Isleworth

Isleworth is a luxury country club community of single family homes, and townhomes in Windermere, Florida, with a range of options priced between $2,500,000 and $14,250,000. There are currently a total of 19 homes for sale in Isleworth. The smallest Isleworth home presently available is a three bedroom three bathroom residence that is 4,433 square feet (3,636SF Under Air living space), and the largest of the Isleworth homes currently on the market has seven beds and six baths and is a 30,056 square foot (9,511SF Under Air) residence.

Property management fees in Orange County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Isleworth range from $3,129 to $3,672 and $3,672 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, the community pool, and security. Also included is a 24-hour guard, real estate taxes for common areas, gas, water, electric, trash removal, and Cable TV & internet. Please check the individual listing pages for the exact homeowners association fees for a particular Isleworth home. Golf communities typically entail membership fees (sometimes mandatory) that are in addition to the HOA fees, so please check with your Realtor® or the club membership office.

Isleworth amenities include a clubhouse, swimming pool, spa / hot tub, a state-of-the-art fitness center, and sauna. Sports facilities include a championship golf course, tennis courts, pickleball courts, racquetball, and basketball court.

Boating enthusiasts will love the fact that the community has boat facilities including a boat ramp, and a private boat ramp. There is also a community park, a playground, as well as walking or jogging trails.

The Isleworth HOA rules do allow homeowners to have pets although there are certain breed restrictions. There is a limit of how many pets you may have, and there is a restriction on pet size. Dogs and cats are allowed.

There are four commercial airports that serve Isleworth - Orlando Executive (ORL), which is thirteen miles away; Orlando International (MCO), which is fourteen miles away; Kissimmee Gateway (ISM), which is fourteen miles away, and Orlando Sanford International (SFB), which is twenty seven miles away from Isleworth.

Isleworth real estate activity on the Windermere MLS during the past year (as of May 2026) reflects eighteen homes changing hands, with an average asking price of $5,392,222 and an average selling price of $4,988,889. This represents a healthy list-to-sell price ratio of 93% and $463 per square foot. During this period, Isleworth homes for sale have taken an average of 193 days to sell.

In addition, there are numerous other communities in Windermere to choose from, or you may browse all available Windermere Real Estate, including some new construction opportunities. Homes for sale in Isleworth are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Isleworth hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Central Florida real estate needs.

Isleworth Homes For Sale

Under Contract

$14,250,000

MLS#MFRO6304800

5525 Isleworth Country Club Dr
Windermere, FL 34786

5

6

6

12,319 SqFt

Pool

1.02 Acres

355 Days

$7.595 Million

MLS#MFRO6373191

5074 Isleworth Country Club Dr
Windermere, FL 34786

5

7

3

8,961 SqFt

Pool

0.54 Acres

115 Days

$6,980,000

MLS#MFRO6382040

5186 Vardon Dr
Windermere, FL 34786

4

5

3

7,875 SqFt

Pool

1.01 Acres

84 Days

Reduced

$6 Million

$6,950,000

MLS#MFRO6370294

9725 Chestnut Ridge Dr
Windermere, FL 34786

7

7

3

11,952 SqFt

Pool

Water Front

0.56 Acres

127 Days

$5.5 Million

MLS#MFRO6401757

5138 Fairway Oaks Dr
Windermere, FL 34786

4

5

3

5,911 SqFt

Pool

0.5 Acres

14 Days

Reduced

$5,250,000

$5,400,000

MLS#MFRO6372197

6117 Louise Cove Dr
Windermere, FL 34786

4

5

3

7,772 SqFt

Pool

Water Front

0.79 Acres

120 Days

Reduced

$5,100,000

$5,325,000

MLS#MFRO6348067

5243 Isleworth Country Club Dr
Windermere, FL 34786

4

6

3

7,246 SqFt

Pool

0.51 Acres

212 Days

Under Contract

$4.95 Million

MLS#MFRO6386548

6113 Payne Stewart Dr
Windermere, FL 34786

3

4

4

4,642 SqFt

Pool

Water Front

0.32 Acres

64 Days

Under Contract

$4.9 Million

MLS#MFRO6346003

5036 Latrobe Dr
Windermere, FL 34786

5

5

3

30,056 SqFt

Pool

Water Front

0.69 Acres

218 Days

$4,690,000

MLS#MFRO6400218

4906 Aviva Garden Ct
Windermere, FL 34786

3

5

4

9,479 SqFt

Pool

0.26 Acres

19 Days

$4,450,000

MLS#MFRO6397842

9144 Isleworth Gardens Dr
Windermere, FL 34786

3

5

3

7,228 SqFt

Pool

0.26 Acres

30 Days

Reduced

$3.9 Million

$4,100,000

MLS#MFRO6392380

5151 Latrobe Dr
Windermere, FL 34786

4

5

3

7,172 SqFt

Pool

0.51 Acres

50 Days

19 Active Listings in Isleworth