11755 Waterstone Loop Dr
Windermere, FL 34786
- 5 Beds
- 5 Baths
- 3,665 sqft (on 0.29 acres)
$1,535,000
Last Sold: Sep 19, 2025
4% below list $1.59M
$419/sqft
Est. Refi. Payment $10,627/mo*
$1,535,000
Last Sold: Sep 19, 2025
4% below list $1.59M
$419/sqft
Est. Refi. Payment $10,627/mo*
5 Beds
5 Baths
3,665 sqft
(on 0.29 acres)
Local Information
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Description
Enjoy luxury living at its finest in this exceptional custom estate, Villa Milano, located within the sought after guard-gated community of Waterstone in Windermere. Built by Silliman Homes with exquisite architectural detail, this expansive one-story residence offers 3,665 square feet of impeccably designed living space, featuring 5 bedrooms, 5 full bathrooms, and a private office. A rare detached guest casita enhances the home's versatility with its own entrance, full kitchen, living area, full bath, and walk-in closet—ideal for guests, a private office, or poolside entertaining. The welcoming front courtyard, accented with timeless Chicago brick, sets the tone for refined outdoor living. Inside, soaring wood-detailed ceilings, abundant natural light, and uninterrupted views of the resort-style backyard create an inviting and open atmosphere. The formal dining room is spacious and sunlit, offering serene views of the beautifully landscaped front terrace. The gourmet kitchen is a true centerpiece, showcasing custom cabinetry, stainless steel appliances, a 5-burner gas cooktop, double ovens, granite countertops, a large island, and a walk-in pantry with concealed cabinet-door access. It opens seamlessly to the bright and inviting family room, complete with a stone-accented gas fireplace, custom wood paneled ceiling, and multiple sliding glass doors leading to the covered lanai. The luxurious owner’s suite features hardwood floors, two walk-in closets, private access to the pool area, and a spa-like bath with a seamless glass walk-in shower, soaking tub, and dual vanities. Two additional bedrooms are connected by a Jack-and-Jill bathroom, while a fourth bedroom and full bath are privately situated near the front of the home. The private office includes custom built-ins and access to a full bath, making it easily convertible to a sixth bedroom. Step outside to a true backyard oasis, complete with a custom-designed pool with water features, a heated spa, an expansive lanai with retractable screens, and an outdoor wet bar equipped with dual beverage refrigerators—perfect for entertaining. The fully fenced yard is beautifully landscaped for privacy and includes citrus trees, adding both charm and Florida flavor to the space. Additional highlights include an oversized 3-car tandem garage, 3 tankless water heater, two newer air handlers, custom shutters, Sonos audio system, no carpeting, spray foam insulation, freshly painted exterior, and premium designer finishes throughout. Waterstone is an exclusive enclave of just 120 homes along the shores of Lake Butler, offering 24-hour guarded security and a private pedestrian entrance to Windermere Preparatory School. Ideally located near upscale dining, world-class golf, boutique shopping, major theme parks, and zoned for A-rated Windermere schools. This immaculate, move-in ready estate is the essence of Florida luxury living and truly a must-see.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from September 19, 2025
Home Highlights
Parking
3 Car Garage
Outdoor
Porch, Pool
View
No Info
HOA
$433/Monthly
Price/Sqft
$419/sqft
Listed
180+ days ago
Home Details for 11755 Waterstone Loop Dr
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Interior Details Number of Rooms: 9Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Great Room, Kitchen, Office, Studio |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 5 |
Dimensions and Layout Living Area: 3665 Square Feet |
Appliances & Utilities Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Underground Utilities, Water ConnectedAppliances: Bar Fridge, Oven, Cooktop, Dishwasher, Disposal, Microwave, Range Hood, Tankless Water HeaterDishwasherDisposalLaundry: InsideMicrowave |
Heating & Cooling Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central |
Fireplace & Spa Fireplace: Gas, Living RoomSpa: Heated, In GroundHas a FireplaceHas a Spa |
Gas & Electric Has Electric on Property |
Windows, Doors, Floors & Walls Window: Double Pane Windows, Shutters, Window TreatmentsDoor: Sliding DoorsFlooring: Tile, Hardwood |
Levels, Entrance, & Accessibility Stories: 1Levels: OneFloors: Tile, Hardwood |
View No View |
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Exterior Home Features Roof: TilePatio / Porch: Covered, Rear Porch, ScreenedFencing: FencedOther Structures: Guest HouseExterior: Irrigation System, Rain Gutters, Sprinkler MeteredFoundation: SlabHas a Private Pool |
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3Other Parking: Garage Dimensions: 21X38No CarportHas a GarageHas an Attached GarageParking Spaces: 3Parking: Garage Attached |
Pool Pool: Heated, In GroundPool |
Frontage Road Surface Type: PavedNot on Waterfront |
Water & Sewer Sewer: Public Sewer |
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Cumulative Days on Market: 60 |
