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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93 Properties Found. Showing Page 1 of 8
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9927 Giffin Court, WINDERMERE

New Photo of Listing #O5926057

$16,500,000

  • 12 Beds
  • 11 Baths
  • 4 Half

  • 31,000 SqFt
  • 3.94 Acres

Single Family Residence

Isleworth

Nestled In One Of Central Florida’s Most Exclusive 24-hour Privately Gated Golf Communities, Isleworth, Is A Rare And Unique Sprawling Lakefront Mansion. Positioned On 3.94 Acres With 700 Feet Of Lakefront On The Famous Butler Chain Of Lakes, This Mansion Comes Complete With A Ludowici Clay Tile Roof, 12 Bedrooms, 11 Baths And Four Half Baths Among 35,550 Total Square Feet. 12 Spacious Bedrooms Feature Breathtaking Panoramic Views Of Lake Butler, And An Array Of Amenities Includes A 6,000-square-foot Indoor Nba-certified Basketball Court, A ...

6432 Deacon Circle, WINDERMERE

New Photo of Listing #O5915892

$8,300,000

  • 5 Beds
  • 5 Baths
  • 4 Half

  • 11,229 SqFt
  • 0.80 Acres

Single Family Residence

Isleworth 1st Amendment

This Stunning Georgian Manor Located Within The Gates Of The Renowned Isleworth Community Tastefully Intertwines Timeless Old World Charm With Modern Style. Upon Entry, You Will Be Welcomed By The Grand Staircase While You Gaze Past The Wall Of Seamless Glass Overlooking Your Infinity Pool As It Appears To Flow Into Lake Chase; A Sand Bottom, Spring Fed Ski Lake. From The Four French Limestone Fireplaces And Custom Pillars To The Intricate Carvings And Cappuccino Marble Flooring, This Home Has Been Flawlessly Updated And Maintained. All Five...

9288 Blanche Cove Drive, WINDERMERE

New Photo of Listing #O5895605

$7,495,000

  • 6 Beds
  • 4 Baths
  • 4 Half

  • 12,778 SqFt
  • 2.04 Acres

Single Family Residence

Isleworth 7th Amd

Under Construction. Under Construction, With A Small Window Of Time To Still Make It Your Own. 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...

9838 Laurel Valley Drive, WINDERMERE

New Photo of Listing #O5911293

$6,300,000

  • 5 Beds
  • 6 Baths
  • 2 Half

  • 10,843 SqFt
  • 0.54 Acres

Single Family Residence

Isleworth

Capturing Majestic Sunset Views Of Beautiful Lake Butler, This Fabulous Lakefront Estate Is Perfectly Set Between Lake Butler’s Shoreline And The 15th Hole Of Isleworth’s Renowned Championship Golf Course. The Three-story Estate Offers A Nod To Mizner-inspired Architecture And Is Stunning In Both Scale And Contemporary Style. With Fresh, White Interiors, A Wealth Of Modern Accents And An Array Of Exciting Living Spaces, The Estate Is A Lakefront Paradise. Marble Floors With Onyx Inlays Lead From The Grand Two-story Foyer And Curved, Float...

5318 Isleworth Country Club Drive, WINDERMERE

New Photo of Listing #O5872952

$6,100,000

  • 6 Beds
  • 8 Baths
  • 2 Half

  • 12,298 SqFt
  • 1.74 Acres

Single Family Residence

Isleworth

New Price! Motivated Seller Offers A $500,000. Price Reduction! Wonderful Opportunity To Purhase In Exclusive Gated Golf And Country Club Community, Full-time Guard-gatehouse. Custom Built! Stunning Entrance. Pristine Condition. Dramatic Interior Includes An Interior Custom Designed Swimming Pool, In A Temperature-controlled Entertainment, Two-story Pavilion With Stone Flooring, Skylights, A Heated Pool And Spa, A Bar, Grilling/cooking Area, Dining Area And Lounging Area - All Of Which Is The Absolute Focal Point Of This Dramatic Int...

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...

