Longboat Key, FL Homes

• 

  

  

  /75

  $485,000

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  4380 Exeter Dr Unit 304, Longboat Key, FL 34228

  Experience the best of waterfront living on beautiful Longboat Key! This light-filled, meticulously maintained 2-bedroom, 2-bath condo offers sweeping views of the harbor on Sarasota Bay, creating a serene backdrop for your beach to bay life style. Located in the sought-after Longboat Harbour community, this residence features an open floor plan, an updated kitchen with modern appliances,

  Brett Keyser, Jr RE/MAX ALLIANCE GROUP

  4380 Exeter Dr Unit 304, Longboat Key, FL 34228
• 

  

  

  /57

  $7,500 per month

  • 3 Beds
  • 2 Baths
  • 1,962 Sq Ft
  • House for Rent

  990 Bogey Ln, Longboat Key, FL 34228

  Introducing a charming 3-bedroom, 2-bathroom single family home located in the prestigious Country Club Shores of Longboat Key, FL. This fully furnished property boasts deeded beach access, perfect for enjoying the sun and surf just steps away from your front door. The fenced backyard provides privacy and a great space for outdoor entertaining. Situated just 2.8 miles from the vibrant St. Armands

  Ray Shope ROSEBAY INTERNATIONAL REALTY, INC

  990 Bogey Ln, Longboat Key, FL 34228
• 

  

  /2

  $3,575,000 Sold Mar 31, 2025

  • 3,115 Sq Ft
  • $1148/SF
  • 17 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1991

  545 Sanctuary Dr Unit B504, Longboat Key, FL 34228

  Welcome to a slice of paradise at The Sanctuary, where coastal living meets luxurious comfort. Apartment 504 presents an unparalleled opportunity to own an exquisite residence in one of Longboat Key's most prestigious communities. As you enter the large hallway immerse yourself in breathtaking direct views of the Gulf of Mexico meeting the pristine Longboat key beach and enjoy awe-inspiring

  Melanie Russell QUEST PROPERTIES INC

  545 Sanctuary Dr Unit B504, Longboat Key, FL 34228
• 

  

  

  /64

  Not Listed For Sale

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

  2295 Gulf of Mexico Dr Unit 112, Longboat Key, FL 34228

  2295 Gulf of Mexico Dr Unit 112, Longboat Key, FL 34228
• 

  

  

  /84

  $1,749,000

  • 3 Beds
  • 2.5 Baths
  • 3,080 Sq Ft

  2450 Harbourside Dr Unit 233, Longboat Key, FL 34228

  Enjoy stunning, unobstructed views of Sarasota Bay, the city skyline, and the Longboat Key Club Harbourside Golf Course from this remarkable residence that lives like a single-family home—offered at an exceptional value. Located behind the 24-hour manned gates of the Longboat Key Club, this home is ideally situated close to club amenities and just moments from the Bay Isles Beach Club on the

  Linda Weber COLDWELL BANKER REALTY

  2450 Harbourside Dr Unit 233, Longboat Key, FL 34228
• 

  

  /32

  $5,500 per month

  • 2 Beds
  • 2.5 Baths
  • 1,626 Sq Ft
  • Townhouse for Rent

  1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228

  Experience luxury and tranquility in this stunning unit at 1928 Harbourside Dr, Unit 1402, located within the Bay Isles community on Longboat Key. This residence offers a spacious layout designed for comfort and style, with access to top-tier amenities including a nearby marina, private golf course, swimming pool, and spa. Enjoy the privacy and security of this exclusive gated community, all just

  Alex Larchenko KELLER WILLIAMS ON THE WATER S

  1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228
• 

  /2

  $760,000 Sold Mar 28, 2025

  • 1,300 Sq Ft
  • $585/SF
  • 2 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  5393 Gulf of Mexico Dr Unit 216C, Longboat Key, FL 34228

  It's all about the VIEW. This 2-bedroom 2 bath condo is a clean canvas waiting for the creative buyer who will transform the interior into a sparkling, happy haven. There are full gulf views from the major rooms and the generously sized screen porch. Small bonus rooms off the kitchen and 2nd bedroom have multiple uses. This complex offers a clubhouse with a fitness room and a gulf side pool.

