Recently Sold Homes in 34229

/2
$625,000 Sold Oct 10, 2025

644 Rivendell Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,298 Sq Ft
- Built 2001
Last Sold Summary
- 16% Below List Price
- $272/SF
- 260 Days On Market
Current Estimated Value $629,092

Last Listing Agent Veronica Manes MICHAEL SAUNDERS & COMPANY

644 Rivendell Blvd, Osprey, FL 34229
/2
$675,000 Sold Jan 21, 2026

409 N Point Rd Unit 501, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
- Built 2004
Last Sold Summary
- 36% Below List Price
- $260/SF
- 575 Days On Market
Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

409 N Point Rd Unit 501, Osprey, FL 34229
/2
$1,400,000 Sold May 07, 2025

378 MacEwen Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 3,094 Sq Ft
- Built 1997
Last Sold Summary
- 7% Below List Price
- $452/SF
- 0 Days On Market
Current Estimated Value $1,403,414

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

378 MacEwen Dr, Osprey, FL 34229
/2
$26,000 Sold Apr 16, 2025

570 Blackburn Point Rd Unit 17, Osprey, FL 34229
Last Sold Summary
- 7% Below List Price
- 24 Days On Market
Current Estimated Value $34,584

Last Listing Agent Linda Williams GULF SHORES REALTY

570 Blackburn Point Rd Unit 17, Osprey, FL 34229
/2
$237,000 Sold Mar 31, 2025

14 Old Venice Rd, Osprey, FL 34229
- Land
- 0.97 Acre
- $244,330 per Acre
Last Sold Summary
- 12% Below List Price
- 34 Days On Market
Current Estimated Value $273,877

Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

14 Old Venice Rd, Osprey, FL 34229
/2
$744,800 Sold Apr 24, 2025

448 Park Trace Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,060 Sq Ft
- Built 2002
Last Sold Summary
- 22% Below List Price
- $243/SF
- 145 Days On Market
Current Estimated Value $776,815

Last Listing Agent Toni Zarghami KW COASTAL LIVING III

448 Park Trace Blvd, Osprey, FL 34229
/2
$3,525,000 Sold Jun 06, 2025

275 Lookout Point Dr, Osprey, FL 34229
- 5 Beds
- 5 Baths
- 5,279 Sq Ft
- Built 2007
Last Sold Summary
- 26% Below List Price
- $668/SF
- 124 Days On Market
Current Estimated Value $3,485,999

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

275 Lookout Point Dr, Osprey, FL 34229
/2
$2,000,000 Sold Apr 21, 2025

1862 Island Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,598 Sq Ft
- Built 1982
Last Sold Summary
- 18% Below List Price
- $556/SF
- 76 Days On Market
Current Estimated Value $1,957,127

Last Listing Agent Nancy Endara PREMIER SOTHEBY'S INTERNATIONAL REALTY

1862 Island Way, 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
Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

447 Oak Point Rd, Osprey, FL 34229
/2
$1,350,000 Sold Mar 28, 2025

409 N Point Rd Unit 704, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
- Built 2004
Last Sold Summary
- 7% Below List Price
- $486/SF
- 11 Days On Market
Current Estimated Value $1,308,928

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

409 N Point Rd Unit 704, Osprey, FL 34229
/2
$318,000 Sold Apr 30, 2025

115 Villa Dr Unit 115, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,411 Sq Ft
- Built 1972
Last Sold Summary
- 16% Below List Price
- $225/SF
- 125 Days On Market
Current Estimated Value $311,864

Last Listing Agent EJ Stukenborg KELLER WILLIAMS ON THE WATER S

115 Villa Dr Unit 115, Osprey, FL 34229
/2
$1,855,000 Sold Feb 26, 2025

533 N MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 4.5 Baths
- 3,794 Sq Ft
- Built 1999
Last Sold Summary
- 4% Below List Price
- $489/SF
- 9 Days On Market
Current Estimated Value $1,814,893

Last Listing Agent Mark Lyda GENEROUS PROPERTY

533 N MacEwen Dr, Osprey, FL 34229
/2
$999,000 Sold Mar 21, 2025

505 S Shore Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,301 Sq Ft
- Built 1980
Last Sold Summary
- 3% Below List Price
- $434/SF
- 16 Days On Market
Current Estimated Value $1,010,369

