9575 Westover Roberts Rd, Windermere, FL 34786
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Property image
FOR SALE
3D VIEW
4.27 ACRES

9575 Westover Roberts Rd
Windermere, FL 34786

  • 7 Beds
  • 8 Baths
  • 8,931 sqft (on 4.27 acres)

$4,850,000

Original price: $4,925,000
Est. Mortgage $32,903/mo*
Get Pre-Qualified

$4,850,000

Original price: $4,925,000
Est. Mortgage $32,903/mo*
Get Pre-Qualified
7 Beds
8 Baths
8,931 sqft
(on 4.27 acres)

Local Information

  • Map ViewExplore the area around 9575 Westover Roberts Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

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.

Home Highlights

Parking
6 Car Garage
Outdoor
Porch, Patio, Deck, Pool
View
Pool, Water, Lake
HOA
None
Price/Sqft
$543
Listed
180+ days ago

Home Details for 9575 Westover Roberts Rd

Interior Features

Interior Details
Number of Rooms: 13Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Bonus Room, Den, Dining Room, Family Room, Kitchen, Living Room, Media RoomWet Bar
Beds & Baths
Number of Bedrooms: 7Number of Bathrooms: 8Number of Bathrooms (full): 8
Dimensions and Layout
Living Area: 8931 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Available, Electricity Available, Electricity Connected, Sprinkler MeterAppliances: 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 RefrigeratorDishwasherDisposalDryerLaundry: In Garage,Inside,Laundry Closet,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,Electric,Heat Pump,Propane,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Family Room, Gas, Other RoomSpa: In GroundHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Blinds, Window TreatmentsDoor: French Doors, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sliding DoorsFlooring: Carpet, Ceramic Tile, Granite, Marble, Travertine, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Carpet, Ceramic Tile, Granite, Marble, Travertine, Hardwood
View
Has a ViewView: Pool, Water, Lake
Security
Security: Closed Circuit Camera(s), Security Gate, Security Lights, Security System, Security System Owned, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Covered, Deck, Front Porch, Patio, Porch, Rear Porch, ScreenedFencing: FencedVegetation: Mature Landscaping, Trees/LandscapedOther Structures: Boat House, Guest House, Outdoor Kitchen, StorageExterior: Balcony, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Private Mailbox, Rain Gutters, Sprinkler MeteredFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 6Number of Covered Spaces: 6Other Parking: Garage Dimensions: 50X26No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Boat,Circular Driveway,Driveway,Garage Door Opener,Garage Faces Side,Guest,Oversized,Split Garage
Pool
Pool: Child Safety Fence, Deck, Fiber Optic Lighting, Gunite, Heated, In Ground, Infinity, Lighting, Salt Water, Screen Enclosure, TilePool
Frontage
WaterfrontWaterfront: Lake Front, Lake Privileges, Boat Ramp - Private, Fishing Pier, Lift, Lift - Covered, Skiing AllowedRoad Surface Type: Paved, BrickOn Waterfront
Water & Sewer
Sewer: Septic TankWater Body: LAKE OLIVIA

Days on Market

Cumulative Days on Market: 181Days on Market: 180+

Property Information

Year Built
Year Built: 2008
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Custom,Mediterranean
Building
Construction Materials: Block, StuccoNot a New ConstructionNot Attached PropertyNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Condition: CompletedParcel Number: 282233310011100

Price & Status

Price
List Price: $4,850,000Price Per Sqft: $543

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: WINDERMERECommunity: GOTHA TOWN
School Information
Elementary School: Thornebrooke ElemJr High / Middle School: Gotha MiddleHigh School: Olympia High

Agent Information

Listing Agent
Listing ID: O6357873

Building

Building Area
Building Area: 13977 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 4.27 Acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6357873Water ViewWater View: Water, LakeShowing AttendedShowing Requirements: Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12095-N-282233310011100-R-N
Last check for updates: about 1 hour ago
Listing Provided by: Rob Rahter, (407) 497-4526
STOCKWORTH REALTY GROUP, (407) 909-5900
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6357873
Also Listed on Stellar MLS.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Market trends in Windermere

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$722K
$50KMoM
Sale-to-List Price
97.3%
0.2%MoM
Price per sq ft
$273
$11MoM
Available listings
285
6MoM

