67

Recently Sold Osterville Homes

Section Image
  • /40

    $1,030,000

    Sold Dec 15, 2025

    25 Sturbridge Dr, Osterville, MA 02655

    • 3 Beds
    • 2.5 Baths
    • 2,227 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $463/SF
    • 13 Days On Market

    Current Estimated Value $1,125,271

    Last Listing Agent virginia guimond William Raveis R.E. & Home Services

    25 Sturbridge Dr, Osterville, MA 02655
  • /2

    $540,000

    Sold Apr 15, 2026

    31 Galahad Cir, Osterville, MA 02655

    • 4 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 $577,458

    Last Listing Agent Tanya Chadwick Today Real Estate, Inc.

    31 Galahad Cir, Osterville, MA 02655
  • /18

    $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 $3,084,246

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

    125 Wianno Cir, Osterville, MA 02655
  • /20

    $545,000

    Sold Dec 11, 2025

    39 Tower Hill Rd Unit 1C, Osterville, MA 02655

    • 2 Beds
    • 2 Baths
    • 1,131 Sq Ft
    • Built 1972

    Last Sold Summary

    • 6% Below List Price
    • $482/SF
    • 98 Days On Market

    Current Estimated Value $575,499

    Last Listing Agent Ed Chatelain Chatelain Real Estate

    39 Tower Hill Rd Unit 1C, Osterville, MA 02655
  • /40

    $1,495,000

    Sold Jul 29, 2026

    25 Manor Way, Osterville, MA 02655

    • 4 Beds
    • 4 Baths
    • 2,509 Sq Ft
    • Built 1972

    Last Sold Summary

    • 4% Below List Price
    • $596/SF
    • 5 Days On Market

    Current Estimated Value $1,752,955

    Last Listing Agent Peter Vaillancout EXIT Cape Realty

    25 Manor Way, Osterville, MA 02655
  • /40

    $2,700,000

    Sold Jun 18, 2026

    21 Cockachoiset Ln, Barnstable, MA 02655

    • 4 Beds
    • 3.5 Baths
    • 3,015 Sq Ft
    • Built 2022

    Last Sold Summary

    • 7% Below List Price
    • $896/SF
    • 23 Days On Market

    Current Estimated Value $2,870,568

    Last Listing Agent Cynthia Houlihan Berkshire Hathaway HomeServices Robert Paul Properties

    21 Cockachoiset Ln, Barnstable, MA 02655
  • /42

    $2,210,000

    Sold Oct 08, 2025

    162 Starboard Ln, Osterville, MA 02655

    • 4 Beds
    • 3.5 Baths
    • 2,710 Sq Ft
    • Built 1971

    Last Sold Summary

    • 37% Below List Price
    • $815/SF
    • 389 Days On Market

    Current Estimated Value $2,557,336

    Last Listing Agent Michelle Tucker William Raveis R.E. & Home Services

    162 Starboard Ln, Osterville, MA 02655
  • /42

    $4,200,000

    Sold Aug 08, 2025

    281 Wianno Ave, Osterville, MA 02655

    • 7 Beds
    • 5.5 Baths
    • 4,375 Sq Ft
    • Built 1890

    Last Sold Summary

    • 10% Below List Price
    • $960/SF
    • 16 Days On Market

    Current Estimated Value $4,435,511

    Last Listing Agent John Hopkins Frank Sullivan Real Estate, LLC

    281 Wianno Ave, Osterville, MA 02655
  • /42

    $5,600,000

    Sold Sep 02, 2025

    195 Bunker Hill Rd, Osterville, MA 02655

    • 6 Beds
    • 7.5 Baths
    • 6,565 Sq Ft
    • Built 2011

    Last Sold Summary

    • 6% Below List Price
    • $853/SF
    • 16 Days On Market

    Current Estimated Value $5,685,927

    Last Listing Agent John Cotton Sotheby's International Realty

    195 Bunker Hill Rd, Osterville, MA 02655
  • /40

    $7,800,000

    Sold Jul 29, 2026

    255 Bayberry Way, Osterville, MA 02655

    • 7 Beds
    • 6 Baths
    • 4,896 Sq Ft
    • Built 1988

    Last Sold Summary

    • 1% Below List Price
    • $1,593/SF
    • 105 Days On Market

    Current Estimated Value $8,422,518

    Last Listing Agent Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    255 Bayberry Way, Osterville, MA 02655
  • /40

