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 |
|---|---|---|---|
135 Tina Island DrOSPREY, FL**EXCEPTIONAL WATERFRONT RESIDENCE with 210 ft CANAL FRONTAGE** in desirable Sorrento Shor... |
3 beds | 4 baths | 2,572 sq.ft. |
$3,295,000 |
Airbnb cash on cash: 0.12%
|
403 Longbow TrlOSPREY, 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: 3.94%
|
103 Bishops Court RdOSPREY, FL**LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Coz... |
3 beds | 2 baths | 2,034 sq.ft. |
$749,000 |
Airbnb cash on cash: 4.42%
|
1801 Highland RdOSPREY, 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. |
$289,900 |
Airbnb cash on cash: 9.63%
|
764 Sarabay Rd #8OSPREY, FLVirtually Staged. Live the Florida dream on the water! Wake up to shimmering bay views, sp... |
2 beds | 2 baths | 1,392 sq.ft. |
$399,000 |
Airbnb cash on cash: 2.11%
|
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. |
$1,100,000 |
Airbnb cash on cash: 1.06%
|
1361 New Forest LnOSPREY, FLPRICE TO SELL. One or more photo(s) has been virtually staged. Exceptional opportunity in ... |
3 beds | 2 baths | 2,074 sq.ft. |
$535,000 |
Airbnb cash on cash: 7.63%
|
385 N Point Rd #304OSPREY, FL**MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF R... |
3 beds | 3 baths | 2,778 sq.ft. |
$1,100,000 |
Airbnb cash on cash: 2.53%
|
852 Macewen DrOSPREY, FL**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the hig... |
3 beds | 3 baths | 4,519 sq.ft. |
$2,395,000 |
Airbnb cash on cash: 0.47%
|
754 Pine Run Dr #754OSPREY, FLVirtually Staged. Rarely available and truly one-of-a-kind, this beautifully updated groun... |
2 beds | 2 baths | 1,379 sq.ft. |
$259,000 |
Airbnb cash on cash: 7.42%
|
409 N Point Rd #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: 5.71%
|
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: 5.69%
|
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: 6.37%
|
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. |
$1,349,000 |
Airbnb cash on cash: 2.09%
|
409 N Point Rd #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: 1.76%
|
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. |
$715,000 |
Airbnb cash on cash: 6.43%
|
433 E Macewen DrOSPREY, FLAn exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths... |
4 beds | 3 baths | 4,012 sq.ft. |
$2,189,000 |
Airbnb cash on cash: 1.04%
|
293 Turquoise LnOSPREY, FL**STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure ... |
3 beds | 2 baths | 2,271 sq.ft. |
$875,000 |
Airbnb cash on cash: 3.25%
|
3603 N Point Rd #202OSPREY, FL**ELEGANT and SPACIOUS CORNER CONDO UNIT â NEARLY 3200sf â With MULTIPLE BALCONIES** f... |
3 beds | 3 baths | 3,147 sq.ft. |
$699,000 |
Airbnb cash on cash: 4.79%
|
909 Macewen DrOSPREY, FL**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** sit... |
3 beds | 3 baths | 4,241 sq.ft. |
$1,595,000 |
Airbnb cash on cash: 1.39%
|
385 N Point Rd #402OSPREY, FL**BEAUTIFULLY UPDATED CONDO with MARVELOUS VIEW** features 3-BEDS and 3-FULL BATH, Open Fl... |
3 beds | 3 baths | 2,055 sq.ft. |
$615,000 |
Airbnb cash on cash: 4.86%
|
393 N POINT ROAD #604OSPREY, FLUnder contract-accepting backup offers. Immerse yourself in the unparalleled, unobstructed... |
3 beds | 3 baths | 2,778 sq.ft. |
$795,000 |
Airbnb cash on cash: 3.46%
|
3603 N Point Rd #702OSPREY, FL**MAGNIFICENT VIEW from this 7th FLOOR, PENTHOUSE CONDO** Offering 3 EN SUITE BEDROOMS, 3 ... |
