A Sarasota Landmark. For the first time in over 50 years, this extraordinary bayfront estate is available. Nestled beneath a canopy of hundred-year-old oaks, this 2.1-acre property has remained in the same family since the 1970s—making it a true Sarasota landmark. With two custom-built Mid-Century homes and unmatched views of Sarasota Bay, downtown, Siesta Key, Bird Key, and the Ringling Bridge, the property embodies the rare combination of history, privacy, and natural beauty. Each home, rich with character and never subject to water intrusion, offers limitless potential to be refurbished, reimagined, or enjoyed as-is. Adding to its rarity, the property includes an additional lot—together offering the unique possibility of dividing into three buildable bayfront parcels. Whether preserved as a private family compound or envisioned as multiple new estates, this is one of Sarasota’s most coveted and irreplaceable waterfront settings. This includes both 3348 Old Oak Drive A4632727 and 3350 Old Oak Drive A4632749.