  Bobbie Banan MICHAEL SAUNDERS & COMPANY

  5393 Gulf of Mexico Dr Unit 216C, Longboat Key, FL 34228
• 

  

  /31

  Est $925,435 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 657 Sq Ft

  210 Sands Point Rd Unit 2302, Longboat Key, FL 34228

  210 Sands Point Rd Unit 2302, Longboat Key, FL 34228
• 

  

  /52

  $4,725,000

  • 4 Beds
  • 4.5 Baths
  • 4,438 Sq Ft

  524 Schooner Ln, Longboat Key, FL 34228

  Elegant Bayfront Living in Country Club ShoresDiscover timeless luxury in this custom-built 4,438 sq. ft. waterfront estate in coveted Country Club Shores. Perfectly positioned on an oversized lot with deep sailboat water and panoramic views of Sarasota Bay extending to the Ca’ d’Zan, this 2008 residence offers an extraordinary blend of craftsmanship, comfort, and coastal charm.Enter through

  Cathy Palmer DOUGLAS ELLIMAN

  524 Schooner Ln, Longboat Key, FL 34228
• 

  

  /34

  $5,500 per month

  • 2 Beds
  • 2.5 Baths
  • 1,590 Sq Ft
  • Condo for Rent

  2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228

  Welcome to 2012 Harbourside Dr, a beautifully located home within the Bay Isles community on Longboat Key. This spacious residence provides access to the best of Florida’s coastal lifestyle, including a nearby marina, private golf course, pool, and spa. Enjoy the serenity of this gated community, which offers privacy and proximity to the scenic Sarasota Bay. Just a short drive from the cultural

  Alex Larchenko KELLER WILLIAMS ON THE WATER S

  2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
• 

  /2

  $2,834,000 Sold Mar 28, 2025

  • 4,004 Sq Ft
  • $708/SF
  • 0 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2008

  3314 Bayou Rd, Longboat Key, FL 34228

  A stunning custom home where Coastal &Traditional merge into a true masterpiece. Lovingly remodeled and updated with high end finishes, spacious rooms, built-ins and high ceilings. All bathrooms are en-suite with additional powder bath. Custom kitchen with caesar stone counters and an abundance of cabinets, most with roll out shelves. Charming breakfast room. Natural gas cooktop burners, Jenn

  Debra Pitell-Hauge MICHAEL SAUNDERS & COMPANY

  3314 Bayou Rd, Longboat Key, FL 34228
• 

  

  /53

  Est $801,710 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 642 Sq Ft

  225 Sands Point Rd Unit 6106, Longboat Key, FL 34228

  225 Sands Point Rd Unit 6106, Longboat Key, FL 34228
• 

  

  /100

  $4,950,000

  • 4 Beds
  • 4.5 Baths
  • 3,925 Sq Ft

  581 Kingfisher Ln, Longboat Key, FL 34228

  Discover unparalleled luxury and design at 581 Kingfisher Lane, a 2019 masterpiece by Ross Built Construction, this like-new, move-in-ready home is ideally located in Longboat Key Estates, offering direct access to Sarasota Bay and just seven homes from the pristine Gulf beaches. This home combines the best of coastal beauty, modern design, and convenience, offering a perfect retreat for those

  Rich Polese COMPASS FLORIDA LLC

  581 Kingfisher Ln, Longboat Key, FL 34228
• 

  

  /32

  $3,900 per month

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

  3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228

  Here's an opportunity to become immersed in the laid back island lifestyle. Available for a six month rental starting late June through January, this nicely updated condo is located on the Bay side of popular Portobello with deeded beach access directly across the road. There's plenty of room for everyone to spread out in this fourth floor condo with an open, split floor plan and a screened lanai

  Rosemarie McKee COLDWELL BANKER REALTY

  3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228
• 

  /2

  $1,770,000 Sold Mar 27, 2025

  • 3,056 Sq Ft
  • $579/SF
  • 0 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2000

