139 Gimpy Gulch Drive

About This Home

Yes, you can have it all! This one-of-a-kind 3.2 acre Islamorada bayfront estate offers a new boat dock, more than 250 feet of sandy wade-in bayfront shoreline, two full residences, a separate garage/media house and a move-in ready package of extras unlike any other property in the Keys. This remarkable compound captures the spirit of the Keys with a level of scale and exclusivity seldom found on the islands. Arrive through a private gate to discover a secluded retreat where every detail has been curated for relaxed coastal living. For boaters, the new boat dock offers immediate access to Florida Bay and immediate Atlantic Ocean access through nearby Snake Creek. The welcome package also includes a newer 34' Edgewater with twin 400 hp Yahamas, a pair of Waverunners and UTV tow vehicle, plus fishing rods, kayaks, paddle boards, and bicycles to enjoy everything Islamorada has to offer. The 100 ft. long resort-style pool with large spa create the centerpiece of the property, surrounded by multiple lounging areas, outdoor kitchen with covered bar, shady terraces and intimate gathering spaces. The estate's flexible layout includes two full homes--a 2/2.5 with ground level living, and a 3/3.5 tri-level--plus a 1/1.5 media house with 2-car garage, all with classic island character. Both homes offer chef kitchens with high-end appliances including SubZero and La Cornue. Not only is this estate ready for fun, it's also ready to enjoy with furniture, decor, kitchenware and even linens included! This remarkable property encompasses 2 acres of upland, 1.2 acres of baybottom, a separate buildable lot, plus valuable development rights. It is also conveniently located next to Islamorada's crown jewel Founder's Park for near instant access to seasonal festivals, sports fields, dog park, playground, tennis and pickleball courts and much more. All of these features elevate the property into a true legacy holding--ideal as a luxury residence, family compound, or private retreat.