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 |
|---|---|---|---|
854 MACEWEN DRIVEOSPREY, FLOne or more photo(s) has been virtually staged. Set on a private cul-de-sac within The Oak... |
4 beds | 6 baths | 9,081 sq.ft. |
$3,790,000 |
Airbnb cash on cash: -0.04%
|
730 SARABAY ROADOSPREY, FLOne or more photo(s) has been virtually staged. PREMIER HIGH-ELEVATION BAYFRONT ESTATE ON ... |
4 beds | 6 baths | 6,308 sq.ft. |
$4,995,000 |
Airbnb cash on cash: -0.66%
|
1303 THORNAPPLE DRIVEOSPREY, FLUnder contract-accepting backup offers. INCREDIBLE Pool Home in INCREDIBLE Community!...Yo... |
3 beds | 2 baths | 1,929 sq.ft. |
$674,900 |
Airbnb cash on cash: 1.48%
|
742 HARMS DRIVEOSPREY, FLBeautifully renovated and now offered at a newly reduced price, this turnkey property is a... |
3 beds | 2 baths | 1,293 sq.ft. |
$515,000 |
Airbnb cash on cash: 3.19%
|
14041 BELLAGIO WAY #218OSPREY, FLMOTIVATED SELLER. Bring an offer! Elevate your expectations with this elegant waterfront h... |
3 beds | 2 baths | 2,374 sq.ft. |
$999,000 |
Airbnb cash on cash: -0.88%
|
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: 3.96%
|
1801 HIGHLAND ROADOSPREY, FLOne or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhom... |
2 beds | 2 baths | 1,165 sq.ft. |
$299,900 |
Airbnb cash on cash: 5.22%
|
1019 SCHERER WAYOSPREY, FLWelcome to this beautiful 4 bedroom 3 full bath home situated in the desirable community o... |
4 beds | 3 baths | 2,498 sq.ft. |
$735,000 |
Airbnb cash on cash: 6.64%
|
764 SARABAY ROAD #8OSPREY, FLOne or more photo(s) has been virtually staged. Live the Florida dream on the water! Wake ... |
2 beds | 2 baths | 1,392 sq.ft. |
$450,000 |
Airbnb cash on cash: -0.87%
|
5100 JESSIE HARBOR DRIVE #403OSPREY, FLThis meticulously maintained, waterfront residence is in an amenity-rich, gated community.... |
2 beds | 2 baths | 2,143 sq.ft. |
$679,900 |
Airbnb cash on cash: -0.21%
|
104 PARK TRACE BOULEVARDOSPREY, FLWelcome to this elegant and spacious luxury pool home offering over 2,500 square feet of r... |
4 beds | 3 baths | 2,557 sq.ft. |
$595,000 |
Airbnb cash on cash: 8.32%
|
393 N POINT ROAD #401OSPREY, FLThis beautifully updated 3 bedroom, 3 bath residence with a den offers exceptional space, ... |
3 beds | 3 baths | 2,594 sq.ft. |
$785,000 |
Airbnb cash on cash: 1.14%
|
1795 HIGHLAND ROADOSPREY, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. Pe... |
3 beds | 3 baths | 1,879 sq.ft. |
$385,000 |
Airbnb cash on cash: 4.84%
|
385 N POINT ROAD #304OSPREY, FL**MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF R... |
3 beds | 3 baths | 2,778 sq.ft. |
$1,200,000 |
Airbnb cash on cash: 0.39%
|
76 OSPREY POINT DRIVEOSPREY, FLOWNER SAYS SELL! No Reasonable offer refused on this home that is already the lowest price... |
3 beds | 5 baths | 4,364 sq.ft. |
$1,590,000 |
Airbnb cash on cash: -0.48%
|
852 MACEWEN DRIVEOSPREY, FL**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the hig... |
3 beds | 4 baths | 4,519 sq.ft. |
$2,495,000 |
Airbnb cash on cash: -0.48%
|
75 OSPREY POINT DRIVEOSPREY, FL**STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on... |
4 beds | 4 baths | 4,001 sq.ft. |
$1,695,000 |
Airbnb cash on cash: 1.25%
|
409 N POINT ROAD #502OSPREY, FL**GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The cov... |
3 beds | 3 baths | 2,055 sq.ft. |
$599,000 |
Airbnb cash on cash: 2.02%
|
140 SUGAR MILL DRIVEOSPREY, FLBEST PRICED 4 BED IN THE OAKS - MAJOR UPDATES ALLOW IMMEDIATE MOVE IN - NO REMODELING NEED... |
4 beds | 4 baths | 3,286 sq.ft. |
$1,695,000 |
Airbnb cash on cash: 1.72%
|
110 PINE AVENUEOSPREY, FLHeart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your... |
3 beds | 2 baths | 2,058 sq.ft. |
$699,000 |
Airbnb cash on cash: 2.06%
|
17 BAYHEAD LANEOSPREY, FLImpeccable is the only way to describe this charming, completely remodeled 3-bedroom, 2-ba... |
3 beds | 2 baths | 2,850 sq.ft. |
$1,300,000 |
Airbnb cash on cash: 0.17%