Last Listing Agent Nancy Jordan COLDWELL BANKER REALTY

505 S Shore Dr, Osprey, FL 34229
/2
$1,150,000 Sold May 28, 2025

327 Sea Anchor Dr, Osprey, FL 34229
- 2 Beds
- 3 Baths
- 2,521 Sq Ft
- Built 1981
Last Sold Summary
- 7% Below List Price
- $456/SF
- 20 Days On Market
Current Estimated Value $1,132,607

Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

327 Sea Anchor Dr, Osprey, FL 34229
/2
$640,000 Sold Jun 20, 2025

455 Park Trace Blvd, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,590 Sq Ft
- Built 1999
Last Sold Summary
- 15% Below List Price
- $247/SF
- 119 Days On Market
Current Estimated Value $653,851

Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

455 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
Last Listing Agent Ryan Skrzypkowski COLDWELL BANKER REALTY

392 Park Trace Blvd, Osprey, FL 34229
/2
$85,000 Sold May 23, 2025

199 Palm Air Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Built 1978
Last Sold Summary
- 15% Below List Price
- $89/SF
- 87 Days On Market
Last Listing Agent Allison Bollero KELLER WILLIAMS ISLAND LIFE REAL ESTATE

199 Palm Air Dr, Osprey, FL 34229
/66
$155,000 Sold May 15, 2025

767 Pine Run Dr, Osprey, FL 34229
- 1 Bed
- 1 Bath
- 736 Sq Ft
- Built 1973
Last Sold Summary
- $211/SF
- 4 Days On Market
Current Estimated Value $164,075

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

767 Pine Run Dr, Osprey, FL 34229
/2
$795,000 Sold Mar 21, 2025

280 Hidden Bay Dr Unit 304, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,166 Sq Ft
- Built 2023
Last Sold Summary
- $367/SF
- 0 Days On Market
Current Estimated Value $815,629

Last Listing Agent Bob Morris SVN COMMERCIAL ADVISORY GROUP

280 Hidden Bay Dr Unit 304, 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
Last Listing Agent Courtney Green PREMIER SOTHEBYS INTL REALTY

1049 N Casey Key Rd, Osprey, FL 34229
/2
$625,000 Sold Jul 26, 2025

695 Rivendell Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,256 Sq Ft
- Built 2001
Last Sold Summary
- 4% Below List Price
- $277/SF
- 1 Day On Market
Current Estimated Value $628,808

Last Listing Agent Dan Henson DALTON WADE INC

695 Rivendell Blvd, Osprey, FL 34229
/2
$559,500 Sold Apr 04, 2025

1219 Chalet Ct, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,165 Sq Ft
- Built 2004
Last Sold Summary
- 4% Below List Price
- $258/SF
- 56 Days On Market
Current Estimated Value $558,989

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1219 Chalet Ct, Osprey, FL 34229
/2
$1,197,000 Sold May 30, 2025

223 Saint James Park, Osprey, FL 34229
- 3 Beds
- 5 Baths
- 3,321 Sq Ft
- Built 1991
Last Sold Summary
- 8% Below List Price
- $360/SF
- 20 Days On Market
Current Estimated Value $1,185,277

Last Listing Agent John Hockenberry RE/MAX ALLIANCE GROUP

223 Saint James Park, 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
Last Listing Agent Julien Collet AGILE GROUP REALTY

708 Anna Hope Ln, Osprey, FL 34229
/62
$560,000 Sold May 29, 2025

221 Sorrento Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,935 Sq Ft
- Built 1984
Last Sold Summary
- 10% Below List Price
- $289/SF
- 68 Days On Market
Current Estimated Value $570,335

Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

221 Sorrento Dr, 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
Last Listing Agent Robert Ruiz WILLIAM RAVEIS REAL ESTATE

5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229
/2
$640,000 Sold Jun 04, 2025

519 Habitat Blvd, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,234 Sq Ft
- Built 2003
Last Sold Summary
- 3% Below List Price
- $286/SF
- 15 Days On Market
Current Estimated Value $633,680

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

519 Habitat Blvd, Osprey, FL 34229
/2
$656,000 Sold Feb 21, 2025

1109 Scherer Way, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,125 Sq Ft
- Built 2002
Last Sold Summary
- 6% Below List Price
- $309/SF
- 61 Days On Market
Current Estimated Value $644,250

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1109 Scherer Way, Osprey, FL 34229
/2
$324,000 Sold Mar 28, 2025

76 Explorer Dr Unit 104, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
- Built 2017
Last Sold Summary
- 7% Below List Price
- $227/SF
- 34 Days On Market
Current Estimated Value $319,642

Last Listing Agent Pan Steele, GRI COLDWELL BANKER REALTY

76 Explorer Dr Unit 104, Osprey, FL 34229
/2
$910,000 Sold Nov 19, 2025

766 Shadow Bay Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,438 Sq Ft
- Built 1998
Last Sold Summary
- 9% Below List Price
- $265/SF
- 132 Days On Market
Last Listing Agent Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.

