Rarely does an opportunity like this come to market, offering a piece of Old Florida on 2.1 lush acres and boasting breathtaking views of Sarasota Bay, Siesta Key, Bird Key, Ringling Bridge, and downtown Sarasota, this magnificent family compound features two custom-built Mid Century homes and a vacant lot, offering limitless possibilities. Designed to take advantage of the amazing views, the first structure is 3,263 square feet with 3 bedrooms and 4 bathrooms. Throughout, you'll find cypress walls and an abundance of windows and glass sliders framing stunning views of mature oak trees and the beautiful blue waters of the bay beyond. The spacious great room features a wood-burning fireplace and sliders leading to an outdoor terrace perfect for gathering with friends and entertaining. The updated kitchen features an island, white cabinetry, quartz countertops, 2 large pantries, and a bar. Formal dining room is graced by two walls of glass sliders overlooking outdoor greenery. A walk through the ample-sized den leads to 2 en-suite bedrooms, with the third bedroom located at the opposite end of the home for privacy. The large office with high ceilings and 2 walls of glass sliders could also be used as a bedroom. The second home is a 3,669-square foot 2-story design masterpiece featuring cypress inside and out and an indoor heated swimming pool. High ceilings and open spaces offer comfort and airiness, while the walls of glass sliders and windows fill the interior with natural lighting while showcasing gorgeous views of the lush landscaping and bay waters. The expansive great room features floor-to-ceiling sliders and a wood-burning fireplace, creating a warm and inviting space, while the open kitchen with an island is perfect for creating culinary delights and entertaining. Also on the first level is an additional living space and a large flex room with sliders leading to a screened outdoor patio. This bonus room is ideal for a home gym, playroom, or art studio. Adjacent to this room you'll find a large heated indoor pool perfect for swimming laps day or night or just relaxing in while admiring the scenery. Upstairs, is a laundry room, 2 comfortable guest rooms, and a generous primary suite with a fireplace, large windows, and a well-appointed spa-like bath with a walk-in shower and soaking tub. Each of these unique homes offers amazing sunsets and one-of-a-kind views of the beautiful Sarasota Bay from nearly every room. Little bay front dock allows for launching of kayak, paddle boards or small sailing vessels Don't miss this chance to own this highly desirable property that offers endless opportunities and is being brought to market for the first time. Both parcels being sold as a package or sold separately. 3348 Old Oak Drive MLS# A463229, 3350 Old Oak Drive MLS# A4632289.