5,018

Osprey, FL Homes

Section Image
    • 184 Park Trace Blvd, Osprey, FL 34229
      184 Park Trace Blvd, Osprey, FL 34229
      184 Park Trace Blvd, Osprey, FL 34229
      /85

      Est $945,026

      Not Listed For Sale

      184 Park Trace Blvd, Osprey, FL 34229

      • 5 Beds
      • 4.5 Baths
      • 3,420 Sq Ft
      • Built 2003
      184 Park Trace Blvd, Osprey, FL 34229

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Mark Klecka COLDWELL BANKER REALTY

  • 14041 Bellagio Way Unit 218, Osprey, FL 34229
    14041 Bellagio Way Unit 218, Osprey, FL 34229
    /2

    $920,000

    Sold Jul 07, 2026

    14041 Bellagio Way Unit 218, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 2,086 Sq Ft
    • Built 2006

    Last Sold Summary

    • 20% Below List Price
    • $441/SF
    • 175 Days On Market

    Current Estimated Value $956,578

    Last Listing Agent Kelli Eggen COLDWELL BANKER REALTY

    14041 Bellagio Way Unit 218, Osprey, FL 34229
    • 738 N MacEwen Dr, Osprey, FL 34229
      738 N MacEwen Dr, Osprey, FL 34229
      /2

      Est $1,609,174

      Not Listed For Sale

      738 N MacEwen Dr, Osprey, FL 34229

      • 5 Beds
      • 5.5 Baths
      • 4,614 Sq Ft
      • Built 2003
      738 N MacEwen Dr, Osprey, FL 34229

      Last Sold Summary

      • 193 Days On Market

      Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  • 340 Osprey Point Dr, Osprey, FL 34229
    340 Osprey Point Dr, Osprey, FL 34229
    /2

    $1,900,000

    Sold Feb 10, 2026

    340 Osprey Point Dr, Osprey, FL 34229

    • 5 Beds
    • 7 Baths
    • 6,001 Sq Ft
    • Built 1998

    Last Sold Summary

    • 24% Below List Price
    • $317/SF
    • 273 Days On Market

    Current Estimated Value $1,943,538

    Last Listing Agent Lee Brewer RE/MAX ALLIANCE GROUP

    340 Osprey Point Dr, Osprey, FL 34229
    • 110 N Creek Ln, Osprey, FL 34229
      110 N Creek Ln, Osprey, FL 34229
      /2

      Est $1,246,978

      Not Listed For Sale

      110 N Creek Ln, Osprey, FL 34229

      • 3 Beds
      • 3.5 Baths
      • 4,071 Sq Ft
      • Built 2002
      110 N Creek Ln, Osprey, FL 34229

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Tina Timmons CENTURY 21 ROSEBAY

  • 494 Meadow Sweet Cir, Osprey, FL 34229
    494 Meadow Sweet Cir, Osprey, FL 34229
    /2

    $550,000

    Sold Feb 19, 2026

    494 Meadow Sweet Cir, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 1,791 Sq Ft
    • Built 1997

    Last Sold Summary

    • 8% Below List Price
    • $307/SF
    • 7 Days On Market

    Current Estimated Value $555,189

    Last Listing Agent Carlos Saramago EXIT KING REALTY

    494 Meadow Sweet Cir, Osprey, FL 34229
    • 17 Bayhead Ln, Osprey, FL 34229
      17 Bayhead Ln, Osprey, FL 34229
      17 Bayhead Ln, Osprey, FL 34229
      /65

      Est $1,215,914

      Not Listed For Sale

      17 Bayhead Ln, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 2,335 Sq Ft
      • Built 1992
      17 Bayhead Ln, Osprey, FL 34229

      Last Sold Summary

      • 87 Days On Market

      Last Listing Agent Kim Mitchell MICHAEL SAUNDERS & COMPANY

  • 447 Oak Point Rd, Osprey, FL 34229
    447 Oak Point Rd, Osprey, FL 34229
    /2

