164 total properties
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 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 121 N CASEY KEY ROAD Osprey, FL MLS# A4667263
  • Virtual Tour
1 of 77
$7,100,000
4

Beds

5.1

Baths

4,096

Sq.Ft.

121 N CASEY KEY ROAD

Osprey, FL

Courtesy of DOUGLAS ELLIMAN
The time to sell is now! THE TIME TO SELL IS NOW!
View 144 N CASEY KEY ROAD Osprey, FL MLS# A4660004
  • Virtual Tour
1 of 54
$5,990,000
4

Beds

5.1

Baths

5,397

Sq.Ft.

144 N CASEY KEY ROAD

Osprey, FL

Courtesy of DOUGLAS ELLIMAN
View 614 BAYSHORE DRIVE Osprey, FL MLS# A4662210
  • New Construction with Virtual Tour
1 of 61
$5,500,000
3

Beds

4.1

Baths

4,048

Sq.Ft.

614 BAYSHORE DRIVE

Osprey, FL

Courtesy of DOUGLAS ELLIMAN
View 730 SARABAY ROAD Osprey, FL MLS# A4672618
  • Virtual Tour
1 of 95
$5,495,000
4

Beds

5.1

Baths

6,308

Sq.Ft.

730 SARABAY ROAD

Osprey, FL

Courtesy of ROBERT SLACK LLC
View 101 OSPREY POINT DRIVE Osprey, FL MLS# A4664424
  • Virtual Tour
1 of 56
$5,000,000
4

Beds

5.1

Baths

5,087

Sq.Ft.

101 OSPREY POINT DRIVE

Osprey, FL

Courtesy of DOUGLAS ELLIMAN
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 691 EAGLE WATCH LANE Osprey, FL MLS# A4668477
  • Virtual Tour
1 of 100
$3,995,000
4

Beds

5.2

Baths

6,705

Sq.Ft.

691 EAGLE WATCH LANE

Osprey, FL

Courtesy of SARASOTA TRUST REALTY COMPANY
View 854 MACEWEN DRIVE Osprey, FL MLS# A4668918
$3,950,000
4

Beds

4.2

Baths

9,081

Sq.Ft.

854 MACEWEN DRIVE

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 1042 N CASEY KEY ROAD Osprey, FL MLS# A4674771
  • Recently Listed with Virtual Tour
1 of 78
$3,750,000
4

Beds

4.1

Baths

4,781

Sq.Ft.

1042 N CASEY KEY ROAD

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 135 TINA ISLAND DRIVE Osprey, FL MLS# A4665474
  • Virtual Tour
1 of 32
$3,350,000
3

Beds

4.1

Baths

2,572

Sq.Ft.

135 TINA ISLAND DRIVE

Osprey, FL

Courtesy of FLATFEE.COM
View 141 N CASEY KEY ROAD Osprey, FL MLS# A4669513
$3,200,000
Studio

Beds

0.0

Baths

141 N CASEY KEY ROAD

Osprey, FL

Courtesy of WHITE SANDS REALTY GROUP FL
View 479 SOUTH CREEK DRIVE Osprey, FL MLS# N6141722
  • Virtual Tour
1 of 73
$3,200,000
5

Beds

5.1

Baths

4,261

Sq.Ft.

479 SOUTH CREEK DRIVE

Osprey, FL

Courtesy of KELLER WILLIAMS ISLAND LIFE REAL ESTATE
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
View 225 HARBOR HOUSE DRIVE Osprey, FL MLS# TB8438095
  • Virtual Tour
1 of 60
$2,690,000
6

Beds

4.0

Baths

4,546

Sq.Ft.

225 HARBOR HOUSE DRIVE

Osprey, FL

Courtesy of PINEYWOODS REALTY LLC
View 370 SUGAR MILL DRIVE Osprey, FL MLS# A4661218
  • Virtual Tour
1 of 87
$2,650,000
5

Beds

5.1

Baths

4,783

Sq.Ft.

370 SUGAR MILL DRIVE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 49 OSPREY POINT DRIVE Osprey, FL MLS# A4671762
$2,595,000
4

Beds

3.1

Baths

3,953

Sq.Ft.

49 OSPREY POINT DRIVE

Osprey, FL

Courtesy of MICHAEL SAUNDERS & COMPANY
View 852 MACEWEN DRIVE Osprey, FL MLS# A4659276
  • Virtual Tour
1 of 73
$2,550,000
3

Beds

3.1

Baths

4,519

Sq.Ft.

852 MACEWEN DRIVE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 432 SORRENTO DRIVE Osprey, FL MLS# A4669597
  • Virtual Tour
1 of 84
$2,550,000
3

Beds

3.1

Baths

3,640

Sq.Ft.

432 SORRENTO DRIVE

Osprey, FL

Courtesy of UKEEPCOMMISSION REAL ESTATE

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 12/25/2025.