EasyStreet

Call to Schedule a Showing

(407) 278-2057

(407) 278-2057

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

$28,000,000

View 9927 Giffin Ct Windermere FL
View 9927 Giffin Ct Windermere FL
View 9927 Giffin Ct Windermere FL
Listed For 6 Days
  • Bedrooms

    12

  • Full Bath(s)

    11

  • Sq. Ft.

    31000

  • Year Built

    1990

  • $/SqFt

    $903

Other highlights include gated entry, full house Crestron technology, 17 plus car garages with showroom details, 3 fireplaces, walk-in humidor and wine storage, two story ceilings, 15 feet in depth pool with rock wall water feature, summer kitchen, custom chef?s kitchen, covered cabana and 10-foot privacy wall MLS#O5704312. Premier Sothebys Int'L Realty. MFR

Isleworth | For Sale

$1,899,999

View 9322 Isleworth Gardens Dr Windermere FL
View 9322 Isleworth Gardens Dr Windermere FL
View 9322 Isleworth Gardens Dr Windermere FL
*POTENTIAL GREAT VALUE
Listed For 8 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3745

  • Year Built

    2006

  • $/SqFt

    $507

The property is capped of with a fabulous enclosed pool area with a seating area, gas fireplace ,and a full outdoor kitchen with bar. MLS#O5707736. Regal R.E. Professionals Llc. MFR

Isleworth | For Sale

$3,075,000

View 9724 Chestnut Ridge Dr Windermere FL
View 9724 Chestnut Ridge Dr Windermere FL
View 9724 Chestnut Ridge Dr Windermere FL
Listed For 13 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    5557

  • Year Built

    1990

  • $/SqFt

    $553

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

View 5191 Isleworth Country Club Dr Windermere FL
View 5191 Isleworth Country Club Dr Windermere FL
View 5191 Isleworth Country Club Dr Windermere FL
Listed For 21 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

$9,250,000

Listed For 23 Days
  • Bedrooms

    8

  • Full Bath(s)

    9

  • Sq. Ft.

    13230

  • Year Built

    2004

  • $/SqFt

    $699

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

$3,300,000

Listed For 23 Days
  • Bedrooms

    6

  • Full Bath(s)

    7

  • Sq. Ft.

    7159

  • Year Built

    1999

  • $/SqFt

    $460

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 26 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

$2,700,000

Listed For 34 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4880

  • Year Built

    1994

  • $/SqFt

    $553

all overlooking the beautiful golf course views MLS#O5702013. Isleworth Realty Llc. MFR

Isleworth | For Sale

$3,295,000

Listed For 35 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6423

  • Year Built

    1996

  • $/SqFt

    $513

The expansive fenced grounds offer a sparkling open-air pool and spa, a covered lanai, basketball court and a separated, detached summer kitchen with pool bath. MLS#O5701998. Isleworth Realty Llc. MFR

Isleworth | For Sale

$1,825,000

Reduced By $70,000

Listed For 36 Days
  • Bedrooms

    4

  • Full Bath(s)

    6

  • Sq. Ft.

    7671

  • Year Built

    1987

  • $/SqFt

    $237

Don?t miss your opportunity to see this exceptional home MLS#O5700329. Regal R.E. Professionals Llc. MFR

Isleworth | For Sale

$2,695,000

Listed For 37 Days
  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    6933

  • Year Built

    1991

  • $/SqFt

    $388

The fenced grounds offer a covered lanai with summer kitchen overlooking the fire pit, heated spa and open-air pool surrounded by natural Florida landscaping and views of Isleworth?s famed championship golf course MLS#O5701374. Isleworth Realty Llc. MFR

Isleworth | For Sale

$1,625,000

Listed For 40 Days
  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    5610

  • Year Built

    2004

  • $/SqFt

    $289

This fabulous neighborhood quitesimply cannot be matched with amenities like championship golf, an amazing country club, access to the Butler Chain of lakes, tennis, fitness center, and concierge service. MLS#O5572938. Regal R.E. Professionals Llc. MFR

Isleworth | For Sale

$6,650,000

Listed For 47 Days
  • Bedrooms

    6

  • Full Bath(s)

    7

  • Sq. Ft.

