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.
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.
Property Details
Price:
$3,189,000
MLS #:
O6438618
Status:
Active
Beds:
4
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLEWORTH
Neighborhood:
34786windermere
Listed Date:
Sep 4, 2026
Finished Sq Ft:
3,365
Total Sq Ft:
4,843
Lot Size:
22,514 sqft / 0.52 acres (approx)
Year Built:
1987
See this Listing
Schools
Elementary School:
Windermere Elem
Middle School:
Chain of Lakes Middle
High School:
Olympia High
Interior
Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Porcelain Tile
Heating
Central, Electric, Zoned
Interior Features
Built-in Features, Central Vacuum, Eating Space 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
Exterior
Association Amenities
Basketball Court, Cable TV, Fence Restrictions, Gated, Optional Additional Fees, Playground, Security, Vehicle Restrictions
Attached Garage YN
1
Community Features
Community Boat Ramp, Lake, Water Access, Waterfront, 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)
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
Southeast
Exterior Features
Irrigation System, Lighting, Rain Gutters, Sliding Doors, Sprinkler Metered
Fencing
Fenced
Garage Spaces
2
Lot Features
In County, Landscaped, On Golf Course
Open Parking YN
1
Parking Features
Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized
Patio And Porch Features
Covered, Rear Porch
Roof
Concrete, Tile
Security Features
Gated Community
Spa Features
In Ground
View
Golf Course
Waterfront Features
Lake, Waterfront
Window Features
Blinds, Drapes, Rods, Shades, Tinted Windows
Financial
HOA Fee
$3,672
HOA Fee Frequency
Quarterly
HOA Includes
24-Hour Guard, Cable TV, Escrow Reserves Fund, Maintenance Grounds, Maintenance Repairs, Private Road, Security
HOA Name
Dan O’Connell
HOA Phone
407-909-2071
Tax Year
2025
Taxes
$28,793
Map
Community
- Address5050 ISLEWORTH COUNTRY CLUB DRIVE WINDERMERE FL
- SubdivisionISLEWORTH
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Subdivisions in WINDERMERE
- ALADAR ON LAKE BUTLER
- ASHLIN PARK
- ASHLIN PARK PH 2
- BALMORAL
- BELLARIA
- BELMERE VILLAGE
- BELMERE VILLAGE G-5
- BELMERE VILLAGE G2 48 65
- BUTLER BAY
- BUTLER BAY,WINDERMERE CLUB
- BUTLER RIDGE
- CARRINGTON
- CARRINGTON 80/53 TRACT B
- CASA DEL LAGO
- CASA DEL LAGO REP
- CASA DEL LAGO-REPLAT
- CASABELLA
- CASABELLA PH 2
- CHAINE DU LAC
- DAVIS SHORES
- DOWN ACRES ESTATES
- DOWN POINT SUB
- EDEN ISLE
- EDEN ISLE BOAT RAMP
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE/BERKSHIRE PARK B G H I
- ESTANCIA/WINDERMERE
- ESTATES AT LAKE CLARICE
- ESTATES AT WINDERMERE
- FARMS
- GARDENS/ISLEWORTH UN #2
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- ISLES WINDERMERE
- ISLEWORTH
- ISLEWORTH WEST
- KEENE’S POINTE
- KEENES POINT
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 03 46/104
- LAKE BURDEN SOUTH PH 2
- LAKE BURDEN SOUTH PH I
- LAKE BUTLER ESTATES
- LAKE BUYNAK ESTATES
- LAKE CAWOOD COVE
- LAKE CAWOOD ESTATES
- LAKE CAWOOD ESTS REP
- LAKE CRESCENT RESERVE
- LAKE CYPRESS COVE PH 03
- LAKE DAVIS RESERVE A & B
- LAKE DOWN COVE
- LAKE DOWN ESTATES
- LAKE DOWN POINTE 50 42
- LAKE DOWN SHORES
- LAKE DOWN SHORES REP
- LAKE HANCOCK SHORES
- LAKE OLIVIA RESERVE
- LAKE SAWYER
- LAKE SAWYER SOUTH
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 05
- LAKE SAWYER SOUTH PH 1
- LAKE SAWYER SOUTH PH 2
- LAKE SAWYER SOUTH PH 3
- LAKE SAWYER SOUTH PH 5
- LAKES OF WINDERMERE LAKE REAMS TOWNHOMES PHASE 3
- LAKES OF WINDERMERE PEACHTREE
- LAKES OF WINDERMERE PH 2A
- LAKES WINDERMERE PH 01 49 108
