9575 WESTOVER ROBERTS ROAD, Windermere, FL, 34786 | $4,925,000

Discover “Bella Olivia”: a grand mediterranean estate perched high above Lake Olivia showcasing sweeping lake views, private gates, and an expansive luxury residence spanning over 8, 900 square feet of living space across 7 bedrooms, including two primary suites, two guest apartments, garage space for 6 cars, an enormous screened enclosure with resort-style pool and spa, over 5. 4 acres and no HOA. This private palace with brand new roof impresses with large circular paver drive, 3-tiered fountain, 10-foot iron front doors, 35-foot high ceilings, custom iron railings, and marble and travertine flooring – plus, coffered ceilings and elegant details throughout. Home has been extensively updated and lovingly cared for to highlight classic style and luxury to compliment today’s sophisticated lifestyle. The main kitchen features beautiful marble counters, three islands, two preparation sinks, custom cabinetry, and stainless appliances including two dishwashers, two microwaves, double ovens, and a Viking gas stove. The first-floor primary retreat is dressed with hardwood flooring, tray ceiling, and triple crown molding, and an exceptional bathroom with tiled shower, jetted tub, dual vanities, and expansive double closets. The main living spaces are abundant and stately with two first-floor family rooms, billiards room, living room, dining room, theater, and guest suite – upstairs is a third family room, secondary master suite, and three additional guest suites, plus a large balcony with screens. A separate entrance off the kitchen provides access to a private guest apartment with a kitchenette, family room, and bedroom. Plus, a second private apartment (978 sq feet, not included in the listed 8, 931 sq feet) is accessible from the outside and is located over the 4-car garage and features family room, sink, and bedroom. Functional outdoor living space is extended to the mammoth screened enclosure to encompass a sitting area off the master and an additional family room with fireplace, tv, and full summer kitchen across the pool deck that can be separated by an electric additional privacy screen. The showstopping infinity edge pool is colossal in size and includes a sun shelf for shallow water relaxing and an infinity hot tub. Both sides of the house have all been paved with a new drainage system and ramps for easy access for boats and watercraft to Lake Olivia. The 150 ft refreshed covered dock has two cradles: currently set for a boat and two jet skis. There’s also a sitting area for lounging lakeside. Experience the best of Windermere with this lakefront retreat built for privacy, luxury, and lifestyle.

Features

  • Rooms: 13
  • Bedrooms: 7
  • Baths: 8 full
  • Lot Size: 183 x 1295 x 183 x 1295
  • Laundry: In Garage, Inside, Laundry Closet, Laundry Room
  • Style: Custom, Mediterranean
  • Year Built: 2008
  • Garage: 6-car Boat, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Guest, Oversized, Split Garage
  • Heating: Central, Electric, Heat Pump, Propane, Zoned
  • Cooling: Central Air, Zoned
  • Approx Sq. Feet: 8,931
  • Acreage: 5.44
  • Lot Size: 183 x 1295 x 183 x 1295
  • Est. Taxes: $30,908
  • Lot Desc: Private
  • View: Pool, Water
  • Elem. School: Thornebrooke Elem
  • Middle School: Gotha Middle
  • High School: Olympia High
  • Pool: Child Safety Fence, Deck, Fiber Optic Lighting, Gunite, Heated, In Ground, Infinity, Lighting, Salt Water, Screen Enclosure, Tile
  • Pet Policy: Yes
  • Appliances: Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
  • MLS#: O6357873
  • Days on Market: 98 days
  • Website: https://www.raveis.com
    /eprop/O6357873/9575westoverrobertsroad_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 3/10/2026 3:17:07 PM)
Listing courtesy of STOCKWORTH REALTY GROUP   Phone: 407-909-5900

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NMLS Mortgage Loan Originator ID 16953

917.838.7300

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9575 WESTOVER ROBERTS ROAD, Windermere, FL, 34786

$4,925,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $3,940,000 $3,940,000 $3,940,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.500% 5.875% 5.750%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.154% 6.031% 5.991%
Monthly Tax Payment $2,576 $2,576 $2,576
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $22,371 $23,307 $32,718
Total Monthly Payment $25,072 $26,008 $35,419

* 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.