PerformAction
(407) 203-9595
Sign In / Sign Up
 logo  logo
  • What’s My Home Worth
  • Property Search
  • Communities
  • Agents
  • Join Us
  • FRANCHISE WITH US
    • What’s My Home Worth
    • Property Search
    • Communities
    • Agents
    • Join Us
    • FRANCHISE WITH US
Sign In / Sign Up
(407) 203-9595
  • What’s My Home Worth
  • Property Search
  • Communities
  • Agents
  • Join Us
  • FRANCHISE WITH US
    • What’s My Home Worth
    • Property Search
    • Communities
    • Agents
    • Join Us
    • FRANCHISE WITH US
  • Property Info
  • Photo Slideshow
  • Photos
  • Print
  • Save Listing
  • Share Listing
  • Property Info
  • Photos
  • Photo Slideshow
  • Print

5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786

 (Sold on )

$8,500,000

  • Open House
  • New Listing
  • Price Reduced
  • Active
-1 More Schedule
Source MLS Verified
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
1/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
2/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
3/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
4/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
5/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
6/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
7/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
8/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
9/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
10/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
11/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
12/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
13/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
14/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
15/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
16/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
17/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
18/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
19/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
20/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
21/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
22/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
23/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
24/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
25/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
26/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
27/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
28/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
29/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
30/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
31/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
32/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
33/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
34/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
35/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
36/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
37/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
38/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
39/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
40/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
41/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
42/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
43/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
44/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
45/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
46/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
47/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
48/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
49/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
50/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
51/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
52/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
53/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
54/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
55/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
56/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
57/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
58/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
59/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
60/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
61/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
62/63
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
63/63
  • 4 BedroomBeds
  • 5 BathroomBaths
  • 7,100Sqft
  • 0Acres
  • Single FamilyType
  • O6446272MLS#
-1 More Schedule

Property Description

Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworths 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.

Property Videos And Tours

  • Virtual Tour

Additional Virtual Tour

  • Virtual Tour

Thank you for requesting a showing of this property. A representative will be in touch with you shortly to confirm the requested showing date and time.
Please note that your appointment is not confirmed until someone contacts you.

Request Info/ Schedule Showing

Submit

Property Details 5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786

Facts & Features

  • MLS #: O6446272
  • Status: Active
  • Date Listed: 10/01/2026
  • Type: Single Family
  • Sub Type: Single Family Residence
  • Year Built: 1995
  • Style: Mediterranean
  • Price: $8,500,000
  • Acres: 0.93
  • Area: 34786 - Windermere
  • County: Orange
  • Subdivision: ISLEWORTH
  • Bedrooms: 4
  • Bathrooms: 5
  • Full Baths: 5
  • Total SqFt: 7,100

Amenities

  • Amenities: Cable TV, Gated, Maintenance, Optional Additional Fees, Playground, Security
  • Parking: Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
  • # of Garages: 4
  • Features: Association Recreation - Owned, Community Mailbox, Fitness Center, Golf Carts OK, Golf, Playground, Pool, Tennis Court(s), Street Lights
  • Waterfront: Yes
  • Waterfront Type: Public
  • Pool: Yes
  • Pool Type: In Ground, Lighting

Interior

  • Interior Features: Built-in Features, Cathedral Ceiling(s), Ceiling Fans(s), Central Vaccum, Crown Molding, Eat-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, Carpet, Marble, Travertine, Wood
  • 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
  • Utilities: Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Underground Utilities
  • Heating: Central, Zoned
  • Cooling: Central Air, Zoned

Exterior

  • Exterior Features: Balcony, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters
  • Lot Description: Landscaped, On Golf Course, Oversized Lot, Paved, Private
  • Roof: Tile
  • Construction: Block, Stucco

Schools

  • Elementary: Windermere Elem
  • Middle: Chain of Lakes Middle
  • High: Olympia High

Additional Information

  • Zoning: P-D

Output format
 

Estimated Monthly Mortgage Calculator

This calculator is provided for informational purposes only by Burrow Services, Inc. You should not make any decisions based simply on the information provided. Values indicated are estimates and may not be accurate and are only to be used as a guide. This calculator should not be relied upon in any way as the sole source of information. Please consult your financial, tax or legal advisers for an accurate assessment of your mortgage payments and any advice relating to your personal circumstances.

