5373 Isleworth Country Club Drive, FL5373 Isleworth Country Club Drive, FL5373 Isleworth Country Club Drive, FL
Stellar MLS
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$7,200,000

5373 Isleworth Country Club Drive

Windermere, FL 34786

Listing updated: September 9, 2026 at 6:51 AM ET

Active
Stellar MLSListing courtesy of Stockworth Realty Group · Rob Rahter · MLS #O6439156 · Active · 407-909-5900
5
Beds
6
Baths
5,993
Sq Ft
0.52
Acres
1988
Built
Water viewWater accessPrivate poolFireplace3-car garage$1,201/sqft360° tour
Single Family Residence

Property type

1988

Year built

22,762 sqft

Lot size

$1,201

Price / sq ft

$1,224/mo

HOA dues

1

Day on market

3

Garage spaces

X

Flood zone

About this home

Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyond. This home was completely gutted and rebuilt with everything masterfully crafted to create a shimmering grand statement of luxury living on one of the most premier lots in the community. The spectacular 10-foot tall, 6-foot wide swinging front door sets the stage for a residence of distinction. A grand, light filled entry welcomes with soaring ceilings, polished marble floors, and a dramatic glass railed staircase that create an immediate sense of scale and sophistication. The open layout flows seamlessly through the dramatic great room toward a wall of floor to ceiling windows and accordion folding glass doors, inviting natural light and showcasing picturesque views of the just-completed saltwater pool and hot tub, golf course, and lake beyond. An elegant chandelier anchors the space, while the upper level glass balcony adds architectural interest and a modern, gallery style feel. Two bedroom suites on the first floor include an extraordinary primary retreat with double closets - one with a stackable washer and dryer - sitting room, and spa-like bath with glassed wet room with enclosed shower and tub. The stunning chef’s kitchen blends modern elegance with exceptional functionality, showcasing a stunning waterfall edge island wrapped in premium marble. Sleek, custom white cabinetry pairs with professional stainless steel appliances – which include WOLF 6-burner plus griddle cooktop, dishwasher, ice maker, and double ovens - create a clean, architectural aesthetic, while the rich wood flooring adds warmth and contrast. Designer pendant lighting highlights the generous prep and gathering areas, making the kitchen equally suited for intimate mornings or elevated entertaining. The open layout flows seamlessly into the surrounding living spaces, including a formal dining room with butler’s pantry, family dining room and secondary gathering space, enhancing the home’s sense of scale and sophistication. Every detail—from the integrated hood to the refined hardware—reflects a commitment to luxury craftsmanship and timeless style. Upstairs are three additional bedroom suites including one that could be a second master. Outdoor entertaining is inviting and refined with a sparkling pool and spa, expansive pool deck, and just-built cabana with summer kitchen. Full-house generator. The 600-acre Isleworth community is surrounded by the pristine Butler Chain of Lakes and is an exclusive residential enclave that sets the standard of excellence for Central Florida living, with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional golf and social membership opportunities.

Estimated monthly payment

Principal & interest$36,407
Property taxes$3,626
Home insurance (est.)$3,300
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 history1 days on market

  1. Status: Active
    Sep 8, 2026
  2. Listed$7,200,000
    Sep 8, 2026
  3. Price increased$7,200,000

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
1
Subdivision
Isleworth
County
Orange
Year built
1988
Living area
5,993 sq ft
Price/sq ft
$1,201
Building area
7,675 sq ft (Estimated)
Lot size
22,762 sq ft
Lot category
1/2 to less than 1
Flood zone
X (12095C0385F)
Garage
3 spaces
Pool
Private pool
Annual taxes
$43,509 (2025)
Parcel #
28-23-16-3899-02-150
Zoning
P-D
MLS #
O6439156

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Interior Details

Bedrooms
5
Full bathrooms
5
Half bathrooms
1
Flooring
Hardwood, Marble, Tile
Appliances
Convection Oven, Cooktop, Dishwasher, Dryer, Ice Maker, Microwave, Refrigerator, Tankless Water Heater, Washer
Interior features
Built-in Features, Cathedral Ceiling(s), Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Tray Ceiling(s)
Laundry
Inside, Laundry Room
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 Door Opener, Garage Faces Side, Parking Pad

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
Min lease term
1-2 Years
Listing terms
Cash, Conventional
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
Per Isleworth Community Association (ICA)
Approval process
Per Isleworth Community Association (ICA)

Exterior & Construction

Exterior features
Outdoor Kitchen, Rain Gutters
Construction materials
Block, Concrete, Stucco
Roof
Tile
Foundation
Block, Slab
Pool
Private pool
Water access
Yes
Water view
Yes
Road surface
Paved

Utilities

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

Community

Pets allowed
Breed Restrictions

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
Primary BedroomFirst25x29
Primary BathroomFirst9x21
Living RoomFirst28x25
KitchenFirst31x18
DinetteFirst13x14
Dining RoomFirst18x17
FoyerFirst28x22
Bedroom 2First15x17
Bedroom 3Second18x19
Bedroom 4Second15x14
Bedroom 5Second18x32

Listing Details

Listing date
2026-09-08
On market date
2026-09-08
Original list price
$7,200,000
Occupant type
Vacant
MLS area
34786 - Windermere
Listing AOR
Orlando Regional
Status changed
2026-09-08
Tax legal description
ISLEWORTH 16/118 LOT 215

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

I-4 to Conroy Road West follow Conroy Road to the torn of Windermere, one quarter mile west from Apopka Vineland on Conroy Windermere Road. Left into the main gate. Follow Isleworth Country Club Drive to property address.

Property sale history

Public records

5373 ISLEWORTH COUNTRY CLUB DR, Windermere 34786

  • Jan 2024$3,000,000

5,993 sq ft · Built 1988 · 0.5225 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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