    $2,700,000

    Sold Jun 18, 2026

    21 Cockachoisett Ln, Osterville, MA 02655

    • 4 Beds
    • 3.5 Baths
    • 3,015 Sq Ft
    • Built 2021

    Last Sold Summary

    • 7% Below List Price
    • $896/SF
    • 23 Days On Market

    Current Estimated Value $2,794,337

    Last Listing Agent Cynthia Houlihan Berkshire Hathaway HomeServices Robert Paul Properties

    21 Cockachoisett Ln, Osterville, MA 02655
  • /17

    $655,000

    Sold Dec 19, 2025

    435 Old Mill Rd, Osterville, MA 02655

    • 3 Beds
    • 2 Baths
    • 1,660 Sq Ft
    • Built 1973

    Last Sold Summary

    • 8% Below List Price
    • $395/SF
    • 6 Days On Market

    Current Estimated Value $708,454

    Last Listing Agent Gerald Mullen NextHome Signature Realty

    435 Old Mill Rd, Osterville, MA 02655
  • /23

    $2,000,000

    Sold Jul 13, 2026

    51 Wianno Cir, Osterville, MA 02655

    • 3 Beds
    • 2 Baths
    • 1,194 Sq Ft
    • Built 1986

    Last Sold Summary

    • 16% Below List Price
    • $1,675/SF
    • 88 Days On Market

    Current Estimated Value $2,215,002

    Last Listing Agent Gene Orloff Sotheby's International Realty

    51 Wianno Cir, Osterville, MA 02655
  • /28

    $2,800,000

    Sold Jul 21, 2026

    106 Hathaway Rd, Osterville, MA 02655

    • 3 Beds
    • 3.5 Baths
    • 2,676 Sq Ft
    • Built 1964

    Last Sold Summary

    • $1,046/SF
    • 2 Days On Market

    Current Estimated Value $2,741,663

    Last Listing Agent Peggy Rowland Sotheby's International Realty

    106 Hathaway Rd, Osterville, MA 02655
  • /40

    $1,726,000

    Sold Jan 20, 2026

    199 E Bay Rd Unit 13, Osterville, MA 02655

    • 3 Beds
    • 3.5 Baths
    • 3,551 Sq Ft
    • Built 2000

    Last Sold Summary

    • 14% Below List Price
    • $486/SF
    • 58 Days On Market

    Current Estimated Value $1,805,602

    Last Listing Agent Susan Crasnick Sotheby's International Realty

    199 E Bay Rd Unit 13, Osterville, MA 02655
  • /54

    $975,000

    Sold Jul 02, 2026

    51 Falling Leaf Ln, Osterville, MA 02655

    • 2 Beds
    • 2 Baths
    • 2,010 Sq Ft
    • Built 2000

    Last Sold Summary

    • 3% Above List Price
    • $485/SF
    • 5 Days On Market

    Current Estimated Value $956,797

    Last Listing Agent Renee Legendre Lamacchia Realty, Inc.

