Windermere, FL Homes

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  /30

  Est $507,557 Not Listed For Sale

  13347 Overstreet Rd, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft
  • Built 2013

  13347 Overstreet Rd, Windermere, FL 34786

  Last Sold Summary

  • 2% Above List Price
  • $243/SF
  • 46 Days On Market

  • Last Sold Price $500,000
  • Jun 10, 2024

  Last Listing Agent Eve Metlis WATSON REALTY CORP
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  /40

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,876 Sq Ft

  8648 Powder Ridge Trail, Windermere, FL 34786

  LOCATION, LOCATION, LOCATION! Welcome to this stunning bungalow-style single-family home located in the highly sought-after Windermere Trails community—where lifestyle, convenience, and charm meet at your front door.Built by Meritage Homes (consistently ranked among the best builders in Florida), this residence features the desirable Angelou floor plan offering 3 bedrooms, 2.5 bathrooms, a

  Renan Serretiello NOVA REAL ESTATE SERVICES INC

  8648 Powder Ridge Trail, Windermere, FL 34786
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  /2

  $600,000 Sold Jul 09, 2025

  5063 Carillon Ln, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,406 Sq Ft
  • Built 2004

  Last Sold Summary

  • $249/SF
  • 7 Days On Market

  Current Estimated Value $586,010

  Last Listing Agent Jared Dunn LIVE MVRK LLC

  5063 Carillon Ln, Windermere, FL 34786
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  /10

  Not Listed For Sale

  Lot 2 Down Park Ln, Windermere, FL 34786

  Lot 2 Down Park Ln, Windermere, FL 34786

  Last Sold Summary

  • 0 Days On Market

  • Last Sold Price $1,795,000
  • May 16, 2024

  Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC
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  $15,500,000

  • 10 Beds
  • 17 Baths
  • 13,425 Sq Ft

  12488 Park Ave, Windermere, FL 34786

  Commanding a rare 2.75-acre lakefront setting on the coveted Butler Chain of Lakes, this extraordinary Windermere estate is a true work of art. Recently completed after a meticulous, ground-up transformation, the residence showcases a level of craftsmanship, design integrity, and finish quality that is simply unrivaled in Central Florida. From the moment you arrive, the estate announces itself

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  12488 Park Ave, Windermere, FL 34786
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  /2

  $820,000 Sold Mar 06, 2026

  416 Magnolia St, Windermere, FL 34786

  • 2 Beds
  • 1.5 Baths
  • 2,115 Sq Ft
  • Built 1915

  Last Sold Summary

  • 7% Below List Price
  • $388/SF
  • 74 Days On Market

  Current Estimated Value $829,422

  Last Listing Agent Judy Black UPSIDE REAL ESTATE INC

  416 Magnolia St, Windermere, FL 34786
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  /18

  Est $767,842 Not Listed For Sale

  9207 Reflection Pointe Dr, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,010 Sq Ft
  • Built 2016

  9207 Reflection Pointe Dr, Windermere, FL 34786

  Last Sold Summary

  • 10% Below List Price
  • $282/SF
  • 46 Days On Market

  • Last Sold Price $850,000
  • Jun 14, 2024

  Last Listing Agent Jennifer Olmeda WRA BUSINESS & REAL ESTATE
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  /31

  $579,900

  • 4 Beds
  • 3 Baths
  • 2,229 Sq Ft

  6897 Northwich Dr, Windermere, FL 34786

  Welcome to the highly desirable Lakes of Windermere! Where comfort, convenience, and thoughtful updates come together in one of Central Florida’s most sought-after communities. This move-in ready 4-bedroom, 3-bathroom home offers a functional, open layout perfect for both everyday living and entertaining. Step inside to find upgraded flooring installed in 2023, creating a warm, modern feel

  Blake Blahut REALTY ONE GROUP INSPIRATION

  6897 Northwich Dr, Windermere, FL 34786
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  /2

  $1,650,000 Sold Sep 29, 2025

  4108 Downeast Ln, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,150 Sq Ft
  • Built 1979

  Last Sold Summary

  • 50% Below List Price
  • $524/SF
  • 208 Days On Market

  Current Estimated Value $1,610,875

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  4108 Downeast Ln, Windermere, FL 34786
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  /34

  Est $526,608 Not Listed For Sale

  6620 Bridgewater Village Rd, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,115 Sq Ft
  • Built 2013

  6620 Bridgewater Village Rd, Windermere, FL 34786

  Last Sold Summary

  • 3% Above List Price
  • $241/SF
  • 28 Days On Market

  • Last Sold Price $510,104
  • May 13, 2024

  Last Listing Agent Kristina Pena Mark Spain
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  /46

