Longboat Key, FL Homes

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  /58

  $1,699,000

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft

  2425 Gulf of Mexico Dr Unit 7D, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Don’t miss your chance to own a slice of paradise in the highly sought-after Sea Gate Club on historic Longboat Key! Step into unit #7D, where you’ll be captivated by breathtaking, unobstructed views of the Gulf and beach that seem to stretch on forever. This highly desirable two-bedroom, two-bath split floor plan offers the perfect combination of

  Matt Bohanon HOUSE MATCH

  2425 Gulf of Mexico Dr Unit 7D, Longboat Key, FL 34228
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  /40

  $5,500 per month

  • 3 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • Condo for Rent

  4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228

  Longboat Key vacation rental, rarely available Tiffany Plaza direct Gulf Front condo with amazing views! As you enter your gaze will be drawn to the turquoise waters of the Gulf of Mexico and the serene beach frontage. This lovely home offers 2 beds & 2 baths, plus a bonus office space with a twin Murphy bed! The kitchen and the baths have been updated, the primary bedroom offers a King bed, walk

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
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  /2

  $500,000 Sold Jul 16, 2025

  • 1,416 Sq Ft
  • $353/SF
  • 110 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1954

  651 Fox St, Longboat Key, FL 34228

  Opportunity is knocking! Currently one of the lowest priced homes on Longboat Key!! Bring your vision and reimagine this wonderful spot for your own island paradise! This home and the separate 2 story apartment were both completely renovated before the storm. A newer metal roof and storm rated windows and doors kept the home and apartment safe from the wind, but were damaged by water intrusion

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  651 Fox St, Longboat Key, FL 34228
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  /47

  Est $1,242,559 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  1135 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  1135 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
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  /64

  $795,000

  • 3 Beds
  • 2 Baths
  • 2,031 Sq Ft

  2110 Harbourside Dr Unit 526, Longboat Key, FL 34228

  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 offer! The large kitchen is open to the dining/living rooms that overlook the gorgeous Bay. You can enjoy beautiful sunrises or evening gatherings from

  Jessica Bow RE/MAX PALM

  2110 Harbourside Dr Unit 526, Longboat Key, FL 34228
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  /18

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,257 Sq Ft
  • Condo for Rent

  Unlisted Address

  SEAPLACE on LONGBOAT KEY. Relax and spend your winter days at this tropical seaside paradise. This pretty two bedroom condominium is well appointed with a king size bed in the primary suite. Primary bathroom has a walk in shower. SEAPLACE has all the amenities. to enjoy your stay: Two swimming pools, tennis courts, fitness center, clubhouse, and the most amazing beach on LBK. Just minutes to ST

  Jane Hunter JENNETTE PROPERTIES INC

  Unlisted Address
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  /2

  $950,000 Sold Jul 15, 2025

  • 1,235 Sq Ft
  • $769/SF
  • 60 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  2301 Gulf of Mexico Dr Unit 26, Longboat Key, FL 34228

  This tranquil second floor residence at Islander Club of Longboat Key boasts direct full views of the Gulf of Mexico, complete with spellbinding sunsets, sandy shores, and soothing sounds of the surf. An enchanting beachfront getaway, this furnished condo offers two bedrooms and two full bathrooms, with a spacious open living & dining space, and a private terrace that spans almost the entire

  Doug Parks MICHAEL SAUNDERS & COMPANY

  2301 Gulf of Mexico Dr Unit 26, Longboat Key, FL 34228
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  /18

  Est $240,584 Not Listed For Sale

  • Studio

  2600 Harbourside Dr Unit K-01, Longboat Key, FL 34228

  2600 Harbourside Dr Unit K-01, Longboat Key, FL 34228
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  /51

  $1,495,000

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft

  2295 Gulf of Mexico Dr Unit 23S, Longboat Key, FL 34228

  Set directly on the shores of the Gulf of Mexico, this beautifully renovated residence in the Islander Club captures the essence of Longboat Key beachfront living. Located in the desirable South Tower, this 2BR/2BA home showcases a fresh coastal design with wide-plank flooring, crown molding, recessed lighting, and an open layout oriented to the water. The kitchen exudes coastal charm with stone

