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. |
$3,950,000 |
Airbnb cash on cash: -0.08%
|
730 SARABAY ROADOSPREY, FLPremier Intracoastal Estate in Osprey 4 Bedrooms | 6 Bathrooms | 6,308 Sq. Ft. | 2 Waterf... |
4 beds | 6 baths | 6,308 sq.ft. |
$5,495,000 |
Airbnb cash on cash: -0.69%
|
1303 THORNAPPLE DRIVEOSPREY, FLINCREDIBLE Pool Home in INCREDIBLE Community!...You Will Be Impressed by this Well-Appoint... |
3 beds | 2 baths | 1,929 sq.ft. |
$699,000 |
Airbnb cash on cash: 1.4%
|
14041 BELLAGIO WAY #218OSPREY, FLExperience exceptional waterfront living at Osprey Harbor Village. This 3-bedroom, 2-bath ... |
3 beds | 2 baths | 2,374 sq.ft. |
$1,150,000 |
Airbnb cash on cash: -0.9%
|
1363 NEW FOREST LANEOSPREY, FLWelcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the... |
2 beds | 2 baths | 1,738 sq.ft. |
$499,000 |
Airbnb cash on cash: 2.19%
|
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. |
$1,197,000 |
Airbnb cash on cash: 3.54%
|
494 MEADOW SWEET CIRCLEOSPREY, FLModern farmhouse style in the Rivendell Cottages which was the original builder's model. H... |
3 beds | 2 baths | 1,791 sq.ft. |
$595,000 |
Airbnb cash on cash: 2.41%
|
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. |
$330,000 |
Airbnb cash on cash: 4.72%
|
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%
|
106 VILLA DRIVE #106OSPREY, FLUnder contract-accepting backup offers. Located West of the Trail in Sorrento Shores, Ospr... |
2 beds | 2 baths | 1,578 sq.ft. |
$199,000 |
Airbnb cash on cash: 6.3%
|
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. |
$650,000 |
Airbnb cash on cash: 7.54%
|
409 N POINT ROAD #1003OSPREY, FLBeautifully updated and meticulously maintained 3 bedroom, 3 bath penthouse in Meridian at... |
3 beds | 3 baths | 2,778 sq.ft. |
$1,800,000 |
Airbnb cash on cash: -0.57%
|
901 REFLECTION WAYOSPREY, FLLOCATION! LOCATION! Tucked away on a quiet cul-de-sac and resting on a corner lot, this ME... |
3 beds | 2 baths | 2,443 sq.ft. |
$795,000 |
Airbnb cash on cash: 1.69%
|
146 WILLOW BEND WAYOSPREY, FLOne or more photo(s) has been virtually staged. Welcome to 146 Willow Bend Way, a custom-b... |
4 beds | 3 baths | 2,540 sq.ft. |
$699,000 |
Airbnb cash on cash: 7.29%
|
392 PARK TRACE BOULEVARDOSPREY, FLUnder contract-accepting backup offers. Set on a premier lakefront lot in Osprey, 392 Park... |
4 beds | 3 baths | 2,802 sq.ft. |
$939,000 |
Airbnb cash on cash: 4.81%
|
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, FLCOMPLETELY UPGRADED IS NOT AN EXAGGERATION! This Bo MacEwenâdesigned 3-bedroom, 4.5-bath... |
3 beds | 5 baths | 4,364 sq.ft. |
$1,690,000 |
Airbnb cash on cash: -0.51%
|
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. |
$1,775,000 |
Airbnb cash on cash: 1.16%
|
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. |
$635,000 |
Airbnb cash on cash: 1.95%
|
140 SUGAR MILL DRIVEOSPREY, FL**BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE RESIDENCE with Lush Garden Lan... |
4 beds | 4 baths | 3,286 sq.ft. |
$1,970,000 |
Airbnb cash on cash: 1.4%
|
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%
