See other homes in:
Primary listing photo
Listing photo 2
Listing photo 3
Listing photo 4
Listing photo 5

9575 Westover Roberts Rd, Windermere, FL, 34786

7beds
8baths
8,931sqft
$4,850,000
$543price/sqft
$35,290/moest. monthly cost
$1,411,600/yrincome needed

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.

Getting Around

11
WalkingCar-Dependent
0
TransitVery Limited Transit
34
BikeSomewhat Bikeable

Schools

10/10
5/10
Gotha Middle SchoolGrades 6-80.5 mi
5/10
Olympia High SchoolGrades 9-121.7 mi

Construction

Condition

  • Property condition: Completed
  • Year built: 2008

Materials

  • Foundation: Slab
  • Roof: Tile
  • Construction materials: Block,Stucco

Type & Style

  • Home type: SingleFamily
  • Architectural style: Custom,Mediterranean
  • Property subType: Single Family Residence

Interior

Appliances

  • Appliances included: Bar Fridge,Oven,Cooktop,Dishwasher,Disposal,Dryer,Electric Water Heater,Exhaust Fan,Freezer,Microwave,Range,Range Hood,Refrigerator,Tankless Water Heater,Washer,Water Softener,Wine Refrigerator
  • Laundry features: In Garage,Inside,Laundry Closet,Laundry Room

Bedroom2

  • Features: Walk-In Closet(s)
  • Level: First
  • Area: 336
  • Dimensions: 21x16

Bedroom3

  • Features: Ceiling Fan(s),Walk-In Closet(s)
  • Level: Second
  • Area: 216
  • Dimensions: 18x12

Bedroom4

  • Features: Ceiling Fan(s),Walk-In Closet(s)
  • Level: Second
  • Area: 210
  • Dimensions: 15x14

Bedroom5

  • Features: Ceiling Fan(s),Walk-In Closet(s)
  • Level: Second
  • Area: 208
  • Dimensions: 16x13

Bedrooms & Bathrooms

  • Bedrooms: 7
  • Bathrooms: 8
  • Full bathrooms: 8

Bonus Room

  • Features: No Closet
  • Level: First
  • Area: 323
  • Dimensions: 19x17

Den

  • Features: Ceiling Fan(s)
  • Level: First
  • Area: 168
  • Dimensions: 14x12

Dining Room

  • Level: First
  • Area: 240
  • Dimensions: 20x12

Family Room

  • Features: Ceiling Fan(s)
  • Level: First
  • Area: 484
  • Dimensions: 22x22

Features

  • Cathedral Ceiling(s),Ceiling Fan(s),Coffered Ceiling(s),Crown Molding,Eating Space In Kitchen,High Ceilings,Kitchen/Family Room Combo,Primary Bedroom Main Floor,PrimaryBedroom Upstairs,Solid Surface Counters,Split Bedroom,Stone Counters,Vaulted Ceiling(s),Walk-In Closet(s),Wet Bar
  • Door features: French Doors,Outdoor Grill,Outdoor Kitchen,Outdoor Shower,Sliding Doors
  • Window features: Blinds,Double Pane Windows,Window Treatments
  • Flooring: Carpet,Ceramic Tile,Granite,Marble,Travertine,Hardwood
  • Fireplace features: Family Room,Gas,Other Room
  • Fireplace: Yes

Heating & Cooling

  • Heating features: Central,Electric,Heat Pump,Propane,Zoned
  • Cooling features: Central Air,Zoned

Interior Area

  • Total structure area: 13,977
  • Total interior livable area: 8,931 sqft

Kitchen

  • Features: Granite Counters,Kitchen Island,Pantry,Stone Counters
  • Level: First
  • Area: 336
  • Dimensions: 21x16

Living Room

  • Level: First
  • Area: 345
  • Dimensions: 23x15

Media Room

  • Level: First
  • Area: 408
  • Dimensions: 24x17

Primary Bedroom

  • Features: Bath w Spa/Hydro Massage Tub,Dual Closets
  • Level: First
  • Area: 432
  • Dimensions: 24x18

Primary Bedroom

  • Features: Bath w Spa/Hydro Massage Tub,Wet Bar,Walk-In Closet(s)
  • Level: Second
  • Area: 289
  • Dimensions: 17x17

