Osprey Vacation Homes for Sale

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1544 CASEY KEY ROAD, OSPREY, Florida 34229

Single Family Residence For Sale

Along the beaches of Casey Key, a private gated road leads to the exclusive northern end of this coveted barrier island. Sited on nearly 2.5 acres and 150 feet of private beach front, lies a spectacular estate home that has been shared and enjoyed by one family for generations. Designed by renowned architect Timothy Siebert, the property was thoughtfully planned as a gathering place.
$10,500,000
6Bedroom(s)
7Bathroom(s)
10,137Sqft
PREMIER SOTHEBYS INTL REALTY

426 CASEY KEY ROAD, OSPREY, Florida 34229

Single Family Residence For Sale

Gulf to Bay on North Casey Key – the perfect location! Panoramic views of Little Sarasota Bay to the east and a beachfront lot on the west. Original cypress tongue and groove ceilings and beautiful oak floors add warmth and nostalgia throughout the home. A nicely updated kitchen overlooks the pool and bay.
$4,900,000
3Bedroom(s)
2Bathroom(s)
3,114Sqft
PREMIER SOTHEBYS INTL REALTY

425 TITIAN DRIVE, OSPREY, Florida 34229

Single Family Residence For Sale

Luxury waterfront gated estate directly on the Intracoastal waterway with 2 boat lifts and one covered for weather protection, has sailboatrnwater for larger boats dockside, 2 story with Master suites on both levels, 2nd floor has large viewing deck/workout room/office and smallrnkitchen.
$4,499,000
5Bedroom(s)
5Bathroom(s)
8,320Sqft
KELLER WILLIAMS REALTY GOLD

5 CASEY KEY ROAD, OSPREY, Florida 34229

Single Family Residence For Sale

Welcome to your very own Gulf front beach home located on one of the most captivating, serene and exclusive barrier islands on Florida's west coast. This custom 4 bedroom 3.5 bathroom mid-century modern luxury property is directly on the Gulf with absolutely stunning unobstructed views and your very own private beach.
$4,400,000
4Bedroom(s)
3Bathroom(s)
3,515Sqft
CHARLES RUTENBERG REALTY INC

135 TINA ISLAND DRIVE, OSPREY, Florida 34229

Single Family Residence For Sale

If you are ready to retreat to paradise, look no more. This home is amazing. Located in a very desirable area in Sorrento Shores, Osprey is on a 200-foot, wide canal frontage. You can enjoy the scenic water and exotic palms through almost every window. The main area, the living area, was built and completed in 2011, and it is beautifully situated on the second floor.
$3,450,000
3Bedroom(s)
4Bathroom(s)
6,257Sqft
RE/MAX PALM REALTY OF VENICE

140 CASEY KEY ROAD, OSPREY, Florida 34229

Single Family Residence For Sale

DROP ANCHOR and stay forever in this 3 bedroom, 3.5 bath, intracoastal waterway home tucked away just enough to feel like you have your very own private oasis. You have deeded boat access with your own assigned boat slip where you may catch dolphins playing in the water before you take out your kayaks, jet skis, or the boat.
$3,400,000
3Bedroom(s)
3Bathroom(s)
2,773Sqft
LPT REALTY

324 KENSEY LANE, OSPREY, Florida 34229

Single Family Residence For Sale

Rare opportunity to own an exceptional waterfront property and tropical oasis on .57 acre lot on a wide portion of Little Sarasota Bay. Bayview Cottage is the original Florida coastal cottage lifestyle which showcases magnificent water views and spectacular sunsets. This gated waterfront gem has 3 bedrooms, 3 bathrooms, includes bonus room, office, and laundry closet.
$2,174,000
3Bedroom(s)
3Bathroom(s)
3,063Sqft
SARASOTA COAST REALTY INC

14 BLAKE WAY, OSPREY, Florida 34229

Single Family Residence For Sale

Welcome to 14 Blake Way, nestled within the exclusive community of Osprey Woods. This exquisite 3-bedroom, 3-bathroom (+ office) home, constructed in 2015, stands as a testament to modern elegance and comfort. With only 7 homes in this gated neighborhood, privacy and tranquility are paramount.
$1,995,000
3Bedroom(s)
3Bathroom(s)
5,464Sqft
MICHAEL SAUNDERS & COMPANY

3961 WAYPOINT AVENUE, OSPREY, Florida 34229

Single Family Residence For Sale

Escape to your coastal oasis nestled within the exclusive enclave of Bayside, where luxury living meets the tranquility of Little Sarasota Bay. This newly built 3-bedroom, 3-bathroom residence, boasting an additional den/office, is a testament to perfection with upgrades at every corner.
$1,159,000
3Bedroom(s)
3Bathroom(s)
3,408Sqft
RE/MAX ALLIANCE GROUP

434 SHORE DRIVE, OSPREY, Florida 34229

Single Family Residence For Sale

One or more photo(s) has been virtually staged. Experience the beauty of waterfront living in the desirable neighborhood of Sorrento Shores, tucked away west of the Trail. This home is a dream for boaters, with no fixed bridges and easy access to the Gulf of Mexico.
$1,099,900
3Bedroom(s)
3Bathroom(s)
4,350Sqft
ENGEL + VOELKERS SARASOTA

236 HIDDEN BAY DRIVE Unit#504, OSPREY, Florida 34229

Condominium For Sale

Welcome to Hidden Bay. This stunning 3bd/ 3br corner unit condo offers unimpeded views of Casey Key and Little Sarasota Bay from many rooms. The large foyer welcomes guests into the home and boasts a completely remodeled 5th floor unit featuring high-end finishes throughout, including bamboo flooring, quartz countertops, solid wood cabinetry, and an induction cooktop.
$1,050,000
3Bedroom(s)
3Bathroom(s)
2,394Sqft
RE/MAX ALLIANCE GROUP

3929 WAYPOINT AVENUE, OSPREY, Florida 34229

Single Family Residence For Sale

You've found your new Florida Home at Bayside- Maintenance- Free, Gated, Waterfront community with only 49 homes on the Sarasota Bay. The beautiful heated pool home features three bedrooms and three baths as well a private office space. Master bedroom offers an en suite bathroom with dual vanities, walk in shower, oversized walk in closet with built ins.
$1,050,000
3Bedroom(s)
3Bathroom(s)
3,175Sqft
RE/MAX ALLIANCE GROUP
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