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Sold for $5,250,000
    • $5,250,000

    5243 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786

    4beds
    6,424sqft
    Single Family Residence
    Built in 1992
    0.51 Acres Lot
    $4,680,600 Zestimate®
    $817/sqft
    $7,680 Estimated rent

    Home value

    $4,680,600

    $4.45M - $4.91M

    $7,680/mo

    Zestimate® history
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    What's special

    Welcome to one of the most exquisite golf front estates within the main gates of Isleworth. Just a short distance from the prestigious Isleworth Golf & Country Club you will find a distinctive masterpiece that has the most amazing views of the golf course and The Butler Chain of Lakes. It is unique and rare to find a home with no neighbors on three sides. It gives you this great sense of privacy that can only be appreciated from this extraordinary property. This custom residence underwent a spare no expense remodel by McNally Construction and design by Debby Dearth of McNally Design in 2023 using the highest quality materials combining the latest designs with timeless Mediterranean architecture. The foyer leads to a living room adorned with basket weaved marble and wood flooring, 20’ ceilings complimented by wood beams, stone gas fireplace, and absolutely stunning views. The well-appointed chef’s kitchen is fully equipped with a large center island, custom wood cabinetry, Italian dolomite counter tops, Sub Zero refrigerator, and a Wolf gas range with griddle. The cocktail bar is adjacent to the kitchen and includes Cristallo quartzite counters and a temperature-controlled wine cellar that can easily accommodate 700+ bottles of wine. The family room boasts soaring vaulted ceilings with reclaimed solid wood floors and windows that flood the room with natural light. The main level master suite is spacious with impressive ceiling accoutrements, chandelier, large two-story walk in closet, spa like bathroom including a breakfast bar with a Sub Zero refrigerator, dual vanities, garden tub, glass shower, and French doors leading you to your well manicured grounds. Secondary bedrooms are all en-suites & generously sized. Relax in delight from your own theater room equipped with a projector, screen, and surround sound. This palatial mansion is located on the 2nd and 9th tees of the Isleworth championship golf course with almost 300 feet of golf frontage giving this magnificent residence amazing views of Lake Chase with a total sense of privacy. Exterior living spaces features a large covered lanai, heated salt pool, full pool bath, summer kitchen with stainless steel grill, sink, beverage refrigerator, and custom built stacked stone outdoor fireplace that makes it the perfect for entertaining or just enjoying the cool lake breezes. Notable upgrades done in 2023 include a brand new tile roof, replacement of all custom doors and windows, remodeled kitchen, bathrooms with Kohler fixtures, door hardware, cocktail bar, flooring, Control 4 smart house features for lighting, electric shades, cameras, HVAC, pool equipment, garage doors, locks, built-in sound system, pool resurface, new pool heater, landscaping, complete interior and exterior paint, and exterior gray pavers. The timeless architecture with its stately well balanced curb appeal shows an unparalleled attention to details on quality and perfection throughout. Here is your once in a lifetime opportunity to own an exclusive residence combining both lake and golf lifestyles. Be sure to click on the virtual tour links. <iframe width='853' height='480' src=https://my.matterport.com/show/?m=pmh1hwNxnW3&mls=1 ></iframe>

    Zillow last checked:

    Listing updated:

    Listed by:

    Simon Simaan 407-558-1396,

    THE SIMON SIMAAN GROUP 407-558-1396

    Bought with:

    Rob Rahter, 3129153

    STOCKWORTH REALTY GROUP

    Source: Stellar MLS,MLS#: O6227542MLS LogoOriginating MLS: Orlando Regional

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 6
    • Full bathrooms: 5
    • 1/2 bathrooms: 1
    Rooms
    • Room types: Attic, Breakfast Room Separate, Den/Library/Office, Family Room, Great Room, Loft, Media Room, Storage Rooms
    Primary bedroom
    • Features: Walk-In Closet(s)
    • Level: First
    • Dimensions: 23x20
    Bedroom 3
    • Features: En Suite Bathroom, Walk-In Closet(s)
    • Level: Second
    • Dimensions: 19x13
    Bedroom 3
    • Features: En Suite Bathroom, Walk-In Closet(s)
    • Level: Second
    • Dimensions: 17x12
    Bedroom 4
    • Features: En Suite Bathroom, Walk-In Closet(s)
    • Level: Second
    • Dimensions: 16x12
    Den
    • Level: First
    • Dimensions: 17x13
    Dinette
    • Level: First
    • Dimensions: 14x11
    Dining room
    • Level: First
    • Dimensions: 18x12
    Family room
    • Level: First
    • Dimensions: 27x26
    Kitchen
    • Level: First
    • Dimensions: 18x17
    Living room
    • Level: First
    • Dimensions: 27x22
    Media room
    • Level: Second
    • Dimensions: 17x13
    Heating
    • Central, Electric, Zoned
    Cooling
    • Central Air, Zoned
    Appliances
    • Included: Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
    • Laundry: Inside
    Features
    • Built-in Features, Ceiling Fan(s), Central Vacuum, Coffered Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar
    • Flooring: Carpet, Marble, Porcelain Tile, Hardwood
    • Doors: French Doors, Outdoor Kitchen
    • Windows: Blinds, Insulated Windows, Shutters, Thermal Windows, Window Treatments
    • Has fireplace: Yes
    • Fireplace features: Gas, Living Room, Outside
    Interior area
    • Total structure area: 7,246
    • Total interior livable area: 6,424 sqft

