4 Days Ago
Location
5243 Isleworth Country Club Dr, Windermere, FL 34786, USA
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Property Overview
Luxury living on Isleworth Country Club Dr with a prestigious Windermere address, likely offering access to an upscale golf community setting, strong curb appeal, and refined surroundings. It stands out for buyers seeking elegance, privacy, and a highly desirable Central Florida location with notable community amenities and a premium residential feel.
This summary uses Zumper’s proprietary data. “Things you’ll love” and “Great for” are based on our internal analyses of market trends and renter insights.
Things you’ll love
More space- Middle school nearby
- Fireplace
Great for
Wellness
Amenities for 5243 Isleworth Country Club Dr
Features
| Carpet | Ceiling Fan |
| Central Air | Den |
| Electric Heating | Fireplace |
| Hardwood Floor | High Ceilings |
| Walk-in Closet |
Appliances
| Dishwasher | In-Unit Laundry |
Community
| Fitness Center | Media Room |
| Roof Deck |
Grounds
| Garage Parking | Outdoor Space |
| Storage | Swimming Pool |
Other
| Eleven Rooms |
Units, floor plans, amenities, dimensions, details, availability, and prices may be approximate and subject to change. Please contact a community representative for more information.
Policies and fees
Applicants
Applicants
One-time.
Contact Property
REQUIRED FEES
Security Deposit
One-time. Refundable.
Contact Property
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About 5243 Isleworth Country Club Dr
Property Status: Active Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of privacy mixed with rare golf and water vistas. Home recently underwent a major “spare no expense” remodel by McNally Construction and design by Debby Dearth of McNally Design using the highest quality materials combining the latest designs with timeless Mediterranean architecture. Enter to an impressive foyer and Great Room with soaring 20-foot ceilings above and basket weaved marble and wood flooring below, complemented by wood beams, stone gas fireplace with marble mantle, and shimmering chandeliers. An adjacent cocktail bar next to the dining room is fitted with Cristallo quartzite counters and a temperature-controlled wine cellar that can easily accommodate 700+ bottles of wine. The well-appointed chef’s kitchen is fully equipped with a large center island, custom wood cabinetry, Italian dolomite counter tops, Sub Zero refrigerator, and a Wolf gas range with griddle. Family room and breakfast nook are perfectly sized for everyday entertaining with vaulted ceilings, reclaimed wood floors, and access to the pool patio and summer kitchen cabana. The dramatic first floor primary retreat features picturesque windows and a luxurious spa-like bath complete with chandelier, breakfast bar with Sub Zero fridge, dual vanities, garden tub, glass shower, and French doors to a walled outdoor space. The master closet provides access to a discrete room at the top of a spiral staircase that can be a gym, second study, or hidden Pilates room. Up the main staircase are three additional bedroom suites and a movie theater. An executive office is located on the first floor. Exterior living spaces feature a large covered lanai, heated saltwater pool, full pool bath, summer kitchen with stainless steel grill, sink, beverage refrigerator, custom-built stacked stone outdoor fireplace, and nearly 300 feet of golf frontage. Notable upgrades done in 2023 include a brand new tile roof, replacement of all custom doors and windows, remodeled kitchen, bathrooms with Kohler fixtures, door hardware, cocktail bar, flooring, Control 4 smart house features for lighting, electric shades, cameras, HVAC, pool equipment, garage doors, locks, built-in sound system, pool resurface, new pool heater, landscaping, complete interior and exterior paint, and exterior gray pavers. Home is built with concrete construction on both first and second floors. The 600-acre Isleworth community, surrounding the Butler Chain of Lakes, is a residential enclave that sets the standard of excellence for Central Florida living. Isleworth Golf & Country Club, which is located within the community, is recognized as one of the Top 100 Platinum Clubs of the World offering separate membership opportunities that provide access to golf, tennis, fitness, Clubhouse dining and social events, swimming in the resort-style pool and sundeck, dock, and an abundance of activities. Enjoy a lifestyle defined by casual elegance in a setting that sets the standard for luxury living. Also available for sale. Office Phone: (407) 909-5900 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be indep..
