Windermere, FL · Single Family Residence
5092 Isleworth Country Club Dr
Active · MLS MFRO6446272 · Listed by ISLEWORTH REALTY LLC · 407-909-9000.
THE SETTING, AND THE DETAILS
A closer look.
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.
The details that help you decide.
Details supplied with the listing. Information that was not provided is marked below.
Home essentials
- Price per square foot
- $1,197
- Full bathrooms
- 5
- Half bathrooms
- 0
- Heated living area
- 7100
- Lot size (acres)
- 0.93
- Lot size (sq ft)
- 40620
- Year built
- 1995
- Property type
- Residential
- Property style
- Mediterranean
Interior & rooms
- 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
- 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
- Flooring
- Brick, Carpet, Marble, Travertine, Wood
- Additional rooms
- Not provided
Land, water & community
- Waterfront
- No
- Waterfront type
- Not provided
- Water body / lake name
- BUTLER CHAIN OF LAKES
- Water view
- Lake - Chain of Lakes
- Dock
- Not provided
- Dock features
- Not provided
- Other views
- Garden, Golf Course, Trees/Woods, Water
- Lot features
- Landscaped, On Golf Course, Oversized Lot, Paved, Private
- Exterior features
- Balcony, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters
- Community amenities
- Association Recreation - Owned, Community Mailbox, Fitness Center, Golf Carts OK, Golf, Playground, Pool, Tennis Court(s), Street Lights
- Zoning
- P-D
- Current use
- Not provided
- Horse amenities
- Not provided
- Fencing
- Fenced
- Other structures
- Not provided
Pool, parking & systems
- Private pool
- Yes
- Pool features
- In Ground, Lighting
- Garage
- Yes
- Garage spaces
- 4
- Carport
- No
- Carport spaces
- Not provided
- Parking features
- Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
- Fireplace
- Yes
- Fireplace features
- Living Room, Primary Bedroom
- Heating
- Central, Zoned
- Cooling
- Central Air, Zoned
- Water supply
- Public
- Sewer
- Septic Tank
- Utilities
- Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Underground Utilities
Construction
- Construction materials
- Block, Stucco
- Roof
- Tile
- Foundation
- Slab
- Stories
- Not provided
- Levels
- Two
Location & schools
- City
- WINDERMERE
- Subdivision
- ISLEWORTH
- County
- Orange
- ZIP code
- 34786
- Elementary school
- Windermere Elem
- Middle school
- Chain of Lakes Middle
- High school
- Olympia High
Association, taxes & listing
- HOA / association
- Yes
- Association fee
- $3,672
- Fee frequency
- Quarterly
- Included services
- Guard - 24 Hour, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance, Private Road, Security
- Association amenities
- Cable TV, Gated, Maintenance, Optional Additional Fees, Playground, Security
- Additional association fee
- Not provided
- Additional fee frequency
- Not provided
- Condo fee
- Not provided
- Condo fee frequency
- Not provided
- Annual property taxes
- $57,070.63
- Tax year
- 2026
- Other annual assessments
- Not provided
- CDD
- No
- Listing status
- Active
- Days on market
- 0
- Listing broker
- ISLEWORTH REALTY LLC
- MLS number
- MFRO6446272
Explore the area
Location supplied with the listing. Confirm boundaries and access for the property.
Listed by ISLEWORTH REALTY LLC · MLS MFRO6446272
Source: mfrmls · Listing updated 2026-10-01 17:31:17 UTC.
Information is deemed reliable but is not guaranteed. Availability and details may change.
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