Windermere Florida Homes & Condos For Sale

Nestled between Lake Butler, Lake Down and Lake Bessie is the town of Windermere, a charming suburban destination blessed with incredible weather and unbeatable outdoor recreation opportunities.

If you love water sports, boating or fishing, but you still want to have quick access to a big city, then Windermere is a fantastic place to call home.

The Facts About Windermere, Florida

Windermere is a town with a population of just 2,800. The entire town is just 1.5 square miles in total, making it a relatively small area. While it was first settled toward the end of the 19th century, Windermere received its town charter in 1925.

Windermere enjoys a reputation as an appealing and upscale destination thanks to its staggering amount of waterfront property as well as its high-end homes. Median income in Windermere is very high for the state as a whole, as is the per capita income.

Windermere and the Local School System

OCPS, or the Orange County Public Schools, is the school system that oversees public education in Windermere. The youngest residents of Windermere, should they attend public schools, will start at either Windermere Elementary School or Sunset Park Elementary School.

The local public middle school is Gotha Middle School. Students attending Orange County Public High Schools will be bused to nearby campuses depending on their address as well as their academic needs.

Windermere is also home to a highly ranked K-12 private preparatory school favored by many residents.

What You'll Love About Windermere

There is no question that a major draw to the Windermere area is the abundance of lakes. These lakes are literally steps from home for many Windermere residents, making it easy to get out and enjoy the exceptional climate of the region.

Windermere is also a very safe community with low crime rates. This gives people peace of mind whether they are jogging after work or allowing their children to ride their bike to a friend's house.

While Windermere is of course a desirable place to live, it would be a mistake to forget about its neighbor: Orlando. Windermere is only 14 miles from the heart of Downtown Orlando, and a similar distance to the Orlando International Airport and major theme parks like Disney World.

Whether you're a frequent business traveler or a parent with children, you'll definitely appreciate Windermere's proximity to so many great attractions and amenities.

Windermere, Florida, offers what can be accurately described as the best of two worlds. Safe, small and community-oriented, Windermere is a fantastic place to raise a family or live a quiet, peaceful life.

However, the bustling city of Orlando offers sporting events, theme parks, business opportunities, shopping malls and world-famous dining and nightlife, and it is all just minutes away from the homes and residents of Windermere.

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Properties For SaleSold Properties
  • $18,950,000
  • Single Family Home
  • 17
  • 20,240
  • 9
  • 30,949
  • 2010
  • O5498420

Presenting Central Florida’s Most Exquisite Lake Butler Estate Tucked Behind The Secured Manned Gates Of Lake Butler Sound. Offering 20,240 Sq Ft Under Air (31,000 Gross), On Nearly 5 Acres And 547 Feet Of Lake Frontage, This Double-lot Oasis Offers A Magnificent Residence With Multiple Outdoor Living And Entertaining Areas, Private Guest Quarters, 8-car Garage, Lighted Tennis Court With... Read More

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Courtesy of Stockworth Realty Group
  • $10,999,000
  • Single Family Home
  • 11
  • 15,063
  • 7
  • 23,685
  • 2015
  • Isleworth
  • O5433535

A Sprawling Floor Plan And A Prime Setting On 3.76 Acres Along The Shores Of Lake Bessie Define This Exquisite Seven-bedroom Residence. Through A Pair Of Arched French Doors With Glass And Iron Detail, The Foyer Opens To A Stunning Two-story Living Room Where Dramatic Floor-to Ceiling Windows Allow An Abundance Of Natural Light While Capturing The Stunning Water Views. A Wealth Of Unique Finishes... Read More

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Courtesy of Isleworth Realty Llc
  • $7,950,000
  • Single Family Home
  • 10
  • 10,730
  • 7
  • 14,166
  • 2018
  • Isleworth
  • O5565384

Rare Opportunity To Own A 2018 Custom Phil Kean Built Stunning Estate Located In World-renowned Isleworth Country Club Perfectly Sited On Pristine Lake Blanche Of The Coveted Butler Chain Of Lakes. This Grand Estate Makes A Spectacular First Impression With Sweeping Picturesque Lake Views From Every Angle & 22ft Coffered Ceilings Adorned With Two Exquisite Chandeliers, A Gas Fireplace With Custom... Read More

