Below you can view all the homes for sale in the Windermere subdivision located in Windermere Florida. Listings in Windermere are updated daily from data we receive from the Orlando multiple listing service.

To learn more about any of these homes or to receive custom notifications when a new property is listed for sale in Windermere, give us a call at 407-278-2057.

47 Results

Windermere Windermere Florida Homes For Sale

Windermere For Sale $2,650,000

View 1003 Oakdale St Windermere FL
View 1003 Oakdale St Windermere FL
View 1003 Oakdale St Windermere FL
On Market For 2 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4061

  • Year Built

    2003

  • $/SqFt

    $653

If You Have Dreamed of Having a Home Where Family and Friends want to Hang Out and Spend Quality Time Building Lifetime Friendships and Cherished Memories then I have the Place You Need to See - Peace and Tranquilty are found under the towering Spanish Moss covered Oaks in your spacious back yard with mature hedges, flowering Azaleas and Roses with a carpet of St. Augustine grass leading down to over 80 feet of white sand beach on crystal clear Lake Bessie in the heart of Windermere that feels like the "Old Florida" so many wish they could find - The Boathouse has a covered lift for the Wakeboard or Skiing crowd - The covered sitting area provides plenty of shade while catching the Trophy Bass Lake Bessie is famous for and the uncovered deck area is perfect for getting more Vitamin D - The Custom Built Home has 5 Bedrooms and a large Bonus Room with full bath over the 3 Car Garage offering plenty of places for Slumber parties or large families to spread out - The Screened in Pool is a fantastic place to enjoy the Sunrise with a cup of your favorite brew - The Family Room with Floor to Ceiling Stone Fireplace, Breakfast Nook and Gourmet Kitchen with top of the line Sub Zero & Wolf Gas Appliances have stunning views of the Lake and Pool - The 2nd floor 4th Bedroom overlooks the backyard, Lake and Pool and has a large Balcony with screened in sitting area that provides another great place to relax - From the moment you enter through the 10 foot tall Custom Handcrafted Iron Doors and see the Formal Dining Room, Formal Living Room, Stacked Stone Wine Cellar with Custom Iron Gate, Custom Handcrafted Iron Stair Railing, Butler's Pantry/Wet Bar all boasting timeless Travertine Flooring You will be impressed with the Quality of this Home - Primary Suite has Dual Vanities, Cosmetic Station, Large Walk In Closet and Lake & Pool views - The Town of Windermere has Coffee & Ice Cream Shops, Restaurants & a Brewery within walking distance - There are so many Custom Features in this home and wonderful places to see in Town so book your appointment now MLS#O6116062. VINTAGE REALTY GROUP LLC.

Windermere For Sale $539,000

View 11601 Black Rail St Windermere FL
View 11601 Black Rail St Windermere FL
View 11601 Black Rail St Windermere FL
On Market For 2 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2139

  • Year Built

    2012

  • $/SqFt

    $252

The community features a pool, playground, and dog park. MLS#O6114872. SUZI KARR REALTY.

Windermere For Sale $515,000

View 12875 Holdenbury Ln Windermere FL
View 12875 Holdenbury Ln Windermere FL
View 12875 Holdenbury Ln Windermere FL
On Market For 3 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2094

  • Year Built

    2006

  • $/SqFt

    $246

Close to University Studio and Disneyland. MLS#A4571778. KEYS REALTY REDEFINED LLC.

Windermere For Sale $1,649,000

View 1214 Estancia Woods Loop Windermere FL
View 1214 Estancia Woods Loop Windermere FL
View 1214 Estancia Woods Loop Windermere FL
On Market For 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4396

  • Year Built

    2019

  • $/SqFt

    $375

Residents of the town of Windermere also enjoy access to multiple parks, playgrounds, Tennis courts and keyed private access to a Butler Chain boat ramp. MLS#O6115413. COMPASS FLORIDA, LLC.

Windermere For Sale $810,000

On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3677

  • Year Built

    2017

  • $/SqFt

    $220

Imagine the joy and wonder of being able to share this magical experience with family and friends on special occasions or simply as a regular part of your life. MLS#S5085969. LPT REALTY, LLC.

Windermere For Sale $1,200,000

On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2106

  • Year Built

    2015

  • $/SqFt

    $570

Please note, some furniture may be purchased with the home. MLS#U8202185. EXP REALTY, LLC.

Windermere For Sale $424,500

On Market For 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1429

  • Year Built

    2006

  • $/SqFt

    $297

Nice townhome in great area with two car garage and enclosed courtyard. MLS#O6115067. ORLANDO'S BEST REAL ESTATE INC.

