Longboat Key, FL Homes

• 

  

  

  /55

  $1,475,000

  • 3 Beds
  • 3 Baths
  • 1,859 Sq Ft

  1445 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  Timeless sophistication meets resort-style elegance in this fully renovated 3-bedroom residence at the coveted Players Club on Longboat Key. Ideally situated on the sought-after south end of the island, this home places you moments from the prestigious St. Regis Hotel, the Longboat Key Club, Publix, and the upscale dining, boutique shopping, and cultural attractions of St. Armands Circle and

  Mairead Smialek COLDWELL BANKER REALTY

  1445 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
• 

  

  

  /28

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Condo for Rent

  5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228

  Breathtaking Direct Gulf views from this second floor condo at Longboat Terrace. This two bedroom, two bath has everything you need to make this your home away from home. Both the master and guest suites have their own private baths and balconies. Enjoy the morning paper at the breakfast nook or entertain in the great room. The brand new living room furniture features a sleeper sofa, perfect for

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
• 

  

  /2

  $3,700,000 Sold Jun 18, 2025

  551 Ranger Ln, Longboat Key, FL 34228

  • 5 Beds
  • 5.5 Baths
  • 4,117 Sq Ft
  • Built 2016

  Last Sold Summary

  • 15% Below List Price
  • $899/SF
  • 75 Days On Market

  Current Estimated Value $3,528,014

  Last Listing Agent Kathy Callahan MICHAEL SAUNDERS & COMPANY

  551 Ranger Ln, Longboat Key, FL 34228
• 

  

  

  /54

  Est $688,939 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft

  5265 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  5265 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
• 

  

  

  /17

  $450,000

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

  72 ft x 26 ft Boat Slip on L-dock at Longboat Key Moorings Marina for sale. Exceptional views of Sarasota Bay and the city skyline from atop your flybridge. LBK Club membership is 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, Marina village that includes

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit L-04, Longboat Key, FL 34228
• 

  

  /28

  $8,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,780 Sq Ft
  • Condo for Rent

  455 Longboat Club Rd Unit 401, Longboat Key, FL 34228

  Welcome to Paradise! Beautiful 3 bedroom 3.5 baths, luxury split floor plan condo on LONGBOAT KEY. Behind the gates of Longboat Key Club, known for its privacy and yet close to St. Armand's Circle for dining, shopping, entertainment & cultural offerings of downtown Sarasota. Located on the south end of Longboat Key, this tastefully furnished 4th floor updated unit offers a partial view of the

  Deserea Hardy ROSSI & COMPANY INC

  455 Longboat Club Rd Unit 401, Longboat Key, FL 34228
• 

  /2

  $1,950,000 Sold May 28, 2025

  535 Sanctuary Dr Unit A202, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,580 Sq Ft
  • Built 1990

  Last Sold Summary

  • 17% Below List Price
  • $756/SF
  • 52 Days On Market

  Current Estimated Value $1,882,372

  Last Listing Agent Kathy Callahan MICHAEL SAUNDERS & COMPANY

  535 Sanctuary Dr Unit A202, Longboat Key, FL 34228
• 

  /2

  Est $327,953 Not Listed For Sale

  641 Fox St, Longboat Key, FL 34228

  641 Fox St, Longboat Key, FL 34228
• 

  

  /55

  $11,995,000

  • 5 Beds
  • 7 Baths
  • 6,959 Sq Ft

  6001 Gulf of Mexico Dr, Longboat Key, FL 34228

  A Gulf-Front Masterpiece on Longboat Key! This stunning Gulf-front estate is perfectly placed on nearly an acre of pristine Gulf-front property along the shoreline on Longboat Key. With direct Gulf frontage, this architectural masterpiece offers more than 6,900 square feet of refined interiors and panoramic views that stretch endlessly across the Gulf of Mexico. Designed for both privacy and

  Roger Pettingell COLDWELL BANKER REALTY

  6001 Gulf of Mexico Dr, 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

  $1,402,000 Sold Jan 02, 2025

  3140 Bayou Sound, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 3,312 Sq Ft
  • Built 1986

  Last Sold Summary

  • 12% Below List Price
  • $423/SF
  • 184 Days On Market

  Current Estimated Value $1,366,936

  Last Listing Agent Linda Weber COLDWELL BANKER REALTY

  3140 Bayou Sound, Longboat Key, FL 34228
• 

  

  /38

  Est $2,028,293 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,665 Sq Ft

  6840 Longboat Dr S, Longboat Key, FL 34228

  6840 Longboat Dr S, Longboat Key, FL 34228
• 

  

  /77

  $2,695,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,570 Sq Ft

  5930 Gulf of Mexico Dr, Longboat Key, FL 34228

  Under contract-accepting backup offers. A gated entrance and paver driveway surrounded by lush landscaping leads to this lovely home on a wide canal that is a boater's dream. The location is a private half plus acre estate across the street from the beautiful Gulf of Mexico and beach. The exquisite double entry etched doors open to the first living level of storage and an elevator plus staircase