    $520,000

    Sold Dec 30, 2025

    447 Oak Point Rd, Osprey, FL 34229

    • 4 Beds
    • 3 Baths
    • 2,688 Sq Ft
    • Built 1994

    Last Sold Summary

    • 5% Below List Price
    • $193/SF
    • 49 Days On Market

    Current Estimated Value $521,209

    Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

    447 Oak Point Rd, Osprey, FL 34229
    • 146 Yacht Harbor Dr, Osprey, FL 34229
      146 Yacht Harbor Dr, Osprey, FL 34229
      /2

      Est $938,234

      Not Listed For Sale

      146 Yacht Harbor Dr, Osprey, FL 34229

      • 3 Beds
      • 2.5 Baths
      • 2,627 Sq Ft
      • Built 1986
      146 Yacht Harbor Dr, Osprey, FL 34229

      Last Sold Summary

      Last Listing Agent Susanne Losso COLDWELL BANKER REALTY

  • 127 Park Trace Blvd, Osprey, FL 34229
    127 Park Trace Blvd, Osprey, FL 34229
    /2

    $789,000

    Sold Jul 24, 2026

    127 Park Trace Blvd, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 2,463 Sq Ft
    • Built 2003

    Last Sold Summary

    • 1% Below List Price
    • $320/SF
    • 17 Days On Market

    Current Estimated Value $785,115

    Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

    127 Park Trace Blvd, Osprey, FL 34229
    • 676 Eagle Watch Ln, Osprey, FL 34229
      676 Eagle Watch Ln, Osprey, FL 34229
      /2

      Est $1,939,535

      Not Listed For Sale

      676 Eagle Watch Ln, Osprey, FL 34229

      • 5 Beds
      • 5.5 Baths
      • 5,399 Sq Ft
      • Built 1992
      676 Eagle Watch Ln, Osprey, FL 34229

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Jamie Mullis COLDWELL BANKER REALTY

  • 300 Tropic Dr, Osprey, FL 34229
    300 Tropic Dr, Osprey, FL 34229
    /2

    $155,000

    Sold Feb 24, 2026

    300 Tropic Dr, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,031 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Below List Price
    • $150/SF
    • 54 Days On Market

    Last Listing Agent Heidi Lionetti WHITE SANDS REALTY GROUP FL

    300 Tropic Dr, Osprey, FL 34229
    • 104 Woodland Place, Osprey, FL 34229
      104 Woodland Place, Osprey, FL 34229
      /2

      Est $249,521

      Not Listed For Sale

      104 Woodland Place, Osprey, FL 34229

      • 2 Beds
      • 2 Baths
      • 1,316 Sq Ft
      • Built 1979
      104 Woodland Place, Osprey, FL 34229

      Last Sold Summary

      Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  • 3936 Waypoint Ave, Osprey, FL 34229
    3936 Waypoint Ave, Osprey, FL 34229
    /2

    $1,001,000

    Sold Apr 27, 2026

    3936 Waypoint Ave, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,323 Sq Ft
    • Built 2016

    Last Sold Summary

    • 4% Below List Price
    • $431/SF
    • 3 Days On Market

    Current Estimated Value $1,010,740

    Last Listing Agent Larry Brzostek RE/MAX ALLIANCE GROUP

    3936 Waypoint Ave, Osprey, FL 34229
    • 846 Oak Pond Dr, Osprey, FL 34229
      846 Oak Pond Dr, Osprey, FL 34229
      846 Oak Pond Dr, Osprey, FL 34229
      /25

      Est $527,035

      Not Listed For Sale

      846 Oak Pond Dr, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 2,126 Sq Ft
      • Built 1995
      846 Oak Pond Dr, Osprey, FL 34229

      Last Sold Summary

      • 113 Days On Market

      Last Listing Agent Janet Oberholtzer MICHAEL SAUNDERS & COMPANY

  • 32 Siesta Cir W, Osprey, FL 34229
    32 Siesta Cir W, Osprey, FL 34229
    /2

    $69,000

    Sold Jun 01, 2026

    32 Siesta Cir W, Osprey, FL 34229

    • 1 Bed
    • 1 Bath
    • 480 Sq Ft
    • Built 1968

    Last Sold Summary

    • $144/SF
    • 2 Days On Market

    Last Listing Agent Karen Geiger COLDWELL BANKER SARASOTA CENT.

