5050 ISLEWORTH COUNTRY CLUB DRIVE
Windermere, FL 34786
$3,189,000
Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests.
Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home.
The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room.
The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with ...
+ Read More
Listing Courtesy of: COMPASS FLORIDA LLC
407-203-9441
| Listing Id: | O6438618 |
|---|---|
| List Price: | $3,189,000 |
| Property Type: | Residential |
| Property Sub Type: | Single Family Residence |
| Status: | Active |
| Bedrooms Total: | 4 |
| Bathrooms Full: | 4 |
| Bathrooms Half: | 1 |
| Living Area: | 3,365 |
| Tax Annual Amount: | $28,793 |
| Lot Size Square Feet: | 22,514 |
| Lot Size Acres: | 0.52 |
| Waterfront?: | No |
| City: | Windermere |
| County Or Parish: | Orange |
| Subdivision Name: | Isleworth |
| Postal Code: | 34786 |
| Year Built: | 1987 |
| Appliances: | Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator |
| Association Amenities: | Basketball Court, Cable TV, Fence Restrictions, Gated, Optional Additional Fees, Playground, Security, Vehicle Restrictions |
| Association Fee: | $3,672 |
| Association Fee Frequency: | Quarterly |
| Association Fee Includes: | Guard - 24 Hour, Cable TV, Escrow Reserves Fund, Maintenance Grounds, Maintenance, Private Road, Security |
| Attached Garage?: | Yes |
| Bathrooms Total Integer: | 5 |
| Building Area Source: | Public Records |
| Building Area Total: | 4843 |
| Building Area Units: | Square Feet |
| Direction Faces: | Southeast |
| Foundation Details: | Block |
| Construction Materials: | Block, Stucco |
| Cooling: | Central Air, Zoned |
| Fireplace Features: | Living Room, Outside, Primary Bedroom |
| Directions: | I-4 to Conroy Windermere Road west to Isleworth subdivision on the left. From Isleworth Country Club Drive, home is on the right. |
| Elementary School: | Windermere Elem |
| Exterior Features: | Lighting, Rain Gutters, Sprinkler Metered |
| Fencing: | Fenced |
| Flooring: | Tile |
| Furnished: | Negotiable |
| Garage Spaces: | 2 |
| Garage?: | Yes |
| Community Features: | Association Recreation - Owned, Clubhouse, Community Mailbox, Fitness Center, Gated Community - Guard, Golf Carts OK, Golf, Irrigation-Reclaimed Water, Playground, Pool, Restaurant, Special Community Restrictions, Tennis Court(s), Street Lights |
| Heating: | Central, Electric, Zoned |
| High School: | Olympia High |
| Interior Features: | Built-in Features, Central Vaccum, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s), Window Treatments |
| Laundry Features: | Inside, Laundry Room |
| Levels: | One |
| Ownership: | Fee Simple |
| Living Area Source: | Public Records |
| Living Area Units: | Square Feet |
| Lot Features: | In County, Landscaped, On Golf Course, Paved, Private |
| Lot Size Acres: | 0.52 |
| Lot Size Dimensions: | 190x151x128x145 |
| Middle Or Junior School: | Chain of Lakes Middle |
| MLS Area Major: | 34786 - Windermere |
| MLS Area Major: | 34786 - Windermere |
| Original List Price: | $3,189,000 |
| Other Equipment: | Irrigation Equipment |
| Parcel Number: | 16-23-28-3899-00-410 |
| Parking Features: | Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized |
| Patio And Porch Features: | Covered, Rear Porch |
| Pets Allowed: | Breed Restrictions, Cats OK, Dogs OK, Yes |
| Pool Features: | Gunite, Tile |
| Township: | 23 |
| Road Surface Type: | Asphalt |
| Roof: | Concrete, Tile |
| Listing Terms: | Cash, Conventional |
| Tax Year: | 2025 |
| Security Features: | Gated Community |
| Sewer: | Septic Tank |
| Special Listing Conditions: | None |
| State Or Province: | FL |
| Association?: | Yes |
