Longboat Key, FL Homes

• 

  

  

  /57

  $675,000

  • 2 Beds
  • 2 Baths
  • 1,624 Sq Ft

  5055 Gulf of Mexico Dr Unit 414, Longboat Key, FL 34228

  Coastal Living Meets Resort-Style Amenities in this rarely available first floor Turnkey 2BR/3BR Condo by the Beach ( parking spot directly in front of the entrance door.) Step into the ultimate beachside retreat with this beautifully maintained 2 /3-bedroom, 2-bathroom condominium just steps from the shoreline. Whether you’re looking for a personal paradise or a high-potential investment

  Amy Jones COASTAL KEY REALTY LLC

  5055 Gulf of Mexico Dr Unit 414, Longboat Key, FL 34228
• 

  

  

  /38

  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 1,168 Sq Ft
  • House for Rent

  4780 Gulf of Mexico Dr, Longboat Key, FL 34228

  This immaculate 2-bedroom, 2-bath ground-floor villa located in the highly sought-out community of Windward Bay has peek-a-boo views of the Gulf. Turnkey furnished with one carport at your front door. The community of Windward Bay is pristine. There is private deeded beach access just across the street, two public beach access, two marinas BBQ grills, 1/2 mile of walking trails, two heated pools,

  Joseph Stephens ONE STEP AHEAD REALTY INC

  4780 Gulf of Mexico Dr, Longboat Key, FL 34228
• 

  

  /2

  $2,050,000 Sold Mar 27, 2025

  • 2,135 Sq Ft
  • $960/SF
  • 20 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1966

  524 Gunwale Ln, Longboat Key, FL 34228

  Southern exposure! This remodeled soft contemporary 3-bedroom home embodies refined taste and gracious living, offering a perfect blend of Florida elegance and functionality. The impeccable open design showcases captivating views from nearly every room, complemented by effortless living with travertine flooring and a fabulous entry foyer. The kitchen, a chef's delight, features granite

  Judy Kepecz-Hays COLDWELL BANKER REALTY

  524 Gunwale Ln, Longboat Key, FL 34228
• 

  

  

  /18

  Est $240,529 Not Listed For Sale

  • Studio
  • 1,155 Sq Ft

  2600 Harbourside Dr Unit C-10, Longboat Key, FL 34228

  2600 Harbourside Dr Unit C-10, Longboat Key, FL 34228
• 

  

  

  /37

  $300,000

  2600 Harbourside Dr Unit C-12, Longboat Key, FL 34228

  An extraordinary opportunity to own a 55-by-21-foot yacht slip at Longboat Key Moorings, one of Florida’s finest deep-water marinas, on the exclusive island of Longboat Key. This state-of-the-art marina offers direct, no-bridge access to Sarasota Bay and Intracoastal Waterway, just minutes from the Gulf of Mexico. Ideally situated, Longboat Key Moorings is only moments from the upscale boutiques

  Jessica Hurley PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2600 Harbourside Dr Unit C-12, Longboat Key, FL 34228
• 

  

  /39

  $10,500 per month

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft
  • Condo for Rent

  4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228

  **BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease JANUARY through MARCH 2026 with the option to include APRIL 2026** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath

  Norma Mladineo COLDWELL BANKER REALTY

  4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
• 

  /2

  $4,000,000 Sold Mar 25, 2025

  • 3,926 Sq Ft
  • $1019/SF
  • 57 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2024

  3480 Bayou Sound, Longboat Key, FL 34228

  Step into a world of unparalleled luxury and coastal elegance with this brand new coastal contemporary masterpiece in the exclusive double gated and secure Bay Isles community of Bayou Sound. Designed with impeccable attention to detail, this home offers a seamless blend of sophistication and comfort. The custom chef’s kitchen is a true showstopper, featuring bespoke cabinetry, top-of-the-line

  Nicholle McKiernan COLDWELL BANKER REALTY

  3480 Bayou Sound, Longboat Key, FL 34228
• 

  

