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: 6
Average Price: $843,333
Highest Price: $1,195,000
Lowest Price: $499,000
Average Size: 1,791 ft²
Average Price Per Square Foot: $511 per ft²

Explore Other Longboat Key Communities

Condos for Sale at Fairway Bay

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Image 0: A4700558

1906 Harbourside Drive 304, LONGBOAT KEY, FL - $1,195,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,135 SQFT
  • 39 DOM
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Behind The Gates Of Bay Isles, This Beautifully Updated Waterfront Townhome In Fairway Bay Offers The Rare Convenience Of A Private Deepwater Dock Accommodating Vessels Up To 40’. From Here, Sarasota Bay, Waterfront Dining And The Gulf Are Only Mi...

Image 1: A4689076

1932 Harbourside Drive 244, LONGBOAT KEY, FL - $1,175,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,192 SQFT
  • 156 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 2: A4703351

1906 Harbourside Drive 303, LONGBOAT KEY, FL - $799,000

Residential, Condominium
  • 2 Beds
  • 3 Baths
  • 1,590 SQFT
  • 16 DOM
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Located On A Boating Canal In Fairway Bay, This Property Offers The Rare Convenience Of Walk-down Access To Your Own Private Dock - Setting The Stage For Effortless Boat Launches And Afternoons Exploring Sarasota Bay. This Updated Two-bedroom, Two...

Image 3: TB8422578

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

Residential, Townhouse
  • 2 Beds
  • 3 Baths
  • 2,606 SQFT
  • 345 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 4: A4682869

2110 Harbourside Drive 523, LONGBOAT KEY, FL - $623,000

Residential, Condominium
  • 3 Beds
  • 2 Baths
  • 2,031 SQFT
  • 198 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 5: A4692494

1930 Harbourside Drive 122, LONGBOAT KEY, FL - $499,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,192 SQFT
  • 129 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 September 14th, 2026 at 4:52am 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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