15760 Old State Road 4aUpper Sugarloaf Key, FL 33042

About this home

Spanning over 5.3 acres with more than 500 feet of pristine sandy shoreline on exclusive Sugarloaf Beach, this oceanfront compound offers a rare combination of scale, deep-water access, and legal nightly rental income just 30 minutes from Key West. Set behind private gates, the property features two existing detached single-family residences totaling 6 bedrooms and 6.5 bathrooms. The 4-bedroom main home and 2-bedroom guest house are currently operated as luxury vacation rentals backed by rare Special Vacation Rental Permits allowing lucrative short-term rentals. Designed for ultimate maritime living, the grounds center around a newly constructed 430-foot deep-water dock equipped with stainless steel pilings and a 5-foot draft capable of accommodating large yachts or charter pick-ups. Direct open-ocean access leads directly to world-class fishing and diving, with American Shoal Lighthouse located just 5 miles offshore. With Sub-Urban Residential zoning and extensive acreage, the estate presents endless possibilities—whether maintained as a generating luxury rental compound, reimagined as a grand private family sanctuary, or further developed into a flagship coastal retreat.

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