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For sale
    • Price cut: $75K (5/11)
    $4,850,000

    9575 WESTOVER ROBERTS ROAD, WINDERMERE, FL 34786

    7beds
    8,931sqft
    : 
    $33,152/mo
    Get pre-qualified
    Single Family Residence
    Built in 2008
    4.27 Acres Lot
    $4,364,000 Zestimate®
    $543/sqft
    $-- HOA

    What's special

    Refreshed covered dockGuest suiteExpansive luxury residenceThree islandsBrand new roofCustom iron railingsBeautiful marble counters
    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.
    263 days
    |
    1,713
    |
    136
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Rob Rahter 407-497-4526,

    STOCKWORTH REALTY GROUP 407-909-5900

    Source: Stellar MLS,MLS#: O6357873MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 7
      • Bathrooms: 8
      • Full bathrooms: 8
      Rooms
      • Room types: Bonus Room, Breakfast Room Separate, Den/Library/Office, Family Room, Dining Room, Living Room, Utility Room, Media Room, Storage Rooms
      Primary bedroom
      • Description: Room13
      • Features: Bath w Spa/Hydro Massage Tub, Dual Closets
      • Level: First
      • Area: 432 Square Feet
      • Dimensions: 24x18
      Primary bedroom
      • Description: Room12
      • Features: Bath w Spa/Hydro Massage Tub, Wet Bar, Walk-In Closet(s)
      • Level: Second
      • Area: 289 Square Feet
      • Dimensions: 17x17
      Bedroom 2
      • Description: Room1
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 336 Square Feet
      • Dimensions: 21x16
      Bedroom 3
      • Description: Room2
      • Features: Ceiling Fan(s), Walk-In Closet(s)
      • Level: Second
      • Area: 216 Square Feet
      • Dimensions: 18x12
      Bedroom 4
      • Description: Room3
      • Features: Ceiling Fan(s), Walk-In Closet(s)
      • Level: Second
      • Area: 210 Square Feet
      • Dimensions: 15x14
      Bedroom 5
      • Description: Room4
      • Features: Ceiling Fan(s), Walk-In Closet(s)
      • Level: Second
      • Area: 208 Square Feet
      • Dimensions: 16x13
      Bonus room
      • Description: Room5
      • Features: No Closet
      • Level: First
      • Area: 323 Square Feet
      • Dimensions: 19x17
      Den
      • Description: Room6
      • Features: Ceiling Fan(s)
      • Level: First
      • Area: 168 Square Feet
      • Dimensions: 14x12
      Dining room
      • Description: Room7
      • Level: First
      • Area: 240 Square Feet
      • Dimensions: 20x12
      Family room
      • Description: Room8
      • Features: Ceiling Fan(s)
      • Level: First
      • Area: 484 Square Feet
      • Dimensions: 22x22
      Kitchen
      • Description: Room10
      • Features: Granite Counters, Kitchen Island, Pantry, Stone Counters
      • Level: First
      • Area: 336 Square Feet
      • Dimensions: 21x16
      Living room
      • Description: Room11
      • Level: First
      • Area: 345 Square Feet
      • Dimensions: 23x15
      Media room
      • Description: Room9
      • Level: First
      • Area: 408 Square Feet
      • Dimensions: 24x17
      Heating
      • Central, Electric, Heat Pump, Propane, Zoned
      Cooling
      • Central Air, Zoned
      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: In Garage, Inside, Laundry Closet, Laundry Room
      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
      • Flooring: Carpet, Ceramic Tile, Granite, Marble, Travertine, Hardwood
      • Doors: French Doors, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sliding Doors
      • Windows: Window Treatments
      • Has fireplace: Yes
      • Fireplace features: Family Room, Gas, Other Room
      Interior area
      • Total structure area: 13,977
      • Total interior livable area: 8,931 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 6
      • Parking features: Boat, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Guest, Oversized, Split Garage
      • Attached garage spaces: 6
      • Has uncovered spaces: Yes
      • Details: Garage Dimensions: 50X26
      Features
      • Levels: Two
      • Stories: 2
      • 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 private pool: Yes
      • Pool features: Child Safety Fence, Deck, Fiber Optic Lighting, Gunite, Heated, In Ground, Infinity, Lighting, Salt Water, Screen Enclosure, Tile
      • 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
      • Waterfront features: Lake Front, Lake Privileges, Boat Ramp - Private, Fishing Pier, Lift, Lift - Covered, Skiing Allowed
      • Body of water: LAKE OLIVIA
      Lot
      • Size: 4.27 Acres
      • Dimensions: 183 x 1295 x 183 x 1295
      • Features: Private
      • Residential vegetation: Mature Landscaping, Trees/Landscaped
      Details
      • Additional structures: Boat House, Guest House, Outdoor Kitchen, Storage
      • Parcel number: 282233310011100
      • Zoning: R-CE
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Custom,Mediterranean
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco
      • Foundation: Slab
      • Roof: Tile
      Condition
      • Completed
      • New construction: No
      • Year built: 2008

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: BB/HS Internet Available, Cable Available, Electricity Available, Electricity Connected, Sprinkler Meter

      Community & HOA

      Community
      • Security: Closed Circuit Camera(s), Security Gate, Security Lights, Security System, Security System Owned, Smoke Detector(s)
      • Pet fee: $0 monthly
      • Subdivision: GOTHA TOWN
      HOA
      • Has HOA: No
      Location
      • Region: Windermere

