Osprey Luxury Homes for Sale · Page 2
47 luxury homes for sale in Osprey, median asking price $1,750,000, mostly $1,100,000 – $4,670,000. Homes with an asking price of $1M or more. Osprey (ZIP 34229). Nokomis has its own page. As of Oct 9, 2026.
$2,750,000
447 MACEWEN DRIVE
OSPREY, FL 34229
MLS# A4703990 · Listing courtesy of COLDWELL BANKER REALTY
$1,800,000
222 SAINT JAMES PARK
OSPREY, FL 34229
MLS# A4703804 · Listing courtesy of COLDWELL BANKER REALTY
$1,690,000
206 FOUR KNOT LANE
OSPREY, FL 34229
MLS# A4695429 · Listing courtesy of REALTY ONE GROUP MVP
$1,595,000
75 OSPREY POINT DRIVE
OSPREY, FL 34229
MLS# A4695145 · Listing courtesy of COLDWELL BANKER REALTY
$1,495,000
360 N POINT ROAD
OSPREY, FL 34229
MLS# A4695959 · Listing courtesy of COLDWELL BANKER REALTY
$4,790,000
101 OSPREY POINT DRIVE
OSPREY, FL 34229
MLS# A4694716 · Listing courtesy of DOUGLAS ELLIMAN
$1,289,000
156 BISHOPS COURT ROAD
OSPREY, FL 34229
MLS# A4691664 · Listing courtesy of DOUGLAS ELLIMAN
$3,295,000
135 TINA ISLAND DRIVE
OSPREY, FL 34229
MLS# A4692366 · Listing courtesy of GENEROUS PROPERTY
$1,950,000
97 SUGAR MILL DRIVE
OSPREY, FL 34229
MLS# A4691789 · Listing courtesy of PALM PARADISE REALTY GROUP
$1,100,000
1527 BUOY LANE
OSPREY, FL 34229
MLS# A4688266 · Listing courtesy of BRIGHT REALTY
$5,299,999
313 LOOKOUT POINT DRIVE
OSPREY, FL 34229
MLS# A4688995 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
$2,850,000
14401 MASTHEAD DRIVE
OSPREY, FL 34229
MLS# A4684834 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
$1,995,000
401 POINT ROAD #1001
OSPREY, FL 34229
MLS# A4679998 · Listing courtesy of GENEROUS PROPERTY
$1,100,000
385 N POINT ROAD #304
OSPREY, FL 34229
MLS# A4678422 · Listing courtesy of GENEROUS PROPERTY
$2,399,000
49 OSPREY POINT DRIVE
OSPREY, FL 34229
MLS# A4671762 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
$1,950,000
538 DOVE POINTE DRIVE
OSPREY, FL 34229
MLS# A4669491 · Listing courtesy of GENEROUS PROPERTY
$1,750,000
18 CASEY KEY ROAD
OSPREY, FL 34229
MLS# A4669083 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY
$6,100,000
121 CASEY KEY ROAD
OSPREY, FL 34229
MLS# A4667263 · Listing courtesy of DOUGLAS ELLIMAN
$2,395,000
852 MACEWEN DRIVE
OSPREY, FL 34229
MLS# A4659276 · Listing courtesy of GENEROUS PROPERTY
$2,700,000
236 SAINT JAMES PARK
OSPREY, FL 34229
MLS# A4644125 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
$1,395,000
3603 POINT ROAD #702
OSPREY, FL 34229
MLS# A4642397 · Listing courtesy of GENEROUS PROPERTY
$1,595,000
909 MACEWEN DRIVE
OSPREY, FL 34229
MLS# A4621683 · Listing courtesy of GENEROUS PROPERTY
$1,900,000
168 COASTAL HAMMOCK COURT
OSPREY, FL 34229
MLS# A4707893 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
More in Osprey
Luxury Homes for Sale nearby
Questions about Osprey Luxury Homes for Sale
How many luxury homes are for sale in Osprey?
47 luxury homes are listed on this site as of Oct 9, 2026, from Stellar MLS. The list updates every hour.
What is the median asking price of luxury homes in Osprey?
The median asking price is $1,750,000; most are listed between $1,100,000 and $4,670,000. These are asking prices, not sale prices.
Can George help me buy in Osprey?
Yes. George Predescu, REALTOR® with Horizon Realty International, can set up showings for any listing here, including ones listed by other brokers. Call or text (941) 899-3045.
Want to see one of these luxury homes?
George Predescu, REALTOR® with Horizon Realty International, can answer questions and set up showings.
Listings courtesy of Stellar MLS as distributed by MLS GRID
Based on information submitted to the MLS GRID as of Oct 9, 2026, 4:30 PM EDT. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively 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. Some IDX listings have been excluded from this website. Full IDX / DMCA disclaimer