Windermere, FL Homes

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  /31

  Est $328,443

  Not Listed For Sale

  8265 Maritime Flag St Unit 22b-5, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,476 Sq Ft
  • Built 2012

  8265 Maritime Flag St Unit 22b-5, Windermere, FL 34786

  Last Sold Summary

  • 3 Days On Market
• 

  

  

  /87

  $3,800,000

  • 5 Beds
  • 7 Baths
  • 7,120 Sq Ft

  12623 Park Ave, Windermere, FL 34786

  Experience Unparalleled Luxury in Chaine Du LacNestled within the sought- after gated community of Chaine Du Lac, this extraordinary custom estate redefines luxury living. Offering over 7,100 sqft of meticulously crafted living space, this magnificent residence features 5 bedrooms, 5 full bathrooms, and 2 half bathrooms, combining timeless elegance with exceptional craftsmanship in one of

  Mohamed Inshan ELEVATE REAL ESTATE BROKERS

  12623 Park Ave, Windermere, FL 34786
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  /2

  $560,000

  Sold May 29, 2026

  13237 Fossick Rd, Windermere, FL 34786

  • 4 Beds
  • 2 Baths
  • 2,516 Sq Ft
  • Built 2004

  Last Sold Summary

  • 7% Below List Price
  • $223/SF
  • 56 Days On Market

  Current Estimated Value $597,155

  Last Listing Agent Michael Collier EXP REALTY LLC

  13237 Fossick Rd, Windermere, FL 34786
• 

  

  

  /25

  Est $360,265

  Not Listed For Sale

  14324 Desert Haven St Unit 4001, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft
  • Built 2013

  14324 Desert Haven St Unit 4001, Windermere, FL 34786

  Last Sold Summary

  • 176 Days On Market
• 

  

  

  /50

  $670,000

  $25K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,297 Sq Ft

  8582 Powder Ridge Trail, Windermere, FL 34786

  AN IRRESISTIBLE INVESTMENT OPPORTUNITY — OR YOUR FIRST HOME!Welcome to this stunning Kipling model offering serene lake views and a host of exceptional upgrades. This home features fully paid-off solar panels, electric vehicle charging outlets, and a whole-house water filtration system for maximum efficiency and comfort. Step inside and enjoy the spacious loft above the garage, new carpeting,

  Mariana Rondon LPT REALTY, LLC

  8582 Powder Ridge Trail, Windermere, FL 34786
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  /2

  $1,755,000

  Sold Aug 15, 2025

  11856 Vinci Dr, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,680 Sq Ft
  • Built 2011

  Last Sold Summary

  • 5% Below List Price
  • $477/SF
  • 108 Days On Market

  Current Estimated Value $1,737,342

  Last Listing Agent Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

  11856 Vinci Dr, Windermere, FL 34786
• 

  

  /38

  Est $412,530

  Not Listed For Sale

  11685 Water Run Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,584 Sq Ft
  • Built 2017

  11685 Water Run Aly, Windermere, FL 34786

  Last Sold Summary

  • 38 Days On Market
• 

  

  /39

  $539,000

  • 4 Beds
  • 2.5 Baths
  • 2,221 Sq Ft

  7867 Berkshire Oak Aly, Windermere, FL 34786

  Luxury Living in the Heart of Windermere!Welcome to this beautifully maintained 4 bedrooms and 2.5 bathrooms, single family home, located in the highly desirable community of Windermere. Situated on a charming alley-style streetscape, this elegant property offers the perfect blend of comfort, style, and convenience in one of Central Florida’s most sought-after locations. This spacious home

  James Song MULTI CHOICE REALTY LLC

  7867 Berkshire Oak Aly, Windermere, FL 34786
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  /2

  $1,400,000

  Sold May 07, 2026

  17521 Black Rail St, Windermere, FL 34786

  • 6 Beds
  • 4.5 Baths
  • 5,316 Sq Ft
  • Built 2015

  Last Sold Summary

  • 11% Below List Price
  • $263/SF
  • 96 Days On Market

  Current Estimated Value $1,432,634

  Last Listing Agent Rebecca Puig CHARLES RUTENBERG REALTY ORLANDO

  17521 Black Rail St, Windermere, FL 34786
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  /16

  Not Listed For Sale

  8256 Maritime Flag St Unit 1725, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Built 2009

  8256 Maritime Flag St Unit 1725, Windermere, FL 34786

  Last Sold Summary

  • 69 Days On Market
• 

  

