Luxury homes for sale in Islamorada, Florida

This exquisite bayfront Islamorada property features a main home with four bedrooms, four full bathrooms, and two half bathrooms, along with a guest house offering two bedrooms...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Experience the perfect blend of elegance and tropical charm in this exquisite luxury home in Islamorada. This four-story residence offers breathtaking bay views from every level...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

Bask in the original elements of the Florida Keys way of life at Kids Cay. Now being offered for the very first time, this one of a kind legacy property boasts three charming...

Presented by Sarah Ewald | Ocean Sotheby's International Realty

Auction bidding open: Bidding ends 12/5. Previously Listed $5.5M. Current High Bid $2.85M. Showings By Appt. Opulent and stylish island castle; the epitome of class and luxury...

Presented by Sarah Ewald | Ocean Sotheby's International Realty

Welcome to The Islands of Islamorada Beach Club, an exquisite, gated community featuring 22 waterfront single-family residences. This stunning home epitomizes coastal living with...

Presented by Sebastian Del Negro | Ocean Sotheby's International Realty

Welcome to The Islands of Islamorada Beach Club, an exquisite, gated community featuring 22 waterfront single-family residences. This stunning home epitomizes coastal living with...

Presented by Sebastian Del Negro | Ocean Sotheby's International Realty

Welcome to The Islands of Islamorada Beach Club, an exquisite, gated community featuring 22 waterfront single-family residences. This stunning home epitomizes coastal living with...

Presented by Sebastian Del Negro | Ocean Sotheby's International Realty

Welcome to The Islands of Islamorada Beach Club, an exquisite, gated community featuring 22 waterfront single-family residences. This stunning home epitomizes coastal living with...

Presented by Sebastian Del Negro | Ocean Sotheby's International Realty

Welcome to The Islands of Islamorada Beach Club, an exquisite, gated community featuring 22 waterfront single-family residences. This stunning home epitomizes coastal living with...

Presented by Sebastian Del Negro | Ocean Sotheby's International Realty

Welcome to The Islands of Islamorada Beach Club, an exquisite, gated community featuring 22 waterfront single-family residences. This stunning home epitomizes coastal living with...

Presented by Sebastian Del Negro | Ocean Sotheby's International Realty

Transform your dreams of the Florida Keys into reality at Fantasy Harbor! Nestled in this private and serene enclave of Islamorada’s Lower Matecumbe, this concrete harbor-front...

Presented by Sarah Ewald | Ocean Sotheby's International Realty

Beach life simplicity perfectly describes this pristine three bedroom, two bath oceanfront home with pool, covered patio, and gated for privacy. Stunning beach and ocean views are...

Presented by Leslie Leopold | Ocean Sotheby's International Realty

This newly remodeled three bedroom, three bathroom home is located on upper Matecumbe in the heart of Islamorada, Florida. The home features a unique layout with one bedroom and...

Presented by James Mooney | Ocean Sotheby's International Realty

Welcome to this charming Old Florida-style cottage, an ideal weekend retreat nestled on Lower Matecumbe Key in Islamorada! This property is set on nearly half an acre, boasting an...

Presented by Kim Thaler | Ocean Sotheby's International Realty

Come home to outstanding views with 109 feet of bay frontage in Lower Matecumbe Key. This cottage-style home combines all of the elements of Florida Keys charm with captivating...

Presented by Kim Thaler | Ocean Sotheby's International Realty