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

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%
1801 HIGHLAND ROAD 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.	$350,000	Airbnb cash on cash: 4.41% Traditional cash on cash: 4.31% Airbnb Rental Income: $2934 Traditional Rental Income: $2223 Airbnb ROI: 4.41% Traditional ROI: 4.31%
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%
14041 BELLAGIO WAY #214 OSPREY, FL One or more photo(s) has been virtually staged. Massive Price Reduction! Original Listing ...	3 beds \| 2 baths \| 1,799 sq.ft.	$675,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 1.18% Airbnb Rental Income: $3385 Traditional Rental Income: $3196 Airbnb ROI: 0.28% Traditional ROI: 1.18%
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%
780 SARABAY ROAD #16 OSPREY, FL Boater's Paradise! Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely de...	2 beds \| 2 baths \| 1,574 sq.ft.	$479,900	Airbnb cash on cash: -1.65% Traditional cash on cash: 0.16% Airbnb Rental Income: $2934 Traditional Rental Income: $3068 Airbnb ROI: -1.65% Traditional ROI: 0.16%
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%
409 N POINT ROAD #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.	$685,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 2.58% Airbnb Rental Income: $3385 Traditional Rental Income: $3173 Airbnb ROI: 1.73% Traditional ROI: 2.58%
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%
401 N POINT ROAD #901 OSPREY, FL This opulent 3 bedroom plus den, 3 bath residence with a PRIVATE 2 CAR GARAGE located in M...	3 beds \| 3 baths \| 2,594 sq.ft.	$1,549,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 0.36% Airbnb Rental Income: $3385 Traditional Rental Income: $3420 Airbnb ROI: -0.19% Traditional ROI: 0.36%
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%
401 N POINT ROAD #504 OSPREY, FL FULLY UPDATED ~ WATER VIEWS ~ PRIVATE 2 CAR GARAGE ~ OFFICE/4TH BEDROOM OPTION ~ The eye o...	3 beds \| 3 baths \| 2,778 sq.ft.	$1,150,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 1.59% Airbnb Rental Income: $3385 Traditional Rental Income: $4047 Airbnb ROI: 0.26% Traditional ROI: 1.59%
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%
401 N POINT ROAD #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.	$900,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 2.14% Airbnb Rental Income: $3385 Traditional Rental Income: $3917 Airbnb ROI: 0.61% Traditional ROI: 2.14%
207 WOODLAND DRIVE #207 OSPREY, FL Under contract-accepting backup offers. Welcome to this beautifully appointed, well-cared ...	2 beds \| 2 baths \| 1,325 sq.ft.	$269,999	Airbnb cash on cash: 6.14% Traditional cash on cash: 5.95% Airbnb Rental Income: $2934 Traditional Rental Income: $2210 Airbnb ROI: 6.14% Traditional ROI: 5.95%
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%
401 N POINT ROAD #301 OSPREY, FL One or more photo(s) has been virtually staged. Enter through the secure foyer and take th...	3 beds \| 3 baths \| 2,594 sq.ft.	$399,900	Airbnb cash on cash: 3.01% Traditional cash on cash: 4.88% Airbnb Rental Income: $3385 Traditional Rental Income: $3335 Airbnb ROI: 3.01% Traditional ROI: 4.88%
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%
232 HIDDEN BAY DRIVE #504 OSPREY, FL This condominium has it all! Fantastic water views along the Intracoastal. Amazing sunsets...	3 beds \| 3 baths \| 2,000 sq.ft.	$599,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 4.01% Airbnb Rental Income: $3385 Traditional Rental Income: $3577 Airbnb ROI: 2.32% Traditional ROI: 4.01%
758 PINE RUN DRIVE #758 OSPREY, FL This home was professionally inspected by a Contractor following Hurricanes Helene and Mil...	2 beds \| 2 baths \| 1,184 sq.ft.	$250,300	Airbnb cash on cash: 3.68% Traditional cash on cash: 3.06% Airbnb Rental Income: $2934 Traditional Rental Income: $2110 Airbnb ROI: 3.68% Traditional ROI: 3.06%
