One Property. Many Possibilities. Welcome to an unparalleled legacy estate spanning 13,474 sq/ft under air (over 21,000 sq/ft total) on a secluded 1.17-acre parcel in the prestigious Pine Ridge Estates. With 12 bedrooms and 9½ baths, this architectural masterpiece delivers privacy, style and sophistication for multigenerational living, grand-scale entertaining and bespoke work, wellness, or creative zones. Grand Arrival & Formal Entertaining Enter through wrought iron double doors into a soaring foyer flanked by a luminous living salon and a formal dining pavilion beneath a sculptural chandelier. Hand troweled walls, custom millwork and gallery style lighting evoke timeless craftsmanship and hospitality. Culinary Heart & Casual Gathering The chef’s domain boasts professional grade Viking appliances, prep island, expansive butler’s pantry complete with wine and bar station. A breakfast nook beneath a tray ceiling opens seamlessly to the courtyard. Resort Style Outdoor Living The central courtyard reveals an impressive free form lagoon pool, waterfall grotto and integrated spa. An outdoor kitchen with built in grill, stone topped bar seating and alfresco dining invites endless possibilities for lounging and entertaining under the Florida sun. A pool bath, cedar lined sauna and separate steam shower complete this private resort experience. Resting Places A serene primary suite features bay window seating, dual walk-in closets and a spa bath with a deep soaking tub and lux shower with multiple shower heads. This residence was designed for large scale hosting and quiet moments alike—with over eleven additional beautifully styled private zones for sleeping, lounging, or working in peace. Cinema, Service & Convenience This estate also boasts a state-of-the-art home theater, multi-level posh seating, cinematic sound system creates the ultimate cinematic experience in the comfort of your own home. A four-car garage, mudroom, dual laundry stations and discreet service corridor maintain impeccable flow for daily living or staffed events. A DESIRABLE ADDRESS Consistently ranked #1 Best Place to Live and #1 Best Place to Retire by U.S. News & World Report, Naples is celebrated for its world class white sand beaches and championship golf—aptly nicknamed the “Golf Capital of the World.” Waterside Shops and Mercato offer haute couture retail, while award winning restaurants and curated arts venues enrich daily life. Private beach clubs, pro level sporting events and an elevated social scene ensure every desire is fulfilled. Moments from beaches, cultural attractions, and world-renowned golf, this is a rare legacy estate for those whose vision of home embraces style, scale, and the power to bring people together. 185 Tupelo Road represents unparalleled value—offering the lowest price per square foot of any home available in Pine Ridge, making it a compelling investment for discerning buyers. One home. Endless opportunity.