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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321 Properties Found. Showing Page 1 of 27
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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...

5318 Isleworth Country Club Dr, Windermere

Price
Reduced
Photo of Listing #O5713515

$6,750,000

  • 6 Beds
  • 8 Baths
  • 2 Half

  • 12,298 SqFt
  • 1.74 Acres

Single Family Residence

Isleworth

Characterized By A Lovely English Garden Designed To Maximize Its Prime Golf-front Location, This Estate Is Unparalleled In Isleworth. Beyond The Circular Driveway With Fountain And Porte Cochere Entry, A Pair Of French Doors Open To The Grand Foyer Featuring A Curved Staircase, Wine Cellar And Polished Marble Floors With An Intricate Medallion Inlay—all Leading Graciously Into The More Than 12,000-square-foot Interior Of This Beautiful Estate. Built By Leading Custom Homebuilder Pellegrini Homes, The Master-designed Floor Plan Draws Every R...

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...

6126 Kirkstone Ln, Windermere

Photo of Listing #OM602024

$4,999,995

  • 5 Beds
  • 6 Baths
  • 1 Half

  • 8,379 SqFt
  • 1.42 Acres

Single Family Residence

Reserve At Lake Butler S...

Perfectly Sited Along The Shores Of The Coveted Lake Butler, This Exquisite Home (built By Renowned Builder, Wyatt Anderson) Has Amazing Sunsets In The 24 Hour Guard Gated Community Of The Reserve At Lake Butler Sound. This Grand Estate Has Been Substantially Upgraded, As Well As A New Large Addition, And Makes A Spectacular First Impression With The Elegant Fountain In Front Of The Circular Driveway, The Manicured Lawns And The Homes Expansive Presence On A 1.42 Acre Corner Lot. Upon Entering The Home You Will Notice The Impressive Custom T...

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 ...

5139 Fairway Oaks Dr, Windermere

Price
Reduced
Photo of Listing #O5775789

$4,745,000

  • 6 Beds
  • 6 Baths
  • 3 Half

  • 11,163 SqFt
  • 0.97 Acres

Single Family Residence

Isleworth

Seller Requirement: Buyer Must Produce Proof Of Funds At Full Listing Price. Nestled On A Picturesque Home Site Along The Shores Of Lake Bessie, This Commanding Waterfront Residence Blends A Spanish Mediterranean Exterior With A Modern Transitional Interior. Spanning More Than 11,000 Square Feet, The Six-bedroom Estate Boasts Unique Hand-selected Finishes And Accompaniments At Every Turn, From The Grand Foyer And Gallery Entry To The Open Great Room With Soaring Ceiling, Custom Fireplace, Grand Staircase And Floor-to-ceiling Windows Framing ...

5501 Isleworth Country Club Dr, Windermere

Photo of Listing #O5836176

$3,990,000

  • 6 Beds
  • 6 Baths
  • 2 Half

  • 6,956 SqFt
  • 0.87 Acres

Single Family Residence

Isleworth

Perfectly Sited On Just Under One Acre On The 14th Hole Of Renowned Isleworth Golf And Country Club This Transitional Style Estate Presents A 21st Century Translation;completely Renovated In 2017. The Residence Opens Up At The Foyer Visually Connecting Interior Spaces With Dramatic Results. The Focus Is On Symmetry Of Design From The Stunning Walnut Floors To The Elegant Designer Finishes. Abundant Natural Light In The Grand Room Adds A Sense Of The Outdoors And Activates The Openness Of The Plan. The Thoroughly New Modern Kitchen Feature...

6300 Deacon Cir, Windermere

Price
Reduced
Photo of Listing #O5825962

$3,750,000

  • 4 Beds
  • 5 Baths
  • 1 Half

  • 6,498 SqFt
  • 0.83 Acres

Single Family Residence

Isleworth

Welcome To One Of The Most Exquisite Lakefront Estates Within The Main Gates Of Isleworth. Just A Short Distance From The Prestigious Isleworth Golf & Country Club You Will Find An Architecturally Distinctive Masterpiece That Has Never Been Available On The Market Until Now. The Custom Residence Took Over Two Years To Construct Using The Highest Quality Materials Combining European Architecture With New World Luxury & Style. The Foyer Leads To A Herculaneum Inspired Loggia Adorned With Marble, Fountains, And Skylights Flanked By Columns. The...

6019 Greatwater Dr, Windermere

Price
Reduced
Photo of Listing #O5785371

$3,695,000

  • 6 Beds
  • 6 Baths
  • 2 Half

  • 7,415 SqFt
  • 2.79 Acres

Single Family Residence

Keenes Pointe

***virtual Open House- Https://www.youtube.com/embed/ow5-fk14qv0*** Fall In Love With Lakefront Living! Be Romanced By Classic European Architecture And Historical Charm That Sweeps You Away To Your Private Retreat On The Lake! Follow The Stone And Brick Pathway Past The Butterfly Garden And English Cast Stone Benches To An Enormous Mahogany Front Door That Welcomes You With A Solid Brass Lion Head Knocker! Come In And Enjoy The 6br, 6full Baths/2 Half Baths, Along With All The Formal And Casual Spaces You Could Want. Built By Akers...

11443 Waterstone Loop Dr, Windermere

Price
Reduced
Photo of Listing #O5785472

$3,675,000

  • 7 Beds
  • 7 Baths
  • 1 Half

  • 7,734 SqFt
  • 2.70 Acres

Single Family Residence

Waterstone

Windermere Luxurious Lakefront Living At It’s Best! This Grand Estate Built In 2014 Is Perfectly Sited Along The Shores Of Lake Butler With Unparalleled And Unobstructed Water Views In The Guard Gated Community Of Waterstone. Professionally Designed By Masterpiece Design Group, This Transitional Home Makes A Spectacular First Impression With Sweeping Picturesque Lake Views From Almost Every Angle And An Open Floor Plan For Entertaining. The Interior Boasts Over 7,730 Sq Ft Of Luxurious Living Space With 7 Bedroom Suites, 7.5 Baths, Office, ...

8304 Lake Burden Cir, Windermere

Photo of Listing #O5807082

$3,649,000

  • 8 Beds
  • 9 Baths
  • 1 Half

  • 8,808 SqFt
  • 0.57 Acres

Single Family Residence

Keenes Pointe Unit 2

Priced Below Appraisal. 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, Fitness Room, 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 Outd...

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 June 1st, 2020 at 6:45pm EDT.