$4,400,000

1571 Harbor Cay LnLongboat Key, FL 34228

  • 4 beds
  • 3.5 baths
  • 4,209 sqft
  • 0.59 acres
  • 496 days on market

About this home

Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen.
The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort.
This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast. Sellers will repaint exterior of house whatever color Buyer selects before closing, upon firm executed Contract.

Facts

Property type
Single Family Residence
Year built
1987
Stories
2
Garage spaces
2
Lot size
0.59 acres
Pool
Yes
Waterfront
Yes
Water view
Canal
Subdivision
BAY ISLES
Community
Bay Isles
County
Sarasota
CDD
0
Annual taxes
$16,980 (2024)
Flood zone
AE*
Pets
Yes
New construction
No
MLS #
A4666688

Features

Interior
Built-in Features, Ceiling Fans(s), High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Microwave, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Flooring
Brick, Ceramic Tile, Tile, Wood
Heating
Central, Electric
Cooling
Central Air
Exterior
Garden, Lighting, Outdoor Grill, Private Mailbox
Patio & porch
Covered, Deck, Patio, Rear Porch
Pool features
Auto Cleaner, Child Safety Fence, Chlorine Free, Gunite, Heated, In Ground
Parking
Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Guest, Oversized, Workshop in Garage
Construction
Concrete, Metal Frame, Stucco, Frame
Roof
Concrete, Tile
Lot
Corner Lot, Flood Insurance Required, FloodZone, Landscaped, Near Golf Course, Near Marina, Oversized Lot, Paved, Private
View
Garden, Pool, Water
Community features
Association Recreation - Owned, Buyer Approval Required, Deed Restrictions, Gated Community - Guard, Special Community Restrictions, Street Lights
Association amenities
Gated, Maintenance, Recreation Facilities, Security
HOA fee includes
Guard - 24 Hour, Escrow Reserves Fund, Management, Private Road, Recreational Facilities, Security
Utilities
Cable Connected, Natural Gas Connected, Phone Available, Public, Sewer Connected, Sprinkler Meter, Sprinkler Well, Underground Utilities, Water Connected
Water
Public
Sewer
Public Sewer
Elementary school
Southside Elementary
Middle school
Booker Middle
High school
Booker High

Location

Stellar MLS Listing courtesy of MICHAEL SAUNDERS & COMPANY. MLS # A4666688.

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Stellar MLS

Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS. Last updated: 2026-11-04 11:30 PM EST.