401 N POINT RD APT 301 OSPREY, FL Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 3 baths \| 2,594 sq.ft.	$751,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 0.54% Airbnb Rental Income: $3385 Traditional Rental Income: $3127 Airbnb ROI: -0.16% Traditional ROI: 0.54%
385 N POINT ROAD #404 OSPREY, FL **STUNNINGLY UPDATED CONDO with Breathtaking Water & Preserve Views that rival those of hi...	3 beds \| 3 baths \| 2,778 sq.ft.	$925,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 2.38% Airbnb Rental Income: $3385 Traditional Rental Income: $4038 Airbnb ROI: 0.75% Traditional ROI: 2.38%
401 N POINT ROAD #603 OSPREY, FL One or more photo(s) has been virtually staged. BEAUTIFUL FULL WATER VIEW AND 2ND FLOOR PR...	3 beds \| 3 baths \| 2,203 sq.ft.	$699,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 2.6% Airbnb Rental Income: $3385 Traditional Rental Income: $3228 Airbnb ROI: 1.68% Traditional ROI: 2.6%
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%
3603 N POINT ROAD #202 OSPREY, FL ELEGANT and SPACIOUS CORNER CONDO UNIT â NEARLY 3200sf â With MULTIPLE BALCONIES f...	3 beds \| 3 baths \| 3,147 sq.ft.	$789,900	Airbnb cash on cash: 1.42% Traditional cash on cash: 2.97% Airbnb Rental Income: $3385 Traditional Rental Income: $3774 Airbnb ROI: 1.42% Traditional ROI: 2.97%
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%
3621 NORTH POINT ROAD #603 OSPREY, FL Prepare to be captivated by this COMPLETELY UPDATED, meticulously maintained, and thoughtf...	3 beds \| 3 baths \| 2,680 sq.ft.	$1,350,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 0.3% Airbnb Rental Income: $3385 Traditional Rental Income: $3143 Airbnb ROI: -0.11% Traditional ROI: 0.3%
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%
280 HIDDEN BAY DRIVE #202 OSPREY, FL READY FOR IMMEDIATE OCCUPANCY! Modern Elegance at Edgewater: A Luxurious Haven Overlookin...	3 beds \| 2 baths \| 1,937 sq.ft.	$780,250	Airbnb cash on cash: -1.14% Traditional cash on cash: 0.23% Airbnb Rental Income: $3385 Traditional Rental Income: $3629 Airbnb ROI: -1.14% Traditional ROI: 0.23%
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%
707 PINE RUN DRIVE OSPREY, FL Nestled in a nature enthusiastâs haven is an architecturally stunning community. Located...	2 beds \| 2 baths \| 1,379 sq.ft.	$289,000	Airbnb cash on cash: 5.78% Traditional cash on cash: 7.21% Airbnb Rental Income: $2934 Traditional Rental Income: $2644 Airbnb ROI: 5.78% Traditional ROI: 7.21%

Real Estate investment in Osprey, FL

There are 100 properties for sale in the city of Osprey . The median list price in Osprey is $782,875 and the average price per square foot is $313. In October 2025, the average monthly cash on cash return in Osprey is 3.00%. The average monthly rental income in Osprey is $3,428.

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

There are 100 investment properties available for sale in Osprey.

In 2025, 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 $3,428.

Your search for investment property begins and ends here

Investment Property 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%

1801 HIGHLAND ROAD

OSPREY, FL

2 beds | 2 baths | 1,165 sq.ft.

$350,000

Airbnb cash on cash: 4.41%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $2934

Traditional Rental Income: $2223

Airbnb ROI: 4.41%

Traditional ROI: 4.31%

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%

14041 BELLAGIO WAY #214

OSPREY, FL

3 beds | 2 baths | 1,799 sq.ft.

$675,000

Airbnb cash on cash: 0.28%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $3385

Traditional Rental Income: $3196

Airbnb ROI: 0.28%

Traditional ROI: 1.18%

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%

780 SARABAY ROAD #16

OSPREY, FL

2 beds | 2 baths | 1,574 sq.ft.

$479,900

Airbnb cash on cash: -1.65%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $2934

Traditional Rental Income: $3068

Airbnb ROI: -1.65%