  /36

  Est $927,361 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 739 Sq Ft

  240 Sands Point Rd Unit 4401, Longboat Key, FL 34228

  240 Sands Point Rd Unit 4401, Longboat Key, FL 34228
• 

  

  /90

  $588,000

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  4380 Exeter Dr Unit 202, Longboat Key, FL 34228

  $5000 Credit to Buyer at closing with an acceptable contract closing by May 15, 2025. Looking for your piece of paradise on the Suncoast of Florida? Don't miss the opportunity to own in the coveted beach to bay gated community of Longboat Harbour on world famous Longboat Key. Perfect for full time or seasonal residents and investors, take the elevator to this second floor two-bedroom two bath

  Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4380 Exeter Dr Unit 202, Longboat Key, FL 34228
• 

  

  /35

  $8,500 per month

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Condo for Rent

  4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

  BEAUTIFULLY RENOVATED VACATION RENTAL: Stunning Gulf views and incredible sunsets await you from this JUST completely renovated 2 bedroom, 2 bath condo on Longboat Key. You’ll fall in love with the contemporary soft-palette, coastal style! The open layout offers a seamless blend of kitchen, dining and living space, perfect for entertaining and relaxing. The gourmet kitchen features

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
• 

  /2

  $1,240,000 Sold Mar 24, 2025

  • 1,748 Sq Ft
  • $709/SF
  • 29 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1982

  1918 Harbourside Dr Unit 902, Longboat Key, FL 34228

  Ladies and gentlemen, prepare to be utterly enchanted by this splendidly refurbished, fully furnished residence, nestled within the esteemed Fairway Bay community at Bay Isles on Longboat Key. This two-bedroom, two-and-a-half bath gem is the epitome of turnkey elegance, and eagerly awaits your arrival. Dare I say, it is the most exquisite two-bedroom townhome in the entire 14-building enclave.

  Jason Moore MICHAEL SAUNDERS & COMPANY

  1918 Harbourside Dr Unit 902, Longboat Key, FL 34228
• 

  

  /48

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft

  210 Sands Point Rd Unit 2603/04, Longboat Key, FL 34228

  210 Sands Point Rd Unit 2603/04, Longboat Key, FL 34228
• 

  

  /92

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,208 Sq Ft

  600 Sutton Place Unit 305, Longboat Key, FL 34228

  Immerse yourself in breathtaking panoramic bay views from this beautifully curated end-unit 2-bedroom coastal retreat. Filled with natural light and embraced by serene harbor waters, this radiant oasis perfectly captures the essence of relaxed seaside living. Enjoy the privilege of private deeded beach access, two sparkling resort-style pools, a friendly clubhouse, and marina—all nestled within a

  Malihe Karimi MICHAEL SAUNDERS & COMPANY

  600 Sutton Place Unit 305, Longboat Key, FL 34228
• 

  

  /49

  $3,750 per month

  • 2 Beds
  • 2 Baths
  • 1,175 Sq Ft
  • Condo for Rent

  3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  Escape to this 2-bed, 2-bath penthouse paradise at Beach Harbor Club. The penthouse features more spacious living and dining areas with stunning Gulf views. The unit includes an outside patio, as well as a washer/dryer. Beach Harbor Club is a beach to bay community and has a bundle of awesome amenities. Enjoy exclusive beach access, complete with grills, showers, and beach/lounge chairs. Take a

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
• 

  /2

  $715,000 Sold Mar 24, 2025

  • 2,001 Sq Ft
  • $357/SF
  • 62 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1982

  1912 Harbourside Dr Unit 603, Longboat Key, FL 34228

  Your move-in ready island getaway awaits. This Fairway Bay townhome is beautifully furnished and fully renovated, offering generous views of the tropical landscaping, and featuring exclusive access to the Bay Isles beach club. Located in the gated community of Bay Isles, Fairway Bay offers an amenity-rich lifestyle, a heated resort-style pool and spa, fitness center, tennis and pickleball

  Mike Seamon PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1912 Harbourside Dr Unit 603, Longboat Key, FL 34228
• 

