Longboat Key, FL Homes

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  /39

  $1,700,000

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft

  2425 Gulf of Mexico Dr Unit 14E, Longboat Key, FL 34228

  Amazing and Unobstructed 14th Floor Gulf and Beach Views! This is the perfectly remodeled unit you've been waiting for, with stunning sky views! Open floor plan, tile floors throughout, gorgeous open kitchen, and split bedroom floor plan. Just move right in and enjoy the views and amenities. The building has been completely remodeled. New roof, new windows, new railings, new pool, new storage

  Robert Delaney MICHAEL SAUNDERS & COMPANY

  2425 Gulf of Mexico Dr Unit 14E, Longboat Key, FL 34228
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  /59

  $10,000 per month

  • 3 Beds
  • 5 Baths
  • 2,908 Sq Ft
  • House for Rent

  3111 Bayou Sound, Longboat Key, FL 34228

  LOCATION, LOCATION, LOCATION. BEAUTIFUL TURNKEY FURNISHED SINGLE FAMILY HOME available in the sought after community of Bay Isles is available to rent. This lovely light, bright 3 bedroom plus 3 bathroom, two half bathroom home boasts 2,908 square feet, double primary bedrooms, living room/dining room combination, loft/den space and much much more. The home has been fully painted and newly

  C. Alison Hunter JENNETTE PROPERTIES INC

  3111 Bayou Sound, Longboat Key, FL 34228
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  /2

  $275,000 Sold Jun 16, 2025

  2600 Harbourside Dr Unit C-12, Longboat Key, FL 34228

  Last Sold Summary

  • 8% Below List Price
  • 23 Days On Market

  Current Estimated Value $262,613

  Last Listing Agent Jessica Hurley PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2600 Harbourside Dr Unit C-12, Longboat Key, FL 34228
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  /52

  Est $740,267 Not Listed For Sale

  4900 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,561 Sq Ft
  • Built 1975

  4900 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  Last Sold Summary

  • 10% Below List Price
  • $525/SF
  • 66 Days On Market

  Last Sold Price $819,000

  Last Listing Agent Michael Albano, PA COLDWELL BANKER REALTY
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  /44

  $1,395,000

  • 2 Beds
  • 2.5 Baths
  • 1,569 Sq Ft

  1485 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  Coastal elegance meets effortless island living at The Player’s Club on Longboat Key. This 2-bedroom, 2.5-bath Gulf-front residence located in building #1 offers direct Gulf views from the private balcony, where nightly sunsets paint the sky in unforgettable color, your front-row seat to paradise. Located in a guard-gated, low-density community with 560 feet of private beachfront, this property

  Rinat Sikdar COLDWELL BANKER REALTY

  1485 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
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  /24

  $10,500 per month

  • 2 Beds
  • 2 Baths
  • 1,651 Sq Ft
  • Condo for Rent

  2525 Gulf of Mexico Dr Unit 12-F, Longboat Key, FL 34228

  Stunning Gulf-Front Condo with Breathtaking Views at Islands West! Experience the epitome of coastal living in this exquisite 2-bedroom, 2-bathroom condominium on the 12th floor of Islands West, where full Gulf views become a part of your daily life. This beautifully furnished unit is not just a rental; it’s a lifestyle choice that offers you the chance to wake up to the soothing sounds of waves

  Jane Hunter JENNETTE PROPERTIES INC

  2525 Gulf of Mexico Dr Unit 12-F, Longboat Key, FL 34228
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  /2

  $738,000 Sold Oct 14, 2025

  5055 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,484 Sq Ft
  • Built 1973

  Last Sold Summary

  • 33% Below List Price
  • $497/SF
  • 186 Days On Market

  Current Estimated Value $725,669

  Last Listing Agent Bo Fuller FULLER GROUP

  5055 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228
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  /28

  Not Listed For Sale

  3710 Gulf of Mexico Dr Unit A19, Longboat Key, FL 34228

  • 2 Beds
  • 1.5 Baths
  • 720 Sq Ft
  • Built 2023

  3710 Gulf of Mexico Dr Unit A19, Longboat Key, FL 34228

  Last Sold Summary

  • $694/SF
  • 2 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC
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  /55

  $929,000

  • 3 Beds
  • 2 Baths
  • 2,105 Sq Ft

  2110 Harbourside Dr Unit 547, Longboat Key, FL 34228

  Experience refined coastal living behind the gates of the prestigious Bay Isles. This beautifully appointed 3-bedroom, 2-bath residence in The Atrium offers an exceptional blend of elegance, comfort, and convenience just minutes from St. Armands Circle and vibrant downtown Sarasota. Designed for effortless living and entertaining, the open floor plan showcases high ceilings, a sophisticated blend

  Mimi Kruk MICHAEL SAUNDERS & COMPANY

  2110 Harbourside Dr Unit 547, Longboat Key, FL 34228
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  /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
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  /2