|
85 SUGAR MILL DRIVEOSPREY, FL**STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Coun... |
3 beds | 3 baths | 4,191 sq.ft. |
$2,150,000 |
Airbnb cash on cash: -0.79%
|
140 N CASEY KEY ROADOSPREY, FLLIVE THE ULTIMATE COASTAL LIFESTYLE on the coveted Casey Key barrier island at this vibran... |
3 beds | 4 baths | 2,473 sq.ft. |
$2,250,000 |
Airbnb cash on cash: -0.85%
|
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: 0.2%
|
401 N POINT ROAD #504OSPREY, FLFULLY UPDATED ⢠WATER VIEWS ⢠PRIVATE 2-CAR GARAGE ⢠OFFICE/4TH BEDROOM OPTION ⢠S... |
3 beds | 3 baths | 2,778 sq.ft. |
$1,100,000 |
Airbnb cash on cash: 0.32%
|
510 LATITUDE LANEOSPREY, FLStunning residence crafted by renowned builder Lee Wetherington. Nestled on a southern exp... |
3 beds | 2 baths | 2,298 sq.ft. |
$630,000 |
Airbnb cash on cash: 1.49%
|
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. |
$850,000 |
Airbnb cash on cash: 0.7%
|
2043 CORDES STREETOSPREY, FLCharming & Versatile Home Near the Beaches! This cute and cozy, well-maintained 3-bedroom... |
3 beds | 2 baths | 1,186 sq.ft. |
$299,000 |
Airbnb cash on cash: 7.12%
|
597 OAK RIVER COURTOSPREY, FLStunning, fully remodeled 4-bedroom, 2-bathroom home tucked away in a quiet cul-de-sac in ... |
4 beds | 2 baths | 2,111 sq.ft. |
$749,000 |
Airbnb cash on cash: 6.75%
|
691 EAGLE WATCH LANEOSPREY, FLNestled within the exclusive gated community of the Oaks Club in Osprey, Florida. This sin... |
4 beds | 7 baths | 6,705 sq.ft. |
$3,995,000 |
Airbnb cash on cash: -0.1%
|
640 CRANE PRAIRIE WAYOSPREY, FLUnder contract-accepting backup offers. Lovely turn-key furnished, 3BR/2BA and a pool half... |
3 beds | 3 baths | 2,534 sq.ft. |
$765,000 |
Airbnb cash on cash: 1.04%
|
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. |
$1,400,000 |
Airbnb cash on cash: 0.39%
|
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. |
$2,299,900 |
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. |
$599,000 |
Airbnb cash on cash: 8.33%
|
401 N POINT ROAD #301OSPREY, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. En... |
3 beds | 3 baths | 2,594 sq.ft. |
$395,000 |
Airbnb cash on cash: 3.06%
|
38 W BAY STREETOSPREY, FLUnder contract-accepting backup offers. Live like youâre on vacation in this updated Key... |
3 beds | 2 baths | 2,124 sq.ft. |
$899,000 |
Airbnb cash on cash: 1.29%
|
291 HIDDEN BAY DRIVE #101OSPREY, FLUnder contract-accepting backup offers. RARELY AVAILABLE FIRST FLOOR END-UNIT in the 12-ac... |
2 beds | 2 baths | 1,599 sq.ft. |
$400,000 |
Airbnb cash on cash: 0.91%
|
409 NORTH POINT ROAD #902OSPREY, FL**A RARE OFFERING, 9TH FLOOR, UPDATED PENTHOUSE with PRIVATE 2-CAR GARAGE** Enjoy the ulti... |
3 beds | 3 baths | 2,055 sq.ft. |
$1,275,000 |
Airbnb cash on cash: 0.05%
|
Real Estate investment in Osprey, FL
There are 117 properties for sale in the city of Osprey . The median list price in Osprey is $875,000 and the average price per square foot is $329. In January 2026, the average monthly cash on cash return in Osprey is 2.00%. The average monthly rental income in Osprey is $3,567.