5,118

Homes in ZIP Code 34229

Section Image
  • 1102 Jessie Harbor Dr, Osprey, FL 34229
    1102 Jessie Harbor Dr, Osprey, FL 34229
    /2

    $435,000

    Sold Feb 20, 2026

    1102 Jessie Harbor Dr, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,425 Sq Ft
    • Built 2004

    Last Sold Summary

    • 8% Below List Price
    • $305/SF
    • 9 Days On Market

    Current Estimated Value $434,089

    Last Listing Agent Mackenzie Davis-Mahan DOWNING FRYE REALTY, INC.

    1102 Jessie Harbor Dr, Osprey, FL 34229
    • 236 Hidden Bay Dr Unit 504, Osprey, FL 34229
      236 Hidden Bay Dr Unit 504, Osprey, FL 34229
      /2

      Est $789,981

      Not Listed For Sale

      236 Hidden Bay Dr Unit 504, Osprey, FL 34229

      • 3 Beds
      • 3 Baths
      • 2,100 Sq Ft
      • Built 1997
      236 Hidden Bay Dr Unit 504, Osprey, FL 34229

      Last Sold Summary

      • 115 Days On Market

  • 4267 Expedition Way, Osprey, FL 34229
    4267 Expedition Way, Osprey, FL 34229
    /2

    $295,000

    Sold Nov 14, 2025

    4267 Expedition Way, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,135 Sq Ft
    • Built 2017

    Last Sold Summary

    • 5% Below List Price
    • $260/SF
    • 87 Days On Market

    Current Estimated Value $283,968

    Last Listing Agent Judi Cipollina COLDWELL BANKER REALTY

    4267 Expedition Way, Osprey, FL 34229
    • 1762 Island Way, Osprey, FL 34229
      1762 Island Way, Osprey, FL 34229
      1762 Island Way, Osprey, FL 34229
      /63

      Est $1,007,358

      Not Listed For Sale

      1762 Island Way, Osprey, FL 34229

      • 3 Beds
      • 3 Baths
      • 2,462 Sq Ft
      • Built 1988
      1762 Island Way, Osprey, FL 34229

      Last Sold Summary

      • 11 Days On Market

  • 409 N Point Rd Unit 603, Osprey, FL 34229
    409 N Point Rd Unit 603, Osprey, FL 34229
    /2

    $560,000

    Sold Mar 31, 2026

    409 N Point Rd Unit 603, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,203 Sq Ft
    • Built 2004

    Last Sold Summary

    • 29% Below List Price
    • $254/SF
    • 727 Days On Market

    Current Estimated Value $697,648

    Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

    409 N Point Rd Unit 603, Osprey, FL 34229
    • 427 Washington Ave, Osprey, FL 34229
      427 Washington Ave, Osprey, FL 34229
      /2

      Est $299,435

      Not Listed For Sale

      427 Washington Ave, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 1957
      427 Washington Ave, Osprey, FL 34229

      Last Sold Summary

      • 195 Days On Market

  • 570 Blackburn Point Rd Unit 19, Osprey, FL 34229
    570 Blackburn Point Rd Unit 19, Osprey, FL 34229
    /2

    $140,000

    Sold Dec 12, 2025

    570 Blackburn Point Rd Unit 19, Osprey, FL 34229

    • Built 2006

    Last Sold Summary

    • 3% Below List Price
    • 59 Days On Market

    Current Estimated Value $140,268

    Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

    570 Blackburn Point Rd Unit 19, Osprey, FL 34229
    • 250 Glenwood Ave, Osprey, FL 34229
      250 Glenwood Ave, Osprey, FL 34229
      250 Glenwood Ave, Osprey, FL 34229
      /62

      Est $317,334

      Not Listed For Sale

      250 Glenwood Ave, Osprey, FL 34229

      • 2 Beds
      • 2 Baths
      • 1,118 Sq Ft
      • Built 1986
      250 Glenwood Ave, Osprey, FL 34229

      Last Sold Summary

      • 9 Days On Market

  • 616 Crane Prairie Way, Osprey, FL 34229
    616 Crane Prairie Way, Osprey, FL 34229
    /2

