Siesta Key, FL Homes

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  /63

  $4,900,000

  • 7 Beds
  • 7 Baths
  • 3,742 Sq Ft

  5219 Calle Menorca, Sarasota, FL 34242

  Discover the ultimate in Florida coastal living at this stunning seven-bedroom, seven-bathroom luxury retreat, located just moments from the pristine sands of Siesta Key Beach. Perfectly designed for relaxation, entertainment, and upscale comfort, this expansive home is an exceptional blend of style, space, and convenience.Step inside and be greeted by an open, airy floor plan infused with

  Jay Travis RE/MAX ALLIANCE GROUP

  5219 Calle Menorca, Sarasota, FL 34242
• 

  

  /2

  $965,000 Sold Apr 04, 2025

  • 1,737 Sq Ft
  • $556/SF
  • 165 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1982

  1271 Dockside Place Unit 215, Sarasota, FL 34242

  Experience coastal living in this HIGH and DRY waterfront 3-bedroom, 2-bathroom condo on the sought-after Siesta Key. Perfectly positioned just steps from the renowned Siesta Key Beach, this second-floor gem offers unparalleled access to sun and sand, while a private boat slip and lift awaits your boating adventures.This turnkey-furnished condo is meticulously designed for both relaxation

  Debra Forkan COLDWELL BANKER REALTY

  1271 Dockside Place Unit 215, Sarasota, FL 34242
• 

  

  

  /64

  Est $1,230,890 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,206 Sq Ft

  5125 Oakmont Place, Sarasota, FL 34242

  5125 Oakmont Place, Sarasota, FL 34242
• 

  

  

  /46

  $2,450,000

  • 1,920 Sq Ft

  308 Canal Rd, Sarasota, FL 34242

  Welcome to Salty Summer & Summer Salt, a fantastic duplex with a shared pool perfectly located minutes from the turquoise waters and powder-soft sands of the Gulf and steps from Siesta Village, which offers a variety of shops and restaurants. With two bedrooms and two bathrooms in each unit, this home is perfect for your beach getaway, so pack your bags and enjoy a dream island vacation on Siesta

  Constantine Stratos COLDWELL BANKER REALTY

  308 Canal Rd, Sarasota, FL 34242
• 

  

  /2

  $990,000 Sold Apr 03, 2025

  • 1,953 Sq Ft
  • $507/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  5159 Oakmont Place, Sarasota, FL 34242

  A HURRICANE SURVIVOR SUPERSTAR--NO DAMAGE HERE!! This CHARMING COASTAL HOME invites you to live the ultimate seaside dream! This home has been IMPECCABLY MAINTAINED and is in a GREAT LOCATION! Only 1.4 miles to the ICONIC #1 rated SIESTA KEY BEACH and 2.4 miles to SIESTA KEY VILLAGE. Surrounded by vibrant, beachy charm, this home offers the perfect escape- where relaxation meets adventure.

  Jenni Burnette COLDWELL BANKER REALTY

  5159 Oakmont Place, Sarasota, FL 34242
• 

  

  /41

  Est $2,207,727 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,753 Sq Ft

  5223 Calle Menorca, Sarasota, FL 34242

  5223 Calle Menorca, Sarasota, FL 34242
• 

  

  /28

  $398,888

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft

  6006 Midnight Pass Rd Unit 48, Sarasota, FL 34242

  Beachside Living at Its Best - Casa Mar on Siesta KeyWelcome to Casa Mar, a sought-after beachfront community offering the perfect combination of island charm and modern convenience. This 1-bedroom, 1-bathroom unfurnished unit is a rare opportunity to create your very own coastal getaway or capitalize on a high-demand vacation rental investment. Just steps from one of the widest and most

  Deniz Topkara KELLER WILLIAMS ON THE WATER S

  6006 Midnight Pass Rd Unit 48, Sarasota, FL 34242
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  /2

  $2,200,000 Sold Apr 02, 2025

  • 2,635 Sq Ft
  • $835/SF
  • 81 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2003

