Longboat Key, FL Homes

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  $2,599,000

  • 3 Beds
  • 3.5 Baths
  • 2,780 Sq Ft

  455 Longboat Club Rd Unit 408, Longboat Key, FL 34228

  Behind the gates of the renowned Longboat Key Club, this stunning residence at The Pierre offers a rare opportunity to enjoy elevated coastal living paired with the ease and sophistication of a true resort lifestyle. Completely renovated by Brista Homes, this 3-bedroom, 3.5-bath condominium is spacious, refined, and thoughtfully curated, with three oversized bedrooms each featuring a private

  Gina Ursini BRISTA REALTY LLC

  455 Longboat Club Rd Unit 408, Longboat Key, FL 34228
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  $7,800 per month

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

  4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  SEASONAL: Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, in unit washer/dryer, large walk-in closets and covered parking. The Master suite

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  $3,350,000 Sold Nov 21, 2025

  2333 Gulf of Mexico Dr Unit 1A3, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 3,060 Sq Ft
  • Built 1997

  Last Sold Summary

  • 21% Below List Price
  • $1,095/SF
  • 92 Days On Market

  Last Listing Agent Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

  2333 Gulf of Mexico Dr Unit 1A3, Longboat Key, FL 34228
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 880 Sq Ft

  3710 Gulf of Mexico Dr Unit G1, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit G1, Longboat Key, FL 34228
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  /57

  $8,250,000

  • 4 Beds
  • 4.5 Baths
  • 4,630 Sq Ft

  5005 Gulf of Mexico Dr Unit 4, Longboat Key, FL 34228

  Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes.Steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 square feet of refined interiors on the main living floors together with multiple large lanais and

  Reid Murphy DEVELOPERS REALTY LBK, INC

  5005 Gulf of Mexico Dr Unit 4, Longboat Key, FL 34228
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  /46

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft
  • Condo for Rent

  2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228

  RARELY AVAILABLE! This absolutely gorgeous fully furnished 2BR/2BA Condo at Islander Club – Just steps from the Beach! Start living the island lifestyle in this beautifully updated, furnished 2-bedroom, 2-bath condo at the Islander Club on South Longboat Key! This turnkey rental is ready for immediate enjoyment—just bring your suitcase. Enjoy a bright, open layout with floor-to-ceiling hurricane

  Michele Conn PREFERRED SHORE LLC

  2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228
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  /2

  $535,000 Sold Apr 22, 2025

  660 Fox St, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,234 Sq Ft
  • Built 1968

  Last Sold Summary

  • 11% Below List Price
  • $434/SF
  • 24 Days On Market

  Current Estimated Value $527,144

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  660 Fox St, Longboat Key, FL 34228
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  Est $3,628,843 Not Listed For Sale

  • 3 Beds
  • 5 Baths
  • 3,400 Sq Ft

  1241 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

  1241 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228
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  $629,000

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  5260 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

  Welcome to your tropical retreat on Longboat Key! This newly renovated 2-bedroom, 2-bath ground-floor larger end unit, with additional windows blends light coastal charm with modern comfort in a sought-after Gulf-to-Bay community. Thoughtful upgrades include neutral tile flooring throughout (no carpet), crown molding, upgraded baseboards, fresh interior paint, impact-rated PGT windows and

  Debbie McHardy COLDWELL BANKER REALTY

  5260 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228
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  /85

  $3,000 per month

  • 2 Beds
  • 2 Baths
  • 928 Sq Ft
  • Condo for Rent

  1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228

  LONGBOAT KEY "SEAPLACE" CONDOMINIUM LOCATED ON THE GULF SIDE. AVAILABLE DEC 2025 & JAN 2026 AT $3,000/MONTH. UTILITIES INCLUDED. 2 MONTH MINIMUM REQUIRED PER HOA.BOOKED FOR FEB-APRIL 2026. Immaculate, Turnkey Furnished 2 bedrooms/2-bathroom condo on the 4th floor, located in the sought after Seaplace, a resort style community on the beautiful Barrier Island of Longboat Key. Upon entering the