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Courtesy of Infinity Realty Group Llc
  • $6,650,000
  • Single Family Home
  • 9
  • 8,049
  • 6
  • 11,679
  • 1992
  • Isleworth
  • O5573526

Nestled Along The Shores Of Lake Butler In The Renowned Isleworth Golf & Country Club, This Fabulous Estate Strikes The Perfect Balance Between Modernity And Sophistication. Offering Superb Living Spaces In A Lakefront Setting, The Estate Boasts A Beautifully Updated Interior Totaling More Than 8,000 Square Feet. Stunning Mahogany French Doors And A Smooth Marble Floating Staircase In The Grand... Read More

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Courtesy of Isleworth Realty Llc
  • $5,495,000
  • Single Family Home
  • 8
  • 8,802
  • 5
  • 11,073
  • 2017
  • Isleworth
  • O5547156

Under Construction. Designed By Renowned Architect Terry Irwin And Currently Being Built By Leading Custom Homebuilder Wyatt Construction, This Two-story Estate Will Offer Five Bedrooms And More Than 8,800 Square Feet Of Living Space. Nestled Along The Back Nine Within The Gates Of The Renowned Isleworth Golf & Country Club, The Estate Will Afford Beautiful Finishes And Living Spaces Set Against... Read More

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Courtesy of Isleworth Realty Llc
  • $5,395,000
  • Single Family Home
  • 7
  • 8,162
  • 5
  • 10,097
  • 2017
  • Isleworth
  • O5547144

New Construction, Just Completed. Offering A Prime Location Within The Gates Of The Renowned Isleworth Golf & Country Club, This Two-story Estate Features Magnificent Views Of Holes 11 And 12, As Well As Eagle Pond And Open Land Showcasing One Of Isleworth’s Exquisite Sculptures. Designed By Renowned Architect Terry Irwin And Built By Leading Custom Homebuilder Wyatt Construction, The... Read More

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Courtesy of Isleworth Realty Llc
  • $5,295,000
  • Single Family Home
  • 8
  • 10,394
  • 5
  • 14,582
  • 2006
  • Isleworth
  • O5559035

Experience One Of Isleworth’s Most Exquisite Estates, Inspired By An Italian Villa In Bellagio, Italy, And Its Namesake, “bellagio” By Southpoint Homes. With A Fabulous Location Along The Front Nine Of Isleworth’s Renowned Championship Golf Course Overlooking The Hole 3 Fairway, The Expansive Home Showcases More Than 10,300 Square Feet Of Living Space, Revealing Hand-painted Finishes,... Read More

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Courtesy of Isleworth Realty Llc
  • $4,999,000
  • Single Family Home
  • 6
  • 8,400
  • 5
  • 11,326
  • 1990
  • Isleworth
  • O5571293

Offering Breathtaking Views Of Beautiful Lake Isleworth, The Splendido Estate In The Renowned Isleworth Golf & Country Club Delivers Beautiful Sunsets And An Italian-inspired Interior Totaling 8,400 Square Feet. Set On A Cul-de-sac With 360 Feet Of Lake Frontage, The Sprawling Estate Boasts Countless Artistic Finishes And Luxurious Living Spaces Against A Backdrop Of Water Vistas. A Private Gate... Read More

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Courtesy of Isleworth Realty Llc
  • $4,200,000
  • Single Family Use
  • Lake Down Estates
  • O5556718

Extraordinary Opportunity To Acquire Over 10+/- Acres With 500+/- Of Frontage On Lake Down On The Prestigious Butler Chain Of Lakes. Rare To See Such A Beautiful Lakefront Parcel On The Butler Chain Of Lakes One Of Florida's First-class Waterways Of 11 Interconnecting Lakes & 72 Miles Of Shoreline. The Parcel Has The Opportunity To Be Divided Into A Minor Lot Split For 4 Lots Or Your Private... Read More

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Courtesy of Premier Realty Partners Inc
  • $3,995,000
  • Single Family Home
  • 8
  • 8,051
  • 5
  • 11,899
  • 1996
  • Replat Of Metcalf Park
  • O5504189

Quite Possibly The Most Serene & Luxurious Retreat On The Butler Chain Of Lakes. Few Homes Compare To Having Approximately 550 Feet Of Shoreline On Lake Butler, 8000+ Square Feet Of Low-country Style Living Space, And A Place To Park Your Sea Plane! Exquisite Lake Views Are Just The Beginning Of This Impeccably Appointed Estate Home. As You Enter The Grounds Of This 2+ Acre Property You Are... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $3,875,000
  • Single Family Home
  • 6
  • 7,073
  • 5
  • 9,166
  • 2001
  • Isleworth
  • O5563361

