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
  • $30,000,000
  • Single Family Home
  • 14
  • 51,000
  • 6
  • 51,000
  • 2011
  • Acreage & Unrec
  • O5412382

Private Windermere Lakefront Compound With 18 Acres On Lake Down On The Butler Chain Offering An Unparalleled Presence And Prestige In Central Florida’s Most Desirable Location. This Walled And... Read More

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Courtesy of Stockworth Realty Group
  • $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
  • $7,225,000
  • Single Family Home
  • 6
  • 9,811
  • 5
  • 14,417
  • 2002
  • Isleworth 01 Amd
  • O5405442

Seller Requirement: Buyer Must Produce Proof Of Funds At Full Listing Price. Beautifully Mirrored In Hourglass Pond, This Home Was Designed To Reflect The Elegance Of An Old, Italian Villa Positioned... 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
  • $6,000,000
  • Single Family Use
  • Acreage & Unrec
  • O5452106

Exceptional Lakefront Opportunity. Build Your Dream Mansion Behind The Secured Walls Of Windermere’s Largest Estate. Perched Above Lake Down With A Downward Slope To The Water Affording Maximum... Read More

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Courtesy of Stockworth Realty Group
  • $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
  • $5,495,000
  • 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

Reduced!!!!!best Price Per Sq. On The Butler Chain In The Community! Isleworth Lake Front Estate. Breathtaking Views Of Lake Louise, Of The Butler Chain Of Lakes, Form Almost Every Room In The House.... Read More

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Courtesy of Irwin Realty Group Llc
  • $4,999,999
  • Single Family Home
  • 9
  • 10,701
  • 6
  • 15,612
  • 2008
  • Isleworth
  • O5448971

Positioned On A Corner Home Site Within The Renowned Isleworth Golf & Country Club, This Beautiful Estate Offers A Contemporary Feel And Neoclassical Architectural Styling. The Interior Spans More... Read More

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Courtesy of Isleworth Realty Llc
  • $4,550,000
  • Single Family Home
  • 7
  • 7,122
  • 4
  • 11,776
  • 2005
  • Isleworth
  • O5301368

This Sprawling Tuscan-inspired Estate Provides An Unparalleled Venue For Indoor-outdoor Entertaining With A Backdrop Of Sweeping Fairway Views. The Entrance Features A Floating Staircase Leading To... Read More

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Courtesy of Isleworth Realty 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
  • $4,250,000
  • Single Family Home
  • 6
  • 8,379
  • 5
  • 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
  • $4,150,000
  • Single Family Home
  • 7
  • 9,207
  • 5
  • 13,130
  • 2007
  • Keenes Pointe Unit 03 46/104
  • O5447381

Stunning French Country Estate Located In The Exclusive Guard Gated Community Of Keene’s Pointe. Luxury And Elegance Resonate Throughout This Magnificent Residence. From The Two Story Stone... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $4,000,000
  • 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.
  • $3,999,000
  • 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
  • $3,999,000
  • Single Family Home
  • 6
  • 7,884
  • 5
  • 9,697
  • 2001
  • Keenes Pointe Unit 01
  • O5472815

Price Reduced For A Quick Sale. Extraordinary French Country Estate On The Butler Chain Of Lakes In Desirable Keene’s Pointe, Windermere, Fl. Spanning Over 7800 Sf, This Magnificent Waterfront... Read More

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Courtesy of Real Property International
  • $3,995,000
  • 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
  • $3,650,000
  • 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
  • $3,600,000
  • 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

Price Adjustment! Seller Motivated! Located On Butler Chain Of Lakes. Beyond The Circular Driveway With Fountain And Porte-cochere Entry, French Doors Open To A Stunning Two Story Living Room, With... 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
  • 6
  • 6,080
  • 6
  • 7,806
  • 2005
  • Keenes Pointe Unit 03 46/104
  • O5499493

Welcome To 9327 Dole Circle, Your Ultra-private, Lakefront Estate Featuring Over 2.5 Acres High And Dry Of Ultimate Seclusion And Luxury. This Custom Masterpiece Boasts Superior Craftsmanship And... Read More

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Courtesy of Stockworth Realty Group
  • $3,300,000
  • Single Family Home
  • 6
  • 7,208
  • 5
  • 9,740
  • 2006
  • Aladar On Lake Butler
  • O5478155

Entertaining Guests Has Never Been Easier And More Stylish In This Home Designed Around The Infinity Edge Pool And Custom Aquarium. Located In Desirable Olde Windermere, On The Famed Butler Chain Of... Read More

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Courtesy of Regal R.e. Professionals Llc
  • $3,250,000
  • Single Family Home
  • 6
  • 6,603
  • 5
  • 8,749
  • 2004
  • O5445501

Reduced! It’s Very Simple – Location Location Location! Be Greeted With A Stunning Entry Walkway Looking Out To The Verdant Landscaping And Splashing Fountain Encased In A Magnificent Two-story... Read More

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Courtesy of Agent Trust Realty Corporation

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