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.
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.
Property Details
Price:
$4,550,000
MLS #:
A4666688
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
BAY ISLES
Neighborhood:
34228longboatkey
Listed Date:
Jan 22, 2026
Finished Sq Ft:
4,209
Total Sq Ft:
5,387
Lot Size:
25,711 sqft / 0.59 acres (approx)
Year Built:
1987
See this Listing
Schools
Elementary School:
Southside Elementary
Middle School:
Booker Middle
High School:
Booker High
Interior
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Microwave, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Brick/Stone, Ceramic Tile, Tile, Hardwood
Heating
Central, Electric
Interior Features
Built-in Features, Ceiling Fan(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
Laundry Features
Electric Dryer Hookup, Inside, Washer Hookup
Levels
Two
Exterior
Architectural Style
Contemporary, Elevated
Association Amenities
Gated, Maintenance, Recreation Facilities, Security
Attached Garage YN
1
Community Features
Bay/Harbor Front, Canal Front, Gulf/Ocean Front, Intracoastal Waterway, Water Access, Waterfront, Association Recreation – Owned, Buyer Approval Required, Deed Restrictions, Gated Community – Guard, Special Community Restrictions
Construction Materials
Concrete, Metal Frame, Stucco, Wood Frame
Covered Spaces
2
Direction Faces
North
Exterior Features
Garden, Irrigation System, Lighting, Outdoor Grill, Private Mailbox, Sliding Doors
Fencing
Other
Garage Spaces
2
Lot Features
Corner Lot, Flood Insurance Required, FloodZone, Landscaped, Near Golf Course, Near Marina, Oversized Lot
Open Parking YN
1
Parking Features
Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Door Opener, Guest, Oversized, Workshop in Garage
Patio And Porch Features
Covered, Deck, Patio, Rear Porch
Roof
Concrete, Tile
Security Features
Fire Alarm, Gated Community, Security System, Security System Owned, Smoke Detector(s)
View
Garden, Pool, Water
Waterfront Features
Bay/Harbor Front, Canal Front, Gulf/Ocean Front, Waterfront, Canal – Saltwater
Window Features
Insulated Windows, Shutters, Storm Window(s), Window Treatments, Wood Frames
Financial
HOA Fee Frequency
Annually
HOA Includes
24-Hour Guard, Escrow Reserves Fund, Manager, Private Road, Recreational Facilities, Security
HOA Name
Ken Kandefer
HOA Phone
941-921-3221
Tax Year
2024
Taxes
$16,980
Map
Community
- Address1571 HARBOR CAY LANE LONGBOAT KEY FL
- SubdivisionBAY ISLES
- CityLONGBOAT KEY
- CountySarasota
- Zip Code34228
Subdivisions in LONGBOAT KEY
- 7591_BEACHPLACE_III
- 7981 – LONGBOAT KEY MOORINGS
- 8177 – LONGBOAT KEY MOORINGS MARINA 2
- ACREAG0001
- AQUARIUS CLUB
- ARBOMAR
- ARBOMAR APTS
- ARIA LONGBOAT KEY
- AVIGNON VILLAS
- BAILEY-DOBSON
- BAY HARBOUR APTS
- BAY ISLES
- BAYOU HAMMOCK
- BAYPORT
- BAYPORT BCH & TEN PH A
- BAYPORT BCH & TEN PH B
- BAYPORT BCH & TEN PH C
- BAYPORT BCH & TEN PH D
- BAYPORT BCH & TEN PH E
- BAYPORT BCH & TEN PH F
- BAYPORT BEACH & TENNIS CLUB PH D
- BAYVIEW ESTATES
- BEACH HARBOR CLUB
- BEACHES OF LONGBOAT KEY PH-1
- BEACHPLACE I
- BEACHPLACE II
- BEACHPLACE III
- BOATHOUSE ON LONGBOAT
- BONAIRE AT LONGBOAT KEY
- BUTTONWOOD COVE
- BUTTONWOOD HARBOR
- CEDARS EAST SEC 1
- CEDARS EAST SEC 2
- CEDARS EAST SEC 3
- CHARLIES
- CLUB LONGBOAT BEACH & TENNIS
- COLLIER WALKER
- CONDOMINIUM RESIDENCES AT LONGBOAT KEY
- CONRAD BEACH
- COQUINA BEACH
- COREYS LANDING
- COUNTRY CLUB SHORES
- COUNTRY CLUB SHORES IV
- COUNTRY CLUB SHORES SEC 02
- COUNTRY CLUB SHORES SEC 03
