Osprey, FL Homes For Sale
121 listings. Live MLS data, refreshed nightly. Osprey market overview
Osprey, FL
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Listings
$1,950,000
97 SUGAR MILL DR
OSPREY, 34229
5 bd·5.5 ba·4,885 sqft
141 days on market
Pool
Listed by PALM PARADISE REALTY GROUP
$499,999
4429 CONCHFISH LN
OSPREY, 34229
3 bd·2 ba·2,004 sqft
147 days on market
Listed by Jennifer Kenna, EXP REALTY, LLC
$999,900
14021 BELLAGIO WAY #404
OSPREY, 34229
3 bd·3 ba·2,187 sqft
163 days on market
Waterfront
Listed by Megan E. George, PA, PREMIER SOTHEBYS INTL REALTY
$560,000
409 NORTH POINT RD #401
OSPREY, 34229
3 bd·3 ba·2,594 sqft
135 days on market
Listed by Steve Abbe, COLDWELL BANKER REALTY
$285,000
51 MAC EWEN DR #14
OSPREY, 34229
1 bd·1 ba·595 sqft
136 days on market
Listed by Steve Abbe, COLDWELL BANKER REALTY
$235,000
51 MACEWEN DR #5
OSPREY, 34229
1 bd·1 ba·595 sqft
21 days on market
Waterfront
$700,000
759 FORDINGBRIDGE WAY
OSPREY, 34229
4 bd·3.5 ba·2,950 sqft
119 days on market
Pool
Listed by Steven Koleno, BEYCOME OF FLORIDA LLC
$700,000
14041 BELLAGIO WAY #214
OSPREY, 34229
3 bd·2 ba·1,799 sqft
169 days on market
Waterfront
Listed by Veronica Lee, COLDWELL BANKER REALTY
$5,299,999
313 LOOKOUT POINT DR
OSPREY, 34229
4 bd·4.5 ba·5,337 sqft
196 days on market
WaterfrontPool
Listed by Natalie Gutwein, MICHAEL SAUNDERS & COMPANY
$1,100,000
1527 BUOY LN
OSPREY, 34229
3 bd·2.5 ba·2,830 sqft
176 days on market
Pool
Listed by Matthew Lewis, BRIGHT REALTY
$425,000
107 SORRENTO DR
OSPREY, 34229
2 bd·2 ba·1,284 sqft
163 days on market
Listed by Crystal Cosby, LLC, PREMIER SOTHEBYS INTL REALTY
$175,000
14 OLD VENICE RD
OSPREY, 34229
133 days on market
Listed by Mousa Wakileh, COLDWELL BANKER REALTY
$36,000
570 BLACKBURN POINT RD #26
OSPREY, 34229
250 days on market
Listed by David Babel, BRIGHT REALTY
$999,000
2099 S TAMIAMI TRL
OSPREY, 34229
250 days on market
Listed by Sue Repp, COLDWELL BANKER REALTY
$879,000
14021 BELLAGIO WAY #309
OSPREY, 34229
3 bd·2.5 ba·2,199 sqft
177 days on market
Waterfront
Listed by Tristin Hopler, COMPASS FLORIDA, LLC
$525,000
3621 N POINT RD #301
OSPREY, 34229
3 bd·3 ba·2,680 sqft
211 days on market
Listed by Steve Abbe, COLDWELL BANKER REALTY
$1,250,000
409 N POINT RD #601
OSPREY, 34229
3 bd·3 ba·2,594 sqft
239 days on market
Listed by Mark Lyda, GENEROUS PROPERTY
$1,995,000
401 N POINT RD #1001
OSPREY, 34229
3 bd·3 ba·3,029 sqft
214 days on market
Listed by Mark Lyda, GENEROUS PROPERTY
$700,000
242 HIDDEN BAY DR #602
OSPREY, 34229
2 bd·2 ba·1,932 sqft
235 days on market
Waterfront
Listed by Cathy Rustin, FIRST LIGHT REAL ESTATE
New
$699,000
410 BLUE GARDEN LN
OSPREY, 34229
0 days on market
Listed by ELITE PROPERTIES LLC
$1,100,000
385 N POINT RD #304
OSPREY, 34229
3 bd·3 ba·2,778 sqft
230 days on market
Listed by Mark Lyda, GENEROUS PROPERTY
$409,000
3976 DESTINATION DR #102
OSPREY, 34229
1,050 sqft
247 days on market
Listed by Kelley Ann Ayers, AYERS AND ASSOCIATES REAL ESTATE
$999,000
2099 S TAMIAMI TRL
OSPREY, 34229
278 days on market
Listed by Sue Repp, COLDWELL BANKER REALTY
$419,000
524 SARABAY RD
OSPREY, 34229
3 bd·2 ba·1,760 sqft
197 days on market
Listed by Ibett Giannone
Listing data provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last sample-row update: September 19, 2026. Information herein deemed reliable but not guaranteed. Equal Housing Opportunity.