Under contract-accepting backup offers. Nestled behind the gates of prestigious Bay Isles on Longboat Key, this exceptional residence offers over 3,000 square feet of thoughtfully designed living space surrounded by lush tropical landscaping and just moments from the Gulf of Mexico. Combining timeless architecture, spacious interiors, and resort-style outdoor living, this home delivers the privacy and elegance that define the Longboat Key lifestyle.
A grand entry welcomes you into an open and inviting floor plan featuring soaring ceilings, abundant natural light, and generous living and entertaining spaces. The expansive great room flows seamlessly into the dining area and well-appointed kitchen, complete with ample cabinetry, extensive counter space, and a convenient wet bar for effortless entertaining.
The first-floor primary suite serves as a private retreat with a spacious bedroom, large walk-in closet, and luxurious en-suite bath. Additional guest bedrooms are thoughtfully positioned for privacy and comfort, while the second floor offers a private guest suite with balcony access—perfect for visitors seeking their own space and enjoying tropical views.
Designed for year-round enjoyment, the screened outdoor living area is a true highlight. Relax poolside in the sparkling heated pool and spa, entertain under the covered lanai, or unwind amidst the lush tropical surroundings that create a secluded backyard oasis.
Located within the highly sought-after Bay Isles community, residents enjoy 24-hour gated security, beautifully maintained grounds, and exclusive access to the private Bay Isles Beach Club on the Gulf of Mexico. Just minutes away are the Longboat Key Club’s championship golf courses, tennis facilities, marina, waterfront dining, boutique shopping, and renowned St. Armands Circle.
Offering the perfect blend of luxury, privacy, and coastal convenience, this exceptional Longboat Key residence presents a rare opportunity to enjoy one of Sarasota’s most desirable island lifestyles.
A grand entry welcomes you into an open and inviting floor plan featuring soaring ceilings, abundant natural light, and generous living and entertaining spaces. The expansive great room flows seamlessly into the dining area and well-appointed kitchen, complete with ample cabinetry, extensive counter space, and a convenient wet bar for effortless entertaining.
The first-floor primary suite serves as a private retreat with a spacious bedroom, large walk-in closet, and luxurious en-suite bath. Additional guest bedrooms are thoughtfully positioned for privacy and comfort, while the second floor offers a private guest suite with balcony access—perfect for visitors seeking their own space and enjoying tropical views.
Designed for year-round enjoyment, the screened outdoor living area is a true highlight. Relax poolside in the sparkling heated pool and spa, entertain under the covered lanai, or unwind amidst the lush tropical surroundings that create a secluded backyard oasis.
Located within the highly sought-after Bay Isles community, residents enjoy 24-hour gated security, beautifully maintained grounds, and exclusive access to the private Bay Isles Beach Club on the Gulf of Mexico. Just minutes away are the Longboat Key Club’s championship golf courses, tennis facilities, marina, waterfront dining, boutique shopping, and renowned St. Armands Circle.
Offering the perfect blend of luxury, privacy, and coastal convenience, this exceptional Longboat Key residence presents a rare opportunity to enjoy one of Sarasota’s most desirable island lifestyles.
Property Details
Price:
$1,995,000
MLS #:
TB8515918
Status:
Active Under Contract
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
BAY ISLES
Neighborhood:
34228longboatkey
Listed Date:
Jun 5, 2026
Finished Sq Ft:
3,059
Total Sq Ft:
3,925
Lot Size:
12,268 sqft / 0.28 acres (approx)
Year Built:
2014
See this Listing
Schools
Elementary School:
Southside Elementary
Middle School:
Booker Middle
High School:
Booker High
Interior
Appliances
Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Range Hood, Refrigerator, Washer
Bathrooms
4 Full Bathrooms
Cooling
Central Air
Flooring
Brick/Stone, Carpet, Hardwood
Heating
Central, Electric, Zoned
Interior Features
Cathedral Ceiling(s), Central Vacuum, Crown Molding, Dry Bar, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s)
Laundry Features
Inside
Levels
Two
Exterior
Architectural Style
Custom, Mediterranean
Association Amenities
Gated, Security, Tennis Court(s), Vehicle Restrictions
Attached Garage YN
1
Community Features
Marina, Water Access, Buyer Approval Required, Deed Restrictions, Golf, Special Community Restrictions, Tennis Court(s)
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
East
Exterior Features
Balcony, Hurricane Shutters, Irrigation System, Lighting, Sliding Doors, Storage
Garage Spaces
3
Lot Features
FloodZone, In County, Oversized Lot
Open Parking YN
1
Other Structures
Storage
Parking Features
Circular Driveway, Garage Door Opener
Patio And Porch Features
Covered, Deck, Patio, Porch, Screened
Roof
Other
Security Features
Gated Community, Key Card Entry, Security System Owned, Smoke Detector(s)
Window Features
Blinds
Financial
HOA Fee
$1,250
HOA Fee 2
$2,392
HOA Fee 2 Frequency
Annually
HOA Fee Frequency
Annually
HOA Includes
Private Road, Security
HOA Name
Bay Isles Bayou Association Inc
HOA Name 2
Bay Isles Homeowners Association
HOA Phone
941-383-3200
Tax Year
2025
Taxes
$27,748
Map
Community
- Address3271 BAYOU ROAD 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 Jul 19, 2026
143
Single Family Listed
195
Avg DOM
1,023
Avg $ / SqFt
$3,138,470
Avg List Price
Property Summary
- Located in the BAY ISLES subdivision, 3271 BAYOU ROAD LONGBOAT KEY FL is a Single Family for sale in LONGBOAT KEY, FL, 34228. It is listed for $1,995,000 and features 4 beds, 4 baths, and has approximately 3,059 square feet of living space, and was originally constructed in 2014. The current price per square foot is $652. The average price per square foot for Single Family listings in LONGBOAT KEY is $1,023. The average listing price for Single Family in LONGBOAT KEY is $3,138,470. To schedule a showing of MLS#tb8515918 at 3271 BAYOU ROAD in LONGBOAT KEY, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of REAL BROKER, LLC. 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. 3271 BAYOU ROAD
LONGBOAT KEY, FL