  

  /64

  Est $1,491,838 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,548 Sq Ft

  1465 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  1465 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
• 

  

  /42

  $975,000

  • 2 Beds
  • 2 Baths
  • 1,509 Sq Ft

  615 Dream Island Place Unit 303, Longboat Key, FL 34228

  Welcome to Water Song, your slice of paradise at Harbour Villa Club in prestigious Longboat Key! Water Song is a beautifully maintained top-floor condo with breathtaking water views from nearly every room. Wake up to shimmering water views from your master bedroom and enjoy your morning coffee on the enclosed lanai (216 Sq Ft lanai). Located on the top floor, this two bedroom/ two bath

  Remi Drigan SATO REAL ESTATE INC.

  615 Dream Island Place Unit 303, Longboat Key, FL 34228
• 

  

  /41

  $11,800 per month

  • 2 Beds
  • 2.5 Baths
  • 1,484 Sq Ft
  • Condo for Rent

  4325 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228

  AVAILABLE JANUARY & FEBRUARY 2025. 2 bedroom 2 bath with office. Enjoy fantastic gulf views from your private lanai, living room, kitchen and master bedroom. Many upgrades have already been very tastefully made to this residence. Unit fitted with electric hurricane shutters, tankless hot water heater, sound system in every room, darkening shades and solar shades in master bedroom plus

  Brenda Cozy COLDWELL BANKER REALTY

  4325 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
• 

  /2

  $217,000 Sold Mar 21, 2025

  • 1,088 Sq Ft
  • $199/SF
  • 9 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1966

  713 Saint Judes Dr S Unit 1, Longboat Key, FL 34228

  2B/2B WATERFRONT CONDO on Longboat Key! Here's your rare chance to own a waterfront property with direct access to the Inter-coastal Waterway and 40 feet of water frontage, suitable for a private dock. The property has experienced substantial flood damage and offers a blank canvas for you to re-imagine and create your dream waterfront retreat. NEW METAL ROOF with clips and 3rd nail in 2016.

  Cindy Quinn SATO REAL ESTATE INC.

  713 Saint Judes Dr S Unit 1, Longboat Key, FL 34228
• 

  

  /32

  Est $956,735 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft

  240 Sands Point Rd Unit 4102, Longboat Key, FL 34228

  240 Sands Point Rd Unit 4102, Longboat Key, FL 34228
• 

  

  /79

  $4,195,000

  • 3 Beds
  • 3.5 Baths
  • 3,564 Sq Ft

  675 Longboat Club Rd Unit 23A, Longboat Key, FL 34228

  Spectacular Gulf front location! Rarely available A floorpan Three bedroom, three bath direct beach corner residence with southern exposure with vistas to the beach, azure Gulf waters and sunsets plus views of the Longboat key Club golf course, Sarasota Bay and downtown Sarasota lights. Sunrise, sunsets are all enjoyed from this third floor spacious, open floor plan. A private, secured elevator

  Reid Murphy DEVELOPERS REALTY LBK, INC

  675 Longboat Club Rd Unit 23A, Longboat Key, FL 34228
• 

  

  /77

  $8,000 per month

  • 2 Beds
  • 2 Baths
  • 928 Sq Ft
  • Condo for Rent

  1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228

  AVAILABLE FOR 2026 SEASON! MINIMUM 3 MONTH LEASE PLEASE. LUXURIOUS, RESORT STYLE, 2BR/2B CONDO LOCATED IN THE HIGHLY SOUGHT AFTER SEAPLACE COMMUNITY ON LONGBOAT KEY. This gorgeous 4th floor condo comes turnkey furnished and located only three miles north of St. Armand's circle. When you walk in you will be blown away by the light, bright and open feeling the condo has to give with the natural

