Recently Sold Homes in 34229

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  $900,000 Sold Jan 16, 2026

  3957 Waypoint Ave, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,328 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $387/SF
  • 35 Days On Market

  Current Estimated Value $934,774

  Last Listing Agent Leonard Giarrano RE/MAX ALLIANCE GROUP

  3957 Waypoint Ave, Osprey, FL 34229
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  $265,000 Sold May 15, 2025

  360 Pine Run Dr Unit 360, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,379 Sq Ft
  • Built 1973

  Last Sold Summary

  • 16% Below List Price
  • $192/SF
  • 74 Days On Market

  Current Estimated Value $246,784

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  360 Pine Run Dr Unit 360, Osprey, FL 34229
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  $452,500 Sold Aug 29, 2025

  784 Sarabay Rd, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 1981

  Last Sold Summary

  • 38% Below List Price
  • $287/SF
  • 257 Days On Market

  Current Estimated Value $423,422

  Last Listing Agent Peggy Lewis COLDWELL BANKER SARASOTA CENT.

  784 Sarabay Rd, Osprey, FL 34229
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  $865,000 Sold Feb 10, 2026

  38 W Bay St, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,124 Sq Ft
  • Built 1994

  Last Sold Summary

  • 6% Below List Price
  • $407/SF
  • 107 Days On Market

  Current Estimated Value $857,516

  Last Listing Agent Mitch Helmuth HARRY ROBBINS ASSOC INC

  38 W Bay St, Osprey, FL 34229
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  $75,000 Sold Dec 12, 2025

  570 Blackburn Point Rd Unit 2, Osprey, FL 34229

  • Built 2006

  Last Sold Summary

  • 5% Below List Price
  • 17 Days On Market

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 2, Osprey, FL 34229
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  $1,850,000 Sold Jan 22, 2026

  453 E MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,191 Sq Ft
  • Built 1999

  Last Sold Summary

  • 8% Below List Price
  • $441/SF
  • 19 Days On Market

  Current Estimated Value $1,836,267

  Last Listing Agent William Kelly THE REAL ESTATE STORE

  453 E MacEwen Dr, Osprey, FL 34229
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  $669,000 Sold Apr 07, 2026

  146 Willow Bend Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,540 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Below List Price
  • $263/SF
  • 26 Days On Market

  Current Estimated Value $699,833

  Last Listing Agent Maria Rocha KELLER WILLIAMS ON THE WATER S

  146 Willow Bend Way, Osprey, FL 34229
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  $480,000 Sold Mar 18, 2026

  827 Placid Lake Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,875 Sq Ft
  • Built 2002

  Last Sold Summary

  • 16% Below List Price
  • $256/SF
  • 202 Days On Market

  Current Estimated Value $496,806

  Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

  827 Placid Lake Dr, Osprey, FL 34229
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  $1,025,000 Sold Apr 24, 2026

  1218 Yacht Harbor Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,297 Sq Ft
  • Built 1980

  Last Sold Summary

  • 15% Below List Price
  • $311/SF
  • 203 Days On Market

  Current Estimated Value $1,061,092

  Last Listing Agent Karie Backman KELLER WILLIAMS ON THE WATER S

  1218 Yacht Harbor Dr, Osprey, FL 34229
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  $505,025 Sold Mar 26, 2026

  570 Crane Prairie Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,298 Sq Ft
  • Built 2005

  Last Sold Summary

  • 1% Above List Price
  • $220/SF
  • 2 Days On Market

  Current Estimated Value $499,668

  Last Listing Agent Mickey Schweitzer MS REALTY MICKEY SCHWEITZER & ASSOCIATES LLC

  570 Crane Prairie Way, Osprey, FL 34229
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  $727,500 Sold Feb 12, 2026

  260 Hidden Bay Dr Unit B 305, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,168 Sq Ft
  • Built 2019

  Last Sold Summary

  • 17% Below List Price
  • $336/SF
  • 257 Days On Market

  Current Estimated Value $743,234

  Last Listing Agent Cathy Rustin FIRST LIGHT REAL ESTATE

  260 Hidden Bay Dr Unit B 305, Osprey, FL 34229
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  $1,750,000 Sold Oct 27, 2025

  627 N MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 4.5 Baths
  • 3,857 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $454/SF
  • 1 Day On Market

  Current Estimated Value $1,748,618

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  627 N MacEwen Dr, Osprey, FL 34229
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  $650,000 Sold Jul 03, 2025

  236 Hidden Bay Dr Unit 301, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1997

  Last Sold Summary

  • 13% Below List Price
  • $310/SF
  • 246 Days On Market

  Current Estimated Value $639,169

  Last Listing Agent Linda Scheller COLDWELL BANKER REALTY

  236 Hidden Bay Dr Unit 301, Osprey, FL 34229
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  $1,495,000 Sold Apr 14, 2026