Nestled Along The Shores Of Beautiful Lake Louise With Direct Access To The Butler Chain Of Lakes, This Elegant Isleworth West Estate Built By Southpoint Homes Encompasses More Than 7,000 Square Feet Of Living Space. Dramatic Lake Views Extending Beyond The Lovely Pool And Private Dock Are Revealed Upon Entry, From Exquisite Custom Doors That Open To The Foyer And Formal Living Room With... Read More

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Courtesy of Isleworth Realty Llc
  • $3,800,000
  • Single Family Home
  • 8
  • 6,325
  • 6
  • 8,898
  • 2003
  • Isleworth 01 Amd
  • O5544457

Paradise! This Stunning And Peaceful Isleworth Estate Has It All. Located On A Quiet Cul-de-sac That Offers Breathtaking Views Of Hourglass Pond From All Main Rooms. As You Step Into The Living Room Your Eyes Are Drawn To The Dazzling Views Of The Water And Golf Course. Six Spacious Bedroom Suites And A Half Bath. Perfect For Entertaining! Outdoor Areas Equipped With An Outstanding Summer... Read More

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Courtesy of Florida Connexion Properties
  • $3,800,000
  • Single Family Home
  • 9
  • 9,594
  • 7
  • 14,190
  • 2008
  • Reserve At Lake Butler Sound
  • O5458415

Lake Butler Chain Of Lakes Estate Home. Fully Furnished, Lake Front, Two Story Home Is Located In The Guard Gated Community Of "the Reserve At Butler Sound" Providing Over 9,000 Sf Of Lake Front Luxury Living. Custom Stone Flooring Crafted Woodwork, Sunken Wine Vault, Formal Dining Room, Formal Office The Master Suite Is Complete With Gas Fireplace, Huge His/her Walk-in Closets, Elegant Spa... Read More

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Courtesy of Julian Properties, Inc.
  • $3,795,000
  • Single Family Home
  • 7
  • 7,607
  • 5
  • 10,961
  • 2004
  • Keenes Pointe Unit 01
  • O5522180

Price Adjustment. This Lakefront Estate Has Luxury That Abounds From The Moment Your Eyes Meet With An Unproceeded Location On The Butler Chain Of Lakes In Keene's Pointe. Upon Entering The Stunning Foyer And The Cavernous Dining + Living Rooms, You'll Partake In Picturesque Views Of Lake Tibet Butler. Impeccably Designed Attention To Every Detail The Kitchen Is A Chef's Entertainment Dream... Read More

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Courtesy of Bhhs Results Realty
  • $3,600,000
  • Single Family Use
  • Rosser Reserve
  • O5566804

Butler Chain Of Lakes Home Site With Truly Custom Estate Starting At $3,500,000.00. Only 1 Preferred Builder That Can Bring Any Plan You Have To Life! Discover The Luxury And Exclusivity Of This Intimate Community! Perfectly Nestled On The Butler Chain Of Lakes And Conveniently Located Across From Isleworth Golf & Country Club Lies The New Green Isle Formerly The Rosser Reserve. This Gorgeous... Read More

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Courtesy of Engel & Volkers Clermont
  • $3,600,000
  • Single Family Use
  • Rosser Reserve
  • O5566814

Butler Chain Of Lakes Waterfront Home Site With Truly Custom Estate Starting At $3,600,000.00. Only 1 Preferred Builder That Can Bring Any Plan You Have To Life! Discover The Luxury And Exclusivity Of This Intimate Community! Perfectly Nestled On The Butler Chain Of Lakes And Conveniently Located Across From Isleworth Golf & Country Club Lies The New Green Isle Formerly The Rosser Reserve. This... Read More

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Courtesy of Engel & Volkers Clermont
  • $3,499,000
  • Single Family Home
  • 7
  • 7,187
  • 5
  • 10,185
  • 2012
  • Keenes Pointe Unit 10
  • O5569153

