Windermere, FL Homes

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  $830,000

  Sold Jan 16, 2026

  11031 Ledgement Ln, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 2,788 Sq Ft
  • Built 2003

  Last Sold Summary

  • 8% Below List Price
  • $298/SF
  • 178 Days On Market

  Current Estimated Value $835,994

  Last Listing Agent Billy Wygle THE WILKINS WAY LLC

  11031 Ledgement Ln, Windermere, FL 34786
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  /37

  Est $2,514,757

  Not Listed For Sale

  6127 Orta Ct, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 4,685 Sq Ft
  • Built 2015

  6127 Orta Ct, Windermere, FL 34786

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Dianna Desboyaux DOUGLAS ELLIMAN
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  /84

  $1,740,000

  $45K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,680 Sq Ft

  8241 Tibet Butler Dr, Windermere, FL 34786

  Perfectly positioned on the 8th fairway of the renowned Golden Bear Golf Course in Keene's Pointe, this stunning Victorian estate offers timeless elegance, exceptional craftsmanship, and breathtaking golf course views. A grand foyer welcomes you with an impressive circular staircase, setting the stage for the home's sophisticated design and gracious living spaces.The gourmet kitchen is a

  Bob Guidice GOLFPARK PROPERTIES

  8241 Tibet Butler Dr, Windermere, FL 34786
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  /2

  $753,000

  Sold May 27, 2026

  7519 Brofield Ave, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,628 Sq Ft
  • Built 2009

  Last Sold Summary

  • $287/SF
  • 4 Days On Market

  Current Estimated Value $735,145

  Last Listing Agent Diana Plesca EXP REALTY LLC

  7519 Brofield Ave, Windermere, FL 34786
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  /37

  Est $428,185

  Not Listed For Sale

  8368 Iron Mountain Trail, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 1,760 Sq Ft
  • Built 2016

  8368 Iron Mountain Trail, Windermere, FL 34786

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Thomas Bayrouty, Jr REDFIN CORPORATION
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  /63

  $4,100,000

  $350K PRICE DROP

  • 3 Beds
  • 5 Baths
  • 5,004 Sq Ft

  9144 Isleworth Gardens Dr, Windermere, FL 34786

  Experience refined luxury living in this extraordinary 5,004-square-foot garden villa estate nestled within Isleworth Golf & Country Club. This impeccably designed residence offers three expansive bedrooms, each with its own beautifully appointed en-suite bathroom, along with two elegant half baths to accommodate guests with ease. From the moment you arrive, the home’s striking

  Megan Dowdy MEGAN DOWDY REALTY, LLC

  9144 Isleworth Gardens Dr, Windermere, FL 34786
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  /2

  $1,875,000

  Sold Jul 24, 2026

  6036 Greatwater Dr, Windermere, FL 34786

  • 4 Beds
  • 4.5 Baths
  • 4,013 Sq Ft
  • Built 2001

  Last Sold Summary

  • 6% Below List Price
  • $467/SF
  • 55 Days On Market

  Current Estimated Value $2,027,940

  Last Listing Agent Rob Rahter STOCKWORTH REALTY GROUP

  6036 Greatwater Dr, Windermere, FL 34786
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  /50

  Est $567,480

  Not Listed For Sale

  7861 Berkshire Oak Aly, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,214 Sq Ft
  • Built 2018

  7861 Berkshire Oak Aly, Windermere, FL 34786

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Julie Bettosini STOCKWORTH REALTY GROUP
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  /63

  $2,170,000

  $210K PRICE DROP Pending

  • 5 Beds
  • 6.5 Baths
  • 5,448 Sq Ft

  1316 Estancia Woods Loop, Windermere, FL 34786

  Elegant and spacious home in the highly sought after Estancia at Windermere community, offering the perfect blend of luxury, comfort, and prime Central Florida living. Built in 2019 on an oversized homesite, this beautifully appointed residence showcases modern architecture, generous living areas filled with natural light, and high end finishes throughout. The open concept layout is ideal for

  catalina gomez EXP REALTY LLC

  1316 Estancia Woods Loop, Windermere, FL 34786
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  /2

  $600,000

  Sold Dec 15, 2025

  12925 Holdenbury Ln, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,981 Sq Ft
  • Built 2013

  Last Sold Summary

  • 4% Below List Price
  • $201/SF
  • 98 Days On Market

  Current Estimated Value $620,919

  Last Listing Agent Eric Nelson SIGNATURE HOMES

  12925 Holdenbury Ln, Windermere, FL 34786
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  /25

  Est $372,231

  Not Listed For Sale

  12852 Calderdale Ave, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,505 Sq Ft
  • Built 2010

  12852 Calderdale Ave, Windermere, FL 34786

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Daniel Goodman CHARLES RUTENBERG REALTY ORLANDO
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  $570,000

