5036 LATROBE DRIVE, Windermere, FL, 34786 | $4,900,000

Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5, 548 square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat. The upper level greets guests with custom French entry doors that flow into the open formal living and dining rooms, perfectly designed for gatherings. The kitchen is spacious and inviting, offering casual dining and seamless access to the main living areas. A richly appointed library adds warmth and refinement, while two en-suite bedrooms complete this floor, including the primary suite. With its oversized windows capturing endless lake vistas, a large sitting area, exterior balcony, and an en-suite bath featuring dual vanities, a soaking tub, and walk-in shower, the primary suite is a sanctuary of light and serenity. On the lower level, the estate offers two expansive bonus areas joined by a well-equipped kitchenette. Ideal for gaming, entertaining, or working from home, both spaces connect effortlessly to the sun-drenched pool terrace—seamlessly integrating indoor luxury and outdoor living. A stunning mature oak tree anchors the property's beautiful lakefront grounds, stretching gracefully toward the water’s edge—a signature of the property’s natural beauty. Beyond the oak tree, Lake Bessie shimmers in full view, offering a breathtaking backdrop to the estate. A rare combination of elegance, versatility, and iconic setting, this residence presents a lifestyle within one of Central Florida's finest communities.

Features

  • Amenities: Cable TV, Playground
  • Rooms: 8
  • Bedrooms: 5
  • Baths: 4 full / 1 half
  • Laundry: Inside, Laundry Room
  • Style: Traditional
  • Year Built: 1990
  • Garage: 3-car
  • Heating: Central, Electric, Natural Gas
  • Cooling: Central Air, Zoned
  • Approx Sq. Feet: 5,548
  • Acreage: 0.69
  • Est. Taxes: $17,326
  • HOA Fee: $3,672 Quarterly
  • Lot Desc: Landscaped, Near Golf Course
  • View: Water
  • Elem. School: Windermere Elem
  • Middle School: Chain of Lakes Middle
  • High School: Olympia High
  • Pool: Deck, In Ground, Lighting
  • Pet Policy: Breed Restrictions
  • Appliances: Bar Fridge, Built-In Oven, Convection Oven, Dishwasher, Disposal, Dryer, Freezer, Gas Water Heater, Ice Maker, Microwave, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
  • MLS#: O6346003
  • Days on Market: 139 days
  • Website: https://www.raveis.com
    /eprop/O6346003/5036latrobedrive_windermere_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is 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. (last updated 3/3/2026 9:47:08 PM)

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Kate RockettRVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 1500191

617.281.4872

Kate.Rockett@raveis.com

Our Executive Mortgage Banker:

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Our Insurance Division:

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5036 LATROBE DRIVE, Windermere, FL, 34786

$4,900,000

The Diaz Elite Group

Sales Associates

William Raveis Real Estate

Phone: 781.828.4550

TheDiazEliteGroup@raveis.com

Kate Rockett

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 617.281.4872

Kate.Rockett@raveis.com

NMLS Mortgage Loan Originator ID 1500191

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $3,920,000 $3,920,000 $3,920,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.375% 5.875% 5.625%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.117% 5.972% 5.826%
Monthly Tax Payment $1,444 $1,444 $1,444
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $21,951 $23,188 $32,290
Total Monthly Payment $23,520 $24,757 $33,859

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.  The Total Monthly Payment does not include the estimated HOA/Common Charge payment.