Windermere, FL Homes

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  $855,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,712 Sq Ft

  Tidewater Plan at Palms at Windermere, Windermere, FL 34786

  The Tidewater floorplan offers a versatile and spacious two-story layout, featuring 4 bedrooms and 2.5 bathrooms. Spanning 2,712 sq. ft., this home includes a large two-car garage for ample storage and convenience. The first floor boasts an inviting great room connected to an open kitchen and dining area, perfect for entertaining. The owner’s suite provides a private retreat with a generous

  Dream Finders Homes Builder

  14207 Crest Palm Ave Unit 36489841, Windermere, FL 34786
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  $2,800 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,642 Sq Ft
  • Townhouse for Rent

  14392 Bridgewater Crossings Blvd, Windermere, FL 34786

  Location, Location, Location! Amazing 3 bedroom 2.5 bath, 2 story townhome located directly accross the street from the park in Summerport! Windermere!! Super clean, updated townhouse. Wood floors throughout. Stainless Steel appliances. Master is on the bottom floor. Second floor features a loft, as well as 2 bedrooms and a bathroom. 2 car rear entry garage. Sit back on your front porch with your

  Aleem Kanji CROWN REALTY COMPANY

  14392 Bridgewater Crossings Blvd, Windermere, FL 34786
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  /2

  $1,245,000

  Sold Jul 13, 2026

  2219 Ridgewind Way, Windermere, FL 34786

  • 6 Beds
  • 3.5 Baths
  • 3,364 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $370/SF
  • 25 Days On Market

  Current Estimated Value $1,278,242

  Last Listing Agent Hilary Hall COMPASS FLORIDA LLC

  2219 Ridgewind Way, Windermere, FL 34786
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  /2

  Est $523,955

  Not Listed For Sale

  6054 Roseate Spoonbill Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,984 Sq Ft
  • Built 2011

  6054 Roseate Spoonbill Dr, Windermere, FL 34786

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Aline Oliveira META ONE REALTY GROUP LLC
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  /67

  $1,849,000

  $251K PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 5,430 Sq Ft

  9057 Balmoral Mews Square, Windermere, FL 34786

  UST REPOSITIONED TO SELL – One of Windermere's Best Luxury Values! This is your opportunity to own a spectacular, fully renovated luxury estate in the prestigious gated community of Balmoral Estates at an exceptional new price. Offering an extraordinary combination of elegance, quality craftsmanship, and extensive recent improvements, this turnkey residence delivers outstanding value in today's

  Ryan Rogers REAL BROKER, LLC

  9057 Balmoral Mews Square, Windermere, FL 34786
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  /28

  $3,200 Per Month

  • 3 Beds
  • 2 Baths
  • 1,903 Sq Ft
  • Move-in Ready Home with 2 Car Garage in Desirable Summerport Community!

  5007 River Gem Ave, Windermere, FL 34786

  Welcome to the perfect rental home in the desirable community of Summerport! This home has it all as it sits on a corner lot, has both a front porch and screened-in back porch, fully fenced in lush backyard (lawn care included!) with paver patio and much more! Inside you're greeted by what could be a formal living room or dining room space and from there enter the fully loaded kitchen with LG

  5007 River Gem Ave, Windermere, FL 34786
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  /2

  $700,000

  Sold Feb 13, 2026

  9792 Wild Oak Dr, Windermere, FL 34786

  • 3 Beds
  • 3.5 Baths
  • 3,102 Sq Ft
  • Built 1982

  Last Sold Summary

  • 26% Below List Price
  • $226/SF
  • 106 Days On Market

  Current Estimated Value $745,381

  Last Listing Agent Suzette Berkhalter KELLER WILLIAMS ADVANTAGE III

  9792 Wild Oak Dr, Windermere, FL 34786
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  /2

  Est $1,215,613

  Not Listed For Sale

  6228 Lecco Way, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,755 Sq Ft
  • Built 2012

  6228 Lecco Way, Windermere, FL 34786

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
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  /93

  $6,700,000

  New Construction

  • 8 Beds
  • 10 Baths
  • 8,133 Sq Ft

  8342 Boyla Ct, Windermere, FL 34786

  Virtually Staged. Welcome to an extraordinary new construction waterfront estate built by Element Home Builders, located in the prestigious 24-hour guard gated community of Keene’s Pointe. Situated on a private cul-de-sac, this one of a kind residence rests on a spectacular 0.78 acre homesite with 518 feet of combined waterfront overlooking a serene pond and the beautiful waters of Lake Burden.