  447 Canal Rd Unit 447, Sarasota, FL 34242

  Welcome to Grand Siesta! Rarely available Opportunity! Where else on Siesta Key can you find this unique location, offering Siesta Beach Access a block away, the Siesta Village two blocks away, directly on the Grand Canal with a boat lift, while all within the weekly rental zone. Paradise awaits at this fabulous, 3 bedroom/3.5 bath luxury townhouse. This amazing, spacious, luxury townhouse draws

  Joseph Kesslak COLDWELL BANKER REALTY

  447 Canal Rd Unit 447, Sarasota, FL 34242
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  /36

  Est $1,210,125 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,835 Sq Ft

  1345 Siesta Bayside Dr Unit 1345F, Sarasota, FL 34242

  1345 Siesta Bayside Dr Unit 1345F, Sarasota, FL 34242
• 

  

  /53

  $995,500

  • 2 Beds
  • 1.5 Baths
  • 725 Sq Ft

  643 Calle Del Otono, Sarasota, FL 34242

  Beachside Investment & Retreat — Just 100 Yards from Siesta Key Beach!Price Reduced to $995,500 (Previously $1,100,000)Discover the ultimate opportunity to own a luxury beach home and an income-producing investment in one! Perfectly located just 100 yards from the world-renowned white sands of Siesta Key Beach, this beautifully renovated 2-bedroom coastal getaway seamlessly blends

  Dennis Perkins CORAL BAY REALTY LLC

  643 Calle Del Otono, Sarasota, FL 34242
• 

  /2

  $915,000 Sold Apr 01, 2025

  • 1,915 Sq Ft
  • $478/SF
  • 52 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1997

  1260 Dolphin Bay Way Unit 303, Sarasota, FL 34242

  Best Opportunity on Siesta Key– Motivated Sellers! This is your chance to own a stunning waterfront residence in highly sought-after Dolphin Bay on Siesta Key – at an incredible price! This gated, pet-friendly community offers resort-style living with only 50 exclusive residences. Enjoy top-tier amenities, including a swimming pool and spa, har-tru tennis courts, fitness center, clubhouse with

  Maureen Doherty MICHAEL SAUNDERS & COMPANY

  1260 Dolphin Bay Way Unit 303, Sarasota, FL 34242
• 

  

  /59

  Est $689,295 Not Listed For Sale

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

  5860 Midnight Pass Rd Unit 19, Sarasota, FL 34242

  5860 Midnight Pass Rd Unit 19, Sarasota, FL 34242
• 

  

  /25

  $1,550,000

  • 3 Beds
  • 2 Baths
  • 2,037 Sq Ft

  5880 Midnight Pass Rd Unit 207, Sarasota, FL 34242

  See this beautifully decorated three-bedroom home, at the top rated condominium, Casarina. Escape winter's gloom and embrace the sun-kissed shores of Siesta Key, America's number one beach. Go from your door onto the sugar white sands for sunset visits, invigorating swims, or lively tennis and pickleball matches. This rare three-bedroom condominium, ideal for year-round living or as a seasonal

  Maureen Morris PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5880 Midnight Pass Rd Unit 207, Sarasota, FL 34242
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  /2

  $3,270,000 Sold Apr 01, 2025

  • 2,627 Sq Ft
  • $1,245/SF
  • 75 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1966

  77 Sandy Hook Rd N, Sarasota, FL 34242

  Stunning Gulf of Mexico views from the living room, dining room, kitchen, primary bedroom and office make this a magical place. The multi-level decks and outdoor seating areas are an incredible place to view the gulf and watch sunsets and dolphins. Located in the Sandy Hook community with a private shared beach, the home is walking distance to the Siesta Key Village with its fantastic

  Daniel Shattuck FLORIDA REALTY INVESTMENTS

  77 Sandy Hook Rd N, Sarasota, FL 34242
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  /80

  Est $1,046,648 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,433 Sq Ft

  5790 Midnight Pass Rd Unit 205, Sarasota, FL 34242

  5790 Midnight Pass Rd Unit 205, Sarasota, FL 34242
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  /63

  $1,125,000

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft

  19 Whispering Sands Dr Unit 805, Sarasota, FL 34242

  Welcome to Unit 805 at Whispering Sands – Your Gulf-Front Oasis AwaitsStep into paradise at Unit 805 in the North Tower of Whispering Sands, where the bright sands and shimmering aqua waters of the Gulf of Mexico are just outside your door. This beautifully turnkey-furnished 2-bedroom, 2-bath condo offers breathtaking, panoramic views from its 8th-floor balcony—balcony completion expected

