Windermere Vacation Homes for Sale

Orlando vacation home buyers who appreciate luxury living, an abundance of water activities, and close proximity to area theme parks often find themselves choosing property in Windermere. The southwest Orange County town is just minutes from Walt Disney World and features some of the most affluent waterfront real estate in Central Florida.

Windermere is known as the “Town Among the Lakes” because it is located on an isthmus between several lakes in the Lake Butler chain of lakes. These beautiful lakes provide much of the appeal to full and part-time residents, who enjoy a variety of activities such as championship fishing, lake cruises, boating, canoeing and kayaking.

Check out the available Windermere vacation real estate listings below, or continue reading to learn more about the many wonderful holiday communities found in the city!

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442 Properties Found. Showing Page 1 of 37
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N/A, Windermere

Photo of Listing #O5498420

$18,950,000

  • 9 Beds
  • 13 Baths
  • 4 Half

  • 20,240 SqFt
  • 4.78 Acres

Single Family / Villa

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 Basketball, Sand Volleyball, Citrus Orchard, Zip Line, Children's Treehouse With Electricity, And A Resort Pool With Grotto And Swim Up Bar With Hibachi Gri...

5536 Isleworth Country Club Dr, Windermere

Photo of Listing #O5394385

$15,000,000

  • 7 Beds
  • 9 Baths
  • 1 Half

  • 13,519 SqFt
  • 1.89 Acres

Single Family / Villa

Isleworth

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 Encompasses More Than 13,000 Square Feet Of Living Space, With Elegant Appointments Throughout. The Resplendent Interior Showcases Formal Living And Dining Rooms, Each Accented By Elegant Fireplaces And Chandeliers. Designed For Two Chefs, The Kitchen Features Three Islands, Two Jenn-air Stoves With Gas Cooktops And Three Sub-zero 700 Series Refri...

5115 Fairway Oaks Dr, Windermere

Price
Reduced
Photo of Listing #O5433535

$10,999,000

  • 7 Beds
  • 7 Baths
  • 4 Half

  • 15,063 SqFt
  • 3.76 Acres

Single Family / Villa

Isleworth

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 Such As Imported Stone And Antique Details Travel Throughout The Master-designed Floor Plan, From The Formal Dining Room, Kitchen And Breakfast Are...

5318 Isleworth Country Club Dr, Windermere

Photo of Listing #O5441428

$8,500,000

  • 6 Beds
  • 8 Baths
  • 1 Half

  • 11,182 SqFt
  • 1.74 Acres

Single Family / Villa

Isleworth

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 Entry, A Pair Of French Doors Open To The Grand Foyer Featuring A Curved Staircase, Wine Cellar And Polished Marble Floors With An Intricate Medallion Inlay—all Leading Graciously Into The More Than 11,000-square-foot Interior Of This Beautiful Estate. Built By Leading Custom Home Builder Pellegrini Homes, The Master-designed Floor Plan Draws Every ...

11055 Bridge House Rd, Windermere

Photo of Listing #O5534935

$7,499,000

  • 6 Beds
  • 6 Baths
  • 3 Half

  • 10,452 SqFt
  • 2.48 Acres

Single Family / Villa

Reserve At Lake Butler S...

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 Panoramic Views Of Famed Lake Butler, This Spectacular Residence Will Captivate At Every Turn. Enchanting Views & Spacious Indoor-outdoor Spaces, United By Walls Of Sliding Glass Doors, Create A Seamless Connection To The Nearly 365 Ft Of Private Water Frontage With Dock. The Terraced Patios, Sunken Summer Kitchen, Swim-up Pool Bar, Natural Rock Waterf...

5018 Latrobe Dr, Windermere

Price
Reduced
Photo of Listing #O5460974

$6,195,000

  • 7 Beds
  • 7 Baths
  • 3 Half

  • 12,353 SqFt
  • 0.67 Acres

Single Family / Villa

Isleworth

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, Stonework And Extensive Marble Throughout Set The Tone For The Three-story Home Encompassing More Than 12,300 Square Feet Of Living Space. The Main Level Boasts A Beautiful Foyer With Grand Staircase And Opens To The Formal Living Room With Volume Ceilings, A Stone Fireplace And Breathtaking Water Views. The Spacious Kitchen Boasts A Warm Mix Of Cust...

5180 Vardon Dr, Windermere

Photo of Listing #O5529368

$5,895,000

  • 5 Beds
  • 5 Baths
  • 3 Half

  • 11,340 SqFt
  • 1.68 Acres

Single Family / Villa

Isleworth

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 Spacious And Elegant Interior Totaling More Than 11,000 Square Feet, With Impeccable Design, Superb Luxuries And A Sprawling Floor Plan Brimming With Exquisite Finishes. The Rich Ambiance Of The Five-bedroom Estate Reflects Old World Style, From The Formal Living And Dining Rooms Accented By Intricate Ceilings To The Gourmet Kitchen Characterized By Beau...