Price History for 9575 Westover Roberts Rd

DatePriceEventSource
05/11/2026$4,850,000PriceChange
Stellar MLS #O6357873
11/11/2025$4,925,000Listed For SaleStellar MLS #O6357873
04/10/2023ListingRemovedStellar MLS #O6060334
02/01/2023$4,900,000PriceChange
Stellar MLS #O6060334
10/05/2022$4,990,000Listed For SaleStellar MLS #O6060334
11/12/2020$2,000,000Sold
N/A
04/18/2020$2,650,000PendingAgent Provided
11/27/2019$2,650,000PriceChange
Agent Provided
09/26/2019$2,699,999PriceChange
Agent Provided
03/23/2019$2,750,000Listed For SaleAgent Provided
08/28/2018$2,750,000ListingRemovedAgent Provided
03/09/2018$2,750,000PriceChange
Agent Provided
01/31/2018$2,975,000PriceChange
Agent Provided
12/15/2017$2,999,900Listed For SaleAgent Provided
10/30/2013$2,600,000Sold
N/A
05/22/2013$2,650,000PriceChange
Agent Provided
04/02/2013$2,750,000PriceChange
Agent Provided
11/05/2011$2,900,000PriceChange
Agent Provided
12/05/2010$3,900,000Listed For SaleAgent Provided
06/11/2010$4,900,000ListingRemovedAgent Provided
12/30/2009$4,900,000Listed For SaleAgent Provided
10/15/2007$1,450,000Sold
N/A
03/31/2000$215,000Sold
N/A
08/19/1996$695,700Sold
N/A

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Property Tax and Assessment

Year2024
Tax$30,908
Assessment$2,632,905
Home facts updated by county records

Comparable Sales for 9575 Westover Roberts Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1703 Roberts Landing Rd, Windermere, FL
0.24
Single-Family Home
$1,355,000
07/10/26
4
4.5
3,288
9649 Weatherstone Ct, Windermere, FL
0.47
Single-Family Home
$1,300,000
12/18/25
5
5
4,226
1724 Windermeredown Pl, Windermere, FL
0.90
Single-Family Home
$2,404,000
01/15/26
6
7.5
8,137
9439 Westover Club Cir, Windermere, FL
0.36
Single-Family Home
$1,099,995
10/24/25
6
4.5
4,445
10545 Down Lakeview Cir, Windermere, FL
0.98
Single-Family Home
$3,450,000
01/23/26
5
5.5
7,263
9641 Crown Prince Ln, Windermere, FL
0.40
Single-Family Home
$1,070,000
09/30/25
5
4
3,924
2624 Midsummer Dr, Windermere, FL
0.70
Single-Family Home
$2,500,000
09/05/25
4
2.5
4,667
1420 Dingens Ave, Windermere, FL
0.52
Single-Family Home
$1,610,000
05/11/26
4
3.5
4,072
1450 Belfiore Way, Windermere, FL
0.55
Single-Family Home
$1,435,000
11/12/25
5
4.5
4,477
1924 Katie Hill Way, Windermere, FL
0.26
Single-Family Home
$935,000
12/19/25
5
3
4,089

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 9575 Westover Roberts Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Windermere

At least 270 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 92 % Say there are sidewalks

