50 photos $2,095,000
4 bd 3.5 ba 4,578 sqft
154 Lookout Point Dr
Osprey, FL 34229 · Southbay Yacht & Racquet Club
Courtesy of FLAT FEE MLS REALTY
Homes for sale matching “Osprey”
50 photos
Courtesy of FLAT FEE MLS REALTY
100 photos $1,000,000
5 bd 3.5 ba 3,354 sqft
296 Pine Ranch Trl
Osprey, FL 34229 · Pine Ranch East
Courtesy of BEYOND REALTY LLC
53 photos $229,900
2 bd 2 ba 1,280 sqft
158 Osprey Cir
Ellenton, FL 34222 · Ridgewood Meadows Ph Ii & Iii
Courtesy of LESLIE WELLS REALTY, INC.
89 photos $1,350,000
3 bd 2.5 ba 2,591 sqft
226 Saint James Park
Osprey, FL 34229 · Oaks 2 Ph 1
Courtesy of KELLER WILLIAMS ON THE WATER S
60 photos $985,000
3 bd 3 ba 2,203 sqft
409 N Point Rd #803
Osprey, FL 34229 · Meridian At The Oaks Preserve
Courtesy of GENEROUS PROPERTY
2 photos $562,900
0 ba 1,204 sqft
Address not disclosed
Osprey, FL 34229 · Phase 2 Of Bay Street
Courtesy of CENTURY 21 ROSEBAY
62 photos $599,000
2 bd 2 ba 2,143 sqft
5100 Jessie Harbor Dr #404
Osprey, FL 34229 · Blackburn Harbor Residences
Courtesy of MICHAEL SAUNDERS & COMPANY
30 photos $2,999,000
4 bd 4 ba 2,915 sqft
1426 S Osprey Ave
Sarasota, FL 34239 · Matheneys Sub
Courtesy of COMPASS FLORIDA LLC
36 photos $2,850,000
4.18 acres
2301 S Tamiami Trl
Osprey, FL 34229 · Springhill Park
Courtesy of SARABAY REAL ESTATE INC
79 photos $699,000
3 bd 2 ba 2,328 sqft
299 Turquoise Ln
Osprey, FL 34229 · Oaks
Courtesy of BRIGHT REALTY
54 photos $630,000
4 bd 2 ba 2,186 sqft
1036 Oak Meadow Ln
Osprey, FL 34229 · Rivendell, Unit 3-a
Courtesy of BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE
58 photos $760,000
3 bd 2.5 ba 1,950 sqft
260 Hidden Bay Dr #402
Osprey, FL 34229 · Edgewater/hidden Bay Bldg B Ph
Courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY
4 photos $99,500
0 ba
570 Blackburn Point Rd #36
Osprey, FL 34229 · Dry Slips At Bellagio Village
Courtesy of BRIGHT REALTY
54 photos $425,000
2 bd 2 ba 1,574 sqft
780 Sarabay Rd #16
Osprey, FL 34229 · Heron Bay Club Sec I
Courtesy of RMS ELITE PROPERTIES
25 photos $600,000
0.34 acres
458 N Shore Dr
Osprey, FL 34229 · Sorrento Shores
Courtesy of PREMIER SOTHEBYS INTL REALTY
85 photos $480,000
3 bd 2.5 ba 2,006 sqft
2309 Jessie Harbor Dr #2402
Osprey, FL 34229 · Blackburn Harbor Waterfront Villas
Courtesy of MICHAEL SAUNDERS & COMPANY
12 photos $825,000
0.24 acres
3820 Parrot Bay Ct
Osprey, FL 34229 · Parrot Bay
Courtesy of HARRY ROBBINS ASSOC INC
3 photos $89,000
0 ba
570 Blackburn Point Rd #23
Osprey, FL 34229 · Dry Slips At Bellagio Village
Courtesy of MICHAEL SAUNDERS & COMPANY
43 photos $395,000
2 bd 2 ba 1,255 sqft
7204 Jessie Harbor Dr #7204
Osprey, FL 34229 · Heron House
Courtesy of GENEROUS PROPERTY
33 photos $400,000
0 ba 1,272 sqft
418 S Tamiami Trl #e3
Osprey, FL 34229 · Osprey Executive Park
Courtesy of KELLER WILLIAMS ISLAND LIFE REAL ESTATE
11 photos $575,000
0.4 acres
143 Osprey Point Dr
Osprey, FL 34229
Courtesy of COLDWELL BANKER REALTY
70 photos $1,595,000
4 bd 4 ba 4,001 sqft
75 Osprey Point Dr
Osprey, FL 34229 · Oaks
Courtesy of COLDWELL BANKER REALTY
45 photos $242,900
2 bd 2 ba 1,325 sqft
116 Woodland Pl #116
Osprey, FL 34229 · Pine Run Ii
Courtesy of PAT WILLIAMS REALTY, LLC
49 photos $1,445,000
3 bd 3.5 ba 2,913 sqft
360 N Point Rd
Osprey, FL 34229 · Oaks
Courtesy of COLDWELL BANKER REALTY
Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS. Last updated: 2026-11-04 10:44 PM EST.