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2020 HARBOURSIDE DRIVE 442

Longboat Key, FL, 34228

Active

$699,000

2

Bedrooms

2

Bathrooms

1,192 sqft

Living Area

1984

Year Built

$1,379

HOA / Annually

1

Days on Market

Dock & Water AccessMLS

Bay/Harbor FrontCanal FrontBay/Harbor📝 deep water

Data sources: SFWMD AHED waterway polygons · FHWA National Bridge Inventory 2024 · Not provided by the MLS or listing broker.

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.

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Location

Longboat Key, FL, 34228

No price history available for this property.

Displayed by Blue Mar Real Estate Group Inc., Licensed Florida Real Estate Broker (DBPR CQ1018554) · [email protected]

Listing courtesy of MICHAEL SAUNDERS & COMPANY via Stellar MLS

Last checked: 1 hour ago

Listing updated: September 18, 2026

© 2026 Stellar MLS. All rights reserved. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) program of Stellar MLS. Information is deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change, or withdrawal.

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FEMA Flood Zone AE
BFE: 8ft

Special Flood Hazard Area

View FEMA Flood Map →

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20%

$139,800 down

%
Principal & Interest$3,627/mo
Property Tax (est. ~1.2%, varies by county)$699/mo
Home Insurance (est.)$250/mo
HOA Fees$115/mo
Total Monthly Payment$4,691
Loan Amount: $559,200Rate: 6.75%
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$699,000Tour the dockSchedule a Showing