sold Summary

    • 3% Below List Price
    • $806/SF
    • 1 Day On Market

    Current Estimated Value $3,161,583

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

    355 Bridge St, Osterville, MA 02655
  • /53

    $2,000,000

    Sold Mar 31, 2026

    67 Fire Station Rd, Osterville, MA 02655

    • 4 Beds
    • 4 Baths
    • 2,999 Sq Ft
    • Built 2020

    Last Sold Summary

    • 3% Above List Price
    • $667/SF
    • 4 Days On Market

    Current Estimated Value $2,000,557

    Last Listing Agent Julie White William Raveis Real Estate & Home Services

    67 Fire Station Rd, Osterville, MA 02655
  • /57

    $4,400,000

    Sold Mar 02, 2026

    405 Bridge St, Osterville, MA 02655

    • 5 Beds
    • 7 Baths
    • 6,768 Sq Ft
    • Built 2000

    Last Sold Summary

    • 3% Below List Price
    • $650/SF
    • 6 Days On Market

    Current Estimated Value $4,486,548

    Last Listing Agent John Cotton Sotheby's International Realty

    405 Bridge St, Osterville, MA 02655
  • /56

    $1,490,000

    Sold May 29, 2026

    92 Wianno Cir, Osterville, MA 02655

    • 3 Beds
    • 3 Baths
    • 2,459 Sq Ft
    • Built 1990

    Last Sold Summary

    • 7% Below List Price
    • $606/SF
    • 4 Days On Market

    Current Estimated Value $1,651,944

    Last Listing Agent Marian Oost-Lievense New Seabury Sotheby's International Realty

    92 Wianno Cir, Osterville, MA 02655
  • /27

    $327,000

    Sold Jan 28, 2026

    3040 Falmouth Rd Unit H, Osterville, MA 02655

    • 2 Beds
    • 1 Bath
    • 594 Sq Ft
    • Built 1925

    Last Sold Summary

    • 8% Below List Price
    • $551/SF
    • 64 Days On Market

    Current Estimated Value $333,542

    Last Listing Agent Livia Freitas Monteforte Compass Massachusetts, LLC

    3040 Falmouth Rd Unit H, Osterville, MA 02655
  • /20

    $650,000

    Sold Jan 27, 2026

    7 Ebenezer, Centerville, MA 02632

    • 3 Beds
    • 4 Baths
    • 2,540 Sq Ft
    • Built 1981

    Last Sold Summary

    • 13% Below List Price
    • $256/SF
    • 114 Days On Market

    Last Listing Agent Bruce Katcher Berkshire Hathaway HomeService Robert Paul Properties

    7 Ebenezer, Centerville, MA 02632
  • /39

    $1,000,000

    Sold Jul 01, 2025

    38 Sunset Ln, Osterville, MA 02655

    • 3 Beds
    • 2 Baths
    • 1,153 Sq Ft
    • Built 1927

    Last Sold Summary

    • 22% Below List Price
    • $867/SF
    • 137 Days On Market

    Current Estimated Value $1,054,205

    Last Listing Agent Colleen Riley Sotheby's International Realty

    38 Sunset Ln, Osterville, MA 02655
  • /70

    $7,500,000

    Sold Jun 15, 2026

    850 Sea View Ave, Osterville, MA 02655

    • 8 Beds
    • 9 Baths
    • 7,350 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Below List Price
    • $1,020/SF
    • 216 Days On Market

    Current Estimated Value $7,623,335

    Last Listing Agent John Cotton Sotheby's International Realty

    850 Sea View Ave, Osterville, MA 02655
  • /21

    $580,000

    Sold Mar 05, 2026

    16 2nd Ave Unit 5A, Osterville, MA 02655

    • 1 Bed
    • 1 Bath
    • 720 Sq Ft
    • Built 1980

    Last Sold Summary

    • 7% Below List Price
    • $806/SF
    • 124 Days On Market

    Current Estimated Value $617,876

    Last Listing Agent Shaelyn Hegarty Frank A Sullivan Real Estate

    16 2nd Ave Unit 5A, Osterville, MA 02655
  • /34

    $1,025,000

    Sold Jul 08, 2025

    141 Parsley Ln, Osterville, MA 02655

    • 2 Beds
    • 2 Baths
    • 1,868 Sq Ft
    • Built 1970

    Last Sold Summary

    • 15% Below List Price
    • $549/SF
    • 40 Days On Market

    Current Estimated Value $1,086,520

    Last Listing Agent Julie White William Raveis Real Estate & Home Services

    141 Parsley Ln, Osterville, MA 02655
  • /36

    $5,800,000

    Sold Feb 18, 2026

    439 Sea View Ave, Osterville, MA 02655

    • 6 Beds
    • 6 Baths
    • 4,021 Sq Ft
    • Built 1930

    Last Sold Summary

    • 11% Below List Price
    • $1,442/SF
    • 108 Days On Market

    Current Estimated Value $5,772,307

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    439 Sea View Ave, Osterville, MA 02655
  • /26

    $327,000

    Sold Jan 28, 2026

    3040 Falmouth Rd Unit H, Osterville, MA 02655

    • 2 Beds
    • 1 Bath
    • 594 Sq Ft
    • Built 1925

    Last Sold Summary

    • 8% Below List Price
    • $551/SF
    • 64 Days On Market

    Current Estimated Value $333,542

    Last Listing Agent Livia Freitas Monteforte Compass

    3040 Falmouth Rd Unit H, Osterville, MA 02655
  • /7

    $410,000

    Sold Dec 08, 2025

    39 Tower Hill Rd Unit 15B, Osterville, MA 02655

    • 2 Beds
    • 2 Baths
    • 1,261 Sq Ft
    • Built 1979

    Last Sold Summary

    • 9% Below List Price
    • $325/SF
    • 3 Days On Market

    Current Estimated Value $681,547

    Last Listing Agent Joan Witter Compass Massachusetts, LLC

    39 Tower Hill Rd Unit 15B, Osterville, MA 02655
  • /7

    $563,000

    Sold Jun 05, 2026

    39 Tower Hill Rd Unit 1, Osterville, MA 02655

    • 2 Beds
    • 2 Baths
    • 1,159 Sq Ft
    • Built 1972

    Last Sold Summary

    • 10% Below List Price
    • $486/SF
    • 8 Days On Market

    Last Listing Agent Tom Foley The Foley Company

    39 Tower Hill Rd Unit 1, Osterville, MA 02655
  • /22

    $803,000

    Sold Feb 06, 2026

    30 Deerfield Rd, Osterville, MA 02655

    • 3 Beds
    • 2 Baths
    • 1,937 Sq Ft
    • Built 1972

    Last Sold Summary

    • 5% Above List Price
    • $415/SF
    • 53 Days On Market

    Current Estimated Value $847,479

    Last Listing Agent Justin Manning JJManning Auctioneers

    30 Deerfield Rd, Osterville, MA 02655
  • /40

    $950,000

    Sold Jan 27, 2026

    139 Falling Leaf Ln, Osterville, MA 02655

    • 3 Beds
    • 4 Baths
    • 2,162 Sq Ft
    • Built 1999

    Last Sold Summary

    • 5% Below List Price
    • $439/SF
    • 15 Days On Market

    Current Estimated Value $956,895

    Last Listing Agent Linda Whitcomb William Raveis Real Estate & Home Services

    139 Falling Leaf Ln, Osterville, MA 02655

Showing Results 41 - 77, Page 2 of 2

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