Windermere For Sale $399,900

On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1442

  • Year Built

    2006

  • $/SqFt

    $277

Porch with pool view, 2 parking spaces per unit, 24-hour security, large pool, beach volleyball court, picnic area with grills, fitness center and recreation building with pool table and TV. MLS#O6114124. TWIN HOMES REALTY.

Windermere For Sale $929,000

On Market For 41 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3082

  • Year Built

    1960

  • $/SqFt

    $301

(NOTE: Light fixture above dining table does not convey.) MLS#O6112996. BHHS FLORIDA REALTY.

Windermere For Sale $999,800

*POTENTIAL GREAT VALUE
On Market For 20 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    4936

  • Year Built

    2014

  • $/SqFt

    $203

Using showing button get the code. MLS#T3446585. PINEYWOODS REALTY LLC.

Windermere Pended $489,000

On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1797

  • Year Built

    2015

  • $/SqFt

    $272

Great shopping and fine dining just a mile away, top rated schools just a block away. MLS#O6109589. ELITE INTERNATIONAL REALTY.

Windermere For Sale $1,780,000

On Market For 26 Days
  • Bedrooms

    8

  • Full Bath(s)

    5

  • Sq. Ft.

    4751

  • Year Built

    2012

  • $/SqFt

    $375

Windermere is a great place to live, surrounded by a diversity of lakes, great schools, shopping malls, gym and all conveniences of a great town. MLS#O6109399. GRINDSTONE REALTY & PROPERTY MANAGEMENT LLC.

Windermere For Sale $3,400,000

On Market For 29 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    3660

  • Year Built

    1928

  • $/SqFt

    $929

This turn of the Century Classic Craftsman has more character and charm than anything on the market I have seen - Most homes this age would be considered "Tear Downs" but the bones are solid, Electrical and Plumbing upgraded, Ceilings are tall, Kitchen and Breakfast Nook are spacious - The property is wide enough to have a 1st Floor Master Suite & 1st Floor Guest Suite added on the right side and a 3 Car Garage added on the left side with entrance to the Kitchen and Dining areas to properly balance the home and make it a 5 Bedroom 4 1/2 Bath with a fantastic Flooplan - Call for details and proposed floorplans - The views of Lake Butler and the Disney fireworks are spectacular from most of the rooms in the house - The home has 3 Fireplaces, Living Room, Bedroom and the Rear Porch - The wrap around covered porch overlooking the lake will become the place everyone wants to hang out - New Boat Dock with covered sitting area, Pontoon Port and Jet Ski, Kayak or Paddle Board lift gives you immediate access to The Butler Chain of Lakes considered one of Florida’s Outstanding Waterways consisting of 11 interconnecting freshwater lakes and the regions best fishing - Gas Generator to make sure you have power at all times - The Town of Windermere has a small town feel with a Town Hall and large courtyard where many special events are scheduled throughout the year - 2nd Avenue is a paved road and walking distance to the Weekly Farmer's Market, Library, Ice Cream & Coffee Shops, Dixie Cafe', Windermere Brewery and by car it is only minutes from fine dining, premium shopping, numerous golf courses and all area theme parks & attractions - This is a must see property that has not been for sale in over 60 years - Crystal Clear Water & White Sand Beach MLS#O6109410. VINTAGE REALTY GROUP LLC.

Windermere Pended $545,000

On Market For 2 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2269

  • Year Built

    2002

  • $/SqFt

    $240

Minutes to Dr Phillips, Disney, Shopping, "A" rated WINDERMERE Schools, and Fine Dining! MLS#O6106216. EXP REALTY LLC.

Windermere For Sale $3,450,000

Reduced By $175,000

On Market For 32 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5639

  • Year Built

    1999

  • $/SqFt

    $612

All the work has been done for you....come begin living your dream today! MLS#O6107116. LAKESIDE REALTY WINDERMERE INC.

Windermere Pended $1,100,000

*POTENTIAL GREAT VALUE
On Market For 25 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    4502

  • Year Built

    2015

  • $/SqFt

    $244

Call now to schedule your exclusive showing and make this your new home or vacation home. MLS#O6107482. ICONNECT REAL ESTATE.

Windermere For Sale $579,000

Reduced By $6,000

On Market For 38 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1853

  • Year Built

    2014

  • $/SqFt

    $312

In the heart of Windermere, cozy and elegant at the same time. MLS#O6107918. FLORIDA CONNEXION PROPERTIES.

