Osprey, FL 34229 Homes For Sale
124 listings. Live MLS data, refreshed nightly. Osprey market overview
34229
Get alerts on new listings
We'll email you when new homes match these filters. No spam, unsubscribe anytime.
Loading map…
Listings
$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
$115,000
570 BLACKBURN POINT RD #43
OSPREY, 34229
313 days on market
Waterfront
Listed by David Babel, BRIGHT REALTY
$109,000
570 BLACKBURN POINT RD #13
OSPREY, 34229
314 days on market
Waterfront
Listed by David Babel, BRIGHT REALTY
$1,095,000
403 LONGBOW TRL
OSPREY, 34229
4 bd·3 ba·2,770 sqft
283 days on market
Pool
Listed by Edward Bieker, PA, DALTON WADE INC
$2,199,900
180 LOOKOUT POINT DR
OSPREY, 34229
5 bd·3.5 ba·3,236 sqft
287 days on market
Pool
Listed by Katy McBrayer, PREMIER SOTHEBY'S INTERNATIONAL REALTY
$2,399,000
49 OSPREY POINT DR
OSPREY, 34229
4 bd·3.5 ba·3,953 sqft
335 days on market
WaterfrontPool
Listed by MICHAEL SAUNDERS & COMPANY
$2,850,000
141 N CASEY KEY RD
OSPREY, 34229
191 days on market
Waterfront
Listed by Julie Larson, LLC, WHITE SANDS REALTY GROUP FL
$399,000
1811 HIGHLAND RD
OSPREY, 34229
2 bd·2 ba·1,725 sqft
356 days on market
Listed by Stephen Hachey, REALTY OF RIVERVIEW LLC
$104,900
348 TROPIC DR
OSPREY, 34229
2 bd·2 ba·864 sqft
317 days on market
Listed by John Alexander, FINE PROPERTIES
$6,100,000
121 N CASEY KEY RD
OSPREY, 34229
4 bd·5.5 ba·4,096 sqft
366 days on market
WaterfrontPool
Listed by DOUGLAS ELLIMAN
$789,000
21 BAYHEAD LN
OSPREY, 34229
3 bd·2 ba·2,246 sqft
364 days on market
Pool
Listed by Steve Abbe, COLDWELL BANKER REALTY
$815,000
599 PINE RANCH EAST RD
OSPREY, 34229
3 bd·2 ba·2,188 sqft
348 days on market
Pool
Listed by Mark Lyda, GENEROUS PROPERTY
$2,395,000
852 MACEWEN DR
OSPREY, 34229
3 bd·3.5 ba·4,519 sqft
444 days on market
Pool
Listed by Mark Lyda, GENEROUS PROPERTY
$39,500
570 BLACKBURN POINT RD #11
OSPREY, 34229
345 days on market
Listed by Daniel Treiman, MICHAEL SAUNDERS & COMPANY
$599,000
110 PINE AVE
OSPREY, 34229
3 bd·2 ba·2,058 sqft
559 days on market
Pool
Listed by Marisa Marino, BRIGHT REALTY
$769,000
13 BAYHEAD LN
OSPREY, 34229
3 bd·2 ba·2,310 sqft
545 days on market
Pool
Listed by Mark Lyda, GENEROUS PROPERTY
$2,700,000
236 SAINT JAMES PARK
OSPREY, 34229
6 bd·6.5 ba·6,246 sqft
405 days on market
Pool
Listed by MICHAEL SAUNDERS & COMPANY
$1,395,000
3603 N POINT RD #702
OSPREY, 34229
3 bd·3 ba·2,545 sqft
552 days on market
Waterfront
Listed by Mark Lyda, GENEROUS PROPERTY
New
$2,395,000
140 N CASEY KEY RD
OSPREY, 34229
3 bd·3.5 ba·2,473 sqft
0 days on market
WaterfrontPool
Listed by Rhonda Carder, KELLER WILLIAMS ON THE WATER
New
$275,000
308 PINE RUN DR
OSPREY, 34229
2 bd·1.5 ba·1,184 sqft
1 day on market
Listed by Priscilla Adams, COMPASS FLORIDA LLC
$615,000
385 N POINT RD #402
OSPREY, 34229
3 bd·3 ba·2,055 sqft
586 days on market
Listed by Mark Lyda, GENEROUS PROPERTY
$875,000
293 TURQUOISE LN
OSPREY, 34229
3 bd·2 ba·2,271 sqft
601 days on market
Listed by Mark Lyda, GENEROUS PROPERTY
Listing data provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last sample-row update: September 20, 2026. Information herein deemed reliable but not guaranteed. Equal Housing Opportunity.