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!

Search Windermere Real Estate Listings

All Listings $300,000 - $400,000 $400,000 - $500,000
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146 Properties Found. Showing Page 1 of 13
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9508 Windy Ridge Road, WINDERMERE

New Photo of Listing #O6060999

$30,000,000

  • 7 Beds
  • 14 Baths
  • 2 Half

  • 29,739 SqFt
  • 18.17 Acres

Single Family Residence

Acreage & Unrec

Perfectly Positioned On 18 Acres Of Lakefront Property With Meticulously Manicured Grounds, This Walled And Gated Compound Includes Apprx 614 Feet Of Pristine Lake Frontage And Panoramic Views On Lake Down Of The Butler Chain Of Lakes. The Options Available To Further Develop This Property Are Endless In Expanding/building More Structures, Various Ways To Subdivide, Parcel Into A Family Compound, Or Continue To Enjoy It As One Massive Private Gated Lakefront Estate As Utilized Currently. The Magnificent Sprawling Primary Residence Pairs Clas...

5020 Down Point Lane, WINDERMERE

New Photo of Listing #O6030119

$7,959,000

  • 8 Beds
  • 8 Baths

  • 9,621 SqFt
  • 2.01 Acres

Single Family Residence

Sunset Bay Rep

This Stunning Estate Is The Epitome Of Luxury Windermere Lakefront Living. Designed By Legendary Architect John Henry, This Exquisite Lakefront Residence 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 Six-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 L...

5139 Isleworth Country Club Drive, WINDERMERE

New Photo of Listing #O6026101

$7,900,000

  • 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 A Once In A Lifetime Opportunity Inspired By The Italian Renaissance. One Of The Most Exclusive Private Golf And Country Club Communities In The World Offers An Exquisite Location Within The Main Gates Of The Beautiful Award-winning Community Of Isleworth Golf And Country Club. A Fabulous Double Acre Location Along The Front Nine Of Isleworth’s Renowned Championship Golf Course Overlooking Hole #3. The Expansive Estate Showcases More Than 12,500 Square Feet Of Living Space. Beautifully Updated...

9832 Laurel Valley Drive, WINDERMERE

New Photo of Listing #O6043474

$7,775,000

  • 6 Beds
  • 7 Baths
  • 3 Half

  • 11,100 SqFt
  • 0.70 Acres

Single Family Residence

Isleworth

Stunning Water Views And **captivating Sunsets** Will Take Your Breath Away At This Exquisite Lakefront Estate. Perfectly Situated On The Shores Of Lake Butler And The 15th Hole Of Isleworth's Prestigious Championship Golf Course You Will Enjoy 150 Feet Of Lake Frontage Of The Famed Butler Chain Of Lakes. Inside, You Will See What Truly Elevates This Home. Distinctive Details, An Array Of Updated And Amazing Finishes And Three Magnificent Floors With Spaces For Everyone In The Family. On The Main Level: A Gracious Two-story Foyer O...

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. Land Purchase At 2.795m Or Pre-construction Home At 7.5m Rare, Exclusive Lakefront Property In Windermere, Florida. Front And Rear Water Views! Gated Community With Only Three Home Sites. Herein Lies An Opportunity Like No Other To Build Your Dream Home On 6.82 Acres Of Lakefront Property In Windermere, Fl. Shoreline Comprising 524 Feet Fronting Lake Down On The Butler Chain Of Lakes. The Space Directly South And Directly West Of The Water Feature Pond Presents Any Buyer With A Unique Opportunity To Incorpor...

6507 Rosella Court, WINDERMERE

New Photo of Listing #O6064654

$7,495,000

  • 6 Beds
  • 7 Baths
  • 1 Half

  • 10,485 SqFt
  • 2.19 Acres

Single Family Residence

Keenes Pointe 46/104

Windermere - Lakefront - Keenes Pointe - 24 Hr Guard Gated Community... Explore This Stonebridge Custom Homes, 6 Bedroom, 8 Bathroom Estate, Boasting More Than 10,000 Square Feet Of Resort Style Entertainment, Solitude, And An Abundance Of Luxury Finishes. As You Approach The Estate, Pause And Take In The Handcrafted Stonework And Manicured Grounds With Fountain And Beautiful Vines Reminiscent Of European Architecture. As You Enter The Grand Atrium You Will Be Drawn Into The Glass Wall Showcasing The Spectacular Florida Pines Along The...

11947 Lake Butler Boulevard, WINDERMERE

New Photo of Listing #O6065698

$7,035,000

  • 6 Beds
  • 6 Baths
  • 3 Half

  • 14,364 SqFt
  • 1.20 Acres

Single Family Residence

Lake Butler Estates

Pre-construction. To Be Built. Your Contemporary Work Of Art Awaits. Located In The Town Of Windermere On The Famed Lake Butler Blvd. Is A Beautiful 1.2-acre Plot Of Land Just Waiting For This Stunning Two-story Masterpiece. This Custom Estate Home Will Be Over 14,000 Sf Of Luxury Living And Entertaining, With Six Bedrooms, And Nine Bathrooms. There Will Be Three Primary Suites, With One Located On The First Floor And The Other Three Upstairs. Each Of The Bedrooms Will Have En-suite Bathrooms And Private Balconies. The Main Floor Primary Sui...

9838 Laurel Valley Drive, WINDERMERE

New Photo of Listing #O6060724

$7,000,000

  • 5 Beds
  • 6 Baths
  • 3 Half

  • 10,843 SqFt
  • 0.54 Acres

Single Family Residence

Isleworth

Majestic Lake Butler Lakefront, Sunset Views, Disney Fireworks And The 15th Hole Of Isleworth's Renowned Championship Golf Course. As Far As Location Goes, This Home Has It All. Breathtaking Staircases, Open Floor Plan And 2 Story, Direct Lake Views Throughout The Main Floor. This One Is A Must See

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...

11049 Bridge House Road, WINDERMERE

New Photo of Listing #O6033684

$5,995,000

  • 5 Beds
  • 5 Baths
  • 3 Half

  • 10,112 SqFt
  • 2.90 Acres

Single Family Residence

Reserve At Lake Butler S...

Exquisite Mediterranean Masterpiece, Located In The 24-hour Guard-gated Community Of Lake Butler Sound. This Stunning Residence Features Over 10,000 Square Feet Of Luxury Living Space And Is Perfectly Positioned Along The Shores Of Lake Butler On The Famed Butler Chain Of Lakes. This Privately Gated Compound Includes A Resort Pool With Rock Waterfalls, A Lazy River, Hot Tub, Summer Kitchen And An Outdoor Living Room With A Gas Fireplace. As You Step Through The Front Doors, Your Eyes Are Immediately Greeted By Soaring Two-story Ceilings And ...

801 West 2nd Avenue, WINDERMERE

New Photo of Listing #O6032540

$5,995,000

  • 5 Beds
  • 6 Baths

  • 5,639 SqFt
  • 1.09 Acres

Single Family Residence

Aladar On Lake Butler

Set Within One Of The Most Coveted Streets In All Of Windermere, Awaits An Incredibly Rare Opportunity For Your Enjoyment Of Living. This Unique Property Is Two Lots Combined Into One, Providing 1.09 Acres Of Dry Land On The Butler Chain Of Lakes With The Option To Add Significant Square Footage Onto The Existing Structure. Upon Entering The Existing Home, An Impressive Two-story Foyer And Formal Living Space Greet You And Invite You In. From The Very First Step Through The Front Door, You’ll Notice That You’re Standing On A Piece Of Art. A ...

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 December 9th, 2022 at 9:48pm EST.