    32 Siesta Cir W, Osprey, FL 34229
    • 564 Meadow Sweet Cir, Osprey, FL 34229
      564 Meadow Sweet Cir, Osprey, FL 34229
      564 Meadow Sweet Cir, Osprey, FL 34229
      /55

      Est $499,618

      Not Listed For Sale

      564 Meadow Sweet Cir, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 1,808 Sq Ft
      • Built 2003
      564 Meadow Sweet Cir, Osprey, FL 34229

      Last Sold Summary

      • 57 Days On Market

      Last Listing Agent Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

  • 252 Sun Air Cir, Osprey, FL 34229
    252 Sun Air Cir, Osprey, FL 34229
    /2

    $195,000

    Sold Jun 12, 2026

    252 Sun Air Cir, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1979

    Last Sold Summary

    • 17% Below List Price
    • $169/SF
    • 66 Days On Market

    Last Listing Agent Karen Geiger COLDWELL BANKER SARASOTA CENT.

    252 Sun Air Cir, Osprey, FL 34229
    • 587 Meadow Sweet Cir, Osprey, FL 34229
      587 Meadow Sweet Cir, Osprey, FL 34229
      587 Meadow Sweet Cir, Osprey, FL 34229
      /79

      Est $560,510

      Not Listed For Sale

      587 Meadow Sweet Cir, Osprey, FL 34229

      • 3 Beds
      • 2.5 Baths
      • 2,217 Sq Ft
      • Built 1996
      587 Meadow Sweet Cir, Osprey, FL 34229

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

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

    $565,000

    Sold Jun 04, 2026

    102 Windward Dr, Osprey, FL 34229

    • 3 Beds
    • 2.5 Baths
    • 2,134 Sq Ft
    • Built 1986

    Last Sold Summary

    • 29% Below List Price
    • $265/SF
    • 169 Days On Market

    Current Estimated Value $641,991

    Last Listing Agent Regina Putrino WILLIAM RAVEIS - FLORIDA LLC

    102 Windward Dr, Osprey, FL 34229
    • 230 Burney Rd, Osprey, FL 34229
      230 Burney Rd, Osprey, FL 34229
      /2

      Est $490,010

      Not Listed For Sale

      230 Burney Rd, Osprey, FL 34229

      • 4 Beds
      • 3 Baths
      • 2,219 Sq Ft
      • Built 1985
      230 Burney Rd, Osprey, FL 34229

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Amanda Gilliland COLDWELL BANKER REALTY

  • 392 Park Trace Blvd, Osprey, FL 34229
    392 Park Trace Blvd, Osprey, FL 34229
    /2

    $880,000

    Sold Jan 30, 2026

    392 Park Trace Blvd, Osprey, FL 34229

    • 4 Beds
    • 3 Baths
    • 2,802 Sq Ft
    • Built 2001

    Last Sold Summary

    • 6% Below List Price
    • $314/SF
    • 32 Days On Market

    Current Estimated Value $886,293

    Last Listing Agent Ryan Skrzypkowski COLDWELL BANKER REALTY

    392 Park Trace Blvd, Osprey, FL 34229
    • 128 Villa Dr Unit 128, Osprey, FL 34229
      128 Villa Dr Unit 128, Osprey, FL 34229
      128 Villa Dr Unit 128, Osprey, FL 34229
      /64

      Est $523,281

      Not Listed For Sale

      128 Villa Dr Unit 128, Osprey, FL 34229

      • 2 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1978
      128 Villa Dr Unit 128, Osprey, FL 34229

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Raphael Carlisi FINE PROPERTIES

  • 393 N Point Rd Unit 301, Osprey, FL 34229
    393 N Point Rd Unit 301, Osprey, FL 34229
    /2

