Windermere, FL Homes

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  $340,000

  Sold Feb 06, 2026

  12716 Langstaff Dr, Windermere, FL 34786

  • 2 Beds
  • 2.5 Baths
  • 1,181 Sq Ft
  • Built 2003

  Last Sold Summary

  • 9% Below List Price
  • $288/SF
  • 85 Days On Market

  Current Estimated Value $334,462

  Last Listing Agent Ann Wargo UPSIDE REAL ESTATE INC

  12716 Langstaff Dr, Windermere, FL 34786
• 

  

  /2

  Est $686,754

  Not Listed For Sale

  11725 Sprawling Oak Dr, Windermere, FL 34786

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

  11725 Sprawling Oak Dr, Windermere, FL 34786

  Last Sold Summary

  • 5 Days On Market
• 

  

  

  /91

  $3,699,888

  $99K PRICE DROP Pending

  • 4 Beds
  • 5.5 Baths
  • 6,054 Sq Ft

  12812 Jacob Grace Ct, Windermere, FL 34786

  Under contract-accepting backup offers. Experience Unmatched Lakeside Luxury in a Custom-Built MasterpieceDiscover the pinnacle of elegance and tranquility in this exquisite custom-built estate, ideally positioned on an expansive lot within an exclusive guard-gated community. With direct access to a crystal-clear spring-fed lake that permits private boat docks, this home offers a rare blend

  Alireza Partovi EXP REALTY LLC

  12812 Jacob Grace Ct, Windermere, FL 34786
• 

  

  /2

  $498,000

  Sold Aug 01, 2025

  4813 River Gem Ave, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,085 Sq Ft
  • Built 2006

  Last Sold Summary

  • 9% Below List Price
  • $239/SF
  • 55 Days On Market

  Current Estimated Value $518,754

  Last Listing Agent Suzanne Hosmer RE/MAX SELECT GROUP

  4813 River Gem Ave, Windermere, FL 34786
• 

  

  /2

  Est $499,833

  Not Listed For Sale

  8255 Bryce Canyon Ave, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 1,840 Sq Ft
  • Built 2016

  8255 Bryce Canyon Ave, Windermere, FL 34786

  Last Sold Summary

  • 6 Days On Market
• 

  

  /67

  $2,550,000

  • 5 Beds
  • 7 Baths
  • 5,036 Sq Ft

  6288 Blakeford Dr, Windermere, FL 34786

  Positioned on a corner homesite along the 18th hole of the Golden Bear Club within the guard-gated community of Keene's Pointe, this thoughtfully updated custom home offers five bedrooms, four full bathrooms, and three half bathrooms, combining exceptional golf-front living with breathtaking views of the golf course, pool, and surrounding landscape. A grand foyer welcomes guests with a soaring

  Keith Renner NECTAR REAL ESTATE

  6288 Blakeford Dr, Windermere, FL 34786
• 

  /2

  $1,560,000

  Sold Aug 11, 2025

  8437 Lake Burden Cir, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,797 Sq Ft
  • Built 2005

  Last Sold Summary

  • 16% Below List Price
  • $411/SF
  • 105 Days On Market

  Current Estimated Value $1,558,358

  Last Listing Agent Daniela de Rodriguez B LIVE COMMERCIAL AND RESIDENT

  8437 Lake Burden Cir, Windermere, FL 34786
• 

  /2

  Est $547,780

  Not Listed For Sale

  6352 Golden Dewdrop Trail, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,984 Sq Ft
  • Built 2012

  6352 Golden Dewdrop Trail, Windermere, FL 34786

  Last Sold Summary

  • 15 Days On Market
• 

  

  /60

  $1,250,000

  Pending

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

  2127 Lilypad Ln, Windermere, FL 34786

  Under contract-accepting backup offers. Welcome to a rare opportunity in the highly sought-after Willows at Lake Rhea, where incredible design, extensive upgrades, and an elevated Windermere lifestyle come together on a private 1⁄2-acre cul-de-sac lot in one of Central Florida’s most desirable luxury communities. This exceptional 4-bedroom, 3-bath residence features a thoughtfully designed split

