74049 Overseas Hwy Upper Sugarloaf Key, FL 33036

Welcome to Casa Matecumbe, an extraordinary oceanfront sanctuary located at 74049 Overseas Highway in the prestigious Village of Islamorada. This iconic property represents one of the rarest opportunities in the Upper Keys: a private, gated, resort-style compound offering expansive open-water views, unmatched privacy, and the timeless charm of classic Florida Keys architecture. Set on a generous parcel with a sandy beach, and direct ocean access, Casa Matecumbe delivers the ultimate coastal lifestyle--one defined by serenity, natural beauty, and the freedom to enjoy the water at a moment's notice. The gated entrance supplies a perfect level of privacy. The approach sets the tone for the entire experience: peaceful, secluded, and authentically 'Old Florida,' yet elevated with the sophistication expected in a luxury Keys residence. Whether used as a full-time home, a seasonal retreat, or a legacy property to be enjoyed for generations, Casa Matecumbe offers a rare combination of location, land, and lifestyle that is nearly impossible to replicate. The main residence is thoughtfully positioned to maximize panoramic ocean views from nearly every room. Expansive windows and glass doors frame the turquoise water, inviting natural light to fill the interior spaces throughout the day. Upstairs there are 3 bedrooms and 2 baths as well as a gorgeous kitchen an open concept with dining under air conditioning or al fresco, Downstairs includes a large en-suite bedroom with water views as well as an additional kitchen and dining living area. Lower-Level Finished area of 1,065 is included in square footage. Both levels offer a breezy indoor-outdoor living--with modern comforts including updated finishes, impact windows, and spacious living areas. This 4-bedroom House is the perfect vacation home for larger families wishing to enjoy the pool, the beach and the ocean in a private setting.