$1,535,000
SOLD SEP 19, 2025

11755 Waterstone Loop Dr Windermere, FL 34786

5 Beds
5 Baths
3,665 Sq Ft
0.29 Acres

Recently Sold

$419 Per Sq Ft

4% Below List Price

97 Days on Market

Highlights

  • Guest House
  • Heated In Ground Pool
  • Open Floorplan
  • Windermere Elementary School Rated A
  • Gated Community
  • Wood Flooring

About This Home

As of September 2025

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.

Last Agent to Sell the Property

Deb Schroeder

INFINITY REALTY GROUP LLC Brokerage Phone: 407-234-2256 License #3185131 Listed on: 05/15/2025

Last Buyer's Agent

Kaley Hansen

COLDWELL BANKER HUBBARD HANSEN License #3252025

COLDWELL BANKER HUBBARD HANSEN

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $16,309

Year Built

  • Built in 2012

Lot Details

  • 0.29 Acre Lot
  • Northeast Facing Home
  • Fenced
  • Metered Sprinkler System
  • Property is zoned P-D

HOA Fees

  • $433 Monthly HOA Fees

Parking

  • 3 Car Attached Garage

Home Design

  • Brick Exterior Construction
  • Slab Foundation
  • Tile Roof
  • Stucco

Interior Spaces

  • 3,665 Sq Ft Home
  • Open Floorplan
  • Built-In Features
  • Bar Fridge
  • Crown Molding
  • Ceiling Fan
  • Gas Fireplace
  • Double Pane Windows
  • Shutters
  • Sliding Doors
  • Great Room
  • Family Room Off Kitchen
  • Living Room with Fireplace
  • Formal Dining Room
  • Home Office
  • Inside Utility
  • Laundry in unit

Kitchen

  • Eat-In Kitchen
  • Walk-In Pantry
  • Built-In Double Oven
  • Cooktop with Range Hood
  • Microwave
  • Dishwasher
  • Stone Countertops
  • Solid Wood Cabinet
  • Disposal

Flooring

  • Wood
  • Tile

Bedrooms and Bathrooms

  • 5 Bedrooms
  • Primary Bedroom on Main
  • Studio bedroom
  • Walk-In Closet
  • 5 Full Bathrooms
  • Soaking Tub

Pool

  • Heated In Ground Pool
  • Heated Spa
  • In Ground Spa

Outdoor Features

  • Covered Patio or Porch
  • Rain Gutters

Additional Homes

  • Guest House

Schools

  • Windermere Elementary School
  • Bridgewater Middle School
  • Windermere High School

Utilities

  • Central Heating and Cooling System
  • Underground Utilities
  • Natural Gas Connected
  • Tankless Water Heater
  • Cable TV Available

Listing and Financial Details

Community Details

Overview

  • Association fees include 24-Hour Guard, common area taxes, escrow reserves fund, private road
  • Sentry Management Duketta Dolo Association, Phone Number (407) 788-6700
  • Visit Association Website
  • Built by Silliman
  • Waterstone Subdivision
  • The community has rules related to deed restrictions, fencing

Security

  • Gated Community

Home Details

Home Type

Single Family

Est. Annual Taxes

$16,309

Year Built

Built in 2012

Lot Details

0

HOA Fees

$433 per month

Parking

3

Listing Details

  • HOA Fee Includes: Guard - 24 Hour, Common Area Taxes, Escrow Reserves Fund, Private Road
  • Property Type: Residential
  • Property Sub Type: Single Family Residence
  • Construction Materials: Brick, Stucco
  • Fireplace: Yes
  • Living Area: 3665
  • Lot Size Acres: 0.29
  • New Construction: No
  • Year Built: 2012
  • Building Area Total: 5245
  • Lot Size Sq Ft: 12580
  • Directions to Property: From 535, Turn into Waterstone. Give guard name and address.
  • Status: Sold
  • Ownership: Fee Simple
  • Available for Lease YN: 1
  • Escrow State: FL
  • List Office Head Office Key Nume: 159940471
  • Minimum Lease: 7 Months
  • RATIO Current Price By Calculate: 418.83
  • Total Acreage: 1/4 to less than 1/2
  • Unit Number YN: 0
  • Water Access YN: 0
  • MFR_InLawSuiteYN: 1
  • MFR_InLawSuiteDescription: 1 Bathroom,Detached (ADU),Kitchenette,Private Entrance
  • Attribution Contact: 407-234-2256
  • Tax Year: 2024
  • Special Features: VirtualTour

