West of the Trail
I grew up partly in Oyster Bay, in the area known as "West of the Trail", close to the Siesta Drive (North Bridge) bridge to Siesta Key. It's a beautiful area with a variety of home sizes and styles, and an abundance of mature landscaping. It has fantastic proximity to the beach, the Field Club, downtown, and the Bayfront, has fantastic schools, and great access to your typical amenities (you won't need to drive 20 minutes just to pick up a gallon of milk). Some homes here even have waterfront views--either lake or on the Intracoastal.