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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65 Properties Found. Showing Page 1 of 6
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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

$8,295,000

  • 6 Beds
  • 8 Baths
  • 2 Half

  • 11,990 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...

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

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 An Expansive...

9838 Laurel Valley Drive, WINDERMERE

New Photo of Listing #O5911293

$5,900,000

  • 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...

9905 Lake Louise Drive, WINDERMERE

New Photo of Listing #O5945140

$4,360,000

  • 4 Beds
  • 6 Baths
  • 1 Half

  • 7,122 SqFt
  • 1.06 Acres

Single Family Residence

Isleworth

Nestled On More Than An Acre Within The Private Guard-gated Community Of Isleworth, This Extraordinary Custom Golf-front Estate Offers Exquisite Living In The Heart Of One Of The Finest Golf Club Communities In The World. Built By Leading Custom Home Builder Pellegrini Homes, This Stunning Italian Masterpiece Spans More Than 7,100 Square Feet With Lavish Detail, Impeccable Resort-style Grounds And Plenty Of Privacy Creating A Golf-front Haven. Beautifully Handcrafted Cypress Grand Entrance Doors Reveal A Gracious, Open Interior Featuring C...

11307 Bridge House Road, 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...

5120 Isleworth Country Club Drive, WINDERMERE

New Photo of Listing #O5947403

$3,750,000

  • 5 Beds
  • 6 Baths
  • 1 Half

  • 7,070 SqFt
  • 0.97 Acres

Single Family Residence

Isleworth

Situated On An Acre Overlooking Isleworth’s 7th Green And The Beautiful Lake Bessie, This Five-bedroom Estate Offers Exquisite Evening Sunsets In The Heart Of Isleworth. The Interior Spans More Than 7,000 Square Feet With A Dynamic Design That Makes Full Use Of Art Deco Geometry In The Windows, Doors And Ceilings Throughout. The Spacious Interior Is Configured Like A Grand Hotel, With Main Rooms Opening To Central Galleries That Serve As Organizing Elements And Gorgeous Windows That Flood The Home With Natural Light. Superb Exterior Featur...

13643 Lake Cawood Drive, WINDERMERE

New Photo of Listing #O5973104

$3,680,000

  • 6 Beds
  • 8 Baths
  • 1 Half

  • 8,203 SqFt
  • 1.00 Acres

Single Family Residence

Lake Cawood Estates

Custom Home With One Acre Lot In Exclusive Lake Cawood Estates In Windermere. Built From Icf Insulated Concrete Blocks For Superior Energy Efficiency And Hurricane Protection With Foam Roof Insulation, Barrel Tile Roof And $25k Whole House Generator Included. Built Only Three Years Ago This Home Features The Latest In Technology And Designer Trends-whole House Zoned Audio System, Multi Point Camera Security System, 4 Tankless Energy Efficient Hot Water Heaters, Three Top Of The Line American Standard A/c Units, Designer Light Fixtures, Wood ...

3026 Porto Lago Court, WINDERMERE

New Photo of Listing #O5956476

$3,369,000

  • 6 Beds
  • 7 Baths
  • 2 Half

  • 8,714 SqFt
  • 2.17 Acres

Single Family Residence

Lake Down Pointe 50 42

Almost 9000 Heated Square Feet Of Superior Living On The Butler Chain! Located Within The Private And Gated Community Of Marbella, This Exquisite Custom Windermere Pool Home Showcases Superior Finishes Throughout The Home: Including Custom European Iron Work, Wood Beams, Cathedral Ceilings, Travertine Floors, Custom Iron Door And A Grand Large Foyer Entrance Overlooking The Beautiful Resort Style Living. The Expansive West Wing Of This Home Features A Very Private Master Bedroom Featuring Volume Ceilings And Exposed Wood Beams Along With ...

4705 Joanna Garden Court, WINDERMERE

New Photo of Listing #O5956126

$3,185,000

  • 4 Beds
  • 4 Baths
  • 2 Half

  • 6,060 SqFt
  • 0.26 Acres

Single Family Residence

Isleworth

Exquisite Mediterranean Trophy Home Located In World Renowned Isleworth Golf And Country Club. This Magnificent Estate Features 4 Bedrooms, 4 Full Baths, 2 Half Baths. Finished With The Highest Quality Materials And Craftsmanship And Stunning Architectural Details. Oversized Gourmet Kitchen With Walk In Pantry. There Are Two Master Suites And Detached Guesthouse. Fantastic Outdoor Living And Dining Area With Fireplace, Summer Kitchen With Amazing Pool And Spa. Isleworth Is Conveniently Located Minutes From The Attractions, Restaurant Row, Th...

802 West 2nd Avenue, WINDERMERE

New Photo of Listing #O5971407

$2,899,000

  • 5 Beds
  • 6 Baths

  • 4,865 SqFt
  • 0.47 Acres

Single Family Residence

Aladar On Lake Butler

This Stunning Mediterranean-style Home Nestled In The Heart Of Old Windermere Is The Epitome Of Lakefront Living. From The Moment You Arrive, You Will Feel Relaxed. Once Through The Door, You Cannot Help But Be Impressed With The Stunning View Of Lake Butler. The High Ceilings In The Foyer, Formal Living Room And Dining Room Create A Wonderful Feeling Of Space, Perfect For Entertaining. As You Walk Around The House, You Will See The Care And Attention That The Owners Have Put Into This Home, Plus The Quality Of Workmanship. The View Of The L...

3165 Butler Bay Drive N, WINDERMERE

New Photo of Listing #O5945645

$2,690,000

  • 7 Beds
  • 7 Baths
  • 1 Half

  • 8,812 SqFt
  • 1.01 Acres

Single Family Residence

Butler Bay

Beautiful Modern Estate Constructed To Seamlessly Display Contemporary Elegance And Timeless Design. Sited On A 1-acre Lot, This 7-bedroom, 7.5 Bathroom Home Was Built In 2015. This Modern Lakefront Home Exudes Sophistication With A Theater, Panoramic Views Of Lake Crescent, And Open Design. Polished Natural Stone Floors And Gorgeous Custom Lighting Greet You As Your Eyes Are Instantly Drawn To The Breathtaking Views Through Floor-to-ceiling Windows Of The Grand Living Room. The Kitchen Is A Professional Chef’s Dream, Featuring Top-of-the-li...

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 27th, 2021 at 6:34am EDT.