    51 Falling Leaf Ln, Osterville, MA 02655
  • /29

    $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 $1,208,562

    Last Listing Agent Witter & Witter Boston/Cape Cod Compass

    50 Deerfield Rd, Osterville, MA 02655
  • /42

    $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 $4,554,865

    Last Listing Agent John Cotton Sotheby's International Realty

    405 Bridge St, Osterville, MA 02655
  • /35

    $1,015,000

    Sold Jun 30, 2026

    40 Waterfield Rd, Osterville, MA 02655

    • 4 Beds
    • 2 Baths
    • 1,775 Sq Ft
    • Built 1995

    Last Sold Summary

    • 10% Below List Price
    • $572/SF
    • 188 Days On Market

    Current Estimated Value $1,090,866

    Last Listing Agent Gervais Group Keller Williams Realty

    40 Waterfield Rd, Osterville, MA 02655
  • /35

    $600,000

    Sold Apr 17, 2026

    920 Main St Unit 2-1, Osterville, MA 02655

    • 2 Beds
    • 2 Baths
    • 1,150 Sq Ft
    • Built 1982

    Last Sold Summary

    • 2% Below List Price
    • $522/SF
    • 112 Days On Market

    Last Listing Agent Madeline LaCroix-Wheeler Keller Williams Realty

    920 Main St Unit 2-1, Osterville, MA 02655
  • /42

    $611,500

    Sold Nov 06, 2025

    17 Avalon Cir, Osterville, MA 02655

    • 3 Beds
    • 1.5 Baths
    • 1,316 Sq Ft
    • Built 1979

    Last Sold Summary

    • 2% Below List Price
    • $465/SF
    • 35 Days On Market

    Current Estimated Value $664,570

    Last Listing Agent John Fallon LAER Realty Partners

    17 Avalon Cir, Osterville, MA 02655
  • /41

    $1,349,000

    Sold May 08, 2026

    77 Robbins St, Osterville, MA 02655

    • 4 Beds
    • 2.5 Baths
    • 2,326 Sq Ft
    • Built 1966

    Last Sold Summary

    • 10% Below List Price
    • $580/SF
    • 212 Days On Market

    Current Estimated Value $1,386,983

    Last Listing Agent Deb Kenney Berkshire Hathaway HomeServices Robert Paul Properties

    77 Robbins St, Osterville, MA 02655
  • /42

    $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 $7,223,913

    Last Listing Agent John Cotton Sotheby's International Realty

    850 Sea View Ave, Osterville, MA 02655
  • /42

    $5,275,000

    Sold Dec 03, 2025

    245 N Bay Rd, Barnstable, MA 02655

    • 5 Beds
    • 5.5 Baths
    • 4,637 Sq Ft
    • Built 1988

    Last Sold Summary

    • 11% Below List Price
    • $1,138/SF
    • 31 Days On Market

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    245 N Bay Rd, Barnstable, MA 02655
  • /24

    $3,400,000

    Sold Oct 03, 2025

    780 Sea View Ave, Osterville, MA 02655

    • 4 Beds
    • 5 Baths
    • 5,762 Sq Ft
    • Built 1987

    Last Sold Summary

    • 3% Below List Price
    • $590/SF
    • 1 Day On Market

    Current Estimated Value $3,583,550

    Last Listing Agent Kathy O'Neil Sotheby's International Realty

    780 Sea View Ave, 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
  • /29

    $835,000

    Sold Jul 21, 2026

    153 Hickory Hill Cir, Osterville, MA 02655

    • 4 Beds
    • 2.5 Baths
    • 2,585 Sq Ft
    • Built 1973

    Last Sold Summary

    • 7% Below List Price
    • $323/SF
    • 54 Days On Market

    Current Estimated Value $913,667

    Last Listing Agent Amanda Kundel Kinlin Grover Compass

    153 Hickory Hill Cir, Osterville, MA 02655
  • /37

    $807,150

    Sold Aug 15, 2025

    26 Hinckley Cir, Osterville, MA 02655

    • 3 Beds
    • 3 Baths
    • 1,934 Sq Ft
    • Built 1958

    Last Sold Summary

    • 5% Below List Price
    • $417/SF
    • 30 Days On Market

    Current Estimated Value $869,543

    Last Listing Agent virginia guimond William Raveis R.E. & Home Services

    26 Hinckley Cir, Osterville, MA 02655
  • /40

    $1,600,000

    Sold Oct 15, 2025

    72 Hathaway Rd, Osterville, MA 02655

    • 4 Beds
    • 3 Baths
    • 2,050 Sq Ft
    • Built 1961

    Last Sold Summary

    • 14% Below List Price
    • $780/SF
    • 69 Days On Market

    Current Estimated Value $1,759,738

    Last Listing Agent John Cotton Sotheby's International Realty

    72 Hathaway Rd, Osterville, MA 02655
  • /33

    $575,000

    Sold Dec 29, 2025

    268 Bumps River Rd, Osterville, MA 02655

    • 2 Beds
    • 1 Bath
    • 1,179 Sq Ft
    • Built 1982

    Last Sold Summary

    • 8% Below List Price
    • $488/SF
    • 41 Days On Market

    Current Estimated Value $627,130

    Last Listing Agent Christine Richards Kinlin Grover Compass

    268 Bumps River Rd, Osterville, MA 02655
  • /42

    $10,500,000

    Sold Sep 16, 2025

    545 Sea View Ave, Osterville, MA 02655

    • 6 Beds
    • 5.5 Baths
    • 3,859 Sq Ft
    • Built 1947

    Last Sold Summary

    • 3% Below List Price
    • $2,721/SF
    • 105 Days On Market

    Current Estimated Value $8,352,724

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    545 Sea View Ave, Osterville, MA 02655
  • /34