  $310,000 Sold Apr 14, 2025

  549 Sutton Place, Longboat Key, FL 34228

  • 2 Beds
  • 1.5 Baths
  • 1,008 Sq Ft
  • Built 1972

  Last Sold Summary

  • 22% Below List Price
  • $308/SF
  • 89 Days On Market

  Current Estimated Value $486,779

  Last Listing Agent Malihe Karimi MICHAEL SAUNDERS & COMPANY

  549 Sutton Place, Longboat Key, FL 34228
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  /43

  Est $623,819 Not Listed For Sale

  4960 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1975

  4960 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

  Last Sold Summary

  • 5% Below List Price
  • $494/SF
  • 163 Days On Market

  Last Sold Price $655,000

  Last Listing Agent Andree Huffine COLDWELL BANKER REALTY
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  /48

  $1,425,000

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

  2525 Gulf of Mexico Dr Unit 6B, Longboat Key, FL 34228

  Ultra-luxury, fully remodeled Gulf-front residence on Longboat Key. This sixth-floor, move-in ready condo at Islands West comes furnished and showcases imported Italian cabinetry, level 5 drywall, carrara marble flooring, aqua quartz countertops and steam shower. All-new hurricane-impact windows and doors, including floor-to-ceiling glass in both bedrooms, frame sweeping water views and a

  Nancy Endara PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2525 Gulf of Mexico Dr Unit 6B, Longboat Key, FL 34228
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  /26

  $9,800 per month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  640 Broadway St, Longboat Key, FL 34228

  Step into living history in the heart of Historic Longbeach Village. This exceptional property occupies land that was part of Civil War veteran Thomas Mann’s 144-acre homestead, where in 1891 he built the island’s first permanent residence just steps away. This serene corner lot is where Longboat Key truly began! Fully rebuilt and elevated in 2025 to the highest modern standards after the 2024

  Christina Vescovo LPT REALTY, LLC

  640 Broadway St, Longboat Key, FL 34228
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  /2

  $1,825,000 Sold Aug 26, 2025

  3322 Bayou Rd, Longboat Key, FL 34228

  • 5 Beds
  • 3 Baths
  • 3,441 Sq Ft
  • Built 1982

  Last Sold Summary

  • 20% Below List Price
  • $530/SF
  • 111 Days On Market

  Current Estimated Value $1,827,507

  Last Listing Agent Debra Pitell-Hauge MICHAEL SAUNDERS & COMPANY

  3322 Bayou Rd, Longboat Key, FL 34228
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  /25

  Not Listed For Sale

  3710 Gulf of Mexico Dr Unit D22, Longboat Key, FL 34228

  • 2 Beds
  • 1 Bath
  • 676 Sq Ft
  • Built 1991

  3710 Gulf of Mexico Dr Unit D22, Longboat Key, FL 34228

  Last Sold Summary

  • $422/SF
  • 141 Days On Market

  Last Sold Price $285,000

  Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC
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  /66

  $1,030,000

  • 2 Beds
  • 2 Baths
  • 1,293 Sq Ft

  615 Dream Island Rd Unit 202, Longboat Key, FL 34228

  Bring your boat to Longboat Key. Fully furnished second floor corner unit with boat dock and stunning views of the Sarasota Bay in beautiful Harbor Villa Club. This beautifully renovated 2-bedroom, 2-bathroom condo is an incredible opportunity to live right on the Sarasota bay with 180 degree breathtaking water views. This single level, corner unit has plenty of natural light and has been updated

  Greg Orquera ORQUERA FLORIDA INVESTMENTS

  615 Dream Island Rd Unit 202, Longboat Key, FL 34228
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  /33

  $14,400 per month

  • 2 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • House for Rent

  701 Broadway St, Longboat Key, FL 34228

  This charming single-story residence is a meticulous rebuild with an open-concept great room featuring high ceilings, abundant natural light, and a gourmet kitchen equipped with stainless steel appliances and a gas range. The private, fully fenced backyard offers a lagoon style heated swimming pool, separate hot tub, lush tropical landscaping, and the soothing sound of swaying palms. Completely

  Christina Vescovo LPT REALTY, LLC

  701 Broadway St, Longboat Key, FL 34228
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  /2

  $2,200,000 Sold Jan 19, 2026

  548 Ketch Ln, Longboat Key, FL 34228

  • 2 Beds
  • 3 Baths
  • 2,273 Sq Ft
  • Built 1972

  Last Sold Summary

  • $968/SF
  • 0 Days On Market

  Current Estimated Value $2,718,282

  Last Listing Agent Kathy Callahan MICHAEL SAUNDERS & COMPANY

  548 Ketch Ln, Longboat Key, FL 34228
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  /56

  Est $647,645 Not Listed For Sale

  225 Sands Point Rd Unit 7304, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 642 Sq Ft
  • Built 1983

  225 Sands Point Rd Unit 7304, Longboat Key, FL 34228

  Last Sold Summary

  • 14% Below List Price
  • $1,168/SF
  • 9 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Reid Murphy DEVELOPERS REALTY LBK, INC
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  /35