Interior Features

  • Fireplace Features: Gas, Living Room
  • Living Area Units: Square Feet
  • Flooring: Tile, Wood
  • Full Bathrooms: 5
  • Interior Amenities: Built-in Features, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s), Window Treatments
  • Appliances Included: Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Microwave, Range Hood, Tankless Water Heater
  • Foundation Details: Slab
  • Total Bedrooms: 5
  • Levels: One
  • Other Equipment: Irrigation Equipment
  • Spa Features: Heated, In Ground
  • Spa Yn: Yes
  • Window Features: Double Pane Windows, Shutters, Window Treatments
  • Street Number Modifier: 11755
  • Additional Rooms: Den/Library/Office,Family Room,Formal Dining Room Separate,Inside Utility
  • Living Area Meters: 340.49
  • Room Count: 9

Exterior Features

  • Direction Faces: Northeast
  • Other Structures: Guest House
  • Pool Features: Heated, In Ground
  • Exterior Features: Rain Gutters, Sliding Doors, Sprinkler Metered
  • Roof: Tile
  • Pool Private: Yes
  • Waterfront: No
  • Patio and Porch Features: Covered, Rear Porch, Screened
  • Road Surface Type: Paved
  • Water Extras YN: 0
  • Water View YN: 0
  • Waterfront Feet Total: 0
  • Flood Zone Date: 2009-09-25
  • Flood Zone Panel: 12095C0380F

Garage/Parking

  • Attached Garage: Yes
  • Carport Y N: No
  • Garage Spaces: 3
  • Garage Yn: Yes

Utilities

  • Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Underground Utilities, Water Connected
  • Cooling: Central Air
  • Heating: Central
  • Laundry Features: Inside
  • Sewer: Public Sewer
  • Water Source: Public

Condo/Co-op/Association

  • Community Features: Deed Restrictions, Sidewalks
  • Association Amenities: Fence Restrictions, Gated
  • Association Fee: 433.33
  • Association Fee Frequency: Monthly
  • Association Name: Sentry Management - Duketta Dolo
  • Phone: 407-788-6700
  • Association: Yes
  • Senior Community: No
  • Association 2 YN: 0
  • Association Approval Required YN: 0
  • Association Fee Requirement: Required
  • Association Email: ddolo@sentrymgt.com
  • Association URL: orlando.sentrymgt.com

Fee Information

  • Total Annual Fees: 5199.96
  • Total Monthly Fees: 433.33
  • Monthly HOA Amount: 433.33

Schools

  • Elementary School: Windermere Elem
  • High School: Windermere High School
  • Middle Or Junior School: Bridgewater Middle

Lot Info

  • Zoning: P-D
  • Parcel Number: 24-23-27-9009-01-150
  • Additional Parcels: No
  • Fencing: Fenced
  • Lot Features: Sidewalk
  • Flood Zone Code: X
  • Homestead YN: 1
  • Lot Size Square Meters: 1169

Green Features

  • Green Verification Count: 0

Building Info

  • Builder Name: Silliman

Rental Info

  • Pets Allowed: Yes
  • Lease Restrictions YN: 1
  • Additional Lease Restrictions: See HOA docs

Tax Info

  • Tax Annual Amount: 16309
  • Tax Block: 1
  • Tax Book Number: 74/131
  • Tax Lot: 115

Ownership History

Date Name Owned For Owner Type

Purchase Details

Listed on
May 15, 2025
Closed on
Sep 19, 2025
Sold by
Bucher Paul Gerard and Bucher Van Beek
Bought by
Miller Family Revocable Trust and Miller
Seller's Agent
Deb Schroeder
INFINITY REALTY GROUP LLC
Buyer's Agent
Kaley Hansen
COLDWELL BANKER HUBBARD HANSEN
List Price
$1,595,000
Sold Price
$1,535,000
Premium/Discount to List
-$60,000
-3.76%
Views
110

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
22.07%

Purchase Details

Listed on
Feb 18, 2021
Closed on
Apr 22, 2021
Sold by
Bray Robert C and Bray Candice G
Bought by
Bucher Paul Gerard and Bucher Van Beek
Seller's Agent
Deb Schroeder
INFINITY REALTY GROUP LLC
Buyer's Agent
Deb Schroeder
INFINITY REALTY GROUP LLC
List Price
$1,075,000
Sold Price
$1,075,000