- COUNTRY CLUB SHORES SEC 2
- COUNTY CLUB SHORES SEC I
- DOCK ON THE BAY SEC 1
- DREAM ISLAND
- EMERALD HARBOR
- EN PROVENCE
- FAIRWAY BAY
- FAIRWAY BAY 1
- FAIRWAY BAY 2 PH 1
- FAIRWAY BAY 3
- FRACTIONAL SUB
- GRAND BAY 1
- GRAND BAY 2
- GRAND BAY 3
- GRAND BAY 4
- GRAND BAY 6
- GULFSHORE OF LONGBOAT KEY
- HARBOR OAKS PH I & II
- HARBOUR COURT
- HARBOUR LINKS
- HARBOUR OAKS
- HARBOUR OAKS 2
- HARBOUR OAKS PH I & II
- HARBOUR VILLA CLUB AT THE BUCCANEER
- HARRIS BAYOU
- HIDEAWAY BAY SUB
- HOOTON
- INFINITY ON LONGBOAT KEY
- INN ON THE BEACH
- INN ON THE BEACH PH I
- INN ON THE BEACH PH II
- INN ON THE BEACH PH III
- ISLANDER CLUB OF LONGBOAT
- ISLANDS WEST
- L AMBIANCE
- L AMBIANCE 1
- L AMBIANCE AT LONGBOAT KEY CLUB PH 02
- LAGUNA YACHT VILLAGE
- LAGUNA YACHT VILLAGE A CONDO
- LONGBEACH
- LONGBEACH ON LONGBOAT KEY
- LONGBEACH REV OF R P JORDANS SUB
- LONGBOAT ARMS
- LONGBOAT HARBOUR
- LONGBOAT KEY
- LONGBOAT KEY CASA DEL MAR
- LONGBOAT KEY MOORINGS
- LONGBOAT KEY MOORINGS MARINA
- LONGBOAT KEY MOORINGS MARINA 2
- LONGBOAT KEY TOWERS
- LONGBOAT LANDING
- LONGBOAT SHORES REV
- LONGBOAT TERRACE
- MARINA BAY
- MCCALLS BEACH CASTLE
- NEPTUNE ON LONGBOAT KEY
- NEW PASS SHORES
- NORTHGATE OF LONGBOAT KEY
- PELICAN HARBOUR
- PELICAN HARBOUR & BEACH CLUB
- PIERRE
- PLAYERS CLUB 3
- PLAYERS CLUB I
- PLAYERS CLUB II
- PLAYERS CLUB III
- PORTOBELLO
- PRESERVE/LONGBEACH
- PRIVATEER NORTH
- PRIVATEER SOUTH
- PROMENADE
- QUEENS HARBOUR
- RAUCH
- REGENT COURT
- REGENT PLACE PH 1
- REGENT PLACE PH 2
- SABAL COVE
- SAGE LBK
- SALTY ACRES
- SANCTUARY I
- SANCTUARY II
- SANCTUARY IV
- SAND CAY
- SANDS POINT
- SEA GATE CLUB
- SEA PINES
- SEAGRAPE INN
- SEAPLACE
- SEAPLACE I
- SEAPLACE II
- SEAPLACE III
- SEAPLACE V
- SEAPLACE VI
- SEASIDE OF LONGBOAT
- SILVER SANDS
- SLEEP LAGOON PARK
- SLEEPY LAGOON
- SLEEPY LAGOON PARK
- SLEEPY LAGOON PARK 2
- SLEEPY LAGOON PART NO 2
- SPANISH MAIN YACHT CLUB CONDO
- ST REGIS LONGBOAT KEY
- ST. REGIS
- ST. REGIS LONGBOAT KEY
- SUNSET BEACH
- SUNSET BEACH PH 2
- SUTTON PLACE
- TANGERINE BAY CLUB
- TENCON BEACH
- THE PRESERVE/LONGBEACH
- THE SHORE
- THE WESTCHESTER
- TIFFANY PLAZA
- TREE HOUSE
- TWIN SHORES BEACH & MARINA
- TWIN SHORES BEACH AND MARINA, INC.
- TWIN SHORES MOBILE HOME
- VEINTE
- VILLA DI LANCIA PH 1
- VILLA DOS PALMAS
- VIZCAYA AT LONGBOAT KEY PH 01
- VIZCAYA AT LONGBOAT KEY PHASE 1
- WATER CLUB 01 AT LONGBOAT KEY
- WATER CLUB AT LONGBOAT KEY
- WATER CLUB II/LONGBOAT KEY
- WENDY
- WESTCHESTER APTS
- WESTCHESTER CONDO APTS UN 3
- WHITNEY BEACH
- WHITNEY BEACH III
- WINDWARD BAY AMD
Market Summary
Current real estate data for Single Family in LONGBOAT KEY as of Jun 18, 2026
162
Single Family Listed
175
Avg DOM
986
Avg $ / SqFt
$3,040,569
Avg List Price
Property Summary
- Located in the BAY ISLES subdivision, 1571 HARBOR CAY LANE LONGBOAT KEY FL is a Single Family for sale in LONGBOAT KEY, FL, 34228. It is listed for $4,550,000 and features 4 beds, 4 baths, and has approximately 4,209 square feet of living space, and was originally constructed in 1987. The current price per square foot is $1,081. The average price per square foot for Single Family listings in LONGBOAT KEY is $986. The average listing price for Single Family in LONGBOAT KEY is $3,040,569. To schedule a showing of MLS#a4666688 at 1571 HARBOR CAY LANE in LONGBOAT KEY, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of MICHAEL SAUNDERS & COMPANY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 1571 HARBOR CAY LANE
LONGBOAT KEY, FL