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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1363 NEW FOREST LANE OSPREY, FL Welcome 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% Traditional cash on cash: 2.91% Airbnb Rental Income: $2934 Traditional Rental Income: $2592 Airbnb ROI: 2.19% Traditional ROI: 2.91%
519 BAYVIEW AVENUE OSPREY, FL Value Property in a Great Coastal Location. Perfect for a Boating Community in Sarasota, B...	3 beds \| 2 baths \| 1,885 sq.ft.	$495,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 4% Airbnb Rental Income: $3385 Traditional Rental Income: $2623 Airbnb ROI: 4.02% Traditional ROI: 4%
563 PINE RANCH EAST ROAD OSPREY, FL Under contract-accepting backup offers. Step into your dream home in the sought-after Bay ...	3 beds \| 2 baths \| 2,346 sq.ft.	$675,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 3.64% Airbnb Rental Income: $3385 Traditional Rental Income: $3530 Airbnb ROI: 2.21% Traditional ROI: 3.64%
901 REFLECTION WAY OSPREY, FL LOCATION! 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% Traditional cash on cash: 2.2% Airbnb Rental Income: $3385 Traditional Rental Income: $3009 Airbnb ROI: 1.69% Traditional ROI: 2.2%
67 SUGAR MILL DRIVE OSPREY, FL Under contract-accepting backup offers. This is your rare chance to claim a spectacular es...	4 beds \| 5 baths \| 4,020 sq.ft.	$1,999,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 1.65% Airbnb Rental Income: $7455 Traditional Rental Income: $6415 Airbnb ROI: 1.44% Traditional ROI: 1.65%
392 PARK TRACE BOULEVARD OSPREY, FL Set on a premier lakefront lot in Osprey, 392 Park Trace offers serene water views, incred...	4 beds \| 3 baths \| 2,802 sq.ft.	$939,000	Airbnb cash on cash: 4.81% Traditional cash on cash: 3.1% Airbnb Rental Income: $7455 Traditional Rental Income: $4526 Airbnb ROI: 4.81% Traditional ROI: 3.1%
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.	$2,550,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 0.52% Airbnb Rental Income: $3385 Traditional Rental Income: $5023 Airbnb ROI: -0.49% Traditional ROI: 0.52%
140 SUGAR MILL DRIVE OSPREY, FL **BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE ESTATE with Lush Garden Landsc...	4 beds \| 4 baths \| 3,286 sq.ft.	$1,970,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 1.11% Airbnb Rental Income: $7455 Traditional Rental Income: $5508 Airbnb ROI: 1.4% Traditional ROI: 1.11%
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.	$705,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 3.12% Airbnb Rental Income: $3385 Traditional Rental Income: $3346 Airbnb ROI: 2.03% Traditional ROI: 3.12%
402 WALLS WAY OSPREY, FL Under contract-accepting backup offers. Welcome to timeless elegance and modern comfort in...	4 beds \| 4 baths \| 3,464 sq.ft.	$1,450,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 1.38% Airbnb Rental Income: $7455 Traditional Rental Income: $4908 Airbnb ROI: 2.21% Traditional ROI: 1.38%
1484 SEAFARER DRIVE OSPREY, FL Under contract-accepting backup offers. Welcome to Southbay Yacht & Racquet Club, one of t...	4 beds \| 4 baths \| 3,479 sq.ft.	$1,250,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 2.71% Airbnb Rental Income: $7455 Traditional Rental Income: $5355 Airbnb ROI: 3.29% Traditional ROI: 2.71%
85 SUGAR MILL DRIVE OSPREY, 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% Traditional cash on cash: -0.23% Airbnb Rental Income: $3385 Traditional Rental Income: $3755 Airbnb ROI: -0.79% Traditional ROI: -0.23%
140 N CASEY KEY ROAD OSPREY, FL Step into a world where the horizon meets the sea and every sunset paints a masterpiece. T...	3 beds \| 4 baths \| 2,473 sq.ft.	$2,500,000	Airbnb cash on cash: -0.86% Traditional cash on cash: -0.34% Airbnb Rental Income: $3385 Traditional Rental Income: $3839 Airbnb ROI: -0.86% Traditional ROI: -0.34%