    $510,000

    Sold Jul 17, 2026

    393 N Point Rd Unit 301, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,594 Sq Ft
    • Built 2001

    Last Sold Summary

    • 18% Below List Price
    • $197/SF
    • 79 Days On Market

    Current Estimated Value $612,615

    Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

    393 N Point Rd Unit 301, Osprey, FL 34229
    • 433 S Shore Dr, Osprey, FL 34229
      433 S Shore Dr, Osprey, FL 34229
      433 S Shore Dr, Osprey, FL 34229
      /70

      Est $620,258

      Not Listed For Sale

      433 S Shore Dr, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 1,868 Sq Ft
      • Built 1984
      433 S Shore Dr, Osprey, FL 34229

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Christine Pope MICHAEL SAUNDERS & COMPANY

  • 1049 N Casey Key Rd, Osprey, FL 34229
    1049 N Casey Key Rd, Osprey, FL 34229
    /2

    $4,040,000

    Sold Jan 05, 2026

    1049 N Casey Key Rd, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,582 Sq Ft
    • Built 1990

    Last Sold Summary

    • 15% Below List Price
    • $1,565/SF
    • 212 Days On Market

    Current Estimated Value $3,734,691

    Last Listing Agent Courtney Green PREMIER SOTHEBYS INTL REALTY

    1049 N Casey Key Rd, Osprey, FL 34229
    • 695 Rivendell Blvd, Osprey, FL 34229
      695 Rivendell Blvd, Osprey, FL 34229
      /2

      Est $626,095

      Not Listed For Sale

      695 Rivendell Blvd, Osprey, FL 34229

      • 4 Beds
      • 3 Baths
      • 2,256 Sq Ft
      • Built 2001
      695 Rivendell Blvd, Osprey, FL 34229

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Dan Henson DALTON WADE INC

  • 1016 Scherer Way, Osprey, FL 34229
    1016 Scherer Way, Osprey, FL 34229
    /2

    $925,000

    Sold Jun 08, 2026

    1016 Scherer Way, Osprey, FL 34229

    • 4 Beds
    • 3 Baths
    • 2,921 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $317/SF
    • 1 Day On Market

    Current Estimated Value $924,911

    Last Listing Agent Rachel Tritschler RE/MAX ALLIANCE GROUP

    1016 Scherer Way, Osprey, FL 34229
    • 242 Hidden Bay Dr Unit 304, Osprey, FL 34229
      242 Hidden Bay Dr Unit 304, Osprey, FL 34229
      /2

      Est $719,169

      Not Listed For Sale

      242 Hidden Bay Dr Unit 304, Osprey, FL 34229

      • 3 Beds
      • 3 Baths
      • 2,100 Sq Ft
      • Built 1999
      242 Hidden Bay Dr Unit 304, Osprey, FL 34229

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

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

    $800,000

    Sold Aug 24, 2026

    204 Windward Dr, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,486 Sq Ft
    • Built 1986

    Last Sold Summary

    • 24% Below List Price
    • $322/SF
    • 81 Days On Market

    Current Estimated Value $842,915

    Last Listing Agent Sharon Lewis GOLF & BAY PROPERTIES LLC

    204 Windward Dr, Osprey, FL 34229
    • 393 N Point Rd Unit 302, Osprey, FL 34229
      393 N Point Rd Unit 302, Osprey, FL 34229
      /2

      Est $450,176

      Not Listed For Sale

      393 N Point Rd Unit 302, Osprey, FL 34229

      • 3 Beds
      • 3 Baths
      • 2,055 Sq Ft
      • Built 2001
      393 N Point Rd Unit 302, Osprey, FL 34229

      Last Sold Summary

      • 106 Days On Market

      Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  • 711 Shadow Bay Way, Osprey, FL 34229
    711 Shadow Bay Way, Osprey, FL 34229
    /2

    $545,000

    Sold Mar 31, 2026

    711 Shadow Bay Way, Osprey, FL 34229

    • 4 Beds
    • 2 Baths
    • 2,133 Sq Ft
    • Built 2002

    Last Sold Summary

    • 9% Below List Price
    • $256/SF
    • 77 Days On Market

    Current Estimated Value $544,142

    Last Listing Agent Susan Keal MICHAEL SAUNDERS & COMPANY

    711 Shadow Bay Way, Osprey, FL 34229
    • 812 Foothill Ct, Osprey, FL 34229
      812 Foothill Ct, Osprey, FL 34229
      812 Foothill Ct, Osprey, FL 34229
      /3

      Est $636,879

      Not Listed For Sale

      812 Foothill Ct, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 2,282 Sq Ft
      • Built 2002
      812 Foothill Ct, Osprey, FL 34229

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.

