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 63 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
854 MACEWEN DRIVE OSPREY, FL One 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: -0.01% Traditional cash on cash: 1.18% Airbnb Rental Income: $7455 Traditional Rental Income: $10120 Airbnb ROI: -0.01% Traditional ROI: 1.18%
730 SARABAY ROAD OSPREY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. PR...	4 beds \| 6 baths \| 6,308 sq.ft.	$4,995,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 0.82% Airbnb Rental Income: $7455 Traditional Rental Income: $12867 Airbnb ROI: -0.66% Traditional ROI: 0.82%
742 HARMS DRIVE OSPREY, FL Beautifully renovated and now offered at a newly reduced price, this turnkey property is a...	3 beds \| 2 baths \| 1,293 sq.ft.	$515,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 4.8% Airbnb Rental Income: $3385 Traditional Rental Income: $3405 Airbnb ROI: 3.19% Traditional ROI: 4.8%
135 TINA ISLAND DRIVE OSPREY, 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: -0.55% Traditional cash on cash: 0.38% Airbnb Rental Income: $3385 Traditional Rental Income: $5485 Airbnb ROI: -0.55% Traditional ROI: 0.38%
403 LONGBOW TRAIL OSPREY, FL Welcome 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: 3.96% Traditional cash on cash: 2.88% Airbnb Rental Income: $7455 Traditional Rental Income: $4922 Airbnb ROI: 3.96% Traditional ROI: 2.88%
103 BISHOPS COURT ROAD OSPREY, 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: 1.46% Traditional cash on cash: 2% Airbnb Rental Income: $3385 Traditional Rental Income: $3003 Airbnb ROI: 1.46% Traditional ROI: 2%
764 SARABAY ROAD #8 OSPREY, FL One 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: -0.87% Traditional cash on cash: 1.38% Airbnb Rental Income: $2934 Traditional Rental Income: $3203 Airbnb ROI: -0.87% Traditional ROI: 1.38%
1361 New Forest Lane OSPREY, FL Exceptional opportunity in highly sought-after Rivendell, one of Ospreyâs most desirable...	3 beds \| 2 baths \| 2,074 sq.ft.	$550,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 3.8% Airbnb Rental Income: $3385 Traditional Rental Income: $2842 Airbnb ROI: 3.39% Traditional ROI: 3.8%
104 PARK TRACE BOULEVARD OSPREY, FL Welcome to this elegant and spacious luxury pool home offering over 2,500 square feet of r...	4 beds \| 3 baths \| 2,557 sq.ft.	$550,000	Airbnb cash on cash: 9.08% Traditional cash on cash: 5.63% Airbnb Rental Income: $7455 Traditional Rental Income: $4254 Airbnb ROI: 9.08% Traditional ROI: 5.63%
408 YACHT HARBOR DRIVE OSPREY, FL Under contract-accepting backup offers. Renovated throughout, this stunning four-bedroom, ...	4 beds \| 4 baths \| 2,624 sq.ft.	$1,375,000	Airbnb cash on cash: 2.77% Traditional cash on cash: 2.01% Airbnb Rental Income: $7455 Traditional Rental Income: $5051 Airbnb ROI: 2.77% Traditional ROI: 2.01%
1795 HIGHLAND ROAD OSPREY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Pe...	3 beds \| 3 baths \| 1,879 sq.ft.	$385,000	Airbnb cash on cash: 4.84% Traditional cash on cash: 5.53% Airbnb Rental Income: $3385 Traditional Rental Income: $2878 Airbnb ROI: 4.84% Traditional ROI: 5.53%
76 OSPREY POINT DRIVE OSPREY, FL Under contract-accepting backup offers. OWNER SAYS SELL! No Reasonable offer refused on th...	3 beds \| 5 baths \| 4,364 sq.ft.	$1,545,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 2.94% Airbnb Rental Income: $3385 Traditional Rental Income: $7516 Airbnb ROI: -0.47% Traditional ROI: 2.94%
852 MACEWEN DRIVE OSPREY, 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: -0.46% Traditional cash on cash: 1.23% Airbnb Rental Income: $3385 Traditional Rental Income: $6382 Airbnb ROI: -0.46% Traditional ROI: 1.23%
140 SUGAR MILL DRIVE OSPREY, FL Under contract-accepting backup offers. SELLERS SAY SELL! BEST PRICED 4 BED IN THE OAKS - ...	4 beds \| 4 baths \| 3,286 sq.ft.	$1,399,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 2.93% Airbnb Rental Income: $7455 Traditional Rental Income: $6849 Airbnb ROI: 2.29% Traditional ROI: 2.93%
110 PINE AVENUE OSPREY, FL Heart 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% Traditional cash on cash: 4.44% Airbnb Rental Income: $3385 Traditional Rental Income: $4189 Airbnb ROI: 2.06% Traditional ROI: 4.44%
17 BAYHEAD LANE OSPREY, FL Impeccable 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: 0.18% Traditional cash on cash: 1.13% Airbnb Rental Income: $3385 Traditional Rental Income: $3778 Airbnb ROI: 0.18% Traditional ROI: 1.13%
642 TRENTON WAY OSPREY, FL Beautifully updated and carefully maintained, this Rutenberg-designed home is idyllically ...	4 beds \| 5 baths \| 3,939 sq.ft.	$2,150,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 2.14% Airbnb Rental Income: $7455 Traditional Rental Income: $7993 Airbnb ROI: 1.15% Traditional ROI: 2.14%
292 TURQUOISE LANE OSPREY, FL This 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: 0.53% Traditional cash on cash: 1.75% Airbnb Rental Income: $3385 Traditional Rental Income: $3830 Airbnb ROI: 0.53% Traditional ROI: 1.75%
1211 LOST CREEK COURT OSPREY, FL Under 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: 6.4% Traditional cash on cash: 5.47% Airbnb Rental Income: $7455 Traditional Rental Income: $5303 Airbnb ROI: 6.4% Traditional ROI: 5.47%
365 S SHORE DRIVE OSPREY, FL Wake 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: 0.45% Traditional cash on cash: 1.25% Airbnb Rental Income: $3385 Traditional Rental Income: $3647 Airbnb ROI: 0.45% Traditional ROI: 1.25%
180 LOOKOUT POINT DRIVE OSPREY, FL One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the ...	5 beds \| 4 baths \| 3,236 sq.ft.	$2,249,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.38% Airbnb Rental Income: $null Traditional Rental Income: $6082 Airbnb ROI: N/A Traditional ROI: 1.38%
