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 133 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 Dr OSPREY, FL One or more photo(s) has been virtually staged. Set on a private cul-de-sac within The Oak...	4 beds \| 4 baths \| 9,081 sq.ft.	$3,890,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 0.23% Airbnb Rental Income: $7455 Traditional Rental Income: $7085 Airbnb ROI: -0.06% Traditional ROI: 0.23%
730 Sarabay Rd OSPREY, FL Premier Intracoastal Estate in Osprey 4 Bedrooms \| 6 Bathrooms \| 6,308 Sq. Ft. \| 2 Waterf...	4 beds \| 5 baths \| 6,308 sq.ft.	$5,495,000	Airbnb cash on cash: -0.69% Traditional cash on cash: -0.13% Airbnb Rental Income: $7455 Traditional Rental Income: $8849 Airbnb ROI: -0.69% Traditional ROI: -0.13%
1303 Thornapple Dr OSPREY, FL INCREDIBLE Pool Home in INCREDIBLE Community!...You Will Be Impressed by this Well-Appoint...	3 beds \| 2 baths \| 1,929 sq.ft.	$699,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.24% Airbnb Rental Income: $3385 Traditional Rental Income: $4487 Airbnb ROI: 1.4% Traditional ROI: 4.24%
144 N Casey Key Rd OSPREY, FL A striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless r...	4 beds \| 5 baths \| 5,397 sq.ft.	$5,495,000	Airbnb cash on cash: -0.84% Traditional cash on cash: -0.27% Airbnb Rental Income: $7455 Traditional Rental Income: $8929 Airbnb ROI: -0.84% Traditional ROI: -0.27%
742 Harms Dr OSPREY, FL ATTENTION NATURE LOVERS: Your Own Private Hide-Away on one-half acre yet conveniently loca...	3 beds \| 2 baths \| 1,293 sq.ft.	$515,000	Airbnb cash on cash: 3.99% Traditional cash on cash: 3.11% Airbnb Rental Income: $3385 Traditional Rental Income: $2206 Airbnb ROI: 3.99% Traditional ROI: 3.11%
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%
135 Tina Island Dr OSPREY, FL If you are ready to retreat to paradise, look no more. This home is amazing. Located in a ...	3 beds \| 4 baths \| 2,572 sq.ft.	$3,300,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 0.35% Airbnb Rental Income: $3385 Traditional Rental Income: $5326 Airbnb ROI: -0.53% Traditional ROI: 0.35%
403 Longbow Trl 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.	$1,175,000	Airbnb cash on cash: 3.62% Traditional cash on cash: 2.15% Airbnb Rental Income: $7455 Traditional Rental Income: $4413 Airbnb ROI: 3.62% Traditional ROI: 2.15%
494 MEADOW SWEET CIRCLE OSPREY, FL Under contract-accepting backup offers. Modern farmhouse style in the Rivendell Cottages w...	3 beds \| 2 baths \| 1,791 sq.ft.	$595,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 2.65% Airbnb Rental Income: $3385 Traditional Rental Income: $2765 Airbnb ROI: 2.41% Traditional ROI: 2.65%
1019 SCHERER WAY OSPREY, FL Welcome to this beautiful 4 bedroom 3 full bath home situated in the desirable community o...	4 beds \| 3 baths \| 2,498 sq.ft.	$735,000	Airbnb cash on cash: 6.64% Traditional cash on cash: 3.21% Airbnb Rental Income: $7455 Traditional Rental Income: $3677 Airbnb ROI: 6.64% Traditional ROI: 3.21%
764 Sarabay Rd #8 OSPREY, FL Welcome to Paradise on Little Sarasota Bay! Heron Bay is an intimate, maintenance free, b...	2 beds \| 2 baths \| 1,392 sq.ft.	$450,000	Airbnb cash on cash: -0.94% Traditional cash on cash: -0.94% Airbnb Rental Income: $2934 Traditional Rental Income: $2252 Airbnb ROI: -0.94% Traditional ROI: -0.94%
106 VILLA DRIVE #106 OSPREY, FL Under contract-accepting backup offers. Located West of the Trail in Sorrento Shores, Ospr...	2 beds \| 2 baths \| 1,578 sq.ft.	$199,000	Airbnb cash on cash: 6.3% Traditional cash on cash: 8.63% Airbnb Rental Income: $2934 Traditional Rental Income: $2696 Airbnb ROI: 6.3% Traditional ROI: 8.63%
104 Park Trace Blvd 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.	$595,000	Airbnb cash on cash: 8.32% Traditional cash on cash: 4.75% Airbnb Rental Income: $7455 Traditional Rental Income: $4038 Airbnb ROI: 8.32% Traditional ROI: 4.75%
