$5,100,000

5243 Isleworth Country Club Drive

Windermere, FL 34786

Active
4
Beds
6
Baths
6,424
Sq Ft
0.51
Acres
1992
Built
Water viewWater accessPrivate poolFireplace3-car garage$794/sqft360° tour
🏠Single Family Residence

Property type

🏗️1992

Year built

📐22,199 sqft

Lot size

📊$794

Price / sq ft

🏘️$1,224/mo

HOA dues

📅153

Days on market

🚗3

Garage spaces

🌊X

Flood zone

About this home

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.

Estimated monthly payment

Principal & interest$25,788
Property taxes$4,183
Home insurance (est.)$2,338
HOA dues$1,224

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history153 days on market

  1. Status: Active
    Oct 9, 2025
  2. Listed$5,325,000
    Oct 9, 2025
  3. Price reduced$5,100,000

Virtual Tour

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
153
Subdivision
Isleworth
County
Orange
Year built
1992
Living area
6,424 sq ft
Price/sq ft
$794
Building area
7,246 sq ft (Public Records)
Lot size
22,199 sq ft
Lot category
1/2 to less than 1
Flood zone
X (12095C0385F)
Garage
3 spaces
Pool
Private pool
Annual taxes
$50,194 (2024)
Parcel #
28-23-16-3899-02-310
Zoning
P-D
MLS #
O6348067

Interior Details

Bedrooms
4
Full bathrooms
5
Half bathrooms
1
Flooring
Carpet, Marble, Tile, Wood
Appliances
Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Interior features
Built-in Features, Ceiling Fans(s), Central Vaccum, Coffered Ceiling(s), Crown Molding, Eat-in Kitchen, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments
Laundry
Inside
Stories / Levels
Two
Direction faces
North
Fireplace
Yes

Heating & Cooling

Heating
Central, Electric, Zoned
Cooling
Central Air, Zoned

Parking

Garage spaces
3
Attached garage
Yes
Parking features
Circular Driveway, Garage Faces Side, Golf Cart Garage

HOA & Financial

HOA fee
$3,672 / Quarterly
Monthly HOA
$1,224/mo
Total monthly fees
$1,224/mo
Total annual fees
$14,688
HOA name
Dan O'Connell
CDD
No
Homestead exemption
Yes
Min lease term
1-2 Years
Listing terms
Cash, Conventional
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
Contact the Isleworth Community Association (ICA); Minimum 1 year lease required
Approval process
Contact the Isleworth Community Association (ICA); Minimum 1 year lease required

Exterior & Construction

Exterior features
French Doors, Lighting, Outdoor Kitchen, Storage
Construction materials
Block, Stucco
Roof
Tile
Foundation
Slab
Pool
Private pool
Water access
Yes
Water view
Yes
Road surface
Asphalt

Utilities

Sewer
Septic Tank
Water source
Public
Utilities
Cable Connected, Natural Gas Connected, Underground Utilities, Water Connected

Community

Pets allowed
Yes

Schools

ElementaryAWindermere ElemGreatSchools ↗
MiddleCChain of Lakes MiddleGreatSchools ↗
High SchoolAOlympia HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
Family RoomFirst27x26
Living RoomFirst27x22
Dining RoomFirst18x12
DenFirst17x13
KitchenFirst18x17
DinetteFirst14x11
Primary BedroomFirst23x20
Bedroom 3Second19x13
Bedroom 3Second17x12
Bedroom 4Second16x12
Media RoomSecond17x13

Listing Details

Listing date
2025-10-09
On market date
2025-10-09
Original list price
$5,325,000
Occupant type
Owner
MLS area
34786 - Windermere
Listing AOR
Orlando Regional
Status changed
2025-10-09
Tax legal description
ISLEWORTH 16/118 LOT 231

Flood risk

Minimal riskFEMA Zone XPanel 12095C0385F

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

From I-4, take Conroy Road West. From Apopka Vineland Rd and Conroy Windermere Roads, go west on Conroy Windermere into Windermere. Left into Isleworth. After guard house, go straight on Isleworth Country Club Drive. House is on the left.

Property sale history

Public records

5243 ISLEWORTH COUNTRY CLUB DR, Windermere 34786

  • Aug 2024$5,250,000

5,629 sq ft · Built 1992 · 0.5096 acres

Sale data from Florida public records (Department of Revenue / county property appraiser). Deemed reliable but not guaranteed; may not reflect current market or MLS status. Not Stellar MLS data.

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Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of March 11, 2026 at 10:54 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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