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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75 Properties Found. Showing Page 1 of 7
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3801 Mckinnon Road, WINDERMERE

New Photo of Listing #O6004619

$10,000,000

  • 6 Beds
  • 12 Baths
  • 3 Half

  • 24,080 SqFt
  • 2.45 Acres

Single Family Residence

The Lake House

One Or More Photo(s) Has Been Virtually Staged. Under Construction. The Most Anticipated Listing To Hit The Market In Orlando This Year: The Lake House 2022 - An Award-winning Spec Home On The Final Stages Of Completion. Reputable Equestrian Side Of Windermere, By Lake Butler. The Only Design In The Usa ( Florida ) To Make It To The Top 10 Best Projects In The Planet By W.a.f. ( World Architecture Festival ) In Europe. The Largest Residential Project In The Usa For Tesla With Over 11,000 Sq Ft Of The Highly Advanced Tesla Roof Tiles, Widely ...

5139 Isleworth Country Club Drive, WINDERMERE

New Photo of Listing #O6026101

$8,900,000

  • 7 Beds
  • 7 Baths
  • 1 Half

  • 13,973 SqFt
  • 1.92 Acres

Single Family Residence

Isleworth 01 Amd

Spectacular Tuscan Modern Custom-built Estate Is The Ultimate Golfer’s Dream. This Is A Once In A Lifetime Opportunity To Own This Captivating Villa Inspired By The Italian Renaissance Which Offers An Exquisite Location Within The Main Gates Of The Exclusive Award-winning Community Of Isleworth Golf & Country Club Former Home Of Tiger Woods And Shaquille O Neal. Double Iron Doors And One A Kind Water Fountain In A Circular Driveway Enhance Entrance And Welcomes New Owners/ With Over 13,000 Sqft Sitting On Double Lot Almost Two Acres Of Total...

6513 Rosella Court, WINDERMERE

New Photo of Listing #O6022798

$8,590,000

  • 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, With Your Own Personal View Of Nightly Disney Fireworks From Both Magic Kingdom And Epcot, This 9,000+sf Estate Is Like No Other. Not Only Does The Property Cover Over Three Acres And Sit On A Cul-de-sac, 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 Floor-plan Has Been Created In Such A Way To Allow Large Gatherings In The Main Living Areas, But Also Al...

11035 Schooner Way, WINDERMERE

New Photo of Listing #O5992601

$7,500,000

  • 7 Beds
  • 5 Baths
  • 2 Half

  • 15,000 SqFt
  • 1.05 Acres

Single Family Residence

Marina Bay Estates

Pre-construction. To Be Built. Where Art Meets Architecture! Build Your Custom Dream Home With State Of The Art Energy Efficiency Engineering In The Tranquility Of The Sought After Town Of Windermere. Surrounded By The Butler Chain Of Lakes. Award Winning Architects, Jwb, And Award Winning Builder, William Edward Construction. Per Builder, Lot Can Support A 10,000 - 15,000 Square Foot Custom Home. Price Will Vary As Applicable.

10988 Down Yonder Lane, WINDERMERE

New Photo of Listing #O6021133

$7,500,000

  • 4 Beds
  • 4 Baths
  • 2 Half

  • 8,446 SqFt
  • 6.82 Acres

Single Family Residence

Lake Down Estates

Pre-construction. To Be Built. The Possibilities Are Endless When It Comes To The Only 6.82 Acre Lake Front Property Available On Lake Down In The Heart Of Windermere. With The Plans And Permits Now In Hand, You Do Not Want To Miss This Custom Home Build Opportunity! Offered By Reputable Local Home Developer- Pioneer Builders Known For Building Numerous Custom Homes In Windermere, Winter Park, Downtown Orlando, And Winter Garden. Current Plans Reflect Under A/c 8,446 Sq Ft Consisting Of 4 Bedrooms, 5 Bathrooms, 4 Car Garage, Study, Wine/...

11940 Lake Butler Boulevard, WINDERMERE

New Photo of Listing #O5992327

$6,995,000

  • 5 Beds
  • 6 Baths
  • 1 Half

  • 6,549 SqFt
  • 2.41 Acres

Single Family Residence

Metcalf Park Rep

Unique Estate Home Set On 300 Feet Of Lake Butler Shoreline With 300’ Seawall. This Private, Gated Lakefront Home Is Set On 2.4 Acres In Old Windermere, With Over 6,500 Sf Heated And Over 10,600 Sf Covered And Under Roof; 5 Bedrooms, 6.5 Bathrooms, A Resort Style Pool Overlooking Serene Lake Butler. Calling All Car Collector And Boating Enthusiasts! This Home Has All Of Your Needs Covered With A 5-car Garage And 2-car Porte-cochere, Plus 500-gallon Fuel Tank And 1000-gallon Diesel Tank With Ability To Fuel On The Water Or In Your Motor Court...

11115 Bridge House Rd Road, WINDERMERE

New Photo of Listing #O6017345

$5,750,000

  • 5 Beds
  • 5 Baths
  • 4 Half

  • 7,506 SqFt
  • 1.85 Acres

Single Family Residence

Reserve At Lake Butler S...

