Longboat Key, FL Homes

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  /94

  $22,750,000

  • 6 Beds
  • 9 Baths
  • 9,243 Sq Ft

  612 Juan Anasco Dr, Longboat Key, FL 34228

  Welcome to your private, gated estate on Longboat Key, where coastal luxury meets effortless sophistication. Boasting over 730 feet of water frontage, this stunning property offers panoramic views of Whitney Bayou and Harris Canal and provides the ultimate waterfront lifestyle. With 9,243 square feet of air-conditioned living space and a total of 21,562 square feet on over an acre of pristine

  Charles & Gabe Buky COLDWELL BANKER REALTY

  612 Juan Anasco Dr, Longboat Key, FL 34228
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  /38

  $4,000 per month

  • 2 Beds
  • 2 Baths
  • 1,031 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228

  Steps from the Sand – Luxury Beach Condo with Pool Access!Leave the snow behind and soak up the sun! This stunningly turnkey renovated 2-bedroom, 2-bathroom condo has everything you need for a carefree beach living– including a washer and dryer for sandy swimsuits!Enjoy private access to the shimmering Gulf beaches, relax by the heated pool, or paddle your cares away in the community

  nicoletta buonaccordo ALTIS REALTY

  3806 Gulf of Mexico Dr Unit C305, Longboat Key, FL 34228
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  /2

  $108,000 Sold Sep 30, 2025

  72 Main Street Dr, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 780 Sq Ft
  • Built 1965

  Last Sold Summary

  • $138/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  72 Main Street Dr, Longboat Key, FL 34228
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  /2

  Est $660,058 Not Listed For Sale

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

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

  5260 Gulf of Mexico Dr Unit 412, Longboat Key, FL 34228
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  /24

  $1,595,000 Pending

  • 2 Beds
  • 3.5 Baths
  • 2,143 Sq Ft

  3060 Grand Bay Blvd Unit 182, Longboat Key, FL 34228

  Soaring Sarasota Bay and Gulf of Mexico views from every room of this 8th floor residence at Grand Bay. This 2-bedroom + Den Biscayne floor plan is located on the corner of Building 1 and provides the perfect vantage-point for unobstructed views through floor-to-ceiling walls of glass. Relax on the wraparound terrace which is accessible from every room and offers dramatic sunsets over the Gulf of

  Ryan Ackerman COLDWELL BANKER REALTY

  3060 Grand Bay Blvd Unit 182, 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

  $1,465,000 Sold Aug 28, 2025

  501 Reclinata Dr, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,784 Sq Ft
  • Built 2002

  Last Sold Summary

  • 18% Below List Price
  • $526/SF
  • 160 Days On Market

  Current Estimated Value $1,506,191

  Last Listing Agent Barbara Najmy STARZ REAL ESTATE, LLC

  501 Reclinata Dr, Longboat Key, FL 34228
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  /28

  Est $1,057,581 Not Listed For Sale

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

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

  1125 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
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  /44

  $1,250,000

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft

  615 Buttonwood Dr, Longboat Key, FL 34228

  It's all about location. Just a short drive from Sarasota, Longboat Key offers unrivaled natural beauty in a coastal retreat. This home/land lot is a 1/3-acre with 100 feet of canal frontage on the desired south side of Longboat Key, and so close to the beach is about as good as it gets. The improvement can be inspected for remediation, and the generous lot features a healthy and substantial

  Walter Hackett PREMIER SOTHEBY'S INTERNATIONAL REALTY

  615 Buttonwood Dr, Longboat Key, FL 34228
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  /39

  $10,500 per month

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft
  • Condo for Rent

  4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228

  **BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease APRIL 2026** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath penthouse condo is located directly on the beach,

  Norma Mladineo COLDWELL BANKER REALTY

  4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
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  /2

  $1,400,000 Sold Dec 03, 2025

  3115 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,433 Sq Ft
  • Built 1974

  Last Sold Summary

  • 7% Below List Price
  • $977/SF
  • 6 Days On Market

  Last Listing Agent Ellen Kirkegaard PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3115 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  /69

  Est $574,385 Not Listed For Sale

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

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

  4140 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
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  /45

  $4,350,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 4.5 Baths
  • 4,138 Sq Ft