    Property

    Parking
    • Total spaces: 3
    • Parking features: Circular Driveway, Garage Faces Side, Golf Cart Garage
    • Attached garage spaces: 3
    • Has uncovered spaces: Yes
    • Details: Garage Dimensions: 31x24
    Features
    • Levels: Two
    • Stories: 2
    • Patio & porch: Covered, Porch, Rear Porch
    • Exterior features: Irrigation System, Lighting, Outdoor Kitchen, Storage
    • Has private pool: Yes
    • Pool features: Heated, In Ground, Salt Water
    • Fencing: Fenced,Other
    • Has view: Yes
    • View description: Golf Course, Water, Lake
    • Has water view: Yes
    • Water view: Water,Lake
    • Waterfront features: Lake Privileges, Boat Ramp - Private
    • Body of water: LAKE CHASE
    Lot
    • Size: 0.51 Acres
    • Features: In County, Level, On Golf Course
    • Residential vegetation: Mature Landscaping, Oak Trees
    Details
    • Additional structures: Outdoor Kitchen
    • Parcel number: 162328389902310
    • Zoning: P-D
    • Special conditions: None

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Custom,Mediterranean
    • Property subtype: Single Family Residence
    Materials
    • Block, Stucco
    • Foundation: Slab
    • Roof: Tile
    Condition
    • New construction: No
    • Year built: 1992

    Utilities & green energy

    • Sewer: Septic Tank
    • Water: Public
    • Utilities for property: Cable Connected, Natural Gas Connected, Street Lights, Underground Utilities, Water Connected

    Community & HOA

    Community
    • Features: Community Boat Ramp, Private Boat Ramp, Water Access, Buyer Approval Required, Deed Restrictions, Gated Community - Guard, Golf Carts OK, Golf, Park
    • Security: Closed Circuit Camera(s), Gated Community, Security System, Security System Owned, Smoke Detector(s), Touchless Entry
    • Pet fee: $0 monthly
    • Subdivision: ISLEWORTH
    HOA
    • Has HOA: Yes
    • Amenities included: Gated, Park, Security
    • Services included: 24-Hour Guard, Manager, Private Road, Security
    • HOA fee: $923 monthly
    • HOA name: Dan O'Connell
    • HOA phone: 407-909-2071
    Location
    • Region: Windermere

    Financial & listing details

    • Price per square foot: $817/sqft
    • Tax assessed value: $3,041,526
    • Annual tax amount: $46,929
    • Date on market: 8/1/2024
    • Cumulative days on market: 9 days
    • Listing terms: Cash,Conventional
    • Ownership: Fee Simple
    • Total actual rent: 0
    • Road surface type: Paved, Asphalt

    Price history

    DateEventPrice
    7/9/2026Listing removed$5,100,000$794/sqft
    Source: Stellar MLS #O6348067 Report a problem
    3/11/2026Price change$5,100,000-4.2%$794/sqft
    Source: Stellar MLS #O6348067 Report a problem
    10/9/2025Listed for sale$5,325,000+1.4%$829/sqft
    Source: Stellar MLS #O6348067 Report a problem
    8/20/2024Sold$5,250,000$817/sqft
    Source: Stellar MLS #O6227542 Report a problem
    8/12/2024Pending sale$5,250,000$817/sqft
    Source: Stellar MLS #O6227542 Report a problem
    8/1/2024Price change$5,250,000+40%$817/sqft
    Source: Stellar MLS #O6227542 Report a problem
    2/10/2022Pending sale$3,750,000$584/sqft
    Source: Stellar MLS #O6002640 Report a problem
    2/10/2022Listed for sale$3,750,000-26.5%$584/sqft
    Source: Stellar MLS #O6002640 Report a problem
    1/30/2009Listing removed$5,100,000$794/sqft
    Source: NCI #O4862199 Report a problem
    8/4/2008Listed for sale$5,100,000+61.9%$794/sqft
    Source: NCI #O4862199 Report a problem
    12/28/2006Sold$3,150,000+24%$490/sqft
    Source: Public Record Report a problem
    8/3/2005Sold$2,540,000$395/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2024$50,194 +7%$3,041,526 +2.8%
    2023$46,929 +35.2%$2,959,096 +33.3%
    2022$34,699 +1.1%$2,219,138 +3%
    2021$34,310 +0.6%$2,154,503 +1.4%
    2020$34,100 +0.7%$2,124,756 +2.3%
    2019$33,851 +0.7%$2,076,985 +1.9%
    2018$33,622 $2,038,258 -6.6%
    2017$33,622 +1%$2,182,405 +2%
    2016$33,281 +0%$2,140,246 +4.6%
    2015$33,265 -2.6%$2,045,468 +5.7%
    2014$34,161 +2%$1,935,505 +2%
    2013$33,489 -3.2%$1,897,805 -2.4%
    2012$34,579 -8.9%$1,944,416 -8.4%
    2011$37,944 -13.8%$2,122,530 -15.9%
    2010$44,034 $2,523,378 -13.4%
    2009-- $2,915,124 +7.8%
    2008$45,201 -2.3%$2,703,101 -2%
    2007$46,248 +6.9%$2,758,888 +17%
    2006$43,255 +161.4%$2,357,567 +95.1%
    2005$16,547 +4.3%$1,208,373 +6%
    2004$15,869 +0.1%$1,139,930 -0.8%
    2003$15,851 +3.4%$1,149,083 +4.5%
    2002$15,324 -1.2%$1,099,450 +9.7%
    2001$15,514 +2.4%$1,002,531 +4.1%
    2000$15,153 $962,671
    Find assessor info on the county website

    Neighborhood: 34786

    Nearby homes

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Windermere Elem
    • Middle: Chain of Lakes Middle
    • High: Olympia High

    Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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    Estimated market value
    $4,680,600
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $4,680,600

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