Recently Sold Windermere, FL Homes

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  $508,000

  Sold Jan 30, 2026

  12860 Penshurst Ln, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,460 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Above List Price
  • $207/SF
  • 3 Days On Market

  Current Estimated Value $501,206

  Last Listing Agent Jeffrey Funk EXP REALTY LLC

  12860 Penshurst Ln, Windermere, FL 34786
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  $1,200,000

  Sold Jul 01, 2026

  2127 Lilypad Ln, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,349 Sq Ft
  • Built 1989

  Last Sold Summary

  • 4% Below List Price
  • $358/SF
  • 13 Days On Market

  Current Estimated Value $1,215,087

  Last Listing Agent Angela Jaspon UNITED REAL ESTATE PREFERRED

  2127 Lilypad Ln, Windermere, FL 34786
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  $9,000,000

  Sold Oct 06, 2025

  9832 Laurel Valley Dr, Windermere, FL 34786

  • 6 Beds
  • 10 Baths
  • 11,100 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $811/SF
  • 0 Days On Market

  Current Estimated Value $8,635,966

  Last Listing Agent Dianna Desboyaux DOUGLAS ELLIMAN

  9832 Laurel Valley Dr, Windermere, FL 34786
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  $390,000

  Sold Apr 30, 2026

  12879 Emersondale Ave, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,565 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $249/SF
  • 37 Days On Market

  Current Estimated Value $321,941

  Last Listing Agent Kyle Li UNIONE REALTY INC

  12879 Emersondale Ave, Windermere, FL 34786
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  $2,350,000

  Sold Oct 21, 2025

  10121 Lone Tree Ln, Orlando, FL 32836

  • 3 Beds
  • 2 Baths
  • 2,348 Sq Ft
  • Built 1968

  Last Sold Summary

  • 6% Below List Price
  • $1,001/SF
  • 0 Days On Market

  Current Estimated Value $2,359,368

  Last Listing Agent Ursula Garcia Moraes PRISTINE INTERNATIONAL REALTY LLC

  10121 Lone Tree Ln, Orlando, FL 32836
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  /2

  $1,700,000

  Sold Oct 10, 2025

  830 Oakdale St, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 3,670 Sq Ft
  • Built 2019

  Last Sold Summary

  • 13% Below List Price
  • $463/SF
  • 320 Days On Market

  Current Estimated Value $1,734,397

  Last Listing Agent Jay Martin CORCORAN PREMIER REALTY

  830 Oakdale St, Windermere, FL 34786
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  $716,000

  Sold Mar 31, 2026

  13912 Darchance Rd, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,699 Sq Ft
  • Built 2008

  Last Sold Summary

  • 1% Above List Price
  • $265/SF
  • 5 Days On Market

  Current Estimated Value $708,025

  Last Listing Agent Hojin Chang RE/MAX PRIME PROPERTIES

  13912 Darchance Rd, Windermere, FL 34786
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  /2

  $1,710,000

  Sold Jan 16, 2026

  7417 Lake Albert Dr, Windermere, FL 34786

  • 6 Beds
  • 6.5 Baths
  • 5,006 Sq Ft
  • Built 2014

  Last Sold Summary

  • 1% Above List Price
  • $342/SF
  • 80 Days On Market

  Current Estimated Value $1,707,289

  Last Listing Agent Dan Palmer TEAM DONOVAN

  7417 Lake Albert Dr, Windermere, FL 34786
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  /2

  $1,650,000

  Sold Aug 21, 2026

  6110 Keenes Pointe Dr, Windermere, FL 34786

  • 4 Beds
  • 4 Baths
  • 3,196 Sq Ft
  • Built 2002

  Last Sold Summary

  • 13% Below List Price
  • $516/SF
  • 126 Days On Market

  Current Estimated Value $1,773,354

  Last Listing Agent Donna Calhoun KELLER WILLIAMS CLASSIC

  6110 Keenes Pointe Dr, Windermere, FL 34786
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  /2

  $799,000

  Sold May 21, 2026

  5427 Nagami Dr, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 3,493 Sq Ft
  • Built 2005

  Last Sold Summary

  • $229/SF
  • 6 Days On Market

  Current Estimated Value $797,440

  Last Listing Agent Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  5427 Nagami Dr, Windermere, FL 34786
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  $710,000

