Longboat Key, FL Homes

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  $425,000

  2600 Harbourside Dr Unit L-05, Longboat Key, FL 34228

  Ask an L-dock boater, they will tell you it’s the best dock in the marina. Slip is near the seawall, just a few flat steps to your parked vehicle with easy in/out access. A 68 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina. This slip is one of the very few slips at the marina with a direct view of the Sarasota cityscape and colorfully lit Ringling bridge. Unlike most slips here, this does

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit L-05, Longboat Key, FL 34228
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  /31

  $6,750 Per Month

  • 2 Beds
  • 2 Baths
  • 1,341 Sq Ft
  • Condo for Rent

  914 Spanish Dr S Unit 76, Longboat Key, FL 34228

  Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the sought-after community of Spanish Main Yacht Club! This newly remodeled 2-bedroom, 2-bath residence features all brand-new furnishings and is ideally situated just steps from the marina and a picturesque seawall—perfect for peaceful mornings, frequent dolphin and manatee sightings, and stunning

  Geoff Scalera AUM FLORIDA REAL ESTATE LLC

  914 Spanish Dr S Unit 76, Longboat Key, FL 34228
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  $1,070,000 Sold Jul 31, 2025

  4401 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,314 Sq Ft
  • Built 1972

  Last Sold Summary

  • 30% Below List Price
  • $814/SF
  • 425 Days On Market

  Current Estimated Value $1,075,922

  Last Listing Agent Thomas Washburn BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  4401 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228
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  /42

  Est $871,480 Not Listed For Sale

  1085 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 1981

  1085 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  Last Sold Summary

  • 1% Above List Price
  • $621/SF
  • 123 Days On Market

  • Last Sold Price $865,000
  • Apr 19, 2024

  Last Listing Agent Ian Addy, PA Michael Saunders
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  /70

  $569,000 Pending

  • 2 Beds
  • 2 Baths
  • 933 Sq Ft

  2039 Gulf of Mexico Dr Unit G3108, Longboat Key, FL 34228

  Experience the best of coastal living in this beautifully updated ground-floor two-bedroom, two-bath residence located in Seaplace’s desirable G-3 building, offering a west-facing exposure with views of the Gulf of Mexico. Thoughtfully renovated, this condo features impact-rated sliding glass doors and hurricane shutters, providing both comfort and peace of mind. The inviting floor plan is ideal

  Michael Renick MANGROVE REALTY ASSOCIATES

  2039 Gulf of Mexico Dr Unit G3108, Longboat Key, FL 34228
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  /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
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  /2

  $2,100,000 Sold Jan 16, 2026

  5930 Gulf of Mexico Dr, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 2,570 Sq Ft
  • Built 1988

  Last Sold Summary

  • 22% Below List Price
  • $817/SF
  • 599 Days On Market

  Current Estimated Value $2,115,095

  Last Listing Agent Reid Murphy DEVELOPERS REALTY LBK, INC

  5930 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /19

  Est $291,060 Not Listed For Sale

  2800 Harbourside Dr Unit E-06, Longboat Key, FL 34228

  • Studio
  • 1,155 Sq Ft
  • Built 1982

  2800 Harbourside Dr Unit E-06, Longboat Key, FL 34228

  Last Sold Summary

  • 32% Above List Price
  • $190/SF
  • 5 Days On Market

  • Last Sold Price $220,000
  • Aug 10, 2023

  Last Listing Agent Jennifer Wilson LBRE LLC
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  /38

  $749,000

  • 3 Beds
  • 3.5 Baths
  • 2,513 Sq Ft

  350 Gulf of Mexico Dr Unit 234, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Set amid the lush, manicured grounds of Tangerine Bay, this exceptional two-story penthouse residence offers a rare blend of architectural volume, natural light, and water views. Mature tropical landscaping, tranquil lagoons, and resort-style amenities create a serene, park-like environment that feels both private and welcoming. Two terraces

  Ryan Ackerman COLDWELL BANKER REALTY

  350 Gulf of Mexico Dr Unit 234, Longboat Key, FL 34228
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  /40

  $3,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • House for Rent

  573 Spanish Dr N, Longboat Key, FL 34228

  NOW AVAILABLE STARTING JUNE 1, 2026 - BRAND NEW RENOVATED and TURNKEY FURNISHED available for ANNUAL LEASE ($3,500/MONTH) OR SEASONAL Jan - April ($5,500/MONTH). 6 MONTH MINUMUM RENTAL (OR INQUIRE ABOUT ANNUAL OPTION). ALL Utilities, Cable and Tax included. Come live the island life in this peaceful, fully detached villa nestled in the vibrant 55+ waterfront community of Spanish Main Yacht Club.

