11,341

Longboat Key, FL Homes

Section Image
  • /55

    $1,299,000

    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft

    7001 Gulf of Mexico Dr Unit 24, Longboat Key, FL 34228

    Welcome to an extraordinary Gulf-front residence where timeless coastal elegance meets uncompromising craftsmanship. Completely reimagined from top to bottom, this impeccably furnished two-bedroom, two-bath condominium offers an unparalleled blend of luxury, comfort, and breathtaking natural beauty.Perfectly positioned on the second floor, this architectural gem enjoys panoramic, unobstructed

    Mike Seamon PREMIER SOTHEBY'S INTERNATIONAL REALTY

    7001 Gulf of Mexico Dr Unit 24, Longboat Key, FL 34228
  • /25

    $8,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,273 Sq Ft
    • Condo for Rent

    2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228

    LONGBOAT KEY...SUNSET BEACH CLUB II. Nicely appointed 2 bedroom, 2 bath condo, turnkey furnished. Entertainment center in the living room with a flat screen TV. King bed in the master and twin beds in the guest room. Lovely view of the Gulf of Mexico and the pool. Capture beautiful sunsets every night from the balcony. This unit is equipped with everything you will need so you can vacation with

    Teresa Ribaudo JENNETTE PROPERTIES INC

    2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228
  • /2

    $190,000

    Sold Mar 12, 2026

    3710 Gulf of Mexico Dr Unit E11, Longboat Key, FL 34228

    • 1 Bed
    • 1 Bath
    • 248 Sq Ft
    • Built 1962

    Last Sold Summary

    • 5% Below List Price
    • $766/SF
    • 25 Days On Market

    Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC

    3710 Gulf of Mexico Dr Unit E11, Longboat Key, FL 34228
    • /2

      Est $418,501

      Not Listed For Sale

      3740 Gulf of Mexico Dr Unit 116, Longboat Key, FL 34228

      • 1 Bed
      • 1 Bath
      • 861 Sq Ft
      • Built 1950
      3740 Gulf of Mexico Dr Unit 116, Longboat Key, FL 34228

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Marni Hayden CHROME REALTY LLC

  • /27

    $675,000

    • Land
    • 6,098 Sq Ft
    • $4,821,429 per Acre

    525 Channel Ln, Longboat Key, FL 34228

    LOCATION, LOCATION, LOCATION!!! Discover a rare and recently cleared premium homesite located on one of Longboat Key’s most charming and historic streets. This exclusive New Pass Shores community features only 6 homes, providing an intimate neighborhood atmosphere. While this homesite is not directly on the waterfront, it includes a NEW composite wood boat dock shared with just 3 other homes,

    Chris McKee VUE REALTY, LLC

    525 Channel Ln, Longboat Key, FL 34228
  • /32

    $11,400 Per Month

    • 2 Beds
    • 2 Baths
    • 1,503 Sq Ft
    • Condo for Rent

    1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

    Seasonal. Not available Jan - April 2025. Amazing sunsets from this fabulous 5th floor, direct Gulf beach front, 2 BD, 2 BA condo. Meticulously maintained, this condo has everything you need for a care-free beach vacation! Master suite features king size bed, private bath with Gulf view. Guest room offers twin sleeping arrangements with private entrance to bath. For your comfort, there's flat