    $840,000

    Sold Apr 13, 2026

    616 Crane Prairie Way, Osprey, FL 34229

    • 3 Beds
    • 4 Baths
    • 3,561 Sq Ft
    • Built 2005

    Last Sold Summary

    • 12% Below List Price
    • $236/SF
    • 39 Days On Market

    Current Estimated Value $850,841

    Last Listing Agent Matthew Greenland KELLER WILLIAMS ISLAND LIFE REAL ESTATE

    616 Crane Prairie Way, Osprey, FL 34229
    • 208 Pennsylvania Ave, Osprey, FL 34229
      208 Pennsylvania Ave, Osprey, FL 34229
      /2

      Est $287,167

      Not Listed For Sale

      208 Pennsylvania Ave, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 900 Sq Ft
      • Built 1963
      208 Pennsylvania Ave, Osprey, FL 34229

      Last Sold Summary

      • 33 Days On Market

  • 530 N Mac Ewen Dr, Osprey, FL 34229
    530 N Mac Ewen Dr, Osprey, FL 34229
    /2

    $2,300,000

    Sold Apr 07, 2026

    530 N Mac Ewen Dr, Osprey, FL 34229

    • 4 Beds
    • 5.5 Baths
    • 4,346 Sq Ft
    • Built 2002

    Last Sold Summary

    • 4% Below List Price
    • $529/SF
    • 27 Days On Market

    Current Estimated Value $2,286,461

    Last Listing Agent Niall Phelan LPT REALTY, LLC

    530 N Mac Ewen Dr, Osprey, FL 34229
    • 525 S Shore Dr, Osprey, FL 34229
      525 S Shore Dr, Osprey, FL 34229
      /2

      Est $1,664,513

      Not Listed For Sale

      525 S Shore Dr, Osprey, FL 34229

      • 3 Beds
      • 3 Baths
      • 2,315 Sq Ft
      • Built 1972
      525 S Shore Dr, Osprey, FL 34229

      Last Sold Summary

      • 108 Days On Market

  • 4235 Expedition Way Unit 102, Osprey, FL 34229
    4235 Expedition Way Unit 102, Osprey, FL 34229
    /2

    $365,000

    Sold Apr 29, 2026

    4235 Expedition Way Unit 102, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft
    • Built 2016

    Last Sold Summary

    • 4% Below List Price
    • $232/SF
    • 4 Days On Market

    Current Estimated Value $364,383

    Last Listing Agent Tim Weller EXIT KING REALTY

    4235 Expedition Way Unit 102, Osprey, FL 34229
    • 131 Tina Island Dr, Osprey, FL 34229
      131 Tina Island Dr, Osprey, FL 34229
      /2

      Est $1,152,918

      Not Listed For Sale

      131 Tina Island Dr, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 1,787 Sq Ft
      • Built 1978
      131 Tina Island Dr, Osprey, FL 34229

      Last Sold Summary

      • 10 Days On Market

  • 1164 Beachcomber Ct Unit 19, Osprey, FL 34229
    1164 Beachcomber Ct Unit 19, Osprey, FL 34229
    /2

    $527,500

    Sold Sep 11, 2025

    1164 Beachcomber Ct Unit 19, Osprey, FL 34229

    • 3 Beds
    • 2.5 Baths
    • 1,952 Sq Ft
    • Built 2005

    Last Sold Summary

    • 4% Below List Price
    • $270/SF
    • 60 Days On Market

    Current Estimated Value $512,434

    Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

    1164 Beachcomber Ct Unit 19, Osprey, FL 34229
    • 935 Blue Heron Overlook, Osprey, FL 34229
      935 Blue Heron Overlook, Osprey, FL 34229
      935 Blue Heron Overlook, Osprey, FL 34229
      /27

      Est $1,498,101

      Not Listed For Sale

      935 Blue Heron Overlook, Osprey, FL 34229

      • 4 Beds
      • 4 Baths
      • 3,665 Sq Ft
      • Built 1990
      935 Blue Heron Overlook, Osprey, FL 34229

