Recently Sold Homes in 34229

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  $635,000

  Sold Jan 29, 2026

  178 Willow Bend Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,889 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $336/SF
  • 8 Days On Market

  Current Estimated Value $624,073

  Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  178 Willow Bend Way, Osprey, FL 34229
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  /2

  $335,000

  Sold May 14, 2026

  291 Hidden Bay Dr Unit 102, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,479 Sq Ft
  • Built 2000

  Last Sold Summary

  • 16% Below List Price
  • $227/SF
  • 69 Days On Market

  Current Estimated Value $343,436

  Last Listing Agent Pat McMillan PREMIER SOTHEBY'S INTERNATIONAL REALTY

  291 Hidden Bay Dr Unit 102, Osprey, FL 34229
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  $1,285,000

  Sold Apr 08, 2026

  137 Osprey Point Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,303 Sq Ft
  • Built 1996

  Last Sold Summary

  • 10% Below List Price
  • $389/SF
  • 118 Days On Market

  Current Estimated Value $1,562,976

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  137 Osprey Point Dr, Osprey, FL 34229
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  $700,000

  Sold Oct 08, 2025

  826 Oak Briar Ln, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,589 Sq Ft
  • Built 2003

  Last Sold Summary

  • 10% Below List Price
  • $270/SF
  • 160 Days On Market

  Current Estimated Value $705,265

  Last Listing Agent Peter LaSalle PREFERRED SHORE LLC

  826 Oak Briar Ln, Osprey, FL 34229
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  /2

  $585,000

  Sold Mar 27, 2026

  584 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,151 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Below List Price
  • $272/SF
  • 18 Days On Market

  Current Estimated Value $575,857

  Last Listing Agent Jack Keller JACK KELLER INC

  584 Meadow Sweet Cir, Osprey, FL 34229
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  /2

  $260,000

  Sold Jan 23, 2026

  761 Pine Run Dr, Osprey, FL 34229

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

  Last Sold Summary

  • 7% Below List Price
  • $189/SF
  • 31 Days On Market

  Current Estimated Value $251,707

  Last Listing Agent Jeffrey Gaudette COLDWELL BANKER SARASOTA CENT.

  761 Pine Run Dr, Osprey, FL 34229
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  $2,925,000

  Sold Sep 23, 2025

  550 Dove Pointe, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 7,842 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $373/SF
  • 63 Days On Market

  Current Estimated Value $2,929,043

  Last Listing Agent Jennifer Linehan MICHAEL SAUNDERS & COMPANY

  550 Dove Pointe, Osprey, FL 34229
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  /2

  $280,000

  Sold Feb 04, 2026

  232 Explorer Dr Unit 15, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft
  • Built 2019

  Last Sold Summary

  • 15% Below List Price
  • $247/SF
  • 220 Days On Market

  Current Estimated Value $276,525

  Last Listing Agent Gary Hoskins COLDWELL BANKER REALTY

  232 Explorer Dr Unit 15, Osprey, FL 34229
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  $335,000

  Sold Mar 27, 2026

  172 Explorer Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,449 Sq Ft
  • Built 2016

  Last Sold Summary

  • 4% Below List Price
  • $231/SF
  • 3 Days On Market

  Current Estimated Value $330,203

  Last Listing Agent Ashley Wallace COLDWELL BANKER REALTY

  172 Explorer Dr, Osprey, FL 34229
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  /2

  $995,000

  Sold Mar 05, 2026

  105 Turquoise Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,606 Sq Ft
  • Built 2001

  Last Sold Summary

  • $382/SF
  • 162 Days On Market

  Current Estimated Value $981,369

  Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  105 Turquoise Ln, Osprey, FL 34229
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  /2

  $285,900

  Sold Aug 17, 2026

  120 Woodland Place Unit 120, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $216/SF
  • 5 Days On Market

  Current Estimated Value $210,871

  Last Listing Agent Kim Kruysman EXP REALTY LLC

  120 Woodland Place Unit 120, Osprey, FL 34229
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  $1,700,000

  Sold Jul 17, 2026

  401 Walls Way, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,387 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $388/SF
  • 138 Days On Market

  Current Estimated Value $1,751,348

  Last Listing Agent Andrea Stultz ENGEL + VOELKERS SARASOTA

  401 Walls Way, Osprey, FL 34229
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  /2

  $660,000

  Sold Aug 26, 2025

  463 Park Trace Blvd, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,153 Sq Ft
  • Built 2002

  Last Sold Summary

  • 12% Below List Price
  • $307/SF
  • 63 Days On Market

  Current Estimated Value $662,722

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

  463 Park Trace Blvd, Osprey, FL 34229
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  $540,000

  Sold Aug 07, 2026

  523 Oak Bay Dr, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 2,399 Sq Ft
  • Built 1998

  Last Sold Summary

  • $225/SF
  • 20 Days On Market

  Current Estimated Value $538,623

  Last Listing Agent Karie Backman KELLER WILLIAMS ON THE WATER S

  523 Oak Bay Dr, Osprey, FL 34229
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  $750,000

  Sold Dec 30, 2025

  523 Habitat Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,314 Sq Ft
  • Built 2003

  Last Sold Summary

  • 5% Below List Price
  • $324/SF
  • 122 Days On Market

  Current Estimated Value $750,511

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  523 Habitat Blvd, Osprey, FL 34229
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  $799,000

