Listing provided courtesy of COMPASS FLORIDA LLCas Distributed by MLSGrid- MLS# MFRO6372348MLS Provider

5050 ISLEWORTH COUNTRY CLUB DRIVEWINDERMERE, FL 34786

Single Family · 4 Beds · 4 Full Baths · 1 Half Bath · 3,365 Sq. ft. | 0.52 Acres
$3,390,000 Active

5050 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.

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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

36
Median Age
1,680
Population Density (per sq. mile)
68%
College Educated
$103,163
Estimated Median Income
10,677
Estimated Total Home Owners
4,289
Estimated Total Renters
71% / 29%
Estimated Owner / Renter Divide
3
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

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

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

5050 ISLEWORTH COUNTRY CLUB DRIVE Market Data

Based on the last 30 days in this zip code

$2,114,906
Average List Price
$544
Average Price per Square Foot
60
Properties Sold
101
Average Days on Market
341
Properties for Sale
Calculations provided by Reliance Network

5050 ISLEWORTH COUNTRY CLUB DRIVE History

Date Event Value Agent
2/25/2026Source: My Florida Regional MLS Price Reduction
$3,390,000 -8.1%
1/24/2026Source: My Florida Regional MLS Price Reduction
$3,690,000 -7.2%
1/9/2026Source: My Florida Regional MLS Added to Database
January 09, 2026