146 Willow Bend Way OSPREY, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 3 baths \| 2,540 sq.ft.	$699,000	Airbnb cash on cash: 7.29% Traditional cash on cash: 3.7% Airbnb Rental Income: $7455 Traditional Rental Income: $3683 Airbnb ROI: 7.29% Traditional ROI: 3.7%
854 N Casey Key Rd OSPREY, FL Under contract-accepting backup offers. Nestled on the serene expanse of North Casey Key, ...	4 beds \| 4 baths \| 3,462 sq.ft.	$4,750,000	Airbnb cash on cash: -0.39% Traditional cash on cash: -0.7% Airbnb Rental Income: $7455 Traditional Rental Income: $4682 Airbnb ROI: -0.39% Traditional ROI: -0.7%
392 PARK TRACE BOULEVARD OSPREY, FL Under 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% Traditional cash on cash: 3.1% Airbnb Rental Income: $7455 Traditional Rental Income: $4526 Airbnb ROI: 4.81% Traditional ROI: 3.1%
76 Osprey Point Dr OSPREY, FL COMPLETELY UPGRADED IS NOT AN EXAGGERATION! This Bo MacEwenâdesigned 3-bedroom, 4.5-bath...	3 beds \| 4 baths \| 4,364 sq.ft.	$1,650,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 1.93% Airbnb Rental Income: $3385 Traditional Rental Income: $6365 Airbnb ROI: -0.5% Traditional ROI: 1.93%
852 Macewen Dr OSPREY, FL CHARMING and PRIVATE, GOLF COURSE ESTATE is located behind the Secure Gates of the hig...	3 beds \| 3 baths \| 4,519 sq.ft.	$2,495,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 0.56% Airbnb Rental Income: $3385 Traditional Rental Income: $5023 Airbnb ROI: -0.48% Traditional ROI: 0.56%
49 Osprey Point Dr OSPREY, FL This 3 bedroom + office, 3.5 bath Oaks Bayside gem offers gorgeous lake views. As you ent...	4 beds \| 3 baths \| 3,953 sq.ft.	$2,500,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 0.23% Airbnb Rental Income: $7455 Traditional Rental Income: $4191 Airbnb ROI: 1.02% Traditional ROI: 0.23%
75 Osprey Point Dr OSPREY, FL STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood on...	4 beds \| 4 baths \| 4,001 sq.ft.	$1,775,000	Airbnb cash on cash: 1.15% Traditional cash on cash: -0.11% Airbnb Rental Income: $7455 Traditional Rental Income: $3945 Airbnb ROI: 1.15% Traditional ROI: -0.11%
140 Sugar Mill Dr OSPREY, 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: 1.39% Traditional cash on cash: 1.11% Airbnb Rental Income: $7455 Traditional Rental Income: $5508 Airbnb ROI: 1.39% Traditional ROI: 1.11%
110 Pine Ave 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: 3.15% Airbnb Rental Income: $3385 Traditional Rental Income: $3346 Airbnb ROI: 2.06% Traditional ROI: 3.15%
85 Sugar Mill Dr 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%
120 Villa Dr #120 OSPREY, FL MAINTENANCE-FREE & MOVE-IN READY!!! âWest of the Trailâ WATERFRONT VILLA WITH BOAT DOC...	2 beds \| 2 baths \| 1,404 sq.ft.	$515,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 2.07% Airbnb Rental Income: $2934 Traditional Rental Income: $2272 Airbnb ROI: 2.04% Traditional ROI: 2.07%
140 N Casey Key Rd OSPREY, FL LIVE THE ULTIMATE COASTAL LIFESTYLE on the coveted Casey Key barrier island at this vibran...	3 beds \| 3 baths \| 2,473 sq.ft.	$2,100,000	Airbnb cash on cash: -0.84% Traditional cash on cash: -0.22% Airbnb Rental Income: $3385 Traditional Rental Income: $3839 Airbnb ROI: -0.84% Traditional ROI: -0.22%
17 Bayhead Ln 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.	$1,300,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 0.31% Airbnb Rental Income: $3385 Traditional Rental Income: $3214 Airbnb ROI: -0.17% Traditional ROI: 0.31%
510 Latitude Ln OSPREY, FL Stunning residence crafted by renowned builder Lee Wetherington. Nestled on a southern exp...	3 beds \| 2 baths \| 2,298 sq.ft.	$599,900	Airbnb cash on cash: 1.61% Traditional cash on cash: 3.03% Airbnb Rental Income: $3385 Traditional Rental Income: $3427 Airbnb ROI: 1.61% Traditional ROI: 3.03%