  Bruce Myer COLDWELL BANKER REALTY

  2295 Gulf of Mexico Dr Unit 23S, Longboat Key, FL 34228
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  /47

  $4,800 per month

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Condo for Rent

  3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228

  VACATION RENTAL!!! AVAILABLE JAN - MARCH 2026! Spacious 6th floor condo awaits your arrival! This lovely 2 Bedroom, 2 Bath condo is inviting and warm and features an updated kitchen with granite counter tops and appliances. Stunning views await you from most rooms! This bright and airy unit provides views of Buttonwood Bayou and Sarasota Bay whether you're sitting inside or relaxing on your

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
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  /2

  $650,000 Sold Jul 15, 2025

  • 1,540 Sq Ft
  • $422/SF
  • 288 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  780 Tarawitt Dr, Longboat Key, FL 34228

  Home available to show and was unaffected by the recent Hurricane Milton. Majestic Waterfront Living in Longboat Key boasts DEEDED BEACH ACCESS to a private Gulf of Mexico beach and is walking distance to renowned Harry’s Kitchen and Delicatessen. Nestled in the serene beauty of Longboat Key, this waterfront 3-bedroom, 2-bathroom ranch home spans over 1,500 Sq Ft of an unparalleled blend of

  Sophia Kramedas-Ghanayem KW SUNCOAST

  780 Tarawitt Dr, Longboat Key, FL 34228
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  /91

  Est $1,916,626 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,485 Sq Ft

  2165 Gulf of Mexico Dr Unit 125, Longboat Key, FL 34228

  2165 Gulf of Mexico Dr Unit 125, Longboat Key, FL 34228
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  /28

  $395,000

  • 2 Beds
  • 2 Baths
  • 1,357 Sq Ft

  620 Spanish Dr N, Longboat Key, FL 34228

  Don't miss this rare opportunity to own a renovated standalone villa with a lake view on Longboat Key! This very light, bright, and charming 2 bedroom 2 bath home is almost ready for occupancy at an exceptionally low price. As you enter the home, you can see a lovely lake view through the large back windows. The rear, shady, landscaped patio is a perfect place to relax throughout the day and

  Adrienne Scott MICHAEL SAUNDERS & COMPANY

  620 Spanish Dr N, Longboat Key, FL 34228
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  /100

  $8,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,424 Sq Ft
  • House for Rent

  2369 Harbour Oaks Dr, Longboat Key, FL 34228

  LIVE THE LIFE ON LONGBOAT KEY...in this three bedroom, two-and-a-half bathroom villa in the BAY ISLES gated community. Open floor plan, with vaulted ceilings, hardwood floors throughout. Private screened in pool with a view of the golf course and evening sunsets with plenty of space for entertaining. Kitchen is equipped with everything a cook would need including a separate wet bar with a

  Teresa Ribaudo JENNETTE PROPERTIES INC

  2369 Harbour Oaks Dr, Longboat Key, FL 34228
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  /2

  $250,000 Sold Jul 14, 2025

  • 1,361 Sq Ft
  • $184/SF
  • 20 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  683 Spanish Dr S Unit 214, Longboat Key, FL 34228

  Coastal Living at Its Finest! Located in the highly sought-after Spanish Main Yacht Club, this 2-bedroom, 2-bath villa offers 1,361 sq ft under air (1,677 total sq ft) and is ready for rebuild after the storm—a perfect opportunity to customize your dream home in one of Longboat Key’s premier 55+ waterfront communities.Enjoy a spacious, light-filled open floor plan with a generous primary

