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%
|
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%
|
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. |
$340,000 |
Airbnb cash on cash: 4.56%
|
106 VILLA DRIVE #106OSPREY, FLLocated West of the Trail in Sorrento Shores, Osprey, this spacious 2BR/2BA villa with a d... |
2 beds | 2 baths | 1,578 sq.ft. |
$249,900 |
Airbnb cash on cash: 4.84%
|
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%
|
432 SORRENTO DRIVEOSPREY, FLUnder contract-accepting backup offers. Experience the ultimate boating lifestyle from thi... |
3 beds | 4 baths | 3,640 sq.ft. |
$2,550,000 |
Airbnb cash on cash: -0.36%
|
780 SARABAY ROAD #16OSPREY, FLBOATER'S PARADISE!! SELLER WILL CREDIT BUYER $20,000 AT CLOSING. Fish off the Pier or si... |
2 beds | 2 baths | 1,574 sq.ft. |
$449,900 |
Airbnb cash on cash: -1.7%
|
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%
|
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. |
$1,750,000 |
Airbnb cash on cash: -0.53%
|
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. |
$2,550,000 |
Airbnb cash on cash: -0.49%
|
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. |
$1,975,000 |
Airbnb cash on cash: 0.94%
|
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. |
$685,000 |
Airbnb cash on cash: 1.73%
|
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. |
$705,000 |
Airbnb cash on cash: 2.03%
|
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%
|
401 N POINT ROAD #901OSPREY, FLThis opulent 3 bedroom plus den, 3 bath residence with a PRIVATE 2 CAR GARAGE located in M... |
3 beds | 3 baths | 2,594 sq.ft. |
$1,549,000 |
Airbnb cash on cash: -0.19%
|
140 N CASEY KEY ROADOSPREY, FLStep into a world where the horizon meets the sea and every sunset paints a masterpiece. T... |
3 beds | 4 baths | 2,473 sq.ft. |
$2,350,000 |
Airbnb cash on cash: -0.86%
|
17 BAYHEAD LANEOSPREY, FLWelcome to an exquisitely revitalized estate set amidst a stunning landscape that is sure ... |
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 ~ The eye o... |
3 beds | 3 baths | 2,778 sq.ft. |
$1,150,000 |
Airbnb cash on cash: 0.26%
|
510 LATITUDE LANEOSPREY, FLStunning residence crafted by renowned builder Lee Wetherington. Nestled on a southern exp... |
3 beds | 2 baths | 2,298 sq.ft. |
$635,000 |
Airbnb cash on cash: 1.47%
|
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. |
$900,000 |
Airbnb cash on cash: 0.61%
|
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, FLLovely turn-key furnished, 3BR/2BA and a pool half BA, 3 car garage home bordering Oscar S... |
3 beds | 3 baths | 2,534 sq.ft. |
$765,000 |
Airbnb cash on cash: 1.04%
|
180 LOOKOUT POINT DRIVEOSPREY, FLOne or more photo(s) has been virtually staged. One or more photo(s) has been virtually st... |
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, 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. |
$500,000 |
Airbnb cash on cash: 2.21%
|
38 W BAY STREETOSPREY, FLLive like youâre on vacation in this updated Key Westâstyle home West of the Trail. Up... |
3 beds | 2 baths | 2,124 sq.ft. |
$899,000 |
Airbnb cash on cash: 1.29%
|
291 HIDDEN BAY DRIVE #101OSPREY, FLRARELY AVAILABLE FIRST FLOOR END-UNIT in the 12-acre waterfront resort-style gated communi... |
2 beds | 2 baths | 1,599 sq.ft. |
$400,000 |
Airbnb cash on cash: 0.91%
|
232 HIDDEN BAY DRIVE #504OSPREY, FLThis condominium has it all! Fantastic water views along the Intracoastal. Amazing sunsets... |
3 beds | 3 baths | 2,000 sq.ft. |
$599,000 |
Airbnb cash on cash: 2.32%
|
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%
|
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%
|
385 N POINT ROAD #404OSPREY, FL**STUNNINGLY UPDATED CONDO with Breathtaking Water & Preserve Views that rival those of hi... |
3 beds | 3 baths | 2,778 sq.ft. |
$889,000 |
Airbnb cash on cash: 0.82%
|
325 OSPREY POINT DRIVEOSPREY, FLUnder contract-accepting backup offers. **BEAUTIFULLY UPDATED COUNTRY CLUB ESTATE with Ide... |
3 beds | 5 baths | 3,905 sq.ft. |
$1,690,000 |
Airbnb cash on cash: -0.05%
|
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: 1.02%
|
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: 0.69%
|
3603 N POINT ROAD #202OSPREY, FL**ELEGANT and SPACIOUS CORNER CONDO UNIT â NEARLY 3200sf â With MULTIPLE BALCONIES** f... |
3 beds | 3 baths | 3,147 sq.ft. |
$749,000 |
Airbnb cash on cash: 1.55%
|
3621 N POINT ROAD #603OSPREY, FLPrepare to be captivated by this COMPLETELY UPDATED, meticulously maintained, and thoughtf... |
3 beds | 3 baths | 2,680 sq.ft. |
$1,350,000 |
Airbnb cash on cash: -0.11%
|
Real Estate investment in Osprey, FL
There are 113 properties for sale in the city of Osprey . The median list price in Osprey is $889,000 and the average price per square foot is $335. In December 2025, the average monthly cash on cash return in Osprey is 2.00%. The average monthly rental income in Osprey is $3,567.