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 51 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. **NEWLY RENOVATED, SPACIOUS, GOLF COURSE E...	4 beds \| 6 baths \| 9,081 sq.ft.	$4,195,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 0.23% Airbnb Rental Income: $7455 Traditional Rental Income: $7085 Airbnb ROI: -0.04% Traditional ROI: 0.23%
462 E MACEWEN DRIVE OSPREY, FL This completely remodeled home in The Oaks Clubside, set on nearly an acre of mature, meti...	3 beds \| 3 baths \| 2,611 sq.ft.	$1,550,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 1.48% Airbnb Rental Income: $3385 Traditional Rental Income: $4444 Airbnb ROI: 0.22% Traditional ROI: 1.48%
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.	$525,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 2.72% Airbnb Rental Income: $2934 Traditional Rental Income: $2592 Airbnb ROI: 2.04% Traditional ROI: 2.72%
519 BAYVIEW AVENUE OSPREY, FL Boating Community, Bay Acres! RV and Boat Parking pad 42'x16' with electric hook-up, and H...	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%
104 PARK TRACE BOULEVARD OSPREY, FL Welcome to your dream home in beautiful Osprey, Florida inside PARK TRACE! This expansive ...	4 beds \| 3 baths \| 2,557 sq.ft.	$635,000	Airbnb cash on cash: 8.28% Traditional cash on cash: 4.93% Airbnb Rental Income: $7455 Traditional Rental Income: $4038 Airbnb ROI: 8.28% Traditional ROI: 4.93%
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.	$815,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 2.12% Airbnb Rental Income: $3385 Traditional Rental Income: $3009 Airbnb ROI: 1.63% Traditional ROI: 2.12%
67 SUGAR MILL DRIVE OSPREY, FL This is your rare chance to claim a spectacular estate in Sarasotaâs premier golf and co...	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%
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%
116 VILLA DRIVE #116 OSPREY, FL Under contract-accepting backup offers. Bring your boat and move right in! This home has b...	2 beds \| 2 baths \| 1,221 sq.ft.	$525,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 2.41% Airbnb Rental Income: $2934 Traditional Rental Income: $2392 Airbnb ROI: 2.14% Traditional ROI: 2.41%
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 Welcome to timeless elegance and modern comfort in The Oaks Clubside. This stunning 4-bedr...	4 beds \| 4 baths \| 3,464 sq.ft.	$1,500,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 1.3% Airbnb Rental Income: $7455 Traditional Rental Income: $4908 Airbnb ROI: 2.1% Traditional ROI: 1.3%
1484 SEAFARER DRIVE OSPREY, FL Welcome to Southbay Yacht & Racquet Club, one of the Gulf Coastâs most coveted communiti...	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%
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.	$1,375,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 0.56% Airbnb Rental Income: $3385 Traditional Rental Income: $3214 Airbnb ROI: 0.11% Traditional ROI: 0.56%
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.	$2,299,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.08% Airbnb Rental Income: $null Traditional Rental Income: $5559 Airbnb ROI: N/A Traditional ROI: 1.08%
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%
594 PINE RANCH EAST ROAD OSPREY, FL Discover this beautifully maintained 3-bedroom, 2-bathroom home nestled in a peaceful, pri...	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.	$560,000	Airbnb cash on cash: 9.42% Traditional cash on cash: 3.38% Airbnb Rental Income: $7455 Traditional Rental Income: $2867 Airbnb ROI: 9.42% Traditional ROI: 3.38%
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%
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%
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. SELLER WILL CONSIDER LEASE PURCHASE. Try i...	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%
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.	$530,000	Airbnb cash on cash: 3.6% Traditional cash on cash: 5.24% Airbnb Rental Income: $3385 Traditional Rental Income: $3444 Airbnb ROI: 3.6% Traditional ROI: 5.24%
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%
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 Seize the opportunity to own a piece of paradise on the exclusive North Casey Key. This sp...	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%
51 WEBB STREET OSPREY, FL Location, Location, Location! Nestled West of the Trail in the heart of Osprey, this beaut...	3 beds \| 3 baths \| 2,130 sq.ft.	$614,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 3.93% Airbnb Rental Income: $3385 Traditional Rental Income: $3469 Airbnb ROI: 2.47% Traditional ROI: 3.93%
826 OAK BRIAR LANE OSPREY, FL Under contract-accepting backup offers. Welcome to this MODERN 4-Bedroom, 3-Bath POOL HOME...	4 beds \| 3 baths \| 2,589 sq.ft.	$735,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 3.64% Airbnb Rental Income: $7455 Traditional Rental Income: $3748 Airbnb ROI: 6.96% Traditional ROI: 3.64%
240 PATTERSON AVENUE OSPREY, FL Charming 3-bedroom, 2-bath bungalow with no HOA or deed restrictionsâperfect for boaters...	3 beds \| 2 baths \| 1,360 sq.ft.	$365,000	Airbnb cash on cash: 5.75% Traditional cash on cash: 5.93% Airbnb Rental Income: $3385 Traditional Rental Income: $2694 Airbnb ROI: 5.75% Traditional ROI: 5.93%
600 EAGLE WATCH LANE OSPREY, FL Located on one of the most desirable streets in The Oaks Clubside, this completely renovat...	3 beds \| 3 baths \| 3,681 sq.ft.	$1,990,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 0.12% Airbnb Rental Income: $3385 Traditional Rental Income: $3674 Airbnb ROI: -0.45% Traditional ROI: 0.12%
13 BAYHEAD LANE OSPREY, FL **IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANC...	2 beds \| 2 baths \| 2,310 sq.ft.	$965,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 1.42% Airbnb Rental Income: $2934 Traditional Rental Income: $3074 Airbnb ROI: 0.51% Traditional ROI: 1.42%
238 LOOKOUT POINT DRIVE OSPREY, FL Nestled in the heart of Southbay Yacht & Racquet Club, this exquisitely renovated and impe...	3 beds \| 3 baths \| 2,676 sq.ft.	$959,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 2.42% Airbnb Rental Income: $3385 Traditional Rental Income: $3861 Airbnb ROI: 1.05% Traditional ROI: 2.42%
750 ANNA HOPE LANE OSPREY, FL Impeccable style and effortless grace define this Rivendell home, which stands as a testam...	4 beds \| 2 baths \| 2,135 sq.ft.	$669,000	Airbnb cash on cash: 7.34% Traditional cash on cash: 3.18% Airbnb Rental Income: $7455 Traditional Rental Income: $3428 Airbnb ROI: 7.34% Traditional ROI: 3.18%
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.	$444,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.45% Airbnb Rental Income: $3385 Traditional Rental Income: $2349 Airbnb ROI: 4.13% Traditional ROI: 3.45%