  $775,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,379 Sq Ft

  5018 River Gem Ave, Windermere, FL 34786

  Under contract-accepting backup offers. Welcome to 5018 River Gem Avenue, an exceptional one-story pool estate with serene pond views in the prestigious Summerport community of Windermere, perfectly positioned for luxury living, convenience, and resort-style enjoyment — only 20 minutes from the Disney Theme Parks, Disney Springs, premier shopping, dining, and major roadways. This 3-bedroom,

  Anastasia Fischer KELLER WILLIAMS SOUTH TAMPA

  5018 River Gem Ave, Windermere, FL 34786
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  /29

  $655,000 Sold Apr 16, 2026

  9426 Palm Tree Dr, Windermere, FL 34786

  • 4 Beds
  • 2 Baths
  • 2,063 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Above List Price
  • $317/SF
  • 54 Days On Market

  Current Estimated Value $645,437

  Last Listing Agent Richard Alpizar IVRE ORLANDO

  9426 Palm Tree Dr, Windermere, FL 34786
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  /2

  Est $729,813 Not Listed For Sale

  13124 Orange Isle Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,201 Sq Ft
  • Built 2022

  13124 Orange Isle Dr, Windermere, FL 34786

  Last Sold Summary

  • 4% Above List Price
  • $219/SF
  • 145 Days On Market

  • Last Sold Price $700,000
  • Sep 04, 2024

  Last Listing Agent Ken Pozek REAL BROKER, LLC
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  $2,299,000

  • 5 Beds
  • 4 Baths
  • 3,461 Sq Ft

  5067 Sawyer Cove Way, Windermere, FL 34786

  This custom estate in the exclusive, 20-home gated enclave of Sawyer Sound is an extraordinary property curated under the meticulous supervision of an accomplished interior designer. Located directly across from Windermere Prep, the residence pairs architectural grandeur— natural MARBLE FLOORS and soaring wood-beamed ceilings with the warmth of an impeccably appointed and maintained home. Every

  Denise Crabbe REVEL REALTY LLC

  5067 Sawyer Cove Way, Windermere, FL 34786
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  /2

  $1,030,000 Sold Apr 27, 2026

  6569 Crestmont Glen Ln, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,080 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Above List Price
  • $334/SF
  • 2 Days On Market

  Last Listing Agent Kim Gilbert THE AGENCY FL

  6569 Crestmont Glen Ln, Windermere, FL 34786
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  /16

  Est $328,690 Not Listed For Sale

  14214 Desert Haven St Unit 3604, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft
  • Built 2013

  14214 Desert Haven St Unit 3604, Windermere, FL 34786

  Last Sold Summary

  • 7% Below List Price
  • $235/SF
  • 10 Days On Market

  • Last Sold Price $355,000
  • Mar 28, 2024

  Last Listing Agent Phillip Kolbrich TOP FLORIDA HOMES
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  /31

  $800,000

  • 4 Beds
  • 3.5 Baths
  • 3,124 Sq Ft

  5413 Walsh Pond Ct, Windermere, FL 34786

  Discover the charm of this water front, 4 bedroom 3.5 bath home located in the desirable Summerport community. This unique property is nestled in the cul de sac for complete privacy. Enjoy scenic water views while relaxing poolside on the spacious screen enclosed lanai, which is also great for entertaining. The interior features granite countertops, stainless appliances, 42" cabinets, built in

  Brenda Jebailey HAVEN PROPERTY GROUP LLC

  5413 Walsh Pond Ct, Windermere, FL 34786
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  $1,350,000 Sold Oct 30, 2025

  11425 Claymont Cir, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,684 Sq Ft
  • Built 1999

  Last Sold Summary

  • 10% Below List Price
  • $366/SF
  • 99 Days On Market

  Current Estimated Value $1,372,643

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  11425 Claymont Cir, Windermere, FL 34786
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  /60

  Est $739,877 Not Listed For Sale

  13431 Swansea Ave, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,365 Sq Ft
  • Built 2005

  13431 Swansea Ave, Windermere, FL 34786

  Last Sold Summary

  • 1% Above List Price
  • $217/SF
  • 12 Days On Market

  • Last Sold Price $730,000
  • Apr 08, 2024

  Last Listing Agent Paul McGarigal RE/MAX SELECT GROUP
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  /22

  $315,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft

  11434 Jasper Kay Terrace Unit 1120, Windermere, FL 34786

  Beautifully maintained condo located in the highly desirable Lakeside Lakes of Windermere community. Situatedon the third floor with elevator access, this residence features a spacious split floor plan offering both privacy and functionality. The open concept living and dining area flows seamlessly to a private balcony perfect for enjoying your morning coffee or relaxing evenings.The

  alonso delgado REALTY ONE GROUP MVP

  11434 Jasper Kay Terrace Unit 1120, Windermere, FL 34786
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  /2

  $800,000 Sold Jan 09, 2026

  6905 Nobleton Dr, Windermere, FL 34786

  • 5 Beds
  • 5 Baths
  • 3,345 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Below List Price
  • $239/SF
  • 46 Days On Market