      Last Sold Summary

      • 0 Days On Market

  • 678 Crane Prairie Way, Osprey, FL 34229
    678 Crane Prairie Way, Osprey, FL 34229
    /2

    $850,000

    Sold Dec 17, 2025

    678 Crane Prairie Way, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 2,483 Sq Ft
    • Built 2003

    Last Sold Summary

    • 2% Below List Price
    • $342/SF
    • 4 Days On Market

    Current Estimated Value $830,072

    Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    678 Crane Prairie Way, Osprey, FL 34229
    • 448 Park Trace Blvd, Osprey, FL 34229
      448 Park Trace Blvd, Osprey, FL 34229
      /2

      Est $783,619

      Not Listed For Sale

      448 Park Trace Blvd, Osprey, FL 34229

      • 4 Beds
      • 3 Baths
      • 3,060 Sq Ft
      • Built 2002
      448 Park Trace Blvd, Osprey, FL 34229

      Last Sold Summary

      • 145 Days On Market

  • 370 Sugar Mill Dr, Osprey, FL 34229
    370 Sugar Mill Dr, Osprey, FL 34229
    /2

    $2,189,000

    Sold Feb 09, 2026

    370 Sugar Mill Dr, Osprey, FL 34229

    • 5 Beds
    • 5.5 Baths
    • 4,783 Sq Ft
    • Built 1996

    Last Sold Summary

    • 11% Below List Price
    • $458/SF
    • 0 Days On Market

    Current Estimated Value $2,217,116

    Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

    370 Sugar Mill Dr, Osprey, FL 34229
    • 385 N Point Rd Unit 802, Osprey, FL 34229
      385 N Point Rd Unit 802, Osprey, FL 34229
      /2

      Est $1,952,600

      Not Listed For Sale

      385 N Point Rd Unit 802, Osprey, FL 34229

      • 3 Beds
      • 3.5 Baths
      • 3,738 Sq Ft
      • Built 2000
      385 N Point Rd Unit 802, Osprey, FL 34229

      Last Sold Summary

      • 0 Days On Market

  • 1212 Windward Dr, Osprey, FL 34229
    1212 Windward Dr, Osprey, FL 34229
    /2

    $645,000

    Sold Aug 25, 2025

    1212 Windward Dr, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 1,994 Sq Ft
    • Built 1982

    Last Sold Summary

    • 17% Below List Price
    • $323/SF
    • 174 Days On Market

    Current Estimated Value $662,246

    Last Listing Agent Mark Lyda GENEROUS PROPERTY

    1212 Windward Dr, Osprey, FL 34229
    • 663 Crane Prairie Way, Osprey, FL 34229
      663 Crane Prairie Way, Osprey, FL 34229
      /2

      Est $713,778

      Not Listed For Sale

      663 Crane Prairie Way, Osprey, FL 34229

      • 4 Beds
      • 3 Baths
      • 2,306 Sq Ft
      • Built 2003
      663 Crane Prairie Way, Osprey, FL 34229

      Last Sold Summary

      • 9 Days On Market

  • 107 Woodland Place Unit 107, Osprey, FL 34229
    107 Woodland Place Unit 107, Osprey, FL 34229
    /2

    $150,000

    Sold Jul 25, 2025

    107 Woodland Place Unit 107, Osprey, FL 34229

    • 1 Bed
    • 1.5 Baths
    • 865 Sq Ft
    • Built 1979

    Last Sold Summary

    • 11% Below List Price
    • $173/SF
    • 49 Days On Market

    Current Estimated Value $159,403

    Last Listing Agent Carla Rayman Kidd COLDWELL BANKER REALTY

    107 Woodland Place Unit 107, Osprey, FL 34229
    • 108 Park Dr, Osprey, FL 34229
      108 Park Dr, Osprey, FL 34229
      /2

      Est $565,119

      Not Listed For Sale

      108 Park Dr, Osprey, FL 34229

      • 4 Beds
      • 3 Baths
      • 2,768 Sq Ft
      • Built 1956
      108 Park Dr, Osprey, FL 34229