1211 Lost Creek Ct OSPREY, FL DO NOT MISS THIS OPPORTUNITY to own this beautiful and spacious 4-Bed, 3-Bath, rare 3-Car ...	4 beds \| 3 baths \| 2,876 sq.ft.	$829,000	Airbnb cash on cash: 5.89% Traditional cash on cash: 3.69% Airbnb Rental Income: $7455 Traditional Rental Income: $4324 Airbnb ROI: 5.89% Traditional ROI: 3.69%
2043 Cordes St OSPREY, FL Charming & Versatile Home Near the Beaches! This cute and cozy, well-maintained 3-bedroom...	3 beds \| 2 baths \| 1,186 sq.ft.	$289,000	Airbnb cash on cash: 7.4% Traditional cash on cash: 6.87% Airbnb Rental Income: $3385 Traditional Rental Income: $2488 Airbnb ROI: 7.4% Traditional ROI: 6.87%
472 Park Trace Blvd OSPREY, FL The gem of a neighborhood that is Park Trace Estates welcomes you, now, and this move in r...	4 beds \| 2 baths \| 2,217 sq.ft.	$645,000	Airbnb cash on cash: 8.18% Traditional cash on cash: 3.72% Airbnb Rental Income: $7455 Traditional Rental Income: $3339 Airbnb ROI: 8.18% Traditional ROI: 3.72%
597 Oak River Ct OSPREY, FL Stunning, fully remodeled 4-bedroom, 2-bathroom home tucked away in a quiet cul-de-sac in ...	4 beds \| 2 baths \| 2,111 sq.ft.	$724,900	Airbnb cash on cash: 7.01% Traditional cash on cash: 3.05% Airbnb Rental Income: $7455 Traditional Rental Income: $3347 Airbnb ROI: 7.01% Traditional ROI: 3.05%
691 EAGLE WATCH LANE OSPREY, FL Under contract-accepting backup offers. Nestled within the exclusive gated community of th...	4 beds \| 7 baths \| 6,705 sq.ft.	$3,995,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 0.59% Airbnb Rental Income: $7455 Traditional Rental Income: $8601 Airbnb ROI: -0.1% Traditional ROI: 0.59%
365 S Shore Dr 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.	$1,380,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 0.9% Airbnb Rental Income: $3385 Traditional Rental Income: $3253 Airbnb ROI: 0.41% Traditional ROI: 0.9%
180 Lookout Point Dr OSPREY, FL One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the ...	5 beds \| 3 baths \| 3,236 sq.ft.	$2,274,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.1% Airbnb Rental Income: $null Traditional Rental Income: $5559 Airbnb ROI: N/A Traditional ROI: 1.1%
4428 Conchfish Ln 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 Under contract-accepting backup offers. Live like youâre on vacation in this updated Key...	3 beds \| 2 baths \| 2,124 sq.ft.	$899,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 2.18% Airbnb Rental Income: $3385 Traditional Rental Income: $3382 Airbnb ROI: 1.29% Traditional ROI: 2.18%
433 E Macewen Dr OSPREY, FL An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths...	4 beds \| 3 baths \| 4,012 sq.ft.	$2,250,000	Airbnb cash on cash: 1% Traditional cash on cash: 1.01% Airbnb Rental Income: $7455 Traditional Rental Income: $6046 Airbnb ROI: 1% Traditional ROI: 1.01%
524 Sarabay Rd OSPREY, FL NEW ROOF just installed! This 3 bedroom 2 bath home has a Large yard perfect for your toys...	3 beds \| 2 baths \| 1,760 sq.ft.	$419,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 6.93% Airbnb Rental Income: $3385 Traditional Rental Income: $3355 Airbnb ROI: 5.09% Traditional ROI: 6.93%
293 Turquoise Ln 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% Traditional cash on cash: 0.69% Airbnb Rental Income: $3385 Traditional Rental Income: $3211 Airbnb ROI: 0% Traditional ROI: 0.69%
455 N Shore Dr OSPREY, FL Under contract-accepting backup offers. Welcome to the Ultimate Florida Paradise at 455 N ...	2 beds \| 2 baths \| 1,229 sq.ft.	$549,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 3.46% Airbnb Rental Income: $2934 Traditional Rental Income: $2588 Airbnb ROI: 2.81% Traditional ROI: 3.46%