  610 Yardarm Ln, Longboat Key, FL 34228

  Experience elevated coastal living in this updated, elegantly styled waterfront residence in the coveted community of Country Club Shores on South Longboat Key. This beautifully maintained home has no history of flood or storm-water damage and offers peace of mind with a brand-new roof, all-new seawall, new dock, two boat lifts, updated mechanicals, and a private elevator—creating a true turn-key

  Nicholle McKiernan COLDWELL BANKER REALTY

  610 Yardarm Ln, Longboat Key, FL 34228
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  /35

  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Condo for Rent

  4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

  AVAILABLE Jan - Mar 2026!!! : 1 month minimum. Stunning Gulf views and incredible sunsets await you from this JUST completely renovated 2 bedroom, 2 bath condo on Longboat Key. You’ll fall in love with the contemporary soft-palette, coastal style! The open layout offers a seamless blend of kitchen, dining and living space, perfect for entertaining and relaxing. The gourmet kitchen features

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
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  /2

  $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 $1,060,385

  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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  /48

  Est $928,030 Not Listed For Sale

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

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

  1485 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
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  /57

  $2,195,000

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

  513 Outrigger Ln, Longboat Key, FL 34228

  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. Mature landscaping, a paver driveway and

  Bruce Myer COLDWELL BANKER REALTY

  513 Outrigger Ln, Longboat Key, FL 34228
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  /77

  $5,000 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 (1/6/26) PENDING HOA APPROVAL! LAST MINUTE CANCELLATION! 2 MONTH MINIMUM! 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
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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

  Last Listing Agent Reid Murphy DEVELOPERS REALTY LBK, INC

  5930 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /59

  Est $803,828 Not Listed For Sale

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

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

  1065 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228
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  /43

  $375,000

  • 2 Beds
  • 2 Baths
  • 1,046 Sq Ft

  3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228

  As of this New’s Years Eve 2025, there are only 14 options to become the happy owner of a place to call home on all of Longboat Key for under $400,000- and 9 of those options only have 1 bed/1bath! This is an opportune time to buy and this updated 2 bed/ 2 bath condo home with a view of Sarasota Bay is the one you want! Light and bright thru-out with consistent vinyl flooring, stainless steel

  Cindy Schatzle COLDWELL BANKER REALTY

  3806 Gulf of Mexico Dr Unit C310, Longboat Key, FL 34228
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  /71

  $15,000 per month

  • 3 Beds
  • 3 Baths
  • 1,710 Sq Ft
  • Condo for Rent

  1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  LOCATION, LOCATION, LOCATION!!! Gorgeous beach front PENTHOUSE condo available to rent in the sought after Longboat Key community of the Players Club. Enjoy views of the Gulf of Mexico, lush grounds and sparkling sandy beaches from the expansive terrace of this light and bright, corner unit, turnkey furnished condo. The property has three bedrooms, three bathrooms, living room/dining room

  C. Alison Hunter JENNETTE PROPERTIES INC

  1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
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  /2

  $752,000 Sold Apr 17, 2025

  1930 Harbourside Dr Unit 152, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,192 Sq Ft
  • Built 1982

  Last Sold Summary

  • 14% Below List Price
  • $631/SF
  • 123 Days On Market

  Current Estimated Value $700,722

  Last Listing Agent Rae Hayo AN ISLAND PLACE REALTY INC

  1930 Harbourside Dr Unit 152, Longboat Key, FL 34228
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  /47

  Est $1,758,623 Not Listed For Sale

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

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

  2675 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  /66

  $1,899,000 Open Sat 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 2,028 Sq Ft

  524 Ketch Ln, Longboat Key, FL 34228

  Discover the quintessential Longboat Key lifestyle in this classic masonry beach home located just “3” properties in from Sarasota Bay. Boasting 110 feet of canal frontage, your own private dock, a 7,500 lb. boatlift to complement this classic waterfront treasure it offers direct access for boating, fishing, and kayaking, with frequent visits from playful manatees and dolphins right in your

