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 $917,771

  Last Listing Agent Leonard Giarrano RE/MAX ALLIANCE GROUP

  3957 Waypoint Ave, Osprey, FL 34229
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  $1,600,000 Sold May 01, 2025

  916 MacEwen Dr, Osprey, FL 34229

  • 5 Beds
  • 7.5 Baths
  • 5,987 Sq Ft
  • Built 1991

  Last Sold Summary

  • 11% Below List Price
  • $267/SF
  • 1 Day On Market

  Current Estimated Value $1,659,872

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  916 MacEwen Dr, Osprey, FL 34229
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  $140,000 Sold May 02, 2025

  234 Patterson Ave, Osprey, FL 34229

  • 3 Beds
  • 1 Bath
  • 1,173 Sq Ft
  • Built 1979

  Last Sold Summary

  • 53% Below List Price
  • $119/SF
  • 9 Days On Market

  Current Estimated Value $198,982

  Last Listing Agent Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  234 Patterson 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 $250,242

  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 $431,332

  Last Listing Agent Peggy Lewis COLDWELL BANKER SARASOTA CENT.

  784 Sarabay Rd, Osprey, FL 34229
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  $875,585 Sold Mar 27, 2025

  280 Hidden Bay Dr Unit 403, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Above List Price
  • $452/SF
  • 13 Days On Market

  Current Estimated Value $812,680

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 403, 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 $872,101

  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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  $1,050,000 Sold Apr 16, 2025

  247 Keel Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,871 Sq Ft
  • Built 1979

  Last Sold Summary

  • 9% Below List Price
  • $366/SF
  • 70 Days On Market

  Current Estimated Value $1,009,239

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  247 Keel Way, 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 $1,843,181

  Last Listing Agent William Kelly THE REAL ESTATE STORE

  453 E MacEwen Dr, 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 $537,638

  Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

  827 Placid Lake Dr, Osprey, FL 34229
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  $925,000 Sold Apr 10, 2025

  280 Hidden Bay Dr Unit 401, Osprey, FL 34229

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

  Last Sold Summary

  • $427/SF
  • 31 Days On Market

  Current Estimated Value $875,834

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 401, 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 $790,668

  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 $1,734,198

  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 $639,960

  Last Listing Agent Linda Scheller COLDWELL BANKER REALTY

  236 Hidden Bay Dr Unit 301, Osprey, FL 34229
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  $780,000 Sold May 08, 2025

  779 Fordingbridge Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,154 Sq Ft
  • Built 2002

  Last Sold Summary

  • 1% Below List Price
  • $362/SF
  • 6 Days On Market

  Current Estimated Value $743,624

  Last Listing Agent Leonard Giarrano RE/MAX ALLIANCE GROUP

  779 Fordingbridge Way, 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 $1,142,686

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  1235 Yacht Harbor Dr, 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 $981,176

  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 $2,209,120

  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 $1,478,213

  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 $1,302,735

  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 $936,907

  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 $208,977

  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 $1,011,978

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

  385 N Point Rd Unit 903, Osprey, FL 34229
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  $340,000 Sold May 08, 2025

  294 Hidden Bay Dr Unit 103, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 2001

  Last Sold Summary

  • 20% Below List Price
  • $217/SF
  • 166 Days On Market

  Current Estimated Value $334,658

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  294 Hidden Bay Dr Unit 103, 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 $221,371

  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 $468,493

  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 $340,597

  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 $1,239,858

  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 $892,441

  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 $392,484

  Last Listing Agent Bill Garrison RE/MAX PALM

  117 Villa Dr Unit 117, Osprey, FL 34229
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  $1,051,025 Sold Apr 04, 2025

  280 Hidden Bay Dr Unit 502, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Above List Price
  • $543/SF
  • 2 Days On Market

  Current Estimated Value $937,792

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 502, 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 $743,472

  Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  162 Willow Bend Way, Osprey, FL 34229
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  $925,000 Sold Mar 25, 2025

  280 Hidden Bay Dr Unit 503, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  Last Sold Summary

  • $478/SF
  • 0 Days On Market

  Current Estimated Value $850,751

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 503, 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 $527,070

  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 $846,065

  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 $245,709

  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 $760,146

  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 $228,286

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  111 Woodland Place, Osprey, FL 34229

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