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$4,750,000

9575 WESTOVER ROBERTS RD
WINDERMERE, FL 34786
Listed by Rob Rahter · STOCKWORTH REALTY GROUP
Bedrooms
7
Bathrooms
8
Living area
8,931 sqft
Year built
2008

About this home

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.

Highlights

WaterfrontPrivate poolFireplace

Property details

MLS
Stellar MLS
MLS #
MFRO6357873
Property type
Single Family Residence
Subdivision
GOTHA TOWN
Status
Active
Days on market
311
On market date
November 11, 2025
Stories
N/A
Total bathrooms
8
Garage spaces
6
Parking spaces
N/A
Lot size
5.44 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
THORNEBROOKE ELEMENTARY
1.05 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
617
Student:teacher ratio
15.0:1
District
ORANGE
Middle
GOTHA MIDDLE
0.69 mi away · Grades 6-9
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,084
Student:teacher ratio
19.4:1
District
ORANGE
High
OLYMPIA HIGH
1.73 mi away · Grades 8-12
Nearest school -- attendance-zone data not available here
1.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
2,878
Student:teacher ratio
24.8:1
District
ORANGE

Walkability

Blended score for WINDERMERE's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

36
Car-dependent
out of 100
EPA National Walkability Index
9.0 / 20 -- Below average walkable
Google Places amenity density
23 / 100
Restaurants & cafes3
Grocery stores0
Parks1
Schools2
Transit stops0
Pharmacies0

Market position

How this listing compares to current activity in WINDERMERE, from live MLS data.

On the market 311 days -- 234 more days than WINDERMERE's current average of 77 days.
For reference, the median list price across 393 active listings in WINDERMERE right now is $740,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$28,755/mo
$950,000 down
$3,800,000 loan
Principal & interest$24,647
Property tax (est.)$3,958
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated September 18, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.