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
  • /2

    $605,000

    Sold Dec 30, 2025

    1930 Harbourside Dr Unit 136, Longboat Key, FL 34228

    • 2 Beds
    • 2 Baths
    • 1,270 Sq Ft
    • Built 1982

    Last Sold Summary

    • 11% Below List Price
    • $476/SF
    • 16 Days On Market

    Current Estimated Value $625,342

    Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

    1930 Harbourside Dr Unit 136, Longboat Key, FL 34228
    • /8

      Not Listed For Sale

      2600 Harbourside Dr Unit G-19 & G-20, Longboat Key, FL 34228

      2600 Harbourside Dr Unit G-19 & G-20, Longboat Key, FL 34228

      Last Sold Summary

      • 788 Days On Market

      Last Listing Agent James Buchanan JAMES BUCHANAN REALTY

  • /50

    $1,195,000

    • 3 Beds
    • 3 Baths
    • 2,135 Sq Ft

    1906 Harbourside Dr Unit 304, Longboat Key, FL 34228

    Behind the gates of Bay Isles, this beautifully updated waterfront townhome in Fairway Bay offers the rare convenience of a private deepwater dock accommodating vessels up to 40’. From here, Sarasota Bay, waterfront dining and the Gulf are only minutes away by boat, while peaceful water views become part of the backdrop to everyday living. A stepped walkway welcomes you inside, where more than

    Bruce Myer COLDWELL BANKER REALTY

    1906 Harbourside Dr Unit 304, Longboat Key, FL 34228
  • /66

    $7,200 Per Month

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

    3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

    Absolutely beautiful turnkey furnished condo at the sought after Portobello on Longboat Key. The meticulously maintained, light and bright two bedroom, two bathroom unit has a combination living room/dining room, separate kitchen with stainless steel appliances, split bedrooms and a washer and dryer in the unit. Newly renovated bathrooms and kitchen with high end finishes round out this fabulous

    C. Alison Hunter JENNETTE PROPERTIES INC

    3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
  • /2

    $555,000

    Sold May 15, 2026

    4234 Gulf of Mexico Dr Unit J1, Longboat Key, FL 34228

    • 2 Beds
    • 2 Baths
    • 1,150 Sq Ft
    • Built 1973

    Last Sold Summary

    • 7% Below List Price
    • $483/SF
    • 53 Days On Market

    Current Estimated Value $576,111

    Last Listing Agent Mike Seamon PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4234 Gulf of Mexico Dr Unit J1, Longboat Key, FL 34228
  • /37

    $310,000

    • 1 Bed
    • 1 Bath
    • 680 Sq Ft

    3710 Gulf of Mexico Dr Unit E22, Longboat Key, FL 34228

    BEAUTIFULLY REMODELED: This home is the epitome of simple elegance with a bit of modern flair. It has been remodeled to create a home that is very open and full of light. It features a large Living Room with a wall-mounted TV and a fireplace; a kitchen that has all new cabinets and granite counter tops; a Primary bedroom, with a small attached room that could easily be converted to a small

    Bill Shuttleworth EDGEWATER REAL ESTATE, INC

    3710 Gulf of Mexico Dr Unit E22, Longboat Key, FL 34228
  • /12

    $30,000 Per Month

    • 1 Bed
    • 1.5 Baths
    • 1,684 Sq Ft
    • Condo for Rent

    1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228

    Enter the unit from a private elevator which features a spacious, open-plan living area with large windows allowing natural light and incredible views of the surrounding landscape and Sarasota Bay. The lavish living space opens up onto a stunning balcony that overlooks Sarasota Bay and the St. Regis grounds and includes a gas grill. The stylish living area includes high-end furniture with a

    Larry Starr SVN COMMERCIAL ADVISORY GROUP

    1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
  • /2

    $1,400,000

    Sold Aug 25, 2025

    2301 Gulf of Mexico Dr Unit 52, Longboat Key, FL 34228

    • 2 Beds
    • 2 Baths
    • 1,235 Sq Ft
    • Built 1970

    Last Sold Summary

    • 15% Below List Price
    • $1,134/SF
    • 149 Days On Market

    Current Estimated Value $1,360,376

    Last Listing Agent Doug Parks MICHAEL SAUNDERS & COMPANY

    2301 Gulf of Mexico Dr Unit 52, Longboat Key, FL 34228
    • /2

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 1,300 Sq Ft
      • Built 1979
      5393 Gulf of Mexico Dr Unit 216C, Longboat Key, FL 34228

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Bobbie Banan MICHAEL SAUNDERS & COMPANY

