Fairway Bay

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Overview

Consisting of townhouses and four mid-rise condos of five stories each, Fairway Bay is a secluded enclave with a wide selection of living options. With a guard gate and round the clock security, residents feel safe and secure as they you relax in their homes.

Below are all of the condos for sale in the Fairway Bay condominium on Longboat Key Florida. All real estate listings are updated daily from the Multiple Listing Service (MLS).

To learn more about any of these condos or receive email updates when new listings hit the market, simply give us a call at 941-544-6467 or send us an email. We are here to help!

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MLS® Listing Statistics

Total Listings: 13
Average Price: $925,900
Highest Price: $1,650,000
Lowest Price: $599,000
Average Size: 1,849 ft²
Average Price Per Square Foot: $502 per ft²

Explore Other Longboat Key Communities

Condos for Sale at Fairway Bay

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Image 0: A4645723

2020 Harbourside Drive 454, LONGBOAT KEY, FL - $1,650,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,462 SQFT
  • 87 DOM
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An Incredible Opportunity To Own A Rarly Redone To The Highest Stanard Condo. Now Available Sought After Top Floor Three Bedroom Condo Offering Almost 2500, Sq. Ft. Of Living Space. The Special Feature Of This Condo Is The Amazing Unobstructed Vie...

Image 1: N6136414

2020 Harbourside Drive 424, LONGBOAT KEY, FL - $1,355,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,462 SQFT
  • 155 DOM
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Welcome To 2,400+ Square Feet Of Refined Living With Breathtaking Panoramic Bay Views. This Residence Offers An Expansive Open Floor Plan That Includes Two Primary Suites In A Split Configuration, Ensuring Privacy And Comfort With A 3rd Guest Bed...

Image 2: A4632715

1904 Harbourside Drive 204, LONGBOAT KEY, FL - $999,950

Residential, Townhouse
  • 3 Beds
  • 3 Baths
  • 2,135 SQFT
  • 181 DOM
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Motivated Seller, Reduced Over $150,000. Welcome To Fairway Bay’s Finest Remodeled, Corner Unit That Is Bathed In Natural Light That Captures The Beauty Of The Finest Of Finishes In This Completely “move In Ready” 3 Bedroom 3 Bath Townhome. Locate...

Image 3: A4643392

1900 Harbourside Drive 102, LONGBOAT KEY, FL - $995,000

Residential, Condominium
  • 2 Beds
  • 3 Baths
  • 1,590 SQFT
  • 100 DOM
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Experience The Best Of Longboat Key Living In This Updated 2-bedroom, 2.5-bath Townhouse In The Exclusive Fairway Bay Community, Behind The Gates Of Bay Isles. Offering 1,590 Square Feet Of Well-designed Living Space, This Home Includes A Deeded D...

Image 4: A4640574

2012 Harbourside Drive 2104, LONGBOAT KEY, FL - $975,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,135 SQFT
  • 122 DOM
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Impeccably Renovated From Top To Bottom, This Exceptional Townhome Offers Elegant Living With High-end Finishes Throughout. The Gourmet Kitchen Features Newly Updated Cabinet Doors (nov. 2023) And Sleek Appliances (jan. 2018), Complemented By Hard...

Image 5: A4635275

2110 Harbourside Drive 526, LONGBOAT KEY, FL - $830,000

Residential, Condominium
  • 3 Beds
  • 2 Baths
  • 2,031 SQFT
  • 143 DOM
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Carefree Living Awaits You With Beautiful Panoramic Views Of Sarasota Bay In This Beautiful Condominium At The Atrium On Longboat Key Inside Bay Isles. This Spacious Updated Unit Is Move-in Ready For You To Enjoy All That Florida Living Has To Off...

Image 6: A4645559

1928 Harbourside Drive 1403, LONGBOAT KEY, FL - $825,000

Residential, Condominium
  • 2 Beds
  • 3 Baths
  • 1,590 SQFT
  • 89 DOM
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Exciting New Low Price! Luxury And Style Await In This Beautifully Updated Townhouse, Located Behind The Gates Of The Exclusive Bay Isles Resort. With 1,590 Sq. Ft. Of Meticulously Designed And Finished Indoor Living Space Plus Another 1,100 Sq. F...

