Home in 5050 Isleworth Country Club Dr Windermere for sale with MLS# O6438618
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 Dr, Windermere, FL 34786
- Price:
- $3,189,000.00
- Original List Price:
- $3,189,000.00
- List Price per Sq Ft (Calculated, Approx.):
- $947.7
- Listing Type:
- For Sale
- Status:
- Active
- Listing Category:
- Residential
- Property Type:
- Single Family House
- MLS Number:
- O6438618
- Bedrooms:
- 4
- Bathrooms Total:
- 5
- Full Bath:
- 4
- Half Bath:
- 1
- Additional Rooms:
- Den/library/office, Formal Dining Room Separate, Formal Living Room Separate
- Living Area:
- 3,365 Sqft
- Built-Up Area:
- 4,843 Sqft
- Lot Area:
- 22,514 Sqft
- Lot Size Dimensions and Info:
- 190x151x128x145
- Building Area Source:
- Public Records
- Living Area Source:
- Public Records
- Lot Features:
- On Golf Course, Paved, In County, Private, Landscaped
- Lot Size Acres:
- 0.52
- View from the Property:
- Golf Course
- Waterfront:
- No
- Private Pool
- Swimming Pool Features:
- Gunite, Tile
- Spa
- Spa Features:
- In Ground
- Security:
- Gated Community
- Furnished:
- Negotiable
- Appliances:
- Dryer, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Gas Water Heater, Water Softener, Range, Range Hood, Tankless Water Heater, Wine Refrigerator
- Interior:
- Eat-in Kitchen, High Ceilings, Walk-In Closet(s), Built-in Features, Kitchen/family Room Combo, Stone Counters, Window Treatments, Solid Wood Cabinets, Central Vacuum, Primary Bedroom Main Floor
- Exterior:
- Lighting, Rain Gutters, Sprinkler Metered
- Patio and Porch:
- Covered, Rear Porch
- Windows:
- Blinds, Drapes, Tinted Windows, Shades, Rods
- Laundry:
- Inside, Laundry Room
- Fireplace
- Fireplace:
- Living Room, Outside, Primary Bedroom
- Air Conditioning System:
- Zoned, Central Air
- Heating System:
- Central, Electric, Zoned
- Fence:
- Fenced
- Vegetation and Trees:
- Mature Landscaping, Oak Trees
- Property Entrance Faces:
- Southeast
- Road Responsibility:
- Private Maintained Road
- Other Equipment:
- Irrigation Equipment
- Year Built:
- 1987
- Roof:
- Concrete, Tile
- Levels:
- One
- Construction Materials:
- Block, Stucco
- Flooring:
- Tile
- Foundation Details:
- Block
- Flood Zone Code:
- X
- Tax Annual Amount:
- $28,793.00
- Tax Year:
- 2025
- Association Fee:
- $3,672.00
- Association Fee Frequency:
- Quarterly
- Total Annual Fees:
- $14,688.00
- Total Monthly Fees:
- $1,224.00
- Garage
- Garage Spaces:
- 2
- Attached Garage
- Parking Features:
- Driveway, Garage Door Opener, Circular Driveway, Oversized, Garage Faces Rear, Golf Cart Parking
- Garage Dimensions:
- 31x27
- Sewer:
- Septic Tank
- Utilities Available:
- Cable Available, Underground Utilities, Phone Available, Electricity Connected, Natural Gas Connected, Water Connected, Public, Broadband/High Speed Internet Available, Sprinkler Meter
- Water Source:
- Public
- Association
- Minimum Lease Term:
- 7 Months
- Pets Allowed?:
- Yes, Breed Restrictions, Dogs Ok, Cats Ok
- Amenities Provided by the Homeowner's Association (HOA):
- Playground, Security, Basketball Court, Gated, Fence Restrictions, Vehicle Restrictions, Cable Tv, Optional Additional Fees
- Subdivision Name:
- ISLEWORTH
- Community Features:
- Clubhouse, Fitness Center, Street Lights, Pool, Tennis Court(s), Golf, Playground, Restaurant, Association Recreation - Owned, Irrigation-reclaimed Water, Golf Carts Ok, Community Mailbox, Special Community Restrictions, Gated Community - Guard
- Association Fee Includes:
- Maintenance Grounds, Cable Tv, Security, Escrow Reserves Fund, Guard - 24 Hour, Private Road, Maintenance
- Senior Community:
- No
- Association Fee Required:
- Required
- Planned Unit Development
- Association Management:
- Dan O'Connell
- Association Phone:
- 407-909-2071
- Listing Terms Considered by Seller:
- Cash, Conventional
- Occupant Type:
- Owner
- Buyer Possession:
- Close Of Escrow
- Lease Considered:
- Yes
- Tax Legal Description:
- ISLEWORTH 16/118 LOT 41
- Real Estate Folio Number (Parcel Number):
- 16-23-28-3899-00-410
- Zoning:
- P-D
- Title to the property is held by owner as:
- Fee Simple
- Elementary School:
- Carrollwood K-8 School
- High School:
- Olympia High
- Middle Or Junior School:
- Chain Of Lakes Middle
- Originally published on:
- September 4, 2026 10:44 am
- Active on the market since:
- September 4, 2026
- Listing Agreement executed on:
- August 28, 2026
- Price change occurred on:
- September 4, 2026 10:44 am
- Listing Status Last Changed On:
- September 4, 2026 10:44 am
- Photos updated on:
- September 4, 2026 10:47 am
- Last Modified:
- September 5, 2026 10:48 am
- Association Approval Required
- Courtesy of:
- COMPASS FLORIDA LLC
- Attribution:
- 407-203-9441
- Road Surface Type:
- Asphalt
- Street Name:
- ISLEWORTH COUNTRY CLUB
- Street Number:
- 5050
- City:
- WINDERMERE
- State:
- Florida
- Zip Code:
- 34786
- County:
- Orange
- Latitude:
- N28° 29' 27.1''
- Longitude:
- W82° 28' 50.4''
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Neighborhood Stats
Source: U.S. Census Bureau, ACS 5-Year Estimates
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