  Chrissie Cummings JENNETTE PROPERTIES INC

  1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
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  $1,205,000 Sold Apr 07, 2025

  3060 Grand Bay Blvd Unit 162, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,143 Sq Ft
  • Built 1994

  Last Sold Summary

  • 9% Below List Price
  • $562/SF
  • 70 Days On Market

  Current Estimated Value $1,157,795

  Last Listing Agent Judy Mitchell PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3060 Grand Bay Blvd Unit 162, Longboat Key, FL 34228
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  /80

  Est $1,395,539 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,462 Sq Ft

  2020 Harbourside Dr Unit 434/435, Longboat Key, FL 34228

  2020 Harbourside Dr Unit 434/435, Longboat Key, FL 34228
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  /20

  $995,000

  • Land
  • 0.16 Acre
  • $6,218,750 per Acre

  6800 Longboat Dr S, Longboat Key, FL 34228

  This lot is located in The Preserve at Longbeach with plans and design already to go, an exclusive enclave of 12 new homes, light filled and luxurious contemporary homes. Refinement meets relaxation at the north end of LBK in Longbeach Village - where beach-to-bay access with waterfront amenities, al fresco dining, multiple kayak launch points, a neighborhood boat dock and ramp, and a

  Reid Murphy DEVELOPERS REALTY LBK, INC

  6800 Longboat Dr S, Longboat Key, FL 34228
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  /45

  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,133 Sq Ft
  • Condo for Rent

  3802 Gulf of Mexico Dr Unit 207, 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

  3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
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  $530,000 Sold Apr 28, 2025

  709 Bayport Way Unit 709, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1980

  Last Sold Summary

  • 27% Below List Price
  • $379/SF
  • 334 Days On Market

  Current Estimated Value $506,540

  Last Listing Agent Roger Clyne PREFERRED SHORE LLC

  709 Bayport Way Unit 709, Longboat Key, FL 34228
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  /29

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 693 Sq Ft

  3710 Gulf of Mexico Dr Unit E23, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit E23, Longboat Key, FL 34228
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  $424,900

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

  576 Sutton Place, Longboat Key, FL 34228

  ONE YEAR of HOA fees to be paid by the Seller for an acceptable offer with a qualified buyer - $1700+ a month . Experience effortless coastal living in this lovely 2-bedroom, 2-bath end-unit bayside villa offering the highly sought-after Bay-to-Beach lifestyle on Longboat Key. Beautifully appointed and sold turnkey, this ground-floor residence is truly Martha Stewart–perfect—move-in ready and

  Kathy Callahan MICHAEL SAUNDERS & COMPANY

  576 Sutton Place, Longboat Key, FL 34228
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  /45

  $10,995 per month

  • 3 Beds
  • 2.5 Baths
  • 2,396 Sq Ft
  • House for Rent

  2339 Harbour Oaks Dr, Longboat Key, FL 34228

  Seasonal/short term rental on Longboat Key Beautifully renovated 3 bedroom 2 1/2 bathroom villa right on the golf course in prestigious, guard gated, Bay Isles. This spacious light filled delight has vaulted ceilings with sky lights, and new high impact windows and doors. The open floor plan is perfect for family time and entertaining. The kitchen is very large and has solid cherry wood

  Henry Rossi RENT SARASOTA

  2339 Harbour Oaks Dr, Longboat Key, FL 34228
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  /2

  $711,000 Sold Mar 18, 2025

  4540 Gulf of Mexico Dr Unit PH1, Longboat Key, FL 34228

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

  Last Sold Summary

  • 8% Below List Price
  • $455/SF
  • 34 Days On Market

  Current Estimated Value $670,841

  Last Listing Agent Marcela Terrell COLDWELL BANKER REALTY

  4540 Gulf of Mexico Dr Unit PH1, Longboat Key, FL 34228
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  /69

  Est $789,735 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,498 Sq Ft

  5270 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228

  5270 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228
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  /39