  Current Estimated Value $790,638

  Last Listing Agent Tony Tate LPT REALTY, LLC

  6905 Nobleton Dr, Windermere, FL 34786
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  Est $2,645,681 Not Listed For Sale

  2516 Windermere Reserve Ct, Windermere, FL 34786

  • 5 Beds
  • 5.5 Baths
  • 4,953 Sq Ft
  • Built 2023

  2516 Windermere Reserve Ct, Windermere, FL 34786

  Last Sold Summary

  • 7% Below List Price
  • $575/SF
  • 45 Days On Market

  • Last Sold Price $2,850,000
  • May 20, 2024

  Last Listing Agent Matt Tomaszewski CORCORAN PREMIER REALTY
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  /5

  $140,000

  • Land
  • 4 Acres
  • $35,000 per Acre

  0 Windermere Rd Unit MFRO6350486, Winter Garden, FL

  Looking for land with purpose and potential? This parcel (ID 312228000000032) in desirable Orange County offers a rare opportunity to create something extraordinary in a naturally rich environment. Set on four acres in the sought-after Windermere/Winter Garden area, this property provides the ideal canvas to design your dream home or investment project. Navigate to the lot — copy & paste into

  Jorge Martinez, Jr KELLER WILLIAMS CLASSIC

  0 Windermere Rd Unit MFRO6350486, Winter Garden, FL
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  /2

  $535,000 Sold Sep 04, 2025

  6830 Mapperton Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,230 Sq Ft
  • Built 2005

  Last Sold Summary

  • 1% Below List Price
  • $240/SF
  • 25 Days On Market

  Current Estimated Value $534,243

  Last Listing Agent Kristin Haughwout-Osorio PARKSIDE PROPERTIES, LLC

  6830 Mapperton Dr, Windermere, FL 34786
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  /40

  Est $773,569 Not Listed For Sale

  8705 Lookout Pointe Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,304 Sq Ft
  • Built 2015

  8705 Lookout Pointe Dr, Windermere, FL 34786

  Last Sold Summary

  • $235/SF
  • 12 Days On Market

  • Last Sold Price $777,000
  • Mar 15, 2024

  Last Listing Agent Christopher Soucy REALTY ONE GROUP MVP
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  $3,000,000 New Construction

  • 5 Beds
  • 5 Baths
  • 2,565 Sq Ft

  19 Main St, Windermere, FL 34786

  Under Construction. New Construction in Downtown Windermere Waterfront on the Butler Chain of Lakes!Experience modern lakefront living in the heart of the golf cart–friendly Town of Windermere. This brand-new construction home is currently under construction with an anticipated completion date of late Summer 2026. The residence will offer approximately 2,500 square feet of living space and

  Milena Fernandes GOLDEN GROUP REALTY LLC

  19 Main St, Windermere, FL 34786
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  /2

  $815,000 Sold Jul 21, 2025

  9601 Ambleside Dr, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 3,018 Sq Ft
  • Built 1975

  Last Sold Summary

  • 2% Above List Price
  • $270/SF
  • 5 Days On Market

  Current Estimated Value $838,402

  Last Listing Agent Matt Davies COLDWELL BANKER REALTY

  9601 Ambleside Dr, Windermere, FL 34786
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  /2

  Est $513,476 Not Listed For Sale

  7742 Brofield Ave, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,211 Sq Ft
  • Built 2011

  7742 Brofield Ave, Windermere, FL 34786

  Last Sold Summary

  Last Listing Agent Julien Silva JOHN SILVA REALTY & ASSOCIATES
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  $870,000

  • 5 Beds
  • 3.5 Baths
  • 3,724 Sq Ft

  8767 Iron Mountain Trail, Windermere, FL 34786

  The Melville floor plan features a functional and well-designed layout with formal living and dining areas, a spacious primary suite, an open-concept family room and a versatile flex space that can be used as a game room or adapted to suit a variety of lifestyle needs. Located in the desirable Windermere Trails community, the property offers convenient access to area lakes, daily essentials,

  Gilson Rodrigues KARDOSH REALTY

  8767 Iron Mountain Trail, Windermere, FL 34786
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  /2

  $1,025,000 Sold Feb 19, 2026

  1804 Maple Leaf Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,971 Sq Ft
  • Built 1989

  Last Sold Summary

  • $345/SF
  • 3 Days On Market

  Current Estimated Value $1,002,928

  Last Listing Agent Anna McIntyre LAKESIDE REALTY WINDERMERE INC

  1804 Maple Leaf Dr, Windermere, FL 34786
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  /20

  Est $447,605 Not Listed For Sale

  13731 Beringer St, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,912 Sq Ft
  • Built 2015

  13731 Beringer St, Windermere, FL 34786

  Last Sold Summary

  • 4% Below List Price
  • $245/SF
  • 11 Days On Market

  • Last Sold Price $468,000
  • Mar 21, 2024

  Last Listing Agent Sharon Knapp COMPASS FLORIDA LLC
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  $650,000 Pending

