Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world. Designed by architect Terry Irwin and built by Ballard Construction, with interior designs by Faith Fournet, the property has been fully transformed and thoughtfully curated over the last three years to deliver exceptional comfort, sophistication and panache at every turn. The two-story estate is set on a pristine 1.02-acre golf-front home site along Isleworth’s famed championship golf course and from the moment you enter, you’ll be captivated by the artistry in design and modern innovation. The interiors span more than 9,500 square feet living and 13,000 under roof, blending 5 bedrooms, 5.5 baths and an array of indoor and outdoor living areas with uncompromisingly luxurious finishes designed for effortless entertaining and quiet moments alike. At the heart of the home, the showstopping glass-enclosed wine room—temperature-controlled and with more than 2,200-bottle capacity—is a collector’s dream and the ultimate conversation piece. The primary suite is a sanctuary unto itself, featuring a magnificent two-story closet and dedicated dressing room with a bar. Indulge in true tranquility within the home’s private wellness suite, complete with exercise room, a rejuvenating steam room, dry sauna and invigorating cold plunge tub. Additional interior highlights include the grand kitchen with Cristallo quartzite lighted countertops; a fully custom lounge with full bar; an upper-level game room with bar; an oversized, air-conditioned garage accommodating up to 8 vehicles; two laundry rooms; and more. Outdoor spaces are equally impressive, with an expansive lanai and balcony, a custom swimming pool with fire pits, meticulously landscaped yard adorned with integrated lighting, sound and lush, native greenery and putting green —all overlooking panoramic views of Isleworth’s championship golf course. Whether hosting guests or enjoying a peaceful evening at home, this estate offers a rare opportunity to live a life of unmatched beauty, comfort, and distinction in one of Central Florida’s most desirable enclaves.
Property Details
Price:
$14,250,000
MLS #:
O6304800
Status:
Pending
Beds:
5
Baths:
5.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLEWORTH
Neighborhood:
34786windermere
Listed Date:
May 19, 2025
Finished Sq Ft:
9,511
Total Sq Ft:
12,319
Lot Size:
44,529 sqft / 1.02 acres (approx)
Year Built:
1999
See this Listing
Schools
Elementary School:
Windermere Elem
Middle School:
Chain of Lakes Middle
High School:
Olympia High
Interior
Appliances
Bar Fridge, Built-In Oven, Dishwasher, Disposal, Freezer, Ice Maker, Microwave, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Bathrooms
5 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Marble, Tile, Hardwood
Heating
Central, Electric
Interior Features
Built-in Features, Ceiling Fan(s), High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Sauna, Smart Home, Stone Counters, Walk-In Closet(s), Wet Bar
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Architectural Style
Custom
Attached Garage YN
1
Community Features
Lake, Private Boat Ramp, Gated Community – Guard, Golf Carts OK, Playground
Construction Materials
Block, Concrete
Covered Spaces
6
Direction Faces
Northeast
Exterior Features
Balcony, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Rain Gutters
Fencing
Fenced
Garage Spaces
6
Lot Features
Cul-De-Sac, Landscaped, On Golf Course
Other Structures
Outdoor Kitchen
Parking Features
Electric Vehicle Charging Station(s), Garage Door Opener, Oversized
Patio And Porch Features
Porch, Screened
Roof
Tile
Security Features
Gated Community, Security Gate, Security System
Spa Features
Heated, In Ground
View
Golf Course
Waterfront Features
Lake
Financial
HOA Fee
$3,672
HOA Fee Frequency
Quarterly
HOA Includes
24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Private Road, Security
HOA Name
Dan O’Connell
Tax Year
2024
Taxes
$37,372
Map
Community
- Address5525 ISLEWORTH COUNTRY CLUB DR WINDERMERE FL
- SubdivisionISLEWORTH
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Subdivisions in WINDERMERE
- ACREAGE
- ALADAR ON LAKE BUTLER
- ASHLIN FARK PH 2
- ASHLIN PARK PH 1
- ASHLIN PARK PH 2
- BELLARIA
- BELMERE VILLAGE G2 48 65
- BELMERE VILLAGE G5
- BUTLER BAY
- CARRINGTON
- CASA DEL LAGO REP
- CASABELLA
- CASABELLA PH 2
- CHAINE DE LAC
- CHAINE DU LAC
- CREEKS RUN
- DAVIS SHORES
- DIAMONDHEAD
- DOWN POINT SUB
- EDEN’S HAMMOCK
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE AT BERKSHIRE PARK
