Longboat Key, FL Homes

• 

  

  

  /94

  $5,999,000

  • 4 Beds
  • 4.5 Baths
  • 3,921 Sq Ft

  2251 Gulf of Mexico Dr Unit 301, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Are you ready to discover your very own private Gulf Oasis? Step into a slice of paradise at your dream coastal retreat located in the esteemed Aria community on Longboat Key's coveted south end. This serene haven is not just a residence; it offers an exclusive lifestyle filled with tranquility and easy access to the finest dining, arts, and

  

  Rachel Woodruff

  HOUSE MATCH

  (941) 368-4364

  2251 Gulf of Mexico Dr Unit 301, Longboat Key, FL 34228
• Explore Longboat Key

• 

  

  

  /87

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,601 Sq Ft
  • Condo for Rent

  817 Bayport Way Unit 817, Longboat Key, FL 34228

  STUNNING BAY VIEWS! Enjoy picturesque sunrises from your private deck in this tastefully decorated 2 bedroom, 2 bathroom furnished condominium. This home has an open concept floor plan which features an expansive Living/Dining/Kitchen area. The generous size master bedroom with adjoining bathroom includes a double vanity, separate shower, a walk-in closet and a small alcove that accommodates a

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 732-8949

  817 Bayport Way Unit 817, Longboat Key, FL 34228
• 

  $1,425,000 Sold Nov 26, 2025

  603 Longboat Club Rd Unit 1103N, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • Built 1970

  Last Sold Summary

  • 7% Below List Price
  • $977/SF
  • 11 Days On Market

  Last Listing Agent Irma Scherer COMPASS FLORIDA LLC

  603 Longboat Club Rd Unit 1103N, Longboat Key, FL 34228
• 

  

  /2

  Est $471,712 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  605 Sutton Place Unit 203, Longboat Key, FL 34228

  605 Sutton Place Unit 203, Longboat Key, FL 34228
• 

  

  

  /71

  $649,000

  • 2 Beds
  • 2 Baths
  • 1,072 Sq Ft

  4350 Chatham Dr Unit 307, Longboat Key, FL 34228

  Luxury Coastal Living at Longboat Harbour: Experience stunning canal views and modern elegance in this impeccably renovated 3rd-floor condo, ideally situated in the desirable all-age community of Longboat Harbour. Offered turnkey furnished, this beautifully curated residence is ready for your immediate enjoyment, whether you're seeking a winter retreat or full-time coastal living. Step inside to

  

  Marsha Winegarden

  WAGNER REALTY

  (941) 239-6809

  4350 Chatham Dr Unit 307, Longboat Key, FL 34228
• 

  

  /11

  $3,200 per month

  • 1 Bed
  • 1 Bath
  • 836 Sq Ft
  • Condo for Rent

  600 Sutton Place Unit 201, Longboat Key, FL 34228

  Available 6/1/25 **** Sarasota Bay view. 1 Bedroom x 1 1/2 Bathroom Condo. Living Room looks out over the pool that sits on Sarasota Bay. Fully furnished. 90 day minimum rental period. Prefer 6 mo.- 1 year rental. Sutton Place has many amenities including two heated pools, bicycle storage, outdoor grills, Gulf beach access with beach house, 1 assigned parking spot and several shared guest spaces.

  

  Tracy Srodes

  FINE PROPERTIES

  (941) 335-6064

  600 Sutton Place Unit 201, Longboat Key, FL 34228
• 

  /2

  $655,000 Sold Dec 10, 2025

  560 Cedar St, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft
  • Built 1970

  Last Sold Summary

  • 12% Below List Price
  • $359/SF
  • 64 Days On Market

  Last Listing Agent Lauren Hofing THE KEYES COMPANY - SARASOTA

  560 Cedar St, Longboat Key, FL 34228
• 

  /2

  Est $1,641,999 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,642 Sq Ft

  5901 Emerald Harbor Dr, Longboat Key, FL 34228

  5901 Emerald Harbor Dr, Longboat Key, FL 34228
• 

  

  /100

  $8,700,000

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

  560 Harbor Cove Cir, Longboat Key, FL 34228

  A rare and extraordinary offering inside the exclusive Bay Harbour within Bay Isles on Longboat Key, this peninsula estate delivers unmatched privacy, breathtaking Sarasota Bay views, and direct boating access to both the Intracoastal Waterway and the Gulf of Mexico. Positioned at the end of a quiet cul-de-sac on a three-sided waterfront peninsula, it includes two private boat docks with water

  

  Rachel Tritschler

  RE/MAX ALLIANCE GROUP

  (941) 919-3707

  560 Harbor Cove Cir, Longboat Key, FL 34228
• 

  

