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For sale
    • $5,300,000

    5199 Latrobe Dr, Windermere, FL 34786

    6beds
    4,665sqft
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    Single Family Residence
    Built in 1993
    0.52 Acres Lot
    $4,872,000 Zestimate®
    $1,136/sqft
    $1,224/mo HOA

    What's special

    Panoramic golf course vistasContemporary finishesGolf-front estateQuartz countertopsCentrally located gourmet kitchenFenced rear lawnOversized custom walk-in closet
    Set within the gates of renowned Isleworth, this beautifully reimagined golf-front estate presents an exceptional opportunity to experience refined Central Florida living at its finest. Perfectly positioned along Isleworth’s celebrated championship golf course, the residence captures sweeping views of the fourth fairway while offering the privacy, comfort, and sophistication synonymous with the community’s distinguished lifestyle.Thoughtfully renovated and impeccably maintained, the home encompasses more than 6,600 square feet of combined indoor living and covered outdoor space, where contemporary finishes, designer lighting, and warm architectural details create an atmosphere that is both elegant and inviting. Every space has been intentionally curated—from the centrally located gourmet kitchen to the well-appointed utility spaces, resulting in a residence designed for effortless everyday living and elevated entertaining alike.The flexible floor plan offers exceptional versatility to suit a variety of lifestyles, accommodating configurations of up to six bedrooms, or alternatively a combination of bedrooms, office space, fitness room, or additional gathering areas. Six full baths and one half bath are finished with timeless materials and meticulous attention to detail throughout.At the heart of the home, the designer kitchen features sleek white cabinetry, quartz countertops, stainless steel appliances, and seamless connectivity to the expansive family room and casual dining area. Large glass openings invite natural light indoors while providing direct access to the screened lanai and resort-style pool environment beyond.The private primary suite serves as a luxurious retreat, highlighted by porcelain plank flooring, a spa-inspired bath with freestanding soaking tub and walk-in shower, and an oversized custom walk-in closet. Additional guest suites provide comfort and flexibility for family and visitors, while the home’s four-car garage and expansive motor court offer abundant space for automobile enthusiasts and guests alike.Outdoors, the estate transforms into a true private sanctuary. A newly redesigned saltwater pool and spa are enclosed within a custom lanai structure and complemented by an expansive new pool deck, creating a year-round setting for relaxation and entertaining. Lush landscaping, a fenced rear lawn, and panoramic golf course vistas further enhance the sense of serenity and exclusivity.Blending timeless elegance with modern livability, this exceptional Isleworth residence offers a rare combination of spacious design, privacy, and premier golf-front surroundings within one of the finest golf club communities in the world.
    52 days
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    630
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    33
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    Zillow last checked:

    Listing updated:

    Listed by:

