Communities in Osprey
53 subdivisions with active listings
Listings in Osprey
See all →
$10,750,000
1216 N Casey Key Rd
Osprey, FL 34229
5 bd · 8 ba · 8,050 sqft
Casey Key
MLS ID #A4643654, PREMIER SOTHEBYS INTL REALTY.
Listing provided by Stellar MLS
$6,475,000
121 N Casey Key Rd
Osprey, FL 34229
5 bd · 6 ba · 4,096 sqft
Casey Key
MLS ID #A4667263, DOUGLAS ELLIMAN.
Listing provided by Stellar MLS
$5,999,999
313 Lookout Point Dr
Osprey, FL 34229
4 bd · 5 ba · 5,337 sqft
Southbay Yacht & Racquet Club
MLS ID #A4688995, MICHAEL SAUNDERS & COMPANY.
Listing provided by Stellar MLS
$4,790,000
101 Osprey Point Dr
Osprey, FL 34229
4 bd · 6 ba · 5,087 sqft
The Oaks
MLS ID #A4694716, DOUGLAS ELLIMAN.
Listing provided by Stellar MLS
$3,995,000
324 Bayshore Dr
Osprey, FL 34229
4 bd · 5 ba · 4,389 sqft
Bay Acres - Resub
MLS ID #A4683138, MICHAEL SAUNDERS & COMPANY.
Listing provided by Stellar MLS
$3,690,000
854 Macewen Dr
Osprey, FL 34229
4 bd · 6 ba · 9,081 sqft
Oaks 2 Ph 2
MLS ID #A4668918, COLDWELL BANKER REALTY.
Listing provided by Stellar MLS
$3,295,000
135 Tina Island Dr
Osprey, FL 34229
3 bd · 5 ba · 2,572 sqft
Sorrento Shores
MLS ID #A4692366, GENEROUS PROPERTY.
Listing provided by Stellar MLS
$2,995,000
14401 Masthead Dr
Osprey, FL 34229
3 bd · 4 ba · 2,665 sqft
Bayside
MLS ID #A4684834, MICHAEL SAUNDERS & COMPANY.
Listing provided by Stellar MLS
$2,850,000
141 N Casey Key Rd
Osprey, FL 34229
0.39 acres
MLS ID #A4669513, WHITE SANDS REALTY GROUP FL.
Listing provided by Stellar MLS
$2,700,000
236 Saint James Park
Osprey, FL 34229
6 bd · 7 ba · 6,246 sqft
Oaks 2 Ph 1
MLS ID #A4644125, MICHAEL SAUNDERS & COMPANY.
Listing provided by Stellar MLS
$2,399,000
49 Osprey Point Dr
Osprey, FL 34229
4 bd · 4 ba · 3,953 sqft
Oaks
MLS ID #A4671762, MICHAEL SAUNDERS & COMPANY.
Listing provided by Stellar MLS
$2,395,000
852 Macewen Dr
Osprey, FL 34229
3 bd · 4 ba · 4,519 sqft
Oaks 2 Ph 2
MLS ID #A4659276, GENEROUS PROPERTY.
Listing provided by Stellar MLS
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 17, 2026 at 1:17 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA