2020 HARBOURSIDE DRIVE 442, Longboat Key, FL 34228

• 2 beds |
• 2 baths |
• 1,192 sqft

Property Description

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.

Listing Status:

Active

Date Added:

September 17, 2026

Data Last Updated:

September 28, 2026 at 8:21PM

Listing Office:

MICHAEL SAUNDERS & COMPANY : 941-383-7591

Listing Agent:

Steve Walter : 941-809-0907

Contact:

941-383-7591

MLS ID:

A4705717

Interior

• General: Ceiling Fans(s)Kitchen/Family Room ComboSolid Surface CountersThermostat
• Rooms: Great RoomInside Utility
• Appliances: Built-In OvenDishwasherDisposalDryerElectric Water HeaterFreezerRefrigeratorWasher
• Laundry: Laundry Closet
• Flooring: CarpetTile
• A/C: Central Air
• Heating: CentralElectric

Exterior

• General: BalconySidewalk
• Parking: Circular DrivewayCommonDrivewayGround LevelGuestOff StreetOpen

Construction

• Roofing: Built-UpConcreteMembrane
• Windows: Shades
• General: ConcreteStuccoOnePillar/Post/PierSlab

Location

• Road/Access: Asphalt
• HOA Amenities: ClubhouseElevatorsFitness CenterGatedLobby Key RequiredPickleball Court(s)PoolRecreation FacilitiesSecurityTennis Court(s)Trail(s)Guard - 24 HourCommon Area TaxesPoolEscrow Reserves FundInsuranceMaintenance StructureMaintenance GroundsManagementPrivate RoadRecreational FacilitiesSecurity1379.0Annually
• Originating MLS: Stellar MLS
• County: Sarasota

Lot

• Zoning: PDUNIT 442 BLDG M-4 FAIRWAY BAY 2 PHASE 10008022050
• View: Water

Utilities

• Utilities: Cable ConnectedElectricity ConnectedPublicSewer ConnectedUnderground UtilitiesWater Connected
• Water: PrivatePublic
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Condominium