766 Shadow Bay Way, Osprey, FL 34229
/2
$788,000 Sold Jun 27, 2025

521 Habitat Blvd, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,266 Sq Ft
- Built 2003
Last Sold Summary
- 1% Below List Price
- $348/SF
- 10 Days On Market
Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

521 Habitat Blvd, Osprey, FL 34229
/2
$325,000 Sold Jul 24, 2025

4236 Expedition Way Unit 106, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
- Built 2016
Last Sold Summary
- 10% Below List Price
- $213/SF
- 90 Days On Market
Current Estimated Value $323,587

Last Listing Agent Susan Honsberger RE/MAX ALLIANCE GROUP

4236 Expedition Way Unit 106, Osprey, FL 34229
/2
$500,000 Sold Mar 21, 2025

629 Oak Bay Dr, Osprey, FL 34229
- 4 Beds
- 2 Baths
- 1,867 Sq Ft
- Built 1996
Last Sold Summary
- 17% Below List Price
- $268/SF
- 250 Days On Market
Current Estimated Value $493,868

Last Listing Agent Toni Zarghami KW COASTAL LIVING III

629 Oak Bay Dr, Osprey, FL 34229
/2
$400,000 Sold Apr 08, 2025

4239 Expedition Way, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 2016
Last Sold Summary
- 6% Below List Price
- $254/SF
- 115 Days On Market
Current Estimated Value $390,757

Last Listing Agent Joe Cleary RE/MAX ALLIANCE GROUP

4239 Expedition Way, Osprey, FL 34229
/2
$650,000 Sold Apr 18, 2025

610 Pine Ranch Rd E, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,431 Sq Ft
- Built 1995
Last Sold Summary
- 7% Below List Price
- $267/SF
- 113 Days On Market
Current Estimated Value $631,669

Last Listing Agent Kim Klee COLDWELL BANKER REALTY

610 Pine Ranch Rd E, Osprey, FL 34229
/2
$470,000 Sold Aug 22, 2025

1110 Beachcomber Ct Unit 1, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,166 Sq Ft
- Built 2005
Last Sold Summary
- 15% Below List Price
- $217/SF
- 80 Days On Market
Current Estimated Value $484,183

Last Listing Agent Margaret Kennedy MICHAEL SAUNDERS & COMPANY

1110 Beachcomber Ct Unit 1, Osprey, FL 34229
/2
$3,315,000 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
- $384/SF
- 150 Days On Market
Current Estimated Value $3,087,979

Last Listing Agent Damon Lee STA Realty LLC

112 Osprey Point Dr, Osprey, FL 34229
/2
$250,000 Sold Oct 23, 2025

207 Woodland Dr Unit 207, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,325 Sq Ft
- Built 1980
Last Sold Summary
- 18% Below List Price
- $189/SF
- 491 Days On Market
Current Estimated Value $243,295

Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

207 Woodland Dr Unit 207, Osprey, FL 34229
/2
$772,000 Sold Mar 04, 2025

663 Crane Prairie Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,306 Sq Ft
- Built 2003
Last Sold Summary
- 1% Below List Price
- $335/SF
- 9 Days On Market
Current Estimated Value $752,300

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

663 Crane Prairie Way, Osprey, FL 34229
/2
$1,850,000 Sold Nov 07, 2025

67 Sugar Mill Dr, Osprey, FL 34229
- 4 Beds
- 5 Baths
- 4,020 Sq Ft
- Built 1989
Last Sold Summary
- 7% Below List Price
- $460/SF
- 240 Days On Market
Current Estimated Value $1,820,252

Last Listing Agent Paula Mapp MAPP REALTY & INVESTMENT CO

67 Sugar Mill Dr, Osprey, FL 34229

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