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.
Single Family Homes for Sale in Osprey, FL
Search for Single Family Residential for Sale in Osprey, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.
Showing 74 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.
| 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%
|
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%
|
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%
|
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%
|
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%
|
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%
|
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%
|
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%
|
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%
|
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%
|
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%
|
340 OSPREY POINT DROSPREY, FLIntroducing The Grand Estate at The Oaks Baysideâa true masterpiece of refined living wi... |
5 beds | 7 baths | 6,001 sq.ft. |
$2,395,000 |
Airbnb cash on cash: N/A
|
360 N POINT ROADOSPREY, FL**DONâT WAIT TO BUILD!** EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSI... |
3 beds | 4 baths | 2,913 sq.ft. |
$1,570,000 |
Airbnb cash on cash: -0.23%
|
819 SHADOW BAY WAYOSPREY, FLA new 2025 roof. This stunning 2,145-square-foot pool home is in the premier community of ... |
4 beds | 2 baths | 2,145 sq.ft. |
$689,000 |
Airbnb cash on cash: 6.94%
|
508 MEADOW SWEET CIRCLEOSPREY, FLPRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an... |
2 beds | 2 baths | 1,604 sq.ft. |
$465,000 |
Airbnb cash on cash: 2.22%
|
32 Bay AvenueOSPREY, FLLocated in the highly sought-after Bay Acres community, this home offers modern upgrades, ... |
2 beds | 2 baths | 2,148 sq.ft. |
$463,000 |
Airbnb cash on cash: 3.25%
|
523 HABITAT BOULEVARDOSPREY, FLIn the Lee Wetherington-built community of Willowbend is a stunning home. This enchanting ... |
4 beds | 3 baths | 2,314 sq.ft. |
$785,500 |
Airbnb cash on cash: 5.98%
|
909 MACEWEN DRIVEOSPREY, FL**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** sit... |
3 beds | 4 baths | 4,241 sq.ft. |
$1,695,000 |
Airbnb cash on cash: -0.06%
|
312 YACHT HARBOR DRIVEOSPREY, FLOne or more photo(s) has been virtually staged. Considered one of the finest community-own... |
4 beds | 4 baths | 2,572 sq.ft. |
$2,299,000 |
Airbnb cash on cash: 1.07%
|
2251 JESSIE HARBOR DRIVE #2101OSPREY, FL**1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING ... |
2 beds | 2 baths | 1,400 sq.ft. |
$395,000 |
Airbnb cash on cash: 4.34%
|
219 KEEL WAYOSPREY, FL**IMPRESSIVE, METICULOUSLY MAINTAINED, SINGLE-STORY, CUL DE SAC ESTATE in the Highly Sough... |
3 beds | 3 baths | 2,735 sq.ft. |
$1,175,000 |
Airbnb cash on cash: 0.67%
|
227 SAINT JAMES PARKOSPREY, FL**TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect, Bo MacEwen, on the... |
2 beds | 2 baths | 2,071 sq.ft. |
$995,000 |
Airbnb cash on cash: 0.73%
|
370 SUGAR MILL DRIVEOSPREY, FL**Meticulously maintained, architectural perfection, this bright, spectacular estate featu... |
5 beds | 6 baths | 4,783 sq.ft. |
$2,650,000 |
Airbnb cash on cash: N/A
|
18 N CASEY KEY ROADOSPREY, FLElegantly renovated bayfront retreat on Casey Key and tastefully remodeled in 2012, this s... |
3 beds | 2 baths | 1,977 sq.ft. |
$2,350,000 |
Airbnb cash on cash: -0.87%
|
1216 N CASEY KEY ROADOSPREY, FLThis classically designed estate is privately positioned on north end of Casey Key, consid... |
5 beds | 8 baths | 8,050 sq.ft. |
$11,750,000 |
Airbnb cash on cash: N/A
|
1049 N CASEY KEY ROADOSPREY, FLUnder contract-accepting backup offers. Seize the opportunity to own a piece of paradise o... |
3 beds | 3 baths | 2,582 sq.ft. |
$4,750,000 |
Airbnb cash on cash: -0.75%
|
600 EAGLE WATCH LANEOSPREY, FLOne or more photo(s) has been virtually staged. **BRILLIANTLY UPDATED, MOVE-IN READY, GOLF... |
3 beds | 3 baths | 3,681 sq.ft. |
$2,195,000 |
Airbnb cash on cash: -0.5%
|