165 total properties
View 761 PINE RUN DRIVE 761 Osprey, FL MLS# A4673659
$279,000
2

Beds

2.0

Baths

1,379

Sq.Ft.

761 PINE RUN DRIVE 761

Osprey, FL

Courtesy of COLDWELL BANKER SARASOTA CENT.
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 232 EXPLORER DRIVE 15 Osprey, FL MLS# A4648458
  • Virtual Tour
1 of 28
$299,500
2

Beds

2.0

Baths

1,135

Sq.Ft.

232 EXPLORER DRIVE 15

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 116 NAVIGATION CIRCLE 106 Osprey, FL MLS# A4658738
$325,000
3

Beds

2.0

Baths

1,430

Sq.Ft.

116 NAVIGATION CIRCLE 106

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
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 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 436 S TAMIAMI TRAIL C4 Osprey, FL MLS# A4648348
$374,900
1,272

Sq.Ft.

436 S TAMIAMI TRAIL C4

Osprey, FL

Courtesy of KONA REALTY
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 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 291 HIDDEN BAY DRIVE 101 Osprey, FL MLS# N6141302
$400,000
2

Beds

2.0

Baths

1,599

Sq.Ft.

291 HIDDEN BAY DRIVE 101

Osprey, FL

Courtesy of PARADISE EXCLUSIVE INC
View 524 SARABAY ROAD Osprey, FL MLS# A4676179
  • Recently Listed with Virtual Tour
1 of 23
$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 352 GLENWOOD AVE Osprey, FL MLS# N6138982
  • Virtual Tour
1 of 36
$429,500
3

Beds

2.0

Baths

1,300

Sq.Ft.

352 GLENWOOD AVE

Osprey, FL

Courtesy of WHITE SANDS REALTY GROUP FL
View 780 SARABAY ROAD 16 Osprey, FL MLS# TB8402328
  • Virtual Tour
1 of 55
$429,900
2

Beds

2.0

Baths

1,574

Sq.Ft.

780 SARABAY ROAD 16

Osprey, FL

Courtesy of RMS ELITE PROPERTIES
View 1811 HIGHLAND ROAD Osprey, FL MLS# TB8443161
  • Virtual Tour
1 of 19
$433,000
2

Beds

2.0

Baths

1,725

Sq.Ft.

1811 HIGHLAND ROAD

Osprey, FL

Courtesy of REALTY OF RIVERVIEW LLC
View 508 MEADOW SWEET CIRCLE Osprey, FL MLS# A4664579
$455,000
2

Beds

2.0

Baths

1,604

Sq.Ft.

508 MEADOW SWEET CIRCLE

Osprey, FL

Courtesy of FLORIDA HOME TEAM LLC
View 32 BAY AVENUE Osprey, FL MLS# N6140978
  • Virtual Tour
1 of 51
$463,000
2

Beds

2.0

Baths

2,148

Sq.Ft.

32 BAY AVENUE

Osprey, FL

Courtesy of NEXTHOME BEACH TO BAY
View 7303 JESSIE HARBOR DRIVE 7303 Osprey, FL MLS# D6142543
$474,900
3

Beds

2.0

Baths

1,883

Sq.Ft.

7303 JESSIE HARBOR DRIVE 7303

Osprey, FL

Courtesy of KW COASTAL LIVING
View 1363 NEW FOREST LANE Osprey, FL MLS# A4648690
  • Virtual Tour
1 of 24
$499,000
2

Beds

2.0

Baths

1,738

Sq.Ft.

1363 NEW FOREST LANE

Osprey, FL

Courtesy of RE/MAX PALM
View 401 N POINT ROAD 301 Osprey, FL MLS# A4603773
  • Virtual Tour
1 of 91
$500,000
3

Beds

3.0

Baths

2,594

Sq.Ft.

401 N POINT ROAD 301

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 120 VILLA DRIVE 120 Osprey, FL MLS# N6138441
  • Virtual Tour
1 of 55
$525,000
2

Beds

2.0

Baths

1,404

Sq.Ft.

120 VILLA DRIVE 120

Osprey, FL

Courtesy of COLDWELL BANKER SARASOTA CENT.

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 12/27/2025.