  • /54

    $1,445,000

    $50K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,180 Sq Ft

    1914 Harbour Links Cir Unit 10, Longboat Key, FL 34228

    Tucked behind the gates of Bay Isles in the Emerald Pointe community, this 3BR/3.5BA residence offers 2,180+/- sq. ft. of thoughtfully designed living space with a layout that blends privacy, flexibility and inviting outdoor living. From the moment you arrive, a paver drive framed by lush landscaping and a striking 2-story façade with barrel tile roof set a warm and welcoming tone. A paver

    Bruce Myer COLDWELL BANKER REALTY

    1914 Harbour Links Cir Unit 10, Longboat Key, FL 34228
  • /77

    $3,750 Per Month

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

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

    AVAILABLE IMMEDIATELY PENDING HOA APPROVAL! 2 MONTH MINIMUM! BOOKED FOR JAN-MARCH 2027 SEASON! 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

    Brigette Marcus NEXTHOME EXCELLENCE

    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
  • /2

    $1,315,000

    Sold Jul 31, 2026

    370 Gulf of Mexico Dr Unit 432, Longboat Key, FL 34228

    • 4 Beds
    • 4 Baths
    • 2,900 Sq Ft
    • Built 1994

    Last Sold Summary

    • 25% Below List Price
    • $453/SF
    • 272 Days On Market

    Current Estimated Value $1,624,899

    Last Listing Agent Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

    370 Gulf of Mexico Dr Unit 432, Longboat Key, FL 34228
    • /66

      Est $429,379

      Not Listed For Sale

      4870 Gulf of Mexico Dr Unit V12, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 1,025 Sq Ft
      • Built 1974
      4870 Gulf of Mexico Dr Unit V12, Longboat Key, FL 34228

      Last Sold Summary

      • 135 Days On Market

      Last Listing Agent Tryla Brown Larson BERKSHIRE HATHAWAY HOMESERVICE

  • /10

    $600,000

    2600 Harbourside Dr Unit O-13/14, Longboat Key, FL 34228

    104 ft. x 29.5 ft. Boat Slip at Longboat Key Moorings Marina. This is a 104 ft. long T-dock/face dock ready to accommodate a large yacht; ample electrical service outlets. O-13 is 49.5 feet, and O-14 is 54.5 ft, because this slip is deeded as two slips, two boats are permitted. Direct access to Sarasota Bay and the ICW with exceptional views of Sarasota Bay. The deep water marina is as much a

    Jennifer Wilson LBRE LLC

    2600 Harbourside Dr Unit O-13/14, Longboat Key, FL 34228
  • /61

    $14,750 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,292 Sq Ft
    • House for Rent

    513 Gunwale Ln, Longboat Key, FL 34228

    Welcome to Beach & Boaters Paradise located on Longboat Key. Enjoy immediate access access to beautiful Sarasota Bay, the Gulf of Mexico and Longboat Key’s sugar white sand beaches and emerald green waters. Fish off the dock or walk to the beach! Or enjoy the large heated pool in this 4 bedroom, 3.5 bath luxury waterfront home designed to provide you and your family a lifetime of vacation

    Marcia Benson Berkshire Hathaway Florida Realty

    513 Gunwale Ln, Longboat Key, FL 34228
  • /2

    $2,000,000

    Sold Oct 15, 2025

    4 Winslow Place, Longboat Key, FL 34228

    • 4 Beds
    • 3 Baths
    • 3,288 Sq Ft
    • Built 1963

    Last Sold Summary

    • $608/SF
    • 0 Days On Market

    Current Estimated Value $2,046,537

    Last Listing Agent Kaisen Mitchell COLDWELL BANKER REALTY

    4 Winslow Place, Longboat Key, FL 34228
    • /59

      Est $3,298,606

      Not Listed For Sale

      603 Buttonwood Dr, Longboat Key, FL 34228

      • 4 Beds
      • 3.5 Baths
      • 3,413 Sq Ft
      • Built 2013
      603 Buttonwood Dr, Longboat Key, FL 34228