  Sold Nov 25, 2025

  9631 Hollyglen Place, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,854 Sq Ft
  • Built 1979

  Last Sold Summary

  • 5% Below List Price
  • $249/SF
  • 14 Days On Market

  Current Estimated Value $738,716

  Last Listing Agent Hilary Hall COMPASS FLORIDA LLC

  9631 Hollyglen Place, Windermere, FL 34786
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  $573,350

  Sold Apr 17, 2026

  9056 Woodbreeze Blvd, Windermere, FL 34786

  • 4 Beds
  • 2 Baths
  • 2,063 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Above List Price
  • $278/SF
  • 2 Days On Market

  Current Estimated Value $573,035

  Last Listing Agent Ryan Solberg MAXLIFE REALTY LLC

  9056 Woodbreeze Blvd, Windermere, FL 34786
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  /2

  $435,000

  Sold Jan 01, 2026

  13775 Bressler Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,001 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $217/SF
  • 84 Days On Market

  Current Estimated Value $449,718

  Last Listing Agent Sonia Frederick BAHIA INTERNATIONAL REALTY

  13775 Bressler Aly, Windermere, FL 34786
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  $900,000

  Sold Jun 02, 2026

  4 Chase Rd, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,386 Sq Ft
  • Built 1971

  Last Sold Summary

  • $377/SF
  • 62 Days On Market

  Current Estimated Value $884,801

  Last Listing Agent Matthew Hughes REAL BROKER, LLC

  4 Chase Rd, Windermere, FL 34786
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  $3,700,000

  Sold Jul 06, 2026

  12132 Montalcino Cir, Windermere, FL 34786

  • 6 Beds
  • 7 Baths
  • 5,709 Sq Ft
  • Built 2016

  Last Sold Summary

  • 12% Below List Price
  • $648/SF
  • 205 Days On Market

  Current Estimated Value $3,703,523

  Last Listing Agent Caroline Perotti BELLA VIEW REALTY LLC

  12132 Montalcino Cir, Windermere, FL 34786
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  $1,375,000

  Sold Jun 12, 2026

  2635 Tryon Place, Windermere, FL 34786

  • 6 Beds
  • 4.5 Baths
  • 4,027 Sq Ft
  • Built 1997

  Last Sold Summary

  • 7% Below List Price
  • $341/SF
  • 7 Days On Market

  Current Estimated Value $1,381,541

  Last Listing Agent Nipul Shah REIKI REALTY LLC

  2635 Tryon Place, Windermere, FL 34786
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  $444,980

  Sold May 15, 2026

  13369 Gorgona Isle Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,767 Sq Ft
  • Built 2019

  Last Sold Summary

  • 3% Below List Price
  • $252/SF
  • 92 Days On Market

  Current Estimated Value $393,853

  Last Listing Agent Wendy Fischer PREMIER SOTHEBYS INT'L REALTY

  13369 Gorgona Isle Dr, Windermere, FL 34786
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  $590,000

  Sold Feb 24, 2026

  4533 River Gem Ave, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,406 Sq Ft
  • Built 2006

  Last Sold Summary

  • 6% Below List Price
  • $245/SF
  • 49 Days On Market

  Current Estimated Value $584,467

  Last Listing Agent George Stringer COLDWELL BANKER REALTY

  4533 River Gem Ave, Windermere, FL 34786
