Cell: (813) 474-9698
Sign Up Login

5050 Isleworth Country Club Drive, Windermere, FL 34786

$3,189,000
  • 5050 Isleworth Country Club Drive, Windermere, FL 34786 Main Photo

23 Photos

New to the Market Active
BEDS4 BATHS4 full 1 partial SQUARE FEET3,365 MLS#O6438618
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONISLEWORTH

Property Description

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 a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat.Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home's established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

5050 Isleworth Country Club Drive | MLS# O6438618

This single family home located at 5050 Isleworth Country Club Drive, Windermere, FL 34786 is currently listed for sale with an asking price of $3,189,000. This property was built in 1987 and has 4 bedrooms and 4 full and 1 partial baths with 3365 sq. ft. Isleworth Country Club Drive is located in the ISLEWORTH subdivision. Search ISLEWORTH real estate on wfeble.floridaexecutiverealty.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air, Zoned
Fenced: Yes
Garage: 2 car attached
Heating: Central, Electric, Zoned
Lot Size: 0.52 Acres
Roof Type: Concrete, Tile
Stories: 1.0
Taxes: $28,793
Year Built: 1987

Amenities

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
Lighting
Rain Gutters
Sprinkler Metered

Feature Descriptions

Additional Rooms: Den/Library/Office, Formal Dining Room Separate, Formal Living Room Separate
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
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
Directions: I-4 to Conroy Windermere Road west to Isleworth subdivision on the left. From Isleworth Country Club Drive, home is on the right.
Exterior: Block, Stucco
Fencing: Fenced
Fireplace: Living Room, Outside, Primary Bedroom
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Tile
Foundation: Block
Garage Dimensions: 31x27
HOA Fee: 3672/ Quarterly
HOA Y/N: Yes
Home Warranty Y/N: No
Listing Terms: Cash, Conventional
Lot: In County, Landscaped, On Golf Course, Paved, Private
Lot Dimensions: 0.52
Number of Septics: 1
Other Equipment: Irrigation Equipment
Ownership: Fee Simple
Parking: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized
Parking Notes: Circular Driveway, Driveway, Garage Door Opener, Gara
Patio/Porch: Covered, Rear Porch
Pets Allowed: Breed Restrictions, Cats OK, Dogs OK, Yes
Pets Restrictions: Breed restrictions and leash laws per Orange County
Pool: Gunite, Tile
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Security: Gated Community
Sewer: Septic Tank
Showing Instructions: 24 Hour Notice, Appointment Only, Call Listing Agent, Listing Agent Must Accompany
Spa: In Ground
Special Sale Provisions: None
Swimming Pool: Yes
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Phone Available, Public, Sprinkler Meter, Underground Utilities, Water Connected
Vegetation: Mature Landscaping, Oak Trees
Water: Public
Water Access Y/N: No
Windows: Blinds, Drapes, Rods, Shades, Tinted Windows
Zoning: P-D

Room Sizes

Living Room: 19x17
Dining Room: 12x16
Kitchen: 13x23
Family Room: 13x23
Den: 16x7
Bathroom 1: 5x7
Primary Bedroom: 20x20
Bedroom 2: 12x11
Bedroom 3: 13x11
Bathroom 4: 6x13
Bedroom 4: 12x12
Laundry: 6x12

Local Schools

High School: Olympia High
Middle School: Chain of Lakes Middle
Elementary School: Windermere Elem

Listed By / Shown By

Listed By

Agency Name: COMPASS FLORIDA LLC
Agency Contact: 407-203-9441

Shown By

Agent Name: Walter John Feble
Agent Phone: Cell: (813) 474-9698
Agency Title: Florida Executive Realty

IDX logo

Estimate Your Payment

Estimated Payment

$ 10,426.87 per month $7,097.33 Principal & Interest $2,399.42 Property Tax $930.13 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)
Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 09/04/2026. The listing information on this page last changed on 09/04/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 09/04/2026 12:12:26 AM EST) or Stellar MLS (last updated Thu 09/03/2026 11:55:18 PM EST). Real estate listings held by brokerage firms other than Florida Executive Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data and photos distributed by MLSGRID
Member Participants (and their affiliated licensees, if applicable) shall indicate on their websites that IDX information is provided exclusively for consumers’ personal non-commercial 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. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability.
Based on information submitted to the MLS GRID. 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.



Privacy Policy / DMCA Notice / ADA Accessibility

Login to My Homefinder