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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296 Properties Found. Showing Page 1 of 25
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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 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...

5372 Isleworth Country Club Dr, Windermere

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...

N/A, Windermere

Photo of Listing #O5872952

$6,750,000

  • 6 Beds
  • 8 Baths
  • 2 Half

  • 12,298 SqFt
  • 1.74 Acres

Single Family Residence

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 ...

9832 Laurel Valley Dr, Windermere

Photo of Listing #O5846898

$6,350,000

  • 6 Beds
  • 7 Baths
  • 3 Half

  • 11,100 SqFt
  • 0.60 Acres

Single Family Residence

Isleworth

Unparalleled Isleworth Estate With Amazing Views Of Lake Butler Combined With Direct Golf Course Frontage On Isleworth’s 15th Hole. This One Of A Kind Three Story Home Has Been Completely Renovated And Is Perched High Above The Famed Butler Chain Of Lakes Offering One Of A Kind Water Views. Featuring 6 Bedroom Suites, A Movie Theater, Huge Game Room, Personal Elevator, Wine Cellar, Fitness Room, Private Generator, And A Beautiful Office, This House Has Something For Everyone. The Minute You Walk Through The Front Doors Your Eyes Are Immediat...

5507 Worsham Ct, Windermere

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 Ln, Windermere

Price
Reduced
Photo of Listing #O5701437

$4,949,000

  • 5 Beds
  • 8 Baths

  • 9,621 SqFt
  • 2.01 Acres

Single Family Residence

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 ...

12624 Park Ave, Windermere

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...

10821 Bayshore Dr, Windermere

Photo of Listing #O5868073

$4,655,000

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 6,378 SqFt
  • 2.80 Acres

Single Family Residence

Bayshore Estates

Pre-construction. To Be Built. Pre-construction. Gorgeous Lot Available For You To Build Your Dream Home Or This Plan If You Desire. Bring Your Own Builder!! This Gorgeous Open Concept Home Offers All Of The Modern Conveniences You Would Expect From A Dream Home. As You Enter The Front Door Large Pane Windows Open Up The Spectacular Views Of Lake Down, To The Right You Will Find The Massive Kitchen With A Double Island Wrapped With Quartz Countertops, And Top Of The Line Sub-zero And Wolf Appliances The Breakfast Nook Is Perfectly Placed To ...

8358 Lake Burden Cir, Windermere

Photo of Listing #O5871497

$4,495,000

  • 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 Your 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 & 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 8 Bedrooms, 3 Master S...

6513 Rosella Ct, Windermere

Photo of Listing #O5872166

$4,200,000

  • 6 Beds
  • 6 Baths
  • 1 Half

  • 9,089 SqFt
  • 3.35 Acres

Single Family Residence

Keenes Pointe 46/104

Sitting On One Of The Most Magnificent And Private Lots In All Of Windermere, This 9,000+sf Estate Is Like No Other. Not Only Does The Lot Cover Over Three Acres, But It Is The Only Lot In The Community Of Keene's Pointe Surrounded On Two Sides By Water, Giving The Owner The Ultimate In Privacy And Seclusion. The Home's Floorplan Has Been Created In Such A Way To Allow Large Gatherings In The Main Rooms, But Also Allows You To Spread Out To Their Own Private Areas And Suites. Containing 6 Bedrooms, 6 1/2 Baths, Theater, Game Room, Bonus R...

9711 Deacon Ct, Windermere

Photo of Listing #O5868216

$3,995,000

  • 5 Beds
  • 3 Baths
  • 3 Half

  • 8,400 SqFt
  • 1.16 Acres

Single Family Residence

Isleworth

One Or More Photo(s) Has Been Virtually Staged. Isleworth Living At Its Best! Live The Good Life In This Sprawling Mansion Located On The Shores Of The Famed Butler Chain In The Main Section Of Isleworth. The Private, Gated Estate Has Been Extensively Updated In 2020 With A Brand New Boat Dock And A Fully Repainted Interior And Exterior – Now In A Fresh And Modern White Hue. The Sprawling Italian-style Interior Spans 8,400 Sq.ft. And Features Countless Artistic Finishes, Luxurious Living Spaces, A Grand 20’ Ceiling In The Foyer And Stunning ...

6025 Greatwater Dr, Windermere

Photo of Listing #O5877250

$3,899,000

  • 7 Beds
  • 7 Baths
  • 1 Half

  • 7,812 SqFt
  • 2.74 Acres

Single Family Residence

Keenes Pointe

Masterfully Custom Designed Butler Chain Of Lakes Estate Positioned On One Of The Best Lakefront Lots In Keene’s Pointe!! Here's Your Opportunity To Purchase A Rare 7 Bedroom, 7.5 Bath, Coveted Greatwater Estate, Boasting Just Under 8000 Sq Ft. It's Luxury Is Uniquely Embodied In The Gracious Layout, Offering Unparalleled Views Of Lake Butler And Capturing Stunning Vistas From Virtually Every Room. The Resort Style Pool And Spa With Expansive Outdoor Entertaining Areas Preside Over A Fully Landscaped, Lush Lawn Leading To A Custom Dock With ...

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 August 11th, 2020 at 3:00pm EDT.