Windermere For Sale $729,000

Reduced By $26,000

On Market For 38 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2911

  • Year Built

    2015

  • $/SqFt

    $250

Known for their energy efficient features, our homes help you live a healthier and quieter lifestyle while saving you thousands of dollars on your utility bills. MLS#S5084232. SUNSHINE FLORIDA REALTY, INC.

Windermere Pended $1,950,000

On Market For 10 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3383

  • Year Built

    1917

  • $/SqFt

    $576

Enjoy weekly Farmer’s Markets and seasonal Town events. Florida living at its finest! ! MLS#O6105352. UPSIDE REAL ESTATE INC.

Windermere Pended $800,000

*POTENTIAL GREAT VALUE
On Market For 3 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3907

  • Year Built

    2015

  • $/SqFt

    $205

Schedule a showing today and experience the ultimate in Florida living on this corner lot with a versatile flex room, large pantry, and backyard oasis! MLS#O6105571. WRA BUSINESS & REAL ESTATE.

Windermere Pended $686,000

On Market For 19 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2224

  • Year Built

    2018

  • $/SqFt

    $308

Close to Hamlin Town Center, Cinepolis Cinema, Restaurants, Golf Courses, and Winer Garden Shopping Village MLS#O6105508. COLDWELL BANKER REALTY.

Windermere Pended $900,000

On Market For 28 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2690

  • Year Built

    2018

  • $/SqFt

    $335

Schedule your showing today! NO CDD! MLS#O6104961. RE/MAX PRIME PROPERTIES.

Windermere For Sale $490,000

On Market For 48 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1480

  • Year Built

    2005

  • $/SqFt

    $331

Very Lovely Townhouse In The Heart Of The One State's Best Locations And In Very High Demand Community, It's Known For It's Family Environment And Neighborly Appearance, This Beautiful 3 Bedroom Townhouse Has A Very Spacious And Bright Living Areas, Stainless Steel Appliances With 4 Door Refrigerator, Laminated Wood Flooring In The First Floor, Ceiling Chandeliers Lamps, Top-rated A+ Schools, Convenient Location In A Very Desired Community Conveniently Located Near Theme Parks, Shopping Center, And Restaurants. MLS#O6104984. GARDEN VIEWS REALTY LLC.

Windermere For Sale $919,000

Reduced By $231,000

On Market For 47 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1908

  • Year Built

    1978

  • $/SqFt

    $482

Don't miss the opportunity to make this lovely home your own. Schedule a showing today! MLS#O6098599. REGENCY REAL ESTATE LLC.

Windermere For Sale $600,000

On Market For 46 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2460

  • Year Built

    2005

  • $/SqFt

    $244

Don't miss your chance to make this beautiful home yours! MLS#O6105253. BUYER REBATES REALTY.

Windermere For Sale $1,049,500

Reduced By $65,500

On Market For 53 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2684

  • Year Built

    2020

  • $/SqFt

    $391

Copy and paste this link for a 3-D tour. https://my.matterport.com/show/?m=FjV6nu MLS#O6103778. PREMIER SOTHEBYS INT'L REALTY.

Windermere For Sale $495,000

On Market For 55 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1997

  • Year Built

    2016

  • $/SqFt

    $248

Don't miss this opportunity. Schedule a showing today. MLS#O6101835. MAYOLET REALTY LLC.

Windermere Pended $3,499,000

On Market For 24 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    7085

  • Year Built

    2020

  • $/SqFt

    $494

The tranquil sound of your private water wall with a backdrop of 2 large gas fire bowls will set the scene of your gorgeous private oasis...View our 3D Matterport tour link or schedule your private tour today to view this unique modern offering. MLS#O6102584. JULIAN PROPERTIES, INC..

Windermere For Sale $469,000

On Market For 56 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1812

  • Year Built

    2015

  • $/SqFt

    $259

Don't hesitate, schedule a showing today! MLS#O6102504. WRA BUSINESS & REAL ESTATE.

Windermere Pended $850,000

Reduced By $25,000

On Market For 58 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3260

  • Year Built

    2020

  • $/SqFt

    $261

Take advantage of this rare opportunity to live in the model home of this highly sought community! Schedule your showing today! MLS#O6101644. AGENT TRUST REALTY CORPORATION.

Windermere For Sale $359,900

On Market For 68 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1375

  • Year Built

    2005

  • $/SqFt

    $262

Conveniently located near Disney, shopping areas, schools, restaurants and much more! MLS#O6101128. VACASA FLORIDA LLC.

