Real Estate Investment Properties for Sale in Osprey, FL
Looking for investment property in Osprey, FL with high ROI ?
Explore a variety of short-term homes & houses in Osprey, FL. Invest wisely with VRBO & Osprey, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Osprey, FL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
226 Saint James ParkOSPREY, FLLocated inside the gates of The Oaks Club, this 3 bedroom 2.5 bathroom home offers an exce... |
3 beds | 2 baths | 2,591 sq.ft. |
$1,495,000 |
Airbnb cash on cash: -0.34%
|
403 LONGBOW TrailOSPREY, FLWelcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in o... |
4 beds | 3 baths | 2,770 sq.ft. |
$1,095,000 |
Airbnb cash on cash: 2.07%
|
14021 Bellagio Way #404OSPREY, FLThis beautifully remodeled waterfront condominium in Osprey offers a blend of luxury, comf... |
3 beds | 3 baths | 2,187 sq.ft. |
$999,900 |
Airbnb cash on cash: -1.34%
|
780 Sarabay Rd #16OSPREY, FLWaterfront Villa w/BOAT SLIPS - Large Private Courtyard & 2- Car Garage - Maintenance Free... |
2 beds | 2 baths | 1,574 sq.ft. |
$425,000 |
Airbnb cash on cash: -2.69%
|
222 SAINT JAMES ParkOSPREY, FLBeautifully maintained Arthur Rutenberg 3 bedroom, 3.5 bath home located on a quiet cul-de... |
3 beds | 4 baths | 3,665 sq.ft. |
$1,800,000 |
Airbnb cash on cash: -0.57%
|
447 E MACEWEN DriveOSPREY, FLExperience refined living in this extraordinary, elegant home. With 3 bedrooms and 4.5 bat... |
4 beds | 5 baths | 5,323 sq.ft. |
$2,750,000 |
Airbnb cash on cash: -0.13%
|
75 Osprey Point DrOSPREY, FLOffered at a price approaching the value of the two buildable lots alone, this architect-d... |
4 beds | 4 baths | 4,001 sq.ft. |
$1,595,000 |
Airbnb cash on cash: 0.08%
|
110 Pine AveOSPREY, FLHeart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your... |
3 beds | 2 baths | 2,058 sq.ft. |
$649,000 |
Airbnb cash on cash: 1.4%
|
401 N POINT Road #701OSPREY, FLEnjoy luxury living at its finest in this beautiful 3 bedroom, 3 bath residence with a PRI... |
3 beds | 3 baths | 2,594 sq.ft. |
$1,480,000 |
Airbnb cash on cash: -0.68%
|
154 Lookout Point DrOSPREY, FLWelcome to exceptional Florida living in the highly sought-after Southbay Yacht & Racquet ... |
4 beds | 3 baths | 4,578 sq.ft. |
$2,199,999 |
Airbnb cash on cash: 0.34%
|
299 Turquoise LnOSPREY, FLRemarkable 3 bedroom 2 bathroom home in Emerald Woods now available for purchase. Nestled ... |
3 beds | 2 baths | 2,328 sq.ft. |
$719,000 |
Airbnb cash on cash: -0.54%
|
401 N POINT Road #304OSPREY, FLGive yourself the gift of refined living in this expansive 2,778 square foot residence-the... |
3 beds | 3 baths | 2,778 sq.ft. |
$695,000 |
Airbnb cash on cash: -2.55%
|
292 TURQUOISE LaneOSPREY, FLhis stunning, updated home sits on a corner lot; the largest in Emerald Woods. Located beh... |
3 beds | 2 baths | 2,255 sq.ft. |
$1,050,000 |
Airbnb cash on cash: -0.03%
|
108 Villa Dr #108OSPREY, FLCome for the investment, stay for the lifestyle! Discover an exceptional waterfront opport... |
2 beds | 2 baths | 1,593 sq.ft. |
$299,950 |
Airbnb cash on cash: 2.47%
|
180 LOOKOUT POINT DriveOSPREY, FLVirtually Staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & ... |
5 beds | 4 baths | 3,236 sq.ft. |
$2,199,900 |
Airbnb cash on cash: N/A
|
4428 Conchfish LnOSPREY, FLChic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located ... |
4 beds | 2 baths | 1,861 sq.ft. |
$525,000 |
Airbnb cash on cash: 5.7%
|
401 N Point Rd #301OSPREY, FLVirtually Staged. Short Sale. Enter through the secure foyer and take the private elevator... |
3 beds | 3 baths | 2,594 sq.ft. |
$459,900 |
Airbnb cash on cash: -2.97%
|