Your search for investment property begins and ends here

Single Family Homes for Sale in Osprey, FL

854 Macewen Dr

OSPREY, FL

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

$3,890,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 0.23%

Airbnb Rental Income: $7455

Traditional Rental Income: $7085

Airbnb ROI: -0.06%

Traditional ROI: 0.23%

730 Sarabay Rd

OSPREY, FL

4 beds | 5 baths | 6,308 sq.ft.

$5,495,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: -0.13%

Airbnb Rental Income: $7455

Traditional Rental Income: $8849

Airbnb ROI: -0.69%

Traditional ROI: -0.13%

1303 Thornapple Dr

OSPREY, FL

3 beds | 2 baths | 1,929 sq.ft.

$699,000

Airbnb cash on cash: 1.4%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $3385

Traditional Rental Income: $4487

Airbnb ROI: 1.4%

Traditional ROI: 4.24%

144 N Casey Key Rd

OSPREY, FL

4 beds | 5 baths | 5,397 sq.ft.

$5,495,000

Airbnb cash on cash: -0.84%

Traditional cash on cash: -0.27%

Airbnb Rental Income: $7455

Traditional Rental Income: $8929

Airbnb ROI: -0.84%

Traditional ROI: -0.27%

742 Harms Dr

OSPREY, FL

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

$515,000

Airbnb cash on cash: 3.99%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $3385

Traditional Rental Income: $2206

Airbnb ROI: 3.99%

Traditional ROI: 3.11%

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%

135 Tina Island Dr

OSPREY, FL

3 beds | 4 baths | 2,572 sq.ft.

$3,300,000

Airbnb cash on cash: -0.53%

Traditional cash on cash: 0.35%

Airbnb Rental Income: $3385

Traditional Rental Income: $5326

Airbnb ROI: -0.53%

Traditional ROI: 0.35%

403 Longbow Trl

OSPREY, FL

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

$1,175,000

Airbnb cash on cash: 3.62%

Traditional cash on cash: 2.15%

Airbnb Rental Income: $7455

Traditional Rental Income: $4413

Airbnb ROI: 3.62%