  Simon Simaan THE SIMON SIMAAN GROUP

  8342 Boyla Ct, Windermere, FL 34786
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  /33

  $2,995 Per Month

  • 4 Beds
  • 3 Baths
  • 2,190 Sq Ft
  • House for Rent

  8625 Greenbank Blvd, Windermere, FL 34786

  PRICE IMPROVEMENT FOR IMMEDIATE AVAILABILITY! Single family home with 4 bedrooms and 3 full bathrooms in desirable Lakes of Windermere Peachtree subdivision. This is quaint community convenient to Disney attractions for work or play and is gated and zoned for Windermere High School. Available just in time for the new school year. Located on a scenic pond w conservation area view, with no rear

  Charles Woolley BHHS FLORIDA REALTY

  8625 Greenbank Blvd, Windermere, FL 34786
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  /2

  $1,050,000

  Sold Oct 31, 2025

  65 Oakdale St, Windermere, FL 34786

  • 4 Beds
  • 2 Baths
  • 2,191 Sq Ft
  • Built 1959

  Last Sold Summary

  • 12% Below List Price
  • $479/SF
  • 34 Days On Market

  Current Estimated Value $1,076,384

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  65 Oakdale St, Windermere, FL 34786
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  /2

  Est $448,619

  Not Listed For Sale

  8749 Via Tavoleria Way, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 1,935 Sq Ft
  • Built 2014

  8749 Via Tavoleria Way, Windermere, FL 34786

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Denise Pellegrino REAL BROKER, LLC
• 

  $515,490

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,649 Sq Ft

  Cypress Plan at Lake Cawood Cove - Townhomes, Windermere, FL 34786

  Ashton Woods Builder

  5432 Winter Garden Vineland Rd Unit 37932786, Windermere, FL 34786
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  /12

  $3,800 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,078 Sq Ft
  • House for Rent

  12886 Westside Vlg Lp, Windermere, FL 34786

  Located in the highly desirable heart of Windermere, Westside Village is only minutes from access to multiple lakes, dining, shopping, and A-rated schools. Westside Village will also have fantastic community amenities including a resort-style pool, clubhouse, and playground. energy-efficient home feature open floor plan. Entertain in the combination dining/living room or move the party

  12886 Westside Vlg Lp, Windermere, FL 34786
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  /2

  $1,150,000

  Sold Jun 23, 2026

  8409 Vivaro Isle Way, Windermere, FL 34786

  • 6 Beds
  • 4.5 Baths
  • 4,176 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $275/SF
  • 30 Days On Market

  Current Estimated Value $1,164,510

  Last Listing Agent Katherine Figueroa Santiago WATSON REALTY CORP., REALTORS

  8409 Vivaro Isle Way, Windermere, FL 34786
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  /26

  Est $321,574

  Not Listed For Sale

  11434 Jasper Kay Terrace Unit 208, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 2007

  11434 Jasper Kay Terrace Unit 208, Windermere, FL 34786

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Jay Stewart SOUTHERN REALTY GROUP LLC
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  /30

  $629,900

  $19K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,147 Sq Ft

  13622 Darchance Rd, Windermere, FL 34786

  Welcome home to Berkshire Park. This 3bedroom, 2bath residence offers a balance of comfort and convenience in a quiet residential setting. Ideally located just minutes from world-class attractions including Walt Disney World, as well as shopping, dining, and major highways, this property places you at the center of Central Florida living.The community is surrounded by nearby schools,

  Javin Lopez AVANTI WAY REALTY LLC

  13622 Darchance Rd, Windermere, FL 34786
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  /37

  $2,475 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,429 Sq Ft
  • Townhouse for Rent

  Unlisted Address

  Welcome to this bright and spacious 3-bedroom, 2.5-bath corner-unit townhome in the Lakes of Windermere community, ideally located near Walt Disney World theme parks, shopping, restaurants, and State Road 535. The first-floor features tile throughout and an inviting open-concept layout connecting the kitchen, dining area, dinette, and living room. The kitchen features granite countertops,

  Aziz Elbrak LA ROSA REALTY LLC

  Unlisted Address
• 

  /2

  $2,175,000

  Sold Aug 20, 2026

  4224 Clarice Estates Dr, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 4,793 Sq Ft
  • Built 2018

  Last Sold Summary

  • 13% Below List Price
  • $454/SF
  • 407 Days On Market

  Current Estimated Value $2,158,455

  Last Listing Agent Paul Hickey FLORIDA GOLD REAL ESTATE LLC

  4224 Clarice Estates Dr, Windermere, FL 34786
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  /53

  Est $1,092,078

  Not Listed For Sale

  11708 Hampstead St, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,934 Sq Ft
  • Built 2015

  11708 Hampstead St, Windermere, FL 34786

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY
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  /98

