8585 MIDNIGHT PASS ROAD A private legacy estate on Siesta Key. Behind a private gate and walled perimeter on one of Siesta Key’s largest residential parcels, this majestic waterfront estate offers a rare opportunity to own a generational property of striking character, scale, and serenity. Set on 1.6 lushly landscaped acres with 132 feet of direct frontage on Little Sarasota Bay, the residence is introduced by a long, winding paver drive, framed by mature oaks and a tranquil pond with fountain — a cinematic approach that sets the tone for what’s to come. Designed for those who value privacy without compromise, the estate offers a seamless blend of timeless architecture, expansive outdoor living, and exclusive access to the bay and beach. In addition to its commanding bayfront presence, the property includes deeded private Gulf beach access just across the way — an extremely rare amenity for bayfront living on Siesta Key. Custom-built in 2002 and surrounded by multi-level terraces, the 5, 727-square-foot residence captures sweeping eastern views of the Intracoastal Waterway from nearly every principal room. A dramatic two-story foyer opens to the grand living room, where 20-foot ceilings, triple sets of French doors, and a carved gas fireplace frame the water beyond. The formal dining room features a crystal chandelier, intricate ceiling medallion, and custom wainscoting — ideal for elegant gatherings. The newly updated kitchen features 42-inch cabinetry, Carrara marble countertops, a professional Wolf gas range, Sub-Zero refrigerator, center island, and an oversized walk-in pantry. It opens naturally to the breakfast and family rooms, all with direct access to the terrace and bayfront views. The richly paneled cherry library offers a handsome retreat, complete with fireplace, built-ins, and a tin ceiling, along with terrace access. The second-floor primary suite is a luxurious escape with a private bayfront terrace, 13- foot ceilings, sitting area with fireplace, dual custom walk-in closets, and a marble-clad bath with soaking tub, dual vanities, and walk-in shower. Three additional en-suite bedrooms — including one on the main level — provide comfortable accommodations for guests or multi-generational living. A heated saltwater infinity-edge pool with spillover spa anchors the outdoor living spaces, enhanced by tropical landscaping, landscape lighting, and a covered patio ideal for alfresco dining. Car collectors will appreciate the garage space for 10-plus vehicles beneath the main living level, with dual side entry, elevator access and climate-controlled storage. Additional features include a greenhouse, whole-house fire sprinkler system, natural gas, hurricane shutters and impact screens, and irrigation via private well. Just minutes from Siesta Key Village and downtown Sarasota, this estate offers an unmatched combination of privacy, beauty and legacy potential in one of Florida’s desired coastal communities.