  Brigette Marcus NEXTHOME EXCELLENCE

  1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
• 

  /2

  $775,000 Sold Mar 21, 2025

  • 1,442 Sq Ft
  • $537/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1982

  1930 Harbourside Dr Unit 117, Longboat Key, FL 34228

  STUNNER ALERT- WITH OFFICE SPACE-DON’T PASS THIS BY JUST BECAUSE IT SAYS 2BED/2BATH! This end unit with an oversized walk-down bayfront terrace, and also an additional side terrace, exudes updated elegant comfort with the spanning water view everyone dreams of! The open floor plan combines kitchen/ living/ dining and outdoor spaces and has the office tucked away in the back to keep work space

  Cindy Schatzle COLDWELL BANKER REALTY

  1930 Harbourside Dr Unit 117, Longboat Key, FL 34228
• 

  

  /42

  Est $844,105 Not Listed For Sale

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

  1085 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  1085 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
• 

  

  /64

  $3,295,000

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

  1241 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228

  Welcome to this spectacular three bedroom 6th floor southern facing Brighton floor plan located in the south building of the sensational Gulf front Water Club complex on south Longboat Key. Your private elevator opens directly into the foyer which leads to the open floorplan and the sensational views of sandy beach and the Gulf of Mexico. The condo features beautiful wood floors, a gourmet

  Reid Murphy DEVELOPERS REALTY LBK, INC

  1241 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
• 

  

  /30

  $10,000 per month

  • 3 Beds
  • 2 Baths
  • 1,454 Sq Ft
  • House for Rent

  6979 Longboat Dr S, Longboat Key, FL 34228

  This stunning property on Longboat Key is a true garden oasis, with butterflies fluttering around the lush landscaping and a private heated pool to relax in. The spacious lanai is perfect for al fresco dining, and the fully renovated kitchen boasts top-of-the-line appliances including a Wolf stove. The bedrooms and bathrooms have also been beautifully updated, with a brand new king-size bed in

  Rinat Sikdar COLDWELL BANKER REALTY

  6979 Longboat Dr S, Longboat Key, FL 34228
• 

  /2

  $1,800,000 Sold Mar 21, 2025

  • 1,823 Sq Ft
  • $987/SF
  • 29 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1990

  575 Sanctuary Dr Unit A201, Longboat Key, FL 34228

  Direct gulf front 3 bedroom, 2 1/2 bath condo on south Longboat Key behind the gates of the exclusive Longboat Key Club. Enjoy breathtaking Gulf of Mexico views and stunning sunsets from walls of glass in every room. Owners will enjoy the spacious wraparound balcony accessed from the kitchen, the main living area and the guest bedroom. The primary suite offers two walk-in closets, a vanity area,

  Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  575 Sanctuary Dr Unit A201, Longboat Key, FL 34228
• 

  

  /19

  Est $212,084 Not Listed For Sale

  • Studio
  • 1,155 Sq Ft

  2800 Harbourside Dr Unit E-06, Longboat Key, FL 34228

  2800 Harbourside Dr Unit E-06, Longboat Key, FL 34228
• 

  

  /19

  $425,000

  2600 Harbourside Dr Unit L-03, Longboat Key, FL 34228

  Ask an L-dock boater, they will tell you its the best dock in the marina. Slip is near the seawall with easy in/out access. A 68 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit L-03, Longboat Key, FL 34228
• 

  

  /49

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft
  • Condo for Rent

  4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Furnished beachfront vacation rental!This spacious (1336 sq ft + balcony) condo is a luxurious living space that offers breathtaking panoramic views of the beach, sunset, and Gulf of Mexico. It is located in a smaller building, on an uncrowded segment of beach that can often be enjoyed in complete solitude.The unit was recently upgraded with a new washer/dryer, luxury vinyl

  Daniel Goldman COMPASS FLORIDA LLC

  4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
• 

  /2

  $2,000,000 Sold Mar 21, 2025

  • 3,045 Sq Ft
  • $657/SF
  • 95 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1996

  1241 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  Welcome to this spectacular three bedroom 3rd floor Brighton floor plan located in the south building of the sensational Gulf front Water Club complex on south Longboat Key. Your private elevator opens directly into the foyer which leads to the open floorplan and the sensational views of sandy beach and the Gulf of Mexico. The condo features beautiful wood floors, a gourmet kitchen with high end

