Greys Buitrago

5092 Isleworth Country Club Drive

WINDERMERE, FL
$ 8,500,000 Beds 4 Baths 5 Sq 7,100 Virtual Tour
Monthly Estimate* How much can I afford?

Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive and has been beautifully reimagined with an extensive transformation over the last two years. The result is a sophisticated, move-in-ready home where timeless architectural character blends seamlessly with thoroughly modern style. Originally built by Pellegrini Homes and expanded to 7,100 square feet, the residence retains its signature architectural details, including custom ceilings, travertine floors with intricate tile inlays, and carefully crafted shell stone columns. The grandeur of the formal living room is accentuated by its soaring 20-foot ceiling, magnificent chandelier, and stately stone fireplace. A former bonus room has been thoughtfully transformed into the home's impressive new chef's kitchen, featuring custom cabinetry, an Italian-made 48-inch ILVE range, a luxury appliance collection, and elegant finishes. The original kitchen has been reimagined as a sophisticated entertaining bar with custom cabinetry, a built-in espresso cabinet, wine storage, and dedicated space for morning coffee and smoothies. Both spaces connect effortlessly to the casual dining area and formal dining room, creating an exceptional flow for everyday living and entertaining. The family room offers an open, airy setting with a built-in media display and effortless connection to the lanai. The main-level owner's suite provides a private retreat with a cozy fireplace, dual closets, and a lavish bath featuring dual vanities, a walk-in shower, and a luxurious soaking tub framed by elegant stone columns. A new main-level bedroom with private en-suite bath and an enlarged loft suite add flexibility for family and guests. Throughout the residence, new flooring, custom cabinetry and built-ins, designer lighting including bespoke Italian Murano glass fixtures, custom drapery, automated shades, and beautifully appointed furnishings create a cohesive, elevated aesthetic. Custom London-made closet lighting adds another layer of thoughtful detail, while modernized infrastructure, integrated technology, whole-home Wi-Fi, security, and smart-home features provide a seamless foundation for today's lifestyle. Outside, the residence has been transformed into an exceptional setting for both relaxation and entertaining. The pool has been resurfaced, outdoor living areas expanded, and a new outdoor kitchen and grilling area added, while a completely redesigned landscape, lighting, fencing, and fountain features enhance the grounds. Upstairs, the bedroom suites and expansive balcony capture panoramic views of the golf course and sparkling waters of Lake Bessie. The European-style lanai, with its graceful balustrade, creates an inviting setting for al fresco gatherings and captivating sunsets. This exceptional estate offers a rare combination of timeless architectural character, comprehensive modern improvements, sophisticated design, and an enviable golf-front setting within Isleworth.

Active

  • Price
  • $ 8,500,000
  • City
  • WINDERMERE
  • Bedrooms
  • 4
  • Full Bathrooms
  • 5
  • County
  • Orange
  • Half Bathrooms
  • 0
  • Area
  • Windermere
  • Lot Size
  • 0.93 Acres
  • Zip
  • 34786
  • Sqr Footage
  • 7,100
  • Year Built
  • 1995
  • Taxes
  • $ 57070
  • Style
  • Mediterranean
  • MLS#
  • O6446272
Listed By: ISLEWORTH REALTY LLC with 407-909-9000. - 407-909-9000
Data Source: Stellar MLS

