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WINDERMERE, FL 34786 5050 ISLEWORTH COUNTRY CLUB DRIVE

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Presented By: COMPASS FLORIDA LLC with 407-203-9441. - 407-203-9441
  • MLS# O6372348
  • 01/03/2026
  • Request Tour
  • Request Info
  • Beds • 4
  • Full/Half Baths • 4 / 1
  • SQFT • 3,365
  • Garage • 2

Home Details

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.
Presented By: COMPASS FLORIDA LLC with 407-203-9441. - 407-203-9441

Interior Features for 5050 ISLEWORTH COUNTRY CLUB DRIVE

Bedrooms

Total Bedrooms4

Bathrooms

Half Baths1
Total Baths5

Other Interior Features

LivingAreaSourcePublic Records
Air Conditioning Y/NYes
Fireplace FeaturesLiving Room, Outside, Master Bedroom
Fireplace Y/NYes
FlooringPorcelain Tile
Furnished Y/NNegotiable
Heating Y/NYes
Interior AmenitiesBuilt-in Features, Central Vacuum, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s), Window Treatments
Laundry FeaturesInside, Laundry Room
Window FeaturesBlinds, Drapes, Rods, Shades, Tinted Windows

General for 5050 ISLEWORTH COUNTRY CLUB DRIVE

Additional Parcels Y/NNo
Additional RoomsDen/Library/Office, Formal Dining Room Separate, Formal Living Room Separate
AppliancesDishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
Assoc Fee Paid PerQuarterly
Association AmenitiesBasketball Court, Cable TV, Fence Restrictions, Gated, Optional Additional Fees, Playground, Security, Vehicle Restrictions
Association Fee Includes24-Hour Guard, Cable TV, Escrow Reserves Fund, Maintenance Grounds, Maintenance Repairs, Private Road, Security
Association NameDan O'Connell
Attached Garage Yes
Building Area UnitsSquare Feet
Carport Y/NNo
CityWINDERMERE
Community FeaturesCommunity Boat Ramp, Lake, Water Access, Waterfront, 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)
Construction MaterialsBlock, Stucco
CoolingCentral Air, Zoned
CountyOrange
DirectionsI-4 to Conroy Windermere Road west to Isleworth subdivision on the left. From Isleworth Country Club Drive, home is on the right.
Elementary SchoolWindermere Elem
Facing DirectionSoutheast
Flood Zone CodeX
Flood Zone Code XY
Full Baths4
Garage Spaces2
Garage Y/NYes
HOA Fee$3129
HeatingCentral, Electric, Zoned
High SchoolOlympia High
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionISLEWORTH 16/118 LOT 41
LevelsOne
Listing TermsCash, Conventional
Living Area UnitsSquare Feet
Lot Size Square Feet22514
Lot Size UnitsSquare Feet
MLS Area34786 - Windermere
Middle/Junior High SchoolChain of Lakes Middle
Minimum Lease7 Months
Monthly HOA Amount1043
New ConstructionNo
Occupancy TypeOwner
OwnershipFee Simple
Patio/Porch FeaturesCovered, Rear Porch
Pets AllowedBreed Restrictions, Cats OK, Dogs OK, Yes
Pool FeaturesGunite, Tile
PossessionClose Of Escrow
Property Attached Y/NNo
Property SubtypeSingle Family Residence
Property TypeResidential
RoofTile, Concrete
STELLAR_InLawSuiteYNNo
Security FeaturesGated Community
Senior Community Y/NNo
SewerSeptic Tank
Spa FeaturesIn Ground
Standard StatusActive
StatusActive
Subdivision NameISLEWORTH
Tax Annual Amount28793
Tax Lot41
Tax Year2025
Total Rooms13
UtilitiesBB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Phone Available, Public, Sprinkler Meter, Street Lights, Underground Utilities, Water Connected
ViewGolf Course
Virtual TourClick here
Water Access Y/NNo
Water View Y/NNo
Waterfront FeaturesLake, Waterfront
Year Built1987
ZoningP-D

Exterior for 5050 ISLEWORTH COUNTRY CLUB DRIVE

Building Area Total4843
Covered Spaces2
Exterior AmenitiesIrrigation System, Lighting, Rain Gutters, Sliding Doors, Sprinkler Metered
FencingFenced
Foundation DetailsBlock
Lot Dimensions190 x 151 x 128 x 145
Lot FeaturesOn Golf Course, In County, Landscaped
Lot Size Acres0.52
Lot Size Area22514
Parking FeaturesGolf Cart Parking, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Oversized
Private PoolYes
Road Frontage TypePrivate Road, Street Paved
Road ResponsibilityPrivate Maintained Road
Road Surface TypePaved, Asphalt
SpaYes
VegetationMature Landscaping, Oak Trees
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Steven Silcock

Broker Owner
Price $3,390,000
MLS#O6372348
List Date 01/03/2026
Property Type Single Family
Phone 407.574.0218
Request Tour
Request Info
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