  /48

  $9,000 per month

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Condo for Rent

  830 Bayport Way Unit 830, Longboat Key, FL 34228

  Beautifully appointed seasonal/short term rental at Bayport Beach and Tennis Club on Longboat Key. This spacious 2/2 residence comes turnkey furnished and equipped with flat screen TV's, cable and WiFi. This residence features a large outdoor patio with garden views and plenty of seating. Bayport sits on 27 lushly landscaped acres and has 1200 feet of private beach. Complimentary beach chairs and

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 207-4978

  830 Bayport Way Unit 830, Longboat Key, FL 34228
• 

  /2

  $350,000 Sold Jul 03, 2025

  3802 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,396 Sq Ft
  • Built 1970

  Last Sold Summary

  • 18% Below List Price
  • $251/SF
  • 70 Days On Market

  Current Estimated Value $368,501

  Last Listing Agent Kathleen Magnus FLORIDA GALLERY REAL ESTATE

  3802 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
• 

  /2

  Est $7,868,942 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,820 Sq Ft

  6877 Gulf of Mexico Dr, Longboat Key, FL 34228

  6877 Gulf of Mexico Dr, Longboat Key, FL 34228
• 

  

  /95

  $450,000

  • 1 Bed
  • 2 Baths
  • 1,244 Sq Ft

  619 Cedars Ct, Longboat Key, FL 34228

  Welcome to your cozy island townhome at the north end of Longboat Key. Perfect as a fulltime residence, seasonal retreat, or investment property, this one-bedroom, two-bath unit fits your needs. This two-story property weathered three hurricanes in 2024, sustaining only minor flooding in the garage during Hurricane Helene and a cracked top-floor window during Hurricane Milton. The HOA will cover

  

  Simone Schaerf

  MICHAEL SAUNDERS & COMPANY

  (941) 219-0078

  619 Cedars Ct, Longboat Key, FL 34228
• 

  

  /48

  $9,000 per month

  • 3 Beds
  • 2 Baths
  • 1,731 Sq Ft
  • Condo for Rent

  5621 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228

  Available December and January .Call for rates and availability .Looking for a vacation in warm sunny Florida in a condo where you walk directly out onto the deck directly onto the beach? Stay in this 3 bedroom (2 king beds/1 queen), 2 bath condo in Salty Acres with 2 covered parking spaces. It is on the Gulf Side beach with amazing views. Condo is beautiful and recently remodeled. It must be a

  

  William Glade

  WILLIAM GLADE LIC. REAL ESTATE BROKER

  (941) 207-6603

  5621 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
• 

  /2

  $880,000 Sold Apr 07, 2025

  1930 Harbourside Dr Unit 113, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,905 Sq Ft
  • Built 1982

  Last Sold Summary

  • $462/SF

  Current Estimated Value $828,877

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  1930 Harbourside Dr Unit 113, Longboat Key, FL 34228
• 

  /2

  Est $507,757 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,440 Sq Ft

  613 Cedars Ct, Longboat Key, FL 34228

  613 Cedars Ct, Longboat Key, FL 34228
• 

  

  /82

  $10,900,000

  • 8 Beds
  • 8 Baths
  • 5,886 Sq Ft

  4473 Gulf of Mexico Dr, Longboat Key, FL 34228

  Rare opportunity, two fully furnished TWIN residences (TWO UNITS BEING SOLD AS ONE 4473+4477 Gulf of Mexico Drive ). Directly on the pristine shores of Longboat Key! Combined 8 bedrooms, 8 Bathrooms. Spanning nearly 6,000 sq. ft., on .58 GULF-FRONT acres, this two-story property offers mirror-image residences, each thoughtfully decorated with both modern and timeless designs. A true investment

  

  Curtis Andrews

  BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  (941) 841-8278

  4473 Gulf of Mexico Dr, Longboat Key, FL 34228
• 

  

  /60

  $10,000 per month

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Condo for Rent

  805 Bayport Way Unit 805, Longboat Key, FL 34228

  Pleasantly perfect! This spacious well appointed 2 bedroom, 2 bathroom condo is fully furnished, so just bring your beach gear and move right in. Bayport Beach and Tennis Club offers a wonderful pristine private beach exclusive for your enjoyment, with Intracoastal Bay Access. Tim Seibert, designer of Bayport, sought to create private villas surrounded by lush landscaped tropical gardens, and he

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 207-8014

  805 Bayport Way Unit 805, Longboat Key, FL 34228
• 

  /2

  $975,000 Sold Jul 28, 2025

  663 Penfield St, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 1,446 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $674/SF
  • 7 Days On Market

  Current Estimated Value $963,792

  Last Listing Agent Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

  663 Penfield St, Longboat Key, FL 34228
• 

  /2

  Est $246,028 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 630 Sq Ft

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

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

  