  David Stasney COLDWELL BANKER REALTY

  19 Whispering Sands Dr Unit 805, Sarasota, FL 34242
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  /2

  $792,000 Sold Apr 01, 2025

  • 1,211 Sq Ft
  • $654/SF
  • 80 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1976

  5855 Midnight Pass Rd Unit 722, Sarasota, FL 34242

  Experience resort-style living on Siesta Key in this stunning, turnkey-furnished, West-facing penthouse condo. Offering approximately 1,211 sq. ft. of open living space, this top-floor residence boasts soaring ceilings that flood the home with natural light, creating expansive views and a bright, airy coastal ambiance. The generously sized bedrooms feature walk-in closets, additional storage, and

  Kelli Eggen COLDWELL BANKER REALTY

  5855 Midnight Pass Rd Unit 722, Sarasota, FL 34242
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  /7

  Est $1,057,387 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,989 Sq Ft

  4929 Peaceable Way, Sarasota, FL 34242

  4929 Peaceable Way, Sarasota, FL 34242
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  /53

  $780,000

  • 2 Beds
  • 2 Baths
  • 1,460 Sq Ft

  1255 E Peppertree Dr Unit 507, Sarasota, FL 34242

  Magnificent water views! It is like watching a boat parade every day! Welcome to Peppertree Bay, a sought-after beach to bay community on Siesta Key. This pristine 2-bedroom 2-bath condo has been beautifully updated to appeal to the modern discerning buyer, with clean contemporary finishes showcasing its coastal charm. Step inside to find a spacious open floor plan incorporating gorgeous

  Ethel Lovelace MICHAEL SAUNDERS & COMPANY

  1255 E Peppertree Dr Unit 507, Sarasota, FL 34242
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  /2

  $375,000 Sold Apr 01, 2025

  • 780 Sq Ft
  • $481/SF
  • 118 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 1968

  1215 S Portofino Dr Unit 404, Sarasota, FL 34242

  Unbelievable $50K price reduction on this move-in ready Canal front condo. Escape the winter chill and embrace endless summer in this meticulously remodeled 1 bedroom, 2 bathroom Siesta Key condo at Siesta Harbor, priced at only $450,000 with a peek-a-boo ocean view from the 4th floor. The owners have invested over $100K in premium upgrades, including a glassed-in lanai with hurricane impact

  Miao Whiteside BERKSHIRE HATHAWAY HOMESERVICE

  1215 S Portofino Dr Unit 404, Sarasota, FL 34242
• 

  

  /69

  Est $1,298,396 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,295 Sq Ft

  5310 Hidden Harbor Rd, Sarasota, FL 34242

  5310 Hidden Harbor Rd, Sarasota, FL 34242
• 

  

  /52

  $495,000

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  5681 Midnight Pass Rd Unit 104, Sarasota, FL 34242

  Welcome to your relaxation destination- White Sands Village- located across from Tripadvisor's #1 RATED BEACH IN THE U.S. AND #4 IN THE WORLD- SIESTA BEACH! Let the cool quartz white powder sand and clear water soothe your soul. This comfortable 1,012 sqft, TURN KEY FURNISHED, 2 bedroom/ 2 bath condo has recently been refreshed by a professional designer. The UPDATED, opened up kitchen features

  Rachelle Tirey PREFERRED SHORE LLC

  5681 Midnight Pass Rd Unit 104, Sarasota, FL 34242
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  /2

  $890,000 Sold Apr 01, 2025

  • 1,361 Sq Ft
  • $654/SF
  • 124 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1981

  5760 Midnight Pass Rd Unit 702, Sarasota, FL 34242

  Rare opportunity to own a turnkey-furnished two-bedroom, two-bath beach oasis on the seventh floor in the highly sought-after D Building with beach access just steps away. Located in the heart of Siesta Key at the exclusive upscale Gulf & Bay Club offering an incredibly beautiful lifestyle right on the Gulf of Mexico. Enjoy breathtaking sunsets from your personal enclosed veranda. With

