2020 Harbourside Drive 442, LONGBOAT KEY, FL

$699,000

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2

Beds

2

Baths

1,192

Square feet

About 2020 Harbourside Drive 442

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.

Features of 2020 Harbourside Drive 442

MLS® # A4705717
Price $699,000
Bedrooms 2
Bathrooms 2.00
Full Baths 2
Square Footage 1,192
Year Built 1984
Type Residential
Sub-Type Condominium
Status Active
Taxes $7,658
HOA Fees $1,379
HOA Frequency Annually
Condo Fee $5,200
Condo Fee Frequency Quarterly
CDD N

Community Information

Address 2020 Harbourside Drive 442
Area Longboat Key
Subdivision FAIRWAY BAY 2 PH 1
City LONGBOAT KEY
County Sarasota
State FL
Zip Code 34228-4246

Amenities

Amenities Clubhouse, Elevator(s), Fitness Center, Gated, Lobby Key Required, Pickleball Court(s), Pool, Recreation Facilities, Security, Tennis Court(s), Trail(s)
Parking Circular Driveway, Common, Driveway, Ground Level, Guest, Off Street, Open
View Water
Is Waterfront Yes
Waterfront Bay/Harbor Front, Canal Front, Bay/Harbor
Has Pool No

Interior

Interior Features Ceiling Fan(s), Kitchen/Family Room Combo, Solid Surface Counters, Thermostat
Appliances Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Freezer, Refrigerator, Washer
Heating Central, Electric
Cooling Central Air
Fireplace No
# of Stories 5

Exterior

Exterior Features Balcony, Sidewalk, Sliding Doors
Roof Built-Up, Concrete, Membrane
Foundation Pillar/Post/Pier, Slab

School Information

Elementary Southside Elementary
Middle Booker Middle
High Booker High

Pet Information

Number of Pets 1
Size Small (16-35 Lbs.)
Weight 35
Restrictions See Association Docs

Rental Restrictions

Minimum Lease 2 Months

Additional Information

Date Listed September 17th, 2026
Zoning PD
Foreclosure No
Short Sale No
RE / Bank Owned No
Maintenance 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

Listing Details

OfficeMICHAEL SAUNDERS & COMPANY

Listing Map

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