Longboat Key, Florida

It's a quiet barrier island where the Gulf and Sarasota Bay bookend nearly every neighborhood, and 212 of the 287 active listings are waterfront. The pace is relaxed and residential, with distinct enclaves like Sleepy Lagoon and Long Beach that each draw a different kind of buyer. Mainland Sarasota County dining and culture are a short drive over the bridge.

Yes — the median list price is $950,000 and homes sold over the past year came in at a median of $1,097,500, with 127 active listings priced above $1M. Prices run from $39,500 for a dock slip up to $38,450,000 at the top end, so there's range, but the island skews high at an average of $843 per square foot.

Expect a median list price around $950,000 for a typical home near 1,503 square feet, though the mix matters — condos are the largest segment at 162 listings, followed by 69 single-family homes. You can browse by price to see how dock slips, villas, and Gulf-front units stack up across the range.

It favors buyers who take their time — the median days on market is 93.5 and sellers are getting about 93% of asking. With 514 homes sold in the last 12 months against 287 active listings, there's steady turnover and plenty to compare, and it's worth watching the just reduced listings for openings.

Given how condo-heavy the island is, the median HOA runs about $1,405 per month, which typically covers building and grounds upkeep in gated communities. Median property tax is around $8,534 per year, so factor both into your monthly carrying cost alongside the purchase price.