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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
854 MACEWEN DRIVEOSPREY, FLOne 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%
|
144 N CASEY KEY ROADOSPREY, FLA striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless r... |
4 beds | 6 baths | 5,397 sq.ft. |
$6,790,000 |
Airbnb cash on cash: -0.87%
|
462 E MACEWEN DRIVEOSPREY, FLThis 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%
|
1363 NEW FOREST LANEOSPREY, FLWelcome 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%
|
1801 HIGHLAND ROADOSPREY, FLEnjoy this Key West-style townhome in Towns-End Shores-maintenance-free living at its best... |
2 beds | 2 baths | 1,165 sq.ft. |
$372,500 |
Airbnb cash on cash: 4.18%
|
519 BAYVIEW AVENUEOSPREY, FLBoating 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%
|
104 PARK TRACE BOULEVARDOSPREY, FLWelcome to your dream home in beautiful Osprey, Florida inside PARK TRACE! This expansive ... |
4 beds | 3 baths | 2,557 sq.ft. |
$647,000 |
Airbnb cash on cash: 8.11%
|
901 REFLECTION WAYOSPREY, FLLOCATION! 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%
|
14041 BELLAGIO WAY #214OSPREY, FLOne 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%
|
67 SUGAR MILL DRIVEOSPREY, FLThis 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%
|
780 SARABAY ROAD #16OSPREY, FLWelcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situat... |
2 beds | 2 baths | 1,574 sq.ft. |
$499,900 |
Airbnb cash on cash: -1.63%
|
852 MACEWEN DRIVEOSPREY, 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%
|
116 VILLA DRIVE #116OSPREY, FLUnder 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%
|
409 N POINT ROAD #502OSPREY, 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%
|
140 SUGAR MILL DRIVEOSPREY, 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%
|
110 PINE AVENUEOSPREY, FLHeart 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%
|
402 WALLS WAYOSPREY, FLWelcome 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%
|
1484 SEAFARER DRIVEOSPREY, FLWelcome 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%
|
401 N POINT ROAD #901OSPREY, FLThis 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%
|
401 N POINT ROAD #504OSPREY, FLFULLY 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%
|
401 N POINT ROAD #304OSPREY, FLGive 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%
|
1164 BEACHCOMBER COURT #19OSPREY, FLUnder contract-accepting backup offers. Welcome to the exclusive Blackburn Point Marina Vi... |
3 beds | 3 baths | 1,952 sq.ft. |
$550,000 |
Airbnb cash on cash: 0.7%
|
207 WOODLAND DRIVE #207OSPREY, FLWelcome to this beautifully appointed, well-cared for and fully furnished 2-bedroom, 2-bat... |
2 beds | 2 baths | 1,325 sq.ft. |
$269,999 |
Airbnb cash on cash: 6.14%
|
180 LOOKOUT POINT DRIVEOSPREY, FLOne 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
|
4428 CONCHFISH LANEOSPREY, FLChic 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%
|
401 N POINT ROAD #301OSPREY, FLOne 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%
|
594 PINE RANCH EAST ROADOSPREY, FLDiscover 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%
|
758 PINE RUN DRIVE #758OSPREY, FLThis home was professionally inspected by a Contractor following Hurricanes Helene and Mil... |
2 beds | 2 baths | 1,184 sq.ft. |
$256,600 |
Airbnb cash on cash: 3.56%
|
401 N POINT RD APT 301OSPREY, FLInvest 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%
|
385 N POINT ROAD #404OSPREY, 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%
|
401 N POINT ROAD #603OSPREY, FLOne 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%
|
293 TURQUOISE LANEOSPREY, 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%
|
3603 N POINT ROAD #202OSPREY, 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%
|
813 OAK POND DRIVEOSPREY, FLOne 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%
|
3621 NORTH POINT ROAD #603OSPREY, FLPrepare 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%
|
340 OSPREY POINT DROSPREY, FLIntroducing 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
|
426 N CASEY KEY ROADOSPREY, FLUnder contract-accepting backup offers. Gulf to Bay on North Casey Key â the perfect loc... |
3 beds | 2 baths | 1,876 sq.ft. |
$4,500,000 |
Airbnb cash on cash: -1.31%
|
280 HIDDEN BAY DRIVE #202OSPREY, FLREADY 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%
|
360 N POINT ROADOSPREY, 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%
|
819 SHADOW BAY WAYOSPREY, FLA 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%
|
Real Estate investment in Osprey, FL
There are 87 properties for sale in the city of Osprey . The median list price in Osprey is $749,000 and the average price per square foot is $289. In September 2025, the average monthly cash on cash return in Osprey is 3.00%. The average monthly rental income in Osprey is $3,428.