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Property for sale at 2020 HARBOURSIDE DRIVE UNIT 442, LONGBOAT KEY, FL, 34228
Property for sale at 2020 HARBOURSIDE DRIVE UNIT 442, LONGBOAT KEY, FL, 34228
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2020 Harbourside Drive Unit 442Longboat Key, FL, 34228

2beds
2baths
1,192sqft
Condominium
Built in 1984
$2,758 Annually HOA Fee
$699,000
For sale
Price per sqft
$586
Days on market
42
Listed
Sep 10
MLS #A4705717Updated Sep 18, 2026

About this property

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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Property details

Property type
Condominium
Street address
2020 Harbourside Drive Unit 442
City
Longboat Key
State
FL
ZIP code
34228
Year built
1984
New construction
No
Attached property
No
Faces
Southwest
Rooms
4
Building stories
5
Living area
1,192 sqft
Total building area
1,312 sqft
Levels
One

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 20, 2026 at 8:01 AM EDT

Price & sale history

EventPrice
Listed for saleMLS #A4705717$699,000
History may be incomplete.
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Property for sale at 2020 HARBOURSIDE DRIVE UNIT 442, LONGBOAT KEY, FL, 34228
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