  $1,750,000

  $49K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,297 Sq Ft

  2503 Butler Bay Dr N, Windermere, FL 34786

  Set behind the gates of Windermere Club, this lakefront residence delivers everyday comfort with a resort-style backdrop on beautiful Lake Crescent. Offering 4 bedrooms and 3 baths, the home is designed for easy living and effortless entertaining, with bright, open gathering spaces that keep the water views front and center. At the heart of the home, the kitchen pairs generous prep space with a

  Simon Simaan THE SIMON SIMAAN GROUP

  2503 Butler Bay Dr N, Windermere, FL 34786
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  /15

  $2,700 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,116 Sq Ft
  • House for Rent

  11686 Water Run Aly, Windermere, FL 34786

  Welcome to this beautiful and well-maintained 3-bedroom, 2.5-bathroom townhome, located in one of Windermere's most desirable communities. Offering the perfect blend of comfort, style, and convenience, this home is ideal for families and professionals alike. The spacious open floor plan features a bright living and dining area that flows seamlessly into a stunning gourmet kitchen with

  11686 Water Run Aly, Windermere, FL 34786
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  /2

  $2,200,000

  Sold Jul 31, 2026

  81 Oakdale St, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 4,284 Sq Ft
  • Built 2001

  Last Sold Summary

  • 12% Below List Price
  • $514/SF
  • 223 Days On Market

  Current Estimated Value $2,306,749

  Last Listing Agent David Warzycha COLDWELL BANKER REALTY

  81 Oakdale St, Windermere, FL 34786
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  /62

  Est $1,148,527

  Not Listed For Sale

  5522 Remsen Cay Ln, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,881 Sq Ft
  • Built 2016

  5522 Remsen Cay Ln, Windermere, FL 34786

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Alfredo Karam COLDWELL BANKER REALTY
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  $3,300,000

  • 4 Beds
  • 5.5 Baths
  • 3,966 Sq Ft

  515 W 2nd Ave, Windermere, FL 34786

  Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of frontage on the renowned Butler Chain of Lakes, This home offers a rare combination of luxury, privacy, space, and direct access to one of Central Florida's most coveted boating destinations.This beautifully appointed custom

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  515 W 2nd Ave, Windermere, FL 34786
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  /23

  $2,900 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,919 Sq Ft
  • Townhouse for Rent

  8642 Via Tavoleria, Windermere, FL 34786

  Welcome to this beautiful 3 bedroom/2.5 bathroom + office townhome in the Windermere community of Carrington. This charming townhome is spacious, inviting and perfectly maintained! The property is zoned for Windermere schools. When arriving through the front door, you will see that the downstairs includes all ceramic tile, a flex space (office), half bath, & an open family/kitchen area that opens

  Ken Pozek REAL BROKER, LLC

  8642 Via Tavoleria, Windermere, FL 34786
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  /2

  $480,000

  Sold Sep 26, 2025

  13715 Bressler Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,139 Sq Ft
  • Built 2019

  Last Sold Summary

  • 9% Below List Price
  • $224/SF
  • 215 Days On Market

  Current Estimated Value $489,904

  Last Listing Agent Irene Calderon PREFERRED REAL ESTATE BROKERS

  13715 Bressler Aly, Windermere, FL 34786
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  /2

  Est $2,560,094

  Not Listed For Sale

  9831 Grosvenor Pointe Cir, Windermere, FL 34786

  • 5 Beds
  • 5.5 Baths
  • 5,320 Sq Ft
  • Built 2012

  9831 Grosvenor Pointe Cir, Windermere, FL 34786

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Angela Durruthy KEENE'S POINTE REALTY
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  /70

  $1,895,000

  Open Sat 11AM - 1PM

  • 4 Beds
  • 4.5 Baths
  • 2,868 Sq Ft

  930 East Blvd, Windermere, FL 34786

  Set along the shores of Lake Bessie in the heart of Downtown Windermere, this contemporary lakefront residence pairs clean architectural design with effortless single-story living. Completed in 2024, the home offers 2,868 square feet with four bedrooms, each featuring a private en-suite bath, along with a dedicated home office and an open-concept layout designed around the water views. Inside,

  Steve Healy CORCORAN PREMIER REALTY

  930 East Blvd, Windermere, FL 34786
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  /10

  $1,960 Per Month

  • 2 Beds
  • 2 Baths
  • 1,161 Sq Ft
  • House for Rent

  8264 Maritime Flag St, Windermere, FL 34786

  CONDO - Newly renovated. 2 bed/2 bath, NEW Floors, New carpet in bedrooms, New paint throughout. Beautiful balcony, Elevator to 3rd floor. Nice Community amenities.