  554 Dove Pointe, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,501 Sq Ft
  • Built 2002

  Last Sold Summary

  • $427/SF
  • 2 Days On Market

  Current Estimated Value $1,552,512

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  554 Dove Pointe, Osprey, FL 34229
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  $163,000 Sold Mar 06, 2026

  334 Tropic Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft
  • Built 1978

  Last Sold Summary

  • 7% Below List Price
  • $143/SF
  • 2 Days On Market

  Last Listing Agent Laura Guess-Fox COLDWELL BANKER REALTY

  334 Tropic Dr, Osprey, FL 34229
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  $1,065,000 Sold Feb 20, 2026

  1235 Yacht Harbor Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,698 Sq Ft
  • Built 1984

  Last Sold Summary

  • 9% Below List Price
  • $395/SF
  • 30 Days On Market

  Current Estimated Value $1,072,229

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  1235 Yacht Harbor Dr, Osprey, FL 34229
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  $4,000,000 Sold Apr 09, 2026

  854 N Casey Key Rd, Osprey, FL 34229

  • 4 Beds
  • 4 Baths
  • 3,462 Sq Ft
  • Built 1975

  Last Sold Summary

  • 16% Below List Price
  • $1,155/SF
  • 27 Days On Market

  Last Listing Agent Charles Ruck POTTER TRINITY

  854 N Casey Key Rd, Osprey, FL 34229
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  $155,000 Sold Apr 14, 2026

  316 Tropic Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,151 Sq Ft
  • Built 1979

  Last Sold Summary

  • 16% Below List Price
  • $135/SF
  • 36 Days On Market

  Last Listing Agent Karen Geiger COLDWELL BANKER SARASOTA CENT.

  316 Tropic Dr, Osprey, FL 34229
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  $362,500 Sold Apr 09, 2026

  124 Revolution Way, Osprey, FL 34229

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

  Last Sold Summary

  • 9% Below List Price
  • $230/SF
  • 47 Days On Market

  Current Estimated Value $385,075

  Last Listing Agent James Briley COLDWELL BANKER REALTY

  124 Revolution Way, Osprey, FL 34229
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  $1,050,000 Sold Jul 22, 2025

  142 Dory Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,531 Sq Ft
  • Built 1984

  Last Sold Summary

  • 12% Below List Price
  • $415/SF
  • 32 Days On Market

  Current Estimated Value $1,002,108

  Last Listing Agent Sharon Lewis GOLF & BAY PROPERTIES LLC

  142 Dory Ln, Osprey, FL 34229
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  $2,100,000 Sold Jan 30, 2026

  889 MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 4 Baths
  • 3,235 Sq Ft
  • Built 1994

  Last Sold Summary

  • 9% Below List Price
  • $649/SF
  • 41 Days On Market

  Current Estimated Value $2,055,629

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  889 MacEwen Dr, Osprey, FL 34229
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  $1,405,000 Sold Jul 11, 2025

  282 Shell Midden Ct, Osprey, FL 34229

  • 3 Beds
  • 4.5 Baths
  • 3,699 Sq Ft
  • Built 1992

  Last Sold Summary

  • 17% Below List Price
  • $380/SF
  • 128 Days On Market

  Current Estimated Value $1,401,689

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  282 Shell Midden Ct, Osprey, FL 34229
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  $1,330,000 Sold Jan 07, 2026

  401 N Point Rd Unit 901, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft
  • Built 2003

  Last Sold Summary

  • 24% Below List Price
  • $513/SF
  • 764 Days On Market

  Current Estimated Value $1,294,963

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 901, Osprey, FL 34229
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  $962,500 Sold Aug 07, 2025

  742 Shadow Bay Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,321 Sq Ft
  • Built 2002

  Last Sold Summary

  • 12% Below List Price
  • $290/SF
  • 115 Days On Market

  Current Estimated Value $958,576

  Last Listing Agent Reeny Kaney RE/MAX ALLIANCE GROUP

  742 Shadow Bay Way, Osprey, FL 34229
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  $210,000 Sold Oct 22, 2025

  480 Blackburn Point Rd Unit 4, Osprey, FL 34229

  • Built 2006

  Last Sold Summary

  • 7% Below List Price
  • 5 Days On Market

  Current Estimated Value $211,163

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  480 Blackburn Point Rd Unit 4, Osprey, FL 34229
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  $980,000 Sold Dec 09, 2025

