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9575 WESTOVER ROBERTS ROAD
WINDERMERE FL 34786 US

$4,925,000

Active Listing ID O6357873
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7 bed
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8.00 Bath (8 Full)
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Lot: 5.44 Acres
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Single Family Residence

$4,925,000

Active Listing ID O6357873
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9575 WESTOVER ROBERTS ROAD 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 Features

  • Facts
  • Lot Size: 5.44 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 8
  • Cooling System: Central Air, Zoned
  • Exterior Finish: Paved, Fencing, Balcony, French Doors, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Private Mailbox, Rain Gutters, Sliding Doors, Sprinkler Metered, Pool, Dock, Security Lights
  • Floor Covering: Carpet, Granite, Marble, Tile, Tile - Ceramic, Wood
  • Roof Type: Tile
  • Heating Fuels: Central, Electric (Heating), Fireplace(s), Heat Pump (Heating), Propane (Heating), Zoned (Heating)
  • Additional Features
  • Fireplace
  • Pool
  • Waterfront

School Information

  • School
  • Thornebrooke Elem(Elementary)
  • Gotha Middle(MiddleSchool)
  • Olympia High(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 4925000
  • unparsedaddress: 9575 WESTOVER ROBERTS ROAD
  • postalcity: WINDERMERE
  • stateorprovince: FL
  • country: US
  • postalcode: 34786
  • bathroomsfull: 8
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 5.44
  • lotsizeunits: Acres
  • lotsizearea: 5.44
  • livingarea: 8931
  • livingareaunits: Square Feet
  • latitude: 28.520897
  • longitude: -81.518066
  • listagentfullname: Rob Rahter
  • listagentemail: rob@stockworth.com
  • listagentkey: 3yd-MFRMLSFL-261090118
  • listagentmlsid: 261090118
  • listagentpreferredphone: 4079095900
  • listagentofficephone: 4079095900
  • listofficekey: 3yd-MFRMLSFL-50198
  • listagentstatelicense: 3129153
  • listofficemlsid: 50198
  • disclaimer: Copyright © 2025 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: MFRMLSFL
  • yearbuilt: 2008
  • listingcontractdate: 2025-11-11
  • listagenturl: http://www.stockworth.com
  • countyorparish: Orange
  • parcelnumber: 28-22-33-3100-11-100
  • elementaryschool: Thornebrooke Elem
  • highschool: Olympia High
  • appliances: Cooktop, Dishwasher, Dryer, Freezer, Garbage Disposer, Microwave, Range, Refrigerator, Refrigerator - Wine Storage, Washer, Water - Softener
  • cooling: Central Air, Zoned
  • constructionmaterials: Block, Stucco
  • flooring: Carpet, Granite, Marble, Tile, Tile - Ceramic, Wood
  • heating: Central, Electric (Heating), Fireplace(s), Heat Pump (Heating), Propane (Heating), Zoned (Heating)
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Boat, Driveway, Garage, Garage - Attached, Guest, Oversized
  • roof: Tile
  • waterfrontyn: True
  • interiorfeatures: Cathedral Ceiling(s), Ceiling Fans(s), Coffered Ceiling(s), Crown Molding, Eat-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, Window Treatments
  • exteriorfeatures: Paved, Fencing, Balcony, French Doors, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Private Mailbox, Rain Gutters, Sliding Doors, Sprinkler Metered, Pool, Dock, Security Lights
  • waterfrontfeatures: Lake Front, Waterfront
  • architecturalstyle: Mediterranean
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bathroom 5, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Bonus Room, Den, Dining Room, Family Room, Kitchen, Living Room, Media Room
  • securityfeatures: Closed Circuit Camera(s), Security Gate, Security Lighting, Security System, Security System Owned, Smoke Detector(s)
  • otherstructures: Outdoor Kitchen
  • structuretype: Dock
  • dock: True
  • poolprivateyn: True
  • spayn: False
  • fencing: Fenced, Gate
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.51807, 28.520897
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Stockworth Realty Group LLC", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"sales@stockworth.com", "ListBrokerageCity":"Orlando", "ListBrokerageCountry":"US", "ListBrokerageEmail":"sales@stockworth.com", "ListBrokerageLogoUrl":"http://brokerlogos.listhub.net/MFRMLSFL/df0cdd81e16e11e198751231392c982a/20131031155041382.png", "ListBrokerageName":"Stockworth Realty Group LLC", "ListBrokeragePhone":"407-909-5900", "ListBrokeragePostalCode":"32819", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"4705 S Apopka Vineland Road", "ListBrokerageWebsiteUrl":"http://www.stockworth.com", "ListOfficeAddress1":"4705 Apopka Vineland Rd #210", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":null, "ListOfficeCity":"Orlando", "ListOfficeCountry":"US", "ListOfficeEmail":"rob@stockworth.com", "ListOfficePostalCode":"32819", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Single Family Residence, Custom, Mediterranean - WINDERMERE, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/9575-Westover-Roberts-Rd_Windermere_FL_34786_M50442-64578?f=listhub&s=MFRMLSFL&m=O6357873&c=rexren", "MLSModificationTimestamp":"2025-11-11T13:47:12Z", "Neighborhoods":[], "PostalCode":null, "RawPropertySubType":"Single Family Residence", "RawPropertyType":"Residential", "RoomCount":13, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":30908, "TaxDescription":null, "TaxYear":"2024"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 12/11/2025 1:36:36 AM GMT
Source Updated Date: 12/18/2025 12:52:42 PM GMT

Courtesy of: Rob Rahter, STOCKWORTH REALTY GROUP, rob@stockworth.com

Copyright © 2025 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.