  /45

  $590,000

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

  2301 Gulf of Mexico Dr Unit 54, Longboat Key, FL 34228

  ****Creatively coined “Studio 54,” located at The Islander Club on Longboat Key Beach, this 2-bedroom, 2-bathroom condominium has an enormous lanai that brings the beautiful island breezes in all year long. Located in an upgraded and modern building directly on the beach, this disco pad is fresh, light, bright and happening. The front of this condo faces east, overlooking the lush grounds and the

  

  Meredith Van Vaals

  COLDWELL BANKER REALTY

  (941) 220-0872

  2301 Gulf of Mexico Dr Unit 54, Longboat Key, FL 34228
• 

  

  /62

  $10,000 per month

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft
  • Condo for Rent

  741 Bayport Way Unit 741, Longboat Key, FL 34228

  ABSOLUTELY GORGEOUS INSIDE! Bayport Beach & Tennis Club is an amenity-rich community at sea's edge and is situated in the middle of Longboat Key. This 2 bedroom, 2 bathroom fully FURNISHED rental is tastefully and brilliantly decorated. This residence offers a wonderful retreat as a Seasonal rental or a shorter Monthly respite. Bayporters' enjoy an active island lifestyle with 4 Har Tru tennis

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 207-8515

  741 Bayport Way Unit 741, Longboat Key, FL 34228
• 

  /2

  $1,250,000 Sold Apr 15, 2025

  541 Edlee Ln, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,664 Sq Ft
  • Built 1976

  Last Sold Summary

  • 10% Below List Price
  • $469/SF
  • 50 Days On Market

  Current Estimated Value $1,215,792

  Last Listing Agent Lisa Garcia COLDWELL BANKER REALTY

  541 Edlee Ln, Longboat Key, FL 34228
• 

  /2

  Est $1,919,212 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,925 Sq Ft

  3030 Grand Bay Blvd Unit 346, Longboat Key, FL 34228

  3030 Grand Bay Blvd Unit 346, Longboat Key, FL 34228
• 

  

  /32

  $1,590,000

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft

  601 Longboat Club Rd Unit 504S, Longboat Key, FL 34228

  Welcome to Unit 504S, a rare corner residence perched above the sand and sea on the highly sought-after south end of Longboat Key. With uninterrupted views of both the Gulf of Mexico and the Links on Longboat Golf Course, this spacious 2-bedroom, 2.5-bath condominium is your dream coastal retreat. Spanning over 1,560 square feet, the split-bedroom floorplan provides an ideal layout for privacy

  

  Irma Scherer

  COMPASS FLORIDA LLC

  (941) 401-0752

  601 Longboat Club Rd Unit 504S, Longboat Key, FL 34228
• 

  

  /52

  $9,000 per month

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Condo for Rent

  833 Bayport Way Unit 833, Longboat Key, FL 34228

  WELCOMING and tastefully decorated, this fully furnished 2 bedroom, 2 bathroom unit offers a relaxing atmosphere. The open concept floor plan with split bedrooms is spacious and inviting and this unit features two interior patios with serene canopy garden views. This amenity-rich community at sea’s edge is situated in the middle of Longboat Key and features 27 picturesque acres of well maintained

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 207-7270

  833 Bayport Way Unit 833, Longboat Key, FL 34228
• 

  /2

  $4,000,000 Sold Mar 25, 2025

  3480 Bayou Sound, Longboat Key, FL 34228

  • 5 Beds
  • 4.5 Baths
  • 3,926 Sq Ft
  • Built 2024

  Last Sold Summary

  • 23% Below List Price
  • $1,019/SF
  • 57 Days On Market

  Current Estimated Value $3,500,803

  Last Listing Agent Nicholle McKiernan COLDWELL BANKER REALTY

  3480 Bayou Sound, Longboat Key, FL 34228
• 

  /2

  Est $2,971,843 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,367 Sq Ft

  3464 Mistletoe Ln, Longboat Key, FL 34228

  3464 Mistletoe Ln, Longboat Key, FL 34228
• 

  

  /48

  $595,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft

  4320 Falmouth Dr Unit 301, Longboat Key, FL 34228

  Under contract-accepting backup offers. Experience true Bay-to-Gulf living with exclusive access to Sarasota Bay and the Longboat Key Beach through the private gated beach club just steps away! This beautifully fully renovated 2-bedroom and 2-bathroom top-floor end-unit condo in the highly desirable Longboat Harbour community combines modern updates, comfortable living spaces, and stunning water

  

  Kevin Tai

  PREFERRED SHORE LLC

  (941) 207-0454

  4320 Falmouth Dr Unit 301, Longboat Key, FL 34228
• 

  