  Reid Murphy DEVELOPERS REALTY LBK, INC

  5930 Gulf of Mexico Dr, Longboat Key, FL 34228
• 

  

  /25

  $9,000 per month

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

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

  SEASONAL; PRICE REDUCED!!! Available FEBRUARY - MARCH 2026!!! 30 day minimum. No damages sustained in Hurricane. Beautiful unit from floor to ceiling – you’ll just love the magnificent views from every room plus the 85 inch TV in this direct Gulf front residence. Perched on the seventh floor of Sea Gate, this Southern Longboat community offers gorgeous sand beaches, great location and amazing

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

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

  /2

  $555,000 Sold Jun 03, 2025

  2016 Harbourside Dr Unit 332, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,192 Sq Ft
  • Built 1984

  Last Sold Summary

  • 7% Below List Price
  • $466/SF
  • 24 Days On Market

  Current Estimated Value $552,481

  Last Listing Agent Francis Perdisatt PREFERRED SHORE LLC

  2016 Harbourside Dr Unit 332, Longboat Key, FL 34228
• 

  /2

  Est $712,643 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft

  4540 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

  4540 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228
• 

  

  /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
• 

  

  /22

  $8,000 per month

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

  3235 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  Stunning Portobello Vacation 2/2 Condo on Longboat Key. This beautiful condo provides easy and relaxed living with gorgeous direct gulf views. Full length screened lanai to enjoy the view. This totally renovated condo features luxurious and relaxed beach style decor, new windows and sliding glass doors, new laminate flooring and carpet, new kitchen appliances, three flat screen TVs with HD boxes

  Terri Lindsay LINDSAY LEASING LLC

  3235 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
• 

  /2

  $1,185,000 Sold Aug 27, 2025

  1045 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1981

  Last Sold Summary

  • 24% Below List Price
  • $788/SF
  • 372 Days On Market

  Current Estimated Value $1,187,641

  Last Listing Agent Maggie Hicks COLDWELL BANKER REALTY

  1045 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
• 

  

  /34

  Est $1,063,544 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,358 Sq Ft

  2101 Gulf of Mexico Dr Unit 2504, Longboat Key, FL 34228

  2101 Gulf of Mexico Dr Unit 2504, Longboat Key, FL 34228
• 

  

  /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 north side of P-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
• 

  

  /25

  $7,500 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

  $253,000 Sold Oct 02, 2025

  594 Spanish Dr S, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,427 Sq Ft
  • Built 1969

  Last Sold Summary

  • 33% Below List Price
  • $177/SF
  • 110 Days On Market

  Last Listing Agent Amber Lynch COMPASS FLORIDA LLC

  594 Spanish Dr S, Longboat Key, FL 34228
• 

  

  /60

  Est $707,819 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,753 Sq Ft

  3810 Gulf of Mexico Dr Unit F401, Longboat Key, FL 34228

  3810 Gulf of Mexico Dr Unit F401, Longboat Key, FL 34228
• 

  

  /55

  $679,000 Pending

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

  1930 Harbourside Dr Unit 136, Longboat Key, FL 34228

  Under contract-accepting backup offers. Sweeping bay views and refined comfort define this beautifully maintained 2BR/2BA residence in Fairway Bay on Longboat Key. A full wall of floor-to-ceiling sliders in the living room frames stunning views of the mangroves and open water, bringing the beauty of the bay into everyday living. Warm wood floors and soft neutral finishes create a classic,

  Bruce Myer COLDWELL BANKER REALTY

  1930 Harbourside Dr Unit 136, 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

  $2,150,000 Sold Dec 10, 2025

  603 Weston Pointe Ct, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,712 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Below List Price
  • $793/SF
  • 6 Days On Market

  Last Listing Agent Ryan Heers COLDWELL BANKER REALTY

  603 Weston Pointe Ct, Longboat Key, FL 34228
• 

  

  /32

  Est $423,735 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 812 Sq Ft

  4770 Gulf of Mexico Dr Unit V-6, Longboat Key, FL 34228

  4770 Gulf of Mexico Dr Unit V-6, Longboat Key, FL 34228
• 

  

  /93

  $865,000

  • 2 Beds
  • 2 Baths
  • 1,370 Sq Ft

  750 Bayport Way Unit 750, Longboat Key, FL 34228

  Experience contemporary coastal living in this fully renovated, turnkey-furnished unit ideally located in the heart of Longboat Key! Nestled between 1,200 feet of private, powder-soft beach on the Gulf and a serene fishing pier on Sarasota Bay, this residence offers the perfect blend of island tranquility and luxury!Step inside to discover a meticulously cared for interior space updated with

  Jennifer Albright HUNT BROTHERS REALTY, INC.

