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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...

825 Longboat Club Rd, Longboat Key, FL - $18,000,000

Residential, Single Family Home
  • 6 Beds
  • 8 Baths
  • 12,095 SQFT
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The Enchanting Villa Del Sogno Estate Stands Behind The Gates Of The Longboat Key Club In A Separately Gated Enclave Of Eight Privately Gated Beachfront Estates. The Residence Centers Attention On The Gulf Of Mexico With Its Vivid Sunsets And Dyna...

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 - Sarasota's Premier Direct Beach Front Private Estate With 150 Feet Of Pristine Sugar Sand On The Gulf Of Mexico. Completed In 2007 And Meeting Current Hurricane Codes. Over 10,000 Square Feet Of Elegant Neoclassical Living Space, Fea...

6685 Gulf Of Mexico Dr, Longboat Key, FL - $12,500,000

Residential, Single Family Home
  • 6 Beds
  • 8 Baths
  • 12,752 SQFT
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Celebrate Gracious Florida Living In This 12,000-square-foot Beachfront Estate. Nestled On Nearly 200 Feet Of Pristine Sandy Beach On Longboat Key, This Exquisite Masterpiece Offers Stunning Views Of The Gulf Of Mexico. No Detail Has Been Overlook...

891 Longboat Club Rd, Longboat Key, FL - $8,400,000

Residential, Single Family Home
  • 5 Beds
  • 6 Baths
  • 5,974 SQFT
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This Spectacularly Positioned Beachfront Estate With 134-feet Of Frontage, In The Coveted Community Of Regent Court, Is Located Behind The South Gates Of Longboat Key Club. Situated On Over An Acre Of Gulf-front Property, This Five-bedroom Home Of...

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 #A4104843

5050 Gulf Of Mexico Dr, Longboat Key, FL - $7,900,000

Residential, Single Family Home
  • 5 Beds
  • 7 Baths
  • 7,250 SQFT
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Price Reduced!!! Brand New Construction! "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 O...

Photo of Listing #A4198011

5080 Gulf Of Mexico Dr, Longboat Key, FL - $6,495,000

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...

2251 Gulf Of Mexico #504, Longboat Key, FL - $6,100,000

Residential, Condo
  • 3 Beds
  • 4 Baths
  • 3,833 SQFT
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Nothing Compares To Aria, A Coastal Contemporary Enclave Built On One Of The Last & Most Coveted Beachfront Sites On South Longboat Key. Now There Is One Residence Available At Aria, The Gulf Front Corner Penthouse With The Most Gulf Frontage Of A...

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...

661 Dream Island Rd, Longboat Key, FL - $4,995,000

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 December 15th, 2017 at 2:35pm EST.