Fairway Bay

  • Description
  • Listings
  • Map
  • Contact

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!

… Read More

MLS® Listing Statistics

Total Listings: 11
Average Price: $799,764
Highest Price: $1,299,000
Lowest Price: $599,900
Average Size: 1,756 ft²
Average Price Per Square Foot: $471 per ft²

Explore Other Longboat Key Communities

Condos for Sale at Fairway Bay

Map Save this Search
Sort listings by:Price, High to Low
Image 0: A4680710

1918 Harbourside Drive 902, LONGBOAT KEY, FL - $1,299,000

Residential, Townhouse
  • 2 Beds
  • 3 Baths
  • 1,748 SQFT
  • 1 DOM
View details More Photos Save

Welcome To A Masterfully Reimagined Two-bedroom, 2.5-bath Furnished Town Home Offering Breathtaking, Full Open Views Of Sarasota Bay And The Vibrant City Skyline With Its Private Boat Dock. Arguably The Most Exquisite Residence In The Esteemed Fai...

Image 1: A4664458

2012 Harbourside Drive 2104, LONGBOAT KEY, FL - $895,000

Residential, Condominium
  • 3 Beds
  • 3 Baths
  • 2,135 SQFT
  • 87 DOM
View details More Photos Save

Discover Refined Coastal Living At Fairway Bay Impeccably Renovated From Top To Bottom, This Three-bedroom, Three-bath End-unit Townhome Offers The Perfect Blend Of Style, Function, And Coastal Charm. With 2,135 Square Feet Of Thoughtfully Desig...

Image 2: TB8422578

1926 Harbourside Drive 1302, LONGBOAT KEY, FL - $859,000

Residential, Townhouse
  • 2 Beds
  • 3 Baths
  • 2,606 SQFT
  • 164 DOM
View details More Photos Save

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 3: A4676699

1916 Harbourside Drive 803, LONGBOAT KEY, FL - $850,000

Residential, Condominium
  • 2 Beds
  • 3 Baths
  • 1,626 SQFT
  • 38 DOM
View details More Photos Save

Rarely Available Waterfront Condominium In The Coveted And Gated Fairway Bay Enclave Of Bay Isles On Longboat Key, With Beautiful Unobstructed Bay, Channel And Downtown Sarasota Vistas, Effortless Access To The Bay From Your Deeded 40' Boat Dock (...

1922 Harbourside Drive 1104, LONGBOAT KEY, FL - $795,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,316 SQFT
  • 74 DOM
View details More Photos Save

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 5: A4669215

2110 Harbourside Drive 526, LONGBOAT KEY, FL - $775,000

Residential, Condominium
  • 3 Beds
  • 2 Baths
  • 2,031 SQFT
  • 113 DOM
View details More Photos Save

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: A4671330

1932 Harbourside Drive 217, LONGBOAT KEY, FL - $695,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,442 SQFT
  • 98 DOM
View details More Photos Save

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 7: A4679908

2120 Harbourside Drive 612, LONGBOAT KEY, FL - $695,000

Residential, Condominium
  • 3 Beds
  • 2 Baths
  • 2,039 SQFT
  • 18 DOM
View details More Photos Save

It's All About Location. Close To Everything. Away From It All. Just A Short Drive From Sarasota, Longboat Key Offers Unrivaled Natural Beauty In A Coastal Retreat. This Single-story Traditional Condominium Makes The Most Of Its Spaciously Designe...

Image 8: TB8462750

1920 Harbourside Drive 1003, LONGBOAT KEY, FL - $684,500

Residential, Townhouse
  • 2 Beds
  • 3 Baths
  • 1,590 SQFT
  • 34 DOM
View details More Photos Save

Start Your Day With Glowing Sunrise Views Across Sarasota Bay From The Living Room, Primary Suite, And Screened Lanai, Where The Waterfront Setting Makes Every Moment Feel Like A Retreat. Located Within The Gated Waterfront Enclave Of Bay Isles, T...

Image 9: A4666650

1932 Harbourside Drive 254, LONGBOAT KEY, FL - $650,000

Residential, Condominium
  • 2 Beds
  • 2 Baths
  • 1,192 SQFT
  • 66 DOM
View details More Photos Save

Bask In Breathtaking Views Across Sarasota Bay To The Sparkling Downtown Skyline From This Beautifully Updated 2-bedroom, 2-bath Condo In The Exclusive, Guard-gated Community Of Bay Isles. Offered Turnkey Furnished, This Top-floor Residence In A M...

Image 10: A4668394

1912 Harbourside Drive 602, LONGBOAT KEY, FL - $599,900

Residential, Condominium
  • 2 Beds
  • 3 Baths
  • 1,590 SQFT
  • 119 DOM
View details More Photos Save

Discover The Ideal Blend Of Comfort, Convenience And Coastal Charm In This Beautifully Furnished Townhouse In Fairway Bay, A Sought-after, Gated Community Within Bay Isles On Longboat Key. Enjoy Easy Access To The Gorgeous Gulf Beach Of Longboat K...

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 February 14th, 2026 at 8:52am EST.

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

Save this Search
Sort listings by:Price, High to Low
Sort listings by: Price

Ask a Question. We are here to help!

Please provide a valid email address.