Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within the Longboat Key Club setting. Residence #442 at 2020 Harbourside Drive offers 1,312 square feet of bright, airy living space with two bedrooms and two bathrooms—an inviting coastal retreat where the bay becomes part of everyday life. Floor-to-ceiling views from the kitchen, dining area, and living room create a memorable backdrop for daily living and entertaining, while the private balcony is an ideal place to begin the day with a Sarasota Bay sunrise or settle in for the evening as the sky changes over the water. Keep watch for passing boats, coastal birds, and the occasional manatee in the bay below. The residence has been thoughtfully updated with a kitchen featuring granite countertops, a granite breakfast bar, stainless-steel appliances, and a newer microwave. A front-loading LG washer and dryer are included for everyday convenience. Ceramic tile flooring extends throughout the main living areas and guest spaces, while the primary bedroom features warm wood flooring. Fairway Bay offers a resort-inspired waterfront lifestyle with scenic walking paths, a heated swimming pool and spa, fitness facilities, social spaces, tennis courts, and paddle sports. Beyond the bayfront setting, owners enjoy deeded access to the Bay Isles Beach Club, providing a private connection to Longboat Key’s renowned Gulf beaches. It is the best of both waterfront worlds: tranquil Sarasota Bay just outside your door and the Gulf of Mexico’s white-sand shoreline close by. The community’s central island location makes it easy to walk or bike to nearby conveniences, including grocery shopping, pharmacy services, and tennis. For those who wish to expand their recreational options, membership opportunities may be available through the nearby Longboat Key Club, with its golf, tennis, dining, fitness, spa, and full-service deep-water marina amenities. St. Armands Circle is moments away for boutique shopping and acclaimed dining, while downtown Sarasota offers a vibrant extension of the island lifestyle with arts, culture, restaurants, and waterfront attractions. This is a rare opportunity to enjoy a beautifully updated fourth-floor bayfront residence where views, private beach access, resort-style amenities, and the effortless rhythm of Longboat Key living come together.
Property Details
Price:
$699,000
MLS #:
A4705717
Status:
Active
Beds:
2
Baths:
2
Type:
Condo
Subtype:
Condominium
Subdivision:
FAIRWAY BAY 2 PH 1
Neighborhood:
34228longboatkey
Listed Date:
Sep 17, 2026
Finished Sq Ft:
1,192
Total Sq Ft:
1,312
Year Built:
1984
See this Listing
Schools
Elementary School:
Southside Elementary
Middle School:
Booker Middle
High School:
Booker High
Interior
Appliances
Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Freezer, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Porcelain Tile
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Kitchen/Family Room Combo, Solid Surface Counters, Thermostat
Laundry Features
Laundry Closet
Levels
One
Exterior
Association Amenities
Clubhouse, Elevator(s), Fitness Center, Gated, Lobby Key Required, Pickleball Court(s), Pool, Recreation Facilities, Security, Tennis Court(s), Trail(s)
Attached Garage YN
1
Community Features
Bay/Harbor Front, Canal Front, Buyer Approval Required, Clubhouse, Fitness Center, Gated Community – Guard, Pool, Sidewalks, Tennis Court(s)
Construction Materials
Concrete, Stucco
Direction Faces
Southwest
Exterior Features
Balcony, Sidewalk, Sliding Doors
Open Parking YN
1
Parking Features
