Osprey, FL Homes

/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 $434,089

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

1102 Jessie Harbor Dr, Osprey, FL 34229

/62
Est $317,334

Not Listed For Sale

250 Glenwood Ave, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,118 Sq Ft
- Built 1986
250 Glenwood Ave, Osprey, FL 34229

Last Sold Summary
- 9 Days On Market

/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 $283,968

Last Listing Agent Judi Cipollina COLDWELL BANKER REALTY

4267 Expedition Way, Osprey, FL 34229

/2
Est $287,167

Not Listed For Sale

208 Pennsylvania Ave, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 900 Sq Ft
- Built 1963
208 Pennsylvania Ave, Osprey, FL 34229

Last Sold Summary
- 33 Days On Market

/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 $697,648

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

409 N Point Rd Unit 603, Osprey, FL 34229

/2
Est $1,664,513

Not Listed For Sale

525 S Shore Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,315 Sq Ft
- Built 1972
525 S Shore Dr, Osprey, FL 34229

Last Sold Summary
- 108 Days On Market

/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 $140,268

Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

570 Blackburn Point Rd Unit 19, Osprey, FL 34229

/2
Est $1,152,918

Not Listed For Sale

131 Tina Island Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,787 Sq Ft
- Built 1978
131 Tina Island Dr, Osprey, FL 34229

Last Sold Summary
- 10 Days On Market

/2
$840,000

Sold Apr 13, 2026

616 Crane Prairie Way, Osprey, FL 34229
- 3 Beds
- 4 Baths
- 3,561 Sq Ft
- Built 2005
Last Sold Summary
- 12% Below List Price
- $236/SF
- 39 Days On Market
Current Estimated Value $850,841

Last Listing Agent Matthew Greenland KELLER WILLIAMS ISLAND LIFE REAL ESTATE

616 Crane Prairie Way, Osprey, FL 34229

/27
Est $1,498,101

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
- 0 Days On Market

/2
$2,300,000

Sold Apr 07, 2026

530 N Mac Ewen Dr, Osprey, FL 34229
- 4 Beds
- 5.5 Baths
- 4,346 Sq Ft
- Built 2002
Last Sold Summary
- 4% Below List Price
- $529/SF
- 27 Days On Market
Current Estimated Value $2,286,461

Last Listing Agent Niall Phelan LPT REALTY, LLC

530 N Mac Ewen Dr, Osprey, FL 34229

/2
Est $783,619

Not Listed For Sale

448 Park Trace Blvd, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,060 Sq Ft
- Built 2002
448 Park Trace Blvd, Osprey, FL 34229

Last Sold Summary
- 145 Days On Market

/2
$365,000

Sold Apr 29, 2026

4235 Expedition Way Unit 102, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 2016
Last Sold Summary
- 4% Below List Price
- $232/SF
- 4 Days On Market
Current Estimated Value $364,383

Last Listing Agent Tim Weller EXIT KING REALTY

4235 Expedition Way Unit 102, Osprey, FL 34229

/2
Est $1,952,600

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
- 0 Days On Market

/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 $512,434

Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

1164 Beachcomber Ct Unit 19, Osprey, FL 34229

/2
Est $713,778

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
- 9 Days On Market

/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 $830,072

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

678 Crane Prairie Way, Osprey, FL 34229

/2
Est $565,119

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
- 41 Days On Market

/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 $2,217,116

Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

370 Sugar Mill Dr, Osprey, FL 34229

/2
Est $1,008,878

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
- 281 Days On Market

/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 $662,246

Last Listing Agent Mark Lyda GENEROUS PROPERTY

1212 Windward Dr, Osprey, FL 34229

/2
Est $1,191,246

Not Listed For Sale

223 Saint James Park, Osprey, FL 34229
- 3 Beds
- 5 Baths
- 3,321 Sq Ft
- Built 1991
223 Saint James Park, Osprey, FL 34229

Last Sold Summary
- 20 Days On Market

/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 $159,403

Last Listing Agent Carla Rayman Kidd COLDWELL BANKER REALTY

107 Woodland Place Unit 107, Osprey, FL 34229

/11
Est $2,151,742

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

/2
$200,000

Sold Dec 09, 2025

201 Woodland Dr Unit 201, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
- Built 1980
Last Sold Summary
- 33% Below List Price
- $152/SF
- 346 Days On Market
Current Estimated Value $200,758

Last Listing Agent Lauren Meadows PREFERRED PROPERTIES OF VENICE INC

201 Woodland Dr Unit 201, Osprey, FL 34229

/42
Est $249,793

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
- 12 Days On Market

/2
$1,014,000

Sold Nov 12, 2025

201 Eaglenook Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,379 Sq Ft
- Built 1992
Last Sold Summary
- 16% Below List Price
- $300/SF
- 211 Days On Market
Current Estimated Value $1,053,192

Last Listing Agent Dawn Bear WILLIAM RAVEIS - FLORIDA LLC

201 Eaglenook Way, Osprey, FL 34229

/65
Est $1,983,648

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
- 73 Days On Market

/2
$200,000

Sold Oct 06, 2025

444 Washington Ave, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,284 Sq Ft
- Built 1953
Last Sold Summary
- 20% Below List Price
- $156/SF
- 9 Days On Market
Current Estimated Value $215,121

Last Listing Agent Hansel Pitts COLDWELL BANKER SARASOTA CENT.

444 Washington Ave, Osprey, FL 34229

/2
Est $584,948

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
- 133 Days On Market

/2
$525,000

Sold Sep 30, 2025

116 Villa Dr Unit 116, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,221 Sq Ft
- Built 1968
Last Sold Summary
- $430/SF
- 2 Days On Market
Current Estimated Value $483,747

Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC

116 Villa Dr Unit 116, Osprey, FL 34229

/66
Est $153,358

Not Listed For Sale

767 Pine Run Dr, Osprey, FL 34229
- 1 Bed
- 1 Bath
- 736 Sq Ft
- Built 1973
767 Pine Run Dr, Osprey, FL 34229

Last Sold Summary
- 4 Days On Market

/43
Est $122,370

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
- 2 Days On Market

/72
Est $234,982

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
- 79 Days On Market

/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
- 114 Days On Market

/2
Est $370,077

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
- 2 Days On Market

/93
Est $1,817,202

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
- 4 Days On Market

/2
Est $1,571,872

Not Listed For Sale

716 Sarabay Rd, Osprey, FL 34229
- 2 Beds
- 3 Baths
- 1,857 Sq Ft
- Built 1975
716 Sarabay Rd, Osprey, FL 34229

Last Sold Summary
- 13 Days On Market

/59
Est $471,535

Not Listed For Sale

235 Woods Point Rd, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,936 Sq Ft
- Built 1993
235 Woods Point Rd, Osprey, FL 34229

Last Sold Summary
- 0 Days On Market

/54
Est $1,040,244

Not Listed For Sale

181 Lookout Point Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,899 Sq Ft
- Built 1997
181 Lookout Point Dr, Osprey, FL 34229

Last Sold Summary
- 13 Days On Market

Showing Results 601 - 640, Page 16 of 18

Florida Sarasota County Osprey

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