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  $292,000

  Sold Oct 03, 2025

  11434 Jasper Kay Terrace Unit 306, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,455 Sq Ft
  • Built 2007

  Last Sold Summary

  • 20% Below List Price
  • $201/SF
  • 348 Days On Market

  Current Estimated Value $300,822

  Last Listing Agent Jay Stewart SOUTHERN REALTY GROUP LLC

  11434 Jasper Kay Terrace Unit 306, Windermere, FL 34786
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  $490,000

  Sold May 11, 2026

  6310 Golden Dewdrop Trail, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,977 Sq Ft
  • Built 2012

  Last Sold Summary

  • 7% Below List Price
  • $248/SF
  • 107 Days On Market

  Current Estimated Value $495,956

  Last Listing Agent Mengshi Lu JOY ESTATE ENTERPRISE INC

  6310 Golden Dewdrop Trail, Windermere, FL 34786
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  $812,000

  Sold Apr 20, 2026

  2641 Hempel Ave, Windermere, FL 34786

  • 4 Beds
  • 2 Baths
  • 2,404 Sq Ft
  • Built 1985

  Last Sold Summary

  • 2% Below List Price
  • $338/SF
  • 11 Days On Market

  Current Estimated Value $808,276

  Last Listing Agent Frank Mediavilla KNIGHTS REALTY

  2641 Hempel Ave, Windermere, FL 34786
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  /2

  $512,200

  Sold May 12, 2026

  5130 Sun Palm Dr, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,723 Sq Ft
  • Built 1987

  Last Sold Summary

  • 2% Below List Price
  • $297/SF
  • 4 Days On Market

  Current Estimated Value $513,740

  Last Listing Agent Elle Walters JASON MITCHELL REAL ESTATE FLO

  5130 Sun Palm Dr, Windermere, FL 34786
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  $1,290,000

  Sold Oct 24, 2025

  13527 Lake Cawood Dr, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,379 Sq Ft
  • Built 2003

  Last Sold Summary

  • 1% Above List Price
  • $382/SF
  • 6 Days On Market

  Current Estimated Value $1,278,954

  Last Listing Agent Simon Simaan THE SIMON SIMAAN GROUP

  13527 Lake Cawood Dr, Windermere, FL 34786
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  /2

  $11,500,000

  Sold May 15, 2026

  5525 Isleworth Country Club Dr, Windermere, FL 34786

  • 5 Beds
  • 5.5 Baths
  • 9,511 Sq Ft
  • Built 1999

  Last Sold Summary

  • 19% Below List Price
  • $1,209/SF
  • 333 Days On Market

  Current Estimated Value $5,755,366

  Last Listing Agent Monica Lochmandy ISLEWORTH REALTY LLC

  5525 Isleworth Country Club Dr, Windermere, FL 34786
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  $430,000

  Sold Feb 06, 2026

  7411 Ripplepointe Way, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,948 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $221/SF
  • 55 Days On Market

  Current Estimated Value $430,890

  Last Listing Agent John Cunningham KELLER WILLIAMS CLASSIC

  7411 Ripplepointe Way, Windermere, FL 34786
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  /2

  $1,550,000

  Sold Jun 11, 2026

  6001 Caymus Loop, Windermere, FL 34786

  • 5 Beds
  • 5 Baths
  • 3,520 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $440/SF
  • 7 Days On Market