  Angela Jaspon UNITED REAL ESTATE PREFERRED

  2127 Lilypad Ln, Windermere, FL 34786
• 

  /2

  $3,350,000

  Sold Jul 15, 2025

  5801 Marleon Dr, Windermere, FL 34786

  • 6 Beds
  • 6.5 Baths
  • 6,968 Sq Ft
  • Built 1997

  Last Sold Summary

  • 7% Below List Price
  • $481/SF
  • 5 Days On Market

  Current Estimated Value $3,377,972

  Last Listing Agent Michelle Brierley COLDWELL BANKER REALTY

  5801 Marleon Dr, Windermere, FL 34786
• 

  /2

  Est $490,464

  Not Listed For Sale

  8321 Bryce Canyon Ave, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,891 Sq Ft
  • Built 2016

  8321 Bryce Canyon Ave, Windermere, FL 34786

  Last Sold Summary

  • 47 Days On Market
• 

  

  /57

  $489,500

  • 3 Beds
  • 2.5 Baths
  • 1,825 Sq Ft

  8266 Bryce Canyon Ave, Windermere, FL 34786

  JUST LISTED IN WINDERMERE – INCREDIBLE VALUE IN ONE OF CENTRAL FLORIDA'S MOST DESIRABLE COMMUNITIES If you've been searching for the perfect combination of location, condition, lifestyle, and value, this is the home you've been waiting for. Welcome to this beautifully maintained single-family home in the highly sought-after Windermere area, offering an opportunity that's becoming harder and

  Mahmoud Mango DALTON WADE INC

  8266 Bryce Canyon Ave, Windermere, FL 34786
• 

  /2

  $740,000

  Sold Jan 08, 2026

  11849 Cave Run Ave, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,414 Sq Ft
  • Built 2014

  Last Sold Summary

  • 11% Below List Price
  • $217/SF
  • 86 Days On Market

  Current Estimated Value $740,190

  Last Listing Agent Any Alves WRA BUSINESS & REAL ESTATE

  11849 Cave Run Ave, Windermere, FL 34786
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  /30

  Est $681,676

  Not Listed For Sale

  8267 Procida Isle Ln, Windermere, FL 34786

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

  8267 Procida Isle Ln, Windermere, FL 34786

  Last Sold Summary

  • 88 Days On Market
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  /35

  $5,490,000

  $370K PRICE DROP Pre-Foreclosure

  • 4 Beds
  • 7 Baths
  • 7,872 Sq Ft

  12264 Montalcino Cir, Windermere, FL 34786

  Lakefront, Luxurious, home with Private Pool in Windermere. A True Paradise! Discover this rare gem in the heart of Windermere,located in the gated community of Casa Del Lago — a spectacular residence that combines sophistication, comfort, and stunning lake views. with over eight expertly designed rooms, this home was carefully customized by the builder down to the smallest detail — from

  Jennifer Paiano Olmeda WRA BUSINESS & REAL ESTATE

  12264 Montalcino Cir, Windermere, FL 34786
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  /2

  $1,210,000

  Sold May 22, 2026

  13734 Lake Cawood Dr, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 4,437 Sq Ft
  • Built 2006

  Last Sold Summary

  • 34% Below List Price
  • $273/SF
  • 64 Days On Market

  Current Estimated Value $1,331,829

  Last Listing Agent Angela Schifano CHARLES RUTENBERG REALTY ORLANDO

  13734 Lake Cawood Dr, Windermere, FL 34786
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  /33

  Est $498,695

  Not Listed For Sale

  8553 Crescendo Ave, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,841 Sq Ft
  • Built 2016

  8553 Crescendo Ave, Windermere, FL 34786

  Last Sold Summary

  • 26 Days On Market
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  /78

  $1,900,000

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

  6110 Keenes Pointe Dr, Windermere, FL 34786

  Welcome to a truly exceptional custom home in Keene's Pointe, one of Windermere’s most sought-after guard-gated communities. Built by W. J. Sauerwine and set on a beautifully landscaped .43-acre homesite with mature oak trees, this residence offers a rare combination of privacy, thoughtful design, and extensive modern upgrades.This 4-bedroom plus office, 4-bath home features a highly

  Donna Calhoun KELLER WILLIAMS CLASSIC

  6110 Keenes Pointe Dr, Windermere, FL 34786
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  /2

  $290,000

  Sold May 21, 2026

  11564 Mizzon Dr Unit 202 (919), Windermere, FL 34786

  • 2 Beds
  • 2 Baths
  • 1,161 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $250/SF
  • 35 Days On Market