  $1,299,000

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

  1055 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  This direct Gulf-front residence at Beachplace offers an extraordinary opportunity to enjoy the very best of Longboat Key’s beachfront lifestyle. Perfectly positioned to capture unobstructed views of the Gulf of Mexico, this furnished two-bedroom home combines a serene coastal retreat with strong rental potential—producing an average of $70,000 annually in gross rentals. Whether you envision it

  Roger Pettingell COLDWELL BANKER REALTY

  1055 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
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  /23

  $5,000 per month

  • 1 Bed
  • 1.5 Baths
  • 725 Sq Ft
  • Condo for Rent

  4401 Gulf of Mexico Dr Unit 703, Longboat Key, FL 34228

  Desirable Furnished One Bedroom 1 1/2 Bathroom Condo on Longboat Key. It is on the 7th floor with a 20 ft lanai that has an outstanding view of the beach and the Gulf of America. The building is one of the closest to the beach with access within few feet of the building, is well managed, has a salt water heated pool & recreational area with gas grill. There is an exercise center, public kitchen,

  David Gardner PINEBROOK IRONWOOD REALTY

  4401 Gulf of Mexico Dr Unit 703, Longboat Key, FL 34228
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  /2

  $675,000 Sold Feb 17, 2026

  723 Bayport Way Unit 723, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,486 Sq Ft
  • Built 1983

  Last Sold Summary

  • 1% Below List Price
  • $454/SF
  • 6 Days On Market

  Current Estimated Value $679,976

  Last Listing Agent Antonietta Car KELLER WILLIAMS SUBURBAN TAMPA

  723 Bayport Way Unit 723, Longboat Key, FL 34228
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  /51

  Est $336,698 Not Listed For Sale

  104 Twin Shores Blvd, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 741 Sq Ft
  • Built 1950

  104 Twin Shores Blvd, Longboat Key, FL 34228

  Last Sold Summary

  • 1% Below List Price
  • $459/SF
  • 671 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Marni Hayden CHROME REALTY LLC
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  /52

  $975,000

  • 2 Beds
  • 2 Baths
  • 961 Sq Ft

  5125 Gulf of Mexico Dr Unit 7, Longboat Key, FL 34228

  Nestled in the heart of Longboat Key, this exceptional two-bedroom, two-bathroom beachfront condo offers a rare blend of luxury, comfort, and high rental potential. Situated within the meticulously maintained Seagrape Inn, this turnkey furnished unit is an investor’s dream, boasting a potential gross annual revenue of $108,000 and a net operating income of $66,000. The Seagrape Inn's lush

  Patrick Brogley KELLER WILLIAMS ON THE WATER S

  5125 Gulf of Mexico Dr Unit 7, Longboat Key, FL 34228
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  /35

  $3,000 per month

  • 2 Beds
  • 2 Baths
  • 1,085 Sq Ft
  • Condo for Rent

  3808 Gulf of Mexico Dr Unit 211, Longboat Key, FL 34228

  2-bed, 2-bath seasonal 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 around on

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3808 Gulf of Mexico Dr Unit 211, Longboat Key, FL 34228
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  /2

  $760,000 Sold Jan 16, 2026

  7155 Gulf of Mexico Dr Unit 22, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,170 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Below List Price
  • $650/SF
  • 19 Days On Market

  Current Estimated Value $766,208

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  7155 Gulf of Mexico Dr Unit 22, Longboat Key, FL 34228
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  /42

  Est $348,749 Not Listed For Sale

  102 Twin Shores Blvd, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 809 Sq Ft
  • Built 1950

  102 Twin Shores Blvd, Longboat Key, FL 34228

  Last Sold Summary

  • 16% Below List Price
  • $513/SF
  • 90 Days On Market

  Last Sold Price $415,000

  Last Listing Agent Allison Menke BRIGHT REALTY
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  /76

  $2,695,000

  • 5 Beds
  • 5 Baths
  • 4,510 Sq Ft

  3408 Fair Oaks Ln, Longboat Key, FL 34228

  Elegant 5BR/5BA home in the gated community of Corey’s Landing within Bay Isles on Longboat Key. With over 4,500 sq ft, this spacious two-story residence offers open living areas, soaring ceilings, and refined design for both comfort and style. The light-filled great room with 22-ft ceilings opens to a gourmet kitchen with stone countertops, breakfast bar, and stainless-steel appliances. The

  Bruce Myer COLDWELL BANKER REALTY

  3408 Fair Oaks Ln, 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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  $2,700,400 Sold Jan 15, 2026