  Current Estimated Value $1,516,105

  Last Listing Agent Stella Freeman QUATTRO R E SOLUTIONS LLC

  6001 Caymus Loop, Windermere, FL 34786
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  $1,540,000

  Sold May 08, 2026

  8438 Tibet Butler Dr, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,464 Sq Ft
  • Built 1999

  Last Sold Summary

  • 7% Below List Price
  • $445/SF
  • 33 Days On Market

  Current Estimated Value $1,530,449

  Last Listing Agent Daniel Pavel WRA BUSINESS & REAL ESTATE

  8438 Tibet Butler Dr, Windermere, FL 34786
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  $285,000

  Sold Sep 19, 2025

  8277 Maritime Flag St Unit 205, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,455 Sq Ft
  • Built 2007

  Last Sold Summary

  • 10% Below List Price
  • $196/SF
  • 39 Days On Market

  Current Estimated Value $296,395

  Last Listing Agent Raymond Glenn LAKESIDE REALTY WINDERMERE INC

  8277 Maritime Flag St Unit 205, Windermere, FL 34786
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  $455,000

  Sold Jun 29, 2026

  13733 Bressler Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,002 Sq Ft
  • Built 2019

  Last Sold Summary

  • 3% Below List Price
  • $227/SF
  • 93 Days On Market

  Current Estimated Value $455,068

  Last Listing Agent Robert Welker, III CORCORAN PREMIER REALTY

  13733 Bressler Aly, Windermere, FL 34786
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  $365,000

  Sold Jul 03, 2026

  12210 Langstaff Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,480 Sq Ft
  • Built 2012

  Last Sold Summary

  • 3% Below List Price
  • $247/SF
  • 51 Days On Market

  Current Estimated Value $368,294

  Last Listing Agent Ernesto Cisneros ELITE REALTY ENTERPRISES LLC

  12210 Langstaff Dr, Windermere, FL 34786
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  /2

  $375,000

  Sold Apr 27, 2026

  12683 Langstaff Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,428 Sq Ft
  • Built 2003

  Last Sold Summary

  • $263/SF
  • 3 Days On Market

  Current Estimated Value $372,199

  Last Listing Agent Vlad Kizlo KELLER WILLIAMS REALTY AT THE LAKES

  12683 Langstaff Dr, Windermere, FL 34786
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  /2

  $580,000

  Sold Sep 22, 2025

  12867 Penshurst Ln, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $252/SF
  • 3 Days On Market

  Current Estimated Value $583,148

  Last Listing Agent Stefany Marcelino RE/MAX INNOVATION

  12867 Penshurst Ln, Windermere, FL 34786
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  $395,000

  Sold Jul 13, 2026

  7249 Shadeview Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,569 Sq Ft
  • Built 2016

  Last Sold Summary

  • 8% Below List Price
  • $252/SF
  • 78 Days On Market

  Current Estimated Value $392,404

  Last Listing Agent Blanca Armada REMAX PREMIER PROPERTIES

  7249 Shadeview Aly, Windermere, FL 34786
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  $675,000

  Sold Jul 10, 2026

  9376 Woodbreeze Blvd, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,026 Sq Ft
  • Built 1986

  Last Sold Summary

  • $333/SF
  • 11 Days On Market

  Current Estimated Value $668,441

  Last Listing Agent Kimberly Ann Zeidner, LLC CHARLES RUTENBERG REALTY ORLANDO

  9376 Woodbreeze Blvd, Windermere, FL 34786
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  $549,900

  Sold Jul 17, 2026

  9072 Woodbreeze Blvd, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Below List Price
  • $320/SF
  • 39 Days On Market

  Current Estimated Value $544,825

  Last Listing Agent Charles Kohlinger BHHS FLORIDA REALTY

  9072 Woodbreeze Blvd, Windermere, FL 34786
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  /2

  $1,050,000

  Sold May 21, 2026

  316 E 5th Ave, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,412 Sq Ft
  • Built 1962

  Last Sold Summary

  • 5% Below List Price
  • $435/SF
  • 22 Days On Market

  Current Estimated Value $1,040,267

  Last Listing Agent Darrell Nunnelley VINTAGE REALTY GROUP LLC

  316 E 5th Ave, Windermere, FL 34786
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  $1,400,000

  Sold Apr 08, 2026

  6023 Blakeford Dr, Windermere, FL 34786

  • 5 Beds
  • 3 Baths
  • 3,013 Sq Ft
  • Built 1999

  Last Sold Summary

  • 8% Below List Price
  • $465/SF
  • 9 Days On Market

  Current Estimated Value $1,388,089

  Last Listing Agent Angela Durruthy KEENE'S POINTE REALTY

  6023 Blakeford Dr, Windermere, FL 34786
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  /2

  $360,000

  Sold Jul 09, 2026

  14236 Oasis Cove Blvd, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft
  • Built 2011

  Last Sold Summary

  • 6% Below List Price
  • $238/SF
  • 66 Days On Market

  Current Estimated Value $363,650

  Last Listing Agent Raquel Saunders WRA BUSINESS & REAL ESTATE

  14236 Oasis Cove Blvd, Windermere, FL 34786
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  /2

  $890,000

  Sold Aug 11, 2026

  1002 Oakdale St, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,516 Sq Ft
  • Built 1973

  Last Sold Summary

  • 9% Below List Price
  • $253/SF
  • 97 Days On Market

  Current Estimated Value $970,503

  Last Listing Agent Frank Smith KELLER WILLIAMS SUBURBAN TAMPA

  1002 Oakdale St, 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 $815,900

  Last Listing Agent Judy Black UPSIDE REAL ESTATE INC

  416 Magnolia St, Windermere, FL 34786

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