Windermere Pended $899,900

On Market For 60 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3062

  • Year Built

    1989

  • $/SqFt

    $294

This home is move-in ready and has been beautifully updated throughout, including a brand new roof! MLS#O6100577. CORCORAN PREMIER REALTY.

Windermere Pended $575,000

On Market For 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2452

  • Year Built

    2015

  • $/SqFt

    $235

This opportunity is too good to be missed out! MLS#S5082030. VACASA FLORIDA, LLC.

Windermere Pended $1,499,000

Reduced By $51,000

On Market For 43 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3493

  • Year Built

    2017

  • $/SqFt

    $429

Call today for your private showing. MLS#O6094047. RE/MAX PROPERTIES SW.

Windermere Pended $1,108,000

Reduced By $41,000

On Market For 60 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3407

  • Year Built

    2013

  • $/SqFt

    $325

Come and see it for yourself this SPECTACULAR LIKE NEW home! Video available: https://studio.youtube.com/video/5VAAwdBWtQA/edit MLS#O6090884. COMPASS FLORIDA, LLC.

Windermere For Sale $1,550,000

Reduced By $145,000

On Market For 110 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3746

  • Year Built

    2003

  • $/SqFt

    $414

Don't miss your opportunity to make this incredible home yours! MLS#O6088305. COLDWELL BANKER REALTY.

Windermere For Sale $359,000

Reduced By $16,000

On Market For 115 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1332

  • Year Built

    2006

  • $/SqFt

    $270

For the Disney fan the parks are within a short distance and you can even hear the nightly fireworks. MLS#S5080647. MAXIM REALTY ORLANDO.

Windermere Pended $370,000

On Market For 110 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1332

  • Year Built

    2006

  • $/SqFt

    $278

Enjoy the views from your backyard while watching the nightly Disney fireworks. MLS#S5080393. TOP REAL GROUP.

Windermere Pended $580,000

*POTENTIAL GREAT VALUE
On Market For 98 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2583

  • Year Built

    2015

  • $/SqFt

    $225

Upstairs features include a private laundry room, to easily access and keep your laundry tidy and organized. MLS#O6087807. THE FLORIDA LOUNGE REALTY LLC.

Windermere For Sale $1,698,500

Reduced By $16,500

On Market For 124 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    4069

  • Year Built

    2017

  • $/SqFt

    $417

MLS#O6087514. WATSON REALTY CORP., REALTORS.

Windermere Pended $625,000

Reduced By $24,000

*POTENTIAL GREAT VALUE
On Market For 134 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3000

  • Year Built

    2007

  • $/SqFt

    $208

Bring your most demanding buyer, they will not be disappointed! MLS#O6082615. COLDWELL BANKER REALTY.

Windermere For Sale $4,500,000

On Market For 164 Days
  • Bedrooms

    7

  • Full Bath(s)

    10

  • Sq. Ft.

    5735

  • Year Built

    2019

  • $/SqFt

    $785

Don't miss this opportunity to own this gorgeous home in Windermere. MLS#O6079340. STOCKWORTH REALTY GROUP.

Windermere Pended $2,200,000

On Market For 191 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4563

  • Year Built

    2023

  • $/SqFt

    $482

Lush landscaping and spacious 3-car garage. Do Not Miss This Opportunity. MLS#O6066584. STIRLING INTERNATIONAL REAL ES.

Windermere Pended $515,000

Reduced By $34,000

On Market For 283 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2066

  • Year Built

    2014

  • $/SqFt

    $249

**Owner is giving a credit for the buyer to replace the carpet upstairs** MLS#O6039774. PREMIER SOTHEBYS INT'L REALTY.

Windermere Pended $2,650,000

On Market For 58 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4758

  • Year Built

    2023

  • $/SqFt

    $557

If you are looking for a beautiful custom, now is the time to act as we only have 2 opportunities remaining. MLS#O6024757. CORCORAN PREMIER REALTY.

Windermere For Sale $2,875,000

On Market For 688 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5160

  • Year Built

    2021

  • $/SqFt

    $557

This home was made to create memories with your loved ones! MLS#O5959024. CORCORAN PREMIER REALTY.

Windermere Pended $2,542,000

On Market For 274 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4956

  • Year Built

    2021

  • $/SqFt

    $513

Close to A-rated schools, parks, farmers market, golf courses, restaurants, amenities and shopping, Disney World and Universal Studios. MLS#O5956997. CORCORAN PREMIER REALTY.

  • 1
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