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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406 Properties Found. Showing Page 1 of 34
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9508 Windy Ridge Rd, Windermere

New Photo of Listing #O5746245

$28,500,000

  • 7 Beds
  • 12 Baths
  • 2 Half

  • 51,000 SqFt
  • 18.16 Acres

Single Family / Villa

Acreage & Unrec

Private Windermere Lakefront Compound With 18 Acres On The Butler Chain Of Lakes Offering An Unparalleled Presence And Prestige In Central Florida's Most Desirable Location. This Walled And Gated Estate Boasts A 25,000 Sqft. State-of-the-art Family Residence, A 5,600 Sqft Grand Lodge With Catering Kitchen And Entertainment Hall, A 4,000 Sqft Wood Paneled Air Conditioned Garage With 20 Ft. Ceilings And Tile Floors, Detached Office With Guest Apartment, A 3,800 Sqft Storage Building With 20 Ft. Ceilings, Separate Staff Living Quarters, And Mas...

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...

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 Lake, 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...

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 ...

5501 Isleworth Country Club Dr, Windermere

Photo of Listing #O5740376

$5,295,000

  • 5 Beds
  • 6 Baths
  • 2 Half

  • 6,956 SqFt
  • 0.87 Acres

Single Family / Villa

Isleworth

Located On The 14th Hole Of The World Famous Isleworth Golf Course This Magnificent Property Is Truly One Of The Most Spectacular Estates In The Area. Breathtaking Views From Every Room In The House.grand Foyer Leads To The Enormous Great Room With Vaulted Wooden Ceilings. Spacious Gourmet Kitchen With Top Of The Line Appliances, Is A Chefs Dream! Over 1,000 Bottle Climate Controlled Wine Cellar. This Home Was Completely Renovated In 2016. Reverse Osmosus Water Syatem, Crestron Audio Visual And Lutron Lighting Throughout! The Master Wing Has...

6342 Deacon Cir, Windermere

Photo of Listing #O5735188

$4,900,000

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 7,008 SqFt
  • 0.63 Acres

Single Family / Villa

Isleworth

Nestled Along The Lake In The Heart Of Isleworth, This Fully Updated Residence Offers A Prime Location Overlooking Lake Isleworth With Direct Access To The Renowned Butler Chain Of Lakes. The Five-bedroom Estate Spans 7,008 Square Feet Across Two Levels, With Exquisite Grounds And Spacious Outdoor Living Areas Designed To Maximize Florida Lakefront Living. Beyond Its Stately Entry With Solid Stone Columns And Custom French Doors With Glass And Iron Detailing, The Rich And Open Interior Is Flooded With Natural Light As Dramatic Windows Draw Y...

12202 Park Ave, Windermere

Price
Reduced
Photo of Listing #O5702966

$4,900,000

  • 4 Beds
  • 4 Baths

  • 5,162 SqFt
  • 3.24 Acres

Single Family / Villa

Chaine Du Lac / Windermere

Extraordinary And Private Lake Butler Estate With 3.24 Acres Of Manicured Grounds, 314 Ft Lake Shoreline (226 Ft Across), A Sprawling Custom Single Story Residence On Double Lot With Detached 4-car Garage, Separate Pool House And Mammoth 50x19ft Swimming Pool, Sandy Beach And Landing Area Plus Concrete Seawall, And Grandfathered Double Boat House With Garage Doors Featuring An Enclosed Sitting Room With Docking Pier That Cannot Be Duplicated. Welcome To “architectural Digest’s House Of The Year 1987”. Set Behind Its Own Private Gates Inside ...

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 November 17th, 2018 at 10:30am EST.