  Current Estimated Value $295,839

  Last Listing Agent Nilufer Rohleder COLDWELL BANKER REALTY

  11564 Mizzon Dr Unit 202 (919), Windermere, FL 34786
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  /2

  Est $1,416,380

  Not Listed For Sale

  11769 Hampstead St, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 4,979 Sq Ft
  • Built 2016

  11769 Hampstead St, Windermere, FL 34786

  Last Sold Summary

  • 12 Days On Market
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  /42

  $1,499,999

  $30K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,868 Sq Ft

  11015 Hawkshead Ct, Windermere, FL 34786

  Located within the guard gated community of Reserve at Lake Sound in Windermere, this beautifull 5-bedroom, 5-bath residence offers the perfect blend of elegance, comfort, and functionality. Featuring nearly 3,900 square feet of living space, the home showcases tall ceilings, travertine flooring throughout the main living areas, and thoughtful modern updates completed in recent years. A grand

  Julie Davis, LLC COLDWELL BANKER REALTY

  11015 Hawkshead Ct, Windermere, FL 34786
• 

  /2

  $4,475,000

  Sold Mar 25, 2026

  6474 Deacon Cir, Windermere, FL 34786

  • 6 Beds
  • 5.5 Baths
  • 5,853 Sq Ft
  • Built 1989

  Last Sold Summary

  • $765/SF

  Current Estimated Value $4,446,970

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

  6474 Deacon Cir, Windermere, FL 34786
• 

  /2

  Est $502,051

  Not Listed For Sale

  8308 Bryce Canyon Ave, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,065 Sq Ft
  • Built 2016

  8308 Bryce Canyon Ave, Windermere, FL 34786

  Last Sold Summary

  • 4 Days On Market
• 

  

  /66

  $1,895,000

  • 5 Beds
  • 6 Baths
  • 3,728 Sq Ft

  11051 Hawkshead Ct, Windermere, FL 34786

  Discover an exceptional expression of modern luxury in the heart of Windermere. Welcome to 11051 Hawkshead Court, gracefully positioned within the prestigious Reserve at Lake Butler Sound—an exclusive guard-gated enclave renowned for its elegance, privacy, and lakefront lifestyle. Set on an expansive half-acre homesite at the end of a cul-de-sac, this fully reimagined contemporary estate offers a

  Ken Pozek REAL BROKER, LLC

  11051 Hawkshead Ct, Windermere, FL 34786
• 

  /2

  $704,000

  Sold Sep 18, 2025

  1220 Glenheather Dr, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,695 Sq Ft
  • Built 2002

  Last Sold Summary

  • 3% Below List Price
  • $261/SF
  • 22 Days On Market

  Current Estimated Value $716,647

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

  1220 Glenheather Dr, Windermere, FL 34786
• 

  /2

  Est $558,802

  Not Listed For Sale

  8797 Peachtree Park Ct, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft
  • Built 2017

  8797 Peachtree Park Ct, Windermere, FL 34786

  Last Sold Summary

  • 30 Days On Market
• 

  

  /90

  $3,790,000

  $409K PRICE DROP Pending

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

  12132 Montalcino Cir, Windermere, FL 34786

  Experience the essence of luxury lakefront living in this stunning contemporary Mediterranean estate, ideally positioned on Lake Burden within the exclusive gated community of Casa Del Lago in Windermere. This elegant two-story residence combines refined design, functionality, and breathtaking panoramic lake views throughout.The gourmet kitchen features custom dark cabinetry, quartz

  Caroline Perotti BELLA VIEW REALTY LLC

  12132 Montalcino Cir, Windermere, FL 34786
• 

  /2

  $2,460,000

  Sold Dec 18, 2025

  11019 Ullswater Ln, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 5,916 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $416/SF
  • 23 Days On Market

  Current Estimated Value $2,477,566

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  11019 Ullswater Ln, Windermere, FL 34786
• 

  /2

  Est $680,009

  Not Listed For Sale

  9107 Reflection Pointe Dr, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,390 Sq Ft
  • Built 2015

  9107 Reflection Pointe Dr, Windermere, FL 34786

  Last Sold Summary

  • 120 Days On Market
• 

  

  /53

  $4,200,000

  • 4 Beds
  • 5.5 Baths
  • 4,268 Sq Ft

  11809 Lake Butler Blvd, Windermere, FL 34786

  Welcome to 11809 Lake Butler Boulevard, a stunning contemporary estate located in the desirable Lake Butler Estates area of Windermere. Built in 2024 and situated on a 1.05-acre lot, this single-story residence offers 4 bedrooms, 5 full bathrooms, 1 half bathroom, and 4,268 heated square feet with 5,755 total square feet. The home features an elegant open layout, high ceilings, cathedral

