Fairway Bay

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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: 7
Average Price: $938,714
Highest Price: $1,685,000
Lowest Price: $669,000
Average Size: 1,502 ft²
Average Price Per Square Foot: $623 per ft²

Explore Other Longboat Key Communities

Condos for Sale at Fairway Bay

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Image 0: A4561559

1910 Harbourside Drive 501, LONGBOAT KEY, FL - $1,685,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,135 SQFT
  • 78 DOM
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Fairway Bay On Longboat Key… The Best Of All, Bay And Bayou Views, Your Own Boat Dock Outside Your Door, 3 Bedrooms Plus A Den, 3 Full Baths, And A Complete Renovation! This Impressive Townhome That Was Beautifully Renovated By Lee Heineman With T...

Image 1: A4569655

1930 Harbourside Drive 122, LONGBOAT KEY, FL - $998,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,192 SQFT
  • 24 DOM
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Sarasota Bay Is Your Backyard With Endless Water Views….as Well As The Mainland And The Sarasota Skyline. Instant Enjoyment Awaits You In This Bright, Airy, Two-bedroom, Two-bath Residence With A Southeastern Exposure. This "gem" Will Be Someone's...

Image 2: A4567109

1928 Harbourside Drive 1401, LONGBOAT KEY, FL - $910,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,375 SQFT
  • 47 DOM
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Price Improvement And Being Sold Partially Furnished! The Sellers Of This Fantastic Condo Are Motivated! Bring Your Offer Today And Make This Coastal Chic Updated 2 Bedroom, 2 Bath, 2 Story Townhome, Located In Fairway Bay, A Sought After Bayf...

Image 3: A4566512

1930 Harbourside Drive 141, LONGBOAT KEY, FL - $895,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,442 SQFT
  • 56 DOM
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Outstanding Waterfront Opportunity Awaits In A Rarely Available Corner Largest 2 Bedroom, 2 Bath Plus Office Area South Facing Views Of The Open Sarasota Bay, City, & Waterways With Private Nature Views From Two Terraces. Refreshed With Style The ...

2000 Harbourside Drive 1503, LONGBOAT KEY, FL - $715,000

Residential, Condominium
  • 2 Beds
  • 3 Baths
  • 1,590 SQFT
  • 101 DOM
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This 2 Br 2.5 Bath Townhome Offers The Opportunity For Privacy And Style In One Of The Most Sought After Communities On Longboat Key. Soaring 2 Story Skylit Ceilings And An Abundance Of Windows Fill The Main Living Level Space With Light. The Li...

Image 5: A4553987

2004 Harbourside Drive 1703, LONGBOAT KEY, FL - $699,000

Residential, Townhouse
  • 2 Beds
  • 3 Baths
  • 1,590 SQFT
  • 145 DOM
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Oversized Garage And Large A/c Storage Room On The Ground Level Of This 2 Story Townhouse. Private Gated Bay Isles South Community Is Highly Sought After Fairway Bay Neighborhood Is Maintenance Free. The Main Floor Features An Eat-in Kitchen Wit...

Image 6: A4567623

1932 Harbourside Drive 222, LONGBOAT KEY, FL - $669,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,192 SQFT
  • 45 DOM
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A Fantastic Opportunity To Own This Furnished 2-bedroom Waterfront Residence Behind The Private Gates Of Bay Isles. This Home Features A Welcoming Interior And Contains A Flow-through Living/dining Area And Relaxed Living Spaces While Taking In Th...

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 1st, 2023 at 2:20pm 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.


  • 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

1900 Harbourside Dr
Longboat Key, FL 34228
Year Built:
1982 to 1988
Number of Units:
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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