Longboat Key, FL Homes

• 

  

  

  /19

  $375,000

  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
• 

  

  

  /46

  $7,500 per month

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

  1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228

  Welcome to Pearl On The Key, your coastal sanctuary Professionally Managed by Gulf Coast Vacation Rentals, at Privateer, an exclusive beachfront community nestled on the pristine shores of Longboat Key. This 2-bedroom, 2-bathroom 7th floor condo offers breathtaking Gulf views from every room, elegant interiors, and access to resort-style amenities—making it the perfect destination for your next

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
• 

  

  /2

  $1,175,000 Sold Feb 12, 2025

  1901 Harbour Links Cir Unit 1, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft
  • Built 2001

  Last Sold Summary

  • 16% Below List Price
  • $495/SF
  • 28 Days On Market

  Current Estimated Value $1,118,768

  Last Listing Agent Michael Nink, PA MICHAEL SAUNDERS & COMPANY

  1901 Harbour Links Cir Unit 1, Longboat Key, FL 34228
• 

  

  

  /57

  Est $378,882 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

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

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

  

  

  /65

  $649,900

  • 2 Beds
  • 2 Baths
  • 1,376 Sq Ft

  4430 Exeter Dr Unit 108, Longboat Key, FL 34228

  Stunning Sarasota Bay Views from a Move-In-Ready First-Floor Spacious Corner Unit!Wake up to breathtaking, unobstructed Sarasota Bay vistas in this turnkey first-floor corner residence, designed with upscale Tommy Bahama–inspired flair. This exceptional home blends luxury island living with immediate rental potential, offering panoramic water views from both the primary and guest bedrooms,

  Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4430 Exeter Dr Unit 108, Longboat Key, FL 34228
• 

  

  /21

  $5,000 per month

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

  1912 Harbourside Dr Unit 603, Longboat Key, FL 34228

  Turnkey Townhouse on Longboat Key – Resort-Style Living! Live the island dream in this beautifully furnished 2-bedroom, 2.5-bathroom townhouse in the exclusive gated community of Fairway Bay. Located on picturesque Longboat Key, this bright and spacious home offers two ensuite bedrooms for ultimate comfort and privacy. Enjoy private beach access to the stunning Gulf of Mexico, take a dip

  Victoria Campbell LPT REALTY LLC

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

  /2

  $3,100,000 Sold Jan 07, 2026

  435 L Ambiance Dr Unit K506, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,820 Sq Ft
  • Built 1994

  Last Sold Summary

  • 6% Below List Price
  • $1,099/SF
  • 12 Days On Market

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  435 L Ambiance Dr Unit K506, Longboat Key, FL 34228
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  3710 Gulf of Mexico Dr Unit G-34, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit G-34, Longboat Key, FL 34228
• 

  

  /28

  $595,000

  • Land
  • 0.14 Acre
  • $4,250,000 per Acre

  641 Broadway St, Longboat Key, FL 34228

  Discover the irresistible charm of historic Longbeach Village and seize a rare opportunity to build your dream island home on Longboat Key. Welcome to the lowest priced vacant single-family parcel available on Longboat Key, an exceptional chance to design a custom residence just off the coast of Sarasota. This desired corner lot in the heart of the village offers flexible design possibilities,

  Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  641 Broadway St, Longboat Key, FL 34228
• 

  

  /48

  $13,500 per month

  • 3 Beds
  • 2 Baths
  • 1,871 Sq Ft
  • House for Rent

  613 Buttonwood Dr, Longboat Key, FL 34228

  Available for season 2026 This home has a split plan, generous size bedrooms and walk-in closets with a coastal theme flare. Open floor concept with formal dining. The kitchen as the heart of the home is expertly appointed with everything you will need for your home cooked meals. Head outside to the brand new beautiful pool and spa. One end features a soaking or sunbathing area, then step into

  Jennifer LeBlanc PRECISE REALTY CORP

  613 Buttonwood Dr, Longboat Key, FL 34228
• 

  /2

  $700,000 Sold Feb 11, 2025

  5310 Gulf of Mexico Dr Unit 11, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,014 Sq Ft
  • Built 1973

  Last Sold Summary

  • $690/SF
  • 3 Days On Market

  Current Estimated Value $632,454

  Last Listing Agent Chris Carpenter COLDWELL BANKER SARASOTA CENT.