9832 Laurel Valley Dr, Windermere

Photo of Listing #O5510614

$5,750,000

  • 6 Beds
  • 7 Baths
  • 3 Half

  • 11,100 SqFt
  • 0.60 Acres

Single Family / Villa

Isleworth

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 Famed Butler Chain Of Lakes Offering Incredible Water Views. Featuring 6 Bedroom Suites, A Movie Theater, Game Room/casino, Personal Elevator, Wine Cellar, Fitness Room, Play Room, Private Generator, And Two Offices, This House Has Something For Everyone. The Minute You Walk Through The Front Doors Your Eyes Are Immediately Drawn To The Soaring Two St...

9711 Deacon Ct, Windermere

Price
Reduced
Photo of Listing #O5514968

$5,450,000

  • 5 Beds
  • 3 Baths
  • 3 Half

  • 8,400 SqFt
  • 1.16 Acres

Single Family / Villa

Isleworth

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 Personal Private Gate, You’ll Find Yourself Mesmerized By The Large Private Courtyard, Panoramic Water Views And Breathtaking Sunsets. This Home Reflects The Charm And Elegance Of Italy With Globally Sourced Materials Including Italian Marble Fireplaces, Inlaid Sistine Inspired Tiles, Hand Textured Walls, Chiseled Marble Floors And Gorgeous Granite Coun...

9832 Lake Louise Dr, Windermere

Price
Reduced
Photo of Listing #O5231007

$5,250,000

  • 4 Beds
  • 5 Baths
  • 1 Half

  • 7,543 SqFt
  • 0.57 Acres

Single Family / Villa

Isleworth

Never Even Lost Power During Hurricane Irma!!!! 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. This Property Was Taken Down To The Studs In 2010 And Was Rebuilt With The Finest Materials And Craftsmanship Available. 2 Gourmet Kitchens. One Inside And One Outside. First Floor Master Suite With Spectacular His And Hers Closets. The Master Bath Is Equipped With A Spa Tub Over Sized Shower And Heated Floor...

11049 Bridge House Rd, Windermere

New Photo of Listing #O5538299

$4,995,000

  • 5 Beds
  • 7 Baths
  • 2 Half

  • 10,112 SqFt
  • 2.90 Acres

Single Family / Villa

Reserve At Lake Butler S...

Stunning European Architectural Style Estate In Guard Gated Lake Butler Sound On Sparkling Lake Butler Of The Butler Chain Of Lakes. Mature Landscaping, Private Gates, And Inviting Circular Pavered Motor Court Offer A True Sense Of Arrival To This One Of A Kind Estate, Built By Master Custom Builder, Jim Akers. Triple Sets Of French Doors With Arched Windows Above And Two Story Ceiling Details Define The Formal Areas, Highlighted By Polished Travertine Flooring, Columns, And A Large Precast Stone Gas Fireplace. Just Off The Entry, The Librar...

11536 Lake Butler Blvd, Windermere

Photo of Listing #O5504189

$4,495,000

  • 5 Beds
  • 6 Baths
  • 2 Half

  • 8,051 SqFt
  • 2.19 Acres

Single Family / Villa

Replat Of Metcalf Park

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 Greeted By Timeless Elegance That Is A Classic Plantation Style Manor. Step Inside The Grand Foyer Of This 5 Bedroom, 8 Bath Residence To Find Formal Det...

The Windermere Community

The town was chartered in 1925, but its history goes back much further, to 1889 when two Englishmen, the Rev. Joseph Hill Scott and his son Dr. Stanley Scott, started a settlement on the shores of Lake Butler. The town’s oldest structure is a one-room schoolhouse from that era, which has been restored to reflect its place as a site for educating children of citrus grove owners, workers and farm hands.

Today, Windermere features a quaint city center with charming shops and cafes, as well as a number of outstanding golf courses, such as The Golden Bear Club at Keene’s Pointe, designed by golfing great Jack Nicklaus and Isleworth, designed by golf legend Arnold Palmer.

Windermere Real Estate Market

In addition to waterfront luxury, Windermere also features stunning townhomes and condos that require less upkeep, while allowing you to relax in comfort and even enjoy the Disney fireworks from your backyard.

Browse Windermere Communities:

If you’d like more information about purchasing a second home in Windermere, contact a Team Donovan agent at 407-704-2616 or or visit us online.

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS.

Listing information last updated on October 20th, 2017 at 10:48pm EDT.