- LAKES/WINDERMERE LAKE REAMS TWNH
- LAKES/WINDERMERE PH 02A
- LAKES/WINDERMERE PH 03 P & Q
- LAKES/WINDERMERE-LK REAMS TWHM
- LAKES/WINDERMERE-LK REAMS TWNH
- LAKES/WINDERMERE-PEACHTREE
- LAKESIDE AT LAKES OF WINDERMERE
- LAKESIDE AT LAKES OF WINDERMERE CONDOMINIUM
- LAKESIDE VILLAS
- LAKESIDE/LKS
- LAKESIDE/LKS/WINDERMERE
- LEGADO
- LEGADO 95/47 LOT 100
- LEGADO 95/47 LOT 99
- MANORS AT BUTLER BAY PH 01
- MANORS AT BUTLER BAY PH 02
- MARINA BAY ESTATES
- MARSH SUB
- MERRICK LNDG
- METCALF PARK REP
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE PH
- OASIS COVE/LAKESIDE VILLAGE PH VII
- OXFORD MOOR 47/30
- PALMS AT WINDERMERE
- PALMS/WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE PH 01 50 03
- PROVIDENCE PH 02
- RESERVE AT BELMERE
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT WINDERMERE
- ROBERTS LANDING
- ROYAL ESTATES
- SADDLECREST AT WINDERMERE
- SANCTUARY AT LAKES OF WINDERMERE
- SANDY SHORES
- SILVER WOODS
- SILVER WOODS PH 01
- SILVER WOODS PH 02
- SILVER WOODS PH 03
- SILVER WOODS PH 04
- SILVER WOODS PH 05
- SOUTHBRIDGE VILLAGE
- STILLWATER XINGS PRCL SC-13 PH
- SUMMERPORT
- SUMMERPORT EDENS HAMMOCK
- SUMMERPORT PH 03
- SUMMERPORT PH 04 C E F & G
- SUMMERPORT PH 05
- SUMMERPORT PH 2
- SUMMERPORT PH 5
- SUMMERPORT PHASE 1
- SUMMERPORT PHASE4
- SUMMERPORT TRAIL PH 2
- SUMMERPORT TRL
- SUNSET BAY
- TENNYSON PK/SUMMERPORT
- VINEYARDS OF HORIZONS WEST PHASE 1B
- VINEYARDS/HORIZONS WEST PH 2B
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE PH 02 REP
- WATERFORD POINTE PH 1 RESERVE
- WATERSTONE
- WATERSTONE A D E F G H J L
- WAUSEON RIDGE
- WEATHERSTONE ON LAKE OLIVIA
- WEST POINT COMMONS
- WESTOVER CLUB PH 01 44/139
- WESTSIDE VILLAGE
- WHICKHAM PARK
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WILLOWS AT LAKE RHEA
- WILLOWS AT LAKE RHEA PH 01
- WILLOWS AT LAKE RHEA PH 03
- WINDERMERE
- WINDERMERE DOWNS
- WINDERMERE ISLE
- WINDERMERE ISLE PH 2
- WINDERMERE ISLE-PH 2
- WINDERMERE LNDGS FD-1
- WINDERMERE LNDGS PH 02
- WINDERMERE SOUND
- WINDERMERE SOUND PH 2
- WINDERMERE TERRACE
- WINDERMERE TOWN
- WINDERMERE TOWN REP
- WINDERMERE TRAILS
- WINDERMERE TRAILS PARCEL 3 83/125 LOT 58
- WINDERMERE TRAILS PHASE 1C
- WINDERMERE TRLS
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3A
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH 4B
- WINDERMERE TRLS PH 5A
- WINDERMERE TRLS PH 5B
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
- WINDSTONE
Market Summary
Current real estate data for Single Family in WINDERMERE as of Oct 23, 2026
232
Single Family Listed
123
Avg DOM
495
Avg $ / SqFt
$2,636,546
Avg List Price
Property Summary
- Located in the ISLEWORTH subdivision, 5050 ISLEWORTH COUNTRY CLUB DRIVE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $3,189,000 and features 4 beds, 5 baths, and has approximately 3,365 square feet of living space, and was originally constructed in 1987. The current price per square foot is $948. The average price per square foot for Single Family listings in WINDERMERE is $495. The average listing price for Single Family in WINDERMERE is $2,636,546. To schedule a showing of MLS#o6438618 at 5050 ISLEWORTH COUNTRY CLUB DRIVE in WINDERMERE, FL, contact your WINDERMERE INTERNATIONAL REALTY agent at 4079901329.
Similar Listings Nearby
Courtesy of COMPASS FLORIDA LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than WINDERMERE INTERNATIONAL REALTY include the name of the listing broker. Neither the listing company nor WINDERMERE INTERNATIONAL REALTY shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 5050 ISLEWORTH COUNTRY CLUB DRIVE
WINDERMERE, FL
