Osprey Vacation Homes for Sale

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1216 N Casey Key Rd, Osprey, Florida 34229

Residential For Sale

PREMIER SOTHEBYS INTL REALTY
This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A.
$11,750,000
5Bedroom(s)
8Bathroom(s)
Workshop in GarageParking(s)
8,050Sqft

505 Luminary Blvd, Osprey, Florida 34229

Commercial Sale For Sale

AMERICAN PROPERTY GROUP
American Property Group of Sarasota, Inc. presents 505 Luminary Blvd, Osprey, Sarasota Property Type: Commercial Land with Existing Office Building Property Size: 10 Acres Discover this exceptional opportunity with over 900 feet of frontage on Tamiami Trail/US41 in Osprey, FL! This is one of the last substantial parcels available in Sarasota County with a Tamiami address.
$7,499,000
4,000Sqft

144 N Casey Key Rd, Osprey, Florida 34229

Residential For Sale

EXP REALTY LLC
Priced reduced! Welcome to this extraordinary waterfront estate on exclusive Casey Key, showcasing panoramic views of Little Sarasota Bay and vistas of the Gulf of Mexico. Built to the latest hurricane standards with impact-rated windows and doors, this home is a true fortress of safety and resilience. Designed for both comfort and sophistication, this 4-bedroom, 5.
$6,950,000
4Bedroom(s)
6Bathroom(s)
DrivewayParking(s)
5,397Sqft

101 Osprey Point Dr, Osprey, Florida 34229

Residential For Sale

COLDWELL BANKER REALTY
One or more photo(s) has been virtually staged. Indulge in the epitome of sophistication and timeless elegance with this magnificent luxury home with 4 bedrooms, 5 full and 1 half bath. Meticulously crafted with unparalleled attention to detail by Bo MacEwen, this residence exemplifies quality and refinement at every turn.
$5,300,000
4Bedroom(s)
6Bathroom(s)
Garage Faces SideParking(s)
5,087Sqft

1049 N Casey Key Rd, Osprey, Florida 34229

Residential For Sale

PREMIER SOTHEBYS INTL REALTY
Seize the opportunity to own a piece of paradise on the exclusive North Casey Key. This sprawling one-plus-acre estate, with 107 feet of pristine gulf frontage, a walkable sandy beach, on a private road with security offering unparalleled privacy, is your personal slice of heaven.
$4,750,000
3Bedroom(s)
3Bathroom(s)
DrivewayParking(s)
2,582Sqft

426 N Casey Key Road, Osprey, Florida 34229

Residential For Sale

PREMIER SOTHEBYS INTL REALTY
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.
$4,500,000
3Bedroom(s)
2Bathroom(s)
1,876Sqft

854 Macewen Dr, Osprey, Florida 34229

Residential For Sale

GENEROUS PROPERTY
One or more photo(s) has been virtually staged. **SELLER WILL PAY 100% OF THE MANDATORY SOCIAL MEMBERSHIP – WORTH $80,000 – IF CLOSING BY JUNE 2ND, 2025** NEWLY RENOVATED, SPACIOUS, GOLF COURSE ESTATE Boasts OVER 9,000sf and is situated on a prominent, private cul de sac lot of Over 3/4 Acres.
$4,195,000
4Bedroom(s)
6Bathroom(s)
DrivewayParking(s)
9,081Sqft

275 Lookout Point Dr, Osprey, Florida 34229

Residential For Sale

PREMIER SOTHEBYS INTL REALTY
This stunning waterfront residence in Southbay Yacht and Racquet Club is a gem on Florida’s Gulf Coast where boats are accommodated in a deep-water marina for low fees. Boasting over 135 feet of water frontage and surrounded by lush tropical landscaping and majestic Royal Palms. Its refined curb appeal sets it apart as a one-of-a-kind property.
$3,997,000
5Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
5,279Sqft

5 N Casey Key Rd, Osprey, Florida 34229

Residential For Sale

AYERS AND ASSOCIATES REAL ESTATE
PRICE IMPROVEMENT! Iconic Gulf-front Mid-Century Modern gated residence on Casey Key embodies the true essence of casual coastal living, offering an unparalleled retreat for the soul. The moment you step through the door, a magical transformation takes place. Your senses awaken as you are immediately captivated by the breathtaking Gulf views stretching out in every direction.
$3,675,000
4Bedroom(s)
4Bathroom(s)
Garage Faces SideParking(s)
2,380Sqft

135 Tina Island Dr, Osprey, Florida 34229

Residential For Sale

RE/MAX PALM REALTY OF VENICE
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.
$3,275,000
3Bedroom(s)
5Bathroom(s)
2,572Sqft

662 Fernwalk Ln, Osprey, Florida 34229

Residential For Sale

GENEROUS PROPERTY
**FANTASTIC, FULLY RENOVATED ESTATE with LAKE / GARDEN VIEW is situated on a SERENE, INTERIOR, CUL-DE-SAC lot with NO FLOOD concern (Zone “X”) behind the Secure Gates of the highly sought after Bayside neighborhood within The Oaks Country Club community, just steps from Little Sarasota Bay.
$2,995,000
4Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
4,359Sqft

236 Saint James Park, Osprey, Florida 34229

Residential For Sale

MICHAEL SAUNDERS & COMPANY
Tucked away in a quiet cul-de-sac on a double lot beneath majestic oaks, this almost 5,000 sq ft, timeless 2-story home blends sophistication with modern comfort. Situated on the first hole of Heron Golf Course, the home features soaring 11-ft ceilings, marble floors, and crystal chandeliers.
$2,900,000
6Bedroom(s)
7Bathroom(s)
Garage Faces SideParking(s)
6,246Sqft
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