163 total properties
View 38 W BAY STREET Osprey, FL MLS# A4667010
  • Virtual Tour
1 of 60
$899,000
3

Beds

2.0

Baths

2,124

Sq.Ft.

38 W BAY STREET

Osprey, FL

Courtesy of HARRY ROBBINS ASSOC INC
View 147 OSPREY POINT DRIVE Osprey, FL MLS# A4667023
  • Virtual Tour
1 of 8
$750,000
Studio

Beds

0.0

Baths

147 OSPREY POINT DRIVE

Osprey, FL

Courtesy of BRIGHT REALTY
View 3957 WAYPOINT AVENUE Osprey, FL MLS# A4666325
  • Virtual Tour
1 of 24
$925,000
3

Beds

3.0

Baths

2,328

Sq.Ft.

3957 WAYPOINT AVENUE

Osprey, FL

Courtesy of RE/MAX ALLIANCE GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 742 HARMS DRIVE Osprey, FL MLS# A4666421
  • Virtual Tour
1 of 46
OPEN HOUSE: Saturday 12/20 11:00 AM - 1:00 PM
$545,000
3

Beds

2.0

Baths

1,293

Sq.Ft.

742 HARMS DRIVE

Osprey, FL

Courtesy of EXP REALTY LLC
View 244 WOODLAND DRIVE 244 Osprey, FL MLS# A4667419
  • Virtual Tour
1 of 48
$225,000
2

Beds

2.0

Baths

1,325

Sq.Ft.

244 WOODLAND DRIVE 244

Osprey, FL

Courtesy of KELLER WILLIAMS ON THE WATER S
View 123 WINDWARD DRIVE Osprey, FL MLS# A4656319
  • Virtual Tour
1 of 77
OPEN HOUSE: Sunday 12/21 1:00 PM - 4:00 PM
$850,000
3

Beds

2.0

Baths

1,894

Sq.Ft.

123 WINDWARD DRIVE

Osprey, FL

Courtesy of WILLIAM RAVEIS REAL ESTATE
View 571 PINE RANCH EAST ROAD Osprey, FL MLS# A4665938
  • Virtual Tour
1 of 87
$685,000
5

Beds

2.1

Baths

2,746

Sq.Ft.

571 PINE RANCH EAST ROAD

Osprey, FL

Courtesy of MICHAEL SAUNDERS & COMPANY
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 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 3983 DESTINATION DRIVE 102-202 Osprey, FL MLS# TB8428492
$1,700,000
3,871

Sq.Ft.

3983 DESTINATION DRIVE 102-202

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
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 21 BAYHEAD LANE Osprey, FL MLS# A4664085
$900,000
3

Beds

2.0

Baths

2,216

Sq.Ft.

21 BAYHEAD LANE

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 508 MEADOW SWEET CIRCLE Osprey, FL MLS# A4664579
  • Virtual Tour
1 of 76
$455,000
2

Beds

2.0

Baths

1,604

Sq.Ft.

508 MEADOW SWEET CIRCLE

Osprey, FL

Courtesy of FLORIDA HOME TEAM LLC
View 701 EAGLENOOK WAY Osprey, FL MLS# A4663832
  • Virtual Tour
1 of 65
$1,025,000
4

Beds

4.1

Baths

3,533

Sq.Ft.

701 EAGLENOOK WAY

Osprey, FL

Courtesy of COLDWELL BANKER SARASOTA CENT.
View 1801 HIGHLAND ROAD Osprey, FL MLS# N6140508
$330,000
2

Beds

2.0

Baths

1,165

Sq.Ft.

1801 HIGHLAND ROAD

Osprey, FL

Courtesy of RE/MAX ALLIANCE GROUP
View 133 OSPREY POINT DRIVE Osprey, FL MLS# A4664295
  • Virtual Tour
1 of 99
$1,350,000
4

Beds

3.0

Baths

3,679

Sq.Ft.

133 OSPREY POINT DRIVE

Osprey, FL

Courtesy of OWN SRQ LLC
View 707 PINE RUN DRIVE Osprey, FL MLS# N6140309
$289,000
2

Beds

2.0

Baths

1,379

Sq.Ft.

707 PINE RUN DRIVE

Osprey, FL

Courtesy of RESULTS REALTY GROUP LLC
View 1218 YACHT HARBOR DRIVE Osprey, FL MLS# A4663579
  • Virtual Tour
1 of 98
$1,150,000
3

Beds

3.0

Baths

3,297

Sq.Ft.

1218 YACHT HARBOR DRIVE

Osprey, FL

Courtesy of KELLER WILLIAMS ON THE WATER S
View 1337 COPPERWOOD DRIVE Osprey, FL MLS# A4666722
  • Virtual Tour
1 of 36
$595,000
3

Beds

2.0

Baths

2,172

Sq.Ft.

1337 COPPERWOOD DRIVE

Osprey, FL

Courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY
View 140 N CASEY KEY ROAD Osprey, FL MLS# A4665482
$2,350,000
3

Beds

3.1

Baths

2,473

Sq.Ft.

140 N CASEY KEY ROAD

Osprey, FL

Courtesy of EXP REALTY LLC

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 12/20/2025.