Osprey Waterfront Homes for Sale · Page 2
40 waterfront homes for sale in Osprey, median asking price $763,000, mostly $226,000 – $4,841,000. Homes the MLS marks as waterfront (Gulf, bay, canal, lake or river). Osprey (ZIP 34229). Nokomis has its own page. As of Oct 9, 2026.
$798,000
6100 JESSIE HARBOR DRIVE #202
OSPREY, FL 34229
MLS# A4690969 · Listing courtesy of CORCORAN DWELLINGS REALTY
$999,900
14021 BELLAGIO WAY #404
OSPREY, FL 34229
MLS# N6144070 · Listing courtesy of PREMIER SOTHEBYS INTL REALTY
$699,000
5100 JESSIE HARBOR DRIVE #304
OSPREY, FL 34229
MLS# A4690942 · Listing courtesy of COLDWELL BANKER REALTY
$235,000
51 MACEWEN DRIVE #5
OSPREY, FL 34229
MLS# A4689838 · Listing courtesy of 342 REAL ESTATE
$700,000
14041 BELLAGIO WAY #214
OSPREY, FL 34229
MLS# A4689731 · Listing courtesy of COLDWELL BANKER 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
$879,000
14021 BELLAGIO WAY #309
OSPREY, FL 34229
MLS# A4681589 · Listing courtesy of COMPASS FLORIDA, LLC
$700,000
242 HIDDEN BAY DRIVE #602
OSPREY, FL 34229
MLS# A4678883 · Listing courtesy of FIRST LIGHT REAL ESTATE
$115,000
570 BLACKBURN POINT ROAD #43
OSPREY, FL 34229
MLS# A4672823 · Listing courtesy of BRIGHT REALTY
$109,000
570 BLACKBURN POINT ROAD #13
OSPREY, FL 34229
MLS# A4674344 · Listing courtesy of BRIGHT REALTY
$2,399,000
49 OSPREY POINT DRIVE
OSPREY, FL 34229
MLS# A4671762 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
$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
$1,395,000
3603 POINT ROAD #702
OSPREY, FL 34229
MLS# A4642397 · 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
Waterfront Homes for Sale nearby
Questions about Osprey Waterfront Homes for Sale
How many waterfront homes are for sale in Osprey?
40 waterfront 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 waterfront homes in Osprey?
The median asking price is $763,000; most are listed between $226,000 and $4,841,000. 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 waterfront 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