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Isleworth Windermere Florida Homes For Sale

Below you can view all the homes for sale in the Isleworth subdivision located in Windermere Florida. Listings in Isleworth 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 Isleworth, give us a call at 407-278-2057.

Isleworth | For Sale

$1,300,000

View 6126 Payne Stewart Dr Windermere FL
View 6126 Payne Stewart Dr Windermere FL
View 6126 Payne Stewart Dr Windermere FL
Listed For 3 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2848

  • Year Built

    1989

  • $/SqFt

    $456

The outdoor living area invites sunbathing and relaxation in a garden-style setting year round with Central Florida’s tropical climate. MLS#O5744772. Isleworth Realty Llc. MFR

Isleworth | For Sale

$1,289,000

View 5114 Fairway Oaks Dr Windermere FL
View 5114 Fairway Oaks Dr Windermere FL
View 5114 Fairway Oaks Dr Windermere FL
Listed For 26 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6459

  • Year Built

    1999

  • $/SqFt

    $199

Take advantage of this opportunity to live in Isleworth. MLS#O5510531. Carrington Real Estate Service. MFR

Isleworth | For Sale

$5,295,000

View 5501 Isleworth Country Club Dr Windermere FL
View 5501 Isleworth Country Club Dr Windermere FL
View 5501 Isleworth Country Club Dr Windermere FL
Listed For 33 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6956

  • Year Built

    2007

  • $/SqFt

    $761

There is a whole house generator so you will never be without power... a very unique, and special property ....waiting for you to move in!!! ! MLS#O5740376. Irwin Realty Group Llc. MFR

Isleworth | For Sale

$1,395,000

View 5181 Latrobe Dr Windermere FL
View 5181 Latrobe Dr Windermere FL
View 5181 Latrobe Dr Windermere FL
Listed For 36 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3645

  • Year Built

    1996

  • $/SqFt

    $382

This house has it all!!!! Just waiting for you! MLS#O5740042. Irwin Realty Group Llc. MFR

Isleworth | For Sale

$1,695,000

Listed For 44 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4186

  • Year Built

    1993

  • $/SqFt

    $404

Fully equipped with a refreshing saltwater pool, spa and custom putting green, this elegant Isleworth estate is a golfer’s dream. MLS#O5737878. Isleworth Realty Llc. MFR

Isleworth | For Sale

$2,100,000

Listed For 45 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4426

  • Year Built

    1995

  • $/SqFt

    $474

The home also features a three-car garage and full-home automation that can be accessed from your phone or tablet. MLS#O5736594. Isleworth Realty Llc. MFR

Isleworth | For Sale

$4,900,000

Listed For 57 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    7008

  • Year Built

    1991

  • $/SqFt

    $699

The serene views are simply breathtaking. MLS#O5735188. Isleworth Realty Llc. MFR

Isleworth | For Sale

$2,400,000

Listed For 63 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5695

  • Year Built

    2008

  • $/SqFt

    $421

The upper level features two bedroom suites, a private loft and an extended balcony overlooking the sparkling pool, spa and garden views. MLS#O5733920. Isleworth Realty Llc. MFR

Isleworth | For Sale

$3,399,000

Reduced By $100,000

Listed For 70 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    6598

  • Year Built

    2016

  • $/SqFt

    $515

Other home features include a whole house generator, home automation, light filtering retractable screens, a private home theater with incredible audio & an outdoor living area with glistening pool, spa with water rain feature, pergola & a large lanai with lounge area & summer kitchen. MLS#O5731819. Premier Sothebys Int'L Realty. MFR

Isleworth | For Sale

$2,650,000

Reduced By $850,000

Listed For 73 Days
  • Bedrooms

    7

  • Full Bath(s)

    7

  • Sq. Ft.

    10464

  • Year Built

    1999

  • $/SqFt

    $253

Buyer to independently verify HOA, all measurements and condition. MLS#O5731874. Keller Williams Classic Realty. MFR

Isleworth | For Sale

$1,699,000

Listed For 107 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3745

  • Year Built

    2006

  • $/SqFt

    $453

In addition to the private courtyard, the home boasts a lovely patio located off of the living room that perhaps best captures the lovely water and garden views. MLS#O5724049. Isleworth Realty Llc. MFR

Isleworth | Pended

$1,628,000

Listed For 109 Days
  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4676

  • Year Built

    1988

  • $/SqFt

    $348

Outside, the screened lanai opens to a lovely open-air swimming pool surrounded by native Florida landscaping – all with a backdrop of stunning golf and lake views. MLS#O5722802. Isleworth Realty Llc. MFR

Isleworth | For Sale

$2,450,000

Listed For 123 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5235

  • Year Built

    1997

  • $/SqFt

    $468

A tropical oasis with southwestern exposure for optimum Florida sunlight and nightly firework displays from area theme parks, the pool offers a heated spa, underwater bar stools and surrounding deck accented by beautiful palm trees. MLS#O5719515. Isleworth Realty Llc. MFR

Isleworth | For Sale

$23,000,000

Listed For 129 Days
  • Bedrooms

    11

  • Full Bath(s)

    10

  • Sq. Ft.