  $1,550,000

  • 2 Beds
  • 2 Baths
  • 1,551 Sq Ft

  1701 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

  AQUARIUS CLUB – This renovated fourth-floor condo presents a rare opportunity to own the ultimate beachfront retreat on the coveted south end of Longboat Key, where ownership includes a complimentary social membership to the adjacent brand-new St. Regis Resort. Nestled within an intimate boutique community of just 58 residences, the Aquarius Club recently underwent extensive renovations led by

  Doug Parks MICHAEL SAUNDERS & COMPANY

  1701 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
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  $18,000 per month

  • 2 Beds
  • 2.5 Baths
  • 2,143 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228

  2027 Season Rental Rate will be $24,500. The Residences at The St. Regis Longboat Key offer an exceptional blend of ultra-luxury living and world-class resort amenities on the pristine shores of the Gulf of Mexico. This exclusive beachfront community features exquisitely designed residences with soaring ceilings, floor-to-ceiling glass doors, and panoramic sunrise-to-sunset views. The gourmet

  Melissa Gissinger MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
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  $739,000 Sold Jun 18, 2025

  1945 Gulf of Mexico Dr Unit M2313, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft
  • Built 1978

  Last Sold Summary

  • $584/SF
  • 1 Day On Market

  Current Estimated Value $701,994

  Last Listing Agent Bruce Meyer MICHAEL SAUNDERS & COMPANY

  1945 Gulf of Mexico Dr Unit M2313, Longboat Key, FL 34228
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  /18

  Est $220,367 Not Listed For Sale

  • Studio
  • 1,155 Sq Ft

  2600 Harbourside Dr Unit C-10, Longboat Key, FL 34228

  2600 Harbourside Dr Unit C-10, Longboat Key, FL 34228
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  $3,450,000

  • 3 Beds
  • 3.5 Baths
  • 2,634 Sq Ft

  435 L Ambiance Dr Unit J704, Longboat Key, FL 34228

  Rarely available, this 7th floor, 3 bedroom, 3 bath condo with perfect east/west views offers total privacy. Relax, unwind, and enjoy the magnificent views of the pristine sandy beach and the blue waters of the Gulf of Mexico from this unit in L ambiance. Turn around to the east and watch the boats on Sarasota Bay, and enjoy the lush fairways of the Longboat Key Golf Club. This well-designed unit

  Reid Murphy DEVELOPERS REALTY LBK, INC

  435 L Ambiance Dr Unit J704, Longboat Key, FL 34228
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  $14,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,268 Sq Ft
  • House for Rent

  531 Birdie Ln, Longboat Key, FL 34228

  Annual Rental – Stunning Waterfront Home in Country Club Shores on Longboat Key. Experience the best of waterfront living in this beautiful 4-bedroom, 3.5-bathroom home located in the sought-after Country Club Shores community on Longboat Key. This spacious and elegant residence offers breathtaking canal views, luxurious amenities, and direct boating access and boat lift. This exceptional home

  Karie Gorgone WAGNER REALTY

  531 Birdie Ln, Longboat Key, FL 34228
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  $305,000 Sold Mar 05, 2025

  569 Sutton Place, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,198 Sq Ft
  • Built 1972

  Last Sold Summary

  • 42% Below List Price
  • $255/SF
  • 165 Days On Market

  Current Estimated Value $301,875

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  569 Sutton Place, Longboat Key, FL 34228
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  Est $2,334,487 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft

  210 Sands Point Rd Unit 2603/04, Longboat Key, FL 34228

  210 Sands Point Rd Unit 2603/04, Longboat Key, FL 34228
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  /94

  $5,999,000

  • 4 Beds
  • 4.5 Baths
  • 3,921 Sq Ft

  2251 Gulf of Mexico Dr Unit 301, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Are you ready to discover your very own private Gulf Oasis? Step into a slice of paradise at your dream coastal retreat located in the esteemed Aria community on Longboat Key's coveted south end. This serene haven is not just a residence; it offers an exclusive lifestyle filled with tranquility and easy access to the finest dining, arts, and