  Sold Mar 09, 2026

  529 Habitat Blvd, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,617 Sq Ft
  • Built 2003

  Last Sold Summary

  • $305/SF
  • 2 Days On Market

  Current Estimated Value $794,572

  Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  529 Habitat Blvd, Osprey, FL 34229
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  $550,000

  Sold Mar 23, 2026

  510 Latitude Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,298 Sq Ft
  • Built 2004

  Last Sold Summary

  • 13% Below List Price
  • $239/SF
  • 125 Days On Market

  Current Estimated Value $561,908

  Last Listing Agent Marisa Marino BRIGHT REALTY

  510 Latitude Ln, Osprey, FL 34229
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  $715,000

  Sold Mar 17, 2026

  319 Park Trace Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,551 Sq Ft
  • Built 2000

  Last Sold Summary

  • 5% Below List Price
  • $280/SF
  • 33 Days On Market

  Current Estimated Value $719,118

  Last Listing Agent Megan George PREMIER SOTHEBYS INTL REALTY

  319 Park Trace Blvd, Osprey, FL 34229
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  $362,500

  Sold Feb 23, 2026

  291 Hidden Bay Dr Unit 101, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,599 Sq Ft
  • Built 2000

  Last Sold Summary

  • 9% Below List Price
  • $227/SF
  • 58 Days On Market

  Current Estimated Value $357,712

  Last Listing Agent Stephanie Ham PARADISE EXCLUSIVE REAL ESTATE

  291 Hidden Bay Dr Unit 101, Osprey, FL 34229
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  $2,300,000

  Sold Apr 06, 2026

  896 MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 4,858 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $473/SF
  • 35 Days On Market

  Current Estimated Value $2,270,102

  Last Listing Agent Marisa Marino BRIGHT REALTY

  896 MacEwen Dr, Osprey, FL 34229
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  $2,315,000

  Sold Oct 30, 2025

  112 Osprey Point Dr, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 8,635 Sq Ft
  • Built 1989

  Last Sold Summary

  • 41% Below List Price
  • $268/SF
  • 156 Days On Market

  Current Estimated Value $3,030,096

  Last Listing Agent Kara Money KARA MONEY LLC

  112 Osprey Point Dr, Osprey, FL 34229
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  /2

  $665,000

  Sold Nov 06, 2025

  563 Pine Ranch Rd E, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,346 Sq Ft
  • Built 1997

  Last Sold Summary

  • 1% Below List Price
  • $283/SF
  • 5 Days On Market

  Current Estimated Value $661,409

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

  563 Pine Ranch Rd E, Osprey, FL 34229
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  $1,500,000

  Sold Sep 19, 2025

  462 E MacEwen Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,611 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Below List Price
  • $574/SF
  • 29 Days On Market

  Current Estimated Value $1,472,751

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  462 E MacEwen Dr, Osprey, FL 34229
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  /2

  $166,000

  Sold May 21, 2026

  238 Palm Air Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1986

  Last Sold Summary

  • 8% Below List Price
  • $144/SF
  • 15 Days On Market

  Last Listing Agent Susan Retzke RE/MAX PALM

  238 Palm Air Dr, Osprey, FL 34229
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  $654,000

  Sold Apr 16, 2026

  1303 Thornapple Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Below List Price
  • $339/SF
  • 93 Days On Market

  Current Estimated Value $643,235

  Last Listing Agent Michael A Martino KELLER WILLIAMS ON THE WATER S

  1303 Thornapple Dr, Osprey, FL 34229
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  /2

  $241,000

  Sold May 28, 2026

  0 Sarabay Rd, Osprey, FL 34229

  • Land
  • 13,939 Sq Ft
  • $753,125 per Acre

  Last Sold Summary

  • 7% Above List Price
  • 3 Days On Market

  Last Listing Agent Cheri Castro MICHAEL SAUNDERS & COMPANY

  0 Sarabay Rd, Osprey, FL 34229
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  /2

  $925,000

  Sold Jul 15, 2026

  1602 Southbay Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 2,980 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $310/SF
  • 198 Days On Market

  Current Estimated Value $1,012,115

  Last Listing Agent Thomas Kiessling COMPASS FLORIDA LLC

  1602 Southbay Dr, Osprey, FL 34229
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  /2

  $520,000

  Sold Jun 17, 2026

  1337 Copperwood Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,172 Sq Ft
  • Built 2004

  Last Sold Summary

  • 13% Below List Price
  • $239/SF
  • 199 Days On Market

  Current Estimated Value $536,472

  Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1337 Copperwood Dr, Osprey, FL 34229
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  /2