    8049

  • Year Built

    1992

  • $/SqFt

    $826

The upper level boasts an additional master suite, two guest suites and media room with built-in bar. MLS#O5573526. Isleworth Realty Llc. MFR

Isleworth | For Sale

$2,250,000

Listed For 47 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4698

  • Year Built

    1990

  • $/SqFt

    $478

For those who value the finer things in life, this estate sets the standard for the unrivaled lifestyle that is lsleworth. MLS#O5572902. Lakeside Realty Windermere Inc. MFR

Isleworth | For Sale

$1,995,000

Listed For 48 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    4262

  • Year Built

    2007

  • $/SqFt

    $468

Don't wait to view this remarkable home! MLS#O5573218. Razzani International Realty. MFR

Isleworth | For Sale

$1,700,000

Listed For 49 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3999

  • Year Built

    1987

  • $/SqFt

    $425

Isleworth Country Club offers Social or Golf Memberships. MLS#O5572844. Re/Max Premier Properties Ii. MFR

Isleworth | For Sale

$4,999,000

Listed For 51 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    8400

  • Year Built

    1990

  • $/SqFt

    $595

By night the grounds come to life, with a sprawling terrace, summer kitchen, open-air pool and spa, and manicured landscaping enveloped by mature trees and panoramic lake views. MLS#O5571293. Isleworth Realty Llc. MFR

Isleworth | Pended

$1,942,900

*IS BANK OWNED
Listed For 60 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6584

  • Year Built

    2006

  • $/SqFt

    $295

This is a must see for your Isleworth Buyer and the home is priced to sell. MLS#O5570664. Buyer'S & Seller'S Realty, Inc. MFR

Isleworth | For Sale

$2,070,000

Listed For 70 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5328

  • Year Built

    2001

  • $/SqFt

    $388

In addition to its many amenities Isleworth is 24 hour guard gated, home to the famous Isleworth Golf & Country Club, zoned for top rated schools, and located conveniently to Orlando?s best restaurants, shopping, and attractions MLS#O5568631. Keller Williams Classic Realty. MFR

Isleworth | For Sale

$7,950,000

Listed For 73 Days
  • Bedrooms

    7

  • Full Bath(s)

    7

  • Sq. Ft.

    10730

  • Year Built

    2018

  • $/SqFt

    $740

No expense was spared on this truly stunning estate with too many custom upgrades, features, and energy efficient features to list. MLS#O5565384. Infinity Realty Group Llc. MFR

Isleworth | For Sale

$3,875,000

Listed For 96 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    7073

  • Year Built

    2001

  • $/SqFt

    $547

A three-minute boat ride connects you to the Club and amenities, offering the coveted lifestyle found only at Isleworth. MLS#O5563361. Isleworth Realty Llc. MFR

Isleworth | For Sale

$3,100,000

Listed For 98 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5752

  • Year Built

    2002

  • $/SqFt

    $538

Please see all upgrades on the attached document MLS#O5562746. Regal R.E. Professionals Llc. MFR

Isleworth | Pended

$5,295,000

Listed For 117 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    10394

  • Year Built

    2006

  • $/SqFt

    $509

On the upper level, a large game room easily converts to a home theater and opens to a multi-level balcony overlooking the custom pool with lap lane, water features, spa and a swim-up fireplace surrounded by a lanai with summer kitchen and manicured gardens. MLS#O5559035. Isleworth Realty Llc. MFR

Isleworth | For Sale

$5,495,000

Listed For 168 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    8802

  • Year Built

    2017

  • $/SqFt

    $624

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. MLS#O5547156. Isleworth Realty Llc. MFR

Isleworth | For Sale

$5,395,000

Listed For 168 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    8162

  • Year Built

    2017

  • $/SqFt

    $660

Four additional bedroom suites round out the upper level, along with a large conversion room and expansive wraparound terrace capturing multiple golf and water views, including Isleworth?s signature hole MLS#O5547144. Isleworth Realty Llc. MFR