Recently Sold Windermere, FL Homes

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  $400,000 Sold Nov 18, 2025

  14466 Bridgewater Crossings Blvd, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 1,642 Sq Ft
  • Built 2006

  Last Sold Summary

  • 6% Below List Price
  • $244/SF
  • 87 Days On Market

  Last Listing Agent Tennille Biggers KELLER WILLIAMS ELITE PARTNERS III REALTY

  14466 Bridgewater Crossings Blvd, Windermere, FL 34786
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  $540,000 Sold Jun 26, 2025

  8607 Crescendo Ave, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,073 Sq Ft
  • Built 2014

  Last Sold Summary

  • 5% Below List Price
  • $260/SF
  • 6 Days On Market

  Current Estimated Value $546,698

  Last Listing Agent Shirlei Devito CENTURY 21 CARIOTI

  8607 Crescendo Ave, Windermere, FL 34786
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  $675,000 Sold Apr 11, 2025

  11725 Sprawling Oak Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,591 Sq Ft
  • Built 2016

  Last Sold Summary

  • 1% Below List Price
  • $261/SF
  • 5 Days On Market

  Current Estimated Value $675,199

  Last Listing Agent Alexandra Mateu BAHIA INTERNATIONAL REALTY

  11725 Sprawling Oak Dr, Windermere, FL 34786
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  $580,000 Sold Apr 11, 2025

  8329 Lookout Pointe Dr, Windermere, FL 34786

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

  Last Sold Summary

  • 3% Below List Price
  • $220/SF
  • 56 Days On Market

  Current Estimated Value $587,492

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

  8329 Lookout Pointe Dr, Windermere, FL 34786
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  $1,050,000 Sold Sep 23, 2025

  5232 Tildens Grove Blvd, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,079 Sq Ft
  • Built 2005

  Last Sold Summary

  • 9% Below List Price
  • $341/SF
  • 17 Days On Market

  Last Listing Agent Steve Healy CORCORAN PREMIER REALTY

  5232 Tildens Grove Blvd, Windermere, FL 34786
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  $1,950,000 Sold Oct 20, 2025

  1984 Windermere Rd, Windermere, FL 34786

  • 6 Beds
  • 5.5 Baths
  • 6,601 Sq Ft
  • Built 2014

  Last Sold Summary

  • 10% Below List Price
  • $295/SF
  • 180 Days On Market

  Last Listing Agent Steven Ritz KELLER WILLIAMS WINTER PARK

  1984 Windermere Rd, Windermere, FL 34786
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  $974,900 Sold Jul 02, 2025

  8778 Peachtree Park Ct, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,235 Sq Ft
  • Built 2017

  Last Sold Summary

  • 1% Below List Price
  • $301/SF
  • 16 Days On Market

  Last Listing Agent Ronald Haywood BHHS FLORIDA REALTY

  8778 Peachtree Park Ct, Windermere, FL 34786
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  $1,120,000 Sold Nov 20, 2025

  1927 Watermere Ln, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,053 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Below List Price
  • $367/SF
  • 11 Days On Market

  Last Listing Agent Guang Yang YOUR HOME SOLD GUARANTEED REALTY

  1927 Watermere Ln, Windermere, FL 34786
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  $1,700,000 Sold Oct 27, 2025

  5243 W Lake Butler Rd, Windermere, FL 34786

  • 3 Beds
  • 3 Baths
  • 3,255 Sq Ft
  • Built 1996

  Last Sold Summary

  • 46% Below List Price
  • $522/SF
  • 211 Days On Market

  Last Listing Agent Andrew Burgard CHARLES RUTENBERG REALTY ORLANDO

  5243 W Lake Butler Rd, Windermere, FL 34786
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  $3,500,000 Sold Apr 11, 2025

  5188 Isleworth Country Club Dr, Windermere, FL 34786

  • Land
  • 0.73 Acre
  • $4,794,521 per Acre

  Last Sold Summary

  • 0 Days On Market

  Current Estimated Value $3,434,596

  Last Listing Agent Carey Sheffield ISLEWORTH REALTY LLC

  5188 Isleworth Country Club Dr, Windermere, FL 34786
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  $370,000 Sold Sep 03, 2025