  2063 Harbour Links Dr Unit 6, Longboat Key, FL 34228

  Enjoy the ultimate Longboat Key lifestyle in this maintenance-free residence in sought-after Emerald Pointe North, a well-manicured community located behind the gates of Bay Isles on Longboat Key. This two-story home is framed by tropical and mature landscaping and paver walkway, which lead to the serene courtyard entryway where a verdant paradise with pond and soothing waterfall greets you. Your

  Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  2063 Harbour Links Dr Unit 6, Longboat Key, FL 34228
• 

  

  /31

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 621 Sq Ft

  3710 Gulf of Mexico Dr Unit C24, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit C24, Longboat Key, FL 34228
• 

  

  /82

  $2,495,000

  • 3 Beds
  • 3 Baths
  • 2,365 Sq Ft

  340 Gulf of Mexico Dr Unit 124, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Tangerine Bay Club, the most southern condominium on Longboat Key, refined sophistication, this stunning, one-of-a-kind direct Bayfront end residence has breathtaking panoramic Bay views. New roof, move in ready, lives like a single-family home, extensively updated kitchens and baths all with tasteful granite counters by previous owner. Spacious

  Debra Pitell-Hauge MICHAEL SAUNDERS & COMPANY

  340 Gulf of Mexico Dr Unit 124, Longboat Key, FL 34228
• 

  

  /30

  $7,000 per month

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

  4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

  SEASONAL/VACATION RENTAL! Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, large walk-in closets and covered parking. The Master suite features

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
• 

  /2

  $800,000 Sold Mar 27, 2025

  • 1,329 Sq Ft
  • $602/SF
  • 57 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1996

  3080 Grand Bay Blvd Unit 544, Longboat Key, FL 34228

  BREATHTAKING VIEWS UPON ENTERING- this Top floor condo situated in Grand Bay community of Bay Isles in Longboat Key has floor to ceiling sliders in EVERY room-taking in FULL water views on one side & golf course on other-all bringing in plenty of light! The essence of Florida living over Sarasota Bay-this center staged unit with multiple balconies lets you take in the gorgeous sunrises and off

  Joanna Petriccione-Teitelbaum KELLER WILLIAMS ON THE WATER S

  3080 Grand Bay Blvd Unit 544, Longboat Key, FL 34228
• 

  

  /8

  Est $610,511 Not Listed For Sale

  6800 Longboat Dr S, Longboat Key, FL 34228

  6800 Longboat Dr S, Longboat Key, FL 34228
• 

  

  /65

  $3,295,000

  • 3 Beds
  • 3.5 Baths
  • 2,880 Sq Ft

  340 Gulf of Mexico Dr Unit 136, Longboat Key, FL 34228

  Two-level penthouses at Tangerine Bay Club are a rare offering, and this south-facing corner residence elevates the standard. Recently reimagined with refined sophistication, this nearly 3,000-square-foot getaway captures breathtaking panoramic views of Sarasota Bay, the city skyline, and lush coastal mangroves. Perfectly situated to ensure ultimate privacy with two coveted terraces and peaceful

  Roger Pettingell COLDWELL BANKER REALTY

  340 Gulf of Mexico Dr Unit 136, Longboat Key, FL 34228
• 

  

  /30

  $11,700 per month

  • 2 Beds
  • 2 Baths
  • 1,474 Sq Ft
  • Condo for Rent

  448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228

  LONGBOAT KEY SOUTH...This is a 3 bedroom, 2 bathroom, end unit on the main floor which makes this unit light & bright with extra windows. The interior is decorated tastefully with warm neutral colors. Beautiful views of Sarasota Bay. Fully equipped kitchen which features stainless appliances, granite countertops and wood cabinets. There is a king size bed in the main bedroom and a queen bed in

  Teresa Ribaudo JENNETTE PROPERTIES INC

  448 Gulf of Mexico Dr Unit A106, 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
• 

  

  /33

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 880 Sq Ft

  3710 Gulf of Mexico Dr Unit G1, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit G1, Longboat Key, FL 34228
• 

  