4428 CONCHFISH LANE OSPREY, FL Chic 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: 9.19% Traditional cash on cash: 3.03% Airbnb Rental Income: $7455 Traditional Rental Income: $2870 Airbnb ROI: 9.19% Traditional ROI: 3.03%
759 FORDINGBRIDGE WAY OSPREY, FL Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layou...	4 beds \| 4 baths \| 2,950 sq.ft.	$770,000	Airbnb cash on cash: 6.26% Traditional cash on cash: 5.42% Airbnb Rental Income: $7455 Traditional Rental Income: $5418 Airbnb ROI: 6.26% Traditional ROI: 5.42%
433 E MACEWEN DRIVE OSPREY, FL An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths...	4 beds \| 4 baths \| 4,012 sq.ft.	$2,250,000	Airbnb cash on cash: 1% Traditional cash on cash: 1.3% Airbnb Rental Income: $7455 Traditional Rental Income: $6658 Airbnb ROI: 1% Traditional ROI: 1.3%
293 TURQUOISE LANE OSPREY, 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: 0.72% Traditional cash on cash: 1.72% Airbnb Rental Income: $3385 Traditional Rental Income: $3448 Airbnb ROI: 0.72% Traditional ROI: 1.72%
401 WALLS WAY OSPREY, FL Perfectly positioned on the 9th hole tee box within the Oaks community, this meticulously ...	4 beds \| 4 baths \| 4,387 sq.ft.	$1,775,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 1.19% Airbnb Rental Income: $7455 Traditional Rental Income: $5053 Airbnb ROI: 1.78% Traditional ROI: 1.19%
360 N POINT ROAD OSPREY, FL DONâT WAIT TO BUILD! EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSI...	3 beds \| 4 baths \| 2,913 sq.ft.	$1,499,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 2.12% Airbnb Rental Income: $3385 Traditional Rental Income: $5911 Airbnb ROI: -0.23% Traditional ROI: 2.12%
32 BAY AVENUE OSPREY, FL Under contract-accepting backup offers. Located in the highly sought-after Bay Acres commu...	2 beds \| 2 baths \| 2,148 sq.ft.	$415,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 5.88% Airbnb Rental Income: $2934 Traditional Rental Income: $3120 Airbnb ROI: 3.66% Traditional ROI: 5.88%
909 MACEWEN DRIVE OSPREY, FL STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community sit...	3 beds \| 4 baths \| 4,241 sq.ft.	$1,595,000	Airbnb cash on cash: 0% Traditional cash on cash: 2.93% Airbnb Rental Income: $3385 Traditional Rental Income: $6975 Airbnb ROI: 0% Traditional ROI: 2.93%
2251 JESSIE HARBOR DRIVE #2101 OSPREY, 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.	$349,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 3.25% Airbnb Rental Income: $2934 Traditional Rental Income: $2681 Airbnb ROI: 1.96% Traditional ROI: 3.25%
662 FERNWALK LANE OSPREY, FL **EXCEPTIONAL, FULLY RENOVATED, COUNTRY CLUB ESTATE HOME OFFERING TRANQUIL LAKE AND GARDEN...	4 beds \| 4 baths \| 4,359 sq.ft.	$2,850,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 1.11% Airbnb Rental Income: $7455 Traditional Rental Income: $7097 Airbnb ROI: 0.71% Traditional ROI: 1.11%
18 N CASEY KEY ROAD OSPREY, FL Under contract-accepting backup offers. Elegantly renovated bayfront retreat on Casey Key ...	3 beds \| 2 baths \| 1,977 sq.ft.	$1,750,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 0.41% Airbnb Rental Income: $3385 Traditional Rental Income: $4644 Airbnb ROI: -0.83% Traditional ROI: 0.41%
1216 N CASEY KEY ROAD OSPREY, FL This classically designed estate is privately positioned on north end of Casey Key, consid...	5 beds \| 8 baths \| 8,050 sq.ft.	$10,750,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.24% Airbnb Rental Income: $null Traditional Rental Income: $15288 Airbnb ROI: N/A Traditional ROI: -0.24%
600 EAGLE WATCH LANE OSPREY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **...	3 beds \| 3 baths \| 3,681 sq.ft.	$2,195,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 0.35% Airbnb Rental Income: $3385 Traditional Rental Income: $4353 Airbnb ROI: -0.5% Traditional ROI: 0.35%
13 BAYHEAD LANE OSPREY, 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: 1.33% Traditional cash on cash: 2.95% Airbnb Rental Income: $3385 Traditional Rental Income: $3842 Airbnb ROI: 1.33% Traditional ROI: 2.95%
352 GLENWOOD AVE OSPREY, FL Beautifully 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: 4.46% Traditional cash on cash: 4.29% Airbnb Rental Income: $3385 Traditional Rental Income: $2566 Airbnb ROI: 4.46% Traditional ROI: 4.29%
296 PINE RANCH TRAIL OSPREY, FL **THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER....	5 beds \| 4 baths \| 3,481 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.25% Airbnb Rental Income: $null Traditional Rental Income: $6213 Airbnb ROI: N/A Traditional ROI: 4.25%
1527 BUOY LANE OSPREY, FL Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet...	3 beds \| 3 baths \| 2,830 sq.ft.	$1,199,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 1.82% Airbnb Rental Income: $3385 Traditional Rental Income: $4259 Airbnb ROI: 0.37% Traditional ROI: 1.82%
21 BAYHEAD LANE OSPREY, FL Looking for a home you can truly fall in love with? Your search ends here. This thoughtful...	3 beds \| 2 baths \| 2,246 sq.ft.	$850,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 3.11% Airbnb Rental Income: $3385 Traditional Rental Income: $4244 Airbnb ROI: 1.07% Traditional ROI: 3.11%
422 BLUE GARDEN LANE OSPREY, FL A grand traditional residence, this 3-bedroom, 3.5-bath home is tucked into lush tropical ...	3 beds \| 4 baths \| 3,872 sq.ft.	$1,495,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 2.99% Airbnb Rental Income: $3385 Traditional Rental Income: $6841 Airbnb ROI: -0.04% Traditional ROI: 2.99%

