$3,189,000
5050 Isleworth Country Club Drive
Windermere, FL 34786
Listing updated: September 5, 2026 at 6:48 AM ET
Listing courtesy of Compass Florida Llc · Toni Cafferty · MLS #O6438618 · Active · 407-203-9441Property type
Year built
Lot size
Price / sq ft
HOA dues
Day on market
Garage spaces
Flood zone
About this home
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history1 days on market
- Status: ActiveSep 4, 2026
- Listed$3,189,000Sep 4, 2026
- Price increased$3,189,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 1
- Subdivision
- Isleworth
- County
- Orange
- Year built
- 1987
- Living area
- 3,365 sq ft
- Price/sq ft
- $948
- Building area
- 4,843 sq ft (Public Records)
- Lot size
- 22,514 sq ft
- Lot category
- 1/2 to less than 1
- Flood zone
- X
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $28,793 (2025)
- Parcel #
- 16-23-28-3899-00-410
- Zoning
- P-D
- MLS #
- O6438618
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 4
- Half bathrooms
- 1
- Flooring
- Tile
- Appliances
- Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
- 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
- Inside, Laundry Room
- Stories / Levels
- One
- Direction faces
- Southeast
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central, Electric, Zoned
- Cooling
- Central Air, Zoned
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized
HOA & Financial
- HOA fee
- $3,672 / Quarterly
- Monthly HOA
- $1,224/mo
- Total monthly fees
- $1,224/mo
- Total annual fees
- $14,688
- HOA name
- Dan O'Connell
- CDD
- No
- Min lease term
- 7 Months
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Per Isleworth Community Association (ICA)
- Approval process
- Per Isleworth Community Association (ICA)
Exterior & Construction
- Exterior features
- Lighting, Rain Gutters, Sprinkler Metered
- Construction materials
- Block, Stucco
- Roof
- Concrete, Tile
- Foundation
- Block
- Pool
- Private pool
- Road surface
- Asphalt
Utilities
- Sewer
- Septic Tank
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Phone Available, Public, Sprinkler Meter, Underground Utilities, Water Connected
Community
- Pets allowed
- Breed Restrictions, Cats OK, Dogs OK, Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Living Room | First | 19x17 |
| Dining Room | First | 12x16 |
| Kitchen | First | 13x23 |
| Family Room | First | 13x23 |
| Den | First | 16x7 |
| Bathroom 1 | First | 5x7 |
| Primary Bedroom | First | 20x20 |
| Primary Bathroom | First | |
| Bedroom 2 | First | 12x11 |
| Bedroom 3 | First | 13x11 |
| Bathroom 4 | First | 6x13 |
| Bedroom 4 | First | 12x12 |
| Laundry | First | 6x12 |
Listing Details
- Listing date
- 2026-08-28
- On market date
- 2026-09-04
- Original list price
- $3,189,000
- Occupant type
- Owner
- MLS area
- 34786 - Windermere
- Listing AOR
- Osceola
- Status changed
- 2026-09-04
- Tax legal description
- ISLEWORTH 16/118 LOT 41
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
I-4 to Conroy Windermere Road west to Isleworth subdivision on the left. From Isleworth Country Club Drive, home is on the right.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
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Based on information submitted to the MLS GRID as of September 5, 2026 at 6:48 AM ET. 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.
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