Property listings in Osprey, South Bay

MLS® #: A4616676

MLS #A4616676 image #0

505 LUMINARY BOULEVARD
OSPREY FL 34229
$7,499,000
Beds | Baths | 4,000 SqFt
10.01 Acres

MLS® #: A4667263

MLS #A4667263 image #0

121 N CASEY KEY ROAD
OSPREY FL 34229
$6,475,000
5 Beds | 5.5 Baths | 4,096 SqFt
0.49 Acres

MLS® #: A4688995

MLS #A4688995 image #0

313 LOOKOUT POINT DRIVE
OSPREY FL 34229
$5,999,999
4 Beds | 4.5 Baths | 5,337 SqFt
0.41 Acres

MLS® #: A4694716

MLS #A4694716 image #0

101 POINT DRIVE
OSPREY FL 34229
$4,790,000
4 Beds | 5.5 Baths | 5,087 SqFt
0.93 Acres

MLS® #: A4683138

MLS #A4683138 image #0

324 BAYSHORE DRIVE
OSPREY FL 34229
$3,995,000
4 Beds | 4.5 Baths | 4,389 SqFt
0.47 Acres

MLS® #: A4668918

MLS #A4668918 image #0

854 MACEWEN DRIVE
OSPREY FL 34229
$3,640,000
4 Beds | 5 Baths | 9,081 SqFt
0.78 Acres

MLS® #: A4692366

MLS #A4692366 image #0

135 TINA ISLAND DRIVE
OSPREY FL 34229
$3,295,000
3 Beds | 4.5 Baths | 2,572 SqFt
0.37 Acres

MLS® #: A4697345

MLS #A4697345 image #0

321 LOOKOUT POINT DRIVE
OSPREY FL 34229
$3,100,000
3 Beds | 3.5 Baths | 3,122 SqFt
0.34 Acres

MLS® #: A4684834

MLS #A4684834 image #0

14401 MASTHEAD DRIVE
OSPREY FL 34229
$2,995,000
3 Beds | 3.5 Baths | 2,665 SqFt
0.44 Acres

MLS® #: A4669513

MLS #A4669513 image #0

141 N CASEY KEY ROAD
OSPREY FL 34229
$2,850,000
Beds | Baths | SqFt
0.39 Acres

MLS® #: A4644125

MLS #A4644125 image #0

236 SAINT JAMES PARK
OSPREY FL 34229
$2,700,000
6 Beds | 6.5 Baths | 6,246 SqFt
0.56 Acres

MLS® #: A4688291

MLS #A4688291 image #0

449 WEBBS COVE
OSPREY FL 34229
$2,650,000
4 Beds | 3.5 Baths | 5,287 SqFt
0.39 Acres

MLS® #: A4671762

MLS #A4671762 image #0

49 POINT DRIVE
OSPREY FL 34229
$2,399,000
4 Beds | 3.5 Baths | 3,953 SqFt
0.4 Acres

MLS® #: A4659276

MLS #A4659276 image #0

852 MACEWEN DRIVE
OSPREY FL 34229
$2,395,000
3 Beds | 3.5 Baths | 4,519 SqFt
0.64 Acres

MLS® #: A4676567

MLS #A4676567 image #0

362 MACEWEN DRIVE
OSPREY FL 34229
$2,249,000
4 Beds | 3.5 Baths | 4,117 SqFt
0.59 Acres

MLS® #: A4672222

MLS #A4672222 image #0

180 LOOKOUT POINT DRIVE
OSPREY FL 34229
$2,199,900
5 Beds | 3.5 Baths | 3,236 SqFt
0.4 Acres

MLS® #: A4676505

MLS #A4676505 image #0

433 E MACEWEN DRIVE
OSPREY FL 34229
$2,189,000
4 Beds | 3.5 Baths | 4,012 SqFt
0.61 Acres

MLS® #: A4687195

MLS #A4687195 image #0

448 E MACEWEN DRIVE
OSPREY FL 34229
$2,100,000
4 Beds | 3.5 Baths | 3,768 SqFt
0.59 Acres

MLS® #: A4679998

MLS #A4679998 image #0

401 N POINT ROAD UNIT 1001
OSPREY FL 34229
$1,995,000
3 Beds | 3 Baths | 3,029 SqFt
0 Acres

MLS® #: A4669491

MLS #A4669491 image #0

538 DOVE POINTE DRIVE
OSPREY FL 34229
$1,950,000
4 Beds | 5.5 Baths | 4,346 SqFt
0.83 Acres

MLS® #: A4691789

MLS #A4691789 image #0

97 SUGAR MILL DRIVE
OSPREY FL 34229
$1,950,000
5 Beds | 5.5 Baths | 4,885 SqFt
0.4 Acres

MLS® #: A4695429

MLS #A4695429 image #0

206 FOUR KNOT LANE
OSPREY FL 34229
$1,850,000
3 Beds | 2 Baths | 2,411 SqFt
0.3 Acres

MLS® #: 226021461

MLS #226021461 image #0

206 Four Knot LN
OSPREY FL 34229
$1,850,000
3 Beds | 2 Baths | 2,411 SqFt
0.3 Acres

The data relating to real estate for sale on this site comes from Stellar MLS. All properties are subject to prior sale, changes, or withdrawal.
This site was last updated Jul-02-2026 4:44:58 am.

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Naples, FL. All properties are subject to prior sale, changes, or withdrawal.