  /77

  $649,000

  • 2 Beds
  • 2 Baths
  • 1,479 Sq Ft

  3540 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

  Spellbinding Sunrises, Sunsets, and magical water views from this nicely updated Bayfront Beauty in an ideal Mid-Key Bay to Beach setting can be yours now. Delight in the panoramic Bay to Gulf views from the moment you wake up until you turn in after a fun-filled day at the private beach, or after taking your boat, kayaks or paddleboards out to explore paradise. The spacious patio is the perfect

  Tina Rudek Stark, PA ROSEBAY INTERNATIONAL REALTY, INC

  3540 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
• 

  

  /68

  $3,300 per month

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

  4410 Exeter Dr Unit 204, Longboat Key, FL 34228

  **AVAILABLE AUGUST 2025-JANUARY 2026** THREE MONTH MINIMUM** LUXURY LONGBOAT LIVING AT IT’S FINEST! RESORT STYLE, 2BR/2B CONDO LOCATED IN THE HIGHLY SOUGHT AFTER LONGBOAT HARBOUR COMMUNITY ON LONGBOAT KEY. This gorgeous 2nd floor condo comes turnkey furnished and located a short distance from St. Armand’s circle. When you walk in you will be blow away by the light, bright and open feeling the

  Brigette Marcus NEXTHOME EXCELLENCE

  4410 Exeter Dr Unit 204, 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
• 

  

  /80

  Est $1,545,318 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,462 Sq Ft

  2020 Harbourside Dr Unit 434/435, Longboat Key, FL 34228

  2020 Harbourside Dr Unit 434/435, Longboat Key, FL 34228
• 

  

  /17

  $105,000

  • 2 Beds
  • 2 Baths
  • 852 Sq Ft

  73 Twin Shores Blvd, Longboat Key, FL 34228

  INCREDIBLE VALUE!! Here's your chance to own a slice of paradise at an unbeatable price. Listed well below land value due to damage from Hurricane Helene, this property offers amazing potential in a highly sought-after 55+ Beach-to-Bay community. Perfect for investors, snowbirds, or anyone ready to create their dream coastal retreat. Whether you bring in a new manufactured home or continue the

  Mary Moore WAGNER REALTY

  73 Twin Shores Blvd, Longboat Key, FL 34228
• 

  

  /20

  $10,000 per month

  • 2 Beds
  • 2 Baths
  • 1,896 Sq Ft
  • Condo for Rent

  2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  Available Now! Absolutely stunning waterfront turnkey furnished short term rental property on Longboat Key. This unit features beautiful sunsets daily from your private balcony and there is a shared seating area facing east if you prefer sunrises. This spacious 2/2 split floor plan has been fully renovated and is tastefully furnished. The property boasts amenities such as a beachfront pool,

  Christian Higgins ANDRE LECLAIR PROPERTIES LLC

  2675 Gulf of Mexico Dr Unit 302, 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
• 

  

  /29

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 693 Sq Ft

  3710 Gulf of Mexico Dr Unit E23, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit E23, Longboat Key, FL 34228
• 

  

  /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
• 

  

  /17

  $10,500 per month

  • 2 Beds
  • 2 Baths
  • 1,513 Sq Ft
  • Condo for Rent

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

  No damage to unit after storms. Call for rates and availability. Available December - April. One month minimum. Tremendous view of the Gulf from this Gulfside/Beachside 2 BR/2 B condo. Direct Gulf front unit. Breathtaking view of the pristine waters of the Gulf of Mexico. Sit on the balcony to your 7th floor unit. Take in the sunsets with your loved ones and friends. Just a couple minutes and

  William Glade WILLIAM GLADE LIC. REAL ESTATE BROKER

  2425 Gulf of Mexico Dr Unit 7F, 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 SOTHEBYS INTL REALTY

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

  

  /69

  Est $806,811 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,498 Sq Ft

  5270 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228

  5270 Gulf of Mexico Dr Unit 502, 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 SOTHEBYS INTL REALTY

  2600 Harbourside Dr Unit C-12, 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

  $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
• 

  

  /19

  Est $383,588 Not Listed For Sale

  • Studio

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

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

Showing Results 201 - 240, Page 6 of 18