      Last Sold Summary

      • 41 Days On Market

  • 201 Woodland Dr Unit 201, Osprey, FL 34229
    201 Woodland Dr Unit 201, Osprey, FL 34229
    /2

    $200,000

    Sold Dec 09, 2025

    201 Woodland Dr Unit 201, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,316 Sq Ft
    • Built 1980

    Last Sold Summary

    • 33% Below List Price
    • $152/SF
    • 346 Days On Market

    Current Estimated Value $200,758

    Last Listing Agent Lauren Meadows PREFERRED PROPERTIES OF VENICE INC

    201 Woodland Dr Unit 201, Osprey, FL 34229
    • 201 Saint James Park, Osprey, FL 34229
      201 Saint James Park, Osprey, FL 34229
      /2

      Est $1,008,878

      Not Listed For Sale

      201 Saint James Park, Osprey, FL 34229

      • 3 Beds
      • 3 Baths
      • 2,855 Sq Ft
      • Built 1997
      201 Saint James Park, Osprey, FL 34229

      Last Sold Summary

      • 281 Days On Market

  • 201 Eaglenook Way, Osprey, FL 34229
    201 Eaglenook Way, Osprey, FL 34229
    /2

    $1,014,000

    Sold Nov 12, 2025

    201 Eaglenook Way, Osprey, FL 34229

    • 4 Beds
    • 3 Baths
    • 3,379 Sq Ft
    • Built 1992

    Last Sold Summary

    • 16% Below List Price
    • $300/SF
    • 211 Days On Market

    Current Estimated Value $1,053,192

    Last Listing Agent Dawn Bear WILLIAM RAVEIS - FLORIDA LLC

    201 Eaglenook Way, Osprey, FL 34229
    • 223 Saint James Park, Osprey, FL 34229
      223 Saint James Park, Osprey, FL 34229
      /2

      Est $1,191,246

      Not Listed For Sale

      223 Saint James Park, Osprey, FL 34229

      • 3 Beds
      • 5 Baths
      • 3,321 Sq Ft
      • Built 1991
      223 Saint James Park, Osprey, FL 34229

      Last Sold Summary

      • 20 Days On Market

  • 444 Washington Ave, Osprey, FL 34229
    444 Washington Ave, Osprey, FL 34229
    /2

    $200,000

    Sold Oct 06, 2025

    444 Washington Ave, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 1,284 Sq Ft
    • Built 1953

    Last Sold Summary

    • 20% Below List Price
    • $156/SF
    • 9 Days On Market

    Current Estimated Value $215,121

    Last Listing Agent Hansel Pitts COLDWELL BANKER SARASOTA CENT.

    444 Washington Ave, Osprey, FL 34229
    • 442 Webbs Cove, Osprey, FL 34229
      442 Webbs Cove, Osprey, FL 34229
      442 Webbs Cove, Osprey, FL 34229
      /11

      Est $2,151,742

      Not Listed For Sale

      442 Webbs Cove, Osprey, FL 34229

      • 3 Beds
      • 3.5 Baths
      • 3,768 Sq Ft
      • Built 1983
      442 Webbs Cove, Osprey, FL 34229

      Last Sold Summary

  • 116 Villa Dr Unit 116, Osprey, FL 34229
    116 Villa Dr Unit 116, Osprey, FL 34229
    /2

    $525,000

    Sold Sep 30, 2025

    116 Villa Dr Unit 116, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,221 Sq Ft
    • Built 1968

    Last Sold Summary

    • $430/SF
    • 2 Days On Market

    Current Estimated Value $483,747

    Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC

    116 Villa Dr Unit 116, Osprey, FL 34229
    • 473 Glenwood Ave, Osprey, FL 34229
      473 Glenwood Ave, Osprey, FL 34229
      473 Glenwood Ave, Osprey, FL 34229
      /42

      Est $249,793

      Not Listed For Sale

      473 Glenwood Ave, Osprey, FL 34229

      • 1 Bed
      • 1 Bath
      • 626 Sq Ft
      • Built 1956
      473 Glenwood Ave, Osprey, FL 34229

