For sale Home

Listed May 16, 2026

$439,999 Est. $2,910/mo

4237 Headsail Drive

  • 3

    Beds

  • 3

    Baths

  • 1,594

    Sq ft

The story

  • Waterfront

Unlock an incredible opportunity to own your waterfront dream home in the highly sought-after Gulf Harbors community. This 3-bedroom, 2-bath block home sits on a double lot and offers Florida charm, water access, and coastal lifestyle that make this neighborhood so desirable. Enjoy a large open kitchen, a bright and airy layout, and a Florida room overlooking the water, perfect for morning coffee or sunset views. The home features a side-entry two-car garage, plus a breezeway with additional storage, giving you plenty of room for tools, toys, and gear. Boaters will love the floating dock, ready for you to tie up your boat and or cut ties and head straight to the big water in minutes. Whether you’re fishing, cruising, or island-hopping, this location delivers unmatched convenience. Gulf Harbors offers an exceptional coastal lifestyle with optional access to its private beach, known for its pristine sand, turquoise water, and unforgettable sunsets. This is your chance to secure a true waterfront gem and make it your own.

Facts & features

Home type

Home

Year built

1969

Floors

1

Price per sq ft

$276

HOA

$125 / annually

Parking

2-car garage

Included features

  • Cooling

    Central Air

  • Heating

    Central, Electric

  • Appliances

    Dishwasher, Range, Refrigerator

  • Roof

    Shingle

  • Lot Information

    In County, Landscaped, Level, Paved

  • Exterior

    Lighting

  • Water Source

    Public

  • Sewer

    Public Sewer

  • View

    Water

Mortgage calculator

Estimated monthly payment

$2,910 /mo

7% rate · 30-yr fixed · 20% down

  • Principal & interest $2,342
  • Property tax $440
  • Insurance $128

Includes principal, interest, taxes & insurance.

Your Property Journey

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Listing Broker

KELLER WILLIAMS REALTY SMART

Broker Name

KELLER WILLIAMS REALTY SMART

Agent

Chad Karr