Clearwater Vacation Homes for Sale

Under contract-accepting backup offers. Timeless architecture meets refined modern living in this extraordinary Georgian-style Luxury pool home, which is gracefully positioned along the 15th fairway of the sought after Feather Sound Country Club.

TWO LEVEL PENTHOUSE with separate MOTHER IN LAW SUITE. This South Facing Penthosue features: Two Separate Master Suites, Three Spacious Bedrooms, 3 1/2 Baths, OFFICE OR 4TH BEDROOM, LOFT (room for sleeper sofa) and Laundry ROOM. World Famous Sand Key Club located in CLEARWATER BEACH, Home of the SUGAR SANDS. LOCATION, LOCATION, LOCATION.

Developers, Investors or just DIY home-owner end users. Huge Opportunity on this private wonderfully located serene property with some waterfront in the heart of Clearwater on up to 2 acres ...that is a full remodel.

Under contract-accepting backup offers. Tucked away on one of Clearwater’s most exclusive and historic streets in the coveted Harbor Oaks neighborhood, this newer construction masterpiece—built in 2022—combines Italianate-inspired architecture with modern sophistication. A timeless treasure, the residence features 5 bedrooms and 3.

Welcome to your private compound in a prime Clearwater/Dunedin location just one block from the Gulf of Mexico with peek-a-boo water views from the top deck. This sprawling 6-bedroom, 6-bath estate is a rare gem designed for luxurious living and effortless entertaining. The main home offers four spacious bedrooms and four baths.

Live in Resort-Style Luxury While Earning Passive Income! Welcome to paradise in the heart of Clearwater — just 10 minutes from the world-renowned Clearwater Beach, within walking distance to Clearwater Country Club, and in an A-RATED school district.

Welcome to this stunning 2-bedroom, 2-bathroom condo, perfectly located close to Downtown Dunedin, offering breathtaking views of the Intracoastal and Stevensons Creek. This property provides an exceptional blend of luxury and convenience, designed to complement a vibrant lifestyle by the water.

WATERFRONT OPPORTUNITY! This remarkable 3,118 sq. ft. Clearwater waterfront home was a true showpiece—offering luxurious indoor/outdoor living, tropical landscaping, and resort-style amenities. Unfortunately, the home sustained flooding due to Hurricanes Helene and Milton and is now in need of repair and restoration.

Under contract-accepting backup offers. 50k price adjustment! If you’re looking for a home with space and elegance that has been well cared for, look no further! This stunning home, built in 2006, features 6 bedrooms, 6 bathrooms, a large bonus room, a 3-car tandem garage, and a pool. Two bedrooms are primary suites, one upstairs and one downstairs.

One or more photo(s) has been virtually staged. … If these walls could talk, they’d tell the story of an owner-engineer / builder who carefully crafted and over-engineered this home over the past 35 years, creating a true Self-Contained, family, waterfront resort-estate … with Airbnb another Potential use ….

Beautiful three bedroom, three and a half bathroom condo with high ceilings and south westerly views that are as peaceful as they are jaw dropping. Rarely does such a unit come available so don't miss your chance to see this beauty.

Welcome to Cabana Club – the jewel of Sand Key’s South Shore! Cabana Club, with its unique charm allows inhabitants to enjoy the Beach just steps away, a game of checkers on the expansive brick-paved porch, or sweat to the oldies in the beach-facing gym! You can also enjoy basketball, tennis or pickleball, and a geothermal-heated pool! Upon entering this two bedroom, 2 bath + a den beauty, you