    25466

  • Year Built

    1999

  • $/SqFt

    $903

Click on the virtual tour to see the video. MLS#O5714911. Exp Realty Llc. MFR

Isleworth | For Sale

$2,700,000

Listed For 149 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3866

  • Year Built

    1992

  • $/SqFt

    $698

Furnishings from local designer Saxon & Clark are also available for purchase. MLS#O5715880. Re/Max 200 Realty. MFR

Isleworth | For Sale

$7,200,000

Listed For 159 Days
  • Bedrooms

    6

  • Full Bath(s)

    8

  • Sq. Ft.

    12128

  • Year Built

    2006

  • $/SqFt

    $593

The grounds showcase sprawling gardens with a custom fountain, walking paths, a butterfly garden, and impeccably maintained landscaping as well as a private motor court flanked by a pair of two-car garages equating to over 1,300-square-feet, one of which features an expansive storage room. MLS#O5713515. Isleworth Realty Llc. MFR

Isleworth | For Sale

$6,300,000

Listed For 162 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    9811

  • Year Built

    2002

  • $/SqFt

    $642

Important works of art and select furniture may be available. MLS#O5713089. Isleworth Realty Llc. MFR

Isleworth | For Sale

$4,450,000

Listed For 171 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    7388

  • Year Built

    1991

  • $/SqFt

    $602

With more than 160 feet of water frontage, the estate presents panoramic views of lake and sky to be enjoyed all year round. MLS#O5710520. Isleworth Realty Llc. MFR

Isleworth | For Sale

$1,899,900

Reduced By $99,100

Listed For 174 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5371

  • Year Built

    1993

  • $/SqFt

    $353

Timeless elegance at it's finest is waiting for you! MLS#O5710334. Irwin Realty Group Llc. MFR

Isleworth | For Sale

$2,975,000

Reduced By $100,000

Listed For 191 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    5557

  • Year Built

    1990

  • $/SqFt

    $535

Set amidst beautiful sunsets and nightly firework displays from area theme parks, the home delivers unforgettable views. MLS#O5706286. Isleworth Realty Llc. MFR

Isleworth | For Sale

$2,895,000

Listed For 199 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6656

  • Year Built

    2002

  • $/SqFt

    $434

Connecting the main home to the detached guest house is a romantic courtyard with covered walkway, lush landscaping and a sparkling fountain made of exquisite Cantera stone from Mexico. MLS#O5704644. Isleworth Realty Llc. MFR

Isleworth | For Sale

$8,600,000

Reduced By $650,000

Listed For 201 Days
  • Bedrooms

    8

  • Full Bath(s)

    9

  • Sq. Ft.

    13230

  • Year Built

    2004

  • $/SqFt

    $650

Just minutes from world class shopping, fine dining, and all of the area attractions, the owners of this remarkable home will never have a shortage of things to do. MLS#O5700351. Regal R.E. Professionals Llc. MFR

Isleworth | For Sale

$2,950,000

Reduced By $350,000

Listed For 201 Days
  • Bedrooms

    6

  • Full Bath(s)

    7

  • Sq. Ft.

    7159

  • Year Built

    1999

  • $/SqFt

    $412

A detached guest house with private entrance and a four-car garage complete this magnificent golf-front estate. MLS#O5703955. Isleworth Realty Llc. MFR

Isleworth | For Sale

$2,300,000

Listed For 204 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    5840

  • Year Built

    2006

  • $/SqFt

    $393

Further highlights include a stately home office, detached guest cabana and a three-car garage. MLS#O5703882. Isleworth Realty Llc. MFR

Isleworth | For Sale

$2,180,000

Reduced By $520,000

Listed For 212 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4880

  • Year Built

    1994

  • $/SqFt

    $446

Outside, the fenced grounds showcase a lovely open-air swimming pool and spa with water feature, as well as a private putting green and separate covered summer kitchen and dining area – all overlooking the beautiful golf course views. MLS#O5702013. Isleworth Realty Llc. MFR