193 total properties
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 177 NAVIGATION CIRCLE Osprey, FL MLS# A4680685
$369,000
3

Beds

2.1

Baths

1,581

Sq.Ft.

177 NAVIGATION CIRCLE

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 172 EXPLORER DRIVE Osprey, FL MLS# A4678068
  • Virtual Tour
1 of 61
$350,000
2

Beds

2.0

Baths

1,449

Sq.Ft.

172 EXPLORER DRIVE

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 4284 EXPEDITION WAY NA Osprey, FL MLS# A4681835
  • Recently Listed with Virtual Tour
1 of 40
$350,000
3

Beds

2.0

Baths

1,430

Sq.Ft.

4284 EXPEDITION WAY NA

Osprey, FL

Courtesy of PREFERRED SHORE LLC
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 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 100 NAVIGATION CIRCLE NA Osprey, FL MLS# A4676420
$305,000
2

Beds

2.0

Baths

1,135

Sq.Ft.

100 NAVIGATION CIRCLE NA

Osprey, FL

Courtesy of MICHAEL SAUNDERS & COMPANY
View 51 MACEWEN DRIVE 11 Osprey, FL MLS# A4679180
  • Virtual Tour
1 of 38
$300,000
1

Beds

1.0

Baths

623

Sq.Ft.

51 MACEWEN DRIVE 11

Osprey, FL

Courtesy of 342 REAL ESTATE
View 2043 CORDES STREET Osprey, FL MLS# A4677419
  • Virtual Tour
1 of 35
$289,000
3

Beds

2.0

Baths

1,186

Sq.Ft.

2043 CORDES STREET

Osprey, FL

Courtesy of PREFERRED SHORE LLC
View 456 WASHINGTON AVENUE Osprey, FL MLS# A4623594
$269,999
Studio

Beds

0.0

Baths

456 WASHINGTON AVENUE

Osprey, FL

Courtesy of FLOTACAL
View 232 WOODLAND DRIVE 232 Osprey, FL MLS# A4671600
$264,900
2

Beds

2.0

Baths

1,325

Sq.Ft.

232 WOODLAND DRIVE 232

Osprey, FL

Courtesy of PAT WILLIAMS REALTY, LLC
View 216 GLENWOOD AVENUE Osprey, FL MLS# A4673441
  • Virtual Tour
1 of 41
$250,000
2

Beds

1.0

Baths

732

Sq.Ft.

216 GLENWOOD AVENUE

Osprey, FL

Courtesy of COMPASS FLORIDA LLC
View 362 PINE RUN DRIVE Osprey, FL MLS# A4672574
  • Virtual Tour
1 of 69
$235,000
2

Beds

2.0

Baths

1,224

Sq.Ft.

362 PINE RUN DRIVE

Osprey, FL

Courtesy of COMPASS FLORIDA LLC
View 252 SUN AIR CIRCLE Osprey, FL MLS# A4683143
  • Recently Listed with Virtual Tour
1 of 86
$235,000
2

Beds

2.0

Baths

1,152

Sq.Ft.

252 SUN AIR CIRCLE

Osprey, FL

Courtesy of COLDWELL BANKER SARASOTA CENT.
View 244 WOODLAND DRIVE 244 Osprey, FL MLS# A4667419
  • Virtual Tour
1 of 48
OPEN HOUSE: Sunday 2/22 11:00 AM - 1:00 PM
$215,000
2

Beds

2.0

Baths

1,325

Sq.Ft.

244 WOODLAND DRIVE 244

Osprey, FL

Courtesy of KELLER WILLIAMS ON THE WATER S
View 354 PINE RUN DRIVE Osprey, FL MLS# A4683173
  • Recently Listed with Virtual Tour
1 of 75
$200,000
2

Beds

2.0

Baths

1,224

Sq.Ft.

354 PINE RUN DRIVE

Osprey, FL

Courtesy of COMPASS FLORIDA LLC
View 14 OLD VENICE ROAD Osprey, FL MLS# A4682477
  • Recently Listed with Virtual Tour
1 of 20
$190,000
Studio

Beds

0.0

Baths

14 OLD VENICE ROAD

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 238 PALM AIR DRIVE Osprey, FL MLS# A4658930
  • Adult Community with Virtual Tour
1 of 41
OPEN HOUSE: Sunday 2/22 2:00 PM - 4:00 PM
$185,000
2

Beds

2.0

Baths

1,152

Sq.Ft.

238 PALM AIR DRIVE

Osprey, FL

Courtesy of FINE PROPERTIES
View 316 TROPIC DRIVE Osprey, FL MLS# A4681219
  • Recently Listed with Virtual Tour
1 of 84
$185,000
2

Beds

2.0

Baths

1,151

Sq.Ft.

316 TROPIC DRIVE

Osprey, FL

Courtesy of COLDWELL BANKER SARASOTA CENT.
View 238 WOODLAND DRIVE 238 Osprey, FL MLS# N6140863
$184,900
1

Beds

1.1

Baths

865

Sq.Ft.

238 WOODLAND DRIVE 238

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 2/21/2026.