  8264 Maritime Flag St, Windermere, FL 34786
• 

  /2

  $930,000

  Sold Nov 10, 2025

  5141 Autumn Ridge Ln, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,390 Sq Ft
  • Built 1990

  Last Sold Summary

  • 2% Below List Price
  • $389/SF
  • 91 Days On Market

  Current Estimated Value $927,065

  Last Listing Agent Deb Schroeder INFINITY REALTY GROUP LLC

  5141 Autumn Ridge Ln, Windermere, FL 34786
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  /36

  Est $4,492,398

  Not Listed For Sale

  12300 Montalcino Cir, Windermere, FL 34786

  • 5 Beds
  • 6.5 Baths
  • 7,649 Sq Ft
  • Built 2023

  12300 Montalcino Cir, Windermere, FL 34786

  Last Sold Summary

  • 73 Days On Market

  Last Listing Agent David Alvarez Aserraf ROI AVE LLC
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  /20

  $1,600,000

  $50K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,627 Sq Ft

  212 W 1st Ave, Windermere, FL 34786

  Virtually Staged. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity in the Town of Windermere.Boasting approximately 65 feet of private frontage and a dedicated boat dock, the property captures sweeping views across Wauseon Bay. The current home is in good condition and ready to move in. The interior showcases a refined yet

  Eric Powell HOME WISE REALTY GROUP, INC.

  212 W 1st Ave, Windermere, FL 34786
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  /45

  $3,250 Per Month

  • 3 Beds
  • 2 Baths
  • 1,921 Sq Ft
  • House for Rent

  905 Main St, Windermere, FL 34786

  Ready for Immediate Occupancy! Discover the opportunity to rent a beautifully updated home in the heart of Downtown Windermere, where charming small town living meets modern comfort. From the moment you arrive, you will appreciate the home’s contemporary curb appeal, featuring oversized windows, a private balcony, paver walkway, and welcoming covered front porch. Inside, the spacious living room

  Simon Simaan THE SIMON SIMAAN GROUP

  905 Main St, Windermere, FL 34786
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  /2

  $390,000

  Sold Apr 28, 2026

  8226 Serenity Spring Dr Unit 2402, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,028 Sq Ft
  • Built 2013

  Last Sold Summary

  • 2% Below List Price
  • $192/SF
  • 28 Days On Market

  Current Estimated Value $390,074

  Last Listing Agent Garrett Turner EXP REALTY LLC

  8226 Serenity Spring Dr Unit 2402, Windermere, FL 34786
• 

  

  /31

  Est $350,765

  Not Listed For Sale

  8167 Enchantment Dr Unit 1501, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,786 Sq Ft
  • Built 2010

  8167 Enchantment Dr Unit 1501, Windermere, FL 34786

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Melanie Gocinski REAL BROKER, LLC
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  /18

  $648,683

  New Construction Pending

  • 3 Beds
  • 2.5 Baths
  • 1,714 Sq Ft

  13407 Lemon Orchard Bend, Windermere, FL 34786

  Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a private paver courtyard and two-car garage, perfectly located in the heart of Windermere. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. Design upgrades include gourmet kitchen with 42" cabinets, quartz countertops, tiled

  Reed Williams ASHTON WOODS FLORIDA REALTY LLC

  13407 Lemon Orchard Bend, Windermere, FL 34786
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  /57

  $2,999 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  14252 Confetti Dr, Windermere, FL 34786

  WATER & ELECTRIC INCLUDED!! MOVE IN END OF AUGUST!! Welcome home! 3X2.5 bath 2 story main house 2000 sq ft!! Spacious living area! Perfect for entertaining as it opens to the amazing kitchen that featuring elegant 42" cabinets with beautiful Corian countertops. Elegant French doors in the living room lead to the beautiful view of the courtyard in back. All bedrooms are on the 2nd floor!

  14252 Confetti Dr, Windermere, FL 34786
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  /2

  $2,700,000

  Sold Feb 09, 2026

  9151 Tibet Pointe Cir, Windermere, FL 34786

  • Land
  • 2.21 Acres
  • $1,221,719 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 341 Days On Market

  Current Estimated Value $2,714,197

  Last Listing Agent Janet Allen PREMIER SOTHEBYS INT'L REALTY

  9151 Tibet Pointe Cir, Windermere, FL 34786
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  /43

  Est $2,926,415

  Not Listed For Sale

  5054 Sawyer Cove Way, Windermere, FL 34786

  • 5 Beds
  • 6.5 Baths
  • 5,353 Sq Ft
  • Built 2020

  5054 Sawyer Cove Way, Windermere, FL 34786

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Julie Davis, LLC COLDWELL BANKER REALTY

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