Osprey Vacation Homes for Sale

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.

Newly Remodeled Gulf-Front Mediterranean Villa on Casey Key Framed by the pristine natural beauty of North Casey Key, this Spanish Mediterranean beachfront estate is perfectly positioned along one of Florida’s most exclusive barrier islands — an unspoiled, eight-mile stretch of tropical coastline.

A striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless residence blends architectural elegance with waterfront living. Offering private access to the Intracoastal with a 100-foot dock (built in 2019), dual 12,000-pound lifts, water, and electric, this property is an ideal destination for boating enthusiasts. Offered fully furnished upon request.

New Seawall / Waterside deck, New Automated Gate, Lanai Automated Screens Commanding over half an acre with 116 feet of pristine frontage on Little Sarasota Bay, this brand-new custom estate captures the essence of coastal luxury. From the moment you arrive, you are greeted by sweeping water views and spectacular Casey Key sunsets, setting the stage for an extraordinary lifestyle.

Premier Intracoastal Estate in Osprey 4 Bedrooms | 6 Bathrooms | 6,308 Sq. Ft. | 2 Waterfront Acres A rare opportunity to own two acres of private waterfront property in Sarasota, 730 Sarabay is a convergence of residential luxury and unparalleled waterfront living. The two-story home sits at the end of a long drive behind a gated entrance and tranquil pond.

A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one-of-a-kind home spans more than 5,000 square feet, all cleverly positioned on nearly an acre with 150 feet of lakefront.

Under contract-accepting backup offers. 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.

Under contract-accepting backup offers.

Nestled within the exclusive gated community of the Oaks Club in Osprey, Florida. This singular estate represents a masterful confluence of architectural refinement and modern luxury, encompassing nearly 7000 ft.² of conditioned living space, the residence has undergone an extraordinary transformation – reflecting an investment exceeding $1.

One or more photo(s) has been virtually staged. Set on a private cul-de-sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home’s light-filled, open design and thoughtful updates make an immediate impression.

If your dream is to create a place where generations can gather, relax, and make lasting memories, this Casey Key estate is ready to welcome you home. Set on 0.68 acres with 131 feet of Sarasota Bay frontage, this 4 bed 4.5 bath retreat offers room to spread out, unwind, and connect indoors and out.

Retreat to paradise in this stunning waterfront home, built new in 2011, in highly sought-after Sorrento Shores, Osprey. Perfectly situated on 210 feet of wide canal frontage, this residence offers deep water access with no bridges to the bay—a dream for boaters. Nearly every room provides breathtaking views of the water and swaying palms.