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... Read More

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Courtesy of Stockworth Realty Group
  • $15,000,000
  • Single Family Home
  • 10
  • 13,519
  • 7
  • 18,877
  • 1998
  • Isleworth
  • O5394385

Poised On A Private Cul-de-sac Overlooking Isleworth’s 14th Fairway And The Beautiful Lake Butler, This Island-inspired Estate Spans Three Home Sites Totaling 1.89 Acres. The Sprawling Floor Plan... Read More

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Courtesy of Isleworth Realty Llc
  • $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... Read More

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Courtesy of Isleworth Realty Llc
  • $8,500,000
  • Single Family Home
  • 9
  • 11,182
  • 6
  • 16,624
  • 2006
  • Isleworth
  • O5441428

Characterized By A Lovely English Garden Designed To Maximize Its Prime Golf-front Location, This Estate Is Unparalleled In Isleworth. Beyond The Circular Driveway With Fountain And Porte-cochere... Read More

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Courtesy of Isleworth Realty Llc
  • $7,499,000
  • Single Family Home
  • 9
  • 10,452
  • 6
  • 13,701
  • 2008
  • Reserve At Lake Butler Sound
  • O5534935

An Elevated Living Experience Awaits In One Of Florida's Most Prominent Locations. Featuring Over 10,000 Sq. Ft. Of Exquisitely Appointed Living Space, Set On Over 2 Privately-gated Acres With... Read More

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Courtesy of Lakeside Realty Windermere Inc
  • $6,195,000
  • Single Family Home
  • 10
  • 12,353
  • 7
  • 16,807
  • 2008
  • Isleworth
  • O5460974

Gracious Living At Its Finest, This Exquisite French Chateau Offers A Prime Location Overlooking The Beautiful Lake Bessie Within The Renowned Isleworth Golf & Country Club. Elegant Finishes,... Read More

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Courtesy of Isleworth Realty Llc
  • $5,895,000
  • Single Family Home
  • 8
  • 11,340
  • 5
  • 19,405
  • 2008
  • Isleworth
  • O5529368

Overlooking The 3rd Green Of Isleworth’s Renowned Championship Golf Course, This Superior Estate Offers Beauty And Sophistication Along The Front Nine. A True Masterpiece, The Home Offers A... Read More

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Courtesy of Isleworth Realty Llc
  • $5,750,000
  • Single Family Home
  • 10
  • 11,100
  • 6
  • 12,796
  • 2004
  • Isleworth
  • O5510614

Unparalleled Isleworth Estate With Amazing Views Of Lake Butler Combined With Direct Golf Course Frontage On Iselworth’s 15th Hole. This One Of A Kind Three Story Home Is Perched High Above The... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $5,450,000
  • Single Family Home
  • 6
  • 8,400
  • 5
  • 11,326
  • 1990
  • Isleworth
  • O5514968

Lakefront Isleworth Estate, Perfectly Located With 400’ On Lake Isleworth Of The Famed Butler Chain In The Isleworth Country Club. From The Moment You Drive Through It’s Charming Entrance And... Read More

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Courtesy of Florida Premier Realty Group
  • $4,495,000
  • 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... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $3,999,000
  • Single Family Use
  • Isleworth
  • Isleworth Amd 03
  • O5466145

Your Opportunity To Build Your Dream Estate On This Beautiful And Unique Piece Of Isleworth Waterfront Land. This Lot Is The Only Piece Of Buildable Land Left In Isleworth That Offers Both Stunning... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $3,995,900
  • Single Family Home
  • 9
  • 10,701
  • 6
  • 15,612
  • 2008
  • Isleworth
  • O5519584

Captivating European-style Custom Estate Is Ideally Sited On A Corner Home Site In Isleworth Country Club. This Modern Transitional Style Home Combines The Finest Materials And Finishes Equating To A... Read More

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Courtesy of Premier Realty Partners Inc
  • $3,900,000
  • Single Family Home
  • 9
  • 9,594
  • 7
  • 14,190
  • 2008
  • 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... Read More

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Courtesy of Julian Properties, Inc.
  • $3,895,000
  • 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... Read More

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Courtesy of Bhhs Results Realty
  • $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... Read More

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Courtesy of Florida Connexion Properties
  • $3,695,000
  • Single Family Home
  • 6
  • 7,884
  • 5
  • 9,697
  • 2001
  • Keenes Pointe
  • O5543733