Property

Details

  • Parcel number: 282233310011100
  • Zoning: R-CE
  • Special condition: None

Features

  • Levels: Two
  • Stories: 2
  • Private pool: Yes
  • Pool features: Child Safety Fence,Deck,Fiber Optic Lighting,Gunite,Heated,In Ground,Infinity,Lighting,Salt Water,Screen Enclosure,Tile
  • Patio & porch: Covered,Deck,Front Porch,Patio,Porch,Rear Porch,Screened
  • Exterior features: Balcony,Irrigation System,Lighting,Outdoor Grill,Outdoor Kitchen,Outdoor Shower,Private Mailbox,Rain Gutters,Sprinkler Metered
  • Has spa: Yes
  • Spa features: In Ground
  • Fencing: Fenced
  • Has view: Yes
  • View description: Pool,Water,Lake
  • Has water view: Yes
  • Water view: Water,Lake
  • On waterfront: Yes
  • Waterfront features: Lake Front,Lake Privileges,Boat Ramp - Private,Fishing Pier,Lift,Lift - Covered,Skiing Allowed
  • Waterbody name: LAKE OLIVIA
  • Residential vegetation: Mature Landscaping,Trees/Landscaped

Lot

  • Lot size: 4.27 Acres
  • Features: Private
  • Lot size dimensions: 183 x 1295 x 183 x 1295

Parking

  • Total spaces: 6
  • Parking features: Boat,Circular Driveway,Driveway,Garage Door Opener,Garage Faces Side,Guest,Oversized,Split Garage
  • Has garage: Yes
  • Attached garage spaces: 6
  • Covered spaces: 6
  • Has uncovered spaces: Yes

Climate Risk is Financial Risk

Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.

Biggest Threats for This Home

  • Strong Wind
    Strong WindVery High
  • Cold Wave
    Cold WaveRelatively High
  • Tornado
    TornadoRelatively High
  • Hail
    HailModerate
  • Hurricane
    HurricaneModerate
  • Inland Flooding
    Inland FloodingModerate
  • Lightning
    LightningModerate

How This Home’s Risks Compare

Strong Wind
Cold Wave
Tornado
Hail
Hurricane
Inland Flooding
Lightning

FEMA Declared Disasters in Orange County and Florida

Coastal Storm
Flood
Hurricane
Severe Storm
Straight Line Winds
Tornado
Tropical Depression
Tropical Storm

Understanding the Costs

Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.

Estimated Costs Today

MonthlyAnnual
Mortgage $24,524$294,288
Home Insurance *$3,444$41,328
Property Taxes $6,424$77,088
Electricity $898$10,785
Total$35,290$423,480
*Does not include cost of any FAIR Plan premiums

Income You'd Need if You Spent...

35% on housing$1,209,942/yr
40% on housing$1,058,700/yr
45% on housing$941,066/yr

Florida FAIR Plan Programs

Citizens Property Insurance Corporation [Florida]

Covered
WildfireWildfire
HailHail
WindWind
Visit Website →
Current Policies
Residential: 1,321,953Commercial: 13,564
Total Premiums$4.60B
Total Exposure$385.82B

How Costs Could Change Over Time

Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.

Insurance Growth Rate5-year average: 14.0%
14.0%
0%30.0%
Electricity Growth Rate10-year average: 2.2%
2.2%
0%15.0%
Property Taxes Growth Rate2-year average: 3.0%
3.0%
0%15.0%
Income Spent on Housing
30%
30%45%

Comparing Against the Market

Price Per Sq Ft

$543This listing

vs Other Active Listings

Avg $/sqft

ZIP 34786$464
Orange County$236

vs Homes Sold Last Month

Median $/sqft

ZIP 34786$296
Orange County$245

Current Market Trends

Median Price Per Square Foot

The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.

Historicals for This Listing

Zestimate History ($/sqft)

Price History

DateEventPrice
2026-05-11Price change$4,850,000
2025-11-11Listed for sale$4,925,000
2023-04-10Listing removed--
2023-02-01Price change$4,900,000
2022-10-05Listed for sale$4,990,000
2020-11-12Sold$2,000,000
2020-04-18Pending sale$2,650,000
2019-11-27Price change$2,650,000
2019-09-26Price change$2,699,999
2019-03-23Listed for sale$2,750,000
2018-08-28Listing removed$2,750,000
2018-03-09Price change$2,750,000
2018-01-31Price change$2,975,000
2017-12-15Listed for sale$2,999,900
2013-10-30Sold$2,600,000
2013-05-22Price change$2,650,000
2013-04-02Price change$2,750,000
2011-11-05Price change$2,900,000
2010-12-05Listed for sale$3,900,000
2010-06-11Listing removed$4,900,000
2009-12-30Listed for sale$4,900,000
2007-10-15Sold$1,450,000
2000-03-31Sold$215,000
1996-08-19Sold$695,700

For Sale by Agent

AgentRob Rahter
BrokerageSTOCKWORTH REALTY GROUP

Similar Homes