Osprey, FL Homes

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  /46

  Est $1,023,352 Not Listed For Sale

  354 Tintoretto Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,494 Sq Ft
  • Built 1965

  354 Tintoretto Dr, Osprey, FL 34229

  Last Sold Summary

  • 3% Below List Price
  • $710/SF
  • 8 Days On Market

  Last Sold Price $1,060,000

  Last Listing Agent Denise Mattmuller PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /47

  $264,900

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft

  232 Woodland Dr, Osprey, FL 34229

  This condo has the 3 L's! Location Location Location! Located in the central area of Osprey making it an easy drive to area beaches, downtown Venice or Sarasota. Located about a half mile to the Inter Coastal, making for a great walking area on Casey Key. Located close to the well known Casey Key Fish House and Tiki Bar. Shopping and restaurants are all nearby! The location of this condo within

  Pat Williams PAT WILLIAMS REALTY, LLC

  232 Woodland Dr, Osprey, FL 34229
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  /2

  $625,000 Sold Feb 23, 2026

  804 Shadow Bay Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,279 Sq Ft
  • Built 2004

  Last Sold Summary

  • 5% Below List Price
  • $274/SF
  • 56 Days On Market

  Current Estimated Value $645,650

  Last Listing Agent Andrew Foltz PREFERRED SHORE LLC

  804 Shadow Bay Way, Osprey, FL 34229
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  /27

  Est $1,532,365 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

  • 4% Below List Price
  • $434/SF
  • 0 Days On Market

  Last Sold Price $1,590,000

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
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  /64

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  764 Sarabay Rd Unit 8, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Live the Florida dream on the water! Wake up to shimmering bay views, spend your days boating and fishing, and end every evening with breathtaking sunsets over Little Sarasota Bay, all from this rarely available, maintenance-free waterfront villa. In the exclusive Heron Bay Club, an intimate bayfront enclave of just 25 villas set across 10

  Michael Christo PREMIER SOTHEBYS INTL REALTY

  764 Sarabay Rd Unit 8, Osprey, FL 34229
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  /2

  $515,000 Sold Mar 10, 2026

  811 Shadow Bay Way, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,760 Sq Ft
  • Built 1999

  Last Sold Summary

  • 2% Below List Price
  • $293/SF
  • 2 Days On Market

  Current Estimated Value $529,039

  Last Listing Agent Wayne Cherry PROGRAM REALTY, LLC

  811 Shadow Bay Way, Osprey, FL 34229
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  /2

  Est $2,009,822 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

  • 20% Below List Price
  • $669/SF
  • 0 Days On Market

  Last Sold Price $2,500,000

  Last Listing Agent Rosalie Phillips Michael Saunders
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  /68

  $329,900 Open Sun 1PM - 3:30PM

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft

  4304 Expedition Way Unit 105, Osprey, FL 34229

  Spectacular water views from most windows in this immaculate, lightly used 3BR/2BA condo, built in 2018 and located in the gated community of Bay Street Villages. The popular Ibis floor plan offers an open-concept kitchen, dining, and great room with designer finishes, including white 42” cabinetry, light granite countertops, custom backsplash and stainless-steel appliances.Enjoy peaceful

  Tim Weller EXIT KING REALTY

  4304 Expedition Way Unit 105, Osprey, FL 34229
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  /2

  $896,148 Sold Apr 07, 2025

  280 Hidden Bay Dr Unit 301, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Built 2024

  Last Sold Summary

  • 5% Above List Price
  • $414/SF
  • 0 Days On Market

  Current Estimated Value $831,204

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 301, Osprey, FL 34229
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  /2

  Est $730,399 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

  • 5% Below List Price
  • $335/SF
  • 9 Days On Market

  Last Sold Price $772,000

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /2

  $650,000 Sold Nov 14, 2025

  866 Placid Lake Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,171 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Below List Price
  • $299/SF
  • 19 Days On Market

  Current Estimated Value $662,922

  Last Listing Agent Justin Brunswick KELLER WILLIAMS ON THE WATER S

  866 Placid Lake Dr, Osprey, FL 34229
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  /2

  Est $593,364 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

  • 48% Above List Price
  • $145/SF
  • 41 Days On Market

  Last Sold Price $400,000

  Last Listing Agent Michele Monteiro COLDWELL BANKER REALTY
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  /2

  $5,350,000 Sold Dec 08, 2025

  622 Bayshore Dr, Osprey, FL 34229

  • 6 Beds
  • 5 Baths
  • 4,893 Sq Ft
  • Built 2022

  Last Sold Summary

  • 21% Below List Price
  • $1,093/SF
  • 126 Days On Market

  Current Estimated Value $5,283,398

  Last Listing Agent Debra Pitell-Hauge MICHAEL SAUNDERS & COMPANY

  622 Bayshore Dr, Osprey, FL 34229
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  /47

  Est $819,255 Not Listed For Sale

  1440 Seafarer Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,644 Sq Ft
  • Built 1979

  1440 Seafarer Dr, Osprey, FL 34229

  Last Sold Summary

  • 3% Above List Price
  • $485/SF
  • 1 Day On Market

  Last Sold Price $797,000

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /2

  $160,000 Sold Dec 22, 2025

  191 Palm Air Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,376 Sq Ft
  • Built 1978

  Last Sold Summary

  • 29% Below List Price
  • $116/SF
  • 518 Days On Market

  Last Listing Agent John Alexander FINE PROPERTIES

  191 Palm Air Dr, Osprey, FL 34229
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  /42

  Est $875,213 Not Listed For Sale

  116 Bishopscourt Rd, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1996

  116 Bishopscourt Rd, Osprey, FL 34229

  Last Sold Summary

  • 6% Above List Price
  • $344/SF
  • 0 Days On Market

  Last Sold Price $825,000

  Last Listing Agent Mark Lyda GENEROUS PROPERTY
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  /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 $444,124