  5310 Gulf of Mexico Dr Unit 11, Longboat Key, FL 34228
• 

  

  /79

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 568 Sq Ft

  90 Main Street Dr, Longboat Key, FL 34228

  90 Main Street Dr, Longboat Key, FL 34228
• 

  

  /58

  $2,400,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,154 Sq Ft

  1591 Gulf of Mexico Dr Unit 512, Longboat Key, FL 34228

  Fractional Ownership. Fractional Ownership Opportunity at The St. Regis Longboat Key. Each purchase includes complimentary Resort Membership, valued at $125,000, along with the added benefit of no annual dues (a $14,000 value) and no minimum annual expenditure requirements. The Resort Membership can be enjoyed year-round, providing exceptional value and convenience to owners. For 2025, fee for

  Michael Moulton MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 512, Longboat Key, FL 34228
• 

  

  /23

  $5,000 per month

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

  1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228

  Turnkey Townhouse on Longboat Key – Resort-Style Living!Live the island dream in this beautifully furnished 2-bedroom, 2.5-bathroom townhouse in the exclusive gated community of Fairway Bay. Located on picturesque Longboat Key, this bright and spacious home offers two ensuite bedrooms for ultimate comfort and privacy.Enjoy private beach access to the stunning Gulf of Mexico, take

  Victoria Campbell LPT REALTY LLC

  1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228
• 

  /2

  $875,000 Sold Feb 26, 2025

  5655 Gulf of Mexico Dr Unit D205, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 1975

  Last Sold Summary

  • 17% Below List Price
  • $687/SF
  • 81 Days On Market

  Current Estimated Value $818,967

  Last Listing Agent John Milkovich CHARLES RUTENBERG REALTY INC

  5655 Gulf of Mexico Dr Unit D205, Longboat Key, FL 34228
• 

  /2

  Est $1,275,318 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,491 Sq Ft

  2525 Gulf of Mexico Dr Unit 11B, Longboat Key, FL 34228

  2525 Gulf of Mexico Dr Unit 11B, Longboat Key, FL 34228
• 

  

  /17

  $275,000

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

  Easy in and out and close to parking! This 48 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 restaurants,

  Jennifer Wilson LBRE LLC

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

  

  /44

  $15,000 per month

  • 2 Beds
  • 2.5 Baths
  • 2,135 Sq Ft
  • Condo for Rent

  1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228

  Gorgeous gulf front vacation rental! Be the first to lease this wonderfully renovated 10th-story penthouse condominium in the Promenade on Longboat Key. This elegant residence offers two bedrooms and two and one half baths in over 2,100 square feet of living space. Fabulous views of the Gulf from every window. No expense was spared during this renovation; you will love the open floor plan with a

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
• 

  /2

  $375,000 Sold Apr 16, 2025

  4340 Falmouth Dr Unit 203, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,090 Sq Ft
  • Built 1969

  Last Sold Summary

  • 23% Below List Price
  • $344/SF
  • 219 Days On Market

  Current Estimated Value $382,118

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4340 Falmouth Dr Unit 203, Longboat Key, FL 34228
• 

  

  /45

  Est $1,349,660 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft

  1055 Gulf of Mexico Dr Unit 601, Longboat Key, FL 34228

  1055 Gulf of Mexico Dr Unit 601, Longboat Key, FL 34228
• 

  

  /94

  $549,900

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  4380 Exeter Dr Unit 204, Longboat Key, FL 34228

  Make your dreams come true with this beautiful waterfront condominium located at the popular Longboat Harbour resort! Enjoy gorgeous views of the water the moment you step in. This newly renovated 2BD/2BA second floor unit offers a roomy open floor plan with plenty of natural light, is being sold turnkey furnished. New Luxury Vinyl flooring and hurricane windows has been installed throughout. The

