14844 Black Bear Rd

Nestled within the highly sought-after Caloosa neighborhood, this exceptional 3-property compound spans 5 acres of meticulously landscaped, fenced, and gated grounds. Each home, constructed with durable CBS Block, boasts single-story buildings showcasing impact-resistant glass doors and windows for comprehensive hurricane protection. Impeccably maintained, the main home with 5BR and 4Ba; and an in-law suite with a separate entry, a kitchenette and en-suite bathroom. The kitchen offers custom cabinets, quartz counters, stainless steel appliances, two ovens, and a wine cooler. Additional highlights include plantation shutters, spacious walk-in closets, a practical utility/mud room, and a screened porch for outdoor relaxation. See more remarks...Enhanced security features such as flood security lights, surveillance cameras, and a newly installed water softening system with RO add peace of mind. A separate 1200-square-foot guest house provides versatility for entertaining or accommodating extended family, complete with its own kitchenette, golf cart garage, and potential bathroom conversion. The property also boasts a detached 3-car garage, a 3-stall stable, a sizable shed, and convenient wash areas. The property further impresses with a detached clubhouse, guest house or currently being used as a "man cave" spanning over 1200 square feet, offering a kitchenette, golf cart garage, flexible living space, and volume ceilingsideal for gatherings or an additional home office. Meanwhile, the 3-car garage provides ample storage with its workbench and pull-down attic, boasting 10-foot ceilings. Outdoor enthusiasts will appreciate the three-stall barn, spacious utility shed, and designated wash area, with ample space available for the addition of a pool if desired. This exceptional compound offers a lifestyle of luxury, comfort, and endless possibilities within a prestigious neighborhood setting. Caloosa Community amenities abound in this picturesque locale, boasting over 30 miles of serene interior canals ideal for fishing and kayaking enthusiasts. Equine enthusiasts will delight in the paddocks and bridle paths perfect for trail riding. Residents enjoy convenient access to upscale shopping, top-tier golf courses, fine dining establishments, and cutting-edge medical facilities. Moreover, the community offers paved roads linking the 350 five-acre parcels, seamlessly connecting each to the internal trail system. At the heart of the community lies a sprawling 32-acre park, replete with tennis and basketball courts, a scenic heart trail, a children's playground, a cozy meeting facility, a screened picnic pavilion, and barbecue amenities for enjoyable outdoor gatherings.