5306 Isleworth Country Club Drive, WINDERMERE

New Photo of Listing #O5934539

$5,950,000

  • 5 Beds
  • 5 Baths
  • 3 Half

  • 8,802 SqFt
  • 0.57 Acres

Single Family Residence

Isleworth

Nestled Within The Main Gate Of Isleworth Golf & Country Club Along The Back Nine, This Exquisite Golf-front Estate Offers Beautiful Finishes And Living Spaces Set Against A Backdrop Of Multiple Golf And Water Views Overlooking Holes 11 And 12 Along Eagle Pond. Designed By Renowned Architect Terry Irwin And Built In 2018 By Leading Custom Home Builder Wyatt Anderson Construction, With Interiors By Design Studio 15, The Estate Offers More Than 8,800 Square Feet Of Living Space With A Wealth Of Modern Amenities And Appointments Throughout. T...

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...

11307 Bridge House, WINDERMERE

New Photo of Listing #O5923495

$4,200,000

  • 5 Beds
  • 6 Baths
  • 1 Half

  • 6,661 SqFt
  • 0.88 Acres

Single Family Residence

Reserve At Lake Butler S...

Elegantly Appointed Mediterranean Home Built By Ray Coudriet Located On The Butler Chain Of Lakes. Beautiful Property For The Discriminating Buyer Nestle Directly On Lake Butler. 5 Bedrooms, 5.2 Baths, With Direct Access To The Butler Bay Chain Of Lakes Consisting Of Over 11 Lakes And In The Exclusive Community Of The Reserve At Lake Butler Sound. This Wonderful Home Boasts Designer Touches Throughout, Including Your Own Elevator, 2 Sets Of Stairs, Theatre Downstairs As Well As Master Bedroom, Study, And A Second Bedroom. Grand Foyer Leads T...

11217 Bridge House Road, WINDERMERE

New Photo of Listing #O5914180

$3,799,000

  • 7 Beds
  • 8 Baths

  • 6,363 SqFt
  • 1.03 Acres

Single Family Residence

Reserve At Lake Butler S...

Exquisite Mediterranean Estate Featuring 99' Of Panoramic Views Of Lake Butler In Private Gated Community Of Lake Butler Sound. Custom Built In 2004, Interior Details Include 12' Ceilings, Crown Molding, 8' Doors, Mosaic Inlaid And Travertine Floors And French Doors Throughout With Water Views From Every Room. Outdoor Living Area Includes Oversize Salt Water Swimming Pool And Spa Surrounded By 16" X 16" Travertine Bricks, Summer Kitchen Featuring Ge Monogram Appliances And Stone Gas Burning Fireplace All Within Screened Enclosure. Ground ...

11025 Bridge House Road, WINDERMERE

New Photo of Listing #O5896580

$3,649,000

  • 7 Beds
  • 8 Baths
  • 2 Half

  • 9,594 SqFt
  • 2.89 Acres

Single Family Residence

Reserve At Lake Butler S...

Welcome To This Mediterranean Enchanting And Lavish Estate At The Heart Of Windermere In The Upscale Gated Community The Reserve At Lake Butler. This Stunning Property Embodies Florida Living At Its Finest, With Multiple Luxury Living Spaces That Include 6 En Suite Bedrooms, Plus A Master Bedroom With Fireplace And Spacious Walk In Closet, Living Room, Formal Dining Room, Awe-inspiring Kitchen With A Open Concept, Game Room, Movie Room, Workout Room, Bar, Wine Cellar And Much More... This Upscale Estate Has The Feel Of A Personal Res...

8304 Lake Burden Circle, WINDERMERE

New Photo of Listing #O5907662

$3,649,000

  • 8 Beds
  • 9 Baths
  • 1 Half

  • 8,808 SqFt
  • 0.57 Acres

Single Family Residence

Keenes Pointe Unit 2

Unparalleled Contemporary Home Within Windermere, Florida's Distinguished Keene’s Pointe Community Featuring The Golden Bear Golf And Country Club. This Home Is Currently The Only Contemporary Property Available In Keene's Pointe With Lake Access. Breathtaking Water Views And Featuring 7-bedroom Suites, Personal Elevator, Private Office, Four Spacious Garage Stalls, And Guest Quarters. You Can Enjoy The Splendid Sunrise And Sunset From Many Rooms Within This Stellar Property. The Home Features Large Outdoor Patios With Automated Screens Comp...

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 April 19th, 2021 at 5:39am EDT.