Features

General

Sewer Septic Tank
Heating Central,Zoned
Cooling Central Air,Zoned
Utilities Cable Connected,Electricity Connected,Fire Hydrant,Natural Gas Connected,Street Lights,Underground Utilities
Roof Tile
Appliances Bar Fridge,Built-In Oven,Convection Oven,Dishwasher,Disposal,Dryer,Electric Water Heater,Exhaust Fan,Freezer,Ice Maker,Microwave,Range,Range Hood,Refrigerator,Washer,Water Filtration System,Wine Refrigerator
Zoning P-D
HOA Fee 3672
Garage Spaces 4
Association Fee Includes 24-Hour Guard,Cable TV,Escrow Reserves Fund,Internet,Maintenance Grounds,Maintenance Repairs,Private Road,Security
Architectural Style Mediterranean
Pool Features In Ground,Lighting
Security Features Closed Circuit Camera(s),Gated Community,Security Gate,Security Lights,Security System,Smoke Detector(s)
Construction Materials Block,Stucco
Pets Allowed Breed Restrictions,Yes
Year Built 1995
View Garden,Golf Course,Trees/Woods,Water
Levels Two
Property Subtype Single Family Residence
Tax Year 2026
Ownership Fee Simple
Community Features Association Recreation - Owned,Community Mailbox,Fitness Center,Golf Carts OK,Golf,Playground,Pool,Tennis Court(s)
Assoc Fee Paid Per Quarterly
County Orange
New Construction false
Property Type Residential
Association Amenities Cable TV,Gated,Maintenance,Optional Additional Fees,Playground,Security
Attached Garage true
Subdivision Name ISLEWORTH
Facing Direction East
Garage Y/N true
Total Rooms 5
Full Baths 5
Status Active
Directions I-4 to Conroy Windermere Road west to Isleworth subdivision. Stay straight on Isleworth Country Club Drive. Estate will be on the Left or Right.
High School Olympia High
City WINDERMERE
Body of Water BUTLER CHAIN OF LAKES
Association Name Dan O’Connell
Senior Community Y/N false
MLS Area 34786 - Windermere
Lot Size Units Square Feet
Lot Size Square Feet 40620
Carport Y/N false
Listing Terms Cash,Conventional
Spa Features Heated,In Ground
Elementary School Windermere Elem
Land Lease Y/N false
Tax Annual Amount 57070.63
Middle/Junior High School Chain of Lakes Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://player.vimeo.com/video/1230185615?h=e9768a3a03&badge=0&autopause=0&player_id=0&app_id=58479
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 48
Legal Description N 73 DEG W 204.27 FT S 22 DEG W ALONG LOTS 47 & 48 FOR 146.32 FT TO POB
Water View Lake - Chain of Lakes
Minimum Lease 8-12 Months
Water Access Y/N false
Monthly HOA Amount 1224
Water View Y/N true
Flood Zone Code X
In Law Suite YN false
Flood Zone Code X Yes

Interior Features

Interior Amenities Built-in Features,Cathedral Ceiling(s),Ceiling Fan(s),Central Vacuum,Crown Molding,Eating Space In Kitchen,High Ceilings,Kitchen/Family Room Combo,Primary Bedroom Main Floor,Solid Wood Cabinets,Stone Counters,Vaulted Ceiling(s),Walk-In Closet(s),Wet Bar,Window Treatments
Flooring Brick/Stone,Carpet,Marble,Travertine,Hardwood
Furnished Y/N Negotiable
Fireplace Features Living Room,Master Bedroom
Air Conditioning Y/N true
Heating Y/N true
Window Features Drapes,Shutters,Window Treatments
Fireplace Y/N true
Laundry Features Laundry Room
Total Bedrooms 4
LivingAreaSource Owner
Total Baths 5

Exterior Features

Exterior Amenities Balcony,French Doors,Irrigation System,Lighting,Outdoor Grill,Outdoor Shower,Rain Gutters
Vegetation Mature Landscaping,Trees/Landscaped
Fencing Fenced
Parking Features Circular Driveway,Garage Door Opener,Garage Faces Side,Golf Cart Garage
Lot Features Landscaped,On Golf Course,Oversized Lot
Water Source Public
Lot Size Area 40620
Foundation Details Slab
Spa true
Building Area Total 10319
Lot Size Acres 0.93
Road Surface Type Paved
Private Pool true
Waterfront Y/N false
Covered Spaces 4
Road Frontage Type Street Paved,Private Road

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Sarasota, FL office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

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

Price History

10/1/2026 Listed $8,500,000

Property vs Zip Code Average in 34786

Price
AVG $2.53M
$8.5M
Taxes
AVG $18,744
$57,070
Year Built
AVG 2006
1995

In The Neighborhood

Areas That We Cover

5092 Isleworth Country Club Drive WINDERMERE, FL is a Single Family Home for sale at $8500000 with 7100 sqft and a lot size of 0.93 Acres Acre(s). 5092 Isleworth Country Club Drive WINDERMERE has 4 bedrooms, 5 baths and was built in 1995. The property's zip code is 34786 which is in WINDERMERE, FL

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site 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.

Greys Buitrago

Greys Buitrago

305-815-2103

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