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
  • $6,875,000
  • 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
  • $6,645,000
  • Single Family Home
  • 9
  • 11,163
  • 6
  • 14,474
  • 2011
  • O5431648

Seller Requirement: Buyer Must Produce Proof Of Funds At Full Listing Price. This Commanding Waterfront Residence Is Elegantly Situated On A Picturesque Home Site Along The Shores Of Beautiful Lake... Read More

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Courtesy of Isleworth Realty Llc
  • $5,795,000
  • Single Family Home
  • 8
  • 8,802
  • 5
  • 11,073
  • 2017
  • Isleworth
  • O5469566

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... 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
  • $5,650,000
  • 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
  • $5,495,000
  • Single Family Home
  • 7
  • 8,162
  • 5
  • 10,097
  • 2017
  • Isleworth
  • O5469557

Under Construction. Offering A Prime Location Within The Gates Of The Renowned Isleworth Golf & Country Club, This Two-story Estate Will Feature Magnificent Views Of Holes 11 And 12, As Well As... Read More

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Courtesy of Isleworth Realty Llc
  • $5,250,000
  • Single Family Home
  • 5/1
  • 7,543
  • 4
  • 9,718
  • 2011
  • Isleworth
  • O5231007

Back On The Market Due To No Fault Of The House ---buyer Could Not Perform!! Best Price Per Sq. On The Butler Chain In The Community! Isleworth Lake Front Estate. Breathtaking Views Of Lake Louise,... Read More

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Courtesy of Irwin Realty Group Llc
  • $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
  • $4,450,000
  • 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
  • $4,195,000
  • Single Family Home
  • 7
  • 7,607
  • 5
  • 10,961
  • 2004
  • Keenes Pointe Unit 01
  • O5522180

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... Read More

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Courtesy of Bhhs Results Realty
  • $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
  • $3,995,000
  • Single Family Home
  • 7
  • 8,379
  • 6
  • 10,794
  • 2002
  • Reserve At Lake Butler Sound 45/120
  • O5493331

Breathtaking Lake Front Estate Located In The 24 Hour Guard Gated Community Of Lake Butler Sound. This Luxurious Home Is The Epitome Of Lake Front Living With An Amazing Corner Lot And Remarkable... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $3,994,100
  • Single Family Home
  • 6
  • 7,884
  • 5
  • 9,697
  • 2001
  • Keenes Pointe Unit 01
  • O5472815

Welcome To Manoir Du Lac, A Magnificent Mansion On Lake Tibet, Part Of The Pristine Butler Chain Of 11 Lakes. This Discreetly Elegant French Country Chateau Is A Masterpiece Of Design And... Read More

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Courtesy of Real Property International
  • $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
  • 6
  • 7,400
  • 4
  • 9,671
  • 2012
  • Keenes Pointe Un 10
  • O5487172

Magnificent Mediterranean Mansion On Lake Tibet Butler In Keene's Pointe Is Simply A "work Of Art!" Intricate Architectural Style, Coupled With Interior Finishes That Rival Mansions From Around The... Read More

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Courtesy of Keene's Pointe Realty
  • $3,675,000
  • 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
  • $3,600,000
  • Single Family Home
  • 11
  • 9,376
  • 7
  • 11,940
  • 2008
  • Reserve At Lake Butler Sound 45/120
  • O5489066

Must See To Appreciate! Your Complete Lakefront Retreat, With Uncompromising Architectural Quality At Every Turn, Awaits. Nestled On 2.95 Acres On Lake Butler, This 9,376 Square Foot Estate Marries... Read More

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Courtesy of Lakeside Realty Windermere Inc
  • $3,550,000
  • Single Family Home
  • 5
  • 7,768
  • 5
  • 10,339
  • 1999
  • Keenes Pointe Unit 01
  • O5455349

Luxury Abounds In This Extraordinary Lakefront Estate On The Butler Chain Of Lakes In Keene's Pointe. Upon Entering The Stunning Foyer, The Dining & Living Rooms With Picturesque Views Of Lake Tibet... Read More

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Courtesy of Bhhs Results Realty
  • $3,500,000
  • 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
  • $3,489,000
  • 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
  • $3,450,000
  • 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
  • $3,200,000
  • Single Family Home
  • 6
  • 6,756
  • 5
  • 8,749
  • 2004
  • Reserve At Lake Butler Sound 45/120
  • O5513477

Elegant Estate In The Highly Sought Guard-gated Community, The Reserve At Lake Butler Sound. Perfectly Positioned On Nearly An Acre With Stunning And Unobstructed Views Of The Famed Lake Butler. The... Read More

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Courtesy of Lakeside Realty Windermere Inc
  • $3,199,000
  • 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
  • $3,150,000
  • Single Family Home
  • 8
  • 7,177
  • 6
  • 8,877
  • 2007
  • Aladar Rep
  • O5525009

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 Combines The... Read More

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Courtesy of Stockworth Realty Group
  • $2,995,900
  • Single Family Home
  • 7
  • 7,455
  • 4
  • 9,812
  • 1998
  • Isleworth 01 Amd
  • O5522834

The Golf Course Is The Stunning Backdrop For This European Architectural Style Custom Estate. The Circular Drive And Fountain Provide A Lovely Progression To The Solid Wood And Glass Arched Entry... Read More

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Courtesy of Premier Realty Partners Inc
  • $2,950,000
  • Single Family Home
  • 8
  • 6,933
  • 6
  • 9,028
  • 1991
  • Isleworth
  • O5506876

This Is A One Of A Kind Contemporary Home Located On The 5th Hole In The Gated Community Of Isleworth. The Home Has 6 Bedrooms And 6 Full & 2 Half Baths. Formal Living Rm And Dining Rm, Family Rm,... Read More

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Courtesy of Suzi Karr Realty

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