  7348 Yoder St, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,479 Sq Ft
  • Built 2008

  Last Sold Summary

  • 11% Below List Price
  • $250/SF
  • 95 Days On Market

  Current Estimated Value $367,830

  Last Listing Agent Christopher Gabriel EXP REALTY LLC

  7348 Yoder St, Windermere, FL 34786
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  $1,070,000 Sold Sep 30, 2025

  9641 Crown Prince Ln, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,924 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $273/SF
  • 2 Days On Market

  Last Listing Agent Anderson Tiu REIKI REALTY LLC

  9641 Crown Prince Ln, Windermere, FL 34786
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  $1,563,888 Sold Jan 24, 2025

  5856 Marleon Dr, Windermere, FL 34786

  • 5 Beds
  • 6.5 Baths
  • 4,506 Sq Ft
  • Built 2015

  Last Sold Summary

  • 3% Below List Price
  • $347/SF
  • 13 Days On Market

  Current Estimated Value $1,594,258

  Last Listing Agent Xiaoyu Su RATIO REAL ESTATE, LLC

  5856 Marleon Dr, Windermere, FL 34786
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  $850,000 Sold Jun 26, 2025

  2532 Waterview Place, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,478 Sq Ft
  • Built 1978

  Last Sold Summary

  • $343/SF
  • 21 Days On Market

  Current Estimated Value $841,074

  Last Listing Agent Tammy Schuster COMPASS FLORIDA LLC

  2532 Waterview Place, Windermere, FL 34786
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  $378,250 Sold Jul 08, 2025

  12963 Garridan Ave, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,535 Sq Ft
  • Built 2009

  Last Sold Summary

  • 3% Below List Price
  • $246/SF
  • 6 Days On Market

  Current Estimated Value $369,454

  Last Listing Agent Chase Morton Tate COMPASS FLORIDA LLC

  12963 Garridan Ave, Windermere, FL 34786
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  $845,000 Sold May 15, 2025

  6244 Little Lake Sawyer Dr, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 3,300 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Below List Price
  • $256/SF
  • 42 Days On Market

  Current Estimated Value $834,083

  Last Listing Agent Michael Spina INDEPENDENCE REALTY LLC

  6244 Little Lake Sawyer Dr, Windermere, FL 34786
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  $1,175,000 Sold Jul 10, 2025

  11335 Winston Willow Ct, Windermere, FL 34786

  • 5 Beds
  • 3 Baths
  • 2,885 Sq Ft
  • Built 1990

  Last Sold Summary

  • 2% Below List Price
  • $407/SF
  • 10 Days On Market

  Current Estimated Value $1,158,607

  Last Listing Agent Valerie Winch REALTY HUB

  11335 Winston Willow Ct, Windermere, FL 34786
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  $2,500,000 Sold Sep 24, 2025

  5138 Fairway Oaks Dr, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 4,330 Sq Ft
  • Built 1994

  Last Sold Summary

  • 22% Below List Price
  • $577/SF
  • 169 Days On Market

  Last Listing Agent Rob Rahter STOCKWORTH REALTY GROUP

  5138 Fairway Oaks Dr, Windermere, FL 34786
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  $1,133,431 Sold Jul 02, 2025

  14415 Crest Palm Ave, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 3,764 Sq Ft
  • Built 2025

  Last Sold Summary

  • $301/SF
  • 0 Days On Market

  Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  14415 Crest Palm Ave, Windermere, FL 34786
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  $812,000 Sold Jul 25, 2025

  8330 Vivaro Isle Way, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 3,465 Sq Ft
  • Built 2018

  Last Sold Summary

  • 7% Below List Price
  • $234/SF
  • 112 Days On Market

  Current Estimated Value $825,440

  Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

  8330 Vivaro Isle Way, Windermere, FL 34786
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  $1,040,000 Sold Mar 19, 2025