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Mackenzie Longueuil MICHAEL SAUNDERS & COMPANY

  • /15

    $235,000

    2600 Harbourside Dr Unit O-04, Longboat Key, FL 34228

    Great city skyline views and easy access! This 45 x 20 foot slip at Longboat Key Club Moorings is located on the South side of O-dock. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes

    Jennifer Wilson LBRE LLC

    2600 Harbourside Dr Unit O-04, Longboat Key, FL 34228
  • /30

    $11,769 Per Month

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

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

    ..."' short stories. ....on the island of longboat key You are on the beach included is swimming pool...and a world class tennis courtf...looking play with others and league Town of Longboat Key tennis three blocks away...fitness gym.. . This is direct Gulf front unit with interior hallways from the balcony ,the kitchen,the living room couch...Your on the water.. Breathtaking view of the

    Gerald Cunningham KELLER WILLIAMS ON THE WATER S

    2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
  • /2

    $1,725,000

    Sold Feb 12, 2026

    2550 Harbourside Dr Unit 322, Longboat Key, FL 34228

    • 3 Beds
    • 3 Baths
    • 2,830 Sq Ft
    • Built 1990

    Last Sold Summary

    • 25% Below List Price
    • $610/SF
    • 323 Days On Market

    Current Estimated Value $1,680,168

    Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

    2550 Harbourside Dr Unit 322, Longboat Key, FL 34228
    • /33

      Est $847,540

      Not Listed For Sale

      1085 Gulf of Mexico Dr Unit 501, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 1,172 Sq Ft
      • Built 1981
      1085 Gulf of Mexico Dr Unit 501, Longboat Key, FL 34228

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  • /85

    $950,000

    • 3 Beds
    • 2.5 Baths
    • 2,451 Sq Ft

    2350 Harbour Oaks Dr, Longboat Key, FL 34228

    Move right in and start enjoying the Longboat Key lifestyle! Perfectly positioned behind the gates of highly sought after Bay Isles, this beautifully renovated residence combines elegant updates, low-maintenance living, and one of the area's most desirable resort-style communities. Every major improvement has already been completed, allowing you to simply unpack and begin enjoying paradise. The

    Jason Wood CORCORAN DWELLINGS REALTY

    2350 Harbour Oaks Dr, Longboat Key, FL 34228
  • /48

    $4,000 Per Month

    • 1 Bed
    • 1.5 Baths
    • 1,080 Sq Ft
    • Condo for Rent

    1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228

    Seasonal Rental – Beachfront Living at The Privateer on Longboat Key / Escape the cold and enjoy a relaxing winter retreat in this beautifully maintained 1-bedroom, 1-bathroom condo located on the 4th floor of the highly sought-after The Privateer on Longboat Key. This inviting residence offers a bright and open layout, a well-equipped kitchen, and a comfortable, spacious bedroom designed for

    Cody Smith RENT SARASOTA

    1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
  • /2

    $995,000

    Sold Apr 24, 2026

    1000 Longboat Club Rd Unit 402, Longboat Key, FL 34228

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • Built 1972

    Last Sold Summary

    • 9% Below List Price
    • $771/SF
    • 139 Days On Market

    Current Estimated Value $988,669

    Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

    1000 Longboat Club Rd Unit 402, Longboat Key, FL 34228
    • /45

      Est $1,511,951

      Not Listed For Sale

      2105 Gulf of Mexico Dr Unit 3503, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 1,463 Sq Ft
      • Built 1984
      2105 Gulf of Mexico Dr Unit 3503, Longboat Key, FL 34228

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Pam Charron COMPASS FLORIDA LLC