  Norma Mladineo COLDWELL BANKER REALTY

  573 Spanish Dr N, Longboat Key, FL 34228
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  $2,500,000 Sold May 23, 2025

  3606 Fair Oaks Place, Longboat Key, FL 34228

  • 4 Beds
  • 3 Baths
  • 3,842 Sq Ft
  • Built 2000

  Last Sold Summary

  • 23% Below List Price
  • $651/SF
  • 85 Days On Market

  Current Estimated Value $2,489,838

  Last Listing Agent Dennis Girard PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3606 Fair Oaks Place, Longboat Key, FL 34228
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  /18

  Est $338,497 Not Listed For Sale

  2600 Harbourside Dr Unit L-08, Longboat Key, FL 34228

  • Studio
  • Built 1983

  2600 Harbourside Dr Unit L-08, Longboat Key, FL 34228

  Last Sold Summary

  • 15% Below List Price
  • 381 Days On Market

  • Last Sold Price $400,000
  • Jul 21, 2023

  Last Listing Agent Jennifer Wilson LBRE LLC
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  /60

  $3,275,000

  • 3 Beds
  • 4.5 Baths
  • 3,273 Sq Ft

  1281 Gulf of Mexico Dr Unit 708, Longboat Key, FL 34228

  Welcome to an extraordinary corner residence at The Water Club where timeless elegance meets effortless coastal living on Longboat Key. Offering 3,275 square feet of beautifully designed interior space, this 3-bedroom, 4.5-bath condominium captures sweeping unobstructed expansive views of the Gulf of Mexico, glowing sunsets, Sarasota Bay, and the city skyline from nearly every room.

  Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  1281 Gulf of Mexico Dr Unit 708, Longboat Key, FL 34228
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  /22

  $7,000 Per Month

  • 1 Bed
  • 2 Baths
  • 1,244 Sq Ft
  • Condo for Rent

  655 Cedars Ct, Longboat Key, FL 34228

  AVAILABLE. 2026 SEASON.. 90 DAY MIN. ... Kick back and relax while on vacation in this marvelous townhouse located in Cedars East. Cedars East has all the amenities you desire including tennis, fitness center, beach access, swimming, community activities, tiki bar and restaurant on site. The unit has been fully upgraded and has a full gourmet kitchen with breakfast bar. Enjoy sweeping bay views

  Brenda Cozy COLDWELL BANKER REALTY

  655 Cedars Ct, Longboat Key, FL 34228
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  $535,000 Sold Oct 29, 2025

  640 Fox St, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1965

  Last Sold Summary

  • 21% Below List Price
  • $429/SF
  • 168 Days On Market

  Current Estimated Value $540,040

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  640 Fox St, Longboat Key, FL 34228
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  /2

  Est $656,187 Not Listed For Sale

  5260 Gulf of Mexico Dr Unit 412, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 1,453 Sq Ft
  • Built 1974

  5260 Gulf of Mexico Dr Unit 412, Longboat Key, FL 34228

  Last Sold Summary

  • 4% Above List Price
  • $434/SF
  • 45 Days On Market

  • Last Sold Price $630,000
  • Aug 30, 2024

  Last Listing Agent Eileen Gillen COLDWELL BANKER REALTY
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  /72

  $1,499,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,642 Sq Ft

  1445 Gulf of Mexico Dr Unit 501, Longboat Key, FL 34228

  This stunning corner penthouse spans over 2,800 sq. ft. and boasts breathtaking views of the Gulf, Bay, and city skyline. Key features include elegant stone floors, storm-resistant windows, custom cabinetry, skylights, raised ceilings, and indirect lighting. The kitchen offers a breakfast bar and an adjacent Solarium, perfect for enjoying your morning coffee while taking in both Gulf and city

  Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  1445 Gulf of Mexico Dr Unit 501, Longboat Key, FL 34228
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  /34

  $2,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

  2-bed, 2-bath seasonal or annual rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community’s private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
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  /2