  750 Bayport Way Unit 750, Longboat Key, FL 34228
• 

  

  /25

  $12,500 per month

  • 3 Beds
  • 2.5 Baths
  • 2,532 Sq Ft
  • House for Rent

  2319 Harbour Oaks Dr, Longboat Key, FL 34228

  SEASONAL: All three baths have been 100% renovated. Just gorgeous! Photos to come. Harbour Oaks is resort-style living positioned behind the guarded Harbourside gates of Bay Isles. This updated 3 bedroom, 2 1/2 bath home overlooks the Longboat Key Club golf course! With over 2,500 sq. feet of living space, pool, private Beach Club access and sought after Southern Longboat address this is the

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  2319 Harbour Oaks Dr, Longboat Key, FL 34228
• 

  /2

  $700,000 Sold Nov 24, 2025

  7061 Longboat Dr E, Longboat Key, FL 34228

  • Land
  • 0.33 Acre
  • $2,121,212 per Acre

  Last Sold Summary

  • 36% Below List Price
  • 283 Days On Market

  Last Listing Agent Fred Flis REAL ESTATE MART

  7061 Longboat Dr E, 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
• 

  

  /64

  $874,900

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

  1050 Longboat Club Rd Unit 204, Longboat Key, FL 34228

  **Pirce Improvement ~ Motivated Seller** Step into the island lifestyle you’ve always imagined at Privateer North, located behind the gates of the Longboat Key Club. This CORNER residence with over 1,400 sq. ft. invites you to wake each morning to the sound of waves and natural light streaming through wide glass doors. Sip your coffee on the balcony as Gulf breezes drift in, and in the evening,

  Chris Carpenter COLDWELL BANKER SARASOTA CENT.

  1050 Longboat Club Rd Unit 204, Longboat Key, FL 34228
• 

  

  /25

  $8,000 per month

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft
  • Condo for Rent

  1925 Gulf of Mexico Dr Unit G8208, Longboat Key, FL 34228

  Beautiful Beachfront at SEAPLACE Condominium on LONGBOAT KEY. THREE bedroom turnkey FURNISHED READY FOR YOUR THRE MONTH OR LONGER STAY. Primary Bedroom has two full beds, queen in second bedroom, and two twins in the third bedroom. Spacious lanai with beautiful beach views. The Seaplace amenities include two large beachfront pools, fitness center, clubhouse, tennis courts and a great expansive

  Jane Hunter JENNETTE PROPERTIES INC

  1925 Gulf of Mexico Dr Unit G8208, Longboat Key, FL 34228
• 

  

  /83

  $700,000 Sold Mar 14, 2025

  5757 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,561 Sq Ft
  • Built 1974

  Last Sold Summary

  • 11% Below List Price
  • $448/SF
  • 170 Days On Market

  Current Estimated Value $658,478

  Last Listing Agent Josh Mills FINE PROPERTIES

  5757 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
• 

  

  /66

  Est $508,706 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

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

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

  

  /29

  $1,395,000

  • 3 Beds
  • 2 Baths
  • 1,941 Sq Ft

  100 Sands Point Rd Unit 323, Longboat Key, FL 34228

  Sands Point, a sought-after beachfront community within the gates of the Longboat Key Club, set on the gorgeous southern tip of Longboat Key. This newly remodeled 3BR/2BA, split plane with a large open living space to relax or entertain family and friends. The kitchen has been remarkably redone, featuring a breakfast bar, dining area, and custom solid surface countertops to complement the

  Marisa Marino BRIGHT REALTY

  100 Sands Point Rd Unit 323, Longboat Key, FL 34228
• 

  /2

  $3,450,000 Sold May 01, 2025

  608 Bayview Dr, Longboat Key, FL 34228

  • 3 Beds
  • 4 Baths
  • 3,199 Sq Ft
  • Built 2023

  Last Sold Summary

  • 4% Below List Price
  • $1,078/SF
  • 24 Days On Market

  Current Estimated Value $3,137,225

  Last Listing Agent Joel Schemmel DOUGLAS ELLIMAN

  608 Bayview Dr, Longboat Key, FL 34228
• 

  

  /59

  Est $3,308,105 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,413 Sq Ft

  603 Buttonwood Dr, Longboat Key, FL 34228

  603 Buttonwood Dr, Longboat Key, FL 34228
• 

  

  /47

  $1,900,000

  • Land
  • 0.37 Acre
  • $5,135,135 per Acre

  6549 Gulf of Mexico Dr, Longboat Key, FL 34228

  West side of Gulf of Mexico Dr and no busy street between you and the beach! Lot is cleared and ready with utilities at the lot. Build your dream home on this large lot (16,000 sq ft) just steps from the sugar sand beach on beautiful Longboat Key on the Gulf. This lot has the added bonus of backing up to Gulfside Road with a very short walk to beach access at the end of the street. Longboat Key

  Holly Switow PREMIER SOTHEBY'S INTERNATIONAL REALTY

  6549 Gulf of Mexico Dr, Longboat Key, FL 34228

Showing Results 521 - 560, Page 14 of 18