166 total properties
View 20 BAYHEAD LANE Osprey, FL MLS# A4674649
  • Recently Listed with Virtual Tour
1 of 72
OPEN HOUSE: Sunday 1/11 12:00 PM - 3:00 PM
$1,575,000
4

Beds

3.0

Baths

3,486

Sq.Ft.

20 BAYHEAD LANE

Osprey, FL

Courtesy of EXP REALTY LLC
View 409 NORTH POINT ROAD 902 Osprey, FL MLS# A4677305
  • Recently Listed
1 of 59
$1,275,000
3

Beds

3.0

Baths

2,055

Sq.Ft.

409 NORTH POINT ROAD 902

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 570 BLACKBURN POINT ROAD LNG42 Osprey, FL MLS# A4677438
  • Recently Listed with Virtual Tour
1 of 15
$42,000
Studio

Beds

0.0

Baths

570 BLACKBURN POINT ROAD LNG42

Osprey, FL

Courtesy of RE/MAX ALLIANCE GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 2043 CORDES STREET Osprey, FL MLS# A4677419
  • Recently Listed with Virtual Tour
1 of 35
OPEN HOUSE: Saturday 1/10 12:00 PM - 2:00 PM
$299,000
3

Beds

2.0

Baths

1,186

Sq.Ft.

2043 CORDES STREET

Osprey, FL

Courtesy of PREFERRED SHORE LLC
View 6100 JESSIE HARBOR DRIVE 603 Osprey, FL MLS# A4676824
  • Recently Listed
1 of 43
OPEN HOUSE: Sunday 1/11 2:00 PM - 4:00 PM
$899,000
3

Beds

3.0

Baths

2,630

Sq.Ft.

6100 JESSIE HARBOR DRIVE 603

Osprey, FL

Courtesy of ENGEL + VOELKERS SARASOTA
View 186 WINDWARD DRIVE Osprey, FL MLS# N6142087
  • Recently Listed with Virtual Tour
1 of 93
OPEN HOUSE: Sunday 1/11 1:30 PM - 4:00 PM
$749,900
3

Beds

2.0

Baths

2,505

Sq.Ft.

186 WINDWARD DRIVE

Osprey, FL

Courtesy of KELLER WILLIAMS ON THE WATER S
View 1019 SCHERER WAY Osprey, FL MLS# N6142144
  • Recently Listed with Virtual Tour
1 of 56
OPEN HOUSE: Sunday 1/11 1:00 PM - 4:00 PM
$735,000
4

Beds

3.0

Baths

2,498

Sq.Ft.

1019 SCHERER WAY

Osprey, FL

Courtesy of CENTURY 21 SCHMIDT REAL ESTATE
View 100 NAVIGATION CIRCLE NA Osprey, FL MLS# A4676420
  • Recently Listed
1 of 45
OPEN HOUSE: Sunday 1/11 1:00 PM - 4:00 PM
$305,000
2

Beds

2.0

Baths

1,135

Sq.Ft.

100 NAVIGATION CIRCLE NA

Osprey, FL

Courtesy of MICHAEL SAUNDERS & COMPANY
View 616 CRANE PRAIRIE WAY Osprey, FL MLS# N6142165
  • Recently Listed with Virtual Tour
1 of 56
$960,000
3

Beds

4.0

Baths

3,561

Sq.Ft.

616 CRANE PRAIRIE WAY

Osprey, FL

Courtesy of KELLER WILLIAMS ISLAND LIFE REAL ESTATE
View 5100 JESSIE HARBOR DRIVE 403 Osprey, FL MLS# A4676382
  • Recently Listed
1 of 44
$679,900
2

Beds

2.0

Baths

2,143

Sq.Ft.

5100 JESSIE HARBOR DRIVE 403

Osprey, FL

Courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY
View 433 E MACEWEN DRIVE Osprey, FL MLS# A4676505
  • Recently Listed with Virtual Tour
1 of 72
$2,250,000
4

Beds

3.1

Baths

4,012

Sq.Ft.

433 E MACEWEN DRIVE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 524 SARABAY ROAD Osprey, FL MLS# A4676179
  • Recently Listed with Virtual Tour
1 of 41
$424,000
3

Beds

2.0

Baths

1,760

Sq.Ft.

524 SARABAY ROAD

Osprey, FL

Courtesy of SUN N SAND REAL ESTATE LLC
View 3813 PARROT BAY COURT Osprey, FL MLS# A4675945
  • Recently Listed with Virtual Tour
1 of 8
$700,000
Studio

Beds

0.0

Baths

3813 PARROT BAY COURT

Osprey, FL

Courtesy of COMPASS FLORIDA LLC
View 1303 THORNAPPLE DRIVE Osprey, FL MLS# A4675439
  • Virtual Tour
1 of 66
$699,000
3

Beds

2.0

Baths

1,929

Sq.Ft.

1303 THORNAPPLE DRIVE

Osprey, FL

Courtesy of KELLER WILLIAMS ON THE WATER S
View 365 S SHORE DRIVE Osprey, FL MLS# N6142101
  • Recently Listed with Virtual Tour
1 of 95
OPEN HOUSE: Saturday 1/10 4:00 PM - 6:00 PM
$1,400,000
3

Beds

2.0

Baths

1,824

Sq.Ft.

365 S SHORE DRIVE

Osprey, FL

Courtesy of EXIT KING REALTY
View 1042 N CASEY KEY ROAD Osprey, FL MLS# A4674771
  • 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 711 SHADOW BAY WAY Osprey, FL MLS# A4675020
  • Virtual Tour
1 of 59
$600,000
4

Beds

2.0

Baths

2,133

Sq.Ft.

711 SHADOW BAY WAY

Osprey, FL

Courtesy of MICHAEL SAUNDERS & COMPANY
View 678 FAITH AVENUE Osprey, FL MLS# A4674865
  • Virtual Tour
1 of 51
$990,000
3

Beds

3.0

Baths

2,583

Sq.Ft.

678 FAITH AVENUE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 85 NAVIGATION CIRCLE Osprey, FL MLS# A4674291
$339,000
3

Beds

2.0

Baths

1,430

Sq.Ft.

85 NAVIGATION CIRCLE

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 3983 DESTINATION DRIVE 102 Osprey, FL MLS# TB8455523
$1,050,000
2,030

Sq.Ft.

3983 DESTINATION DRIVE 102

Osprey, FL

Courtesy of COLDWELL BANKER REALTY

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 1/10/2026.