Windermere, FL Homes

• 

  

  

  /6

  $525,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,926 Sq Ft

  6679 Duncaster St, Windermere, FL 34786

  Welcome to this beautiful maintained traditional-style home in the highly desirable Town of Windermere, Florida, just minutes from the renewed Butler-Chain of Lakes. Nestled in a quiet, peaceful neighborhood, this 3-bedroom, 2-bathroom home offers 1,926 square feet of comfortable living space with thoughtful upgrades throughout.The updated kitchen features renovated cabinetry, while both

  Cliff Glansen FLATFEE.COM

  6679 Duncaster St, Windermere, FL 34786
• 

  

  /2

  $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
• 

  

  /2

  Est $490,306

  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

  Last Listing Agent Juan Castro REDFIN CORPORATION
• 

  

  

  /43

  $629,900

  $10K PRICE DROP Under Contract

  • 4 Beds
  • 3 Baths
  • 2,648 Sq Ft

  13328 Overstreet Rd, Windermere, FL 34786

  Under contract-accepting backup offers. Situated on a distinguished homesite in one of Windermere's most sought after locations, 13328 Overstreet Road impresses right when you pull into the oversized 6+ CAR PAVER DRIVWAY with parking for up to six vehicles. If any of those vehicles are electric, you can charge them using the installed TESLA CAR CHARGER and save $$ on the electric bill with the

  Carmen Aridas RE/MAX PRIME PROPERTIES

  13328 Overstreet Rd, 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 $321,941

  Last Listing Agent Kyle Li UNIONE REALTY INC

  12879 Emersondale Ave, Windermere, FL 34786
• 

  /2

  Est $508,288

  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

  Last Listing Agent Troy Hensley BHHS FLORIDA REALTY
• 

  

  /53

  $870,000

  • 4 Beds
  • 3 Baths
  • 3,746 Sq Ft

  9043 Horizon Pointe Trail, Windermere, FL 34786

  Windermere Custom Interior Pool Home, 4 bedroom, 2 Primary Suites, 3 full Bathrooms New Exterior and Interior paint 2026, New Hardwood Bamboo Floors 2025, Crown Molding, Coffered Ceilings. New Heated Salt Water Pool, New Air Conditioner 2025, New Hot Water Heater 2025, Gourmet Kitchen with Hand Cut European Backsplash, Butler Pantry and Walk In Pantry, New Dishwasher 2024. Remodeled Master Shower

  Matine Pawlicki CENTURY 21 CARIOTI

  9043 Horizon Pointe Trail, Windermere, FL 34786
• 

  /2

  $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
• 

  /2

  Est $487,878

  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

  Last Listing Agent Mulcy Tenorio FLORIDA CONNEXION PROPERTIES
• 

  

  /9

  $5,995,000

  New Construction

  • 5 Beds
  • 6 Baths
  • 6,000 Sq Ft

  13377 Lake Butler Blvd, Winter Garden, FL 34787

  Pre-Construction. To be built. To be Built, Rendering provided by master custom home builder, David Konkol of Konkol Custom Homes. However, buyer can work with builder to build any design buyer prefers (pricing to adjust accordingly). The property is spectacular waterfront acreage with boat dock on boatable, skiable Lake Roper. Acreage is 12.4 +/- with some conservation. Zoned A-1 (agricultural

  Dawn Briggs BLUE MAGNOLIA REALTY LLC

  13377 Lake Butler Blvd, Winter Garden, FL 34787
• 

  /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
• 

  

  /30

  Est $673,617

  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

  Last Listing Agent Chris Creegan CREEGAN GROUP
• 

  

  /100

  $1,595,000

  • 4 Beds
  • 3.5 Baths
  • 3,166 Sq Ft

  12417 Montalcino Cir, Windermere, FL 34786

  Welcome to this impeccably designed, all-on-one-floor luxury custom home located in one of the most sought-after gated communities of Windermere, Casa Del Lago, where timeless Mediterranean architecture meets refined Florida living.This exceptional home offers four bedrooms and four full bathrooms and is thoughtfully designed with custom details, designer features, modern décor, graceful