  • /14

    $675,000

    $100K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 933 Sq Ft

    2089 Gulf of Mexico Dr Unit G1108, Longboat Key, FL 34228

    Welcome to G1-108, a recently remodeled and fully-furnished residence in Seaplace! Overlooking the pristine sands and sunsets of the Gulf, this first-floor 2 bedroom/2 bathroom residence offers unparalleled access to the beach and resort-style amenities. In early 2025, this residence was extensively remodeled, including impact-resistant hurricane door, new bathrooms and a new kitchen with

    David DeNardo COLDWELL BANKER REALTY

    2089 Gulf of Mexico Dr Unit G1108, Longboat Key, FL 34228
  • /36

    $11,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,602 Sq Ft
    • Condo for Rent

    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228

    AVAILABLE DEC. '26 THROUGH FEB.'27. Beautiful 9th floor, 1600 sq. ft. 2 bedroom 2 bath at the sort after Beaches condominium which is within the gates of the Longboat Key Club. Updated kitchen and bathrooms. Fabulous bay, and Longboat Key Club golf views. Wrap around balcony with partial Gulf view. Washer/dryer in the unit, pool, fitness center and tennis courts plus 24 hr. Concierge and garage

    Brenda Cozy COLDWELL BANKER REALTY

    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
  • /2

    $715,000

    Sold Dec 18, 2025

    2110 Harbourside Dr Unit 522, Longboat Key, FL 34228

    • 3 Beds
    • 2 Baths
    • 2,039 Sq Ft
    • Built 1988

    Last Sold Summary

    • 25% Below List Price
    • $351/SF
    • 302 Days On Market

    Current Estimated Value $767,463

    Last Listing Agent Andrew Vac RE/MAX ALLIANCE GROUP

    2110 Harbourside Dr Unit 522, Longboat Key, FL 34228
    • /20

      Est $316,727

      Not Listed For Sale

      2800 Harbourside Dr Unit E-21, Longboat Key, FL 34228

      • Studio
      • 1,260 Sq Ft
      • Built 1987
      2800 Harbourside Dr Unit E-21, Longboat Key, FL 34228

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Jennifer Wilson LBRE LLC

  • /33

    $1,100,000

    • 2 Beds
    • 2 Baths
    • 1,336 Sq Ft

    4325 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228

    Experience coastal living in this two-bedroom, two-bath direct Gulf-front residence ideally on the main floor of a desirable mid-rise community on Longboat Key. Freshly painted and thoughtfully enhanced with quartz countertops in both the kitchen and laundry room, along with recently updated washer and dryer appliances, the residence also features crown molding, updated trim and plantation

    Dennis Girard PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4325 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
  • /33

    $18,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 2,143 Sq Ft
    • Condo for Rent

    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228

    2027 Season Rental Rate will be $24,000. The Residences at The St. Regis Longboat Key offer an exceptional blend of ultra-luxury living and world-class resort amenities on the pristine shores of the Gulf of Mexico. This exclusive beachfront community features exquisitely designed residences with soaring ceilings, floor-to-ceiling glass doors, and panoramic sunrise-to-sunset views. The gourmet

    Melissa Gissinger MICHAEL SAUNDERS & COMPANY

    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
  • /2

    $625,000

    Sold Mar 09, 2026

    6901 Poinsetta Ave, Longboat Key, FL 34228

    • 4 Beds
    • 3 Baths
    • 2,173 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Below List Price
    • $288/SF
    • 2 Days On Market

    Current Estimated Value $636,264

    Last Listing Agent Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

    6901 Poinsetta Ave, Longboat Key, FL 34228
    • /31

      Est $2,209,998

      Not Listed For Sale

      581 de Narvaez Dr, Longboat Key, FL 34228

      • 3 Beds
      • 3.5 Baths
      • 2,134 Sq Ft
      • Built 2023
      581 de Narvaez Dr, Longboat Key, FL 34228

      Last Sold Summary

      • 184 Days On Market

      Last Listing Agent Kate Enis FINE PROPERTIES

Showing Results 481 - 520, Page 13 of 18

How to Buy a Home How to Finance a Home How to Sell a Home