  598 Lyons Ln, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,276 Sq Ft
  • Built 2021

  Last Sold Summary

  • 8% Below List Price
  • $1,186/SF
  • 35 Days On Market

  Current Estimated Value $2,688,280

  Last Listing Agent Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  598 Lyons Ln, Longboat Key, FL 34228
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  /60

  Est $773,589 Not Listed For Sale

  4960 Gulf of Mexico Dr Unit 306, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,523 Sq Ft
  • Built 1975

  4960 Gulf of Mexico Dr Unit 306, Longboat Key, FL 34228

  Last Sold Summary

  • 21% Below List Price
  • $640/SF
  • 20 Days On Market

  Last Sold Price $975,000

  Last Listing Agent Debby McCaig COLDWELL BANKER REALTY
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  /57

  $2,195,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,162 Sq Ft

  513 Outrigger Ln, Longboat Key, FL 34228

  Under contract-accepting backup offers. Set at the quiet end of the canal, with open water just beyond the dock and the beach only minutes away, this Country Club Shores home offers an easy, comfortable waterfront lifestyle on South Longboat Key. The 4-bedroom, 3-bath residence spans approximately 2,162 square feet and has been thoughtfully updated to feel open, inviting, and easy to live in.

  Bruce Myer COLDWELL BANKER REALTY

  513 Outrigger Ln, Longboat Key, FL 34228
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  /83

  $20,000 per month

  • 1 Bed
  • 1.5 Baths
  • 1,721 Sq Ft
  • Condo for Rent

  1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

  The Residences at The St. Regis Longboat Key mark the debut of a truly iconic address — the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico. Welcome home to the legendary service and sophistication of St. Regis, paired with the tranquil allure of a seaside retreat on the exclusive barrier island of Longboat Key, Florida. Step inside to beautifully

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
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  /2

  $925,000 Sold Jul 10, 2025

  5055 Gulf of Mexico Dr Unit 232, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 1973

  Last Sold Summary

  • 27% Below List Price
  • $570/SF
  • 25 Days On Market

  Current Estimated Value $977,551

  Last Listing Agent Nathan Mathers PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5055 Gulf of Mexico Dr Unit 232, Longboat Key, FL 34228
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  /53

  Est $651,810 Not Listed For Sale

  4401 Gulf of Mexico Dr Unit 503, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 896 Sq Ft
  • Built 1972

  4401 Gulf of Mexico Dr Unit 503, Longboat Key, FL 34228

  Last Sold Summary

  • 11% Below List Price
  • $815/SF
  • 113 Days On Market

  Last Sold Price $730,000

  Last Listing Agent Michael Nink, PA Michael Saunders
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  /49

  $3,175,000

  • 4 Beds
  • 2.5 Baths
  • 2,550 Sq Ft

  595 Bowsprit Ln, Longboat Key, FL 34228

  Longboat Key Waterfront Perfection! Experience the ultimate coastal lifestyle in this 4-bedroom, 2.5-bath home, effective year 2016, in the prestigious Country Club Shores community—just three homes from Sarasota Bay with quick access to the Gulf of Mexico. Boater’s paradise with two boat lifts (20,000 lb and 7,000 lb), a new seawall, and private dock complete with a custom fish cleaning station

  Melissa Gissinger MICHAEL SAUNDERS & COMPANY

  595 Bowsprit Ln, Longboat Key, FL 34228
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  /31

  $10,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,957 Sq Ft
  • Condo for Rent

  1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Luxury Living meets Modern Coastal at Gulf Front Haven, a beautifully updated, modern, ocean view floorplan that sits right on the beach at Longboat Key, one of the Gulf Coasts Premier Living Areas! This home is located right in the heart of the Players Club, one of Longboat Keys most luxurious communities with all the amenities to make your stay great!! The condo is located on the 3rd Floor with

  Brad Wilson M&M PROPERTY MANAGEMENT GROUP

  1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  /2

  $350,000 Sold Sep 15, 2025

  655 Spanish Way, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,241 Sq Ft
  • Built 1968

  Last Sold Summary

  • 11% Below List Price
  • $282/SF
  • 74 Days On Market

  Current Estimated Value $346,072

  Last Listing Agent Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY

  655 Spanish Way, Longboat Key, FL 34228
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  /80

  Est $3,001,660 Not Listed For Sale

  1241 Gulf of Mexico Dr Unit 707, Longboat Key, FL 34228

  • 2 Beds
  • 4.5 Baths
  • 2,965 Sq Ft
  • Built 1996

  1241 Gulf of Mexico Dr Unit 707, Longboat Key, FL 34228

  Last Sold Summary

  • 12% Below List Price
  • $1,147/SF
  • 17 Days On Market

  Last Sold Price $3,400,000

  Last Listing Agent Michael Moulton Michael Saunders

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