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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495 Properties Found. Showing Page 1 of 42
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9508 Windy Ridge Rd, Windermere

Photo of Listing #O5412382

$30,000,000

  • 6 Beds
  • 12 Baths
  • 2 Half

  • 51,000 SqFt
  • 18.00 Acres

Single Family / Villa

Acreage & Unrec

Private Windermere Lakefront Compound With 18 Acres On Lake Down On The Butler Chain Offering An Unparalleled Presence And Prestige In Central Florida’s Most Desirable Location. This Walled And Gated Compound Boasts A 25,000 Sqft. State-of-the-art Family Residence, A 5,600 Sqft Grand Lodge With Catering Kitchen And Large Entertainment Hall, A 4,000 Sqft Paneled Garage With 20 Ft. Ceilings For Car Collectors, A Separate Office With Guest Apartment, A 3,800 Sqft Storage Building With 20 Ft. Ceilings, Staff Quarters, And Massive 25 Meter Pool. ...

N/A, Windermere

Photo of Listing #O5498420

$18,950,000

  • 9 Beds
  • 13 Baths
  • 4 Half

  • 20,240 SqFt
  • 4.78 Acres

Single Family / Villa

Presenting Central Florida’s Most Exquisite Lake Butler Estate Tucked Behind The Secured Manned Gates Of Lake Butler Sound. Offering 20,240 Sq Ft Under Air (31,000 Gross), On Nearly 5 Acres And 547 Feet Of Lake Frontage, This Double-lot Oasis Offers A Magnificent Residence With Multiple Outdoor Living And Entertaining Areas, Private Guest Quarters, 8-car Garage, Lighted Tennis Court With Basketball, Sand Volleyball, Citrus Orchard, Zip Line, Children's Treehouse With Electricity, And A Resort Pool With Grotto And Swim Up Bar With Hibachi Gri...

5536 Isleworth Country Club Dr, Windermere

Photo of Listing #O5394385

$15,000,000

  • 7 Beds
  • 9 Baths
  • 1 Half

  • 13,519 SqFt
  • 1.89 Acres

Single Family / Villa

Isleworth

Poised On A Private Cul-de-sac Overlooking Isleworth’s 14th Fairway And The Beautiful Lake Butler, This Island-inspired Estate Spans Three Home Sites Totaling 1.89 Acres. The Sprawling Floor Plan Encompasses More Than 13,000 Square Feet Of Living Space, With Elegant Appointments Throughout. The Resplendent Interior Showcases Formal Living And Dining Rooms, Each Accented By Elegant Fireplaces And Chandeliers. Designed For Two Chefs, The Kitchen Features Three Islands, Two Jenn-air Stoves With Gas Cooktops And Three Sub-zero 700 Series Refri...

5115 Fairway Oaks Dr, Windermere

Price
Reduced
Photo of Listing #O5433535

$10,999,000

  • 7 Beds
  • 7 Baths
  • 4 Half

  • 15,063 SqFt
  • 3.76 Acres

Single Family / Villa

Isleworth

A Sprawling Floor Plan And A Prime Setting On 3.76 Acres Along The Shores Of Lake Bessie Define This Exquisite Seven-bedroom Residence. Through A Pair Of Arched French Doors With Glass And Iron Detail, The Foyer Opens To A Stunning Two-story Living Room Where Dramatic Floor-to Ceiling Windows Allow An Abundance Of Natural Light While Capturing The Stunning Water Views. A Wealth Of Unique Finishes Such As Imported Stone And Antique Details Travel Throughout The Master-designed Floor Plan, From The Formal Dining Room, Kitchen And Breakfast Are...

5318 Isleworth Country Club Dr, Windermere

Photo of Listing #O5441428

$8,500,000

  • 6 Beds
  • 8 Baths
  • 1 Half

  • 11,182 SqFt
  • 1.74 Acres

Single Family / Villa

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 11,000-square-foot Interior Of This Beautiful Estate. Built By Leading Custom Home Builder Pellegrini Homes, The Master-designed Floor Plan Draws Every ...

5354 Isleworth Country Club Dr, Windermere

Price
Reduced
Photo of Listing #O5405442

$7,225,000

  • 5 Beds
  • 6 Baths

  • 9,811 SqFt
  • 1.18 Acres

Single Family / Villa

Isleworth 01 Amd

Seller Requirement: Buyer Must Produce Proof Of Funds At Full Listing Price. Beautifully Mirrored In Hourglass Pond, This Home Was Designed To Reflect The Elegance Of An Old, Italian Villa Positioned On An Oversized Lot With More Than An Acre Of Lush, Manicured Gardens. Globally Sourced Materials, Including Medallions Of Ancient Terracotta, Marble And Granite Retrieved From The Same Vatican Quarries Outside Rome. Down The Brick-paver Driveway, Through The Honed-marble Framed Front Doors, You Are Welcomed By Jerusalem Limestone And A Sweeping...