  385 N Point Rd Unit 903, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft
  • Built 2000

  Last Sold Summary

  • 11% Below List Price
  • $353/SF
  • 41 Days On Market

  Current Estimated Value $999,976

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

  385 N Point Rd Unit 903, Osprey, FL 34229
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  $235,000 Sold Jun 13, 2025

  109 Woodland Place, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,223 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $192/SF
  • 144 Days On Market

  Current Estimated Value $217,992

  Last Listing Agent Derek Edwards KELLER WILLIAMS ON THE WATER S

  109 Woodland Place, Osprey, FL 34229
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  $480,000 Sold May 14, 2025

  564 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,808 Sq Ft
  • Built 2003

  Last Sold Summary

  • 15% Below List Price
  • $265/SF
  • 57 Days On Market

  Current Estimated Value $490,194

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

  564 Meadow Sweet Cir, Osprey, FL 34229
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  $350,000 Sold Oct 16, 2025

  240 Patterson Ave, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,360 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $257/SF
  • 157 Days On Market

  Current Estimated Value $345,874

  Last Listing Agent Janice Melzer Langa COLDWELL BANKER REALTY

  240 Patterson Ave, Osprey, FL 34229
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  $1,285,000 Sold Jun 30, 2025

  393 N Point Rd Unit 801, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,029 Sq Ft
  • Built 2001

  Last Sold Summary

  • 22% Below List Price
  • $424/SF
  • 204 Days On Market

  Current Estimated Value $1,230,624

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  393 N Point Rd Unit 801, Osprey, FL 34229
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  $904,900 Sold May 30, 2025

  336 Pine Ranch Rd E, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,705 Sq Ft
  • Built 1989

  Last Sold Summary

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

  Current Estimated Value $933,737

  Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC

  336 Pine Ranch Rd E, Osprey, FL 34229
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  $430,000 Sold Aug 01, 2025

  117 Villa Dr Unit 117, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • Built 1967

  Last Sold Summary

  • 22% Below List Price
  • $305/SF
  • 244 Days On Market

  Current Estimated Value $414,120

  Last Listing Agent Bill Garrison RE/MAX PALM

  117 Villa Dr Unit 117, Osprey, FL 34229
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  $689,000 Sold Mar 06, 2026

  162 Willow Bend Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,661 Sq Ft
  • Built 2004

  Last Sold Summary

  • $259/SF
  • 4 Days On Market

  Current Estimated Value $690,339

  Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  162 Willow Bend Way, Osprey, FL 34229
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  $525,000 Sold Dec 04, 2025

  1313 Thornapple Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,082 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $252/SF
  • 8 Days On Market

  Current Estimated Value $530,658

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1313 Thornapple Dr, Osprey, FL 34229
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  $765,000 Sold Jan 30, 2026

  385 N Point Rd Unit 404, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft
  • Built 2000

  Last Sold Summary

  • 17% Below List Price
  • $275/SF
  • 142 Days On Market

  Current Estimated Value $776,645

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 404, Osprey, FL 34229
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  $175,000 Sold Feb 23, 2026

  216 Glenwood Ave, Osprey, FL 34229

  • 2 Beds
  • 1 Bath
  • 732 Sq Ft
  • Built 1989

  Last Sold Summary

  • 30% Below List Price
  • $239/SF
  • 64 Days On Market

  Current Estimated Value $209,338

  Last Listing Agent Kristen Wheat COMPASS FLORIDA LLC

  216 Glenwood Ave, Osprey, FL 34229
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  $760,000 Sold Jul 16, 2025

  790 Shadow Bay Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,091 Sq Ft
  • Built 2002

  Last Sold Summary

  • 9% Below List Price
  • $246/SF
  • 158 Days On Market

  Current Estimated Value $776,902

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  790 Shadow Bay Way, Osprey, FL 34229
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  $227,000 Sold Dec 15, 2025

  111 Woodland Place, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Below List Price
  • $172/SF
  • 81 Days On Market

  Current Estimated Value $225,141

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  111 Woodland Place, Osprey, FL 34229
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  $835,000 Sold May 21, 2025

  14021 Bellagio Way Unit 410, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 2,214 Sq Ft
  • Built 2006

  Last Sold Summary

  • 12% Below List Price
  • $377/SF
  • 42 Days On Market

  Current Estimated Value $790,945

  Last Listing Agent Adam Waxler UKEEPCOMMISSION REAL ESTATE

  14021 Bellagio Way Unit 410, Osprey, FL 34229
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  $137,000 Sold Apr 17, 2026

  214 Palm Air Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $143/SF
  • 1 Day On Market

  Last Listing Agent Garrett Sedlacek KELLER WILLIAMS ON THE WATER S

  214 Palm Air Dr, Osprey, FL 34229

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