  $625,000 Sold Dec 19, 2025

  4440 Exeter Dr Unit 206, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,376 Sq Ft
  • Built 1970

  Last Sold Summary

  • $454/SF
  • 4 Days On Market

  Current Estimated Value $627,864

  Last Listing Agent Kara Berger THE SHORELINE FL REALTY LLC

  4440 Exeter Dr Unit 206, Longboat Key, FL 34228
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  /28

  Est $1,237,213 Not Listed For Sale

  1125 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft
  • Built 1979

  1125 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228

  Last Sold Summary

  • 6% Above List Price
  • $639/SF
  • 118 Days On Market

  • Last Sold Price $1,162,500
  • Apr 30, 2024

  Last Listing Agent Jill Friedman COLDWELL BANKER REALTY
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  /19

  $225,000

  2600 Harbourside Dr Unit P-07, Longboat Key, FL 34228

  Quick access to dock you boat! Located just inside the marina on the east side. 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

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit P-07, Longboat Key, FL 34228
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  /30

  $8,721 Per Month

  • 2 Beds
  • 2 Baths
  • 1,461 Sq Ft
  • Condo for Rent

  2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228

  short stories AVAILABLE NOW... Stunning 2 bedroom 2 bath Longboat Key Gulf front condo with direct sweeping view of the Gulf of Mexico. Every evening enjoy breathtaking sunsets on your private balcony. Start your day with a leisurely stroll on the soft sand beach or take a refreshing dip in the pool. This condo is beautifully furnished and professionally decorated. King size bed in both bedrooms.

  Gerald Cunningham KELLER WILLIAMS ON THE WATER S

  2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
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  /2

  $1,800,000 Sold Jun 30, 2025

  612 Weston Pointe Ct, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,612 Sq Ft
  • Built 1993

  Last Sold Summary

  • 10% Below List Price
  • $689/SF
  • 80 Days On Market

  Current Estimated Value $1,767,424

  Last Listing Agent Cindy Schatzle COLDWELL BANKER REALTY

  612 Weston Pointe Ct, Longboat Key, FL 34228
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  /69

  Est $636,486 Not Listed For Sale

  4140 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,298 Sq Ft
  • Built 1973

  4140 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228

  Last Sold Summary

  • 8% Below List Price
  • $532/SF
  • 67 Days On Market

  • Last Sold Price $690,000
  • Jun 18, 2024

  Last Listing Agent Andrew Vac RE/MAX
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  /55

  $2,695,000

  • 3 Beds
  • 3.5 Baths
  • 3,382 Sq Ft

  2410 Harbourside Dr Unit 142, Longboat Key, FL 34228

  Positioned on the fourth floor of Marina Bay Building I, this fully renovated bayfront residence offers sweeping views across Sarasota Bay and the Harbourside Golf Course from one of Longboat Key’s most exclusive gated communities. Encompassing more than 3,300 square feet of interior living space, this three-bedroom, three-and-a-half-bath residence blends the scale and privacy of a single-family

  Roger Pettingell COLDWELL BANKER REALTY

  2410 Harbourside Dr Unit 142, Longboat Key, FL 34228
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  /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
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  /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
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  /48

  Est $967,173 Not Listed For Sale

  1485 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,366 Sq Ft
  • Built 1981

  1485 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  Last Sold Summary

  • 14% Above List Price
  • $622/SF
  • 7 Days On Market

  • Last Sold Price $849,000
  • Dec 04, 2023

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
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  /82

  $649,000

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

  1925 Gulf of Mexico Dr Unit G8302, Longboat Key, FL 34228

  Experience the Best of Gulfside Living at Seaplace on Longboat Key! Welcome to this beautifully maintained 2-bedroom, 2-bath residence offering the perfect blend of comfort, style, and coastal charm. This light-filled unit features an updated kitchen with rich wood cabinetry, granite countertops, and ample storage—ideal for both everyday living and entertaining. The spacious primary suite offers

  Michael Renick MANGROVE REALTY ASSOCIATES

  1925 Gulf of Mexico Dr Unit G8302, Longboat Key, FL 34228
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  /75

  $25,000 Per Month

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

  455 Longboat Club Rd Unit 1, Longboat Key, FL 34228

  This EXQUISITE 3 bedroom - 3 1⁄2 bath Penthouse has everything you will ever want in a Luxury Beachfront Condo; an open floor plan with plenty of space for living, dining and entertaining and custom appointments throughout. Natural light fills the condo from the moment you enter the foyer and a large skylight is overhead. Floor to ceiling windows frame the 14’ ceiling’s perimeter creating a

