165 total properties
View 436 S TAMIAMI TRAIL C4 Osprey, FL MLS# A4648348
  • Virtual Tour
1 of 44
$374,900
1,272

Sq.Ft.

436 S TAMIAMI TRAIL C4

Osprey, FL

Courtesy of KONA REALTY
View 13 BAYHEAD LANE Osprey, FL MLS# A4645829
  • Virtual Tour
1 of 62
$965,000
2

Beds

2.0

Baths

2,310

Sq.Ft.

13 BAYHEAD LANE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 236 SAINT JAMES PARK Osprey, FL MLS# A4644125
  • Virtual Tour
1 of 88
$2,700,000
6

Beds

6.1

Baths

6,246

Sq.Ft.

236 SAINT JAMES PARK

Osprey, FL

Courtesy of MICHAEL SAUNDERS & COMPANY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1049 N CASEY KEY ROAD Osprey, FL MLS# N6137711
  • Virtual Tour
1 of 64
$4,750,000
3

Beds

3.0

Baths

2,582

Sq.Ft.

1049 N CASEY KEY ROAD

Osprey, FL

Courtesy of PREMIER SOTHEBYS INTL REALTY
View 1216 N CASEY KEY ROAD Osprey, FL MLS# A4643654
  • Virtual Tour
1 of 60
$11,750,000
5

Beds

6.2

Baths

8,050

Sq.Ft.

1216 N CASEY KEY ROAD

Osprey, FL

Courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY
View 280 HIDDEN BAY DRIVE 202 Osprey, FL MLS# A4643409
  • New Construction with Virtual Tour
1 of 43
$780,250
3

Beds

2.0

Baths

1,937

Sq.Ft.

280 HIDDEN BAY DRIVE 202

Osprey, FL

Courtesy of KELLER WILLIAMS ISLAND LIFE REAL ESTATE
View 820 PLACID LAKE DRIVE Osprey, FL MLS# A4640947
  • Virtual Tour
1 of 78
$1,095,000
5

Beds

4.0

Baths

3,938

Sq.Ft.

820 PLACID LAKE DRIVE

Osprey, FL

Courtesy of LOYD ROBBINS & CO. LLC
View 3603 N POINT ROAD 702 Osprey, FL MLS# A4642397
  • Virtual Tour
1 of 61
$1,395,000
3

Beds

3.0

Baths

2,545

Sq.Ft.

3603 N POINT ROAD 702

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 51 N TAMIAMI TRAIL Osprey, FL MLS# A4638654
  • Virtual Tour
1 of 53
$395,000
Studio

Beds

0.0

Baths

51 N TAMIAMI TRAIL

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 393 N POINT ROAD 604 Osprey, FL MLS# A4638035
  • Virtual Tour
1 of 92
$1,000,000
3

Beds

3.0

Baths

2,778

Sq.Ft.

393 N POINT ROAD 604

Osprey, FL

Courtesy of ROBERT SLACK LLC
View 385 N POINT ROAD 402 Osprey, FL MLS# A4635708
  • Virtual Tour
1 of 62
$660,000
3

Beds

3.0

Baths

2,055

Sq.Ft.

385 N POINT ROAD 402

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 227 SAINT JAMES PARK Osprey, FL MLS# A4635743
  • Virtual Tour
1 of 67
$995,000
2

Beds

2.0

Baths

2,071

Sq.Ft.

227 SAINT JAMES PARK

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 293 TURQUOISE LANE Osprey, FL MLS# A4633961
$910,000
3

Beds

2.0

Baths

2,271

Sq.Ft.

293 TURQUOISE LANE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 2251 JESSIE HARBOR DRIVE 2101 Osprey, FL MLS# A4631433
$395,000
2

Beds

2.0

Baths

1,400

Sq.Ft.

2251 JESSIE HARBOR DRIVE 2101

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 456 WASHINGTON AVENUE Osprey, FL MLS# A4623594
  • Virtual Tour
1 of 7
$269,999
Studio

Beds

0.0

Baths

456 WASHINGTON AVENUE

Osprey, FL

Courtesy of FLOTACAL
View 909 MACEWEN DRIVE Osprey, FL MLS# A4621683
  • Virtual Tour
1 of 62
$1,695,000
3

Beds

3.1

Baths

4,241

Sq.Ft.

909 MACEWEN DRIVE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 409 N POINT ROAD 502 Osprey, FL MLS# A4621353
  • Virtual Tour
1 of 48
$685,000
3

Beds

3.0

Baths

2,055

Sq.Ft.

409 N POINT ROAD 502

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 360 N POINT ROAD Osprey, FL MLS# A4617671
  • New Construction with Virtual Tour
1 of 57
$1,570,000
3

Beds

3.1

Baths

2,913

Sq.Ft.

360 N POINT ROAD

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 505 LUMINARY BOULEVARD Osprey, FL MLS# A4616676
  • Virtual Tour
1 of 10
$7,499,000
4,000

Sq.Ft.

505 LUMINARY BOULEVARD

Osprey, FL

Courtesy of AMERICAN PROPERTY GROUP
View 191 PALM AIR DRIVE Osprey, FL MLS# A4614751
  • Adult Community with Virtual Tour
1 of 45
$185,000
2

Beds

2.0

Baths

1,376

Sq.Ft.

191 PALM AIR DRIVE

Osprey, FL

Courtesy of FINE PROPERTIES

Information deemed reliable but not guaranteed.

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 12/21/2025.