  • 708 Anna Hope Ln, Osprey, FL 34229
    708 Anna Hope Ln, Osprey, FL 34229
    /2

    $520,000

    Sold Nov 14, 2025

    708 Anna Hope Ln, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 2,133 Sq Ft
    • Built 2002

    Last Sold Summary

    • 5% Below List Price
    • $244/SF
    • 8 Days On Market

    Current Estimated Value $530,721

    Last Listing Agent Julien Collet PINEYWOODS REALTY LLC

    708 Anna Hope Ln, Osprey, FL 34229
    • 995 Scherer Way, Osprey, FL 34229
      995 Scherer Way, Osprey, FL 34229
      /2

      Est $817,469

      Not Listed For Sale

      995 Scherer Way, Osprey, FL 34229

      • 4 Beds
      • 3 Baths
      • 2,933 Sq Ft
      • Built 2004
      995 Scherer Way, Osprey, FL 34229

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Ellen Ross BRIGHT REALTY

  • 659 Rivendell Blvd, Osprey, FL 34229
    659 Rivendell Blvd, Osprey, FL 34229
    /2

    $631,000

    Sold Apr 23, 2026

    659 Rivendell Blvd, Osprey, FL 34229

    • 3 Beds
    • 2.5 Baths
    • 2,292 Sq Ft
    • Built 2001

    Last Sold Summary

    • 7% Below List Price
    • $275/SF
    • 22 Days On Market

    Current Estimated Value $637,967

    Last Listing Agent Stephanie Church COLDWELL BANKER REALTY

    659 Rivendell Blvd, Osprey, FL 34229
    • 1353 Thornapple Dr, Osprey, FL 34229
      1353 Thornapple Dr, Osprey, FL 34229
      1353 Thornapple Dr, Osprey, FL 34229
      /37

      Est $596,542

      Not Listed For Sale

      1353 Thornapple Dr, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 2,173 Sq Ft
      • Built 2003
      1353 Thornapple Dr, Osprey, FL 34229

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • 5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229
    5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229
    /2

    $640,000

    Sold Jan 06, 2026

    5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,484 Sq Ft
    • Built 2004

    Last Sold Summary

    • 12% Below List Price
    • $258/SF
    • 130 Days On Market

    Current Estimated Value $630,620

    Last Listing Agent Robert Ruiz WILLIAM RAVEIS - FLORIDA LLC

    5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229
    • 919 Eagle Isle Ct, Osprey, FL 34229
      919 Eagle Isle Ct, Osprey, FL 34229
      /2

      Est $872,820

      Not Listed For Sale

      919 Eagle Isle Ct, Osprey, FL 34229

      • 4 Beds
      • 3 Baths
      • 2,614 Sq Ft
      • Built 2004
      919 Eagle Isle Ct, Osprey, FL 34229

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Ryan Skrzypkowski COLDWELL BANKER REALTY

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

    $1,300,000

    Sold Jul 22, 2026

    25 Sugar Mill Dr, Osprey, FL 34229

    • 3 Beds
    • 3.5 Baths
    • 3,066 Sq Ft
    • Built 1998

    Last Sold Summary

    • 23% Below List Price
    • $424/SF
    • 151 Days On Market

    Current Estimated Value $1,463,194

    Last Listing Agent Mark Lyda GENEROUS PROPERTY

    25 Sugar Mill Dr, Osprey, FL 34229

Showing Results 441 - 480, Page 12 of 18

Florida Sarasota County

Real Estate & Homes

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

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 © 2026 CoStar Group