  Kathy Callahan MICHAEL SAUNDERS & COMPANY

  524 Ketch Ln, Longboat Key, FL 34228
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  /39

  $12,000 per month

  • 2 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • Condo for Rent

  4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228

  Longboat Key Gulf Front Vacation Rental! Gorgeous views from every window, 2 beds, 2 baths, fourth floor end unit in the wonderful boutique-style community of Tiffany Plaza. Look no further for your perfect vacation retreat, located directly on the Gulf of Mexico, this lovely condo has all you need. The updated kitchen has a center Island with breakfast bar, farm-style sink, and stainless steel

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
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  /2

  $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 $2,435,316

  Last Listing Agent Dennis Girard PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3606 Fair Oaks Place, Longboat Key, FL 34228
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  /25

  Est $804,576 Not Listed For Sale

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

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

  4325 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228
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  /55

  $659,000

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft

  3080 Grand Bay Blvd Unit 515, Longboat Key, FL 34228

  Defined by an exceptional indoor–outdoor connection, this 2BR/2BA Grand Bay residence offers a lifestyle centered on expansive terrace living and refined interiors. The living room is wrapped in floor-to-ceiling glass and opens to a wide wraparound veranda, creating an airy, resort-style ambiance that seamlessly blends indoors and out. The open living area flows naturally to the dining space and

  Bruce Myer COLDWELL BANKER REALTY

  3080 Grand Bay Blvd Unit 515, Longboat Key, FL 34228
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  /46

  $11,250 per month

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Condo for Rent

  1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  Available May-rest of 2025. Booked for Season 2026 February 1st to April 30th. Direct Beachfront, Longboat Key remodeled 2/2 Condo in Beachplace. Beautiful Beachplace is a gated community located on the southern end of Longboat Key, FL. Our unit is located in building nine, 4th floor, with a green belt area just to the north, the beach to the west, tennis courts to the East and few steps to the

  Jennifer LeBlanc PRECISE REALTY CORP

  1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
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  /2

  $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 $542,444

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  640 Fox St, Longboat Key, FL 34228
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  /29

  Est $1,172,305 Not Listed For Sale

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

  1105 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

  1105 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
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  /30

  $525,000

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  605 Sutton Place Unit 102, Longboat Key, FL 34228

  Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. The two-bedroom, two-bathroom unit features beautiful views of the Sarasota Bay, spacious living area, full-size kitchen with stainless steel appliances and granite countertops, dining area and 3 flat-screen TV’s. If the amenities on the interior of the condo aren’t enough – the community of Sutton Place

  Larry Starr SVN COMMERCIAL ADVISORY GROUP

  605 Sutton Place Unit 102, Longboat Key, FL 34228
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  /37

  $14,000 per month

  • 2 Beds
  • 2 Baths
  • 1,598 Sq Ft
  • Condo for Rent

  1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228

  Gulf Front Longboat Key Seasonal Rental! Located at the luxurious Promenade on Longboat Key, this sleek and modern 4th floor condo offers stunning gulf views, has two bedrooms, two baths, and is a true split plan. You will love the updated kitchen, with stainless appliances, granite counters, and sparkling tile backsplash. The living and dining areas have wood flooring, a nice contrast to the

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1211 Gulf of Mexico Dr Unit 405, 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

  Last Listing Agent Kara Berger THE SHORELINE FL REALTY LLC

  4440 Exeter Dr Unit 206, Longboat Key, FL 34228
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  /13

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  17 Main Street Dr, Longboat Key, FL 34228

  17 Main Street Dr, Longboat Key, FL 34228
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  /58

  $625,000

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

  2295 Gulf of Mexico Dr Unit 64S, Longboat Key, FL 34228

  PRICE REDUCED! Don’t miss this opportunity, schedule your showing today! Beachfront Living at Islander Club on Longboat Key Experience relaxed beachfront living at the Islander Club, one of Longboat Key’s most established and sought-after Gulf-front communities. Located directly on the Gulf of Mexico, this beautifully updated 2-bedroom, 2-bath residence offers true resort-style living in a

  Harold Kaufman PREFERRED SHORE LLC

  2295 Gulf of Mexico Dr Unit 64S, 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 $1,724,530

  Last Listing Agent Cindy Schatzle COLDWELL BANKER REALTY

  612 Weston Pointe Ct, Longboat Key, FL 34228
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  /32

  Est $891,442 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  210 Sands Point Rd Unit 2304, Longboat Key, FL 34228

  210 Sands Point Rd Unit 2304, Longboat Key, FL 34228

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