Longboat Key: Refined, Quiet, and Right on the Gulf

Longboat Key stretches twelve miles south from Anna Maria Island, a slender barrier island between Sarasota Bay and the Gulf. It carries a more resort-like, residential feel, with manicured grounds, Gulf-front condominiums, and waterfront estate homes.

Longboat Key and Anna Maria Island: how they compare

The two barrier islands sit end to end — Longboat Key begins where Anna Maria Island leaves off, separated only by Longboat Pass — but they read quite differently. Anna Maria keeps a village scale: cottages, low buildings, three small towns, and a walk-and-trolley pace. Longboat Key is the more resort-residential address, with Gulf-front condominium communities, golf and tennis, and estate homes along the bay. Buyers regularly tour both in a single day and decide on character rather than distance.

The setting

Powdery Gulf beaches run the length of the key, while the bay side offers deep-water docks and boating access. Golf and tennis are woven into island life, and several communities include marinas, club amenities, and private beach access.

Dining and culture nearby

At the south end, St. Armands Circle is a short hop away — an open-air ring of restaurants, boutiques, and galleries — with downtown Sarasota and its arts scene just beyond. The result is a quiet island address with city culture minutes away.

The housing market

Longboat Key is largely a second-home and seasonal market. Inventory leans toward Gulf-front and bay-front condominiums, canal and open-water homes, and a smaller number of estate properties. Prices reflect the location and water frontage, and well-positioned listings can move quickly.

Considering Longboat Key? Reach out and I'll help you find the right fit.