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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323 Properties Found. Showing Page 1 of 27
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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...

12488 Park Ave, Windermere

Photo of Listing #O5757261

$16,600,000

  • 10 Beds
  • 12 Baths
  • 5 Half

  • 13,425 SqFt
  • 2.75 Acres

Single Family / Villa

Chaine Du Lac

Exquisite Butler Chain Estate Designed By Renowned International Interior Designer And Artist Angela Huntington. This Stunning Windermere Residence Has Recently Undergone A Ground Up Remodel Comprising Finishes And Features That Are Unparalleled By Any Home In Central Florida. As You Step Through The Front Doors, You’re Immediately Greeted By Soaring 30 Ft Ceilings And A Sleek Modern Design With Amazing Lake Views From Almost Every Room. Interior Amenities Include A Private Spa, Fitness Center, Home Theater, Chef Inspired Kitchen, And A Mass...

5372 Isleworth Country Club Dr, Windermere

Price
Reduced
Photo of Listing #O5700351

$7,790,000

  • 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

Price
Reduced
Photo of Listing #O5713515

$6,750,000

  • 6 Beds
  • 8 Baths
  • 2 Half

  • 12,298 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...

6321 Greatwater Dr, Windermere

Photo of Listing #O5783096

$5,999,999

  • 6 Beds
  • 6 Baths
  • 3 Half

  • 9,951 SqFt
  • 1.46 Acres

Single Family / Villa

Keenes Pointe

Welcome To Maison Des Fleurs In Keene’s Pointe In Windermere, Florida. Custom Estate Home Located On A Private Cove On Lake Tibet, Of The Butler Chain Of Lakes. Offering Formal Living/dining Rooms, Piano Enclave, Wet Bar & Wine Cellar, And Chef’s Kitchen With Rustic Cabinetry, Wolf And Miele Appliances, A Spacious Breakfast Bar And Pantry Overlooking The Breakfast Nook & Family Room. Off The Family Room Is The “steam Punk” Themed Theater & Game Room W/full Bar. There Is A 2nd Ensuite Bedroom Downstairs, Large Laundry/work Room, 2 Half Bath...

5139 Fairway Oaks Dr, Windermere

Price
Reduced
Photo of Listing #O5775789

$5,395,000

  • 6 Beds
  • 6 Baths
  • 3 Half

  • 11,163 SqFt
  • 0.97 Acres

Single Family / Villa

Isleworth

Seller Requirement: Buyer Must Produce Proof Of Funds At Full Listing Price. Nestled On A Picturesque Home Site Along The Shores Of Lake Bessie, This Commanding Waterfront Residence Blends A Spanish Mediterranean Exterior With A Modern Transitional Interior. Spanning More Than 11,000 Square Feet, The Six-bedroom Estate Boasts Unique Hand-selected Finishes And Accompaniments At Every Turn, From The Grand Foyer And Gallery Entry To The Open Great Room With Soaring Ceiling, Custom Fireplace, Grand Staircase And Floor-to-ceiling Windows Framing ...

5020 Down Point Ln, Windermere

Price
Reduced
Photo of Listing #O5701437

$4,949,000

  • 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 ...

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...

9711 Deacon Ct, Windermere

Photo of Listing #O5777309

$4,395,000

  • 5 Beds
  • 5 Baths

  • 8,400 SqFt
  • 1.16 Acres

Single Family / Villa

Isleworth

Stunning Butler Chain Lake Front Estate Nestled Along The Shores Of Lake Isleworth. Located In Renowned Isleworth Golf And Country Club This Sprawling Estate Offers One Of A Kind Panoramic Sunset Views From Its 360 Feet Of Lake Frontage. As You Pull Through The Private Gate And Into The Motor Court Your Eyes Are Immediately Greeted By The Homes Fine Finishes And Exquisite Details. The Custom Iron Doors Lead You To The Grand Foyer With Its Soaring 20 Foot Ceilings, Rich Marble Floors With Custom Inlaid Tiles, A Gorgeous Chandelier, And Large ...

11127 Bridge House Rd, Windermere

Price
Reduced
Photo of Listing #S5016752

$4,300,000

  • 6 Beds
  • 6 Baths
  • 1 Half

  • 10,368 SqFt
  • 2.24 Acres

Single Family / Villa

Reserve At Lake Butler S...

Extraordinary, Lakefront, Six Bedroom, 10,000 + Square Foot Estate (heated Square Footage Includes Guest House, Theater + Game Room In Basement) Located In The Exclusive Community Of Lake Butler Sound. Interior Design By Acclaimed Designer "perla Lichi" And Built By Ray Coudriet In 2007. This Home Is Sited On One Of The Largest Lake Front Lots In The Community At Just Under Two Acres. Side Entry Four Car Garage With Circular Driveway Lead To A Grand Stone Entry With Custom Iron Doors. Upon Entering The Estate You Will Immediately Be Drawn To...

5501 Isleworth Country Club Dr, Windermere

Price
Reduced
Photo of Listing #O5740376

$4,200,000

  • 6 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.completely Renovated In 2017. All New Bathrooms, State Of The Art Smart House Electronic Syatem Thoughout, All New Airconditioners, All New Top Of The Line Appliances, Freshly Painted Inside And Out. Grand Foyer Leads To The Enormous Great Room With Vaulted Wooden Ceilings And Black Walnut Floors. Spacious Gourmet Kitchen. Over 1,000 Bottle Clim...

11103 Bridge House Rd, Windermere

Price
Reduced
Photo of Listing #O5745102

$4,150,000

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 9,403 SqFt
  • 1.74 Acres

Single Family / Villa

Reserve At Lake Butler S...

This Newly Remodeled Mediterranean-style Lakefront House Combines An Elegant Yet Casual Open Concept Floor Plan That Provides A Comfortable Family Experience. Sitting On 1.7 Acres, This 4 Bed, 4/2 Bath House Offers Stunning Views Of Lake Butler, A Resort Style Pool With Spa, Outdoor Kitchen, Fireplace, And A Covered Boat Dock With Lift That Awaits The Water Sports Enthusiast. The Floor-to-ceiling Windows In The Living Room Allow Panoramic Views And An Abundance Of Natural Light That, Combined With The Stylish Fireplace, Enhances The Space. ...

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 DBA Stellar MLS.

Listing information last updated on September 18th, 2019 at 1:15am EDT.