    $760,000

    Sold Jan 30, 2026

    123 Tower Hill Rd, Osterville, MA 02655

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft
    • Built 1950

    Last Sold Summary

    • 5% Below List Price
    • $669/SF
    • 76 Days On Market

    Current Estimated Value $796,727

    Last Listing Agent Samantha Steward Compass

    123 Tower Hill Rd, Osterville, MA 02655
  • /26

    $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
    • 3 Days On Market

    Current Estimated Value $844,809

    Last Listing Agent Margaret Fearn Sotheby's International Realty

    64 Falling Leaf Ln, Osterville, MA 02655
  • /17

    $532,000

    Sold Dec 03, 2025

    17 Ebenezer Rd, Osterville, MA 02655

    • 3 Beds
    • 2 Baths
    • 1,267 Sq Ft
    • Built 1981

    Last Sold Summary

    • 7% Below List Price
    • $420/SF
    • 190 Days On Market

    Current Estimated Value $584,157

    Last Listing Agent Team 300 Today Real Estate

    17 Ebenezer Rd, Osterville, MA 02655
  • /41

    $1,490,000

    Sold May 29, 2026

    92 Wianno Cir, Osterville, MA 02655

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

    Last Sold Summary

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

    Current Estimated Value $1,623,564

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

    92 Wianno Cir, Osterville, MA 02655
  • /42

    $1,053,500

    Sold Jul 21, 2026

    170 Sturbridge Dr, Osterville, MA 02655

    • 2 Beds
    • 2.5 Baths
    • 1,992 Sq Ft
    • Built 1993

    Last Sold Summary

    • 8% Below List Price
    • $529/SF
    • 42 Days On Market

    Current Estimated Value $1,148,926

    Last Listing Agent Karen Rezendes Kinlin Grover Compass

    170 Sturbridge Dr, Osterville, MA 02655
  • /42

    $1,305,000

    Sold Apr 29, 2026

    53 Spice Ln, Osterville, MA 02655

    • 3 Beds
    • 1.5 Baths
    • 1,740 Sq Ft
    • Built 1964

    Last Sold Summary

    • 9% Above List Price
    • $750/SF
    • 2 Days On Market

    Current Estimated Value $1,224,144

    Last Listing Agent Livia Freitas Monteforte Compass

    53 Spice Ln, Osterville, MA 02655
  • /16

    $1,700,000

    Sold Jul 28, 2026

    107 Parsley Ln, Osterville, MA 02655

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft
    • Built 1968

    Last Sold Summary

    • 4% Above List Price
    • $759/SF
    • 2 Days On Market

    Current Estimated Value $1,615,692

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

    107 Parsley Ln, Osterville, MA 02655
  • /66

    $850,000

    Sold Jun 09, 2026

    42 Oak Ln, Osterville, MA 02655

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1957

    Last Sold Summary

    • $460/SF
    • 6 Days On Market

    Current Estimated Value $856,230

    Last Listing Agent Deb Kenney Berkshire Hathaway HomeServices Robert Paul Properties

    42 Oak Ln, Osterville, MA 02655
  • /42

    $739,000

    Sold Oct 31, 2025

    165 Concord Ln, Osterville, MA 02655

    • 3 Beds
    • 3 Baths
    • 1,803 Sq Ft
    • Built 1982

    Last Sold Summary

    • $410/SF
    • 4 Days On Market

    Last Listing Agent Marchildon Hagop Team Kinlin Grover Compass

    165 Concord Ln, Osterville, MA 02655

Showing Results 1 - 40, Page 1 of 2

Frequently Asked Questions

What is the average time to sell a house in Osterville, MA?
The houses for sale in Osterville, MA spend an average of 62 days on the market.
What is the number of active homes for sale in Osterville, MA?
There are 38 active homes for sale in Osterville, MA.

Home Price Trends

Median Sale Price
$1,305,000
Median Single Family Sale Price
$1,505,000
Median 2 Bedroom Sale Price
$649,000
Average Price Per Sq Ft
$796
Number of Homes for Sale
38
Last 12 months Home Sales
90
Months of Supply
5.10
Median List Price
$1,579,000
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
1%
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