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Year Built Year Built: 2012 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
Building Construction Materials: Brick, StuccoNot a New ConstructionNo Additional Parcels |
Property Information Parcel Number: 242327900901150 |
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Price List Price: $1,595,000Price Per Sqft: $419/sqft |
Status Change & Dates Off Market Date: Wed Aug 20 2025 |
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MLS Status: Sold |
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Direction & Address City: WINDERMERECommunity: WATERSTONE |
School Information Elementary School: Windermere ElemJr High / Middle School: Bridgewater MiddleHigh School: Windermere High School |
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Building Details Builder Name: Silliman |
Building Area Building Area: 5245 Square Feet |
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Community Features: Deed Restrictions, SidewalksNot Senior Community |
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HOA Fee Includes: 24-Hour Guard, Common Area Taxes, Reserve Fund, Private RoadHOA Name: Sentry Management - Duketta DoloHOA Phone: 407-788-6700Association for this Listing: Orlando RegionalHas an HOAHOA Fee: $433/Monthly |
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Lot Area: 0.29 acres |
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Special Conditions: None |
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Business Information Ownership: Fee Simple |
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Mls Number: O6308061Back On Market Date: Fri Aug 01 2025Showing Requirements: ShowingTimeUniversal Property Id: US-12095-N-242327900901150-R-N |
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HOA Amenities: Fence Restrictions,Gated |
Last check for updates: about 2 hours ago
Listed by Deb Schroeder, (407) 234-2256
INFINITY REALTY GROUP LLC, (407) 234-2256
Bought with: Kaley Hansen, (352) 250-4563, COLDWELL BANKER HUBBARD HANSEN, (352) 394-4031
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6308061

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
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
Price History for 11755 Waterstone Loop Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 09/19/2025 | $1,535,000 | Sold | Stellar MLS #O6308061 |
| 08/21/2025 | $1,595,000 | Pending | Stellar MLS #O6308061 |
| 08/01/2025 | $1,595,000 | PendingToActive | Stellar MLS #O6308061 |
| 07/07/2025 | $1,595,000 | Pending | Stellar MLS #O6308061 |
| 06/09/2025 | $1,595,000 | PendingToActive | Stellar MLS #O6308061 |
| 06/03/2025 | $1,595,000 | Pending | Stellar MLS #O6308061 |
| 05/15/2025 | $1,595,000 | Listed For Sale | Stellar MLS #O6308061 |
| 04/26/2021 | $1,075,000 | Sold | N/A |
| 02/23/2021 | $1,075,000 | Pending | Agent Provided |
| 02/23/2021 | $1,075,000 | PendingToActive | Agent Provided |
| 02/23/2021 | $1,075,000 | Pending | Stellar MLS #O5923562 |
| 02/18/2021 | $1,075,000 | Listed For Sale | Stellar MLS #O5923562 |
| 02/27/2019 | $815,000 | Sold | N/A |
| 12/14/2018 | $849,990 | PriceChange | Agent Provided |
| 12/11/2018 | $859,400 | PriceChange | Agent Provided |
| 12/01/2018 | $859,500 | PriceChange | Agent Provided |
| 11/25/2018 | $859,800 | PriceChange | Agent Provided |
| 10/25/2018 | $859,900 | PriceChange | Agent Provided |
| 09/23/2018 | $879,000 | PriceChange | Agent Provided |
| 08/15/2018 | $880,000 | PriceChange | Agent Provided |
| 07/14/2018 | $890,000 | Listed For Sale | Agent Provided |
| 09/13/2015 | $993,000 | ListingRemoved | Agent Provided |
| 07/17/2015 | $993,000 | PriceChange | Agent Provided |
| 07/06/2015 | $994,000 | Listed For Sale | Agent Provided |
| 03/15/2012 | $140,000 | Sold | N/A |
Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $16,610 |
| Assessment | $1,285,391 |
Home facts updated by county records
Comparable Sales for 11755 Waterstone Loop Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.07 | Single-Family Home | $1,500,000 | 04/29/26 | 4 | 4.5 | 3,447 | |
0.04 | Single-Family Home | $1,350,000 | 04/17/26 | 4 | 4.5 | 3,396 | |
0.08 | Single-Family Home | $1,550,000 | 02/06/26 | 5 | 3.5 | 3,967 | |
0.05 | Single-Family Home | $1,370,000 | 11/04/25 | 4 | 3.5 | 3,586 | |
0.04 | Single-Family Home | $1,300,000 | 10/03/25 | 4 | 3 | 3,049 | |
0.19 | Single-Family Home | $1,400,000 | 07/11/25 | 5 | 5 | 3,894 | |
0.32 | Single-Family Home | $1,830,000 | 03/06/26 | 5 | 4.5 | 3,685 | |
0.44 | Single-Family Home | $2,000,000 | 08/25/25 | 4 | 5 | 3,966 | |
0.45 | Single-Family Home | $3,000,000 | 07/03/25 | 5 | 5.5 | 4,421 |
Assigned Schools
These are the assigned schools for 11755 Waterstone Loop Dr.
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.
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11755 Waterstone Loop Dr, Windermere, FL 34786 is a 5 bedroom, 5 bathroom, 3,665 sqft single-family home built in 2012. This property is not currently available for sale. 11755 Waterstone Loop Dr was last sold on Sep 19, 2025 for $1,535,000 (4% lower than the asking price of $1,595,000). The current Trulia Estimate for 11755 Waterstone Loop Dr is $1,521,800.