191 total properties
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 458 N SHORE DRIVE Osprey, FL MLS# N6139405
  • Virtual Tour
1 of 24
$600,000
Studio

Beds

0.0

Baths

458 N SHORE DRIVE

Osprey, FL

Courtesy of GULF SHORES REALTY
View 4428 CONCHFISH LANE Osprey, FL MLS# A4656074
  • Virtual Tour
1 of 13
$599,000
4

Beds

2.0

Baths

1,861

Sq.Ft.

4428 CONCHFISH LANE

Osprey, FL

Courtesy of HORIZON REALTY INTERNATIONAL
The time to sell is now! THE TIME TO SELL IS NOW!
View 250 HIDDEN BAY DRIVE 302 Osprey, FL MLS# A4657042
  • Virtual Tour
1 of 65
$689,000
3

Beds

2.0

Baths

1,937

Sq.Ft.

250 HIDDEN BAY DRIVE 302

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 140 SUGAR MILL DRIVE Osprey, FL MLS# A4655736
  • Virtual Tour
1 of 67
$1,970,000
4

Beds

4.0

Baths

3,286

Sq.Ft.

140 SUGAR MILL DRIVE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 3976 DESTINATION DRIVE A411 Osprey, FL MLS# A4643099
$1,000,000
2,314

Sq.Ft.

3976 DESTINATION DRIVE A411

Osprey, FL

Courtesy of PREMIER PROPERTIES OF SRQ LLC
View 401 N POINT ROAD 504 Osprey, FL MLS# A4653470
  • Virtual Tour
1 of 96
OPEN HOUSE: Sunday 2/22 1:00 PM - 3:00 PM
$990,000
3

Beds

3.0

Baths

2,778

Sq.Ft.

401 N POINT ROAD 504

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 296 PINE RANCH TRAIL Osprey, FL MLS# A4653218
  • Virtual Tour
1 of 82
$1,295,000
5

Beds

3.1

Baths

3,481

Sq.Ft.

296 PINE RANCH TRAIL

Osprey, FL

Courtesy of ASHTON LAKES REALTY INC
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 HIDDEN BAY DRIVE Osprey, FL MLS# A4645997
$800,000
Studio

Beds

0.0

Baths

HIDDEN BAY DRIVE

Osprey, FL

Courtesy of SVN COMMERCIAL ADVISORY GROUP
View 120 VILLA DRIVE 120 Osprey, FL MLS# N6138441
  • Virtual Tour
1 of 55
OPEN HOUSE: Sunday 2/22 12:00 PM - 3:00 PM
$515,000
2

Beds

2.0

Baths

1,404

Sq.Ft.

120 VILLA DRIVE 120

Osprey, FL

Courtesy of COLDWELL BANKER SARASOTA CENT.
View 110 PINE AVENUE Osprey, FL MLS# A4646339
  • Virtual Tour
1 of 11
$699,000
3

Beds

2.0

Baths

2,058

Sq.Ft.

110 PINE AVENUE

Osprey, FL

Courtesy of BRIGHT REALTY
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
$850,000
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
View 1216 N CASEY KEY ROAD Osprey, FL MLS# A4643654
  • Virtual Tour
1 of 60
$10,750,000
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 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
$875,000
3

Beds

3.0

Baths

2,778

Sq.Ft.

393 N POINT ROAD 604

Osprey, FL

Courtesy of ROBERT SLACK 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 2/20/2026.