Southbay Yacht & Racquet Club

It's a strong fit if you value water access and an active, amenity-rich lifestyle — the community centers on a private marina and racquet club, and eight of the ten current listings include a pool. It's a small, established neighborhood in Osprey rather than a sprawling new development, which appeals to buyers who want character and a settled feel.

Yes, this is a premium market: the median list price is $1,249,500 and eight of the ten active homes are priced above $1 million. There's real range though — listings currently run from $319,000 to $5,299,999 — so there's room for different budgets if you watch inventory closely.

Expect to pay around $520 per square foot, with a median home size of 2,803 square feet. Over the last 12 months 20 homes sold at a median of $1,082,500, which sits below the current median list price — a sign sellers and buyers are still negotiating.

It's measured and selective. The median home spends about 39.5 days on market, and sellers are getting roughly 93% of their asking price on average — so well-priced homes move while ambitious listings sit.

The median HOA runs about $219 per month, which covers the community's shared amenities. Median property taxes come in around $7,962 per year, in line with what you'd expect at these price points in Sarasota County.