  Aziz Elbrak LA ROSA REALTY LLC

  12417 Montalcino Cir, Windermere, FL 34786
• 

  /2

  $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
• 

  

  /33

  Est $509,894

  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

  Last Listing Agent Thad Czapka COLDWELL BANKER REALTY
• 

  

  /32

  $330,000

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft

  11446 Jasper Kay Terrace Unit 103, Windermere, FL 34786

  Welcome to 11446 Jasper Kay Terrace, Unit 103, a beautifully updated first-floor condominium offering comfortable, low-maintenance living in a gated Windermere community. This move-in ready residence features a desirable split-bedroom floor plan with three bedrooms and two bathrooms, providing both privacy and functionality.The open-concept layout seamlessly connects the kitchen, dining, and

  Jay Stewart SOUTHERN REALTY GROUP LLC

  11446 Jasper Kay Terrace Unit 103, Windermere, FL 34786
• 

  /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
• 

  /2

  Est $1,425,139

  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

  Last Listing Agent John Cunningham KELLER WILLIAMS CLASSIC
• 

  

  /75

  $999,000

  $51K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 4,507 Sq Ft

  8701 Iron Mountain Trail, Windermere, FL 34786

  Flexible living takes center stage in this 4,563-square-foot Windermere Trails home, where six bedrooms, four-and-a-half baths, multiple gathering spaces, and a substantial screened outdoor area create room for everyday life to unfold comfortably. The kitchen anchors the main living area with white cabinetry, a tiled backsplash, stainless-finish appliances, double wall ovens, and a large island

  Jorge Martinez, Jr KELLER WILLIAMS CLASSIC

  8701 Iron Mountain Trail, Windermere, FL 34786
• 

  /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
• 

  /2

  Est $508,885

  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

  Last Listing Agent Pilar Fernandez SIX STAR REALTY GROUP LLC
• 

  

  /68

  $15,500,000

  • 10 Beds
  • 17 Baths
  • 13,425 Sq Ft

  12488 Park Ave, Windermere, FL 34786

  Commanding a rare 2.75-acre lakefront setting on the coveted Butler Chain of Lakes, this extraordinary Windermere estate is a true work of art. Recently completed after a meticulous, ground-up transformation, the residence showcases a level of craftsmanship, design integrity, and finish quality that is simply unrivaled in Central Florida. From the moment you arrive, the estate announces itself

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  12488 Park Ave, Windermere, FL 34786
• 

  /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
• 

  /2

  Est $534,443

  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

  Last Listing Agent Cliff Glansen FLATFEE.COM
• 

  

  /55

  $1,599,000

  Pending

  • 4 Beds
  • 4 Baths
  • 4,206 Sq Ft

  2113 Water Key Dr, Windermere, FL 34786

  Set along the shores of Lake Roberts within guard-gated Waterford Pointe, this four-bedroom, four-bath lakefront residence offers a rare opportunity to enjoy the quintessential Windermere waterfront lifestyle. With a private covered boat dock and direct access to the ski lake, the home is designed around both the water and effortless indoor-outdoor living. Inside, an expansive floor plan features

  Steve Healy CORCORAN PREMIER REALTY

  2113 Water Key Dr, Windermere, FL 34786
• 

  /2

  $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
• 

  /2

  Est $656,143

  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

  Last Listing Agent Rodolfo Renwick WEALTHY REALTY, LLC
• 

  

  /31

  $795,000

  $80K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,124 Sq Ft

  5413 Walsh Pond Ct, Windermere, FL 34786

  Discover the charm of this water front, 4 bedroom 3.5 bath home located in the desirable Summerport community. This unique property is nestled in the cul de sac for complete privacy. Enjoy scenic water views while relaxing poolside on the spacious screen enclosed lanai, which is also great for entertaining. The interior features granite countertops, stainless appliances, 42" cabinets, built in

