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2020 Harbourside Drive, Unit 442Longboat Key, FL 34228Price: $699,000

  • Price: $699,000
  • Est. Mortgage of $/month
  • 4 Days on Market
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Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
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  • $699,000List Price
  • ActiveStatus
  • 56Number of Photos
  • 27.359559Latitude
  • 2020 Harbourside DriveAddress
  • Harbourside DriveStreet
  • 442Unit Number
  • Longboat KeyTown
  • FLState
  • 34228Zip
  • SarasotaCounty
  • A4705717MLS Number
  • 09/17/2026Date Listed
  • 2Bedrooms
  • 2Full Bath
  • 1,192Square Feet
  • 1984Year Built
  • 4 DaysOnMarket Date

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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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LISTING COURTESY OF Steve Walter and Janet Walter of MICHAEL SAUNDERS & COMPANY (941-383-7591)

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of September 20, 2026 5:32 PM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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Property Details of 2020 Harbourside Drive, Unit 442

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