  • 87 % Say car is needed

  • 87 % Say parking is easy

  • 81 % Say people would walk alone at night

  • 80 % Say it's quiet

  • 79 % Say there's holiday spirit

  • 78 % Say kids play outside

  • 75 % Say streets are well-lit

  • 64 % Say yards are well-kept

  • 60 % Say they plan to stay for at least 5 years

  • 59 % Say it's walkable to grocery stores

  • 56 % Say there's wildlife

  • 55 % Say it's walkable to restaurants

  • 54 % Say neighbors are friendly

  • 40 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Anjalique Creative Concepts
    "We’ve lived in this area for 5 years and absolutely love it! The people in the community are always friendly, welcoming and supportive of one another. All the surrounding neighborhoods are well maintained and there are always organized activities in the community that makes it fun to meet new residents moving in."
    0
    Flag
  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
    0
    Flag
  • Valentina
    "Trick or treating is big but it’s more about small groups of neighbors doing things together rather than large activities in the entire neighborhood."
    0
    Flag
  • Juliana Daurio
    "I moved to Windermere in 2004. When my kids were 3 and 4. This feels like home since then. Now that my kids are gone I see no need to move. I have many nice neighbors and enjoy everything that this area has to offer. "
    0
    Flag
  • Snkdrwbwms
    "Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
    0
    Flag
  • Snkdrwbwms
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
    0
    Flag
  • Juliana Daurio
    "Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
    0
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  • Datylberman
    "I work at home so I’m not versed in the commute anywhere.many people in Windermere work at hone also.friends who work downtown are happy with their commute."
    0
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  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
    0
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  • Garrett Hendrickson
    "Some home owners don’t want neighbors dogs to relieve themselves in their yard. This is even if you clean up after your pet. "
    0
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  • Ngandhi62
    "Great areas to walk dogs and great puppy parks. Very close convenient veterinarians and pet supply stores. There are also many pet owners in area, therefore a nice social community is created."
    5
    Flag
  • Sean H.
    "It is a very pet friendly neighborhood. And has many fenced in dog areas and 90% of people are respectful enough to clean up after their dogs."
    3
    Flag
  • Limegreenlilo
    "Quiet & neighbors look out for one another. We have a FB page for residents to help each other out. I have been a resident ten years and love living here. HOA is good and they keep everything nice."
    0
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  • Carylpalmerini17
    "Great place to raise children and just enjoy life. Schools are amazing and the 4th is no joke. Get a move on ....."
    3
    Flag
  • Carylpalmerini17
    "Great place to live in. Everyone has been kind, neighborhood is well kept, activities are always taking place. "
    3
    Flag
  • Shariel A.
    "tons of baggies available. tons of space and good clean environment for your pets. worth living for safety and pet compliance. "
    1
    Flag
  • Msldancer
    "See lots of dogs in the area, most are very social. But I do not like that some owners do not put their dogs on leashes, they also then get mad when you come by even though you’re dog is leashes as it should be."
    2
    Flag
  • Mckenziejl
    "They would like the many trails and dog parks. Most of the neighborhoods are not gated or man guarded, so you can easily move in and out of them. Each neighborhood is unique and wherher you're going for walk with or without you pet, the time would be enjoyable."
    0
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  • Jessica
    "30min or less to get to any of the central Florida locations. Some locations can even see fireworks. Traffic can be a little heavy during the am/pm rush but nothing super crazy."
    2
    Flag
  • Stephanie F.
    "Easy to get to Disney. I work on Disney property. High traffic during rush hour times. Very quick during non peak rush hour times. "
    1
    Flag
  • Afanador713
    "Great parks for families to bike, walk and enjoy a picnic. The area is beautiful, homes are very well cared for."
    0
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  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
    0
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  • David M.
    "I’ve lived in Windermere for 3+ years and absolutely love it! Great schools, homes and atmosphere! Wouldnt live in any other neighborhood! "
    0
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  • Jessica
    "lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
    2
    Flag
  • Fabiana B.
    "Great family neighborhood. Great Lakes for water activities. Good for walking with your family, pet or go for a bike ride. "
    1
    Flag
  • Dasom.jang
    "It’s a nice and safe area to live in. There isn’t much going on, but there are food truck nights once a month, and farmer’s market on every Saturday in Winter Garden. "
    0
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  • John F.
    "I have lived in Windermere for 20 years. Very safe and good clean people. The cops are very responsive and people are rich and have class "
    0
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  • Anthony G.
    "People are very family oriented. Neighbors came about the appearance and condition of their property."
    0
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  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
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  • Evelyn T.
    "It’s a small oasis away from the hustle and bustle of such a vacation heavy town. I love getting to feel like I’m actually away from work and in a calm space but still be a 20 minute commute."
    1
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  • Alex P.
    "Great neighborhood. Family oriented. Great schools. Affluent, but not overly pretentious. Not much to in town. "
    0
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  • Jessica M.
    "Great neighborhood, great people, great atmosphere. I always love visiting this area. Communities are kept clean and look inviting. "
    1
    Flag
  • Jamesgkoshy
    "Quiet neighborhood, that is short distance to major attractions. Safe with great schools. Beautiful, clean and uncrowded. "
    0
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  • Loypippin
    "It’s a safe area but growing too quickly. Too many new houses and schools getting crowded. The schools are great, but need to be built faster to keep up. "
    1
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  • Beverly B.
    "It is very safe well lighted small community with many families with and without children. Everyone is friendly and keep their properties in great shape"
    0
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  • Joanna T.
    "Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
    1
    Flag
  • Princess J.
    "Great place to live, and I feel safe in this area. I moved to this area when I moved to Florida and it was the best decision. "
    1
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  • Windy
    "Nice , clean , safe area . Okay with my kids playing out side with other kids. Nice pool area friendly people . "
    0
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LGBTQ Local Legal Protections

Rob Rahter, STOCKWORTH REALTY GROUP, (407) 909-5900
Agent Phone: (407) 497-4526
9575 Westover Roberts Rd, Windermere, FL 34786 is a 7 bedroom, 8 bathroom, 8,931 sqft single-family home built in 2008. This property is currently available for sale and was listed by Stellar MLS on Nov 11, 2025. The MLS # for this home is MLS# O6357873.