  Geoff Scalera AUM FLORIDA REAL ESTATE LLC

  683 Spanish Dr S Unit 214, Longboat Key, FL 34228
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  /34

  Est $438,751 Not Listed For Sale

  641 Broadway St, Longboat Key, FL 34228

  641 Broadway St, Longboat Key, FL 34228
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  /30

  $249,000

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft

  3710 Gulf of Mexico Dr Unit A20, Longboat Key, FL 34228

  JUST STEPS FROM THE BEACH and FULLY FURNISHED! Discover this exceptional property located just one block from the shoreline. This charming one-bedroom, one-bath residence offers a spacious OPEN-CONCEPT living area and direct PRIVATE BEACH ACCESS. Perfectly positioned for easy access to GULF OF AMERICA, watch the sunrise over the bay and sunset over the ocean. Enjoy resort-style amenities in this

  Ruth Santana SANTANA AND COMPANY REAL ESTATE

  3710 Gulf of Mexico Dr Unit A20, Longboat Key, FL 34228
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  /31

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,409 Sq Ft
  • Condo for Rent

  1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228

  AVAILABLE OFF SEASON RENTAL JULY 1, 2025 THROUGH NOVEMBER 30, 2025 AT $5000 A MONTH AND SEASONAL JANUARY 2026 THROUGH APRIL 30, 2026 through MAY 30, 2026 Located the furthest South Behind The Gates of Longboat Key Club. Privateer North Complex located o Gulf of Mexico. Only a few steps to the beach. This 2 bedroom 2 bath residence has everything you need. Beautiful full Bay from this 8th floor

  Marni Hayden CHROME REALTY LLC

  1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
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  /2

  $1,700,000 Sold Jul 14, 2025

  • 1,842 Sq Ft
  • $923/SF
  • 132 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1984

  775 Longboat Club Rd Unit 902, Longboat Key, FL 34228

  Nestled within the gates of the exclusive Longboat Key Club, this fully furnished move in tomorrow 9th-floor corner condo offers sweeping panoramic views from the Gulf of Mexico to Sarasota Bay, making it an unparalleled beachfront retreat. With three generously sized bedroom suites and three beautifully appointed bathrooms, this luxury residence offers the perfect blend of comfort and

  Courtney Tarantino COLDWELL BANKER REALTY

  775 Longboat Club Rd Unit 902, Longboat Key, FL 34228
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  /53

  Est $845,860 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  Unlisted Address

  Unlisted Address
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  /60

  $365,000 Open Sun 1PM - 3PM

  • 1 Bed
  • 1 Bath
  • 837 Sq Ft

  4390 Exeter Dr Unit 104, Longboat Key, FL 34228

  Waterfront Paradise – Move-In Ready 1-Bedroom Condo with Income Potential .Live the dream in this beautifully furnished, move-in ready one-bedroom condo located in a premier waterfront community on Longboat Key . From the moment you step inside, you’re greeted with tasteful coastal décor, a bright and airy layout, and water views of the harbor through your fully enclosed lanai. Slide open the

  Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4390 Exeter Dr Unit 104, Longboat Key, FL 34228
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  /24

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • Condo for Rent

  1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228

  Available 07/15/2025 through 12/30/2025. LEASED SEASON JAN, 2026 THROUGH MARCH, 2026. This residence is gulf and bay views through your hurricane sliding doors and a view from every room. Pristine sandy beaches from a luxurious direct front gulf complex. Located in the gated Longboat Key club and Resort. A spacious 2 bedroom, 2 bathroom unit turn-key furnished. Both bedrooms have private lanais,

  Marni Hayden CHROME REALTY LLC

  1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
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  /2

  $2,700,000 Sold Jul 14, 2025

  • 4,127 Sq Ft
  • $654/SF
  • 255 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2000

  549 Sloop Ln, Longboat Key, FL 34228

  Experience unparalleled luxury and elegance at this prestigious Country Club Shores residence, nestled on the sought-after south end of Longboat Key. Designed by renowned architect and interior designer George Merlin.