  Reid Murphy DEVELOPERS REALTY LBK, INC

  1241 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
• 

  

  /18

  Est $376,128 Not Listed For Sale

  • Studio

  2600 Harbourside Dr Unit L-08, Longboat Key, FL 34228

  2600 Harbourside Dr Unit L-08, Longboat Key, FL 34228
• 

  

  /42

  $519,900

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  605 Sutton Place Unit 102, Longboat Key, FL 34228

  All You Need is your Bathing Suit! Your Gulf-to-Bay Condo in the Desired Community of Sutton Place in Longboat Key is TURNKEY, and ready for you to just move in. Everything included in the sale - even the Washer and Dryer in the home - a bonus, as not all units have laundry inside. This beautiful, 1st Floor, open floor plan is full of natural light from the sliding glass doors that open up and

  Amy Conrad XCELLENCE REALTY, INC

  605 Sutton Place Unit 102, Longboat Key, FL 34228
• 

  

  /14

  $6,000 per month

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

  3240 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

  PORTOBELLO - SHORT TERM RENTAL - 2 Bedrooms, 2 Baths in the #1 Beach of Florida, white quartz sand and dreamy sunsets Ample and chic apartment fully furnished to enjoy vacation time. 2 Parking spots

  Valeria Fucaraccio Benesch Brokers, LLC

  3240 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
• 

  /2

  $545,000 Sold Mar 19, 2025

  • 1,361 Sq Ft
  • $400/SF
  • 42 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  3810 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  This move-in-ready, turn-key furnished penthouse unit invites you to embrace the ultimate coastal lifestyle! Enjoy beachside living, boating adventures, and complimentary sunrises and sunsets from your stunning Beach Harbor Club condo. Rarely available and beautifully updated, this condo is a true treasure. Nearly every room boasts picturesque bay views. The thoughtfully designed kitchen is a

  Susan Mondello MICHAEL SAUNDERS & COMPANY

  3810 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
• 

  

  /28

  Est $1,178,937 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft

  1125 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228

  1125 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
• 

  

  /23

  $825,000

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft

  4835 Gulf of Mexico Dr Unit 106, Longboat Key, FL 34228

  Year after year, The Westchester has been considered to be the most sought after location on Gulf of Mexico Drive. This two bedroom, two bath 1,393 sq. ft. condo holds many happy family memories, which could now be yours. Experience the beautiful views of the Emerald waters from both lanais. Unit has recently been completely painted and professionally cleaned, with newly installed flooring.

  Toni Giliberti COLDWELL BANKER REALTY

  4835 Gulf of Mexico Dr Unit 106, Longboat Key, FL 34228
• 

  

  /22

  $3,700 per month

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

  3235 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  PORTOBELLO - BEACH FRONT Elevate your quality life, Working from home? Retired? relax and enjoy this wonderful two bedrooms, two full baths apartment in front of the #1 beach in Florida, white quartz sands and dreamy sunsets. 2 Parking spots.

  Valeria Fucaraccio Benesch Brokers, LLC

  3235 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
• 

  /2

  $2,200,000 Sold Mar 19, 2025

  • 3,684 Sq Ft
  • $597/SF
  • 67 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1990

  3161 Bayou Sound, Longboat Key, FL 34228

  This stunning 4-bedroom home, located on the tranquil Bay Isles Waterway, offers a luxurious lifestyle within the popular Bayou neighborhood of the Longboat Key Club. With a thoughtfully designed open floor plan, the home features high ceilings and expansive glass walls that allow natural light to flood the space, creating a bright and inviting atmosphere. The modern kitchen seamlessly flows into

  Linda Weber COLDWELL BANKER REALTY

  3161 Bayou Sound, Longboat Key, FL 34228
• 

  

  /48

  Est $1,022,295 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,366 Sq Ft

  1485 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  1485 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

Showing Results 241 - 280, Page 7 of 18