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 $12,350,000. There are currently a total of 22 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 nine baths and is a 30,056 square foot (11,465SF 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 $1,224 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; Kissimmee Gateway (ISM), which is fourteen miles away; Orlando International (MCO), 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 June 2026) reflects nineteen homes changing hands, with an average asking price of $5,658,421 and an average selling price of $5,201,974. This represents a healthy list-to-sell price ratio of 92% and $499 per square foot. During this period, Isleworth homes for sale have taken an average of 200 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 BEX Realty agent, who would happily assist you further with all your Central Florida real estate needs.

Isleworth Homes For Sale

$13.9 Million

MLS#MFRO6416194

9832 Laurel Valley Dr
Windermere, FL 34786

6

10

4

12,796 SqFt

Pool

Water Front

0.6 Acres

12 Days

$12,350,000

MLS#MFRO6407102

9312 Blanche Cove Dr
Windermere, FL 34786

7

10

4

18,275 SqFt

Water Front

4.03 Acres

7 Days

Reduced

$7,250,000

$7,595,000

MLS#MFRO6373191

5074 Isleworth Country Club Dr
Windermere, FL 34786

5

7

3

9,236 SqFt

Pool

0.54 Acres

160 Days

$6.95 Million

MLS#MFRO6407107

6462 Deacon Cir
Windermere, FL 34786

5

6

3

9,057 SqFt

Pool

Water Front

0.64 Acres

41 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

172 Days

$5.5 Million

MLS#MFRO6401757

5138 Fairway Oaks Dr
Windermere, FL 34786

4

5

3

5,911 SqFt

Pool

0.5 Acres

59 Days

$5,300,000

MLS#MFRO6409961

5199 Latrobe Dr
Windermere, FL 34786

6

7

4

6,622 SqFt

Pool

0.52 Acres

27 Days

Under Contract

$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

165 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

257 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

263 Days

$4,590,000

MLS#MFRO6400218

4906 Aviva Garden Ct
Windermere, FL 34786

3

5

4

9,479 SqFt

Pool

0.26 Acres

64 Days

$4,450,000

MLS#MFRO6397842

9144 Isleworth Gardens Dr
Windermere, FL 34786

3

5

3

7,228 SqFt

Pool

0.26 Acres

75 Days

22 Active Listings in Isleworth