  Sandi Layfield MICHAEL SAUNDERS & COMPANY

  4380 Exeter Dr Unit 204, Longboat Key, FL 34228
• 

  

  /48

  $2,475 per month

  • 2 Beds
  • 2 Baths
  • 1,007 Sq Ft
  • Condo for Rent

  3810 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228

  GULF to BAY ACCESS! Beach Harbour Club Welcomes you home to Island living. New to the rental market is this second floor condo featuring 2 bedrooms, 2 bathrooms, dining room / family room combination and a full size washer / dryer located in the utility room. Beach Harbour Club is centrally located in the middle of Long Boat Key and this condo is a turn key fully furnished ANNUAL rental. There is

  Edward Whitaker PERLA'S PROPERTIES, LLC

  3810 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228
• 

  /2

  $2,900,000 Sold May 22, 2025

  3580 Fair Oaks Ln, Longboat Key, FL 34228

  • 5 Beds
  • 5.5 Baths
  • 4,167 Sq Ft
  • Built 1998

  Last Sold Summary

  • 17% Below List Price
  • $696/SF
  • 75 Days On Market

  Current Estimated Value $2,848,751

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  3580 Fair Oaks Ln, Longboat Key, FL 34228
• 

  /2

  Est $1,303,204 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,425 Sq Ft

  1965 Gulf of Mexico Dr Unit G5-201 & 203, Longboat Key, FL 34228

  1965 Gulf of Mexico Dr Unit G5-201 & 203, Longboat Key, FL 34228
• 

  

  /58

  $774,900 Open Sat 12PM - 2PM

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

  4805 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228

  NEW Best Price Opportunity Beach Front! Thoughtfully Updated with high- quality finishes! Experience refined Gulf-front living in this first-floor, Gulf-view residence with direct walk-out access to a private sandy beach. This pristine 2-bedroom, 2-bath home showcases an updated kitchen and spa-inspired baths, impact-resistant sliding doors that open seamlessly to two screened lanais, and a

  Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4805 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
• 

  

  /47

  $6,000 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 flooring in the

  Daniel Goldman COMPASS FLORIDA LLC

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

  /2

  $625,000 Sold Aug 07, 2025

  321 N Shore Rd Unit LOT ONLY, Longboat Key, FL 34228

  • Land
  • 0.14 Acre
  • $4,464,286 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 185 Days On Market

  Current Estimated Value $607,909

  Last Listing Agent Brian Leakeas COLDWELL BANKER REALTY

  321 N Shore Rd Unit LOT ONLY, Longboat Key, FL 34228
• 

  

  /49

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 680 Sq Ft

  3710 Gulf of Mexico Dr Unit B3, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit B3, Longboat Key, FL 34228
• 

  

  /90

  $1,695,000

  • 3 Beds
  • 2 Baths
  • 2,317 Sq Ft

  690 Jungle Queen Way, Longboat Key, FL 34228

  LONGBOAT KEY HOME WITH WATER VIEWS. BEST PRICE PER SQ FT! Attention boating enthusiasts! Sailboat waterfront home in Longboat Key with Florida's favorite southern exposure. Park your boat on the stationary, or floating dock with a boat lift, 10,000 pounds boat lift, NEW seawall 125 ft., stainless ladder and fillet station. The outdoor kitchen is paved with a cedar pergola, a firepit, kitchen

  Reeny Kaney RE/MAX ALLIANCE GROUP

  690 Jungle Queen Way, Longboat Key, FL 34228
• 

  

  /60

  $6,900 per month

  • 2 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • House for Rent

  535 Forest Way, Longboat Key, FL 34228

  Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by Gulf Coast Vacation Rentals, this chic, playful, and stylish 3-story, 2-bedroom, 2-bathroom townhome is nestled in one of the island’s most sought-after communities—offering a unique blend of tropical charm, resort-style amenities, and a peaceful coastal atmosphere.Step