|
401 N POINT ROAD #504OSPREY, FLFULLY UPDATED ⢠WATER VIEWS ⢠PRIVATE 2-CAR GARAGE ⢠OFFICE/4TH BEDROOM OPTION F... |
3 beds | 3 baths | 2,778 sq.ft. |
$990,000 |
Airbnb cash on cash: 0.43%
|
642 TRENTON WAYOSPREY, FLBeautifully updated and carefully maintained, this Rutenberg-designed home is idyllically ... |
4 beds | 5 baths | 3,939 sq.ft. |
$2,150,000 |
Airbnb cash on cash: 1.15%
|
401 N POINT ROAD #304OSPREY, FLGive yourself the gift of refined living in this expansive 2,778 square foot residenceât... |
3 beds | 3 baths | 2,778 sq.ft. |
$750,000 |
Airbnb cash on cash: 0.93%
|
409 N POINT ROAD #1001OSPREY, FLUnder contract-accepting backup offers. **STUNNINGLY RENOVATED, MOVE-IN READY 10th FLOOR P... |
3 beds | 3 baths | 3,029 sq.ft. |
$2,750,000 |
Airbnb cash on cash: -0.76%
|
14041 BELLAGIO WAY #415OSPREY, FLA boater's dream. Enjoy waterfront living in this luxury penthouse unit with breathtaking ... |
3 beds | 2 baths | 1,736 sq.ft. |
$699,000 |
Airbnb cash on cash: -0.15%
|
1211 LOST CREEK COURTOSPREY, FLUnder contract-accepting backup offers. **BEAUTIFULLY UPDATED AND MOVE-IN READY, THIS SPAC... |
4 beds | 3 baths | 2,876 sq.ft. |
$829,000 |
Airbnb cash on cash: 6.4%
|
597 OAK RIVER COURTOSPREY, FLUnder contract-accepting backup offers. Stunning, fully remodeled 4-bedroom, 2-bathroom ho... |
4 beds | 2 baths | 2,111 sq.ft. |
$699,000 |
Airbnb cash on cash: 7.3%
|
365 S SHORE DRIVEOSPREY, FLWake up to ever-changing INTRACOASTAL VIEWS â SUNSETS dancing across the water, BOATS gl... |
3 beds | 2 baths | 1,824 sq.ft. |
$1,380,000 |
Airbnb cash on cash: 0.41%
|
180 LOOKOUT POINT DRIVEOSPREY, FLOne or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the ... |
5 beds | 4 baths | 3,236 sq.ft. |
$2,249,900 |
Airbnb cash on cash: N/A
|
4428 CONCHFISH LANEOSPREY, FLChic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located ... |
4 beds | 2 baths | 1,861 sq.ft. |
$548,000 |
Airbnb cash on cash: 9.19%
|
401 N POINT ROAD #301OSPREY, FLOne or more photo(s) has been virtually staged. Enter through the secure foyer and take th... |
3 beds | 3 baths | 2,594 sq.ft. |
$475,000 |
Airbnb cash on cash: 2.38%
|
409 N POINT ROAD #601OSPREY, FL**FANTASTIC GULF AND BAY VIEWS FROM THIS UPDATED 6TH-FLOOR CORNER RESIDENCE** This spaciou... |
3 beds | 3 baths | 2,594 sq.ft. |
$1,250,000 |
Airbnb cash on cash: -0.01%
|
385 N POINT ROAD #503OSPREY, FLTURN-KEY FURNISHED 5TH FLOOR RESIDENCE WITH LOVELY VIEWS! Experience luxury coastal living... |
3 beds | 3 baths | 2,203 sq.ft. |
$690,000 |
Airbnb cash on cash: 1.26%
|
759 FORDINGBRIDGE WAYOSPREY, FLDiscover this stunning home located in the heart of Osprey, FL. Featuring a spacious layou... |
4 beds | 4 baths | 2,950 sq.ft. |
$727,000 |
Airbnb cash on cash: 6.69%
|
433 E MACEWEN DRIVEOSPREY, FLAn exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths... |
4 beds | 4 baths | 4,012 sq.ft. |
$2,250,000 |
Airbnb cash on cash: 1%
|
401 N POINT RD APT 301OSPREY, FLInvest with success and buy through Auction.com. This bank-owned investment property is a ... |
3 beds | 3 baths | 2,594 sq.ft. |
$751,000 |
Airbnb cash on cash: -0.16%
|
3621 N POINT ROAD #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. |
$625,000 |
Airbnb cash on cash: -1.14%
|
401 N POINT ROAD #603OSPREY, FLOne or more photo(s) has been virtually staged. This incredible offering has everything yo... |
3 beds | 3 baths | 2,203 sq.ft. |
$699,000 |
Airbnb cash on cash: -1.12%
|
293 TURQUOISE LANEOSPREY, FL**STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure ... |
3 beds | 2 baths | 2,271 sq.ft. |
$910,000 |
Airbnb cash on cash: 0.65%
|
Real Estate investment in Osprey, FL
There are 119 properties for sale in the city of Osprey . The median list price in Osprey is $780,000 and the average price per square foot is $299. In April 2026, the average monthly cash on cash return in Osprey is 3.00%. The average monthly rental income in Osprey is $4,257.