  $570,000

  Sold Apr 03, 2026

  51 Webb St, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,130 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $268/SF
  • 6 Days On Market

  Current Estimated Value $572,485

  Last Listing Agent Marina Myers FINE PROPERTIES

  51 Webb St, Osprey, FL 34229
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  $1,700,000

  Sold Sep 18, 2025

  898 MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 4 Baths
  • 4,132 Sq Ft
  • Built 1997

  Last Sold Summary

  • 13% Below List Price
  • $411/SF
  • 0 Days On Market

  Current Estimated Value $1,796,770

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  898 MacEwen Dr, Osprey, FL 34229
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  /2

  $329,000

  Sold Jan 14, 2026

  85 Navigation Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $230/SF
  • 8 Days On Market

  Current Estimated Value $317,399

  Last Listing Agent Kate Kwiecinski COLDWELL BANKER REALTY

  85 Navigation Cir, Osprey, FL 34229
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  /2

  $155,000

  Sold Nov 26, 2025

  170 Edgewood Dr, Osprey, FL 34229

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

  Last Sold Summary

  • 6% Below List Price
  • $162/SF
  • 132 Days On Market

  Last Listing Agent Roberta Burish KW SUNCOAST

  170 Edgewood Dr, Osprey, FL 34229
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  /2

  $3,900,000

  Sold Aug 27, 2025

  426 N Casey Key Rd, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft
  • Built 1992

  Last Sold Summary

  • 20% Below List Price
  • $2,079/SF
  • 657 Days On Market

  Current Estimated Value $3,542,917

  Last Listing Agent Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  426 N Casey Key Rd, Osprey, FL 34229
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  /2

  $3,500,000

  Sold Dec 17, 2025

  431 Yacht Harbor Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 3,006 Sq Ft
  • Built 1979

  Last Sold Summary

  • 19% Below List Price
  • $1,164/SF
  • 11 Days On Market

  Current Estimated Value $3,489,704

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  431 Yacht Harbor Dr, Osprey, FL 34229
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  /2

  $535,000

  Sold Jun 03, 2026

  242 Hidden Bay Dr Unit 603, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,932 Sq Ft
  • Built 1999

  Last Sold Summary

  • 9% Below List Price
  • $277/SF
  • 100 Days On Market

  Current Estimated Value $539,177

  Last Listing Agent Susan Retzke RE/MAX PALM

  242 Hidden Bay Dr Unit 603, Osprey, FL 34229
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  /2

  $1,105,000

  Sold Jul 17, 2026

  272 Four Knot Ln, Osprey, FL 34229

  • 5 Beds
  • 3 Baths
  • 2,723 Sq Ft
  • Built 1978

  Last Sold Summary

  • 1% Above List Price
  • $406/SF
  • 2 Days On Market

  Current Estimated Value $1,085,870

  Last Listing Agent Andrew Peterson EVOLVE REAL ESTATE

  272 Four Knot Ln, Osprey, FL 34229
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  /2

  $530,000

  Sold Jun 11, 2026

  1116 Beachcomber Ct Unit 3, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $260/SF
  • 31 Days On Market

  Current Estimated Value $527,441

  Last Listing Agent Christine Green COLDWELL BANKER REALTY

  1116 Beachcomber Ct Unit 3, Osprey, FL 34229
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  /2

  $1,265,000

  Sold Jun 01, 2026

  1471 Shoal Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,798 Sq Ft
  • Built 1985

  Last Sold Summary

  • 16% Below List Price
  • $452/SF
  • 47 Days On Market

  Current Estimated Value $1,270,728

  Last Listing Agent Lauren Doyle DALTON WADE INC

  1471 Shoal Way, Osprey, FL 34229
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  $1,400,000

  Pending

  • 3 Beds
  • 3.5 Baths
  • 2,939 Sq Ft

  486 Yacht Harbor Dr, Osprey, FL 34229

  Welcome to this exceptional Southbay home featuring the rare and highly desirable 3 car garage! From the moment you step inside, you’ll appreciate the elegant finishes, soaring tray and vaulted ceilings with crown molding, and beautiful travertine flooring throughout. The entry opens to the spacious dining area and leads into the oversized Greatroom which flows seamlessly into the chef-inspired

  Pat Williams PAT WILLIAMS REALTY, LLC

  486 Yacht Harbor Dr, Osprey, FL 34229
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  /2

  $164,000

  Sold May 14, 2026

  200 Woodland Dr Unit 200, Osprey, FL 34229

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft
  • Built 1980

  Last Sold Summary

  • 6% Below List Price
  • $190/SF
  • 45 Days On Market

  Current Estimated Value $168,678

  Last Listing Agent Kathleen Griffin MICHAEL SAUNDERS & COMPANY

  200 Woodland Dr Unit 200, Osprey, FL 34229

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