    Monica Lochmandy 407-230-6888,

    ISLEWORTH REALTY LLC 407-909-9000,

    Michelle Corbin 407-491-2690,

    ISLEWORTH REALTY LLC

    Source: Stellar MLS,MLS#: O6409961MLS LogoOriginating MLS: Orlando Regional

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 6
      • Bathrooms: 7
      • Full bathrooms: 6
      • 1/2 bathrooms: 1
      Primary bedroom
      • Description: Room1
      • Features: Walk-In Closet(s)
      • Level: First
      Bedroom 1
      • Description: Room2
      • Features: Built-in Closet
      • Level: First
      Bedroom 2
      • Description: Room3
      • Features: Built-in Closet
      • Level: First
      Bedroom 3
      • Description: Room4
      • Features: Built-in Closet
      • Level: First
      Bedroom 4
      • Description: Room5
      • Features: Built-in Closet
      • Level: First
      Bedroom 5
      • Description: Room6
      • Features: Built-in Closet
      • Level: First
      Dining room
      • Description: Room10
      • Level: First
      Family room
      • Description: Room7
      • Level: First
      Kitchen
      • Description: Room8
      • Level: First
      Living room
      • Description: Room9
      • Level: First
      Heating
      • Central, Electric, Zoned
      Cooling
      • Central Air, Zoned
      Appliances
      • Included: Oven, Dishwasher, Disposal, Exhaust Fan, Microwave, Refrigerator
      • Laundry: Electric Dryer Hookup, In Kitchen, Laundry Room, Washer Hookup
      Features
      • Primary Bedroom Main Floor, Stone Counters, Walk-In Closet(s)
      • Flooring: Ceramic Tile
      • Doors: French Doors
      • Has fireplace: Yes
      • Fireplace features: Living Room
      Interior area
      • Total structure area: 6,622
      • Total interior livable area: 4,665 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 4
      • Parking features: Driveway, Split Garage
      • Attached garage spaces: 4
      • Has uncovered spaces: Yes
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Deck
      • Exterior features: Irrigation System, Rain Gutters
      • Has private pool: Yes
      • Pool features: Deck, Gunite, Heated, In Ground, Lighting, Screen Enclosure
      • Spa features: Heated, In Ground
      • Has view: Yes
      • View description: Golf Course, Water
      • Water view: Water
      • Waterfront features: Lake Privileges
      Lot
      • Size: 0.52 Acres
      • Features: Landscaped, On Golf Course
      Details
      • Parcel number: 162328389903150
      • Zoning: P-D
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Traditional
      • Property subtype: Single Family Residence
      Materials
      • Block, Concrete, Stucco
      • Foundation: Slab
      • Roof: Concrete,Tile
      Condition
      • New construction: No
      • Year built: 1993

      Utilities & green energy

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

      Community & HOA

      Community
      • Features: Community Boat Ramp, Water Access, Buyer Approval Required, Community Mailbox, Gated Community - Guard, Golf Carts OK, Golf, Park
      • Security: Gated Community, Security Gate
      • Pet fee: $0 monthly
      • Subdivision: ISLEWORTH
      HOA
      • Has HOA: Yes
      • Amenities included: Cable TV, Fence Restrictions, Gated, Playground, Security, Vehicle Restrictions
      • Services included: 24-Hour Guard, Cable TV, Reserve Fund, Internet, Maintenance Grounds, Maintenance Repairs, Private Road, Security
      • HOA fee: $1,224 monthly
      • HOA name: Dan O’Connell
      • HOA phone: 407-909-2071
      Location
      • Region: Windermere

      Financial & listing details

      • Price per square foot: $1,136/sqft
      • Tax assessed value: $2,197,938
      • Annual tax amount: $37,240
      • Date on market: 5/27/2026
      • Cumulative days on market: 53 days
      • Listing terms: Cash,Conventional
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved, Asphalt

