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Eileen Astra
REALTOR®
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5092 Isleworth Country Club Drive, Windermere, FL 34786

$8,500,000
  • 5092 Isleworth Country Club Drive, Windermere, FL 34786 Main Photo

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New to the Market Active
BEDS4 BATHS5 full SQUARE FEET7,100 MLS#O6446272
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONISLEWORTH

Property Description

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.

5092 Isleworth Country Club Drive | MLS# O6446272

This single family home located at 5092 Isleworth Country Club Drive, Windermere, FL 34786 is currently listed for sale with an asking price of $8,500,000. This property was built in 1995 and has 4 bedrooms and 5 full baths with 7100 sq. ft. Isleworth Country Club Drive is located in the ISLEWORTH subdivision. Search ISLEWORTH real estate on eastra.floridaexecutiverealty.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air, Zoned
Fenced: Yes
Garage: 4 car attached
Heating: Central, Zoned
Home Style: Mediterranean
Lot Size: 0.93 Acres
Roof Type: Tile
Stories: 2.0
Taxes: $57,070
Year Built: 1995

Amenities

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
Balcony
Lighting
Outdoor Grill
Outdoor Shower
Rain Gutters

Feature Descriptions

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
Association Amenities: Cable TV, Gated, Maintenance, Optional Additional Fees, Playground, Security
Body of Water: BUTLER CHAIN OF LAKES
Community Features: Association Recreation - Owned, Community Mailbox, Fitness Center, Golf Carts OK, Golf, Playground, Pool, Tennis Court(s), Street Lights
Days on Site: 4
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.
Exterior: Block, Stucco
Fencing: Fenced
Fireplace: Living Room, Primary Bedroom
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Brick, Carpet, Marble, Travertine, Wood
Foundation: Slab
HOA Fee: 3672/ Quarterly
HOA Y/N: Yes
Home Warranty Y/N: No
Listing Terms: Cash, Conventional
Lot: Landscaped, On Golf Course, Oversized Lot, Paved, Private
Lot Dimensions: 0.93
Other Equipment: Irrigation Equipment
Ownership: Fee Simple
Parking: Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
Parking Notes: Circular Driveway, Garage Door Opener, Garage Faces
Pets Allowed: Breed Restrictions, Yes
Pets Restrictions: Per Orange County breed restrictions, number limits and leash laws.
Pool: In Ground, Lighting
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Security: Closed Circuit Camera(s), Gated Community, Security Gate, Security Lights, Security System, Smoke Detector(s)
Sewer: Septic Tank
Showing Instructions: 24 Hour Notice, Appointment Only, Call Before Showing, Call Listing Agent, Listing Agent Must Accompany, See Remarks
Spa: Heated, In Ground
Special Sale Provisions: None
Swimming Pool: Yes
Utilities: Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Underground Utilities
Vegetation: Mature Landscaping, Trees/Landscaped
Water: Public
Water Access Y/N: No
Water View: Lake - Chain of Lakes
Windows: Drapes, Shutters, Window Treatments
Zoning: P-D

Local Schools

High School: Olympia High
Middle School: Chain of Lakes Middle
Elementary School: Windermere Elem

Listed By / Shown By

Listed By

Agency Name: ISLEWORTH REALTY LLC
Agency Contact: 407-909-9000

Shown By

Agent Name: Eileen Astra
Agent Phone: Cell: (727) 247-9247
Agency Title: Florida Executive Realty

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Estimated Payment

$ 26,152.32 per month $18,917.32 Principal & Interest $4,755.83 Property Tax $2,479.17 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 10/06/2026. The listing information on this page last changed on 10/06/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 10/06/2026 12:18:18 AM EST) or Stellar MLS (last updated Tue 10/06/2026 12:09:48 AM EST). Real estate listings held by brokerage firms other than Florida Executive Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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