  Robert Sherman PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5760 Midnight Pass Rd Unit 702, Sarasota, FL 34242
• 

  

  /45

  Est $1,471,009 Not Listed For Sale

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

  395 Avenida Milano, Sarasota, FL 34242

  395 Avenida Milano, Sarasota, FL 34242
• 

  

  /26

  $849,000

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

  5855 Midnight Pass Rd Unit 621, Sarasota, FL 34242

  Motivated Seller - Breathtaking Gulf Views and Spectacular Sunsets Await!Perched on the 6th floor, this beautifully updated condo offers sweeping views of the Gulf and stunning nightly sunsets. The building has recently completed a $12 million structural renovation, featuring all-new hurricane-impact windows and sliding glass doors, along with fresh exterior stucco and paint—making it one of

  Heidi Scholten MEDWAY REALTY

  5855 Midnight Pass Rd Unit 621, Sarasota, FL 34242
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  /2

  $1,650,000 Sold Apr 01, 2025

  • 3,924 Sq Ft
  • $420/SF
  • 353 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 2000

  5598 Siesta Estates Ct, Sarasota, FL 34242

  This luxurious John Cannon built home is in a small gated community that is just a short walk to the world famous Siesta Key beach. Enjoy privacy and security at the end of a Cul-de-sac in this well maintained 6 bedroom, 5 1⁄2 bath home, and is being offered Turn-Key furnished. It's the perfect home for Vacationing with Family and Friends. Features include a beautiful Kitchen with granite counter

  Darren Duffy RE/MAX PALM REALTY

  5598 Siesta Estates Ct, Sarasota, FL 34242
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  /72

  Est $1,349,528 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,968 Sq Ft

  4926 Commonwealth Dr, Sarasota, FL 34242

  4926 Commonwealth Dr, Sarasota, FL 34242
• 

  

  /47

  $495,000

  • 2 Beds
  • 2 Baths
  • 929 Sq Ft

  1350 N Portofino Dr Unit 208, Sarasota, FL 34242

  Turnkey furnished 2-bedroom, 2-bath condo in the desirable 55+ community of Siesta Harbor on Siesta Key. This light-filled unit features a spacious primary suite with walk-in closet and balcony access. Enjoy canal views and partial views of Little Sarasota Bay from the enclosed lanai. Boaters will appreciate direct access to the Intracoastal with no bridges and the option to lease dock space for

  Maurice Menager MICHAEL SAUNDERS & COMPANY

  1350 N Portofino Dr Unit 208, Sarasota, FL 34242
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  /2

  $950,000 Sold Mar 31, 2025

  • 1,510 Sq Ft
  • $629/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1957

  431 Avenida de Mayo, Sarasota, FL 34242

  Siesta Key waterfront home, prime location and endless potential! Location, location, location. This exceptional Siesta Key beach home is just near world-famous Siesta Beach and vibrant Siesta Village, offering easy access to top-rated dining, shopping and entertainment. On a large, beautifully landscaped lot along the coveted Grand Canal, this property is a rare find with direct waterfront

  Mike Warm PREMIER SOTHEBY'S INTERNATIONAL REALTY

  431 Avenida de Mayo, Sarasota, FL 34242
• 

  /2

  Est $694,278 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,460 Sq Ft

  1200 E Peppertree Ln Unit 407, Sarasota, FL 34242

  1200 E Peppertree Ln Unit 407, Sarasota, FL 34242
• 

  

  /55

  $690,000

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  1159 Lake House Cir Unit C120, Sarasota, FL 34242

  Enjoy this ultimate beach getaway and investment opportunity! This updated 2-bedroom 2 bath townhome is located directly across from Siesta Key beach and offers a generous split-bedroom and bi-level layout. Featuring high ceilings, a large light-filled eat-in kitchen, inside laundry, separate dining and living room areas and a spacious balcony overlooking the serene lake. The master bedroom suite

  Dan Miller PREFERRED SHORE LLC

  1159 Lake House Cir Unit C120, Sarasota, FL 34242
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  /2

  $660,000 Sold Mar 28, 2025

  • 1,130 Sq Ft
  • $584/SF
  • 108 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1988