5018 Latrobe Dr, Windermere

Photo of Listing #O5460974

$6,875,000

  • 7 Beds
  • 7 Baths
  • 3 Half

  • 12,353 SqFt
  • 0.67 Acres

Single Family / Villa

Isleworth

Gracious Living At Its Finest, This Exquisite French Chateau Offers A Prime Location Overlooking The Beautiful Lake Bessie Within The Renowned Isleworth Golf & Country Club. Elegant Finishes, Stonework And Extensive Marble Throughout Set The Tone For The Three-story Home Encompassing More Than 12,300 Square Feet Of Living Space. The Main Level Boasts A Beautiful Foyer With Grand Staircase And Opens To The Formal Living Room With Volume Ceilings, A Stone Fireplace And Breathtaking Water Views. The Spacious Kitchen Boasts A Warm Mix Of Cust...

N/A, Windermere

Price
Reduced
Photo of Listing #O5431648

$6,645,000

  • 6 Beds
  • 6 Baths
  • 3 Half

  • 11,163 SqFt
  • 0.97 Acres

Single Family / Villa

Seller Requirement: Buyer Must Produce Proof Of Funds At Full Listing Price. This Commanding Waterfront Residence Is Elegantly Situated On A Picturesque Home Site Along The Shores Of Beautiful Lake Bessie. The Six-bedroom Home Blends A Spanish Mediterranean Exterior With A Modern Transitional Interior, From The Grand Foyer, Great Room And Formal Dining Room To The Kitchen And Family Room. Comprising More Than 11,000 Square Feet, The Home Also Boasts Unique Hand-selected Finishes And Accompaniments Throughout. Highlights Include An Artisan-...

5306 Isleworth Country Club Dr, Windermere

Photo of Listing #O5469566

$5,795,000

  • 5 Beds
  • 5 Baths
  • 3 Half

  • 8,802 SqFt
  • 0.57 Acres

Single Family / Villa

Isleworth

Under Construction. Designed By Renowned Architect Terry Irwin And Currently Being Built By Leading Custom Homebuilder Wyatt Construction, This Two-story Estate Will Offer Five Bedrooms And More Than 8,800 Square Feet Of Living Space. Nestled Along The Back Nine Within The Gates Of The Renowned Isleworth Golf & Country Club, The Estate Will Afford Beautiful Finishes And Living Spaces Set Against A Backdrop Of Multiple Golf And Water Views, Including Eagle Pond And Holes 11 And 12.

9832 Laurel Valley Dr, Windermere

Photo of Listing #O5510614

$5,750,000

  • 6 Beds
  • 7 Baths
  • 3 Half

  • 11,100 SqFt
  • 0.60 Acres

Single Family / Villa

Isleworth

Unparalleled Isleworth Estate With Amazing Views Of Lake Butler Combined With Direct Golf Course Frontage On Iselworth’s 15th Hole. This One Of A Kind Three Story Home Is Perched High Above The Famed Butler Chain Of Lakes Offering Incredible Water Views. Featuring 6 Bedroom Suites, A Movie Theater, Game Room/casino, Personal Elevator, Wine Cellar, Fitness Room, Play Room, Private Generator, And Two Offices, This House Has Something For Everyone. The Minute You Walk Through The Front Doors Your Eyes Are Immediately Drawn To The Soaring Two St...

9711 Deacon Ct, Windermere

Photo of Listing #O5514968

$5,650,000

  • 5 Beds
  • 3 Baths
  • 3 Half

  • 8,400 SqFt
  • 1.16 Acres

Single Family / Villa

Isleworth

Lakefront Isleworth Estate, 400' Shoreline On Lake Isleworth, 1 Of 11 Lakes On The 6,500 Acre Famed Butler Chain Of Lakes Connected By Canals, Panoramic Sunset Views, 1.16 Acre Property, Infinity Edge Pool & Spa With Marble Fountains & Accents, Expansive Terraces With Italian Chiseled Marble, Fountains, Concrete Seawall, Tuscan Design With Imported Italian Marble Fireplace Mantles, Hand Chiseled Marble Floors Throughout, Inlaid Cistene Inspired Tiles, Hand Textured Walls & Ceilings, Crown Moldings, Gourmet Chef's Kitchen With Hand Carved Ita...

5300 Isleworth Country Club Dr, Windermere

Photo of Listing #O5469557

$5,495,000

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 8,162 SqFt
  • 0.51 Acres

Single Family / Villa

Isleworth

Under Construction. Offering A Prime Location Within The Gates Of The Renowned Isleworth Golf & Country Club, This Two-story Estate Will Feature Magnificent Views Of Holes 11 And 12, As Well As Eagle Pond And Open Land Showcasing One Of Isleworth’s Exquisite Sculptures. Designed By Renowned Architect Terry Irwin And Currently Being Built By Leading Custom Homebuilder Wyatt Construction, The Five-bedroom Home Will Encompass More Than 8,100 Square Feet Of Living Space, With Elegant Finishes Such As Hardwood Floors And Barrel Ceilings Through...

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.

Browse Windermere Communities:

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.

Listing information last updated on June 26th, 2017 at 9:51am EDT.