- ENCLAVE/BERKSHIRE PARK B G H I
- ESTANCIA/WINDERMERE
- ESTATES AT WINDERMERE
- FARMS
- GARDENS OF ISLEWORTH
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- HARBOR ISLE
- ISLEWORTH
- ISLEWORTH WEST
- KEENE’S POINTE
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 1
- KEENES POINTE UNIT 9
- KEENES POINTE UT 06 50 95
- KELSO ON LAKE BUTLER
- LAKE BURDEN SOUTH PH 2
- LAKE BURDEN SOUTH PH 2 #35 36
- LAKE BURDEN SOUTH PH I
- LAKE BUTLER ESTATES
- LAKE BUTLER PARK PT REP
- LAKE BUYNAK ESTATES
- LAKE CAWOOD ESTATES
- LAKE CRESCENT RESERVE
- LAKE DOWN ESTATES
- LAKE DOWN RESERVE
- LAKE DOWN SHORES REP
- LAKE REAMS TOWNHOMES
- LAKE ROPER POINTE
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 02
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 05
- LAKE SAWYER SOUTH PH 1
- LAKE SAWYER SOUTH PH 3
- LAKES
- LAKES OF WINDERMERE PH 2A
- LAKES WINDERMERE PH 01 49 108
- LAKES/WINDERMERE LAKE REAMS
- LAKES/WINDERMERE LAKE REAMS TWNH
- LAKES/WINDERMERE PH 02A
- LAKES/WINDERMERE PH 03 P & Q
- LAKES/WINDERMERE PH 04
- LAKES/WINDERMERE-LK REAMS TWHM
- LAKES/WINDERMERE-LK REAMS TWNH
- LAKES/WINDERMERE-PEACHTREE
- LAKESIDE AT LAKES OF WINDERMERE CONDO PH 3
- LAKESIDE VILLAS
- LAKESIDE/LKS/WINDERMERE
- LAKESIDE/LKS/WINDERMERE A CONDO
- LAKESIDE/LKS/WINDERMERE PH 3
- LEGADO
- MARINA BAY ESTATES
- MERRICK LNDG
- METCALF PARK REP
- OASIS COVE 2 AT LAKESIDE VILAGE
- OASIS COVE AT LAKE SIDE
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE PH
- PALMS AT WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE
- PROVIDENCE PH 01 50 03
- PROVIDENCE PH 02
- RESERVE AT BELMERE
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT BELMERE PH 03 51 01
- RESERVE AT BELMERE PHASE IV
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT LAKE BUTLER SOUND UNIT 2
- RESERVE AT WINDERMERE
- ROBERTS LANDING
- ROYAL ESTATE
- ROYAL ESTATES
- SADDLECREST AT WINDERMERE
- SANCTUARY/LKS/WINDERMERE
- SAWYER SHORES SUB
- SAWYER SOUND
- SILVER WOODS PH 02
- SILVER WOODS PH 03
- SILVER WOODS PH 04
- STILLWATER XINGS PRCL SC-13 #2
- SUMMERPORT
- SUMMERPORT BEACH
- SUMMERPORT PH 03
- SUMMERPORT PH 05
- TILDENS GROVE
- TILDENS GROVE PH 01 47/65
- TUSCANY RIDGE 50 141
- VINEYARDS/HORIZONS WEST PH 1A
- VINEYARDS/HORIZONS WEST PH 1B
- VINEYARDS/HORIZONS WEST PH 2A
- VINEYARDS/HORIZONS WEST PH 2B
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE
- 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
- WESTOVER RESERVE PH 02
- WESTSIDE VILLAGE
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WILLOWS AT LAKE RHEA PH 02
- WILLOWS AT LAKE RHEA PH 03
- WINDEMERE SOUND PH 2
- WINDEMERE TRLS PH 3B
- WINDERMERE
- WINDERMERE DOWNS
- WINDERMERE DOWNS PH 03
- WINDERMERE ISLE
- WINDERMERE ISLE-PH 2
- WINDERMERE LANDINGS
- WINDERMERE LANDINGS PH 2
- WINDERMERE LNDGS FD-1
- WINDERMERE LNDGS PH 02
- WINDERMERE POINTE
- WINDERMERE REP
- WINDERMERE RESERVE
- WINDERMERE SOUND
- WINDERMERE SOUND PH 2
- WINDERMERE TERRACE
- WINDERMERE TOWN
- WINDERMERE TOWN REP
- WINDERMERE TRAILS
- WINDERMERE TRAILS PHASE 5A 80/102 LOT 39
- WINDERMERE TRLS PH 1A
- WINDERMERE TRLS PH 1B
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3A
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH 4B
- WINDERMERE TRLS PH 5A
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
- WINDSTONE
Market Summary
Current real estate data for Single Family in WINDERMERE as of Apr 23, 2026
289
Single Family Listed
96
Avg DOM
458
Avg $ / SqFt
$2,232,330
Avg List Price
Property Summary
- Located in the ISLEWORTH subdivision, 5525 ISLEWORTH COUNTRY CLUB DR WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $14,250,000 and features 5 beds, 6 baths, and has approximately 9,511 square feet of living space, and was originally constructed in 1999. The current price per square foot is $1,498. The average price per square foot for Single Family listings in WINDERMERE is $458. The average listing price for Single Family in WINDERMERE is $2,232,330. To schedule a showing of MLS#o6304800 at 5525 ISLEWORTH COUNTRY CLUB DR in WINDERMERE, FL, contact your Preferred Real Estate Brokers agent at 4076987254.
Similar Listings Nearby
Courtesy of ISLEWORTH REALTY 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 Preferred Real Estate Brokers include the name of the listing broker. Neither the listing company nor Preferred Real Estate Brokers 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. 5525 ISLEWORTH COUNTRY CLUB DR
WINDERMERE, FL





