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. |
$3,690,000 |
Airbnb cash on cash: -0.98%
|
742 HARMS DRIVEOSPREY, FLBeautifully renovated and move-in ready, this exceptional property offers the perfect blen... |
3 beds | 2 baths | 1,293 sq.ft. |
$515,000 |
Airbnb cash on cash: 1.94%
|
14041 BELLAGIO WAY #218OSPREY, FLElevate your expectations with this elegant waterfront home! This 3-bedroom, 2-bath FULLY ... |
3 beds | 2 baths | 2,086 sq.ft. |
$999,000 |
Airbnb cash on cash: -1.53%
|
135 TINA ISLAND DRIVEOSPREY, FL**EXCEPTIONAL WATERFRONT RESIDENCE with 210 ft CANAL FRONTAGE** in desirable Sorrento Shor... |
3 beds | 5 baths | 2,572 sq.ft. |
$3,295,000 |
Airbnb cash on cash: -0.75%
|
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: 0.7%
|
103 BISHOPS COURT ROADOSPREY, 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: 0.6%
|
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. |
$289,900 |
Airbnb cash on cash: 1.2%
|
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: -3.61%
|
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. |
$1,175,000 |
Airbnb cash on cash: -1.37%
|
1361 New Forest LaneOSPREY, FLOne or more photo(s) has been virtually staged. Exceptional opportunity in highly sought-a... |
3 beds | 2 baths | 2,074 sq.ft. |
$545,000 |
Airbnb cash on cash: 2.25%
|
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. |
$650,000 |
Airbnb cash on cash: -2.08%
|
104 PARK TRACE BOULEVARDOSPREY, FLUnder contract-accepting backup offers. Welcome to this elegant and spacious luxury pool h... |
4 beds | 3 baths | 2,557 sq.ft. |
$550,000 |
Airbnb cash on cash: 2.62%
|
393 N POINT ROAD #401OSPREY, FLOffered Turn-Key Furnished...This beautifully updated 3 bedroom, 3 bath residence with a d... |
3 beds | 3 baths | 2,594 sq.ft. |
$785,000 |
Airbnb cash on cash: 0.31%
|
5100 JESSIE HARBOR DRIVE #304OSPREY, FLExperience effortless coastal living in this stunning third-floor FURNISHED waterfront res... |
2 beds | 2 baths | 2,143 sq.ft. |
$725,000 |
Airbnb cash on cash: -2.14%
|
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. |
$1,100,000 |
Airbnb cash on cash: -0.07%
|
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. |
$2,395,000 |
Airbnb cash on cash: -0.73%
|
754 PINE RUN DRIVE #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: -2%
|
75 OSPREY POINT DRIVEOSPREY, FLOffered at a price approaching the value of the two buildable lots alone, this architect-d... |
4 beds | 4 baths | 4,001 sq.ft. |
$1,649,000 |
Airbnb cash on cash: -0.86%
|
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: 0.95%
|
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. |
$649,000 |
Airbnb cash on cash: 1.3%
|
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. |
$1,295,000 |
Airbnb cash on cash: -0.32%
|
110 WOODLAND PLACE #110OSPREY, FLFURNISHED. Welcome to Pine Run, where you'll find the perfect combination of natural beaut... |
2 beds | 2 baths | 1,325 sq.ft. |
$215,000 |
Airbnb cash on cash: -0.44%
|
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. |
$700,000 |
Airbnb cash on cash: 0.14%
|
292 TURQUOISE LANEOSPREY, FLThis stunning, updated home sits on a corner lot; the largest in Emerald Woods. Located be... |
3 beds | 2 baths | 2,255 sq.ft. |
$1,050,000 |
Airbnb cash on cash: -0.09%
|
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: 2.11%
|
730 FORDINGBRIDGE WAYOSPREY, FLThereâs a quiet kind of beauty in a home that just feels right the moment you walk in, w... |
3 beds | 2 baths | 2,182 sq.ft. |
$710,000 |
Airbnb cash on cash: 0.82%
|
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: -0.03%
|
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: 0.77%
|
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: 2.71%
|
401 N POINT ROAD #301OSPREY, FLVirtually Staged. Short Sale. Enter through the secure foyer and take the private elevator... |
3 beds | 3 baths | 2,594 sq.ft. |
$475,000 |
Airbnb cash on cash: 1.03%
|
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: -0.53%
|
429 PATTERSON AVENUEOSPREY, FLIncredible opportunity with a $10,000 credit to buyers at closing for costs or a rate buy-... |
3 beds | 1 baths | 1,173 sq.ft. |
$449,000 |
Airbnb cash on cash: 2.67%
|
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: 0.32%
|
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. |
$749,000 |
Airbnb cash on cash: 1.71%
|
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. |
$2,189,000 |
Airbnb cash on cash: -0.58%
|
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: -1.02%
|
1367 THORNAPPLE DRIVEOSPREY, FLDiscover unparalleled luxury in this exquisite Lee Wetherington-built residence, ideally i... |
3 beds | 2 baths | 2,182 sq.ft. |
$579,000 |
Airbnb cash on cash: 0.78%
|
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: -2.17%
|
7204 JESSIE HARBOR DRIVE #7204OSPREY, FL**BEAUTIFULLY UPDATED CONDO, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO I... |
2 beds | 2 baths | 1,255 sq.ft. |
$395,000 |
Airbnb cash on cash: -1.48%
|
401 N POINT ROAD #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: -2.16%
|
Real Estate investment in Osprey, FL
There are 98 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 $238. In July 2026, the average monthly cash on cash return in Osprey is 3.00%. The average monthly rental income in Osprey is $3,982.