133 total properties
View 329 BAY VISTA AVENUE Osprey, FL MLS# A4699464
  • Virtual Tour
1 of 30
OPEN HOUSE: Sunday 8/23 11:00 AM - 1:00 PM
$399,000
2

Beds

2.0

Baths

1,346

Sq.Ft.

329 BAY VISTA AVENUE

Osprey, FL

View 7204 JESSIE HARBOR DRIVE 7204 Osprey, FL MLS# A4697473
$395,000
2

Beds

2.0

Baths

1,255

Sq.Ft.

7204 JESSIE HARBOR DRIVE 7204

Osprey, FL

View 2251 JESSIE HARBOR DRIVE 2101 Osprey, FL MLS# A4698891
$359,000
2

Beds

2.0

Baths

1,400

Sq.Ft.

2251 JESSIE HARBOR DRIVE 2101

Osprey, FL

Courtesy of KELLER WILLIAMS ON THE WATER S
The time to sell is now! THE TIME TO SELL IS NOW!
View 436 S TAMIAMI TRAIL C4 Osprey, FL MLS# A4648348
$350,000
1,272

Sq.Ft.

436 S TAMIAMI TRAIL C4

Osprey, FL

View 89 NAVIGATION CIRCLE Osprey, FL MLS# A4694435
  • Virtual Tour
1 of 61
$320,000
2

Beds

2.0

Baths

1,449

Sq.Ft.

89 NAVIGATION CIRCLE

Osprey, FL

Courtesy of KW COASTAL LIVING II
View 173 NAVIGATION CIRCLE 107 Osprey, FL MLS# N6144704
$319,500
3

Beds

2.0

Baths

1,528

Sq.Ft.

173 NAVIGATION CIRCLE 107

Osprey, FL

View 108 VILLA DRIVE 108 Osprey, FL MLS# TB8539148
  • Recently Listed with Virtual Tour
1 of 16
$319,000
2

Beds

2.0

Baths

1,593

Sq.Ft.

108 VILLA DRIVE 108

Osprey, FL

Courtesy of LOKATION
View 4304 EXPEDITION WAY WAY 105 Osprey, FL MLS# N6143250
$318,000
3

Beds

2.0

Baths

1,528

Sq.Ft.

4304 EXPEDITION WAY WAY 105

Osprey, FL

View 4213 EXPEDITION WAY 107 Osprey, FL MLS# A4698337
$317,000
3

Beds

2.0

Baths

1,430

Sq.Ft.

4213 EXPEDITION WAY 107

Osprey, FL

Courtesy of DALTON WADE INC
View 4296 EXPEDITION WAY 104 Osprey, FL MLS# A4694926
$299,990
2

Beds

2.0

Baths

1,135

Sq.Ft.

4296 EXPEDITION WAY 104

Osprey, FL

Courtesy of EXP REALTY LLC
View 4226 FRONTIER LANE 103 Osprey, FL MLS# A4687965
$299,000
2

Beds

2.0

Baths

1,135

Sq.Ft.

4226 FRONTIER LANE 103

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 184 EXPLORER DRIVE Osprey, FL MLS# A4692249
  • Virtual Tour
1 of 30
$294,900
2

Beds

2.0

Baths

1,244

Sq.Ft.

184 EXPLORER DRIVE

Osprey, FL

Courtesy of DALTON WADE INC
View 456 WASHINGTON AVENUE Osprey, FL MLS# A4623594
$289,999
Studio

Beds

0.0

Baths

456 WASHINGTON AVENUE

Osprey, FL

View 1801 HIGHLAND ROAD Osprey, FL MLS# N6140508
$289,900
2

Beds

2.0

Baths

1,165

Sq.Ft.

1801 HIGHLAND ROAD

Osprey, FL

Courtesy of RE/MAX ALLIANCE GROUP
View 51 MAC EWEN DRIVE 14 Osprey, FL MLS# A4690371
$285,000
1

Beds

1.0

Baths

595

Sq.Ft.

51 MAC EWEN DRIVE 14

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 108 WOODLAND PLACE 108 Osprey, FL MLS# A4699279
  • Virtual Tour
1 of 50
OPEN HOUSE: Sunday 8/23 1:00 PM - 3:00 PM
$285,000
2

Beds

2.0

Baths

1,316

Sq.Ft.

108 WOODLAND PLACE 108

Osprey, FL

View 51 MACEWEN DRIVE 12 Osprey, FL MLS# A4690540
  • Virtual Tour
1 of 71
$275,000
1

Beds

1.0

Baths

623

Sq.Ft.

51 MACEWEN DRIVE 12

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 480 BLACKBURN POINT ROAD 6 Osprey, FL MLS# A4703031
$269,000
Studio

Beds

0.0

Baths

480 BLACKBURN POINT ROAD 6

Osprey, FL

Courtesy of MICHAEL SAUNDERS & COMPANY
View 4271 EXPEDITION WAY 103 Osprey, FL MLS# A4689541
$260,000
2

Beds

2.0

Baths

1,135

Sq.Ft.

4271 EXPEDITION WAY 103

Osprey, FL

Courtesy of KW COASTAL LIVING III
View 116 WOODLAND PLACE 116 Osprey, FL MLS# A4696616
  • Virtual Tour
1 of 45
OPEN HOUSE: Sunday 8/23 1:00 PM - 3:00 PM
$249,900
2

Beds

2.0

Baths

1,325

Sq.Ft.

116 WOODLAND PLACE 116

Osprey, FL

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

The data relating to real estate for sale on this web site comes in part from the BROKER RECIPROCITY Program of M.L.S. of Naples, Inc. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the BROKER RECIPROCITY logo (little black house) and detailed information about them includes the name of the listing brokerage.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

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 8/22/2026.