  14243 Crest Palm Ave, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 3,550 Sq Ft
  • Built 2025

  Last Sold Summary

  • $293/SF

  Current Estimated Value $1,043,745

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  14243 Crest Palm Ave, Windermere, FL 34786
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  $655,000 Sold Apr 29, 2025

  7343 Derexa Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,612 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $251/SF
  • 77 Days On Market

  Current Estimated Value $646,654

  Last Listing Agent Phillip Mariani EXP REALTY LLC

  7343 Derexa Dr, Windermere, FL 34786
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  $986,000 Sold Oct 10, 2025

  6905 Cucamelon Ct, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,232 Sq Ft
  • Built 2021

  Last Sold Summary

  • 10% Below List Price
  • $305/SF
  • 61 Days On Market

  Last Listing Agent Marisol Goncalvez De Ayala AGENT TRUST REALTY CORPORATION

  6905 Cucamelon Ct, Windermere, FL 34786
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  $1,400,000 Sold Jul 17, 2025

  3326 Butler Bay Dr N, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,650 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $384/SF
  • 43 Days On Market

  Current Estimated Value $1,360,082

  Last Listing Agent Marc Holland BOARDWALK REALTY, LLC

  3326 Butler Bay Dr N, Windermere, FL 34786
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  $435,000 Sold Jun 06, 2025

  13330 Abuela Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,663 Sq Ft
  • Built 2020

  Last Sold Summary

  • 4% Below List Price
  • $262/SF
  • 174 Days On Market

  Current Estimated Value $434,908

  Last Listing Agent Paul Richards CORCORAN PREMIER REALTY

  13330 Abuela Aly, Windermere, FL 34786
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  $1,450,000 Sold Jun 20, 2025

  5950 Blakeford Dr, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,996 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Below List Price
  • $484/SF
  • 11 Days On Market

  Current Estimated Value $1,443,909

  Last Listing Agent Jared Jones REVEL REALTY LLC

  5950 Blakeford Dr, Windermere, FL 34786
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  $432,500 Sold Oct 30, 2025

  8942 Matriarca Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,686 Sq Ft
  • Built 2020

  Last Sold Summary

  • 6% Below List Price
  • $257/SF
  • 38 Days On Market

  Last Listing Agent Alexandra Lattuf ANCHOR REAL ESTATE

  8942 Matriarca Aly, Windermere, FL 34786
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  $1,510,000 Sold Jul 10, 2025

  6241 Blakeford Dr, Windermere, FL 34786

  • 4 Beds
  • 4 Baths
  • 3,556 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Below List Price
  • $425/SF
  • 114 Days On Market

  Current Estimated Value $1,515,757

  Last Listing Agent Angela Durruthy KEENE'S POINTE REALTY

  6241 Blakeford Dr, Windermere, FL 34786
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  $2,800,000 Sold Mar 26, 2025

  9632 Weatherstone Ct, Windermere, FL 34786

  • 5 Beds
  • 8 Baths
  • 7,239 Sq Ft
  • Built 2007

  Last Sold Summary

  • 7% Below List Price
  • $387/SF
  • 18 Days On Market

  Current Estimated Value $2,629,041

  Last Listing Agent Matt Tomaszewski CORCORAN PREMIER REALTY

  9632 Weatherstone Ct, Windermere, FL 34786
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  $1,004,000 Sold Jun 09, 2025

  1912 Westover Reserve Blvd, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,937 Sq Ft
  • Built 1999

  Last Sold Summary

  • 3% Below List Price
  • $255/SF
  • 11 Days On Market

  Current Estimated Value $1,008,680

  Last Listing Agent Rebekkah Boskovich REVEL REALTY LLC

  1912 Westover Reserve Blvd, Windermere, FL 34786
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  $1,600,000 Sold May 31, 2025