  • 5 Beds
  • 4 Baths
  • 3,015 Sq Ft

  6956 Trellis Vine Loop, Windermere, FL 34786

  This is a gorgeous two-story home with five bedrooms, four baths, and a two-car garage. This home offers an open floor plan with an expansive great room featuring an elegant display of windows to create a naturally luminous home, casual dining area, and kitchen. The casual dining area allows outdoor access to a lanai and the kitchen provides plenty of counter space as well as an oversized island

  Dan Li EAST PEARL REALTY

  6956 Trellis Vine Loop, Windermere, FL 34786
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  $3,000,000 Sold May 08, 2026

  6133 S Hampshire Ct, Windermere, FL 34786

  • 5 Beds
  • 7 Baths
  • 6,335 Sq Ft
  • Built 2000

  Last Sold Summary

  • 5% Below List Price
  • $474/SF
  • 2 Days On Market

  Current Estimated Value $2,750,726

  Last Listing Agent Angela Durruthy KEENE'S POINTE REALTY

  6133 S Hampshire Ct, Windermere, FL 34786
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  /2

  Est $587,016 Not Listed For Sale

  8329 Lookout Pointe Dr, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 2,633 Sq Ft
  • Built 2016

  8329 Lookout Pointe Dr, Windermere, FL 34786

  Last Sold Summary

  • 1% Above List Price
  • $220/SF
  • 56 Days On Market

  • Last Sold Price $580,000
  • Apr 11, 2025

  Last Listing Agent Ricardo Diaz WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC
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  $749,999

  • 4 Beds
  • 3.5 Baths
  • 3,360 Sq Ft

  13609 Ancilla Blvd, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Welcome to this stunning and spacious single-family home located in the heart of Windermere, offering breathtaking lake views from both the front and rear of the property. With 3,360 sqft heated living space, this beautifully maintained residence features a thoughtfully designed floor plan ideal for comfort and functionality. The first floor

  Fernanda Soares Santos de Oliveira WRA BUSINESS & REAL ESTATE

  13609 Ancilla Blvd, Windermere, FL 34786
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  $2,400,000 Sold Nov 24, 2025

  11106 Coniston Way, Windermere, FL 34786

  • 5 Beds
  • 7 Baths
  • 5,934 Sq Ft
  • Built 2008

  Last Sold Summary

  • 9% Below List Price
  • $404/SF
  • 153 Days On Market

  Current Estimated Value $2,366,063

  Last Listing Agent Toni Marie Cafferty COMPASS FLORIDA LLC

  11106 Coniston Way, Windermere, FL 34786
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  Est $672,265 Not Listed For Sale

  8355 Vivaro Isle Way, Windermere, FL 34786

  • 3 Beds
  • 3 Baths
  • 2,224 Sq Ft
  • Built 2019

  8355 Vivaro Isle Way, Windermere, FL 34786

  Last Sold Summary

  • $304/SF
  • 49 Days On Market

  • Last Sold Price $675,000
  • Jun 03, 2024

  Last Listing Agent Rossana Okamura ELEVATE REAL ESTATE BROKERS
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  /16

  $895,000

  • 4 Beds
  • 3 Baths
  • 2,224 Sq Ft

  13542 Gorgona Isle Dr, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Lake View Home with Private Pool & Fireworks Views – Minutes from Walt Disney World Imagine living in a home that perfectly combines comfort, elegance, and practicality in one of the most desirable areas of Windermere. This beautiful residence offers stunning lake views and magical nightly fireworks views from Walt Disney World, creating a truly

  Jennifer Olmeda WRA BUSINESS & REAL ESTATE

  13542 Gorgona Isle Dr, Windermere, FL 34786
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  /2

  $705,000 Sold Apr 15, 2026

  13649 Zori Ln, Windermere, FL 34786

  • 4 Beds
  • 4 Baths
  • 3,129 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $225/SF
  • 61 Days On Market

  Current Estimated Value $718,712

  Last Listing Agent Anamaria Marquez PREMIER SOTHEBYS INT'L REALTY

  13649 Zori Ln, Windermere, FL 34786
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  Not Listed For Sale

  6043 Savannah Oak Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,117 Sq Ft
  • Built 2019

  6043 Savannah Oak Aly, Windermere, FL 34786

  Last Sold Summary

  • $248/SF
  • 3 Days On Market

  • Last Sold Price $525,000
  • Mar 13, 2024

  Last Listing Agent Taraneh Ansari-Duran EXP REALTY LLC

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