

5050 ISLEWORTH COUNTRY CLUB DRIVEWINDERMERE, FL 34786
Single Family · 4 Beds · 4 Full Baths · 1 Half Bath · 3,365 Sq. ft. | 0.52 Acres5050 ISLEWORTH COUNTRY CLUB DRIVE Overview
- Time on Site:
- 171 days
- Visits:
- 2
Situated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout and modern chandeliers. This single-story residence was renovated in 2020 featuring a new tile roof, fresh paint inside and out, all bathrooms updated and a fully renovated kitchen. Spanning over 3,300 square feet, the 4-bedroom, 4.5-bath is nestled in the heart of Windermere, Florida. The foyer with groin ceiling is light and bright as natural light floods into the home from the glass entryway. Arched details abound in the entrance and this staple in Mediterranean design is carried throughout the estate. Two steps down into the sunken formal living room, the gas fireplace is the centerpiece featuring an artistic stone slab above the hearth and framed by wall-to-wall stacked stone. Completing the space are four large arched windows, two arched doors providing access to the back garden and a built-in dry bar. Situated between the family room and formal living room, and serviced by the nearby kitchen, the formal dining room offers the same illumination of natural sunlight from two large arched windows. The kitchen features new KitchenAid stainless steel appliances, a NXR Pro gas range and built-in 40 bottle Euro Cave wine fridge. The custom cabinetry provides ample storage and tastefully pairs in a dark grey-brown tone with the white tile backsplash, multi-tonal grey to white tile range hood and marble counters with soft neutral veins. The custom cabinetry continues seamlessly into the family room with built-in entertainment center. Down the hall from the kitchen and family room are the guest rooms. The first features an ensuite bathroom and the other two bedrooms are serviced by the hall bath with dual sinks. The hall bath also provides access to the patio and serves as the pool bath. Situated on the opposite end of the home, we find the primary suite, powder bath off the foyer and a flex room. The primary is airy and bright with arched windows, stacked stone fireplace and a dazzling chandelier. The suite features two separate bathrooms – one with walk-in shower and the second with free-standing soaking tub. The walk-in closet offers a warm cedar wood ceiling and custom built-ins. The flex room proposes many uses whether it be an office, nursery, gym, den or library. This stunning property offers a seamless blend of indoor-outdoor living boasting a covered patio with fireplace, open-air pool with spa and views of the fairway. Rounding out the estate is a welcoming circular driveway that extends to the rear motor court with two-car garage plus golf cart parking. Whether hosting or unwinding, this home elevates every moment.
5050 ISLEWORTH COUNTRY CLUB DRIVE Facts & Features
- Type Single Family
- Sq. ft. 3,365
- Price/Sq.ft. $1,007
- Lot 0.52 Acres
Details
General
Association/HOA
- Association Amenities: Basketball Court,Cable TV,Fence Restrictions,Gated,Optional Additional Fees,Playground,Security,Vehicle Restrictions
- Association Fee: 3129
- Association Fee Frequency: Quarterly
- Association Fee Includes: Guard - 24 Hour,Cable TV,Escrow Reserves Fund,Maintenance Grounds,Maintenance,Private Road,Security
- Association Name: Dan O'Connell
- Association: Yes
School Information
- Elementary School: Windermere Elem
- Middle Or Junior School: Chain of Lakes Middle
- High School: Olympia High
Building Information
- New Construction: No
- Year Built: 1987
Location/Region
- Country: US
- County Or Parish: Orange
- MLS Area Major: 34786 - Windermere
- Subdivision Name: ISLEWORTH
- Township: 23
Community/Development
- 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
Tax Information
- Tax Annual Amount: 28793
- Tax Year: 2025
General Information
- Furnished: Negotiable
- Listing Terms: Cash,Conventional
- Ownership: Fee Simple
- Parcel Number: 16-23-28-3899-00-410
- Pets Allowed: Breed Restrictions,Cats OK,Dogs OK,Yes
- Property Sub Type: Single Family Residence
- Property Type: Residential
- Senior Community: No