Similar Listings

    • New Listing
    • Price Reduced$500,000
    • Open House
    • Sold
    • Leased
    • Pending
    • Coming Soon
    • Rental
    4226 DOWNEAST LANE
    WINDERMERE FL 34786
    $9,250,000
    5 Bed 5 Beds 3 Bath 3 Baths Sq.ft. 5,316
    MLS# O6355233 Single Family
    Listing Courtesy of: COLDWELL BANKER RESIDENTIAL RE | 407-647-1211
    Listing By:COLDWELL BANKER RESIDENTIAL RE
    Request Info
    Delete
      • New Listing
      • Price Reduced
      • Open House
      • Sold
      • Leased
      • Pending
      • Coming Soon
      • Rental
      724 W 2ND AVENUE
      WINDERMERE FL 34786
      $7,500,000
      6 Bed 6 Beds 8 Bath 8 Baths Sq.ft. 6,874
      MLS# O6426995 Single Family
      Listing Courtesy of: THE SIMON SIMAAN GROUP | 407-558-1396
      Listing By:THE SIMON SIMAAN GROUP
      Request Info
      Delete
        • New Listing
        • Price Reduced
        • Open House
        • Sold
        • Leased
        • Pending
        • Coming Soon
        • Rental
        9343 TIBET POINTE CIRCLE
        WINDERMERE FL 34786
        $7,450,000
        7 Bed 7 Beds 10 Bath 10 Baths Sq.ft. 8,362
        MLS# O6443379 Single Family
        Listing Courtesy of: NOVA REAL ESTATE SERVICES INC | 407-592-1744
        Listing By:NOVA REAL ESTATE SERVICES INC
        Request Info
        Delete
          • New Listing
          • Price Reduced$345,000
          • Open House
          • Sold
          • Leased
          • Pending
          • Coming Soon
          • Rental
          5074 ISLEWORTH COUNTRY CLUB DRIVE
          WINDERMERE FL 34786
          $7,250,000
          5 Bed 5 Beds 7 Bath 7 Baths Sq.ft. 7,099
          MLS# O6373191 Single Family
          Listing Courtesy of: MEM REALTY GROUP | 407-/58-3702
          Listing By:MEM REALTY GROUP
          Request Info
          Delete
            • New Listing
            • Price Reduced
            • Open House
            • Sold
            • Leased
            • Pending
            • Coming Soon
            • Rental
            5373 ISLEWORTH COUNTRY CLUB DRIVE
            WINDERMERE FL 34786
            $7,200,000
            5 Bed 5 Beds 6 Bath 6 Baths Sq.ft. 5,993
            MLS# O6439156 Single Family
            Listing Courtesy of: STOCKWORTH REALTY GROUP | 407-909-5900
            Listing By:STOCKWORTH REALTY GROUP
            Request Info
            Delete
              • New Listing
              • Price Reduced$405,000
              • Open House
              • Sold
              • Leased
              • Pending
              • Coming Soon
              • Rental
              9349 TIBET POINTE CIRCLE
              WINDERMERE FL 34786
              $6,995,000
              5 Bed 5 Beds 8 Bath 8 Baths Sq.ft. 7,529
              MLS# O6404415 Single Family
              Listing Courtesy of: CORCORAN PREMIER REALTY | 407-965-1155
              Listing By:CORCORAN PREMIER REALTY
              Request Info
              Delete
                • New Listing
                • Price Reduced
                • Open House
                • Sold
                • Leased
                • Pending
                • Coming Soon
                • Rental
                6113 GROSVENOR SHORE DRIVE
                WINDERMERE FL 34786
                $6,950,000
                7 Bed 7 Beds 8 Bath 8 Baths Sq.ft. 8,722
                MLS# O6443311 Single Family
                Listing Courtesy of: COLDWELL BANKER REALTY | 407-647-1211
                Listing By:COLDWELL BANKER REALTY
                Request Info
                Delete
                  • New Listing
                  • Price Reduced$50,000
                  • Open House
                  • Sold
                  • Leased
                  • Pending
                  • Coming Soon
                  • Rental
                  6055 LOUISE COVE DRIVE
                  WINDERMERE FL 34786
                  $6,850,000
                  5 Bed 5 Beds 6 Bath 6 Baths Sq.ft. 7,158
                  MLS# O6430931 Single Family
