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4237 HEADSAIL DRIVE

House For Sale
$539,000

BTC: 8.98333333

ETH: 308.70561283

18 days
Waterfront
3 bds
2 ba
1,594 sqft

Overview

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.

Location

Details

Type:
Residential
Parking:
Garage Faces Side / Golf Cart Parking
Year Built:
1969
Lot:
0.17 Acres
Heating:
Central / Electric
Price/sqft:
$338
Cooling:
Central Air
HOA:
$125

Valuation

Our model vs. what's actually selling nearby.
Estimate
$315,000
$198K – $540K
Confidence Low
List vs. estimate
$224K above estimate
List $539,000 · +71.1%
Our model says this listing is priced above recent comparable activity. Room to negotiate.
Price per sq ft
$338
+53.3% vs. city median $220
Based on
37 MLS comparables
Median of recent comparable listings. Sold comps use closing price, active listings use list price.

Highlights

Annual tax
$5,203
2025
HOA
$125/yr
View
Water
Waterfront
Canal - Saltwater
Garage
2 car garage
Pets
Allowed
All facts and features
  • Flooring

    • Other

    Heating

    • Central

    • Electric

    Cooling

    • Central Air

    Appliances

    • Dishwasher

    • Range

    • Refrigerator

    Other interior features

    • Ceiling Fan(s)

    • Kitchen/Family Room Combo

    • Solid Surface Counters

    • Solid Wood Cabinets

    • Split Bedroom

    • Stone Counters

    • Thermostat

    • Walk-In Closet(s)

    • Window Treatments

    Bedrooms and bathrooms

    • Bedrooms: 3

    • Bathrooms: 1

    • Full bathrooms: 2

  • Parking

    • Garage Faces Side

    • Golf Cart Parking

    Property

    • Levels: One

    • Exterior Features: Lighting / Other

    Lot

    • Lot: 0.17 Acres

    Other Property Information

    • Parcel Number: 162607008.0010.00055.0

    • Zoning: R4

  • Type and style

    • Property Type: Residential

    • Property Sub Type: Single Family Residence

  • Utility

    • BB/HS Internet Available

    • Cable Available

    • Cable Connected

    • Electricity Available

    • Electricity Connected

    Green energy

    • Insulation

  • Other financial information

    • HOA: $125

    • HOA Frequency: Annually

    • Annual tax amount: $5,203

  • Source details

    • MLS ID: L4961684

    Other facts

    • Construction Materials: Block / Stucco

    • Foundation Details: Slab

    • Laundry Features: Inside / Laundry Room

    • Lot Features: In County / Landscaped / Level

    • Patio And Porch Features: Covered / Enclosed / Front Porch / Rear Porch

    • Direction Faces: West

    • Other Structures: Other

    • Architectural Style: Florida

    • Waterfront: Yes

    • Garage Spaces: 2

    • Attached Garage: Yes

    • Garage: Yes

    • Living Area: 1594

    • Water Source: Public

    • Subdivision Name: FLOR A MAR

Private inquiry
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The multiple listing information is provided by the Stellar MLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are ©2026-present Stellar MLS. All Rights Reserved. The information provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Listing courtesy of: KELLER WILLIAMS REALTY SMART