759 Fordingbridge WayOSPREY, FLDiscover this stunning home located in the heart of Osprey, FL. Featuring a spacious layou... |
4 beds | 3 baths | 2,950 sq.ft. |
$700,000 |
Airbnb cash on cash: 4.03%
|
3621 N Point Rd #301OSPREY, FLReady to live a stress-free luxury condo lifestyle? There is no place better to do it than... |
3 beds | 3 baths | 2,680 sq.ft. |
$525,000 |
Airbnb cash on cash: -2.27%
|
280 Hidden Bay Dr #302OSPREY, FLMove right in and enjoy refined coastal living in this brand-new condominium at Edgewater ... |
3 beds | 2 baths | 1,937 sq.ft. |
$719,000 |
Airbnb cash on cash: -1.6%
|
401 N Point Rd #603OSPREY, FLVirtually Staged. This incredible offering has everything you need to live a luxury condom... |
3 beds | 3 baths | 2,203 sq.ft. |
$629,000 |
Airbnb cash on cash: -2.06%
|
360 N Point RdOSPREY, FLVirtually Staged. A unique offering! This like-new, never lived in Spanish mission style h... |
3 beds | 3 baths | 2,913 sq.ft. |
$1,495,000 |
Airbnb cash on cash: -0.52%
|
18 N Casey Key RdOSPREY, FLUnder contract-accepting backup offers. Elegantly renovated bayfront retreat on Casey Key ... |
3 beds | 2 baths | 1,977 sq.ft. |
$1,750,000 |
Airbnb cash on cash: -1.16%
|
14021 BELLAGIO Way #309OSPREY, FLEnjoy breathtaking sunset views overlooking the intercostal waterway in this boater's para... |
3 beds | 3 baths | 2,199 sq.ft. |
$899,995 |
Airbnb cash on cash: -1.72%
|
1216 N Casey Key RdOSPREY, FLAt the northernmost point of Casey Key, where the Gulf meets the tranquil waters of Little... |
5 beds | 6 baths | 8,050 sq.ft. |
$9,750,000 |
Airbnb cash on cash: -0.93%
|
4226 FRONTIER Lane #103OSPREY, FLCoastal convenience meets effortless living, just minutes from Siesta Key, America's #1 be... |
2 beds | 2 baths | 1,135 sq.ft. |
$299,000 |
Airbnb cash on cash: 1.68%
|
320 Tropic DrOSPREY, FLVirtually Staged. Welcome to this Partially Furnished home in the desirable 55+ cooperativ... |
2 beds | 2 baths | 1,199 sq.ft. |
$185,000 |
Airbnb cash on cash: 4.39%
|
1527 Buoy LnOSPREY, FLBeautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet... |
3 beds | 2 baths | 2,830 sq.ft. |
$1,165,000 |
Airbnb cash on cash: -0.09%
|
51 Mac Ewen Dr #14OSPREY, FLThis completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge... |
1 beds | 1 baths | 595 sq.ft. |
$285,000 |
Airbnb cash on cash: -2.13%
|
21 Bayhead LnOSPREY, FLLooking for a home you can truly fall in love with? Your search ends here. This thoughtful... |
3 beds | 2 baths | 2,246 sq.ft. |
$789,000 |
Airbnb cash on cash: -0.11%
|
6100 Jessie Harbor Dr #202OSPREY, FLOne or more photo(s) has been virtually staged. PRICE IMPROVED OVER $50K!!!! Experience el... |
3 beds | 3 baths | 3,771 sq.ft. |
$798,000 |
Airbnb cash on cash: -1.04%
|
260 HIDDEN BAY DRIVE 304OSPREY, FLThe Boca Residence: Spacious Living & Resort Style Discover a condominium that offers the... |
2 beds | 3 baths | 1,950 sq.ft. |
$694,000 |
Airbnb cash on cash: -2.07%
|
1140 Beachcomber Ct #11OSPREY, FLVirtually Staged. Welcome to Blackburn Point Marina Village, an intimate gated waterfront ... |
3 beds | 2 baths | 2,040 sq.ft. |
$540,000 |
Airbnb cash on cash: -0.42%
|
107 SORRENTO DriveOSPREY, FLThis beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an... |
2 beds | 2 baths | 1,284 sq.ft. |
$425,000 |
Airbnb cash on cash: 2.42%
|
Real Estate investment in Osprey, FL
There are 99 properties for sale in the city of Osprey . The median list price in Osprey is $749,504 and the average price per square foot is $327. In October 2026, the average monthly cash on cash return in Osprey is 3.00%. The average monthly rental income in Osprey is $3,490.