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: 10
Average Price: $815,000
Highest Price: $1,200,000
Lowest Price: $579,000
Average Size: 1,685 ft²
Average Price Per Square Foot: $518 per ft²

Explore Other Longboat Key Communities

Condos for Sale at Fairway Bay

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Image 0: A4689076

1932 Harbourside Drive 244, LONGBOAT KEY, FL - $1,200,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,192 SQFT
  • 58 DOM
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Welcome To This Breathtaking, Fully Remodeled, Turnkey Furnished Contemporary Residence In Fairway Bay—nestled On Picturesque Longboat Key. From The Moment You Enter, You're Greeted By A Thoughtfully Redesigned Open Floor Plan, Elevated Ceilings, ...

Image 1: A4686721

2120 Harbourside Drive 623, LONGBOAT KEY, FL - $1,095,000

Residential, Condominium
  • 3 Beds
  • 2 Baths
  • 2,031 SQFT
  • 74 DOM
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Step Into Coastal Elegance In This Fully Renovated Three-bedroom, Two-bathroom Fairway Bay Residence, Where Every Detail Has Been Thoughtfully Reimagined. A Charming Private Lanai And Seating Area Welcome You Before Entering The Unit, Setting The ...

Image 2: A4686674

2020 Harbourside Drive 417, LONGBOAT KEY, FL - $899,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,715 SQFT
  • 63 DOM
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A Vibrant Expression Of Style And Care, This 2br/2ba Corner Residence Set On The First Living Level Of Fairway Bay Offers 1,715 +/- Sq. Ft. Of Thoughtfully Designed Space In One Of Longboat Key's Most Amenity-rich Communities Behind The Gates Of B...

Image 3: A4683819

1912 Harbourside Drive 604, LONGBOAT KEY, FL - $835,000

Residential, Townhouse
  • 3 Beds
  • 3 Baths
  • 2,207 SQFT
  • 98 DOM
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Embrace The Island Life Style Within The Gates Of Longboat Key's Premier Resort Community Of Bay Isles. You'll Love This Spacious Townhome-style Condo In Fairway Bay. Designed With Soaring Ceilings And Large Windows To Allow Maximum Light And Expa...

Image 4: A4684680

2000 Harbourside Drive 1501, LONGBOAT KEY, FL - $790,000

Residential, Townhouse
  • 2 Beds
  • 2 Baths
  • 1,370 SQFT
  • 89 DOM
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Behind The Gates Of Bay Isles, A Private Country Club Community, Lies An Immaculate 2-bedroom, 2-bath End-unit Townhouse With A Side-by-side 2-car Garage Plus Extra Space For Hobbies Or Storage. Upgrades Abound: Lvp Flooring Throughout, Upgraded C...

Image 5: TB8422578

1926 Harbourside Drive 1302, LONGBOAT KEY, FL - $769,000

Residential, Townhouse
  • 2 Beds
  • 3 Baths
  • 2,606 SQFT
  • 247 DOM
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Gated, Deeded Private Beach Access! This Is A Rare Thing To Be Found On The Keys! The Main Level With Plantation Shutters And Hardwood Floors Includes The Kitchen, Dining And Living Areas. The Kitchen Has Subzero And Jenn-air Built In Stainless St...

Image 6: A4666101

1922 Harbourside Drive 1104, LONGBOAT KEY, FL - $725,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,316 SQFT
  • 186 DOM
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Experience The Ultimate Resort Lifestyle—where Every Day Feels Like A Vacation. Take A Refreshing Dip In The Pool, Enjoy A Tranquil Walk Along The Bay, Or Bask In The Warm Florida Sun On The White Sandy Beach. This Spacious 2-bedroom, 2-bath Townh...

Image 7: A4682869

2110 Harbourside Drive 523, LONGBOAT KEY, FL - $659,000

Residential, Condominium
  • 3 Beds
  • 2 Baths
  • 2,031 SQFT
  • 100 DOM
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Welcome To The Atrium—one Of Longboat Key's Most Exceptional Waterfront Addresses. Perfectly Positioned Along The Sparkling Waters Of Sarasota Bay, This Stunning Three-bedroom Residence Offers Breathtaking Panoramic Views That Will Captivate You F...

Image 8: A4688978

1932 Harbourside Drive 242, LONGBOAT KEY, FL - $599,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,192 SQFT
  • 53 DOM
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Value Opportunity Behind The Gates Of Bay Isles In The Highly Sought After Fairway Bay Community. This Turnkey Furnished Move-in Ready Two-bedroom, Two-bathroom Residence Presents An Exceptional Chance To Enjoy The Longboat Key Lifestyle Along Wit...

Image 9: A4692494

1930 Harbourside Drive 122, LONGBOAT KEY, FL - $579,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,192 SQFT
  • 31 DOM
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Welcome To Your Waterfront Retreat In The Highly Sought-after Fairway Bay Community, Where Relaxed Coastal Living Meets Thoughtful Design And Modern Comfort. This Beautifully Renovated 2-bedroom, 2-bath Condominium Offers Nearly 1,200 Square Feet ...

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 6th, 2026 at 7:52pm 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:
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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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