  /77

  $1,825,000

  • 4 Beds
  • 4.5 Baths
  • 4,549 Sq Ft

  11226 Macaw Ct, Windermere, FL 34786

  The Ultimate Entertainer’s Dream Home. Welcome to this exceptional custom-built courtyard estate by Bill Sauerwine, offering 4 bedrooms, 4.5 bathrooms, and 4,549 square feet of luxurious living in the highly sought-after Windermere area. Designed for both grand entertaining and everyday comfort, this stunning residence centers around a private courtyard pool, creating a true indoor-outdoor

  Sean Hooke LAKESIDE REALTY WINDERMERE INC

  11226 Macaw Ct, Windermere, FL 34786
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  /2

  $1,045,000

  Sold Jan 20, 2026

  8764 Lookout Pointe Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,423 Sq Ft
  • Built 2015

  Last Sold Summary

  • 4% Below List Price
  • $305/SF
  • 71 Days On Market

  Current Estimated Value $1,018,783

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  8764 Lookout Pointe Dr, Windermere, FL 34786
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  /24

  Not Listed For Sale

  14348 Desert Haven St Unit 14348, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft
  • Built 2013

  14348 Desert Haven St Unit 14348, Windermere, FL 34786

  Last Sold Summary

  • 69 Days On Market
• 

  

  /24

  $415,000

  $374K PRICE INCREASE

  • 2 Beds
  • 2.5 Baths
  • 1,429 Sq Ft

  12405 Cruxbury Dr, Windermere, FL 34786

  Discover this spotless corner-unit townhome in Windermere Lakes, offering some privacy with a serene conservation area behind the home and no neighbors on one side. The open-concept layout seamlessly connects the kitchen to the living area, creating an inviting space for everyday living and entertaining. The kitchen features stainless steel appliances, 42” cabinets, added custom cabinetry, and

  Steve Lang HOMEVEST REALTY

  12405 Cruxbury Dr, Windermere, FL 34786
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  /2

  $670,000

  Sold Sep 09, 2025

  9473 Palm Tree Dr, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,084 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Below List Price
  • $321/SF
  • 7 Days On Market

  Current Estimated Value $671,629

  Last Listing Agent Mike Long COLDWELL BANKER REALTY

  9473 Palm Tree Dr, Windermere, FL 34786
• 

  

  /23

  Est $435,817

  Not Listed For Sale

  8650 Wellington Blue Ln, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,631 Sq Ft
  • Built 2016

  8650 Wellington Blue Ln, Windermere, FL 34786

  Last Sold Summary

  • 19 Days On Market
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  /34

  $510,000

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

  13324 Longacre Dr, Windermere, FL 34786

  Welcome to this beautifully maintained and exceptionally spacious one-story home located in the highly desirable Windermere Terrace community in the heart of Windermere. Offering 3 bedrooms, 2 bathrooms, plus a large dedicated office/flex room, this home provides the perfect blend of comfort, functionality, and style for today's lifestyle. From the moment you enter, you'll appreciate the open and

  James Song MULTI CHOICE REALTY LLC

  13324 Longacre Dr, Windermere, FL 34786
• 

  /2

  $475,000

  Sold Oct 23, 2025

  9375 Woodbreeze Blvd, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft
  • Built 1986

  Last Sold Summary

  • 23% Below List Price
  • $318/SF
  • 136 Days On Market

  Current Estimated Value $481,950

  Last Listing Agent Jackie Victoria Patellis COLDWELL BANKER REALTY

  9375 Woodbreeze Blvd, Windermere, FL 34786
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  /36

  Est $414,759

  Not Listed For Sale

  11618 Water Run Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,584 Sq Ft
  • Built 2017

  11618 Water Run Aly, Windermere, FL 34786

  Last Sold Summary

  • 116 Days On Market
• 

  

  /37

  $364,900

  Pending

  • 2 Beds
  • 2.5 Baths
  • 1,360 Sq Ft

  12981 Borland St, Windermere, FL 34786

  Skip the stress of renovations and step into a lifestyle of ease with this impeccably updated Windermere retreat where every major detail has been handled for you! Roof (2024), A/C (2023), Hot Water Heater (2024), this home offers the rare peace of mind that comes with a truly turnkey property. This home’s interior is bathed in natural light, showcasing beautiful luxury vinyl and ceramic tile

  Jennifer Garrison GARRISON REALTY GROUP LLC

  12981 Borland St, Windermere, FL 34786

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