  3414 Cocard Ct, Windermere, FL 34786

  • 6 Beds
  • 5 Baths
  • 6,098 Sq Ft
  • Built 1998

  Last Sold Summary

  • 16% Below List Price
  • $262/SF
  • 58 Days On Market

  Current Estimated Value $1,693,609

  Last Listing Agent Zoheb Sajan RUSSU REALTY & ASSOCIATES PA

  3414 Cocard Ct, Windermere, FL 34786
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  $1,440,000 Sold Dec 27, 2024

  11313 Shandon Park Way, Windermere, FL 34786

  • 6 Beds
  • 5 Baths
  • 4,032 Sq Ft
  • Built 2005

  Last Sold Summary

  • 14% Below List Price
  • $357/SF
  • 80 Days On Market

  Current Estimated Value $1,399,528

  Last Listing Agent Cheryl Gritzer CLOCK TOWER REALTY

  11313 Shandon Park Way, Windermere, FL 34786
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  $840,000 Sold Jun 30, 2025

  9036 Arbors Edge Trail, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,835 Sq Ft
  • Built 2017

  Last Sold Summary

  • 16% Below List Price
  • $296/SF
  • 168 Days On Market

  Current Estimated Value $821,002

  Last Listing Agent Eduardo Pavone ON ME REALTY

  9036 Arbors Edge Trail, Windermere, FL 34786
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  $470,000 Sold Nov 03, 2025

  6864 Helmsley Cir, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,609 Sq Ft
  • Built 2009

  Last Sold Summary

  • 3% Below List Price
  • $292/SF
  • 18 Days On Market

  Last Listing Agent Stephanie Pitts KELLER WILLIAMS CLASSIC

  6864 Helmsley Cir, Windermere, FL 34786
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  $1,350,000 Sold Apr 18, 2025

  Unlisted Address

  • 4 Beds
  • 4.5 Baths
  • 3,785 Sq Ft
  • Built 2005

  Last Sold Summary

  • $357/SF

  Current Estimated Value $1,349,505

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  Unlisted Address
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  $670,000 Sold May 30, 2025

  8272 Procida Isle Ln, Windermere, FL 34786

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

  Last Sold Summary

  • 3% Below List Price
  • $301/SF
  • 3 Days On Market

  Current Estimated Value $676,320

  Last Listing Agent Oscar Brea LA ROSA RTY WINTER GARDEN LLC

  8272 Procida Isle Ln, Windermere, FL 34786
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  $1,131,350 Sold Mar 03, 2025

  1548 Lake Rhea Dr, Windermere, FL 34786

  • 4 Beds
  • 4 Baths
  • 3,413 Sq Ft
  • Built 2003

  Last Sold Summary

  • 12% Below List Price
  • $331/SF
  • 83 Days On Market

  Current Estimated Value $1,124,272

  Last Listing Agent Joshua Torres LIFESTYLE INTERNATIONAL REALTY

  1548 Lake Rhea Dr, Windermere, FL 34786
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  $797,000 Sold Oct 17, 2025

  1932 Reed Hill Dr, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,867 Sq Ft
  • Built 2002

  Last Sold Summary

  • 10% Below List Price
  • $278/SF
  • 101 Days On Market

  Last Listing Agent Michael blank FL PRO BROKERS LLC

  1932 Reed Hill Dr, Windermere, FL 34786
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  $1,280,000 Sold May 15, 2025

  13628 Lake Cawood Dr, Windermere, FL 34786

  • 4 Beds
  • 5 Baths
  • 4,505 Sq Ft
  • Built 1998

  Last Sold Summary

  • 5% Below List Price
  • $284/SF
  • 1 Day On Market

  Current Estimated Value $1,291,498

  Last Listing Agent Hector Leon LPT REALTY, LLC

  13628 Lake Cawood Dr, Windermere, FL 34786
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  $505,000 Sold Apr 18, 2025

  13832 Summerport Trail Loop, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,245 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $225/SF
  • 91 Days On Market

  Current Estimated Value $523,168

  Last Listing Agent Patricia Schraiber DENIZ REALTY PARTNERS LLC

  13832 Summerport Trail Loop, Windermere, FL 34786

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