- Special Listing Conditions: None
- Zoning: P-D
Interior
Parking Information
- Garage Spaces: 2
- Garage: Yes
Beds/Baths
- Bathrooms Full: 4
- Bathrooms Half: 1
- Bathrooms Total: 5
- Bedrooms Total: 4
Building Interior
- Building Area Source: Public Records
- Building Area Total: 4843
- Building Area Units: Square Feet
General Information
- Appliances: Dishwasher,Disposal,Dryer,Gas Water Heater,Microwave,Range,Range Hood,Refrigerator,Tankless Water Heater,Washer,Water Softener,Wine Refrigerator
- Cooling: Central Air,Zoned
- Fireplace Features: Living Room,Outside,Primary Bedroom
- Fireplace: Yes
- Flooring: Tile
- Foundation Details: Block
- Heating: Central,Electric,Zoned
- 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
- Living Area: 3365
- Living Area Source: Public Records
- Living Area Units: Square Feet
- Other Equipment: Irrigation Equipment
- Security Features: Gated Community
- Spa Features: In Ground
- Spa: Yes
- Window Features: Blinds,Drapes,Rods,Shades,Tinted Windows
Exterior
Parking Information
- Parking Features: Golf Cart Parking,Circular Driveway,Driveway,Garage Door Opener,Garage Faces Rear,Oversized
Lot Information
- Additional Parcels: No
- Lot Features: Private,On Golf Course,In County,Paved,Landscaped
- Lot Size Acres: 0.52
- Lot Size Dimensions: 190x151x128x145
- Lot Size Square Feet: 22514
- Road Responsibility: Private Maintained Road
- Road Surface Type: Asphalt
- Vegetation: Mature Landscaping,Oak Trees
- Water Source: Public
Waterfront/View
- View: Golf Course
- Waterfront: No
Building Exterior/Construction
- Attached Garage: Yes
- Construction Materials: Block,Stucco
- Direction Faces: Southeast
- Patio And Porch Features: Covered,Rear Porch
- Property Attached: No
- Roof: Tile,Concrete
General Information
- Carport: No
- Exterior Features: Lighting,Rain Gutters,Sliding Doors,Sprinkler Metered
- Fencing: Fenced
- Pool Features: Gunite,Tile
- Pool Private: Yes
- Sewer: Septic Tank
- Utilities: BB/HS Internet Available,Cable Available,Electricity Connected,Natural Gas Connected,Phone Available,Public,Sprinkler Meter,Underground Utilities,Water Connected
Room Information
Room: Bathroom 1
- Level: First
- Dimensions: 5x7
- Length: 7
- Width: 5
- Features: Single Vanity,Window/Skylight in Bath
Room: Bathroom 4
- Level: First
- Dimensions: 6x13
- Length: 13
- Width: 6
- Features: Double Vanity,Shower No Tub,Stone Counters
Room: Bedroom 2
- Level: First
- Dimensions: 12x11
- Length: 11
- Width: 12
- Features: En Suite Bathroom,Single Vanity,Stone Counters
Room: Bedroom 3
- Level: First
- Dimensions: 13x11
- Length: 11
- Width: 13
Room: Bedroom 4
- Level: First
- Dimensions: 12x12
- Length: 12
- Width: 12
Room: Den
- Level: First
- Dimensions: 16x7
- Length: 7
- Width: 16
- Features: Built-In Shelving
Room: Dining Room
- Level: First
- Dimensions: 12x16
- Length: 16
- Width: 12
Room: Family Room
- Level: First
- Dimensions: 13x23
- Length: 23
- Width: 13
- Features: Built-In Shelving
Room: Kitchen
- Level: First
- Dimensions: 13x23
- Length: 23
- Width: 13
- Features: Built-In Shelving,Stone Counters,Walk-In Pantry
Room: Laundry
- Level: First
- Dimensions: 6x12
- Length: 12
- Width: 6
- Features: Built-In Shelving,Single Vanity
Room: Living Room
- Level: First
- Dimensions: 19x17
- Length: 17
- Width: 19
- Features: Bar
Room: Primary Bathroom
- Level: First
- Features: Garden Bath,Makeup/Vanity Space,Stone Counters,Window/Skylight in Bath
Room: Primary Bedroom
- Level: First
- Dimensions: 20x20
- Length: 20
- Width: 20
- Features: Built-In Shelving,En Suite Bathroom,Multiple Shower Heads,Split Vanities
5050 ISLEWORTH COUNTRY CLUB DRIVE Neighborhood
Community
34786 (WINDERMERE) Demographics
Schools
School data unavailable, School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.5050 ISLEWORTH COUNTRY CLUB DRIVE Monthly Cost
5050 ISLEWORTH COUNTRY CLUB DRIVE Market Data
Based on the last 30 days in this zip code
5050 ISLEWORTH COUNTRY CLUB DRIVE History
| Date | Value | Agent |
|---|---|---|
| 2/25/2026Source: My Florida Regional MLS | $3,390,000 -8.1% |
|
| 1/24/2026Source: My Florida Regional MLS | $3,690,000 -7.2% |
|
| 1/9/2026Source: My Florida Regional MLS | January 09, 2026 |