| Utilities: | BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Phone Available, Public, Sprinkler Meter, Underground Utilities, Water Connected |
| View: | Golf Course |
| Water Source: | Public |
| Public Survey Range: | 28 |
| Public Survey Section: | 16 |
| Zoning: | P-D |
| Possession: | Close Of Escrow |
| Spa Features: | In Ground |
| Spa?: | Yes |
| Vegetation: | Mature Landscaping, Oak Trees |
| Window Features: | Blinds, Drapes, Rods, Shades, Tinted Windows |
| Additional Lease Restrictions: | Per Isleworth Community Association (ICA) |
| Additional Rooms: | Den/Library/Office, Formal Dining Room Separate, Formal Living Room Separate |
| Amenities Additional Fees: | Membership to Isleworth Golf & Country Club offers amenities at a separate charge. |
| Approval Process: | Per Isleworth Community Association (ICA) |
| Association Approval Required Yn: | Yes |
| Association Email: | dan.oconnell@isleworth.com |
| Association Fee Requirement: | Required |
| Available For Lease Yn: | Yes |
| Building Area Total Srch Sq M: | 449.93 |
| Calculated List Price By Calcula: | 947.70 |
| Cddyn: | No |
| Dprurl: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6438618?w=Agent&skip_sso=true |
| Dprurl 2: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6438618?w=Customer |
| Dpryn: | No |
| Exist Lse Tenant Yn: | No |
| Flood Zone Code: | X |
| Garage Dimensions: | 31x27 |
| Green Verification Count: | 0 |
| Homestead Yn: | No |
| Lease Restrictions Yn: | Yes |
| Listing Exclusion Yn: | No |
| Living Area Meters: | 312.62 |
| Lot Size Square Meters: | 2092 |
| Minimum Lease: | 7 Months |
| Monthly Hoa Amount: | $1,224 |
| Number Of Septics: | 1 |
| Pet Restrictions: | Breed restrictions and leash laws per Orange County |
| Planned Unit Development Yn: | Yes |
| Realtor Info: | Assoc approval required, Floor Plan Available, No Sign, Owner Motivated |
| Room Count: | 13 |
| Sdeo yn: | No |
| Total Acreage: | 1/2 to less than 1 |
| Total Annual Fees: | $14,688 |
| Total Monthly Fees: | $1,224 |
| Unit Number Yn: | No |
| Water Access Yn: | No |
| Water Extras Yn: | No |
| Water View: | No |
| Yrs Of Owner Prior To Leasing Re: | 0 |
| Road Responsibility: | Private Maintained Road |
| Association Name: | Dan O'Connell |
| Association Phone: | 407-909-2071 |
| Association 2 Yn: | 0 |
| Attribution Contact: | 407-203-9441 |
| Originating System Name : | Stellar MLS |
| Community Association Water Features: | Community Boat Ramp, Lake, Water Access, Waterfront |
| In Law Suite Yn: | No |
| Green Energy Generation Yn: | No |
| Listing Contract Date: | 2026-08-28 |
| Fireplace?: | Yes |
| Pool Private?: | Yes |
Mortgage Calculator
Copyright 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. Information deemed reliable but is not guaranteed. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of My Florida Regional MLS DBA Stellar MLS. Real estate listings held by brokerage firms other than the owner of this page include the name of the listing broker. Information provided is for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. This site will be monitored for 'scraping' and any use of search facilities of data on the site other than by a consumer looking to purchase real estate is prohibited. Listing broker has attempted to offer accurate data, but buyers are advised to confirm all items. Information last updated on October 20, 2026 11:04 PM - ET
Based on information submitted to the MLS GRID as of October 20, 2026 11:04 PM - ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. Some listings have been excluded from this website.
IDX information is provided exclusively for consumers’ personal noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time.
Property Last Updated: October 20, 2026 11:04 PM - ET