  Teresa Ribaudo JENNETTE PROPERTIES INC

  455 Longboat Club Rd Unit 1, Longboat Key, FL 34228
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  /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 $625,858

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  1930 Harbourside Dr Unit 136, Longboat Key, FL 34228
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  /59

  Est $852,193 Not Listed For Sale

  1065 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft
  • Built 1981

  1065 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

  Last Sold Summary

  • 5% Below List Price
  • $768/SF
  • 2 Days On Market

  • Last Sold Price $900,000
  • Dec 04, 2023

  Last Listing Agent Sharon Meier PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  /50

  $549,000 Pending

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

  1930 Harbourside Dr Unit 145, Longboat Key, FL 34228

  Under contract-accepting backup offers. Set on the 4th floor of Building 1 in Fairway Bay, this beautifully styled 2BR/2BA residence captures sweeping views across the mangroves, a navigable channel and Sarasota Bay beyond—creating a vibrant waterfront backdrop from nearly every room. Upon entry, engineered wood flooring draws your eye to a wall of glass at the rear of the residence, where

  Bruce Myer COLDWELL BANKER REALTY

  1930 Harbourside Dr Unit 145, Longboat Key, FL 34228
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  /57

  $19,975 Per Month

  • 4 Beds
  • 4 Baths
  • 4,236 Sq Ft
  • House for Rent

  5801 Gulf of Mexico Dr, Longboat Key, FL 34228

  Beach Access & Gulf Views From This Incredible Luxury Home on Longboat Key. Welcome to your own Gulf-front retreat on Longboat Key! This expansive 4-bedroom, 3-bath home offers over 4,200 square feet of living space designed for relaxation, entertaining, and soaking in stunning beach views. Inside, you’ll find an open living and dining area with vaulted ceilings and multi-level walls of windows

  Kevin Hase KEYRENTER SARASOTA PROPERTY MANAGEMENT

  5801 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /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 $1,346,466

  Last Listing Agent Doug Parks MICHAEL SAUNDERS & COMPANY

  2301 Gulf of Mexico Dr Unit 52, Longboat Key, FL 34228
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  /47

  Est $1,791,684 Not Listed For Sale

  2675 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,180 Sq Ft
  • Built 1979

  2675 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  Last Sold Summary

  • 17% Below List Price
  • $986/SF
  • 112 Days On Market

  • Last Sold Price $2,150,000
  • Jan 29, 2024

  Last Listing Agent Dianne Anderson COMPASS FLORIDA LLC
• 

  

  /27

  $525,000

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft

  5841 Gulf of Mexico Dr Unit 236, Longboat Key, FL 34228

  Enjoy relaxed coastal living in this turnkey furnished 1 bedroom, 1 bath residence located in the Gulf front community of Silver Sands Gulf Beach Resort. This first floor unit features an open living and dining layout that extends to a private screened lanai overlooking the communities tropical landscaping. Recent improvements include a new A/C system, new kitchen appliances, and a new hot water

  Stephen Strong MICHAEL SAUNDERS & COMPANY

  5841 Gulf of Mexico Dr Unit 236, Longboat Key, FL 34228
• 

  

  /12

  $9,000 Per Month

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

  2425 Gulf of Mexico Dr Unit 4E, Longboat Key, FL 34228

  LONGBOAT KEY, this 2 bed, 2 bath luxury condo with sweeping views of the GULF OF MEXICO, from every room, will truly capture you. Enjoy exquisite sunsets from any room or either private terrace. Interior design by award- winning international artist, with paintings & sculptures from the artist's private collection for your enjoyment. Granite counters & granite inlaid floor tiles in kitchen.

  Teresa Ribaudo JENNETTE PROPERTIES INC

  2425 Gulf of Mexico Dr Unit 4E, 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 $1,973,791

  Last Listing Agent Kaisen Mitchell COLDWELL BANKER REALTY

  4 Winslow Place, Longboat Key, FL 34228
• 

  

  /25

  Est $866,905 Not Listed For Sale

  4325 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft
  • Built 1975

  4325 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

  Last Sold Summary

  • 3% Above List Price
  • $632/SF
  • 146 Days On Market

  • Last Sold Price $845,000
  • Feb 29, 2024

  Last Listing Agent David Craig 1513 REALTY LLC

Showing Results 401 - 440, Page 11 of 18