Transitional Design And The Ultimate In Florida Lakefront Luxury Living Awaits You At This Butler Chain Waterfront Estate That Sits On Just Over An Acre. Wake Up Each Morning To Spectacular Views In The Well-appointed Master Suite Equal To That Of A 5-star Resort. Your Family And Guests Will Enjoy Luxury As Well In The Other 4 Generously Proportioned Ensuite Bedrooms. Formal Living And Dining... Read More

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Courtesy of Stockworth Realty Group
  • $3,495,000
  • Single Family Home
  • 8
  • 7,159
  • 6
  • 10,074
  • 1999
  • Isleworth
  • O5502452

Magnificent Estate With Elegant Interiors & Sun-filled Grounds Offers Florida Resort Luxury Lifestyle All Year Round. Situated In Hole 6 Of The World-renowned Isleworth Country Club Golf Course. This Golf Front Estate Features 7,159 Sq Ft With Six Bedrooms, Seven Full & One Half Baths. An Inviting Guest House With Private Entrance Provides Visitors With All The Comforts Of Home. Newly Remodeled... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $3,299,000
  • Single Family Home
  • 6
  • 7,329
  • 5
  • 11,034
  • 2010
  • Keenses Pointe
  • O5572950

Stunning Butler Chain Home Located In The 24 Hour Guard Gated Community Of Keene’s Pointe. As You Step Through The Front Doors Your Immediately Greeted By The Soaring Ceilings Of A Grand Two-story Foyer With Amazing Lake Views In The Distance. The Chef In The Family Is Sure To Love The Massive Kitchen With Two Center Islands, A Walk-in Pantry, & Top Of The Line Appliances Including An Oversized... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $3,295,000
  • Single Family Home
  • 6
  • 6,756
  • 5
  • 8,749
  • 2004
  • Reserve At Lake Butler Sound 45/120
  • O5562977

Sited On One Acre This Custom Lakefront Estate Exudes A Spirit Of Elegance Derived From Its Southern California Architectural Influences. Located In Guard Gated Lake Butler Sound And Boasting Unobstructed Views Of Lake Butler, Of The Famed Butler Chain Of Lakes, This Stunning Plan Is Perfect For Family Living And Entertaining. The Arched Solid Wood Door Creates A Refined Entry While A Series Of... Read More

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Courtesy of Premier Realty Partners Inc
  • $3,295,000
  • Single Family Home
  • 6
  • 7,768
  • 5
  • 10,339
  • 1999
  • Keenes Pointe
  • O5552112

Luxury Abounds In This Extraordinary Lakefront Estate On The Butler Chain Of Lakes In Keene's Pointe. Beyond, The Circular Driveway With Fountain & Porte-cochere Entry, A Pair Of French Doors Open To The Stunning 2 Story Living Room, With Natural Light While Capturing The Lake Views & Stone Fireplace. The Main Floor Features A Master Bedroom With Venetian Plaster, 2 Walk-in Closets, Wet Bar &... Read More

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Courtesy of Bhhs Results Realty
  • $3,150,000
  • Single Family Home
  • 6
  • 6,605
  • 4
  • 8,594
  • 1990
  • Isleworth
  • O5534572

Welcome To This Gorgeous Lake Front Home! Lake Views Compliment This Spectacular Isleworth Home That Has A Completely Redesigned 2nd Floor With World Class Finishes. As You Step Through The Front Entrance, You Are Led To A Grand Living Area With Floor To Ceiling Windows Filling The Space With Natural Light And Giving You An Amazing View Of The Lake. The Spacious Kitchen Features Stainless Steel... Read More

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Courtesy of Premium Properties R.e. Service
  • $3,150,000
  • Single Family Home
  • 6
  • 7,208
  • 5
  • 9,740
  • 2006
  • Aladar On Lake Butler
  • O5522373

Spectacular Custom Built Lake Butler Front Trophy Home That Was Designed For Entertaining And Living The Windermere "lake Life". Nasrallah Architects Created This Masterpiece To Focus Around The Infinity Edge Pool And The Unrivaled Lake Butler Views. Imported Italian Travertine Throughout The First Floor. Sliding Pocket Doors Disappear Into The House To Bring The Outdoors In, Giving Unobstructed... Read More

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Courtesy of Masters Realty International Llc
  • $3,100,000
  • Single Family Home
  • 5
  • 5,752
  • 4
  • 7,772
  • 2002
  • Isleworth West
  • O5562746