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

  1102 Jessie Harbor Dr, Osprey, FL 34229
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  /2

  Est $1,046,766 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

  • 16% Above List Price
  • $315/SF
  • 281 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Tina Timmons ROSEBAY INTERNATIONAL REALTY, INC
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  /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 $281,389

  Last Listing Agent Judi Cipollina COLDWELL BANKER REALTY

  4267 Expedition Way, Osprey, FL 34229
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  /11

  Est $2,095,919 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

  • 12% Below List Price
  • $630/SF

  Last Sold Price $2,375,000

  Last Listing Agent Mark Lyda GENEROUS PROPERTY
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  /2

  $807,000 Sold Apr 22, 2025

  124 Tina Island Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,112 Sq Ft
  • Built 1975

  Last Sold Summary

  • 31% Below List Price
  • $382/SF
  • 244 Days On Market

  Current Estimated Value $811,429

  Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

  124 Tina Island Dr, Osprey, FL 34229
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  /42

  Est $253,669 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

  • 11% Below List Price
  • $455/SF
  • 12 Days On Market

  Last Sold Price $285,000

  Last Listing Agent Tracey Fiedler DALTON WADE INC
• 

  /2

  $275,000 Sold Apr 11, 2025

  208 Pennsylvania Ave, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 900 Sq Ft
  • Built 1963

  Last Sold Summary

  • 8% Below List Price
  • $306/SF
  • 33 Days On Market

  Current Estimated Value $281,837

  Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

  208 Pennsylvania Ave, Osprey, FL 34229
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  /40

  Est $291,697 Not Listed For Sale

  437 Pennsylvania Ave, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 900 Sq Ft
  • Built 1952

  437 Pennsylvania Ave, Osprey, FL 34229

  Last Sold Summary

  • 17% Below List Price
  • $389/SF
  • 26 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Terri Fellows WATERSIDE REALTY LLC
• 

  /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 $664,712

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 603, Osprey, FL 34229
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  /65

  Est $2,034,973 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

  • 27% Above List Price
  • $405/SF
  • 73 Days On Market

  Last Sold Price $1,600,000

  Last Listing Agent Nelly Milicevic BRIGHT REALTY
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  /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 $140,434

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 19, Osprey, FL 34229
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  /6

  Not Listed For Sale

  50 W Bay St, Osprey, FL 34229

  • 8 Beds
  • Built 1917

  50 W Bay St, Osprey, FL 34229

  Last Sold Summary

  • $89/SF
  • 98 Days On Market

  Last Sold Price $590,000

  Last Listing Agent Marisa Marino BRIGHT REALTY
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  /2

  $875,000 Sold May 01, 2025

  851 E Bay St, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,329 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $376/SF
  • 8 Days On Market

  Current Estimated Value $863,715

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  851 E Bay St, Osprey, FL 34229
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  /2

  Est $588,994 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

  • 2% Below List Price
  • $260/SF
  • 133 Days On Market

  Last Sold Price $600,000

  Last Listing Agent Frank Zeckel COLDWELL BANKER REALTY
• 

  /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 $501,511

  Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

  1164 Beachcomber Ct Unit 19, Osprey, FL 34229
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  /43

  Est $120,742 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

  • 9% Below List Price
  • $225/SF
  • 2 Days On Market

  Last Sold Price $132,000

  Last Listing Agent Erik Dunigan CORNERSTONE R.E OF SW FL
• 

  /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 $842,202

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  678 Crane Prairie Way, Osprey, FL 34229
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  /72

  Est $240,669 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

  • 14% Below List Price
  • $229/SF
  • 79 Days On Market

  Last Sold Price $280,000

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC
• 

  /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 $2,211,758

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  370 Sugar Mill Dr, 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

  • $402/SF
  • 114 Days On Market

  Last Sold Price $875,000

  Last Listing Agent Daniel Jasmer FINE PROPERTIES
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  /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 $661,457

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  1212 Windward Dr, Osprey, FL 34229
• 

  /2

  Est $364,140 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

  • 9% Above List Price
  • $221/SF
  • 2 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY
• 

  /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 $145,931

  Last Listing Agent Carla Rayman Kidd COLDWELL BANKER REALTY

  107 Woodland Place Unit 107, Osprey, FL 34229
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  /93

  Est $1,884,969 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

  • 1% Below List Price
  • $459/SF
  • 4 Days On Market

  Last Sold Price $1,900,000

  Last Listing Agent Debra Forkan COLDWELL BANKER REALTY

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