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
8.41%
Original Mortgage
$559,000
Interest Rate
3.05%
Mortgage Type
New Conventional

Purchase Details

Listed on
Jul 14, 2018
Closed on
Feb 27, 2019
Sold by
Malley Sharon L O and Malley Michael P O
Bought by
Bray Robert C and Bray Candice G
Seller's Agent
Sharon O'malley
MBA REALTY GROUP, INC
Buyer's Agent
Steve Amburgey
FOLIO REALTY LLC
List Price
$890,000
Sold Price
$815,000
Premium/Discount to List
-$75,000
-8.43%

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
13.74%
Original Mortgage
$600,000
Interest Rate
4.4%
Mortgage Type
New Conventional

Purchase Details

Closed on
Dec 19, 2016
Sold by
Malley Michael P O and Malley Sharon O
Bought by
Malley Sharon L O and Malley Michael P O

Purchase Details

Closed on
Dec 1, 2016
Bought by
Sharon L Omalley Family Trust

Purchase Details

Closed on
Mar 15, 2012
Sold by
Harris Hooker & Huber Llc
Bought by
Omalley Michael P and Omalley Sharon

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$465,300
Interest Rate
3.87%
Mortgage Type
Construction
Source: Public Records

Range of Values:

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Average Value
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List Price
Sold Price
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Purchase History

Date Type Sale Price Title Company
Warranty Deed $1,535,000 Celebration Title Group
Warranty Deed $1,075,000 First American Title Ins Co
Deed $815,000 None Available
Interfamily Deed Transfer -- Attorney
Deed $100 --
Special Warranty Deed $140,000 Attorney
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Previous Owner $559,000 New Conventional
Previous Owner $600,000 New Conventional
Previous Owner $465,300 Construction
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft Prior Sale
09/19/2025 09/19/25 Sold $1,535,000 -3.8% $419 / Sq Ft
08/20/2025 08/20/25 Pending -- -- --
08/01/2025 08/01/25 For Sale $1,595,000 0.0% $435 / Sq Ft
07/04/2025 07/04/25 Pending -- -- --
06/09/2025 06/09/25 For Sale $1,595,000 0.0% $435 / Sq Ft
05/31/2025 05/31/25 Pending -- -- --
05/15/2025 05/15/25 For Sale $1,595,000 +48.4% $435 / Sq Ft
04/22/2021 04/22/21 Sold $1,075,000 0.0% $294 / Sq Ft View Prior Sale
02/23/2021 02/23/21 Pending -- -- --
02/18/2021 02/18/21 For Sale $1,075,000 +31.9% $294 / Sq Ft
02/27/2019 02/27/19 Sold $815,000 -4.1% $222 / Sq Ft View Prior Sale
01/16/2019 01/16/19 Pending -- -- --
12/14/2018 12/14/18 Price Changed $849,990 -1.1% $231 / Sq Ft
12/11/2018 12/11/18 Price Changed $859,400 0.0% $234 / Sq Ft
12/01/2018 12/01/18 Price Changed $859,500 0.0% $234 / Sq Ft
11/24/2018 11/24/18 Price Changed $859,800 0.0% $234 / Sq Ft
10/25/2018 10/25/18 Price Changed $859,900 -2.2% $234 / Sq Ft
09/23/2018 09/23/18 Price Changed $879,000 -0.1% $239 / Sq Ft
08/14/2018 08/14/18 Price Changed $880,000 -1.1% $239 / Sq Ft
07/13/2018 07/13/18 For Sale $890,000 -- $242 / Sq Ft
Source: Stellar MLS

Tax History Compared to Growth

Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $16,610 $1,064,383 -- --
2024 $15,491 $1,064,383 -- --
2023 $15,491 $1,004,258 $0 $0
2022 $15,039 $975,008 $190,000 $785,008
2021 $13,838 $883,257 $190,000 $693,257
2020 $12,325 $775,717 $190,000 $585,717
2019 $12,670 $753,973 $190,000 $563,973
2018 $9,763 $609,838 $0 $0
2017 $9,651 $752,395 $165,000 $587,395
2016 $9,625 $736,123 $165,000 $571,123
2015 $9,794 $687,789 $165,000 $522,789
2014 $9,904 $644,092 $130,000 $514,092
Source: Public Records

Agents Affiliated with this Home

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Map

Source: Stellar MLS

MLS Number: O6308061

Stellar MLS

APN: 24-2327-9009-01-150