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.
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.
Property Details
Price:
$1,595,000
MLS #:
O6308061
Status:
Active
Beds:
5
Baths:
5
Address:
11755 WATERSTONE LOOP DRIVE
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WATERSTONE A D E F G H J L
Neighborhood:
34786 – Windermere
City:
WINDERMERE
Listed Date:
May 15, 2025
State:
FL
Finished Sq Ft:
5,245
Total Sq Ft:
5,245
ZIP:
34786
Lot Size:
12,580 sqft / 0.29 acres (approx)
Year Built:
2012
Schools
Elementary School:
Windermere Elem
Middle School:
Bridgewater Middle
High School:
Windermere High School
Interior
Appliances
Bar Fridge, Built- In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range Hood, Tankless Water Heater, Washer
Bathrooms
5 Full Bathrooms
Cooling
Central Air
Flooring
Tile, Hardwood
Heating
Central
Laundry Features
Inside
Exterior
Association Amenities
Fence Restrictions, Gated
Community Features
Deed Restrictions, Sidewalks
Construction Materials
Brick, Stucco
Exterior Features
Irrigation System, Rain Gutters, Sliding Doors, Sprinkler Metered
Other Structures
Guest House
Roof
Tile
Financial
HOA Fee
$433
HOA Frequency
Monthly
HOA Includes
24-Hour Guard, Common Area Taxes, Escrow Reserves Fund, Private Road
HOA Name
Sentry Management – Duketta Dolo
Tax Year
2024
Taxes
$16,309
Map
Community
- Address11755 WATERSTONE LOOP DRIVE WINDERMERE FL
- SubdivisionWATERSTONE A D E F G H J L
- CityWINDERMERE
- CountyOrange
- Zip Code34786
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11755 WATERSTONE LOOP DRIVE
WINDERMERE, FL
LIGHTBOX-IMAGES