Homes for sale in Osprey.

133 active listings in Osprey, FL — live Stellar MLS inventory.

Communities in Osprey

58 subdivisions with active listings

Oaks19 Meridian At The Oaks Preserve17 Bay Street Village6 Dry Slips At Bellagio Village6 Southbay Yacht & Racquet Club6 Sorrento Shores4 Bay Acres - Resub3 Blackburn Harbor Residences3 Casey Key3 Osprey Park 23 Palms/Casey Key3 Park Trace Estates3 Villas At Bellagio Harbor Village3 Windsor Lodge At The Oaks3 Arbors2 Heron Bay Club Sec I2 Hidden Bay2 Oaks 2 Ph 12 Oaks 2 Ph 22 Rivendell Woodlands2 Sorrento East2 Towns-End Shores2 Trinity Acres2 Bay Oaks Estates1 Baypointe Vista 11 Bayside1 Bel-Air1 Bishops Court At Oaks Preserve1 Bishopscourt At The Oaks Preserve1 Blackburn Harbor Waterfront Vi1 Blackburn Harbor Waterfront Villas1 Blackburn Point Marina Village1 Edgewater At Hidden Bay1 Edgewater/Hidden Bay Ph 2 Bldg1 Edgewater/Hidden Bay Ph 31 Emerald Woods At Oaks 03 Ph 021 Harms Sub1 Heron House1 Oaks 2 Ph 4-C Pt 31 Oaks 2 Phase 21 Oaks 3 Ph 11 Osprey Executive Park1 Palmer1 Phase 2 Of Bay Street1 Pine Ranch1 Pine Ranch East1 Pine Run I1 Pine Run Iii1 Sarabay Acres1 Saunders V A Resub1 Siesta Rev Resub Of Pt1 Sorrento Shores Rep Of 21 Sorrento Shores Unit 11 Sorrento Villas 11 The Oaks1 The Oaks Club1 Villas/Harbor Village1 Willowbend Ph 31

Listings in Osprey

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ActiveSingle Family Residence360°

$10,750,000

1216 N Casey Key Rd

Osprey, FL 34229

5 bd · 8 ba · 8,050 sqft

Casey Key

MLS# A4643654

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ActiveSingle Family Residence360°

$6,475,000

121 N Casey Key Rd

Osprey, FL 34229

5 bd · 6 ba · 4,096 sqft

Casey Key

MLS# A4667263

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ActiveSingle Family Residence

$5,999,999

313 Lookout Point Dr

Osprey, FL 34229

4 bd · 5 ba · 5,337 sqft

Southbay Yacht & Racquet Club

MLS# A4688995

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ActiveSingle Family Residence360°

$4,790,000

101 Osprey Point Dr

Osprey, FL 34229

4 bd · 6 ba · 5,087 sqft

The Oaks

MLS# A4694716

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ActiveSingle Family Residence360°

$3,995,000

324 Bayshore Dr

Osprey, FL 34229

4 bd · 5 ba · 4,389 sqft

Bay Acres - Resub

MLS# A4683138

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ActiveSingle Family Residence360°

$3,750,000

1042 N Casey Key Rd

Osprey, FL 34229

4 bd · 5 ba · 4,781 sqft

Palmer

MLS# A4674771

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ActiveSingle Family Residence

$3,690,000

854 Macewen Dr

Osprey, FL 34229

4 bd · 6 ba · 9,081 sqft

Oaks 2 Ph 2

MLS# A4668918

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ActiveSingle Family Residence360°

$3,295,000

135 Tina Island Dr

Osprey, FL 34229

3 bd · 5 ba · 2,572 sqft

Sorrento Shores

MLS# A4692366

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ActiveSingle Family Residence

$3,150,000

14401 Masthead Dr

Osprey, FL 34229

3 bd · 4 ba · 2,665 sqft

Bayside

MLS# A4684834

Active360°

$2,850,000

141 N Casey Key Rd

Osprey, FL 34229

0.39 acres

MLS# A4669513

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ActiveSingle Family Residence360°

$2,850,000

662 Fernwalk Ln

Osprey, FL 34229

4 bd · 4 ba · 4,359 sqft

Oaks

MLS# A4679996

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ActiveSingle Family Residence360°

$2,700,000

236 Saint James Park

Osprey, FL 34229

6 bd · 7 ba · 6,246 sqft

Oaks 2 Ph 1

MLS# A4644125

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 May 28, 2026 at 12:03 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