Property highlights
We compared every listing in the surrounding area to determine which amenities are most common. If a building lacks an amenity that most others in the area have, it is a con. If a building has an amenity most others in the area do not, it is a pro. Similarly, price, schools, and size are calculated relative to the size, price, and distance to schools of the other properties nearby.How 5243 Isleworth Country Club Dr compares to other nearby properties.
Positives
- More space
- The 4-bedroom is 3728 sqft larger than other listings nearby
- Middle school nearby
- There is a middle school 2 miles away
- Fireplace
- Upgraded in-unit features
- Images Available
- There are at least 10 photos of this address
Address details
| Zip code | 34786 |
|---|---|
| Type | House for rent |
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Rent trends in Windermere
4-bedroom apartments at 5243 Isleworth Country Club Dr cost about 658% more than the average rent price for 4-bedroom apartments in Windermere.
Median rents as of Jun 20 2026.
Windermere
| Month | Median Rent |
|---|---|
| July 2024 | $3,435 |
| August 2024 | $3,321 |
| September 2024 | $3,478 |
| October 2024 | $3,396 |
| November 2024 | $3,338 |
| December 2024 | $3,281 |
| January 2025 | $3,268 |
| February 2025 | $3,295 |
| March 2025 | $3,415 |
| April 2025 | $3,400 |
| May 2025 | $3,333 |
| June 2025 | $3,400 |
| July 2025 | $3,415 |
| August 2025 | $3,466 |
| September 2025 | $3,334 |
| October 2025 | $3,297 |
| November 2025 | $3,287 |
| December 2025 | $3,247 |
| January 2026 | $3,248 |
| February 2026 | $3,172 |
| March 2026 | $3,202 |
| April 2026 | $3,200 |
| May 2026 | $3,044 |
| June 2026 | $3,333 |
Affordability calculator
Can I afford to live at 5243 Isleworth Country Club Dr?
Bedrooms
4+ bedroomsRent-to-income ratio
30%
Slide to adjust the percentage of your monthly income you are willing to spend on rent.
The general rule of thumb is to spend around 30% or less of your income on rent.
Recommended income
$1,000,000/yr
With your selected rent-to-income ratio, you'd ideally want to make $1,000,000 annually to afford this 4-bedrooms monthly rent price of $25,000.
For more information on rent affordability, visit our rent calculator.
Schools near 5243 Isleworth Country Club Dr
Windermere Elementary School
11125 park ave
windermere, FL, 34786
PK, K-5Public
A
Westpointe Elementary School
7525 westpointe blvd
orlando, FL, 32835
PK, K-5Public
B+
Bay Lake Elementary School
12005 silverlake park dr
windermere, FL, 34786
PK, K-5Public
A-
Castleview Elementary School
9131 taborfield ave
orlando, FL, 32836
K-5Public
A-
Florida Virtual Elementary School
2145 metrocenter blvd ste 100
orlando, FL, 32835
K-5Public
B
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Internet available near 5243 Isleworth Country Club Dr
Neighborhood
Getting around Windermere near 5243 Isleworth Country Club Dr
Walking
2/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).
Driving
9/10
Commuting is easy with multiple accessible routes and plenty of parking.
Cycling
3/10
This is semi-bikeable, but you’ll need another way of getting around.
Transit
0/10
FYI, there are little to no public transit options within walking distance.
Points of interest for 5243 Isleworth Country Club Dr, Windermere
Groceries
3/10
Some groceries within a short drive
Shopping
2/10
Few or no shops within a short drive
Cafes
2/10
Some cafés within a short drive
Restaurants
4/10
Some restaurants within a short drive
Primary schools
0/10
Closest elementary school further than a 30-minute walk
High schools
1/10
Closest high school further than a 30-minute walk
Parks
4/10
Limited amount of park space nearby
Nightlife
2/10
Few or no bars within a short drive
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