17 BAYHEAD LANE OSPREY, FL Welcome to an exquisitely revitalized estate set amidst a stunning landscape that is sure ...	3 beds \| 2 baths \| 2,850 sq.ft.	$1,350,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 0.59% Airbnb Rental Income: $3385 Traditional Rental Income: $3214 Airbnb ROI: 0.13% Traditional ROI: 0.59%
510 LATITUDE LANE OSPREY, FL Stunning 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% Traditional cash on cash: 2.81% Airbnb Rental Income: $3385 Traditional Rental Income: $3427 Airbnb ROI: 1.47% Traditional ROI: 2.81%
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.	$599,000	Airbnb cash on cash: 8.33% Traditional cash on cash: 2.4% Airbnb Rental Income: $7455 Traditional Rental Income: $2711 Airbnb ROI: 8.33% Traditional ROI: 2.4%
38 W BAY STREET OSPREY, FL Live like youâre on vacation in this updated Key Westâstyle home West of the Trail. Up...	3 beds \| 2 baths \| 2,124 sq.ft.	$925,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 2.1% Airbnb Rental Income: $3385 Traditional Rental Income: $3382 Airbnb ROI: 1.22% Traditional ROI: 2.1%
594 PINE RANCH EAST ROAD OSPREY, FL Under contract-accepting backup offers. Discover this beautifully maintained 3-bedroom, 2-...	3 beds \| 3 baths \| 2,298 sq.ft.	$649,995	Airbnb cash on cash: 2.26% Traditional cash on cash: 7.51% Airbnb Rental Income: $3385 Traditional Rental Income: $5813 Airbnb ROI: 2.26% Traditional ROI: 7.51%
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.	$910,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 1.38% Airbnb Rental Income: $3385 Traditional Rental Income: $3211 Airbnb ROI: 0.69% Traditional ROI: 1.38%
813 OAK POND DRIVE OSPREY, FL One or more photo(s) has been virtually staged. WELCOME HOME!! THERE HAS BEEN NO FLOODING ...	4 beds \| 2 baths \| 1,981 sq.ft.	$550,000	Airbnb cash on cash: 9.6% Traditional cash on cash: 3.46% Airbnb Rental Income: $7455 Traditional Rental Income: $2867 Airbnb ROI: 9.6% Traditional ROI: 3.46%
340 OSPREY POINT DR OSPREY, FL Introducing The Grand Estate at The Oaks Baysideâa true masterpiece of refined living wi...	5 beds \| 7 baths \| 6,001 sq.ft.	$2,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.37% Airbnb Rental Income: $null Traditional Rental Income: $5440 Airbnb ROI: N/A Traditional ROI: 0.37%
866 PLACID LAKE DRIVE OSPREY, FL Immerse yourself in the blissful lifestyle located in the Woodlands of Rivendell, where th...	3 beds \| 2 baths \| 2,171 sq.ft.	$674,900	Airbnb cash on cash: 1.86% Traditional cash on cash: 2.81% Airbnb Rental Income: $3385 Traditional Rental Income: $3229 Airbnb ROI: 1.86% Traditional ROI: 2.81%
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.	$1,570,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 0.9% Airbnb Rental Income: $3385 Traditional Rental Income: $4285 Airbnb ROI: -0.23% Traditional ROI: 0.9%
819 SHADOW BAY WAY OSPREY, FL A 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% Traditional cash on cash: 3.3% Airbnb Rental Income: $7455 Traditional Rental Income: $3687 Airbnb ROI: 6.94% Traditional ROI: 3.3%
508 MEADOW SWEET CIRCLE OSPREY, FL The Cottages of Rivendell are highly desirable residences, offering an exclusive community...	2 beds \| 2 baths \| 1,604 sq.ft.	$499,900	Airbnb cash on cash: 2% Traditional cash on cash: 3.27% Airbnb Rental Income: $2934 Traditional Rental Income: $2852 Airbnb ROI: 2% Traditional ROI: 3.27%
32 Bay Avenue OSPREY, FL Located in the highly sought-after Bay Acres community, this home offers modern upgrades, ...	2 beds \| 2 baths \| 2,148 sq.ft.	$495,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 3.9% Airbnb Rental Income: $2934 Traditional Rental Income: $2685 Airbnb ROI: 2.98% Traditional ROI: 3.9%