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.

$4,195,000

Airbnb cash on cash: -0.04%

Traditional cash on cash: 0.23%

Airbnb Rental Income: $7455

Traditional Rental Income: $7085

Airbnb ROI: -0.04%

Traditional ROI: 0.23%

462 E MACEWEN DRIVE

OSPREY, FL

3 beds | 3 baths | 2,611 sq.ft.

$1,550,000

Airbnb cash on cash: 0.22%

Traditional cash on cash: 1.48%

Airbnb Rental Income: $3385

Traditional Rental Income: $4444

Airbnb ROI: 0.22%

Traditional ROI: 1.48%

1363 NEW FOREST LANE

OSPREY, FL

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

$525,000

Airbnb cash on cash: 2.04%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $2934

Traditional Rental Income: $2592

Airbnb ROI: 2.04%

Traditional ROI: 2.72%

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%

104 PARK TRACE BOULEVARD

OSPREY, FL

4 beds | 3 baths | 2,557 sq.ft.

$635,000

Airbnb cash on cash: 8.28%

Traditional cash on cash: 4.93%

Airbnb Rental Income: $7455

Traditional Rental Income: $4038

Airbnb ROI: 8.28%

Traditional ROI: 4.93%

901 REFLECTION WAY

OSPREY, FL

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

$815,000

Airbnb cash on cash: 1.63%

Traditional cash on cash: 2.12%

Airbnb Rental Income: $3385

Traditional Rental Income: $3009

Airbnb ROI: 1.63%

Traditional ROI: 2.12%

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%

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%