  $15K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  12789 Bosworth Ave, Windermere, FL 34786

  Under contract-accepting backup offers. This stunning Ashton Woods home in the highly sought-after Wickham Park community of Windermere truly shows like a model. Built in 2012, this beautifully maintained single-story home offers 3 bedrooms, 2 bathrooms, and a 2-car garage. The bright, open-concept floor plan features laminate flooring and is perfect for both everyday living and entertaining. The

  Joy Tucker FLORIDA HOMES REALTY & MORTGAGE

  12789 Bosworth Ave, Windermere, FL 34786
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  /2

  $619,000

  Sold Dec 18, 2025

  8776 Crescendo Ave, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,072 Sq Ft
  • Built 2016

  Last Sold Summary

  • $299/SF
  • 4 Days On Market

  Current Estimated Value $623,465

  Last Listing Agent Matt Kester THE REAL ESTATE COLLECTION LLC

  8776 Crescendo Ave, Windermere, FL 34786
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  /2

  Est $753,297

  Not Listed For Sale

  9156 Outlook Rock Trail, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,319 Sq Ft
  • Built 2016

  9156 Outlook Rock Trail, Windermere, FL 34786

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Umberto Da Cunha Neto WRA BUSINESS & REAL ESTATE
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  $435,000

  • 3 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  12988 Borland St, Windermere, FL 34786

  Welcome to 12988 Borland Street in sought-after Wickham Park, where comfort, convenience, and low-maintenance living come together in the heart of Windermere.This beautifully maintained 3-bedroom, 2.5-bath townhome offers a bright, open floor plan designed for modern living. Natural light fills the spacious living and dining areas, highlighting the ceramic tile flooring throughout the main

  Shawn Kerwin LOKATION

  12988 Borland St, Windermere, FL 34786
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  /2

  $450,000

  Sold Apr 23, 2026

  8601 Via Tavoleria Way, Windermere, FL 34786

  • 3 Beds
  • 3.5 Baths
  • 1,936 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $232/SF
  • 5 Days On Market

  Current Estimated Value $450,781

  Last Listing Agent Liza Farzati SERHANT

  8601 Via Tavoleria Way, Windermere, FL 34786
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  /2

  Est $1,094,909

  Not Listed For Sale

  13981 Reams Rd, Windermere, FL 34786

  13981 Reams Rd, Windermere, FL 34786

  Last Sold Summary

  • 111 Days On Market

  Last Listing Agent Fernando Perez de Armas AXEN REALTY, LLC
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  $1,318,000

  • 6 Beds
  • 4 Baths
  • 3,900 Sq Ft

  11768 Hampstead St, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Nestled within the prestigious Enclave at Windermere, this stunning Mediterranean-style residence delivers the Florida luxury lifestyle in every detail — from the moment you step through the rustic wooden front door. Soaring 10-foot ceilings and large-format 24x24 white and grey-veined porcelain tile set the tone for the main level. To the right,

  Caroline De Castro Marcellini COMPASS FLORIDA, LLC

  11768 Hampstead St, Windermere, FL 34786
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  /2

  $565,000

  Sold Sep 29, 2025

  6545 Chagford Ln, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,265 Sq Ft
  • Built 2007

  Last Sold Summary

  • $249/SF

  Current Estimated Value $564,689

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

  6545 Chagford Ln, Windermere, FL 34786
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  /37

  Est $383,954

  Not Listed For Sale

  8213 Mystic View Way Unit 2903, Windermere, FL 34786

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

  8213 Mystic View Way Unit 2903, Windermere, FL 34786

  Last Sold Summary

  • 88 Days On Market

  Last Listing Agent Shaun Reed KELLER WILLIAMS CLASSIC

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