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Longboat Key Real Estate

Longboat Key real estateSituated just off mainland Sarasota, Longboat Key real estate encompasses approximately 17 square miles of gorgeous gulf and bay properties. With pristine beaches and aquamarine ocean waters, Longboat Key continually draws in a population that fluctuates between 8,000 permanent residents to as many as 20,000 seasonal residents and tourists. Learn more about Longboat Key.

Longboat Key Homes & Condos for Sale

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
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845 Longboat Club Rd, Longboat Key, FL - $26,500,000

Residential, Single Family Home
  • 6 Beds
  • 8 Baths
  • 19,300 SQFT
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A Stunning Ode To The Majesty Of Renaissance Venice, Serenissima “the Most Serene” Is One Of The Finest Homes Ever Built In Florida. Incomparable In Architecture, Irreplaceable In Artistic Beauty And Situated On The Southern End Of The Coveted Lon...

Photo of Listing #A3989550

6633 Gulf Of Mexico Dr, Longboat Key, FL - $19,900,000

Residential, Single Family Home
  • 6 Beds
  • 11 Baths
  • 9,262 SQFT
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Magnificently Poised On 2.57 Pristine Acres On The Gulf Of Mexico You'll Find Ohana, A Breathtaking Tropical Hideaway Inspired By The Spirit Of Coastal South Africa And Southern Indonesia. Envisioned By The Owner & Brought To Life By Acclaimed Arc...

Photo of Listing #A4190234

5965 Gulf Of Mexico Dr, Longboat Key, FL - $14,750,000

Residential, Single Family Home
  • 7 Beds
  • 7 Baths
  • 10,087 SQFT
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Villa Sena Is Longboat Key’s Premier Beach Front 2-acre Private Estate With 150 Feet Of Pristine Sugar Sand Directly On The Gulf Of Mexico. Completed In 2007 And Meeting Current Hurricane Codes. With Over 10,000 Legal Square Feet Of Elegant Neocl...

Photo of Listing #A4167892

891 Longboat Club Rd, Longboat Key, FL - $8,500,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,974 SQFT
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The Most Desirable Address In The Sarasota, Longboat Key Area Is Situated On Over 134 Feet Of Direct Beach Front On The Gulf Of Mexico Behind The Gates Of The Longboat Key Club. This Extraordinary Residence Presents A Flawless Fusion Of Beachfront...

5050 Gulf Of Mexico Dr, Longboat Key, FL - $8,400,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 7,250 SQFT
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"acqua Vita - Water Of Life", Where Design And Function Flow In Concert With The Beauty Of Longboat Key And Sarasota Bay. This Magnificent Estate Is The Masterful Collaboration Of The Award-winning Firms Of Perrone Construction And Clifford M. Sc...

5060 Gulf Of Mexico Dr, Longboat Key, FL - $8,200,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 10,216 SQFT
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“winner Of Hgtv’s Home Sweepstakes - Making And Entrance.” Villa De Como Is A Splendid Expression Of Spanish Architecture On The Peaceful North End Of Longboat Key. Panoramic Bay Views Enhance The Supremely Luxurious Living Space, With Five Bedro...

Photo of Listing #A4167317

5080 Gulf Of Mexico Dr, Longboat Key, FL - $6,649,000

Residential, Single Family Home
  • 5 Beds
  • 8 Baths
  • 8,898 SQFT
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This European-inspired Bayfront Estate Is Immaculately Maintained, A Remarkable Display Of Custom Features And Elegant Finishes. Surrounded By Privacy Walls Of Tropical Landscaping With A Gated Entry, This Special Home Offers More Than 100’ Of Bay...

Photo of Listing #A4122384

415 L Ambiance Dr #ph-c, Longboat Key, FL - $5,999,000

Residential, Condo
  • 3 Beds
  • 5 Baths
  • 4,711 SQFT
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It Is Rare For A Property Such As This To Come On The Market, Situated On The South End Of The Key Behind The Gates Of The Longboat Key Club, This Represents A Unique Opportunity For Gulf Front Living. This L' Ambiance Penthouse Offers Both Direct...

Photo of Listing #A4166277

771 Old Compass Rd, Longboat Key, FL - $4,995,000

Residential, Single Family Home
  • 4 Beds
  • 6 Baths
  • 5,315 SQFT
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Exceptional Direct Bayfront Custom Key West Style Home Has Spectacular Water Views Plus Extraordinary Designer Details. The Entry Showcases Dramactic Reclaimed Cypress Wood Doors With Carved Impact Glass. Gorgeous French Oak Oiled Finished Wood Fl...

