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$8,500,000 Just Listed
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Full Property Details for 5092 Isleworth Country Club Dr
General
- Price: $8,500,000
- HOA FEE: $1,224/month
- HOA FEE FREQ.: Quarterly
- Taxes: $57,070 (2026)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6446272
- Updated: 10/1/2026
- Added to Site: 1 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 5
- Interior Features: Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Central Vacuum, Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments
- Fireplace: Yes
- Fireplace(s): Living Room, Master Bedroom
- 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
- Furnishings: Negotiable
- Flooring: Brick/Stone, Carpet, Marble, Travertine, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 5
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Laundry Room
Additional Information
- Shared Amenities: Cable TV, Gated, Maintenance, Optional Additional Fees, Playground, Security
- Pool: Yes
- Private Pool: Yes
- Pool Description: In Ground, Lighting
- Spa: Yes
- Spa Description: Heated, In Ground
- Security/Safety: Closed Circuit Camera(s), Gated Community, Security Gate, Security Lights, Security System, Smoke Detector(s)
Exterior
- Exterior Features: Balcony, French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 4
- Covered Spaces: 4
- Parking Features: Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
Location
- Area: 34786 - Windermere
- County: Orange
- Development Name: 34786 - Windermere
- Subdivision: ISLEWORTH
- Driving 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.
- Direction Faces: East
School Information
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
Community
- Community Name: 34786 - Windermere
- Community Features: Association Recreation - Owned, Community Mailbox, Fitness Center, Golf Carts OK, Golf, Playground, Pool, Tennis Court(s)
- Optional Amenities: Cable TV, Gated, Maintenance, Optional Additional Fees, Playground, Security
- Association: Yes
- Assoc. Name: Dan O’Connell
- Assoc. Fees Include: 24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Private Road, Security
- Pet Restrictions: Per Orange County breed restrictions, number limits and leash laws.
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Central, Zoned
Utilities
- Sewer: Septic Tank
- Water District: BUTLER CHAIN OF LAKES
- Water: Public
- Utility Description: Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Street Lights, Underground Utilities
Structural Information
- Architectural Info: Mediterranean
- Architectural Style: Mediterranean
- Exterior Const.: Block, Stucco
- Roof: Tile
- Windows: Drapes, Shutters, Window Treatments
- Stories/Levels: Two
- Square Feet: 7,100
- Sq. Ft. Source: Owner
- Year Built: 1995
Lot Features
- Property View: Garden, Golf Course, Trees/Woods, Water
- Lot Size (Acres): 0.93
- Lot Size (Sq. Ft.): 40,620
- Lot Size: 40620
- Frontage: Street Paved, Private Road
- Street/Road Desc.: Paved
- Fencing (Description): Fenced
Water Features
- Water View: Yes
- Water Front Name: BUTLER CHAIN OF LAKES
Financial Considerations
- Association Fee: $3,672
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $57,070.63
- Tax Year: 2026
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: N 73 DEG W 204.27 FT S 22 DEG W ALONG LOTS 47 & 48 FOR 146.32 FT TO POB
- Flood Zone Info: X
- APN: 162328389900480
- Property ID: 162328389900480
Listed by Isleworth Realty Llc
Schools serving 5092 Isleworth Country Club Dr
| Name | Grades | Distance |
|---|---|---|
Windermere Elementary School 11125 Park Avenue, Windermere, FL 34786 | K-5 | 2 mi |
Chain Of Lakes Middle School 8700 Conroy Windermere Road, Orlando, FL 32835 | 6-8 | 1 mi |
Olympia High School 4301 South Apopka Vineland Road, Orlando, FL 32835 | 9-12 | 1.1 mi |
Price & Sales History for 5092 Isleworth Country Club Dr
Tax History for 5092 Isleworth Country Club Dr
Estimate the Cost for 5092 Isleworth Country Club Dr
5092 Isleworth Country Club Drive, Windermere, FL 34786 (MLS# O6446272) is a Single Family property with 4 bedrooms and 5 full bathrooms. 5092 Isleworth Country Club Drive is currently listed for $8,500,000 and was received on October 01, 2026. Want to learn more about 5092 Isleworth Country Club Drive? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.