  1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242

  Deeded Beach access on Siesta Key! This immaculate corner unit condo is the perfect blend of serenity and modern living, boasting breathtaking views and top-notch amenities. Tucked away amidst lush tropical landscaping, this single-level ground floor condo offers a peaceful pond and fountain view right from your private lanai. It’s an ideal retreat for those seeking tranquility and a connection

  Kaitlin Kuhn MICHAEL SAUNDERS & COMPANY

  1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242
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  /10

  Est $846,351 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft

  1001 Beach Rd Unit A504, Sarasota, FL 34242

  1001 Beach Rd Unit A504, Sarasota, FL 34242
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  /63

  $2,150,000

  • Land
  • 0.58 Acre
  • $3,706,897 per Acre

  0 Ocean Blvd, Sarasota, FL 34242

  Rare Canal-Front Opportunity on Siesta Key – Last Available Raw Land Parcels. Don’t miss the final two canal-front parcels on Siesta Key, exclusively offered as a package to one buyer. These gorgeous lots can be kept as individual 1⁄4+ acre parcels or combined into a single 1⁄2-acre estate. Build your dream home on the serene, tree-lined canal-front lot and develop the front lot as a

  Lisa Shepard BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  0 Ocean Blvd, Sarasota, FL 34242
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  /2

  $1,800,000 Sold Mar 28, 2025

  • 3,653 Sq Ft
  • $493/SF
  • 212 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1966

  5531 Contento Dr, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. This property is priced to sell! Situated on one of the most beautiful boat basins on the island providing exceptional open serene views. Ideally poised on a generous 16,000+ sq ft lot close to the world-renowned Siesta Key Beach, this home offers easy access to powdery white sands and breathtaking sunsets. Enjoy the convenience of Siesta Village

  Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  5531 Contento Dr, Sarasota, FL 34242
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  /44

  Est $1,006,939 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,435 Sq Ft

  4822 Ocean Blvd Unit 5B, Sarasota, FL 34242

  4822 Ocean Blvd Unit 5B, Sarasota, FL 34242
• 

  

  /36

  $1,999,900

  • 3 Beds
  • 3 Baths
  • 3,324 Sq Ft

  681 Avenida de Mayo, Sarasota, FL 34242

  Park your Boat behind your home .... Welcome to this boaters paradise! This recently renovated 3-bedroom, 3-bathroom home nestled in the heart of Siesta Key. With 3,324 square feet of well designed living space, this contemporary home offers both luxury and comfort in one of Florida's most coveted locations.Step inside to find over-sized rooms that can be utilized for entertaining or simply

  Colette Jay HORIZON REALTY INTERNATIONAL

  681 Avenida de Mayo, Sarasota, FL 34242
• 

  /2

  $3,995,000 Sold Mar 27, 2025

  • 4,974 Sq Ft
  • $803/SF

  • 4 Beds
  • 5.5 Baths
  • Built 1981

  5306 Siesta Cove Dr, Sarasota, FL 34242

  This elegant 5,000-square-foot waterfront home offers an exceptional blend of timeless style and modern functionality, with 4 en-suite bedrooms, 6 bathrooms, 2 home offices, 2 laundry rooms, and unmatched storage. A conforming home elevated to 10’ and recently remodeled (2023) with no detail overlooked, it exudes sophistication from the authentic copper lanterns outside to the finest-quality

  Nick Gard COLDWELL BANKER REALTY

  5306 Siesta Cove Dr, Sarasota, FL 34242
• 

  

  /46

  Est $849,647 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,253 Sq Ft

  6300 Midnight Pass Rd Unit 4, Sarasota, FL 34242

  6300 Midnight Pass Rd Unit 4, Sarasota, FL 34242
• 

  

  /45

  $795,000

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

  6204 Midnight Pass Rd Unit 201, Sarasota, FL 34242

  Virtually staged to showcase the full potential of this beautiful Siesta Key condo! Just steps from the powdery sands of Siesta Key Beach, this turnkey 2-bedroom, 2-bath unit offers the perfect blend of comfort, style, and value. The unit features vaulted ceilings that create a spacious feel, along with a covered parking space and private storage area. New hurricane-impact windows and doors have

  Nili Blaha VUE REALTY, LLC

  6204 Midnight Pass Rd Unit 201, Sarasota, FL 34242

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