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Property for sale at 9575 WESTOVER ROBERTS ROAD, WINDERMERE, FL, 34786
Property for sale at 9575 WESTOVER ROBERTS ROAD, WINDERMERE, FL, 34786
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9575 Westover Roberts RoadWindermere, FL, 34786

7beds
8baths
8,931sqft
Single Family Residence
Built in 2008
$4,750,000
For sale
$4,925,000−$175,000 (4%)
Price per sqft
$532
Days on market
331
Listed Nov 11, 2025
Last reduction
−$100,000
Sep 14, 2026
MLS #O6357873Updated Sep 18, 2026

About this property

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.

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Property details

Property type
Single Family Residence
Street address
9575 Westover Roberts Road
City
Windermere
State
FL
ZIP code
34786
Year built
2008
New construction
No
Attached property
No
Faces
South
Rooms
13
Building stories
2
Living area
8,931 sqft
Total building area
13,977 sqft
Architectural style
Mediterranean
Levels
Two

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 8, 2026 at 12:01 AM EDT

Price & sale history

Asking price reduced by $175,000 (3.6%) since first listed.

EventPrice
Price reducedMLS #O6357873$4,750,000Change: −3.6%−$175,000
Listed for saleMLS #O6357873$4,925,000
History may be incomplete.
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Property for sale at 9575 WESTOVER ROBERTS ROAD, WINDERMERE, FL, 34786
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