  Tracey Stetler COLDWELL BANKER REALTY

  549 Sloop Ln, Longboat Key, FL 34228
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  /63

  Est $1,510,239 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,530 Sq Ft

  621 Buttonwood Dr, Longboat Key, FL 34228

  621 Buttonwood Dr, Longboat Key, FL 34228
• 

  

  /43

  $899,000

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft

  2045 Gulf of Mexico Dr Unit M1505, Longboat Key, FL 34228

  Fully RE-DESIGNED and RENOVATED 2-bedroom, 2-bath condo in Seaplace with PARTIAL GULF VIEWS. Completed in 2023, this residence showcases over $200K in UPSCALE UPGRADES AND FINISHES. Crafted for both elegance and durability, the home features HURRICANE IMPACT-rated windows and sliding glass doors, providing enhanced storm protection, improved energy efficiency, and year-round peace of mind. The

  Lee Mirman INVESTMENTS IN SARASOTA

  2045 Gulf of Mexico Dr Unit M1505, Longboat Key, FL 34228
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  /42

  $12,000 per month

  • 3 Beds
  • 3 Baths
  • 2,698 Sq Ft
  • Condo for Rent

  1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228

  LONGBOAT KEY'S SEAPLACE Enjoy the tropical sea breezes and the magical Water Views from this custom designed THREE BEDROOM spacious corner unit. Beautiful wrap around Lanai terraces with panoramic scenery of the GULF OF MEXICO. Primary Suite-King Bed, Bedroom #2 Suite-King Bed, Bedroom #3- two twin beds. Seaplace is located close to shopping and restaurants and just minutes to ST Armand's Circle

  Jane Hunter JENNETTE PROPERTIES INC

  1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
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  /2

  $3,300,000 Sold Jul 11, 2025

  • 3,710 Sq Ft
  • $889/SF
  • 335 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1977

  750 Penfield St, Longboat Key, FL 34228

  Nestled in the North Longboat Key area, this stunning five-bedroom home rebuilt in 2014 with new pool and many other features offers unparalleled luxury and breathtaking views. As you step through the sliding glass doors from the main living area to the terrace, you are greeted by the expansive vistas of Sarasota Bay and the Intercoastal Waterway. This property is an epitome of modern elegance,

  Reid Murphy DEVELOPERS REALTY LBK, INC

  750 Penfield St, Longboat Key, FL 34228
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  /61

  Est $1,111,527 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,465 Sq Ft

  3115 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  3115 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /66

  $2,000,000

  • 3 Beds
  • 2 Baths
  • 2,028 Sq Ft

  524 Ketch Ln, Longboat Key, FL 34228

  Discover the quintessential Longboat Key lifestyle in this classic masonry beach home located just “3” properties in from Sarasota Bay. Boasting 110 feet of canal frontage, your own private dock, a 7,500 lb. boatlift to complement this classic waterfront treasure it offers direct access for boating, fishing, and kayaking, with frequent visits from playful manatees and dolphins right in your

  Kathy Callahan MICHAEL SAUNDERS & COMPANY

  524 Ketch Ln, Longboat Key, FL 34228
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  /75

  $11,550 per month

  • 2 Beds
  • 2 Baths
  • 1,657 Sq Ft
  • House for Rent

  500 Schooner Ln, Longboat Key, FL 34228

  Booked May 1st- June 16th, July13th-July 27th, Nov 14th-rest of 2025. Booked January, May, October, and Dec 2026 through February 2027, Must be a one month minimum stay during seasonal months and 2 week minimum stay out of season. Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Every detail was

  Jennifer LeBlanc PRECISE REALTY CORP

  500 Schooner Ln, Longboat Key, FL 34228
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  /2

  $925,000 Sold Jul 10, 2025

  • 1,624 Sq Ft
  • $570/SF
  • 25 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  5055 Gulf of Mexico Dr Unit 232, Longboat Key, FL 34228

  Discover the epitome of coastal beachfront living with unparalleled gulf views in this beautifully renovated turnkey top-floor, corner-unit condominium with two bedrooms, two baths plus office/den that could become a third bedroom, in the sought-after Club Longboat Beach and Tennis Condos. Offered fully furnished, this exquisite residence boasts floor-to-ceiling sliding glass doors in the living