  Rachel Woodruff HOUSE MATCH

  2251 Gulf of Mexico Dr Unit 301, Longboat Key, FL 34228
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  /60

  $4,000 per month

  • 1 Bed
  • 1 Bath
  • 811 Sq Ft
  • Condo for Rent

  3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  1-bed, 1-bath 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 community

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  $475,000 Sold Jul 25, 2025

  6750 Gulf of Mexico Dr Unit 153, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,441 Sq Ft
  • Built 1969

  Last Sold Summary

  • 32% Below List Price
  • $330/SF
  • 163 Days On Market

  Current Estimated Value $513,638

  Last Listing Agent Shayla Twit CORCORAN DWELLINGS REALTY

  6750 Gulf of Mexico Dr Unit 153, Longboat Key, FL 34228
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  /29

  Est $1,180,723 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,859 Sq Ft

  1445 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

  1445 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
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  $1,000,000

  • Land
  • 0.44 Acre
  • $2,272,727 per Acre

  6604 Gulf of Mexico Dr, Longboat Key, FL 34228

  Privacy is key for this sprawling, estate-size lot tucked down a quiet street on the north end of Longboat Key. While addressed on Gulf of Mexico Drive, the property is uniquely positioned off the main roadway, set back beyond three estate-sized parcels, offering a tranquil, quiet and peaceful canal-front setting. This rare location offers one of the largest single-family home lots available on

  Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  6604 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /53

  $4,200 per month

  • 2 Beds
  • 2 Baths
  • 1,640 Sq Ft
  • Condo for Rent

  840 Bayport Way Unit 840, Longboat Key, FL 34228

  This stunningly appointed ground floor 2-bedroom 2 bath condo with lots of open living space is the ideal place to spend your summer vacation. Relax on screened lanai and enjoy the gentle breezes of this tropical oasis. Situated between Sarasota Bay and the Gulf of Mexico and surrounded by lush landscaping, you will truly find the private patio a great place to spend your afternoons. The

  Shirley Cuddy REALTY SERVICES INC

  840 Bayport Way Unit 840, Longboat Key, FL 34228
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  $1,420,000 Sold Aug 13, 2025

  455 Longboat Club Rd Unit 407, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,410 Sq Ft
  • Built 1990

  Last Sold Summary

  • 25% Below List Price
  • $589/SF
  • 104 Days On Market

  Current Estimated Value $1,454,601

  Last Listing Agent Stacy Hanan MICHAEL SAUNDERS & COMPANY

  455 Longboat Club Rd Unit 407, Longboat Key, FL 34228
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  /42

  Est $844,490 Not Listed For Sale

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

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

  1085 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  /15

  $600,000

  • Land
  • 1 Acre
  • $600,000 per Acre

  2600 Harbourside Dr Unit B-13, Longboat Key, FL 34228

  An easy access slip with the views to along with the superb amenity package, Slip B-13 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 100 x 28, and a usable beam of 25 feet and a long and extra wide finger pier. This location provides close proximity to the hospitality room and Pool. The Longboat

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit B-13, Longboat Key, FL 34228
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  /45

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,192 Sq Ft
  • Condo for Rent

  1930 Harbourside Dr Unit 134, Longboat Key, FL 34228

  GORGEOUS BAY VIEWS plus Private Beach Club Access! You will love the views from this Bay Front, 2 bed, 2 bath third floor condo in the highly sought-after Bay Isles community. The spacious Kitchen had been updated along with the both baths, with Quartz counter-tops and new cabinetry, the Primary suite offers a King bed, views of the bay and the Primary bath has dual sinks, new vanity, new

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1930 Harbourside Dr Unit 134, Longboat Key, FL 34228
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  $750,000 Sold Jul 29, 2025

  765 Saint Judes Dr N, Longboat Key, FL 34228

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1963

  Last Sold Summary

  • 23% Below List Price
  • $395/SF
  • 136 Days On Market

  Current Estimated Value $770,719

  Last Listing Agent Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

  765 Saint Judes Dr N, Longboat Key, FL 34228
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  /18

  Est $345,117 Not Listed For Sale

  • Studio

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

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

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