Home in 5092 Isleworth Country Club Dr Windermere for sale with MLS# O6446272
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 Dr, Windermere, FL 34786
- Price:
- $8,500,000.00
- Original List Price:
- $8,500,000.00
- List Price per Sq Ft (Calculated, Approx.):
- $1,197.18
- Listing Type:
- For Sale
- Status:
- Active
- Listing Category:
- Residential
- Property Type:
- Single Family House
- MLS Number:
- O6446272
- Bedrooms:
- 4
- Bathrooms Total:
- 5
- Full Bath:
- 5
- Living Area:
- 7,100 Sqft
- Built-Up Area:
- 10,319 Sqft
- Lot Area:
- 40,620 Sqft
- Building Area Source:
- Public Records
- Living Area Source:
- Owner
- Lot Features:
- On Golf Course, Oversized Lot, Paved, Private, Landscaped
- Lot Size Acres:
- 0.93
- View from the Property:
- Garden, Water, Golf Course, Trees/woods
- Waterfront:
- No
- Private Pool
- Swimming Pool Features:
- In Ground, Lighting
- Spa
- Spa Features:
- Heated, In Ground
- Security:
- Smoke Detector(s), Security Gate, Security System, Closed Circuit Camera(s), Security Lights, Gated Community
- Furnished:
- Negotiable
- Appliances:
- Dryer, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Freezer, Built-in Oven, Electric Water Heater, Ice Maker, Exhaust Fan, Range, Range Hood, Convection Oven, Wine Refrigerator, Water Filtration System, Bar Fridge
- Interior:
- Eat-in Kitchen, High Ceilings, Walk-In Closet(s), Vaulted Ceiling(s), Built-in Features, Wet Bar, Cathedral Ceiling(s), Ceiling Fans(s), Kitchen/family Room Combo, Stone Counters, Window Treatments, Solid Wood Cabinets, Crown Molding, Central Vacuum, Primary Bedroom Main Floor
- Exterior:
- Balcony, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters
- Windows:
- Drapes, Shutters, Window Treatments
- Laundry:
- Laundry Room
- Fireplace
- Fireplace:
- Living Room, Primary Bedroom
- Air Conditioning System:
- Zoned, Central Air
- Heating System:
- Central, Zoned
- Fence:
- Fenced
- Vegetation and Trees:
- Trees/landscaped, Mature Landscaping
- Property Entrance Faces:
- East
- Other Equipment:
- Irrigation Equipment
- Water View
- Water View Details:
- Lake - Chain Of Lakes
- Year Built:
- 1995
- Roof:
- Tile
- Architectural Style:
- Mediterranean
- Levels:
- Two
- Construction Materials:
- Block, Stucco
- Flooring:
- Carpet, Wood, Marble, Travertine, Brick
- Foundation Details:
- Slab
- Flood Zone Code:
- X
- Homestead Property
- Tax Annual Amount:
- $57,070.63
- Tax Year:
- 2026
- Association Fee:
- $3,672.00
- Association Fee Frequency:
- Quarterly
- Total Annual Fees:
- $14,688.00
- Total Monthly Fees:
- $1,224.00
- Garage
- Garage Spaces:
- 4
- Attached Garage
- Parking Features:
- Garage Door Opener, Circular Driveway, Golf Cart Garage, Garage Faces Side
- Sewer:
- Septic Tank
- Utilities Available:
- Underground Utilities, Electricity Connected, Fire Hydrant, Natural Gas Connected, Cable Connected
- Water Source:
- Public
- Association
- Minimum Lease Term:
- 8-12 Months
- Pets Allowed?:
- Yes, Breed Restrictions
- Amenities Provided by the Homeowner's Association (HOA):
- Playground, Maintenance, Security, Gated, Cable Tv, Optional Additional Fees
- Subdivision Name:
- ISLEWORTH
- Community Features:
- Fitness Center, Street Lights, Pool, Tennis Court(s), Golf, Playground, Association Recreation - Owned, Golf Carts Ok, Community Mailbox
- Association Fee Includes:
- Maintenance Grounds, Cable Tv, Security, Internet, Escrow Reserves Fund, Guard - 24 Hour, Private Road, Maintenance
- Senior Community:
- No
- Association Fee Required:
- Required
- Association Management:
- Dan O’Connell
- Association Phone:
- 407-909-2071
- Listing Terms Considered by Seller:
- Cash, Conventional
- Occupant Type:
- Owner
- Lease Considered:
- Yes
- Tax Legal Description:
- N 73 DEG W 204.27 FT S 22 DEG W ALONG LOTS 47 & 48 FOR 146.32 FT TO POB
- Real Estate Folio Number (Parcel Number):
- 16-23-28-3899-00-480
- Zoning:
- P-D
- Title to the property is held by owner as:
- Fee Simple
- Elementary School:
- Waterford Elem
- High School:
- Olympia High
- Middle Or Junior School:
- Chain Of Lakes Middle
- Originally published on:
- October 1, 2026 2:56 pm
- Active on the market since:
- October 1, 2026
- Listing Agreement executed on:
- October 1, 2026
- Listing Status Last Changed On:
- October 1, 2026 2:56 pm
- Photos updated on:
- October 1, 2026 3:29 pm
- Last Modified:
- October 2, 2026 10:49 am
- Association Approval Required
- Courtesy of:
- ISLEWORTH REALTY LLC
- Attribution:
- 407-909-9000
- Road Surface Type:
- Paved
- Street Name:
- ISLEWORTH COUNTRY CLUB
- Street Number:
- 5092
- City:
- WINDERMERE
- State:
- Florida
- Zip Code:
- 34786
- County:
- Orange
- Latitude:
- N28° 29' 18.4''
- Longitude:
- W82° 28' 48.4''
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Neighborhood Stats
Source: U.S. Census Bureau, ACS 5-Year Estimates
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