Osprey Waterfront Homes for Sale
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.
$465,000
120 VILLA DRIVE #120
OSPREY, FL 34229
MLS# A4708477 · Listing courtesy of MANGROVE REALTY ASSOCIATES
$625,000
250 HIDDEN BAY DRIVE #302
OSPREY, FL 34229
MLS# A4706421 · Listing courtesy of COLDWELL BANKER REALTY
$4,590,000
275 LOOKOUT POINT DRIVE
OSPREY, FL 34229
MLS# A4707430 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
$995,000
256 TURQUOISE LANE
OSPREY, FL 34229
MLS# A4707269 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
$629,400
3603 POINT ROAD #202
OSPREY, FL 34229
MLS# A4707579 · Listing courtesy of GENEROUS PROPERTY
$540,000
1346 THORNAPPLE DRIVE
OSPREY, FL 34229
MLS# A4707282 · Listing courtesy of RE/MAX ALLIANCE GROUP
$679,000
33 BISHOPS COURT ROAD #118
OSPREY, FL 34229
MLS# A4707242 · Listing courtesy of GENEROUS PROPERTY
$3,700,000
324 OSPREY POINT DRIVE
OSPREY, FL 34229
MLS# A4706333 · Listing courtesy of COLDWELL BANKER REALTY
$750,000
385 N POINT ROAD #301
OSPREY, FL 34229
MLS# A4706542 · Listing courtesy of COLDWELL BANKER REALTY
$669,900
130 WILLOW BEND WAY
OSPREY, FL 34229
MLS# TB8548160 · Listing courtesy of RE/MAX ALLIANCE GROUP
$749,900
1328 THORNAPPLE DRIVE
OSPREY, FL 34229
MLS# A4705435 · Listing courtesy of RIVER HILLS PROPERTIES, LLC B
$565,000
2046 CORDES STREET
OSPREY, FL 34229
MLS# A4705136 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
$1,250,000
401 N POINT ROAD #903
OSPREY, FL 34229
MLS# A4705080 · Listing courtesy of COLDWELL BANKER REALTY
$6,449,000
112 OSPREY POINT DRIVE
OSPREY, FL 34229
MLS# A4702047 · Listing courtesy of DOUGLAS ELLIMAN
$9,750,000
1216 CASEY KEY ROAD
OSPREY, FL 34229
MLS# A4704643 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY
$2,750,000
447 MACEWEN DRIVE
OSPREY, FL 34229
MLS# A4703990 · Listing courtesy of COLDWELL BANKER REALTY
$599,000
5100 JESSIE HARBOR DRIVE #404
OSPREY, FL 34229
MLS# A4703484 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
$775,000
260 HIDDEN BAY DRIVE #402
OSPREY, FL 34229
MLS# A4701000 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY
$99,500
570 BLACKBURN POINT ROAD #36
OSPREY, FL 34229
MLS# A4700865 · Listing courtesy of BRIGHT REALTY
$395,000
7204 JESSIE HARBOR DRIVE #7204
OSPREY, FL 34229
MLS# A4697473 · Listing courtesy of GENEROUS PROPERTY
$4,790,000
101 OSPREY POINT DRIVE
OSPREY, FL 34229
MLS# A4694716 · Listing courtesy of DOUGLAS ELLIMAN
$275,000
51 MACEWEN DRIVE #12
OSPREY, FL 34229
MLS# A4690540 · Listing courtesy of COLDWELL BANKER REALTY
$3,295,000
135 TINA ISLAND DRIVE
OSPREY, FL 34229
MLS# A4692366 · Listing courtesy of GENEROUS PROPERTY
$798,000
6100 JESSIE HARBOR DRIVE #202
OSPREY, FL 34229
MLS# A4690969 · Listing courtesy of CORCORAN DWELLINGS REALTY
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, 3:15 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