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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418 Properties Found. Showing Page 1 of 35
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9927 Giffin Ct, Windermere

Photo of Listing #O5704312

$28,000,000

  • 12 Beds
  • 11 Baths
  • 4 Half

  • 31,000 SqFt
  • 3.94 Acres

Single Family / Villa

Isleworth

Private Grandeur Embodied Isleworth Estate - Situated On 3 Acres Overlooking Tranquil Panoramic Lake Butler Sunset Views. This Magnificent Custom Estate Is Comprised Of Approximately 31,000 Square Feet Of Living Space, Which Includes A 6,000 Square Foot Indoor Basketball Court. Beautiful Double, Curved Stair Cases Greet You In The Two-story Foyer And Guides You To The Estate’s Magnificent Great Room. The Great Room Boasts Approximately 1,170 Square Feet, Built-in Sofas, 2 Story Marble Fireplace, Wood Beams With Large Corbels Then Complimente...

9912 Lake Louise Dr, Windermere

Photo of Listing #O5714911

$23,000,000

  • 11 Beds
  • 10 Baths
  • 4 Half

  • 25,466 SqFt
  • 3.19 Acres

Single Family / Villa

Isleworth 02 Amd

An Exquisite Waterfront Estate Within One Of Orlando's Most Sought After Golf Community Of Isleworth Country Club. This Impressive Mansion Offers Car Enthusiasts A Dream Showcase Garage That Can Accommodate Collections Of 40+ Cars. This Impressive Estate Features Nearly 800 Feet Of Water Frontage, Offering Commanding Views Of The Pristine Lake Waters Whether You Are In The Grand Entrance, Kitchen Or Guest Quarters. the Structural Balance And Perfection Of This Estate Is Shown Through It's Appealing And Accommodating Floorplan. Across The Hom...

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...

5372 Isleworth Country Club Dr, Windermere

Price
Reduced
Photo of Listing #O5700351

$8,600,000

  • 8 Beds
  • 9 Baths

  • 13,230 SqFt
  • 1.03 Acres

Single Family / Villa

Isleworth 01 Amd

This Exquisite One Of A Kind Isleworth Masterpiece Features Unparalleled Details And Craftsmanship Throughout. From The Hand Carved Millwork To The Imported Marble Fireplaces And Over 115 Italian Marble Columns, European Craftsmen Have Custom Fabricated Every Detail Of This Fabulous Home. As You Step Through The Front Doors You’re Immediately Greeted By Soaring Two Story Ceilings And A Rock Waterfall Spilling Into Koi Pond Directly Beneath Your Feet. Directly In Front Of You Is A Massive Gathering Room With Views Of The Pool And Lake. The Ki...

9368 Blanche Cove Dr, Windermere

Photo of Listing #O5565384

$7,950,000

  • 7 Beds
  • 7 Baths
  • 3 Half

  • 10,730 SqFt
  • 5.17 Acres

Single Family / Villa

Isleworth

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 Mahogany Wood Detail, A Wall Of Windows & Sliders Opening To The Terrace & A Truly Open Floor Plan. The Interior Boasts Over 10,700 Sq Ft Of Living...

5318 Isleworth Country Club Dr, Windermere

Photo of Listing #O5713515

$7,200,000

  • 6 Beds
  • 8 Baths
  • 2 Half

  • 12,128 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 12,000-square-foot Interior Of This Beautiful Estate. Built By Leading Custom Homebuilder Pellegrini Homes, The Master-designed Floor Plan Draws Every R...

11055 Bridge House Rd, Windermere

Photo of Listing #O5711522

$6,750,000

  • 6 Beds
  • 6 Baths
  • 3 Half

  • 10,452 SqFt
  • 2.48 Acres

Single Family / Villa

Reserve At Lake Butler S...

Masterpiece On The Butler Chain! Featuring Over 10,000 Square Feet Of Exquisitely Appointed Interior Living Space, On Over Two Privately Gated Acres With Panoramic Views Of The Famed Lake Butler, This Spectacular Residence Will Captivate At Every Turn. Enchanting Lake Views And Spacious Indoor-outdoor Living Spaces, United By Wall Of Sliding Glass Doors, Create A Seamless Connection To The 365 Feet Of Private Water Frontage. Terraced Patios, Swim-up Pool Bar, Natural Rock Waterfall, Private Dock And Meandering Pool Evoke A Private Resort An...

5506 Isleworth Country Club Dr, Windermere

Photo of Listing #O5573526

$6,650,000

  • 6 Beds
  • 7 Baths
  • 2 Half

  • 8,049 SqFt
  • 0.95 Acres

Single Family / Villa

Isleworth

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 Foyer Create The Ideal Introduction Into The Immaculate Estate. Beyond The Elegant Main Entry Is The Formal Dining Room With Ample Space For Entertai...

5354 Isleworth Country Club Dr, Windermere

Photo of Listing #O5713089

$6,300,000

  • 5 Beds
  • 6 Baths

  • 9,811 SqFt
  • 1.18 Acres

Single Family / Villa

Isleworth

Beautifully Mirrored In Hourglass Pond, This Home Was Designed To Reflect The Elegance Of An Old, Italian Villa Positioned On An Oversized Lot With More Than An Acre Of Lush, Manicured Gardens. Globally Sourced Materials, Including Medallions Of Ancient Terracotta, Marble And Granite Retrieved From The Same Vatican Quarries Outside Rome. Down The Brick-paver Driveway, Through The Honed-marble Framed Front Doors, You Are Welcomed By Jerusalem Limestone And A Sweeping Custom Wrought Iron Crafted Staircase. Overlooking Hourglass Pond Is The Kit...

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...

5020 Down Point Ln, Windermere

Photo of Listing #O5701437

$5,949,000

  • 5 Beds
  • 8 Baths

  • 9,621 SqFt
  • 2.01 Acres

Single Family / Villa

Sunset Bay Rep

Villa Constantia Is The Epitome Of Luxury Windermere Lake Front Living. Designed By Legendary Architect John Henry This Exquisite Lake Front Mansion Is Perfectly Positioned On Lake Down, Part Of The Renowned Butler Chain Of Lakes. Every Inch Of This Stunning Residence Is Built On A Grand Scale; From The 6 Car Garage, To The Soaring 30 Foot Ceilings, The 12 Seat Home Theater, A Breakfast Nook With Seating For 10, And A Private Fitness Center. This Amazing Estate Boasts Over 15,500 Total Square Feet Including Covered Patios And Outdoor Living ...

12824 Jacob Grace Ct, Windermere

Price
Reduced
Photo of Listing #O5573881

$5,775,000

  • 6 Beds
  • 7 Baths
  • 2 Half

  • 8,289 SqFt
  • 1.34 Acres

Single Family / Villa

Tildens Grove Ph 01 47/65

Inspiring Living, Sophistication, Elegance And Style. A Marvelous Lakefront Modern Contemporary Turnkey Home, Crafted From The Ground Up, Full Renovation Completed In 2018. This 6 Bed /7 Full Bath / 2 Half Bath Custom Built Home Designed By A Top Modern Home Design Studios In Florida, Ideal For Luxury Living Within The Architectural Balance Of Tranquility And Modern Living. Custom Designed Dining Room, Spacious Living Area Open To An Entertainer's Lavish Gourmet Kitchen Offers Top Of The Line Appliances. The Living And Kitchen Level Spans Mo...

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.


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 September 18th, 2018 at 11:45am EDT.