Osprey Vacation Homes for Sale

Introducing The Grand Estate at The Oaks Bayside—a true masterpiece of refined living within one of Sarasota’s most prestigious gated communities. Surrounded by majestic oak trees and lush tropical landscaping, this extraordinary residence offers the perfect blend of elegance, comfort, and privacy.

One or more photo(s) has been virtually staged. Considered one of the finest community-owned marinas on the west coast of Florida, Southbay Yacht & Racquet Club features a seven-acre, deep-water boat basin that will accommodate kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet in length.

Located on one of the most desirable streets in The Oaks Clubside, this completely renovated pool home sits on a generous 0.71-acre lot with wide views of the third hole of the Heron Golf Course.

Beautifully remodeled in 2012, this bayfront residence combines elegance, functionality and an enviable location. The living room, kitchen and family room are great places to gather, and the split floor plan provides room for all, privacy to retreat with a good book or work from home options. The classic coastal style provides a view of the bay and intracoastal waterway from the primary bedroom.

One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club—an extraordinary residence taken fully down to the studs and reimagined as a like-new, luxury smart home. Set on a .4-acre lot in Flood Zone X (no lender-required flood insurance), this five-bedroom, 3.

**STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Little Sarasota Bay waters features 3 BEDS plus DEN/OFFICE, 3 FULL BATHS and incredible detail throughout including beautiful crown moldings, volume ceilings, hardwood floors, wainscoting, plantation shutters, LED lighting accents and MORE! NEW ROOF (2020).

Bring your clubs and come see this beautifully remodeled home in the Oaks Club (Bayside). Move in ready with all the amenities you need. This home boast all the room you need with 4 bedroom and a study/Bourbon room. Totally secluded back yard for enjoying the pool and spa with your friends and family. Also, this home has had the tile roof redone in 2012 and the A/C redone in 2022 and 2024.

**BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE ESTATE with Lush Garden Landscape** is located behind the Secure Gates of The Oaks Bayside, Country Club neighborhood.

Recently appraised for over 2 million, Seller relocating. Exquisite Executive Home in The Oaks Clubside, Step into elegance and luxury with this stunning two-story masterpiece. Perfectly situated to capture breathtaking views of the 9th Fairway on the Heron Course and a serene lake preserve, this home offers a rare combination of sophistication, comfort, and unparalleled design.

**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE.

One or more photo(s) has been virtually staged. This magnificent modern manse, with 4 bedrooms and 3.5 baths, literally has everything you could dream of to make a home complete, ALL OF IT NEW! Located in Pine Ranch, a community of single family homes with 1-5 acres of land, you will not find a more stately, spacious home, completely updated and ready for you to live out your Florida dreams.

This exquisite waterfront residence offers a dreamlike lifestyle with expansive views of the canal and bay, making it a gem in Sorrento Shores. Boaters dream, 10,000-pound lift in your backyard, 20 minutes to Venice Inlet with access to the turquoise waters of The Gulf.