Your search for investment property begins and ends here

Single Family Homes for Sale in Osprey, FL

854 MACEWEN DRIVE

OSPREY, FL

4 beds | 6 baths | 9,081 sq.ft.

$3,690,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $7455

Traditional Rental Income: $10120

Airbnb ROI: -0.01%

Traditional ROI: 1.18%

730 SARABAY ROAD

OSPREY, FL

4 beds | 6 baths | 6,308 sq.ft.

$4,995,000

Airbnb cash on cash: -0.66%

Traditional cash on cash: 0.82%

Airbnb Rental Income: $7455

Traditional Rental Income: $12867

Airbnb ROI: -0.66%

Traditional ROI: 0.82%

742 HARMS DRIVE

OSPREY, FL

3 beds | 2 baths | 1,293 sq.ft.

$515,000

Airbnb cash on cash: 3.19%

Traditional cash on cash: 4.8%

Airbnb Rental Income: $3385

Traditional Rental Income: $3405

Airbnb ROI: 3.19%

Traditional ROI: 4.8%

135 TINA ISLAND DRIVE

OSPREY, FL

3 beds | 5 baths | 2,572 sq.ft.

$3,295,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 0.38%

Airbnb Rental Income: $3385

Traditional Rental Income: $5485

Airbnb ROI: -0.55%

Traditional ROI: 0.38%

403 LONGBOW TRAIL

OSPREY, FL

4 beds | 3 baths | 2,770 sq.ft.

$1,095,000

Airbnb cash on cash: 3.96%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $7455

Traditional Rental Income: $4922

Airbnb ROI: 3.96%

Traditional ROI: 2.88%

103 BISHOPS COURT ROAD

OSPREY, FL

3 beds | 2 baths | 2,034 sq.ft.

$749,000

Airbnb cash on cash: 1.46%

Traditional cash on cash: 2%

Airbnb Rental Income: $3385

Traditional Rental Income: $3003

Airbnb ROI: 1.46%

Traditional ROI: 2%

764 SARABAY ROAD #8

OSPREY, FL

2 beds | 2 baths | 1,392 sq.ft.

$450,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: 1.38%

Airbnb Rental Income: $2934

Traditional Rental Income: $3203

Airbnb ROI: -0.87%

Traditional ROI: 1.38%

1361 New Forest Lane

OSPREY, FL

3 beds | 2 baths | 2,074 sq.ft.

$550,000

Airbnb cash on cash: 3.39%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $3385

Traditional Rental Income: $2842

Airbnb ROI: 3.39%