Photo of Listing #A4170677

55 Lighthouse Point Dr, Longboat Key, FL - $4,975,000

Residential, Single Family Home
  • 5 Beds
  • 5 Baths
  • 6,159 SQFT
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Exceedingly Glamorous, This Waterfront Residence Is A Singular Jewel Nestled Within A Gated Address Of Prestige— Lighthouse Point. This Private Enclave Commands A Position Of Esteem On A Peninsula Behind The Gates Of The Longboat Key Club. Immense...

5005 Gulf Of Mexico Dr #9, Longboat Key, FL - $4,800,000

Residential, Single Family Home
  • 3 Beds
  • 4 Baths
  • 3,590 SQFT
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Pre-construction To Be Built. "bonaire" Is An Exclusive New Gated Gulf Front Community On 3.5 Acres On Longboat Key And Is Nestled Between The Positano And Club Longboat. "bonaire" Will Feature Nine Custom Luxury Coastal Homes With A West Indies ...

661 Dream Island Rd, Longboat Key, FL - $4,695,000

Residential, Single Family Home
  • 6 Beds
  • 7 Baths
  • 5,203 SQFT
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Incredible Opportunity! This Custom Home Is One Of A Kind On Longboat Key. Privacy And Expansive Bay Views Of The Intracoastal Waterway And Sarasota Bay Plus A Private Boat Dock With Deep Water To Accommodate Up To 65 Ft Vessel Plus Other Water Cr...

Longboat Key

Homes & condos for sale on Longboat Key, FL have attracted island lovers for generations. Today, Longboat Key boasts some 1,500 single-family homes, 7,000 condominium units, and about 1,000 tourist accommodations. Real estate for sale ranges from maintenance-free vacation villas to luxury waterfront estates. In Longboat Key, you will find a boater’s paradise, plenty of privacy, well-maintained neighborhoods and common areas, golf, tennis, fitness, and other activity options, shopping and dining choices, and an ideal central location situated near St Armand's Circle and the downtown Sarasota arts district. Longboat Key is divided evenly between Manatee and Sarasota counties, both of which have thriving communities, while bridges connect Longboat Key to Lido Key and Anna Maria Island.

Longboat Key residents can enjoy getting to know a mix of neighbors who share a love for the casual, carefree island living that can be found here. Incorporated in 1955, Longboat Key is governed by locally-elected commissioners who, together with residents, have maintained thoughtful planning and zoning decisions that protect the island from unsightly signage, tourist shops, and neglected buildings. Attention to detail in planning and upkeep result in an island with caring residents, access to well-preserved beaches, parks, and a long, beautiful central drive surrounded by beautiful oleanders and tall, wispy Australian pines. For those who love sun, water, and proximity to all that beautiful Sarasota offers, Longboat Key is a place that's hard to beat.

Longboat Key History

Before Longboat Key real estate began development, and like so many other barrier islands, it was once home to tribal cultures and remained undeveloped until the turn of the 20th century. The earliest modern settlers arrived on the key in the late 1800s, and a thriving farming community grew, producing as many as 200-400 crates of produce a day. This included tomatoes, guavas, avocados, and various citrus products. Steamboats came from Tampa to drop off passengers and load the produce, but the un-named hurricane of 1921 changed everything—it destroyed the farms, salted the land, and raised the water level by up to six feet.

Development of the key as a prime residential and tourist area really began with famed magnate John Ringling’s purchase of hundreds of acres on the south end in the early 1920s. His vision for Longboat, Lido, and Bird Keys, along with his development of St. Armand’s Circle, really jump-started Longboat Key as a destination for homesteading or vacationing. Ringling started building the Ritz-Carlton hotel on New Pass in 1926, but the hotel was never finished and was torn down when Arvida purchased the land in 1962.

During the war, a portion of the then-sparsely populated island was used by the Air Force for target range practice, with pilots flying P-40s, B-26s, and P-51s. After the war, tourism in the area grew, along with the population, as the post-war economic boom made growth and development of the island a possibility.

Map of Longboat Key, FL

Longboat Key Real Estate Resources


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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.

Listing information last updated on June 29th, 2017 at 10:07am EDT.