      Last Sold Summary

      • 12 Days On Market

    • 453 Webbs Cove, Osprey, FL 34229
      453 Webbs Cove, Osprey, FL 34229
      453 Webbs Cove, Osprey, FL 34229
      /65

      Est $1,983,648

      Not Listed For Sale

      453 Webbs Cove, Osprey, FL 34229

      • 3 Beds
      • 3.5 Baths
      • 3,953 Sq Ft
      • Built 1992
      453 Webbs Cove, Osprey, FL 34229

      Last Sold Summary

      • 73 Days On Market

    • 603 Oak Bay Dr, Osprey, FL 34229
      603 Oak Bay Dr, Osprey, FL 34229
      /2

      Est $584,948

      Not Listed For Sale

      603 Oak Bay Dr, Osprey, FL 34229

      • 4 Beds
      • 2 Baths
      • 2,312 Sq Ft
      • Built 1997
      603 Oak Bay Dr, Osprey, FL 34229

      Last Sold Summary

      • 133 Days On Market

    • 767 Pine Run Dr, Osprey, FL 34229
      767 Pine Run Dr, Osprey, FL 34229
      767 Pine Run Dr, Osprey, FL 34229
      /66

      Est $153,358

      Not Listed For Sale

      767 Pine Run Dr, Osprey, FL 34229

      • 1 Bed
      • 1 Bath
      • 736 Sq Ft
      • Built 1973
      767 Pine Run Dr, Osprey, FL 34229

      Last Sold Summary

      • 4 Days On Market

    • 760 Pine Run Dr, Osprey, FL 34229
      760 Pine Run Dr, Osprey, FL 34229
      760 Pine Run Dr, Osprey, FL 34229
      /43

      Est $122,370

      Not Listed For Sale

      760 Pine Run Dr, Osprey, FL 34229

      • 1 Bed
      • 1 Bath
      • 586 Sq Ft
      • Built 1973
      760 Pine Run Dr, Osprey, FL 34229

      Last Sold Summary

      • 2 Days On Market

    • 756 Pine Run Dr, Osprey, FL 34229
      756 Pine Run Dr, Osprey, FL 34229
      756 Pine Run Dr, Osprey, FL 34229
      /72

      Est $234,982

      Not Listed For Sale

      756 Pine Run Dr, Osprey, FL 34229

      • 2 Beds
      • 2 Baths
      • 1,224 Sq Ft
      • Built 1973
      756 Pine Run Dr, Osprey, FL 34229

      Last Sold Summary

      • 79 Days On Market

    • 510 Old Venice Rd, Osprey, FL 34229
      510 Old Venice Rd, Osprey, FL 34229
      /2

      Not Listed For Sale

      510 Old Venice Rd, Osprey, FL 34229

      • 3 Beds
      • 2.5 Baths
      • 2,176 Sq Ft
      • Built 1997
      510 Old Venice Rd, Osprey, FL 34229

      Last Sold Summary

      • 114 Days On Market

    • 223 Hidden Bay Dr Unit 305, Osprey, FL 34229
      223 Hidden Bay Dr Unit 305, Osprey, FL 34229
      /2

      Est $370,077

      Not Listed For Sale

      223 Hidden Bay Dr Unit 305, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 1,515 Sq Ft
      • Built 1997
      223 Hidden Bay Dr Unit 305, Osprey, FL 34229

      Last Sold Summary

      • 2 Days On Market

    • 284 Sugar Mill Dr, Osprey, FL 34229
      284 Sugar Mill Dr, Osprey, FL 34229
      284 Sugar Mill Dr, Osprey, FL 34229
      /93

      Est $1,817,202

      Not Listed For Sale

      284 Sugar Mill Dr, Osprey, FL 34229

      • 4 Beds
      • 3.5 Baths
      • 4,135 Sq Ft
      • Built 1994
      284 Sugar Mill Dr, Osprey, FL 34229

      Last Sold Summary

      • 4 Days On Market

Showing Results 601 - 640, Page 16 of 18

Florida Sarasota County Osprey 34229

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