Perfectly Sited On Lake Butler With 1.85 Acres Of Land In Renowned Lake Butler Sound. This Jones Clayton Custom Estate Presents Classic European Elegance Newly Painted Exterior And Interior. The Old World Brick Motor Court Leads To An Impressive Estate Surrounded By Manicured Lawns, Landscaped With Tropical Gardens And Towering Royal Palms. At The Entry, The Focus Is On Symmetry Of Design From The Slate Flooring With Marble Inlays To The Intricate Ceiling Details And Hand Crafted Spiral Staircase. The Tongue And Groove Ceiling And Stone Fire...

5092 Isleworth Country Club Drive, WINDERMERE

New Photo of Listing #O6024918

$4,500,000

  • 5 Beds
  • 4 Baths
  • 2 Half

  • 6,115 SqFt
  • 0.93 Acres

Single Family Residence

Isleworth

With A Fabulous Location Along The Front Nine Of Isleworth’s Renowned Championship Golf Course Overlooking Hole 6, This Expansive Estate Showcases More Than 6,100 Square Feet Of Living Space. Beautifully Updated And Maintained, The Residence Displays A Wealth Of Unique Appointments, Including Custom Ceilings, Travertine Floors With Tile Inlays And Beautifully Detailed Stone Columns. The Formal Living Room Features A Soaring Ceiling Of More Than 20 Feet And Direct Access To The Lanai Creating An Elegant, Light-filled Space With A Gorgeous C...

11947 Lake Butler Boulevard, WINDERMERE

New Photo of Listing #O6008885

$4,395,000

  • 6 Beds
  • 8 Baths

  • 9,400 SqFt
  • 1.20 Acres

Single Family Residence

Lake Butler Estates

Pre-construction. To Be Built. Stunning Energy Efficient Contemporary Estate Home With Location! Location! Location! Located On 1.2acre Lot On Lake Butler Boulevard In The Town Of Windermere With Water Views Of Lake Butler. Don’t Miss This Opportunity To For A Brand New Luxury Build Designed And Constructed By Supreme International Custom Home Builders. Solid Concrete Construction With Hollow Core Second Floor Slab, Eifs Stucco, Energy Efficient Windows, Level-5 Drywall, State Of The Art Technology Hub Smart Home Automation, Elevator, Dancin...

9720 Nearwater Place, WINDERMERE

New Photo of Listing #O6021846

$4,000,000

  • 4 Beds
  • 4 Baths
  • 2 Half

  • 6,252 SqFt
  • 2.54 Acres

Single Family Residence

Windermere Downs

Lakefront Living At Its Finest Can Be Found On The Shores Of Lake Down On The Famed Butler Chain Of Lakes At This 2.5 Acre Estate Boasting 4 En-suite Bedrooms, With The Possibility Of Converting A Flex Room To A 5th En-suite, Plus 2 Half Baths. The Circular Paver Driveway Leads To This Stunning Home Featuring A 4 Car Garage With An Air Conditioned Art Studio And A Recently Painted Exterior. This Outstanding Home Has Been Meticulously Cared For And Offers Contemporary Style Renovations, Hickory And Natural Stone Flooring, Plantation Shutters...

11835 Lake Butler Boulevard, WINDERMERE

New Photo of Listing #O5999414

$3,999,000

  • 6 Beds
  • 7 Baths
  • 1 Half

  • 7,500 SqFt
  • 1.00 Acres

Single Family Residence

Lake Butler Estates

One Or More Photo(s) Has Been Virtually Staged. Pre-construction. To Be Built. Coming Soon!! ---brand New Ultra Modern Home With Lake Views In Windermere. One Of A Kind Style !! This Is The Kind Of Home You Do Not Get To See That Often. The Kind Of Of Home Most People Only Get To See In Magazines!! For The Most Discerning Of Buyers Wanting It All. This Sophisticated 7500 Plus Square Feet Of Indoor Space And Over 10,000 Sq Ft Including The Outdoor Areas, Amazing! 6 Bedroom 7 Bath Home Captures The Beauty Of Florida Living With Its Lake Views ...

4066 Isabella Circle, WINDERMERE

New Photo of Listing #O6023352

$3,890,000

  • 6 Beds
  • 6 Baths
  • 2 Half

  • 7,327 SqFt
  • 0.87 Acres

Single Family Residence

Casabella Ph 2

Welcome To This Amazing Waterview House At Casabella. Offering Only 79 Single Family Homes, This Is A Luxury Gated Community In Upscale Windermere. The Villa Lago Floorplan Features A Stunning Two-story. Entering Your Front Doors You Have A Wonderful Living Room With Its Circular Coffered Ceiling And Spetacular Views Through Soaring Curved Windows. Oversized Chef's Delight Gourmet Kitchen With An Oversized Center Island Includes Stainless Appliances, Walk-in Pantry, Sunlit Breakfast Area And Wet Bar All Leading To Outdoor Leisure Time. This...

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 May 22nd, 2022 at 10:18am EDT.