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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176 Properties Found. Showing Page 1 of 15
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9508 Windy Ridge Road, WINDERMERE

New Photo of Listing #O5890318

$30,000,000

  • 6 Beds
  • 12 Baths
  • 2 Half

  • 51,000 SqFt
  • 18.16 Acres

Single Family Residence

N/a

This 18-acre Private Walled And Gated Compound Is One Of The Most Exceptional Properties In Central Florida, Unrivaled By Its Sheer Size, Ideal Shape, Remarkable Topography And High Elevation. The Property Offers Over 600 Feet Of Unobstructed Views And Access To One Of Lake Bulter's Cleanest Lakes. The Unparalleled Location Provides The Privacy And Tranquility Of Living "amongst The Lakes" In Windermere Without The Hassle Of Long Commutes Through The Local Routes. The Stately Residence Offers The Perfect Combination Of Warmth And Tradition U...

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

  • 5 Beds
  • 4 Baths
  • 4 Half

  • 12,778 SqFt
  • 2.04 Acres

Single Family Residence

Isleworth 7th Amd

Under Construction. 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 The Stage For This One-of-a Kind Estate With A Skybox That Overlooks The In...

5372 Isleworth Country Club Drive, WINDERMERE

New Photo of Listing #O5834063

$7,400,000

  • 8 Beds
  • 7 Baths
  • 2 Half

  • 13,230 SqFt
  • 1.03 Acres

Single Family Residence

Isleworth

Auction Property. This Breathtaking Estate Located Within The Main Gates Of Isleworth Golf & Country Club Is The Perfect Place To Work And Play. Spacious And Striking, Its Mediterranean Exterior And French Renaissance Interior Impress From First Look. Step Past The Lush Tropical Greenery Of The Well-established Gardens And Through The Home’s Elegant Front Doors. The Home’s Entry Sets An Appropriately Impressive Tone With Its Soaring Two-story Vaulted Ceiling, Grand Staircase, And Custom Rock Waterfall. Entertain In Its Many Living Spaces, In...

5318 Isleworth Country Club Drive, WINDERMERE

New Photo of Listing #O5872952

$6,600,000

  • 6 Beds
  • 8 Baths
  • 2 Half

  • 12,298 SqFt
  • 1.74 Acres

Single Family Residence

Isleworth

Motivated Seller! Your Offer May Buy This Stunning Golf-front Estate In Isleworth - Seller Considering All Offers! Dramatic Interior Includes An Interior Custom Designed, Temperature-controlled, Grand 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 Stunning Interior! Imagine Entertaining Your Guests Or Clients In This Pavilion,with The Moonlight Streaming Through The Skylights And The Soft Lights Of Th...

11055 Bridge House Road, WINDERMERE

New Photo of Listing #O5903029

$6,400,000

  • 6 Beds
  • 6 Baths
  • 3 Half

  • 10,452 SqFt
  • 2.48 Acres

Single Family Residence

Reserve At Lake Butler S...

Waterfront Masterpiece On The Famed Butler Chain Of Lakes! Showcasing Grand Scale Living Spaces, Unprecedented Finishes And Resort-style Grounds, This Privately Gated Rial Jones Estate Captivates At Every Turn. Featuring Over 10,000 Square Feet Of Exquisitely Appointed Interior Living Space, On Over Two Acres With Panoramic Views Of The Famed Lake Butler, This Artfully Renovated Residence Provides You With A Unique Opportunity To Live Your Dream, Without Ever Leaving The Serenity Of Your Home. Enchanting Lake Views And Spacious Indoor-outdoo...

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...

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...

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...

12624 Park Avenue, WINDERMERE

New Photo of Listing #O5868103

$4,623,000

  • 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...

11217 Bridge House Road, WINDERMERE

New Photo of Listing #O5914180

$3,990,000

  • 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 ...

6025 Greatwater Drive, WINDERMERE

New Photo of Listing #O5877250

$3,889,000

  • 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 January 22nd, 2021 at 9:10pm EST.