                  Listing Courtesy of: STOCKWORTH REALTY GROUP | 407-909-5900
                  Listing By:STOCKWORTH REALTY GROUP
                  Request Info
                  Delete
                    • New Listing
                    • Price Reduced$100,000
                    • Open House
                    • Sold
                    • Leased
                    • Pending
                    • Coming Soon
                    • Rental
                    9061 RON DEN LANE
                    WINDERMERE FL 34786
                    $6,800,000
                    5 Bed 5 Beds 7 Bath 7 Baths Sq.ft. 6,300
                    MLS# O6417446 Single Family
                    Listing Courtesy of: CORCORAN PREMIER REALTY | 407-965-1155
                    Listing By:CORCORAN PREMIER REALTY
                    Request Info
                    Delete
                      • New Listing
                      • Price Reduced$249,999
                      • Open House
                      • Sold
                      • Leased
                      • Pending
                      • Coming Soon
                      • Rental
                      9621 WINDY RIDGE ROAD
                      WINDERMERE FL 34786
                      $6,750,000
                      9 Bed 9 Beds 16 Bath 16 Baths Sq.ft. 20,445
                      MLS# O6451612 Single Family
                      Listing Courtesy of: CITARELLI REALTY GROUP LLC | 321-303-4238
                      Listing By:CITARELLI REALTY GROUP LLC
                      Request Info
                      Delete
                        • New Listing
                        • Price Reduced
                        • Open House
                        • Sold
                        • Leased
                        • Pending
                        • Coming Soon
                        • Rental
                        11103 BRIDGE HOUSE ROAD
                        WINDERMERE FL 34786
                        $6,750,000
                        5 Bed 5 Beds 8 Bath 8 Baths Sq.ft. 9,403
                        MLS# O6453159 Single Family
                        Listing Courtesy of: STOCKWORTH REALTY GROUP | 407-909-5900
                        Listing By:STOCKWORTH REALTY GROUP
                        Request Info
                        Delete
                          • New Listing
                          • Price Reduced
                          • Open House
                          • Sold
                          • Leased
                          • Pending
                          • Coming Soon
                          • Rental
                          8342 BOYLA COURT
                          WINDERMERE FL 34786
                          $6,700,000
                          8 Bed 8 Beds 10 Bath 10 Baths Sq.ft. 8,133
                          MLS# O6422852 Single Family
                          Listing Courtesy of: THE SIMON SIMAAN GROUP | 407-558-1396
                          Listing By:THE SIMON SIMAAN GROUP
                          Request Info
                          Delete
                           Ironvalley Realtors Logo

                          WE GOTyourBACK.

                          OFFICES

                          • Orlando Office

                          • 7680 Universal Blvd, Suite 300 Orlando FL 32819 Contact: (407) 203-9595

                          SEARCH

                          Residential Commercial Lot & Land Multi-Family
                          ©2026 IVRE Orlando.
                          Contact Blog Privacy Policy Accessibility Fair Housing DMCA Notice Agent Login
                          Iron Valley Real Estate, LLC is a real estate franchise company. Each Iron Valley Real Estate office is Independently Owned and Operated. Iron Valley Real Estate, LLC is an Equal Opportunity Employer and supports the Fair Housing Act.
                          Iron Valley Real Estate is powered by Burrow Services, Inc.
                          • Comparison List   0