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.

Investment Property for Sale in Osprey, FL

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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%
14041 Bellagio Way #218 OSPREY, FL Elevate your expectations with this elegant waterfront home! This 3-bedroom, 2-bath FULLY ...	3 beds \| 2 baths \| 2,374 sq.ft.	$1,099,000	Airbnb cash on cash: -0.9% Traditional cash on cash: -0.02% Airbnb Rental Income: $3385 Traditional Rental Income: $3567 Airbnb ROI: -0.9% Traditional ROI: -0.02%
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: 3.54% Traditional cash on cash: 2.09% Airbnb Rental Income: $7455 Traditional Rental Income: $4413 Airbnb ROI: 3.54% Traditional ROI: 2.09%
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%
1801 Highland Rd OSPREY, FL One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhom...	2 beds \| 2 baths \| 1,165 sq.ft.	$330,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 4.55% Airbnb Rental Income: $2934 Traditional Rental Income: $2223 Airbnb ROI: 4.66% Traditional ROI: 4.55%
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%
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%
5100 Jessie Harbor Dr #403 OSPREY, FL This meticulously maintained, waterfront residence is in an amenity-rich, gated community....	2 beds \| 2 baths \| 2,143 sq.ft.	$679,900	Airbnb cash on cash: -0.21% Traditional cash on cash: 1.83% Airbnb Rental Income: $2934 Traditional Rental Income: $3552 Airbnb ROI: -0.21% Traditional ROI: 1.83%
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.	$650,000	Airbnb cash on cash: 7.54% Traditional cash on cash: 4.27% Airbnb Rental Income: $7455 Traditional Rental Income: $4038 Airbnb ROI: 7.54% Traditional ROI: 4.27%
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%
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%
124 Revolution Way OSPREY, FL The only available home in the community with a 2 Car Garage! Welcome to Bay Street Villag...	2 beds \| 2 baths \| 1,574 sq.ft.	$388,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 5.38% Airbnb Rental Income: $2934 Traditional Rental Income: $3353 Airbnb ROI: 2.37% Traditional ROI: 5.38%
385 N Point Rd #304 OSPREY, FL **MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF R...	3 beds \| 3 baths \| 2,778 sq.ft.	$1,200,000	Airbnb cash on cash: -1.71% Traditional cash on cash: -1.04% Airbnb Rental Income: $3385 Traditional Rental Income: $3384 Airbnb ROI: -1.71% Traditional ROI: -1.04%
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%
177 Navigation Cir OSPREY, FL 10K PRICE REDUCTION! NEED A QUICK CLOSE? NO PROBLEM, SELLERS HAVE MOVED TO THEIR NEW HOME!...	3 beds \| 2 baths \| 1,581 sq.ft.	$369,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 3.44% Airbnb Rental Income: $3385 Traditional Rental Income: $2530 Airbnb ROI: 3.73% Traditional ROI: 3.44%
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%
409 N Point Rd #502 OSPREY, FL **GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The cov...	3 beds \| 3 baths \| 2,055 sq.ft.	$599,000	Airbnb cash on cash: -1.62% Traditional cash on cash: -0.65% Airbnb Rental Income: $3385 Traditional Rental Income: $3173 Airbnb ROI: -1.62% Traditional ROI: -0.65%
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%
401 N Point Rd #504 OSPREY, FL FULLY UPDATED â¢ WATER VIEWS â¢ PRIVATE 2-CAR GARAGE â¢ OFFICE/4TH BEDROOM OPTION F...	3 beds \| 3 baths \| 2,778 sq.ft.	$990,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 0.04% Airbnb Rental Income: $3385 Traditional Rental Income: $4047 Airbnb ROI: -1.5% Traditional ROI: 0.04%
291 Hidden Bay Dr #102 OSPREY, FL Centrally located between Sarasota and Venice, the gated community of Hidden Bay sits peac...	2 beds \| 2 baths \| 1,479 sq.ft.	$399,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 1.83% Airbnb Rental Income: $2934 Traditional Rental Income: $2454 Airbnb ROI: 1.3% Traditional ROI: 1.83%
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%
401 N Point Rd #304 OSPREY, FL Give yourself the gift of refined living in this expansive 2,778 square foot residenceât...	3 beds \| 3 baths \| 2,778 sq.ft.	$850,000	Airbnb cash on cash: -1.58% Traditional cash on cash: 0.04% Airbnb Rental Income: $3385 Traditional Rental Income: $3917 Airbnb ROI: -1.58% Traditional ROI: 0.04%
6100 Jessie Harbor Dr #203 OSPREY, FL Look no further! Blackburn Harbor is a boating & water sport enthusiast paradise! This b...	3 beds \| 3 baths \| 2,630 sq.ft.	$769,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 2.61% Airbnb Rental Income: $3385 Traditional Rental Income: $4358 Airbnb ROI: 0.2% Traditional ROI: 2.61%
14041 Bellagio Way #415 OSPREY, FL A boater's dream. Enjoy waterfront living in this luxury penthouse unit with breathtaking ...	3 beds \| 2 baths \| 1,736 sq.ft.	$699,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 0.89% Airbnb Rental Income: $3385 Traditional Rental Income: $3119 Airbnb ROI: 0.15% Traditional ROI: 0.89%
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%

Real Estate investment in Osprey, FL

There are 191 properties for sale in the city of Osprey . The median list price in Osprey is $749,950 and the average price per square foot is $290. In February 2026, the average monthly cash on cash return in Osprey is 2.00%. The average monthly rental income in Osprey is $3,347.

Osprey, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 191 investment properties available for sale in Osprey.

In 2026, the best neighborhood to buy investment property is OSPREY.

The ROI for Long-Term is higher than the Short-Term in Osprey with average rental income of $3,347.

Your search for investment property begins and ends here

Investment Property 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%

14041 Bellagio Way #218

OSPREY, FL

3 beds | 2 baths | 2,374 sq.ft.

$1,099,000

Airbnb cash on cash: -0.9%

Traditional cash on cash: -0.02%

Airbnb Rental Income: $3385

Traditional Rental Income: $3567

Airbnb ROI: -0.9%

Traditional ROI: -0.02%

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%