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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44 Properties Found. Showing Page 1 of 4
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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.

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 #O5986780

$6,450,000

  • 5 Beds
  • 7 Baths
  • 2 Half

  • 10,112 SqFt
  • 2.90 Acres

Single Family Residence

Reserve At Lake Butler S...

Presenting A Custom-crafted Mediterranean Mansion Secluded Behind Its Own Private Gates, Perched Along The Shores Of Lake Butler, Inside Guard-gated Reserve At Lake Butler Sound. Unmistakable Elegance Abounds With Soaring Two-story Ceilings, Polished Travertine And Wood Floors, Arched Windows, Signature Precast Stone Gas Fireplace, Multiple Oversized French Doors, Coffered Ceilings, And Grand Details Throughout. Built To Impress By Master Craftsman Jim Akers, This Estate Residence Features 5 Bedroom Suites, 9 Bathrooms, Executive Office, A ...

6845 Valhalla Way, WINDERMERE

New Photo of Listing #O5988419

$3,499,000

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 7,438 SqFt
  • 0.50 Acres

Single Family Residence

Keenes Pointe 46/104

Keene's Pointe Stunning Estate Home Located On The 17th Fairway Of The Golden Bear Club Featuring Golf, Tennis, Fitness, Swimming And Dining. This Home Has It All. From The Moment You Enter Through The Beautiful Leaded Glass Doors, You Are Greeted With Quality From The Stone And Hardwood Floors To The Custom Features Throughout. Formal Living And Dining Rooms Set The Stage And Take You To Through The Wet Bar With Refrigeration And A Wine Cellar To The Well-appointed Kitchen With Large Walk-in Pantry, 2 Dishwashers, And Wolf And Subzero Ap...

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...

31 Pine Street, WINDERMERE

New Photo of Listing #O5989705

$2,750,000

  • 4 Beds
  • 3 Baths

  • 2,735 SqFt
  • 0.56 Acres

Single Family Residence

Windermere Town

Check Out Video Www.31pine.site/mls One Lucky Buyer Will Own One Of The Most Desirable Lake Front Lots On The Butler Chain. Boasting Well Over 500 Ft Of Your Own Private Shoreline On Lake Butler Set On One Of The Rare, Paved Streets In The Heart Of Downtown Windermere. A Short Walk And Even Shorter Golf Cart Ride To The Farmers Market, Food Truck Night And Of Course Allen's For Ice Cream. Quiet Tree Lined Dead End Street Of Pine Street Is One Of The Most Sought-after Streets To Call Home In The Entire 34786 Zip Code. Dream Back Yard With ...

4704 Joanna Garden Court, WINDERMERE

New Photo of Listing #O5983607

$2,750,000

  • 3 Beds
  • 3 Baths
  • 2 Half

  • 4,261 SqFt
  • 0.26 Acres

Single Family Residence

Isleworth

Nestled Within The Gardens Of Isleworth – An Intimate Enclave Of Custom Homes – This Beautiful Garden Estate Offers A Secluded Location Within The Gates Overlooking Beautiful Garden And Water Views. Built By Wyatt Anderson Construction, The Single-story Home Spans More Than 4,200 Square Feet And Has Been Beautifully Maintained. The Exterior Showcases Beautiful Mediterranean Style, With Wooden Garage And Arched Entry Doors, Pristine Tropical Landscaping, An Entry Courtyard With Fountain And A Lovely Turret. Exquisite Finishes Adorn The Int...

4333 Isabella Circle, WINDERMERE

New Photo of Listing #O5989445

$2,590,000

  • 6 Beds
  • 7 Baths

  • 6,857 SqFt
  • 0.65 Acres

Single Family Residence

Casabella

Your Dream Home Awaits! This Toll Brothers Executive Home Is Situated On A Generous 2/3 Acre Lot, Ample Parking, With A Magnificent Outdoor Entertainment Area. As You Enter The Home The Dramatic Ceiling And Natural Light Give The Home An Airy, Luxurious Feel. The Chef’s Kitchen Features Wolf Appliances, A Sub-zero Refrigerator, Along Its Extra-large Island. The Expansive Master Bedroom, Located On The First Floor, Includes A Separate Sitting Area Perfect For Your Home Gym Or Personal Library. Five Additional En-suite Bedrooms Make This Home ...

6119 Payne Stewart Drive, WINDERMERE

New Photo of Listing #O5974298

$2,500,000

  • 3 Beds
  • 3 Baths
  • 1 Half

  • 2,836 SqFt
  • 0.31 Acres

Single Family Residence

Isleworth

The Desired Golf Villas Of Isleworth Offer The Best In Country Club Living, Located Just Steps From The Famed Clubhouse And Renowned Butler Chain Of Lakes. Positioned Along The Shores Of Lake Chase, This Lakefront Golf Villa Offers An Exceptional Setting Within The Gates Of One Of The Finest Golf Club Communities In The World. Its Prime Location Directly Across From The Club Presents A Rare Opportunity For A Lakefront Property In Proximity To The Finest Amenities That The Community Has To Offer. The Interior Spans More Than 2,800 Square F...

2730 Midsummer Drive, WINDERMERE

New Photo of Listing #O5888668

$2,500,000

  • 4 Beds
  • 3 Baths
  • 1 Half

  • 3,452 SqFt
  • 2.78 Acres

Single Family Residence

Lake Down Shores Rep

The 2 Story Home Is In The Process Of A Major Renovation That Will Completely Revise The Floorplan And Cosmetic Finishes To Make The House Look Like It Was Built In 2022 - Welcome To 2730 Midsummer Drive In Windermere Florida On The Eastern Shores Of Lake Down 1 Of 13 Lakes In The Famed Butler Chain Of Lakes Receiving The Designation Of Outstanding Florida Waters From The Florida Department Of Environmental Protection In 1985 Because Of Its Water Quality And Wildlife Habitat - Midsummer Drive Is One Of The Most Charming Oak Canopy Covered Ro...

1324 Lake Olivia Ln, WINDERMERE

New Photo of Listing #O5997569

$2,495,000

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 5,222 SqFt
  • 1.19 Acres

Single Family Residence

Lake Olivia Reserve Rep

Welcome To Stunning Lakefront Living Within The Gated Community Of Lake Oliva Reserve. This Custom Home By Premium Builders, Generation Builders, Was Constructed In 2020 With Attention To Every Detail And Implementation Of The Finest Finishes. This 5200+ Sf Estate Has So Many Unique Features Such As 2 Master Suites, 1 Up And 1 Down, 2 Oversized 2 Car Garages Each With A Separate Mud Room Containing Built-in Storage For Shoes, Coats And Extra Storage, 2 Laundry Rooms, 1 Up And 1 Down, Cameras And A Ring Style Doorbell And More. This Home Is S...

2125 Water Key Drive, WINDERMERE

New Photo of Listing #O5965402

$2,395,000

  • 6 Beds
  • 7 Baths

  • 6,103 SqFt
  • 0.77 Acres

Single Family Residence

Reserve At Waterford Poi...

This Grand, One Of A Kind Home Has Had A Nearly Full Remodel Over The Last 2 Years Inside And Out! As You Pull Up To The Driveway You Will Immediately Notice The Updates And The Attention To Detail. Step Through The Front Door To Be Greeted With Gorgeous Views Straight Out To The Pool And Canal As Well As An Epic Hand Assembled Chandelier Over The Front Livingroom That Is Sure To Impress. Have A Chef Or Aspiring Chef In The Home? The Kitchen Has Updated Busby Cabinets, Upgraded Solid Surface Counter Tops And Fantastic Appliances That Are All...

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 20th, 2022 at 12:22am EST.