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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259 Properties Found. Showing Page 1 of 22
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9508 Windy Ridge Road, WINDERMERE

New Photo of Listing #O5890318

$30,000,000

  • 6 Beds
  • 12 Baths
  • 2 Half

  • 51,000 SqFt
  • 18.16 Acres

Single Family Residence

N/a

This 18-acre Private Walled And Gated Compound Is One Of The Most Exceptional Properties In Central Florida, Unrivaled By Its Sheer Size, Ideal Shape, Remarkable Topography And High Elevation. The Property Offers Over 600 Feet Of Unobstructed Views And Access To One Of Lake Bulter's Cleanest Lakes. The Unparalleled Location Provides The Privacy And Tranquility Of Living "amongst The Lakes" In Windermere Without The Hassle Of Long Commutes Through The Local Routes. The Stately Residence Offers The Perfect Combination Of Warmth And Tradition U...

9912 Lake Louise Drive, WINDERMERE

New Photo of Listing #O5714911

$23,000,000

  • 11 Beds
  • 10 Baths
  • 4 Half

  • 25,466 SqFt
  • 3.19 Acres

Single Family Residence

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...

9927 Giffin Court, WINDERMERE

New Photo of Listing #O5883078

$19,500,000

  • 12 Beds
  • 11 Baths
  • 4 Half

  • 31,000 SqFt
  • 3.94 Acres

Single Family Residence

Isleworth

Situated Within Isleworth Golf & Country Club - One Of Central Florida’s Top Gated Golf Communities. This Home Offers Nearly Four Acres Of Western Facing Waterfront Property With 700 Feet Of Prime Lake Frontage And Panoramic Views Of Lake Butler. Over 31,000 Square Feet Of Living Space, The 12-bedroom Estate Is Ideal For Its Privacy, Amenities And Sheer Space Offered For Seamless Indoor-outdoor Living. An Array Of Indoor Amenities Include A 6,000 Sq. Ft. Indoor Basketball Court, A 17+ Car Showroom-style Garage, A Cigar Bar With Walk-in Humid...

9288 Blanche Cove Drive, WINDERMERE

New Photo of Listing #O5895605

$7,495,000

  • 5 Beds
  • 4 Baths
  • 4 Half

  • 12,778 SqFt
  • 2.04 Acres

Single Family Residence

Isleworth 7th Amd

Under Construction. Nestled Behind The Famed Gates Of Isleworth, One Of The Most Exclusive Private Golf And Country Club Communities In The World, Situated On One Of The Last Waterfront Lots You Will Find This Gorgeous Homesite With Construction Well Underway! Offering Serene Views Of Lake Blanche And Towering Cypress Trees Framing A Canvas Of Sunsets, You Will Be Hard Pressed To Find A More Picturesque Setting. Transitional Style Mixed With More Modern Elements Sets The Stage For This One-of-a Kind Estate With A Skybox That Overlooks The In...

5372 Isleworth Country Club Drive, WINDERMERE

New Photo of Listing #O5834063

$7,400,000

  • 8 Beds
  • 7 Baths
  • 2 Half

  • 13,230 SqFt
  • 1.03 Acres

Single Family Residence

Isleworth

Discover The Very Best In Isleworth Living Through This Spectacular Estate Overlooking The Serene Waters Of Hourglass Lake. The Estate Is A Rich And Fascinating Masterpiece That Inspires Superior Craftsmanship And Exudes Both Sophistication And Panache At Every Turn. Unique Ceiling Displays, 9 Carved Marble Fireplaces And 111 Marble Columns Are Just Some Of The Extraordinary Details Adorning The 13,230-sq-ft, French Renaissance Interior. From The Lavish Entry Featuring A Custom Rock Waterfall, Grand Staircase And Two-story Vaulted Ceiling, T...

6010 Cartmel Lane, WINDERMERE

New Photo of Listing #S5038054

$7,000,000

  • 6 Beds
  • 7 Baths
  • 2 Half

  • 14,150 SqFt
  • 2.14 Acres

Single Family Residence

Reserve/lk Bulter Sound

Under Construction. Unique Opportunity To Own One Of The Last New Construction Estates On Lake Butler Chain Of Lakes, This Brand New Lake Front Custom Home Is Located In The Exclusive Community Of Lake Butler Sound Reserve And It Is One Of The Few Houses In Central Florida With A 3,000 Sqft Indoor Basketball Court!!!! This Amazing Estate Is Under Construction At The Moment And It Is A Great Time To Tour And Visualize Your Future Home By Yourself. It Will Feature An Exquisite Style With A Heated Area Of 14,900 Sqft With 6 Bedroom Suites, 7 Ba...