3 beds | 3 baths | 2,545 sq.ft. |
$1,395,000 |
Airbnb cash on cash: 1.46%
|
13 Bayhead LnOSPREY, FL**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANC... |
3 beds | 2 baths | 2,310 sq.ft. |
$799,000 |
Airbnb cash on cash: 4.09%
|
352 Glenwood AveOSPREY, FLBeautifully Maintained 3-Bedroom Home with No HOA or Deed Restrictions Welcome to this ... |
3 beds | 2 baths | 1,300 sq.ft. |
$417,000 |
Airbnb cash on cash: 9.74%
|
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: 2.31%
|
1602 SOUTHBAY DRIVEOSPREY, FLWelcome to your slice of Florida paradise! Nestled on a spacious corner lot in the highly... |
4 beds | 4 baths | 2,980 sq.ft. |
$974,900 |
Airbnb cash on cash: 4.25%
|
538 Dove Pointe DrOSPREY, FL**ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welco... |
4 beds | 5 baths | 4,346 sq.ft. |
$1,950,000 |
Airbnb cash on cash: 1.31%
|
678 FAITH AVENUEOSPREY, FLPrivate Key Westâstyle retreat on 2.53 wooded acres in Osprey. Rarely does a property of... |
3 beds | 3 baths | 2,583 sq.ft. |
$749,000 |
Airbnb cash on cash: 4.81%
|
786 Sarabay Rd #19OSPREY, FLBoat Slips included, Insurance included, Ground maintenance included!!Secluded waterfront ... |
2 beds | 2 baths | 1,555 sq.ft. |
$489,000 |
Airbnb cash on cash: 1.6%
|
33 Bishops Court Rd #118OSPREY, FL**EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIE... |
2 beds | 2 baths | 1,890 sq.ft. |
$679,000 |
Airbnb cash on cash: 2.98%
|
25 SUGAR MILL DRIVEOSPREY, FLUnder contract-accepting backup offers. METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, ... |
3 beds | 4 baths | 3,066 sq.ft. |
$1,489,000 |
Airbnb cash on cash: 1.41%
|
401 N Point Rd #1001OSPREY, FL**Rarely available 10th-floor penthouse corner residence offering 3,029 square feet with s... |
3 beds | 3 baths | 3,029 sq.ft. |
$1,995,000 |
Airbnb cash on cash: 0.74%
|
9718 Crystal Isles CirOSPREY, FLUnder Construction. This is such a great floorplan, with the Primary Bedroom, full en-suit... |
4 beds | 3 baths | 2,628 sq.ft. |
$779,999 |
Airbnb cash on cash: 3.26%
|
260 Hidden Bay Dr #304OSPREY, FLThe Boca Residence: Spacious Living & Resort Style Discover a condominium that offers the... |
2 beds | 2 baths | 1,950 sq.ft. |
$694,000 |
Airbnb cash on cash: 0.55%
|
107 Sorrento DrOSPREY, 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: 6.68%
|
448 E MACEWEN DRIVEOSPREY, FL**IMPRESSIVE GOLF COURSE ESTATE IN THE HIGHLY SOUGHT-AFTER OAKS COUNTRY CLUB** Situated on... |
4 beds | 4 baths | 3,768 sq.ft. |
$2,100,000 |
Airbnb cash on cash: 1.5%
|
113 BURNEY ROADOSPREY, FLUnder contract-accepting backup offers. **DONâT WAIT TO BUILD!! NEWER, CUSTOM-BUILT HOM... |
3 beds | 3 baths | 2,502 sq.ft. |
$999,500 |
Airbnb cash on cash: 2.91%
|
184 Explorer DrOSPREY, FLLuxury Corner Residence in Osprey | Top-Rated Pine View School District. Welcome to an ex... |
2 beds | 2 baths | 1,244 sq.ft. |
$294,900 |
Airbnb cash on cash: 7.85%
|
272 FOUR KNOT LANEOSPREY, FLUnder contract-accepting backup offers. Welcome to this simply stunning, meticulously main... |
5 beds | 3 baths | 2,723 sq.ft. |
$1,095,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Osprey, FL
There are 121 properties for sale in the city of Osprey . The median list price in Osprey is $580,653 and the average price per square foot is $237. In August 2026, the average monthly cash on cash return in Osprey is 3.00%. The average monthly rental income in Osprey is $3,981.