523 HABITAT BOULEVARD OSPREY, FL In 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% Traditional cash on cash: 3.06% Airbnb Rental Income: $7455 Traditional Rental Income: $3885 Airbnb ROI: 5.98% Traditional ROI: 3.06%
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.	$1,695,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 1.27% Airbnb Rental Income: $3385 Traditional Rental Income: $4727 Airbnb ROI: -0.06% Traditional ROI: 1.27%
264 WOODS POINT ROAD OSPREY, FL One or more photo(s) has been virtually staged. Fresh paint is done, and new carpet is com...	2 beds \| 3 baths \| 2,837 sq.ft.	$485,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 2.98% Airbnb Rental Income: $2934 Traditional Rental Income: $3163 Airbnb ROI: 0.99% Traditional ROI: 2.98%
650 CRANE PRAIRIE WAY OSPREY, FL BEST PRICED HOME PER SQ FT in a 3-Mile Radius! Now Offered at $845,000 \| Lease Option/Purc...	4 beds \| 4 baths \| 3,183 sq.ft.	$845,000	Airbnb cash on cash: 5% Traditional cash on cash: 3.19% Airbnb Rental Income: $7455 Traditional Rental Income: $4603 Airbnb ROI: 5% Traditional ROI: 3.19%
312 YACHT HARBOR DRIVE OSPREY, FL One 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% Traditional cash on cash: 0.52% Airbnb Rental Income: $7455 Traditional Rental Income: $4850 Airbnb ROI: 1.07% Traditional ROI: 0.52%
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.	$409,900	Airbnb cash on cash: 4.15% Traditional cash on cash: 5.34% Airbnb Rental Income: $2934 Traditional Rental Income: $2715 Airbnb ROI: 4.15% Traditional ROI: 5.34%
566 OAK BAY DRIVE OSPREY, FL Seller is motivatedWelcome to Bay Oaks Estates. This 3-bedroom 2 bath plus den is a cl...	3 beds \| 2 baths \| 2,559 sq.ft.	$515,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 5.42% Airbnb Rental Income: $3385 Traditional Rental Income: $3444 Airbnb ROI: 3.74% Traditional ROI: 5.42%
219 KEEL WAY OSPREY, 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% Traditional cash on cash: 2.09% Airbnb Rental Income: $3385 Traditional Rental Income: $4181 Airbnb ROI: 0.67% Traditional ROI: 2.09%
227 SAINT JAMES PARK OSPREY, FL **TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect, Bo MacEwen, on the...	2 beds \| 2 baths \| 2,071 sq.ft.	$1,045,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 1.18% Airbnb Rental Income: $2934 Traditional Rental Income: $2769 Airbnb ROI: 0.65% Traditional ROI: 1.18%
370 SUGAR MILL DRIVE OSPREY, 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 Traditional cash on cash: 1.71% Airbnb Rental Income: $null Traditional Rental Income: $8602 Airbnb ROI: N/A Traditional ROI: 1.71%
662 FERNWALK LANE OSPREY, FL **FANTASTIC, FULLY RENOVATED ESTATE with LAKE / GARDEN VIEW is situated on a SERENE, INTER...	4 beds \| 4 baths \| 4,359 sq.ft.	$2,995,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 0.39% Airbnb Rental Income: $7455 Traditional Rental Income: $5371 Airbnb ROI: 0.63% Traditional ROI: 0.39%
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.	$11,750,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.84% Airbnb Rental Income: $null Traditional Rental Income: $9471 Airbnb ROI: N/A Traditional ROI: -0.84%
1049 N CASEY KEY ROAD OSPREY, FL Under 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% Traditional cash on cash: -0.36% Airbnb Rental Income: $3385 Traditional Rental Income: $4327 Airbnb ROI: -0.75% Traditional ROI: -0.36%
240 PATTERSON AVENUE OSPREY, FL Under contract-accepting backup offers. Charming 3-bedroom, 2-bath bungalow with no HOA or...	3 beds \| 2 baths \| 1,360 sq.ft.	$360,000	Airbnb cash on cash: 5.84% Traditional cash on cash: 6.03% Airbnb Rental Income: $3385 Traditional Rental Income: $2694 Airbnb ROI: 5.84% Traditional ROI: 6.03%

