$3,390,000

5050 Isleworth Country Club Drive, Windermere, FL 34786

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$3,390,000

(300,000) 02/25/2026

5050 Isleworth Country Club Drive Windermere, FL 34786

For Sale MLS# O6372348

4 beds 5 baths 3,365 sq ft Single Family

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Data current as of 08/06/2026 19:29:01

Details for 5050 Isleworth Country Club Drive

MLS# O6372348

Description for 5050 Isleworth Country Club Drive, Windermere, FL, 34786


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.

Listing Information


Property Type: Residential, Single Family Residence

Status: Active

Bedrooms: 4

Bathrooms: 5

Lot Size: 0.52 Acres

Square Feet: 3,365 sq ft

Year Built: 1987

Garage: Yes

Stories: 1 Story

Construction: Block,Stucco

Subdivision: Isleworth

Foundation: Block

County: Orange

School Information


Elementary: Windermere Elem

Middle: Chain Of Lakes Middle

High: Olympia High

Room Information


Main Floor

Living Room: 17x19

Bedroom 3: 11x13

Bathroom 4: 13x6

Bedroom 4: 12x12

Laundry: 12x6

Dining Room: 16x12

Kitchen: 23x13

Family Room: 23x13

Den: 7x16

Bathroom 1: 7x5

Primary Bedroom: 20x20

Primary Bathroom:

Bedroom 2: 11x12

Bathrooms

Full Baths: 4

1/2 Baths: 1

Additonal Room Information

Laundry: Inside, Laundry Room

Interior Features


Appliances: Wine Refrigerator, Range Hood, Tankless Water Heater, Water Softener, Gas Water Heater, Range, Refrigerator, Microwave, Dishwasher, Disposal, Dryer, Washer

Flooring: Porcelain Tile

Doors/Windows: Blinds, Window Treatments, Tinted Windows, Drapes, Rods

Fireplaces: Living Room, Outside, Primary Bedroom

Additional Interior Features: Eat-In Kitchen, Central Vacuum, Window Treatments, Walk-In Closet(s), Built-in Features, High Ceilings, Separate/Formal Dining Room, Wood Cabinets, Main Level Primary, Kitchen/Family Room Combo, Separate/Formal Living Room, Stone Counters

Utilities


Water: Public

Sewer: Septic Tank

Other Utilities: Cable Available,Electricity Connected,Natural Gas Connected,High Speed Internet Available,Municipal Utilities,Phone Available,Underground Utilities,Water Connected

Cooling: Zoned, Central Air

Heating: Central, Electric, Zoned

Exterior / Lot Features


Attached Garage: Attached Garage

Garage Spaces: 2

Parking Description: driveway, Golf Cart Garage, Circular Driveway, Garage, Garage Door Opener, Oversized, Garage Faces Rear

Roof: Tile, Concrete

Pool: Tile, Gunite, Community

Lot View: Golf Course

Lot Dimensions: 190x151x128x145

Fencing: fenced

Additional Exterior/Lot Features: Sprinkler/Irrigation, Rain Gutters, Lighting, Covered, Rear Porch, On Golf Course, Landscaped, Private Road, Outside City Limits

Community Features


Community Features: Fitness, Golf Carts OK, Recreation Area, Water Access, Community Mailbox, Lake, Clubhouse, Golf, Pool, Tennis Court(s), Playground, Waterfront, Street Lights, Boat Facilities, Gated, Restaurant

Security Features: Gated Community, Gated with Guard

Association Amenities: Cable TV, Security, Playground, Gated, Basketball Court

HOA Dues Include: Maintenance Grounds, Reserve Fund, Road Maintenance, Security, Cable TV, Maintenance Structure

Homeowners Association: Yes

HOA Dues: $3,129 / Quarterly

Driving Directions


I-4 to Conroy Windermere Road west to Isleworth subdivision on the left. From Isleworth Country Club Drive, home is on the right.

Financial Considerations


Terms: Cash,Conventional

Tax/Property ID: 16-23-28-3899-00-410

Tax Amount: 28793

Tax Year: 2025

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Interest rate and annual percentage rate (APR) are based on current market conditions, are for informational purposes only, are subject to change without notice and may be subject to pricing add-ons related to property type, loan amount, loan-to-value, credit score and other variables. Estimated closing costs used in the APR calculation are assumed to be paid by the borrower at closing. If the closing costs are financed, the loan, APR and payment amounts will be higher. If the down payment is less than 20%, mortgage insurance may be required and could increase the monthly payment and APR. Contact us for details. Additional loan programs may be available. Accuracy is not guaranteed, and all products may not be available in all borrower's geographical areas and are based on their individual situation. This is not a credit decision or a commitment to lend.

Sales History

Date Price
Currently not available.

Tax Summary

Tax Year Estimated Market Value Total Tax
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Schools nearby 5050 Isleworth Country Club Drive

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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.

The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.

SchoolDigger ® Rating

The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.

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