  Andy Moore GULF COAST REALTY & MANAGEMENT

  535 Forest Way, Longboat Key, FL 34228
• 

  /2

  $580,000 Sold Jun 25, 2025

  681 Fox St, Longboat Key, FL 34228

  • 2 Beds
  • 1 Bath
  • 810 Sq Ft
  • Built 1964

  Last Sold Summary

  • 1% Above List Price
  • $716/SF
  • 4 Days On Market

  Current Estimated Value $571,280

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  681 Fox St, Longboat Key, FL 34228
• 

  

  /50

  Est $1,429,340 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,839 Sq Ft

  1485 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228

  1485 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228
• 

  

  /53

  $625,000

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  1935 Gulf of Mexico Dr Unit G7402, Longboat Key, FL 34228

  A must-see, this exceptional two-bedroom, two-bath penthouse is the only residence in Seaplace with no shared walls, offering unparalleled privacy and tranquility. Fully remodeled in 2019, the home features a designer kitchen with quartz countertops, custom cabinetry and premium appliances, seamlessly complemented by elegant soft grey laminate hardwood flooring throughout. A spacious lanai spans

  Rita Pogany PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1935 Gulf of Mexico Dr Unit G7402, Longboat Key, FL 34228
• 

  

  /57

  $7,500 per month

  • 3 Beds
  • 2.5 Baths
  • 2,490 Sq Ft
  • Condo for Rent

  380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228

  Available off season only. Welcome to coastal elegance at Tangerine Bay Club, where sweeping bay views set the stage for an exceptional lifestyle. This furnished residence captures the charm of a single-family home with its private courtyard entrance while offering all the benefits of resort-style community living. This comfortable three-bedroom retreat features a bright, open-concept layout, a

  Maureen Plichta STRINGER MANAGEMENT INC

  380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228
• 

  

  /69

  $705,000 Sold Mar 14, 2025

  4430 Exeter Dr Unit 103, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Below List Price
  • $612/SF
  • 35 Days On Market

  Current Estimated Value $651,846

  Last Listing Agent Kerre Allman MARCUS & COMPANY REALTY

  4430 Exeter Dr Unit 103, Longboat Key, FL 34228
• 

  /2

  Est $618,040 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,246 Sq Ft

  750 Saint Judes Dr N, Longboat Key, FL 34228

  750 Saint Judes Dr N, Longboat Key, FL 34228
• 

  

  /43

  $575,000

  • 2 Beds
  • 2 Baths
  • 1,257 Sq Ft

  2039 Gulf of Mexico Dr Unit G3207, Longboat Key, FL 34228

  THIS IS THE LARGEST 2 BEDROOM 2 BATH FLOOR PLAN IN SEAPLACE! Located on the second floor of the G3 building, this home is move in ready! The previous den has been enclosed for a proper bedroom and updated! The primary bedroom and bathroom have both been updated. Updated lighting, updated baseboards, no carpet, new hurricane rated sliders and windows! Plantation shutters are added for easy care

  Diane Fogo Harter MICHAEL SAUNDERS & COMPANY

  2039 Gulf of Mexico Dr Unit G3207, Longboat Key, FL 34228
• 

  

  /100

  $25,000 per month

  • 1 Bed
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228

  Welcome Serenity Oasis, your paradise at The Residences at the St.?Regis on Longboat Key—where luxury, elegance, and coastal charm converge in this stunning 1-bedroom, 2-bathroom condo. From the moment the elevator opens directly into your private entryway, you’ll be captivated by the exquisite design and attention to detail throughout this sophisticated retreat.The expansive living room

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228
• 

  /2

  $6,000,000 Sold Oct 03, 2025

  1591 Gulf of Mexico Dr Unit 511, Longboat Key, FL 34228

  • 2 Beds
  • 2.5 Baths
  • 3,130 Sq Ft
  • Built 2024

  Last Sold Summary

  • 14% Below List Price
  • $1,917/SF
  • 99 Days On Market

  Current Estimated Value $6,590,339

  Last Listing Agent Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 511, Longboat Key, FL 34228
• 

  /2

  Est $7,363,511 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 7,170 Sq Ft

  60 Lighthouse Point Dr, Longboat Key, FL 34228

  60 Lighthouse Point Dr, Longboat Key, FL 34228

Showing Results 281 - 320, Page 8 of 18