5092 Isleworth Country Club Drive, FL5092 Isleworth Country Club Drive, FL5092 Isleworth Country Club Drive, FL
Stellar MLS
1 / 63

$8,500,000

5092 Isleworth Country Club Drive

Windermere, FL 34786

Listing updated: October 2, 2026 at 6:49 AM ET

Active
Stellar MLSListing courtesy of Isleworth Realty Llc · Michelle Corbin · MLS #O6446272 · Active · 407-909-9000
4
Beds
5
Baths
7,100
Sq Ft
0.93
Acres
1995
Built
◆Water view◆Private pool◆Fireplace◆4-car garage◆$1,197/sqft
Single Family Residence

Property type

1995

Year built

40,620 sqft

Lot size

$1,197

Price / sq ft

$1,224/mo

HOA dues

1

Day on market

4

Garage spaces

X

Flood zone

About this home

Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive and has been beautifully reimagined with an extensive transformation over the last two years. The result is a sophisticated, move-in-ready home where timeless architectural character blends seamlessly with thoroughly modern style. Originally built by Pellegrini Homes and expanded to 7,100 square feet, the residence retains its signature architectural details, including custom ceilings, travertine floors with intricate tile inlays, and carefully crafted shell stone columns. The grandeur of the formal living room is accentuated by its soaring 20-foot ceiling, magnificent chandelier, and stately stone fireplace. A former bonus room has been thoughtfully transformed into the home's impressive new chef's kitchen, featuring custom cabinetry, an Italian-made 48-inch ILVE range, a luxury appliance collection, and elegant finishes. The original kitchen has been reimagined as a sophisticated entertaining bar with custom cabinetry, a built-in espresso cabinet, wine storage, and dedicated space for morning coffee and smoothies. Both spaces connect effortlessly to the casual dining area and formal dining room, creating an exceptional flow for everyday living and entertaining. The family room offers an open, airy setting with a built-in media display and effortless connection to the lanai. The main-level owner's suite provides a private retreat with a cozy fireplace, dual closets, and a lavish bath featuring dual vanities, a walk-in shower, and a luxurious soaking tub framed by elegant stone columns. A new main-level bedroom with private en-suite bath and an enlarged loft suite add flexibility for family and guests. Throughout the residence, new flooring, custom cabinetry and built-ins, designer lighting including bespoke Italian Murano glass fixtures, custom drapery, automated shades, and beautifully appointed furnishings create a cohesive, elevated aesthetic. Custom London-made closet lighting adds another layer of thoughtful detail, while modernized infrastructure, integrated technology, whole-home Wi-Fi, security, and smart-home features provide a seamless foundation for today's lifestyle. Outside, the residence has been transformed into an exceptional setting for both relaxation and entertaining. The pool has been resurfaced, outdoor living areas expanded, and a new outdoor kitchen and grilling area added, while a completely redesigned landscape, lighting, fencing, and fountain features enhance the grounds. Upstairs, the bedroom suites and expansive balcony capture panoramic views of the golf course and sparkling waters of Lake Bessie. The European-style lanai, with its graceful balustrade, creates an inviting setting for al fresco gatherings and captivating sunsets. This exceptional estate offers a rare combination of timeless architectural character, comprehensive modern improvements, sophisticated design, and an enviable golf-front setting within Isleworth.

Estimated monthly payment

Principal & interest$42,981
Property taxes$4,756
Home insurance (est.)$3,896
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
    Oct 1, 2026
  2. Listed$8,500,000
    Oct 1, 2026
  3. Price increased$8,500,000

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
1
Subdivision
Isleworth
County
Orange
Year built
1995
Living area
7,100 sq ft
Price/sq ft
$1,197
Building area
10,319 sq ft (Public Records)
Lot size
40,620 sq ft
Lot category
1/2 to less than 1
Flood zone
X
Garage
4 spaces
Pool
Private pool
Annual taxes
$57,071 (2026)
Parcel #
16-23-28-3899-00-480
Zoning
P-D
MLS #
O6446272

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Interior Details

Bedrooms
4
Full bathrooms
5
Flooring
Brick, Carpet, Marble, Travertine, Wood
Appliances
Bar Fridge, Built-In Oven, Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Water Filtration System, Wine Refrigerator
Interior features
Built-in Features, Cathedral Ceiling(s), Ceiling Fans(s), Central Vaccum, Crown Molding, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments
Laundry
Laundry Room
Stories / Levels
Two
Direction faces
East
Fireplace
Yes

Heating & Cooling

Heating
Central, Zoned
Cooling
Central Air, Zoned

Parking

Garage spaces
4
Attached garage
Yes
Parking features
Circular Driveway, Garage Door Opener, 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
8-12 Months
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
Balcony, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters
Construction materials
Block, Stucco
Roof
Tile
Foundation
Slab
Pool
Private pool
Water view
Yes
Road surface
Paved

Utilities

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

Community

Pets allowed
Breed Restrictions, 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
Living RoomFirst
KitchenFirst
Primary BedroomFirst
Dining RoomFirst
Family RoomFirst

Listing Details

Listing date
2026-10-01
On market date
2026-10-01
Original list price
$8,500,000
Occupant type
Owner
MLS area
34786 - Windermere
Listing AOR
Orlando Regional
Status changed
2026-10-01
Tax legal description
N 73 DEG W 204.27 FT S 22 DEG W ALONG LOTS 47 & 48 FOR 146.32 FT TO POB

Flood risk

Minimal riskFEMA Zone X

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 Windermere Road west to Isleworth subdivision. Stay straight on Isleworth Country Club Drive. Estate will be on the Left or Right.

Property sale history

Public records

5092 ISLEWORTH COUNTRY CLUB DR, Windermere 34786

  • Dec 2024$4,000,000

7,100 sq ft · Built 1995 · 0.9325 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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