  Nathan Mathers PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5055 Gulf of Mexico Dr Unit 232, Longboat Key, FL 34228
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  /45

  Est $1,076,528 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,314 Sq Ft

  4401 Gulf of Mexico Dr Unit 807, Longboat Key, FL 34228

  4401 Gulf of Mexico Dr Unit 807, Longboat Key, FL 34228
• 

  

  /41

  $729,000 Open Sun 1PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft

  2301 Gulf of Mexico Dr Unit 45, Longboat Key, FL 34228

  Coastal Elegance on Longboat Key – Assessments Paid in Full!Beachfront Living RedefinedWelcome to an extraordinary beachfront retreat where the serene rhythm of the Gulf meets refined island living. This beautifully appointed two-bedroom, two-bath residence offersbeautiful views of the common grounds, entrance and tennis courts.A rare gem among beachfront properties, this home

  Paul Bachmann PREFERRED SHORE LLC

  2301 Gulf of Mexico Dr Unit 45, Longboat Key, FL 34228
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  /55

  $11,900 per month

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • Condo for Rent

  2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228

  Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you step into this fourteen-floor residence at Sea Gate, you will be captivated by the breathtaking views from every room.Relax on the lanai with new glass railings and enjoy your morning coffee while you plan your daily adventures. This beautifully renovated two-bedroom,

  Andrey markov ANMARK REALTY LLC

  2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
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  /2

  $357,000 Sold Jul 09, 2025

  • 837 Sq Ft
  • $427/SF
  • 26 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1970

  4420 Exeter Dr Unit 104, Longboat Key, FL 34228

  Spectacular water views of open Sarasota Bay from the front door of this fully furnished/turnkey, one bedroom, one bath walk out home on the first floor. The water view is amazing and must be seen to be appreciated. Enjoy reading or just relaxing from your living room watching the birds, dolphin, manatee or fish jump right outside your door. Bedroom and kitchen windows replaced in 2014 with

  Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4420 Exeter Dr Unit 104, Longboat Key, FL 34228
• 

  

  /28

  Est $2,826,850 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,045 Sq Ft

  1241 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228

  1241 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228
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  /44

  $675,000

  • 2 Beds
  • 2.5 Baths
  • 1,590 Sq Ft

  1912 Harbourside Dr Unit 602, Longboat Key, FL 34228

  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 Key via a private beach club, and an abundance of activities, including biking, recreation, pickleball and tennis, ideal for those who embrace an active

  Judy Mitchell PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1912 Harbourside Dr Unit 602, Longboat Key, FL 34228
• 

  

  /55

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,133 Sq Ft
  • Condo for Rent

  3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

  Welcome to Sunset On The Gulf! This gorgeous 2-bedroom, 2-bathroom, third-floor, corner condo offers the perfect location. Located between the bay and the beach, you are bound to have endless adventures. The community of Beach Harbor Club offers resort-style living at its finest. There is a large community pool, a clubhouse with a bar, and a fitness center to get in your morning exercises! You

  Andy Moore GULF COAST REALTY & MANAGEMENT

  3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
• 

  /2

  $850,000 Sold Jul 07, 2025

  • 2,550 Sq Ft
  • $333/SF
  • 2 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1988

  2120 Harbourside Dr Unit 621, Longboat Key, FL 34228

  This beautifully updated three-bedroom, 3.5-bath residence in the sought-after Atrium at Bay Isles on Longboat Key offers panoramic views of Sarasota Bay. The spacious living room opens to an expansive lanai through a four-panel sliding glass door, ideal for seamless indoor-outdoor living. The contemporary kitchen is equipped with stainless steel appliances, granite countertops, abundant

  Judy Mitchell PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2120 Harbourside Dr Unit 621, Longboat Key, FL 34228
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  /67

  Est $1,504,266 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,724 Sq Ft

  3637 Fair Oaks Place Unit 1, Longboat Key, FL 34228

  3637 Fair Oaks Place Unit 1, Longboat Key, FL 34228

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