Image 7: A4652066

2120 Harbourside Drive 617, LONGBOAT KEY, FL - $815,000

Residential, Condominium
  • 3 Beds
  • 2 Baths
  • 2,105 SQFT
  • 27 DOM
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Experience Refined Bayfront Living In This Spacious 3br/2ba, 2,105± Sq. Ft. Residence At The Atrium In Bay Isles, Just Minutes From St. Armands Circle And Downtown Sarasota. This Rare Walk-down Residence Is Turnkey Furnished And Offers Sweeping Vi...

Image 8: A4645431

1912 Harbourside Drive 602, LONGBOAT KEY, FL - $775,000

Residential, Condominium
  • 2 Beds
  • 3 Baths
  • 1,590 SQFT
  • 90 DOM
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Experience Longboat Key Living At Its Finest In The Community Of Fairway Bay, Just Beyond The Gates Of Bay Isles! This Two-bedroom, 2.5-bath Plus Bonus Room Townhouse Offers Three Levels Of Serene Island Living. The Main Level Boasts A Well-design...

Image 9: A4636284

2110 Harbourside Drive 522, LONGBOAT KEY, FL - $773,750

Residential, Condominium
  • 3 Beds
  • 2 Baths
  • 2,039 SQFT
  • 145 DOM
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This Building Does Not Allow Dogs, Cats Are Okay. Installed Are A Brand New Trane 3.5 Ton Hvac System And A New Brand New Electrical Panel. The Condo Association Has A Landscaping Renewal Project That Will Cost About $350,000 And This Money Is Alr...

Image 10: A4646279

1932 Harbourside Drive 217, LONGBOAT KEY, FL - $749,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,442 SQFT
  • 79 DOM
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Nestled In The Sought-after Fairway Bay Community On Longboat Key, This 2br, 2ba Residence Offers The Perfect Blend Of Serene Bayfront Living And Luxurious Amenities, All Behind The Exclusive Gates Of Bay Isles. As An End Unit, First Floor Walk-do...

Image 11: A4643960

1930 Harbourside Drive 136, LONGBOAT KEY, FL - $695,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,270 SQFT
  • 91 DOM
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*no Storm Damage - Welcome To This Upgraded And Partially Furnished 2-bedroom, 2-bathroom Condo On The Coveted Third Floor, Where Breathtaking Bay Views Greet You As Soon As You Step Inside. Elegantly Designed With A Blend Of Contemporary Style An...

Image 12: A4645253

1930 Harbourside Drive 142, LONGBOAT KEY, FL - $599,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,192 SQFT
  • 90 DOM
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Full Unobstructed And Private Views Of The Intracoastal Waterway, Sarasota Bay And The Dramatic City Skyline And Ringling Bridge From The Protected Balcony + 1 Under-building Parking Spot. This Immaculately Maintained, Never-rented Condominium Is ...

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; availability of any listing should always be independently verified.

Listing information is provided for consumer 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.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on June 19th, 2025 at 2:35pm EDT.

Fairway Bay Description (continued)

Conveniently situated towards the southern end of Longboat Key Florida, Fairway Bay offers resort style living just minutes away from Sarasota's ample activities. Enjoy the posh yet serene lifestyle while indulging yourself in fine shopping and dining of St. Armands Circle or Downtown Main Street.

Amenities

  • Two tennis courts
  • 2 heated pools
  • Spa
  • Hot tub
  • Fitness center
  • Clubhouse
  • Bike paths
  • Private beach access through the private Bay Isles Beach Club

Outdoor activities such as golfing, hiking, biking, kayaking, canoeing and many more are also available in close proximity.

Community Information

Address:
1900 Harbourside Dr
Longboat Key, FL 34228
Year Built:
1982 to 1988
Number of Units:
287
Size:
1192 to 2632 square feet
Price Range:
$500,000s to over $1 million
Community Info:
Read More Below

If you like Fairway Bay, three other similar condos on the bayside of the island are Grand Bay, Marina Bay ;and Tangerine Bay.

If you prefer something directly on the beach, take a look at the Promenade, Sea Gate Club, Islands West, Sunset Beach or The Water Club.

Map of Fairway Bay

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