  Brenda Jebailey HAVEN PROPERTY GROUP LLC

  5413 Walsh Pond Ct, Windermere, FL 34786
• 

  /2

  $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
• 

  /2

  Est $1,399,098

  Not Listed For Sale

  7443 Lake Albert Dr, Windermere, FL 34786

  • 6 Beds
  • 6.5 Baths
  • 5,095 Sq Ft
  • Built 2014

  7443 Lake Albert Dr, Windermere, FL 34786

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Cliff Glansen FLATFEE.COM
• 

  

  /21

  $575,000

  • 4 Beds
  • 3 Baths
  • 2,064 Sq Ft

  6828 Helmsley Cir, Windermere, FL 34786

  Welcome to this beautifully fully renovated Windermere home, where every room has been thoughtfully updated to create a fresh, modern, move-in-ready living experience. Located in the desirable Preston Square community, this 4-bedroom, 3-bath home offers a convenient location near Sunset Park Elementary, Horizon West Middle and Windermere High, along with easy access to shopping, dining,

  Abdallah Fawaz LPT REALTY, LLC

  6828 Helmsley Cir, Windermere, FL 34786
• 

  /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
• 

  /2

  Est $775,270

  Not Listed For Sale

  12880 Westside Village Loop, Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,769 Sq Ft
  • Built 2018

  12880 Westside Village Loop, Windermere, FL 34786

  Last Sold Summary

  • 118 Days On Market

  Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC
• 

  /2

  $3,750,000

  New Construction

  • 5 Beds
  • 5.5 Baths
  • 6,182 Sq Ft

  9960 6th St, Windermere, FL 34786

  Under Construction. Experience unparalleled luxury in this custom-built Davila Homes estate, ideally located in the heart of Windermere. Showcasing the highly sought-after Stanford floor plan, this magnificent residence offers approximately 6,182 square feet of living space with 5 bedrooms, 5 full baths, 1 half bath, and a spacious 3-car garage. Designed for both elegant entertaining and

  Fernanda Negromonte NOVA REAL ESTATE SERVICES INC

  9960 6th St, Windermere, FL 34786
• 

  /2

  $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 $879,674

  Last Listing Agent Matthew Hughes CHARLES RUTENBERG REALTY ORLANDO

  4 Chase Rd, Windermere, FL 34786
• 

  /2

  Est $494,352

  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

  Last Listing Agent Jeffrey Stocks STOCKS FAMILY REALTY LLC
• 

  

  /30

  $635,000

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft

  9110 Palm Tree Dr, Windermere, FL 34786

  Welcome home. This wonderfully kept move-in ready 3 bedroom, 2 bathroom pool home is located in one of SouthWest Orlando's sought after communities, Silver Woods. It features travertine tile flooring throughout most of the home with engineered hardwood flooring in all the bedrooms, an open kitchen with stainless steel appliances and granite countertops overlooking the family room and an inside

  Tony Vicari VICARI REALTY CORP

  9110 Palm Tree Dr, Windermere, FL 34786
• 

  /2

  $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
• 

  /2

  Est $1,272,021

  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

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC
• 

  

  /10

  $879,000

  $71K PRICE DROP

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

  13542 Gorgona Isle Dr, Windermere, FL 34786

  Virtually Staged. Lake View Home with Private Pool & Fireworks Views – Minutes from Walt Disney World Imagine living in a home that perfectly combines comfort, elegance, and practicality in one of the most desirable areas of Windermere. This beautiful residence offers stunning lake views and magical nightly fireworks views from Walt Disney World, creating a truly unique living experience. From

  Thiago Ataide WRA BUSINESS & REAL ESTATE

  13542 Gorgona Isle Dr, Windermere, FL 34786

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