Enjoy The Unparalleled Amenities Of This Beautiful 4 Br 4.1 Ba Mediterranean Home Spanning 5,752 Sf Located In The Most Coveted Neighborhood Of Isleworth. Area Surrounding Lake Has Been Cleared To Appreciate Unobstructed, Picturesque Views Of Lake Louise On Butler Chain Of Lakes, Considered One Of Central Florida’s Most Sought-after Lakefront Properties, From Your Living Room Or Second Story... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $2,995,000
  • Single Family Use
  • O5567644

Spectacular Sweeping Lakefront Vistas. A Unique Opportunity To Own 2+ Acres High And Dry With Over 170 Feet Of Frontage On Lake Butler Of The Famed Butler Chain Of Lakes With 11 Interconnecting Lakes And 72 Miles Of Shoreline. This Unique Property Has A Private Gated Drive Featuring Gorgeous Mature Oak Trees. Enjoy The Current Completely Updated And Chic Residence, Build Your Dream Home Or... Read More

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Courtesy of Premier Realty Partners Inc
  • $2,995,000
  • Single Family Home
  • 7
  • 6,477
  • 5
  • 9,501
  • 1998
  • Isleworth 01 Amd
  • O5498318

This Home Exudes A Spirit Of Elegance Derived From Its European Architectural Influences. Located In The Renowned Community Of Isleworth This Stunning Custom Home Is Highly Stylish Yet Comfortable; Perfect For Family Living And Entertaining. The Arched Solid Wood Custom Made Double Doors Create A Refined Entry. The Formal Living And Dining Rooms Are Brightened By Arched Clerestory Windows And... Read More

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Courtesy of Premier Realty Partners Inc
  • $2,995,000
  • Single Family Home
  • 4
  • 3,832
  • 3
  • 7,051
  • 2007
  • O5531748

Positioned Along The Shores Of Lake Chase Across From Isleworth’s Renowned Clubhouse And Next To Hole 9, This Exquisite Home Sets The Standard For Exceptional Architecture, Quality Finishes And Prime Setting. Built By Pellegrini Custom Homes With Interiors By Renowned Palm Beach Gardens Designer Hilda Flack, The Estate Is One Of Only A Handful To Feature Both Golf Course And Lake Frontage. Its... Read More

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Courtesy of Isleworth Realty Llc
  • $2,995,000
  • Single Family Home
  • 3
  • 2,193
  • 3
  • 2,648
  • 2014
  • Kelso Area
  • O5567534

Spectacular Sweeping Lakefront Vistas. A Unique Opportunity To Own 2+ Acres High And Dry With Over 170 Feet Of Frontage On Lake Butler Of The Famed Butler Chain Of Lakes With 11 Interconnecting Lakes And 72 Miles Of Shoreline. This Unique Property Has A Private Gated Drive Featuring Gorgeous Mature Oak Trees. Enjoy The Current Completely Updated And Chic Residence, Build Your Dream Home Or... Read More

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Courtesy of Premier Realty Partners Inc
  • $2,950,000
  • Single Family Home
  • 4
  • 4,644
  • 4
  • 5,647
  • 1991
  • Isleworth
  • O5532675

A Stunning Lakefront Setting Characterizes This Lovely Four-bedroom Estate Nestled Along The Shores Of Beautiful Lake Louise In The Renowned Isleworth Golf & Country Club. The Single-story Home Offers A Sprawling Floor Plan Encompassing More Than 4,600 Square Feet Of Living Space Surrounding An Open-air, Infinity-edge Swimming Pool Overlooking The Water. Floor-to-ceiling Windows Line The Back Of... Read More

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Courtesy of Isleworth Realty Llc
  • $2,950,000
  • Single Family Home
  • 11
  • 9,376
  • 7
  • 11,940
  • 2008
  • Reserve At Lake Butler Sound 45/120
  • O5570989

Exclusivity And Privacy Await In This One-of-a-kind Custom Estate On The Shores Of Lake Butler. Nestled In The Heart Of Guard-gated Reserve At Lake Butler Sound, This 7 Bedroom/11 Bathroom Residence Exudes Quality Finishes At Every Turn. Every Detail Is Exquisite: From The Pine Antiqued Barn Wood Floors To The Dark Beamed Soaring Ceilings To The Rustic Masonry Throughout It's 9,376 Square Feet Of... Read More

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Courtesy of Lakeside Realty Windermere Inc

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