  /57

  $9,500 per month

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Condo for Rent

  519 Bayport Way Unit 519, Longboat Key, FL 34228

  Seasonal rental in Bayport Beach and Tennis Club which is a beautiful, established, award-winning, amenity-rich community with immediate access to a peaceful private beach that continues in both directions for miles along the Gulf of Mexico shore. The complex includes a large pool surrounded by flowering trees, four immaculately maintained clay tennis courts, fitness center, a large clubhouse,

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 273-0449

  519 Bayport Way Unit 519, Longboat Key, FL 34228
• 

  /2

  $1,500,000 Sold Aug 19, 2025

  1701 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,551 Sq Ft
  • Built 1975

  Last Sold Summary

  • 16% Below List Price
  • $967/SF
  • 81 Days On Market

  Current Estimated Value $1,422,927

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

  1701 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228
• 

  

  /57

  Est $3,331,751 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,272 Sq Ft

  6941 Bayside Dr, Longboat Key, FL 34228

  6941 Bayside Dr, Longboat Key, FL 34228
• 

  

  /50

  $649,999 Open Sun 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,187 Sq Ft

  3320 Gulf of Mexico Dr Unit 207-C, Longboat Key, FL 34228

  Modern Waterfront Living in the Heart of Longboat Key-Experience the best of coastal living in this beautifully renovated 2-bedroom, 2-bathroom condo, perfectly situated on the water in one of Longboat Key’s most desirable communities. This light-filled residence features a newly reimagined open-concept kitchen with gleaming quartz countertops, bright modern cabinetry, premium stainless steel

  

  Tami Cashi

  COLDWELL BANKER REALTY

  (941) 206-4076

  3320 Gulf of Mexico Dr Unit 207-C, Longboat Key, FL 34228
• 

  

  /75

  $13,500 per month

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft
  • Condo for Rent

  716 Bayport Way Unit 716, Longboat Key, FL 34228

  GORGEOUS INSIDE! This beautifully remodeled ground floor, corner unit, features 3 bedrooms, 2 bathrooms with an open concept floor plan. This home welcomes you into an expansive Living/Dining/Kitchen and offers plenty of natural light. In addition, it boasts a generous size master bedroom with en suite bathroom and an alcove that accommodates a desk and seating area. Bayport Beach & Tennis Club

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 206-0566

  716 Bayport Way Unit 716, Longboat Key, FL 34228
• 

  /2

  $1,075,000 Sold Oct 16, 2025

  240 Sands Point Rd Unit 4403, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 626 Sq Ft
  • Built 1982

  Last Sold Summary

  • 1% Below List Price
  • $1,717/SF
  • 2 Days On Market

  Last Listing Agent Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  240 Sands Point Rd Unit 4403, Longboat Key, FL 34228
• 

  

  /13

  Est $972,153 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 642 Sq Ft

  210 Sands Point Rd Unit 2502, Longboat Key, FL 34228

  210 Sands Point Rd Unit 2502, Longboat Key, FL 34228
• 

  

  /57

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 1,409 Sq Ft

  1050 Longboat Club Rd Unit 301, Longboat Key, FL 34228

  Imagine waking up every morning to the sound of gentle waves and stepping onto your balcony to enjoy uninterrupted, straight-on Gulf views—this rarely available 01-stack residence delivers beachfront living exactly the way it should be. Perfectly positioned behind the private gates of the Longboat Key Club and nestled between the iconic Resort at Longboat Key Club and the spectacular new St.

  

  Greg Martin

  STERLING REALTY

  (941) 369-9007

  1050 Longboat Club Rd Unit 301, Longboat Key, FL 34228
• 

  

  /56

  $10,000 per month

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

  522 Bayport Way Unit 522, Longboat Key, FL 34228

  GORGEOUS LONG TERM RENTAL!! Bayport Beach & Tennis CLub is an amenity-rich community at sea's edge and is situated in the middle ofLongboat Key. This 2 bedroom, 2 bathroom fully furnished rental is beautifully appointed. This residence offers a wonderful retreat as a annual. Bayporters' enjoy an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  (941) 207-0065

  522 Bayport Way Unit 522, Longboat Key, FL 34228
• 

  /2

  $1,560,000 Sold Oct 28, 2025

  2020 Harbourside Dr Unit 454, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,462 Sq Ft
  • Built 1984

  Last Sold Summary

  • 11% Below List Price
  • $634/SF
  • 185 Days On Market

  Last Listing Agent Reid Murphy DEVELOPERS REALTY LBK, INC

  2020 Harbourside Dr Unit 454, Longboat Key, FL 34228
• 

  

  /30

  Est $521,878 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 642 Sq Ft

  225 Sands Point Rd Unit 6105, Longboat Key, FL 34228

  225 Sands Point Rd Unit 6105, Longboat Key, FL 34228

Showing Results 1 - 40, Page 1 of 18