Longboat Key, Florida

If you want to live on the water, it's hard to beat — 269 of the 363 active listings are waterfront, and communities like Sleepy Lagoon and Country Club Shores put boating and beaches at your doorstep. It's a quieter, residential barrier island rather than a nightlife hub, which suits buyers looking for calm coastal living.

Yes — it's one of the pricier stretches of the Gulf coast, with a median list price of $960,000 and 167 of the active listings priced above $1 million. Prices run from the high five figures for smaller condos all the way up to $38.45 million, so there's genuine range if you browse by price.

The median list price is $960,000, and homes average $844 per square foot against a median size of 1,513 square feet. Condominiums make up the bulk of inventory, while single-family homes and larger waterfront properties push toward the top of the range.

There are 363 active listings and homes are taking a median 95 days to sell, which signals a market where buyers have negotiating leverage. Keep an eye on the just reduced listings, since longer marketing times often lead to price adjustments.

Because condos dominate here, HOA costs matter — the median HOA runs about $1,406 per month, covering the amenities and building upkeep common in coastal communities. The median annual property tax is $8,653, so factor both into your monthly budget when comparing a condo to a single-family home.