Skimmer Point Homes for Sale in Gulfport, FL

Skimmer Point is a gated waterfront subdivision in Gulfport, Pinellas County, and the largest of the single-residential neighborhoods inside the private Pasadena Yacht and Country Club, alongside Kipps Colony Estates, Fairway Bay, and Pasadena Point Estates (community guides, 2026). It sits behind a guarded gate off Pasadena Point Boulevard South.

The homes are detached single-family, not condos or townhomes, ranging from roughly three-bedroom plans near 2,000 square feet up to five and six-bedroom homes over 4,000 square feet, most with pools. About two thirds of the homes line the three-finger islands on the Boca Ciega Bay Aquatic Preserve with direct water frontage and a private boat dock; confirm dock, draft, and seawall per parcel.

There is a community homeowners association that is relatively modest and covers the gate, 24-hour guard service, and private road maintenance. Golf, the marina, tennis, the fitness center, and dining sit behind a separate, optional Pasadena Yacht and Country Club membership, so the carrying cost depends on whether a buyer wants the club. Confirm the current community HOA and any membership terms in writing.

The honest variable is water. This is Boca Ciega Bay waterfront, so the FEMA flood zone, the finished-floor elevation, the seawall, and the insurance quote drive the real cost. Gulfport was hit hard by Hurricane Helene storm surge in 2024, and the federal substantial-improvement rule now shapes what older waterfront homes can be renovated or must be elevated. Read the flood and insurance picture before the finishes.