  Thiago Nehrer LEGACY PLUS REALTY

  11809 Lake Butler Blvd, Windermere, FL 34786
• 

  /2

  $880,000

  Sold Mar 16, 2026

  11314 Ledgement Ln Unit 1, Windermere, FL 34786

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

  Last Sold Summary

  • 7% Below List Price
  • $286/SF
  • 125 Days On Market

  Current Estimated Value $880,179

  Last Listing Agent Mark Vescio MARK SPAIN REAL ESTATE

  11314 Ledgement Ln Unit 1, Windermere, FL 34786
• 

  /2

  Est $507,881

  Not Listed For Sale

  11555 Charnock Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,886 Sq Ft
  • Built 2018

  11555 Charnock Dr, Windermere, FL 34786

  Last Sold Summary

  • 71 Days On Market
• 

  

  /48

  $714,999

  $35K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,620 Sq Ft

  13842 Orange Crest Dr, Windermere, FL 34786

  PRICED UNDER APPRAISED VALUE! Nestled behind the gated enclave of Eden Isle in Summerport, this stunning five-bedroom, three-bath residence blends modern updates with generous living space. Newly renovated in 2024, the home showcases luxury vinyl plank flooring throughout, a reimagined kitchen, and fully upgraded downstairs bathrooms. Step inside to soaring ceilings and an abundance of natural

  Erica Sadelfeld THE REAL ESTATE COLLECTION LLC

  13842 Orange Crest Dr, Windermere, FL 34786
• 

  /2

  $1,330,000

  Sold Jun 18, 2026

  5825 Oxford Moor Blvd, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 4,319 Sq Ft
  • Built 2002

  Last Sold Summary

  • 11% Below List Price
  • $308/SF
  • 28 Days On Market

  Current Estimated Value $1,478,388

  Last Listing Agent Jeffrey Funk EXP REALTY LLC

  5825 Oxford Moor Blvd, Windermere, FL 34786
• 

  /2

  Est $1,294,308

  Not Listed For Sale

  7587 Lake Albert Dr, Windermere, FL 34786

  • 6 Beds
  • 6.5 Baths
  • 5,149 Sq Ft
  • Built 2014

  7587 Lake Albert Dr, Windermere, FL 34786

  Last Sold Summary

  • 40 Days On Market
• 

  

  /97

  $13,900,000

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

  9832 Laurel Valley Dr, Windermere, FL 34786

  Virtually Staged. A true Lake Butler trophy estate. Set within the world-famous gates of Isleworth and commanding panoramic western sunset water views of Lake Butler from virtually every room, 9832 Laurel Valley Drive offers over 11,000 square feet of luxury lakefront living, situated upon 150 feet of expanded sandy beachfront, thoughtfully enlarged by the current owners, in one of Florida’s most

  Nicholas Taylor REAL BROKER, LLC

  9832 Laurel Valley Dr, Windermere, FL 34786
• 

  /2

  $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 $502,821

  Last Listing Agent Jeffrey Funk EXP REALTY LLC

  12860 Penshurst Ln, Windermere, FL 34786
• 

  /2

  Est $773,364

  Not Listed For Sale

  12971 Westside Village Loop, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 3,694 Sq Ft
  • Built 2018

  12971 Westside Village Loop, Windermere, FL 34786

  Last Sold Summary

  • 72 Days On Market
• 

  

  /70

  $7,250,000

  $345K PRICE DROP

  • 5 Beds
  • 6.5 Baths
  • 7,099 Sq Ft

  5074 Isleworth Country Club Dr, Windermere, FL 34786

  A masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of Isleworth. Completely reimagined and expanded, the residence offers over 7,000 square feet of refined living space, including a 2,400+ square-foot second-story addition designed by acclaimed architect Mark Nasrallah. Situated on over half an acre, the

  Armaan Memarpouri MEM REALTY GROUP

  5074 Isleworth Country Club Dr, Windermere, FL 34786
• 

  /2

  $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 $390,069

  Last Listing Agent Kyle Li UNIONE REALTY INC

  12879 Emersondale Ave, Windermere, FL 34786

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