Below Appraisal! Now Is The Opportunity To Own This Magnificent Lakefront French Country Estate On Lake Tibet, Part Of The Pristine Butler Chain Of 11 Lakes. Spanning A Total Of Over 9600 Sf, This... Read More

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Courtesy of Exp Realty Llc
  • $3,680,000
  • Single Family Home
  • 10
  • 8,305
  • 6
  • 12,557
  • 2011
  • Keenes Pointe Un 10
  • O5538904

This Renowned Home Is Located In Keene's Pointe. The Home Comes Fully Furnished With The Best There Is To Offer In High End Fixtures And Finishes. The Interior Features 6 Bedrooms, A Theater, A Large... Read More

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

Magnificent French Country Estate 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... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $3,489,000
  • Single Family Home
  • 6
  • 6,584
  • 5
  • 9,624
  • 2006
  • Isleworth
  • O5459984

This Beautiful Mediterranean Estate Offers You The Best Of The Best In Isleworth. From The Olde World Stucco To The Precast Sills, Columns And The Perfectly Manicured Mature Landscaping, To Being On... Read More

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Courtesy of Premier Realty Partners Inc
  • $3,475,000
  • Single Family Home
  • 9
  • 7,506
  • 5
  • 11,467
  • 2004
  • Reserve At Lake Butler Sound
  • O5530985

Perfectly Sited On Lake Butler With Over An Acre Of Land In Renowned Lake Butler Sound. This Jones Clayton Custom Estate Presents Classic European Elegance. The Olde World Brick Motor Court Leads To... Read More

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Courtesy of Premier Realty Partners Inc
  • $3,450,000
  • Single Family Home
  • 7
  • 7,329
  • 5
  • 2010
  • Keenes Pointe Un 10
  • O5493488

Exquisite Custom Lakefront Home Located In Highly Desired Keene's Pointe. As You Enter This Traditional Home You Are Greeted By The Two-story Foyer And Grand Staircase. This Home Boasts Over 7,300 Sf... Read More

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Courtesy of Southern Realty Group Llc
  • $3,450,000
  • Single Family Home
  • 7
  • 6,972
  • 6
  • 10,069
  • 2004
  • Reserve At Lake Butler Sound 45/120
  • S4850628

Vita Del Lago Rests On 1.3 Acres Of Land, With Breathtaking Views Of Gorgeous Lake Butler. You Arrive At The Front Of The Home Via Its Welcoming Circular Driveway. Upon Entry Is A Grand Staircase And... Read More

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Courtesy of Nectar Real Estate
  • $3,300,000
  • 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... Read More

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Courtesy of Masters Realty Group Inc
  • $3,250,000
  • 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... Read More

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Courtesy of Isleworth Realty Llc
  • $3,200,000
  • Single Family Home
  • 5
  • 6,598
  • 3
  • 9,474
  • 2016
  • Isleworth
  • O5503720

New: Lived In For Less Than 1 Month! Nestled Within The Gates Of The Renowned Isleworth Golf & Country Club, This Two-story Estate Offers Exquisite Appeal Through The More Than 6,500-square-foot... Read More

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Courtesy of Isleworth Realty Llc
  • $3,195,000
  • 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... Read More

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Courtesy of Isleworth Realty Llc
  • $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... Read More

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Courtesy of Premium Properties R.e. Service
  • $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;... Read More

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Courtesy of Premier Realty Partners Inc
  • $2,995,000
  • Single Family Home
  • 8
  • 7,177
  • 6
  • 8,877
  • 2007
  • Aladar Rep
  • O5525009

Priced To Sell! Welcome To 2nd Avenue, Downtown Windermere’s Most Sought After Address. Gracefully Adorned By The Peace And Tranquility Of Wauseon Bay, This French Provincial Custom Built Home... Read More

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Courtesy of Stockworth Realty Group
  • $2,850,000
  • Single Family Home
  • 8
  • 5,480
  • 4
  • 8,202
  • 2006
  • Isleworth
  • O5464890

This Exquisite Custom Residence Boasts The Finest High Quality Finishes Throughout, From The Handsome Wood & Travertine Floors To The Venetian Plaster Walls & The Many Ceiling Details Which Raise... Read More

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Courtesy of Bhhs Florida Realty

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