Circular Driveway, Common, Driveway, Ground Level, Guest, Off Street, Open
Roof
Built-Up, Concrete, Membrane
Security Features
Fire Sprinkler System, Gated Community, Security Gate, Smoke Detector(s)
View
Water
Waterfront Features
Bay/Harbor Front, Canal Front, Bay/Harbor
Window Features
Shades
Financial
HOA Fee
$1,379
HOA Fee 2
$1,379
HOA Fee 2 Frequency
Annually
HOA Fee Frequency
Annually
HOA Includes
24-Hour Guard, Common Area Taxes, Community Pool, Escrow Reserves Fund, Insurance, Maintenance Structure, Maintenance Grounds, Manager, Pool Maintenance, Private Road, Recreational Facilities, Security
HOA Name
Nat Veal
HOA Name 2
Bay Isles Master
HOA Phone
941-383-2701
Tax Year
2025
Taxes
$7,658
Map
Community
- Address2020 HARBOURSIDE DRIVE UNIT 442 LONGBOAT KEY FL
- SubdivisionFAIRWAY BAY 2 PH 1
- CityLONGBOAT KEY
- CountySarasota
- Zip Code34228
Subdivisions in LONGBOAT KEY
- 360 NORTH PH II
- 7981 – LONGBOAT KEY MOORINGS
- 8177 – LONGBOAT KEY MOORINGS MARINA 2
- ACREAG0001
- AQUARIUS CLUB
- ARBOMAR
- ARBOMAR APTS
- ARIA LONGBOAT KEY
- AVIGNON VILLAS
- BAILEY-DOBSON
- BAY ISLES
- BAYOU HAMMOCK
- BAYPORT BCH & TEN PH A
- 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
- 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 4
- GRAND BAY 6
- GULFSHORE OF LONGBOAT KEY
- HARBOR OAKS PH I & II
- HARBOUR OAKS
- HARBOUR OAKS 2
- HARBOUR OAKS PH I & II
- HARBOUR VILLA CLUB AT THE BUCCANEER
- HARRIS BAYOU
- 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
- ISLANDER CLUB OF LONGBOAT
- ISLANDS WEST
- L AMBIANCE
- L AMBIANCE 1
- L AMBIANCE AT LONGBOAT KEY CLUB
- L AMBIANCE AT LONGBOAT KEY CLUB PH 02
- LAGUNA YACHT VILLAGE
- 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 ESTATES
- LONGBOAT KEY MOORINGS
- LONGBOAT KEY MOORINGS MARINA
- LONGBOAT KEY MOORINGS MARINA 2
- LONGBOAT KEY TOWERS
- 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
- PORTOBELLO
- PRESERVE/LONGBEACH
- PRIVATEER NORTH
- PRIVATEER SOUTH
- PROMENADE
- QUEENS HARBOR A/K/A MANCHESTER BAY
- QUEENS HARBOUR
- RAUCH
- REGENT COURT
- REGENT PLACE PH 2
- SABAL COVE
- SAGE LBK
- SALTY ACRES
- SANCTUARY I
- SANCTUARY II
- SANCTUARY IV
- SAND CAY
- SANDS POINT
- SARASOTA OUTRIGGER
- SEA GATE CLUB
- SEA PINES
- SEAGRAPE INN
- SEAPLACE
- SEAPLACE I
- SEAPLACE II
- SEAPLACE III
- SEAPLACE V
- SEAPLACE VI
- SEASIDE OF LONGBOAT
- 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 BANYAN BAY CLUB
- 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
- WENDY
- WESTCHESTER APTS
- WESTCHESTER CONDO APTS UN 3
- WHITNEY BEACH
- WHITNEY BEACH III
- WINDWARD BAY AMD
Market Summary
Current real estate data for Condo in LONGBOAT KEY as of Sep 17, 2026
164
Condo Listed
163
Avg DOM
728
Avg $ / SqFt
$1,251,875
Avg List Price
Property Summary
- Located in the FAIRWAY BAY 2 PH 1 subdivision, 2020 HARBOURSIDE DRIVE UNIT 442 LONGBOAT KEY FL is a Condo for sale in LONGBOAT KEY, FL, 34228. It is listed for $699,000 and features 2 beds, 2 baths, and has approximately 1,192 square feet of living space, and was originally constructed in 1984. The current price per square foot is $586. The average price per square foot for Condo listings in LONGBOAT KEY is $728. The average listing price for Condo in LONGBOAT KEY is $1,251,875. To schedule a showing of MLS#a4705717 at 2020 HARBOURSIDE DRIVE UNIT 442 in LONGBOAT KEY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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. 2020 HARBOURSIDE DRIVE UNIT 442
LONGBOAT KEY, FL

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