        Estimated market value

        $4,872,000

        $4.63M - $5.12M

        $6,681/mo

        Price history

        DateEventPrice
        5/27/2026Listed for sale$5,300,000-3.5%$1,136/sqft
        Source: Stellar MLS #O6409961 Report a problem
        12/31/2025Listing removed$5,494,000$1,178/sqft
        Source: Stellar MLS #O6315618 Report a problem
        6/5/2025Listed for sale$5,494,000+113.4%$1,178/sqft
        Source: Stellar MLS #O6315618 Report a problem
        8/5/2022Sold$2,575,000-2.8%$552/sqft
        Source: Public Record Report a problem
        6/9/2022Pending sale$2,650,000$568/sqft
        Source: Stellar MLS #O6030513 Report a problem
        6/2/2022Listed for sale$2,650,000+76.7%$568/sqft
        Source: Stellar MLS #O6030513 Report a problem
        2/20/2019Sold$1,500,000-11.5%$322/sqft
        Source: Public Record Report a problem
        10/4/2018Price change$1,695,000-4.5%$363/sqft
        Source: ISLEWORTH REALTY LLC #O5737878 Report a problem
        6/1/2018Price change$1,775,000-6.5%$380/sqft
        Source: IRWIN REALTY GROUP LLC #O5536793 Report a problem
        5/7/2018Price change$1,898,000-0.1%$407/sqft
        Source: IRWIN REALTY GROUP LLC #O5536793 Report a problem
        1/19/2018Price change$1,899,000-5%$407/sqft
        Source: IRWIN REALTY GROUP LLC #O5536793 Report a problem
        9/26/2017Listed for sale$1,999,000+0.2%$429/sqft
        Source: IRWIN REALTY GROUP LLC #O5536793 Report a problem
        2/15/2017Listing removed$1,995,000$428/sqft
        Source: ISLEWORTH REALTY LLC #O5386479 Report a problem
        1/11/2017Listed for sale$1,995,000$428/sqft
        Source: ISLEWORTH REALTY LLC #O5386479 Report a problem
        4/14/2016Listing removed$1,995,000$428/sqft
        Source: ISLEWORTH REALTY INC #O5386479 Report a problem
        8/17/2015Listed for sale$1,995,000+0.3%$428/sqft
        Source: ISLEWORTH REALTY INC #O5386479 Report a problem
        7/12/2014Listing removed$1,990,000$427/sqft
        Source: Isleworth Realty INC #O5175883 Report a problem
        4/1/2014Listed for sale$1,990,000-16.9%$427/sqft
        Source: Isleworth Realty INC #O5175883 Report a problem
        11/29/2011Listing removed$2,395,000$513/sqft
        Source: Irwin Realty Group LLC #o4978366 Report a problem
        11/9/2011Listed for sale$2,395,000-4%$513/sqft
        Source: Irwin Realty Group LLC #o4978366 Report a problem
        5/29/2011Listing removed$2,495,000$535/sqft
        Source: Irwin Realty Group LLC #o4978366 Report a problem
        2/11/2011Listed for sale$2,495,000$535/sqft
        Source: Irwin Realty Group LLC #o4978366 Report a problem
        12/1/2010Listing removed$2,495,000$535/sqft
        Source: Irwin Realty Group LLC #o4978366 Report a problem
        11/13/2010Price change$2,495,000-10.7%$535/sqft
        Source: Irwin Realty Group LLC #o4978366 Report a problem
        5/29/2010Listed for sale$2,795,000+7.5%$599/sqft
        Source: Irwin Realty Group LLC #o4978366 Report a problem
        8/21/2007Sold$2,600,000+52.9%$557/sqft
        Source: Public Record Report a problem
        10/5/2004Sold$1,700,000+100%$364/sqft
        Source: Public Record Report a problem
        2/9/2004Sold$850,000-24.1%$182/sqft
        Source: Public Record Report a problem
        8/3/2000Sold$1,120,000+49.3%$240/sqft
        Source: Public Record Report a problem
        10/3/1995Sold$750,000$161/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$36,356 +6.9%$2,197,938 +2.7%
        2023$34,012 +57.8%$2,139,526 +59.9%
        2022$21,550 +8.6%$1,338,192 +10%
        2021$19,842 -6.4%$1,216,538 -5.7%
        2020$21,191 -27.4%$1,290,192 -26.5%
        2019$29,194 -2.8%$1,755,519 -1.6%
        2018$30,036 $1,784,502 +1.7%
        2017$30,036 +0.6%$1,754,259 +2%
        2016$29,850 -0.1%$1,720,328 +5.8%
        2015$29,879 +8.7%$1,625,921 +7.2%
        2014$27,477 +7.1%$1,516,119 +6.7%
        2013$25,655 +0.9%$1,421,437 +1.7%
        2012$25,418 -8.3%$1,397,697 -8%
        2011$27,713 -3.7%$1,518,848 -6.2%
        2010$28,772 $1,618,802 -12.7%
        2009-- $1,853,239 -11.4%
        2008$35,524 +56%$2,090,525 +13.6%
        2007$22,771 -6.4%$1,839,854 +15.8%
        2006$24,324 -0.1%$1,588,586 +22.8%
        2005$24,344 +10.5%$1,293,916 +11.4%
        2004$22,036 +6.5%$1,161,409 +8.5%
        2003$20,693 +4.5%$1,070,447 +3.5%
        2002$19,803 +4.5%$1,033,973 +7.6%
        2001$18,948 $960,951
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 34786

        Getting around

        9 / 100
        Car-Dependent
        28 / 100
        Somewhat Bikeable

        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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