      Financial & listing details

      • Price per square foot: $543/sqft
      • Tax assessed value: $2,632,905
      • Annual tax amount: $30,908
      • Date on market: 11/11/2025
      • Cumulative days on market: 263 days
      • Listing terms: Cash,Conventional
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved, Brick

        Estimated market value

        $4,364,000

        $4.15M - $4.58M

        $8,499/mo

        Price history

        DateEventPrice
        5/11/2026Price change$4,850,000-1.5%$543/sqft
        Source: Stellar MLS #O6357873 Report a problem
        11/11/2025Listed for sale$4,925,000+0.5%$551/sqft
        Source: Stellar MLS #O6357873 Report a problem
        4/10/2023Listing removed--
        Source: Stellar MLS #O6060334 Report a problem
        2/1/2023Price change$4,900,000-1.8%$549/sqft
        Source: Stellar MLS #O6060334 Report a problem
        10/5/2022Listed for sale$4,990,000+149.5%$559/sqft
        Source: Stellar MLS #O6060334 Report a problem
        11/12/2020Sold$2,000,000-24.5%$224/sqft
        Source: Public Record Report a problem
        4/18/2020Pending sale$2,650,000$297/sqft
        Source: CHARLES RUTENBERG REALTY ORLANDO #O5772066 Report a problem
        11/27/2019Price change$2,650,000-1.9%$297/sqft
        Source: CHARLES RUTENBERG REALTY ORLANDO #O5772066 Report a problem
        9/26/2019Price change$2,699,999-1.8%$302/sqft
        Source: CHARLES RUTENBERG REALTY ORLANDO #O5772066 Report a problem
        3/23/2019Listed for sale$2,750,000$308/sqft
        Source: CHARLES RUTENBERG REALTY ORLANDO #O5772066 Report a problem
        8/28/2018Listing removed$2,750,000$308/sqft
        Source: PREMIER REALTY PARTNERS INC #O5552133 Report a problem
        3/9/2018Price change$2,750,000-7.6%$308/sqft
        Source: PREMIER REALTY PARTNERS INC #O5552133 Report a problem
        1/31/2018Price change$2,975,000-0.8%$333/sqft
        Source: PREMIER REALTY PARTNERS INC #O5552133 Report a problem
        12/15/2017Listed for sale$2,999,900+15.4%$336/sqft
        Source: PREMIER REALTY PARTNERS INC #O5552133 Report a problem
        10/30/2013Sold$2,600,000-1.9%$291/sqft
        Source: Public Record Report a problem
        5/22/2013Price change$2,650,000-3.6%$297/sqft
        Source: Stirling Sotheby's International Realty #o5129690 Report a problem
        4/2/2013Price change$2,750,000-5.2%$308/sqft
        Source: Stirling Sotheby's International Realty #o5129690 Report a problem
        11/5/2011Price change$2,900,000-25.6%$325/sqft
        Source: Oxford Realty, Inc. International Luxury & Estate Brokers #O4946758 Report a problem
        12/5/2010Listed for sale$3,900,000-20.4%$437/sqft
        Source: Oxford Realty, Inc. #O4946758 Report a problem
        6/11/2010Listing removed$4,900,000$549/sqft
        Source: Oxford Realty, Inc #O4946758 Report a problem
        12/30/2009Listed for sale$4,900,000+237.9%$549/sqft
        Source: Oxford Realty, Inc #O4946758 Report a problem
        10/15/2007Sold$1,450,000+574.4%$162/sqft
        Source: Public Record Report a problem
        3/31/2000Sold$215,000-69.1%$24/sqft
        Source: Public Record Report a problem
        8/19/1996Sold$695,700$78/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$30,908 +7.4%$1,922,045 +3%
        2023$28,790 +2.9%$1,866,063 +3%
        2022$27,990 +1.7%$1,811,712 +3.6%
        2021$27,529 -27.8%$1,749,235 -27.1%
        2020$38,144 +0.7%$2,399,685 +2.3%
        2019$37,879 +0.7%$2,345,733 +1.9%
        2018$37,633 $2,301,995 -7.1%
        2017$37,633 +1%$2,477,631 +2.4%
        2016$37,262 +0%$2,419,248 +10.1%
        2015$37,259 -2.2%$2,196,859 +1.4%
        2014$38,101 +69.3%$2,165,598 +19.5%
        2013$22,499 +1%$1,812,809 +4.5%
        2012$22,285 +2.6%$1,734,222 -1.9%
        2011$21,717 +4.2%$1,767,789 -0.8%
        2010$20,837 $1,782,828 +197.5%
        2009-- $599,365 -55.8%
        2008$19,714 -15.2%$1,357,198 -3.6%
        2007$23,248 +50.5%$1,407,842 +13.5%
        2006$15,443 -0.1%$1,240,009 +7.6%
        2005$15,459 +4.3%$1,152,009 +39.4%
        2004$14,820 -1.3%$826,273 -0.9%
        2003$15,019 +2.5%$833,867 +3.9%
        2002$14,652 $802,788
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 34786

        Getting around

        11 / 100
        Car-Dependent
        34 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Thornebrooke Elem
        • Middle: Gotha Middle
        • High: Olympia High

        Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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