5318 Isleworth Country Club Drive, WINDERMERE

New Photo of Listing #O5872952

$6,750,000

  • 6 Beds
  • 8 Baths
  • 2 Half

  • 12,298 SqFt
  • 1.74 Acres

Single Family Residence

Isleworth

Immediately Impressive And Dramatic! Golf-front Custom Built Estate For Current Owner -the Fulfillment Of Your Dreams Of Owning A Florida Estate In Orlando's Most Exclusive, Gated, Amenity-rich Community- "isleworth Golf And Country Club" - Cited On An Almost 2-acre Golf-front Lot, And Beautifully Embraced By A Formal Manicured Landscape And Flower Gardens. The Porte-cochere Leads To A Double Door Entry, Which Opens To A Wide Two-story Marble Foyer. The Interior View Is Stunning The Moment You Enter! From The Two-story Wide Marble Foyer ...

5507 Worsham Court, WINDERMERE

New Photo of Listing #S5036746

$5,959,000

  • 5 Beds
  • 5 Baths
  • 4 Half

  • 10,200 SqFt
  • 0.97 Acres

Single Family Residence

Isleworth 1st Amd

Immaculate Custom Estate Perfectly Situated On The 14th Green Of The Isleworth Country Club. This Isleworth Mansion Features An Exquisite Transitional, Contemporary And Timeless Interior, Beautiful Golf Views And Plenty Of Space For Perfect Family Gatherings. The Unparalleled Grand Open Floor Plan Greets You With A Massive Soaring Two-story Foyer And Living Room Featuring Floor-to-ceiling Windows With Spectacular Golf Front Views. Entertain Friends And Family In The Fully Equipped Theatre Or The Generous Summer Kitchen Area Complemented By A...

5020 Down Point Lane, WINDERMERE

New Photo of Listing #O5701437

$4,949,000

  • 8 Beds
  • 8 Baths

  • 9,621 SqFt
  • 2.01 Acres

Single Family Residence

Sunset Bay Rep

Villa Constantia Is The Epitome Of Luxury Windermere Lakefront 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...

12624 Park Avenue, WINDERMERE

New Photo of Listing #O5868103

$4,723,000

  • 6 Beds
  • 6 Baths
  • 1 Half

  • 6,996 SqFt
  • 1.75 Acres

Single Family Residence

Chaine Du Lac

Pre-construction. To Be Built. Pre- Construction. Incredible Opportunity To Build Your Dream Home On The Butler Chain Of Lakes Or You Can Build This Plan. This Beautiful Transitional Style Home With An Open Concept Floorplan Is To Die For. As You Enter Through The 10ft Custom Steel Doors You Will Be Welcomed By Huge Great Room And A Line Of Sliding Doors That Pull Your Eyes Directly To The Lake, As You Approach The Kitchen You Will Notice A Top Of The Line Sub-zero And Wolf Appliances And 2 Gorgeous Quarts Wrapped Islands, The Laundry Area O...

416 East 7th Avenue, WINDERMERE

New Photo of Listing #O5894039

$4,200,000

  • 5 Beds
  • 6 Baths
  • 1 Half

  • 12,083 SqFt
  • 1.26 Acres

Single Family Residence

Windermere Town Rep

Escape The Hoa, & Arrive At 416 E 7th Ave. A One Of A Kind Trophy Estate Built By One Of Windermere's Finest Builders. Set On Over An Acre & Situated On Private Lake Bessie, This Home Offers Lakefront Living W/ Amenities Of A Luxury Resort. This European Villa Spans Over 10,000 Sq. Ft. Of Living. A Sprawling Open Floor Plan Welcomes You W/ Floor-to-ceiling Glass Stacking Doors That Open To A Large Living Area & Expansive Pool Lanai W/ Ample Space & Fireplaces For Quintessential Indoor/outdoor Living. The Cabana Suite Offers Private Living Qu...

8358 Lake Burden Circle, WINDERMERE

New Photo of Listing #O5871497

$3,995,000

  • 8 Beds
  • 8 Baths
  • 2 Half

  • 9,844 SqFt
  • 0.86 Acres

Single Family Residence

Keenes Pointe

Stunning French Chateau Nestled Along The Shores Of Lake Burden In The 24-hour, Guard-gated Community Of Keene’s Pointe. As You Step Through The Front Door, You Are Immediately Greeted By Soaring Two-story Ceilings And A Dramatic Double Marble Staircase. Luxury And Elegance Resonate Throughout This Exquisite Estate, From The Marble Floors With Onyx And Granite Inlays To The Intricate Ceiling Details And Gold Leaf Accents, No Expense Was Spared In The Construction Of This Beautiful Home. This Palatial Estate Includes A Total Of Eight Bedrooms...

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 October 20th, 2020 at 10:02pm EDT.