Your search for investment property begins and ends here

Single Family Homes for Sale in Osprey, FL

1363 NEW FOREST LANE

OSPREY, FL

2 beds | 2 baths | 1,738 sq.ft.

$499,000

Airbnb cash on cash: 2.19%

Traditional cash on cash: 2.91%

Airbnb Rental Income: $2934

Traditional Rental Income: $2592

Airbnb ROI: 2.19%

Traditional ROI: 2.91%

519 BAYVIEW AVENUE

OSPREY, FL

3 beds | 2 baths | 1,885 sq.ft.

$495,000

Airbnb cash on cash: 4.02%

Traditional cash on cash: 4%

Airbnb Rental Income: $3385

Traditional Rental Income: $2623

Airbnb ROI: 4.02%

Traditional ROI: 4%

563 PINE RANCH EAST ROAD

OSPREY, FL

3 beds | 2 baths | 2,346 sq.ft.

$675,000

Airbnb cash on cash: 2.21%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $3385

Traditional Rental Income: $3530

Airbnb ROI: 2.21%

Traditional ROI: 3.64%

901 REFLECTION WAY

OSPREY, FL

3 beds | 2 baths | 2,443 sq.ft.

$795,000

Airbnb cash on cash: 1.69%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $3385

Traditional Rental Income: $3009

Airbnb ROI: 1.69%

Traditional ROI: 2.2%

67 SUGAR MILL DRIVE

OSPREY, FL

4 beds | 5 baths | 4,020 sq.ft.

$1,999,000

Airbnb cash on cash: 1.44%

Traditional cash on cash: 1.65%

Airbnb Rental Income: $7455

Traditional Rental Income: $6415

Airbnb ROI: 1.44%

Traditional ROI: 1.65%

392 PARK TRACE BOULEVARD

OSPREY, FL

4 beds | 3 baths | 2,802 sq.ft.

$939,000

Airbnb cash on cash: 4.81%

Traditional cash on cash: 3.1%

Airbnb Rental Income: $7455

Traditional Rental Income: $4526

Airbnb ROI: 4.81%

Traditional ROI: 3.1%

852 MACEWEN DRIVE

OSPREY, FL

3 beds | 4 baths | 4,519 sq.ft.

$2,550,000

Airbnb cash on cash: -0.49%

Traditional cash on cash: 0.52%

Airbnb Rental Income: $3385

Traditional Rental Income: $5023

Airbnb ROI: -0.49%

Traditional ROI: 0.52%

140 SUGAR MILL DRIVE

OSPREY, FL

4 beds | 4 baths | 3,286 sq.ft.

$1,970,000

Airbnb cash on cash: 1.4%

Traditional cash on cash: 1.11%

Airbnb Rental Income: $7455

Traditional Rental Income: $5508

Airbnb ROI: 1.4%