192 total properties
View 433 E MACEWEN DRIVE Osprey, FL MLS# A4676505
  • 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 362 MACEWEN DRIVE Osprey, FL MLS# A4676567
  • Virtual Tour
1 of 55
$2,249,000
4

Beds

3.1

Baths

4,117

Sq.Ft.

362 MACEWEN DRIVE

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 600 EAGLE WATCH LANE Osprey, FL MLS# A4668497
$2,195,000
3

Beds

3.0

Baths

3,681

Sq.Ft.

600 EAGLE WATCH LANE

Osprey, FL

Courtesy of GENEROUS PROPERTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 85 SUGAR MILL DRIVE Osprey, FL MLS# A4667740
  • Virtual Tour
1 of 76
$2,150,000
3

Beds

3.0

Baths

4,191

Sq.Ft.

85 SUGAR MILL DRIVE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 140 N CASEY KEY ROAD Osprey, FL MLS# A4665482
$2,100,000
3

Beds

3.1

Baths

2,473

Sq.Ft.

140 N CASEY KEY ROAD

Osprey, FL

Courtesy of EXP REALTY LLC
View 538 DOVE POINTE DRIVE Osprey, FL MLS# A4669491
  • Virtual Tour
1 of 75
$2,100,000
4

Beds

5.1

Baths

4,346

Sq.Ft.

538 DOVE POINTE DRIVE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 312 YACHT HARBOR DRIVE Osprey, FL MLS# A4667293
  • Virtual Tour
1 of 68
OPEN HOUSE: Sunday 2/22 1:00 PM - 4:00 PM
$1,995,000
4

Beds

4.0

Baths

2,572

Sq.Ft.

312 YACHT HARBOR DRIVE

Osprey, FL

Courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY
View 401 N POINT ROAD 1001 Osprey, FL MLS# A4679998
  • Recently Listed with Virtual Tour
1 of 60
$1,995,000
3

Beds

3.0

Baths

3,029

Sq.Ft.

401 N POINT ROAD 1001

Osprey, FL

Courtesy of GENEROUS PROPERTY
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 401 WALLS WAY Osprey, FL MLS# A4680312
  • Virtual Tour
1 of 51
$1,800,000
4

Beds

3.1

Baths

4,387

Sq.Ft.

401 WALLS WAY

Osprey, FL

Courtesy of ENGEL + VOELKERS SARASOTA
View 75 OSPREY POINT DRIVE Osprey, FL MLS# A4672439
  • Virtual Tour
1 of 92
$1,775,000
4

Beds

4.0

Baths

4,001

Sq.Ft.

75 OSPREY POINT DRIVE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 909 MACEWEN DRIVE Osprey, FL MLS# A4621683
  • Virtual Tour
1 of 62
$1,695,000
3

Beds

3.1

Baths

4,241

Sq.Ft.

909 MACEWEN DRIVE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 25 SUGAR MILL DRIVE Osprey, FL MLS# A4678423
  • Virtual Tour
1 of 74
$1,695,000
3

Beds

3.1

Baths

3,066

Sq.Ft.

25 SUGAR MILL DRIVE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 422 BLUE GARDEN LANE Osprey, FL MLS# A4664436
  • Virtual Tour
1 of 100
$1,650,000
3

Beds

3.1

Baths

3,872

Sq.Ft.

422 BLUE GARDEN LANE

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 76 OSPREY POINT DRIVE Osprey, FL MLS# A4672843
  • Virtual Tour
1 of 98
$1,650,000
3

Beds

4.1

Baths

4,364

Sq.Ft.

76 OSPREY POINT DRIVE

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 3983 DESTINATION DRIVE 102-202 Osprey, FL MLS# TB8428492
$1,600,000
3,871

Sq.Ft.

3983 DESTINATION DRIVE 102-202

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 20 BAYHEAD LANE Osprey, FL MLS# A4674649
  • Virtual Tour
1 of 63
OPEN HOUSE: Sunday 2/22 1:00 PM - 4:00 PM
$1,575,000
4

Beds

3.0

Baths

3,486

Sq.Ft.

20 BAYHEAD LANE

Osprey, FL

Courtesy of EXP REALTY LLC
View 360 N POINT ROAD Osprey, FL MLS# A4617671
  • New Construction with Virtual Tour
1 of 57
$1,570,000
3

Beds

3.1

Baths

2,913

Sq.Ft.

360 N POINT ROAD

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 385 N POINT ROAD 704 Osprey, FL MLS# A4671431
  • Virtual Tour
1 of 96
$1,500,000
3

Beds

3.0

Baths

2,778

Sq.Ft.

385 N POINT ROAD 704

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 2099 S TAMIAMI TRAIL Osprey, FL MLS# A4677875
  • Virtual Tour
1 of 16
$1,400,000
Studio

Beds

0.0

Baths

2099 S TAMIAMI TRAIL

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 2/22/2026.