11755 WATERSTONE LOOP DRIVE, Windermere, FL 34786
OFF MARKET

11755 WATERSTONE LOOP DRIVE
Windermere, FL 34786

  • 5 Beds
  • 5 Baths
  • 3,665 sqft (on 0.29 acres)

$1,530,400

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $10,513/mo*
Refinance Your Home

$1,530,400

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $10,513/mo*
Refinance Your Home
5 Beds
5 Baths
3,665 sqft
(on 0.29 acres)

Home Value

Trulia Estimate
$1.53M
Since last month
Decreased$9K (-0.6%)
Since last year
Increased$5K (+0.3%)
Since last sale
Decreased$6K (-0.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +60% in the last 10 years
MonthEstimated value
2026
August 2026$1.53M
July 2026$1.54M
June 2026$1.55M
May 2026$1.53M
April 2026$1.52M
March 2026$1.51M
February 2026$1.52M
January 2026$1.52M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
11821 WATERSTONE LOOP DRIVE, Windermere, FL
0.07
Single-Family Home
$1,500,000
04/29/26
4
4.5
3,447
11802 WATERSTONE LOOP DRIVE, Windermere, FL
0.04
Single-Family Home
$1,350,000
04/17/26
4
4.5
3,396
6222 LECCO WAY, Windermere, FL
0.08
Single-Family Home
$1,550,000
02/06/26
5
3.5
3,967
11706 WATERSTONE LOOP DRIVE, Windermere, FL
0.05
Single-Family Home
$1,370,000
11/04/25
4
3.5
3,586
11754 WATERSTONE LOOP DRIVE, Windermere, FL
0.04
Single-Family Home
$1,300,000
10/03/25
4
3
3,049
5061 SAWYER COVE WAY, Windermere, FL
0.40
Single-Family Home
$2,350,000
08/04/26
5
4.5
3,888
5067 SAWYER COVE WAY, Windermere, FL
0.39
Single-Family Home
$2,100,000
08/14/26
5
4
3,567
6564 LAGOON STREET, Windermere, FL
0.32
Single-Family Home
$1,830,000
03/06/26
5
4.5
3,685
6106 MARLEON DRIVE, Windermere, FL
0.44
Single-Family Home
$2,000,000
08/25/25
4
5
3,966

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
11754 WATERSTONE LOOP DRIVE, Windermere, FL 34786
0.04
$1,297,500
4
3
3,049
Off Market
11748 WATERSTONE LOOP DRIVE, Windermere, FL 34786
0.04
$1,332,800
5
4
3,235
Off Market
11802 WATERSTONE LOOP DRIVE, Windermere, FL 34786
0.04
$1,350,000
4
4.5
3,396
Recently Sold
11706 WATERSTONE LOOP DRIVE, Windermere, FL 34786
0.05
$1,370,000
4
3.5
3,586
Recently Sold
11821 WATERSTONE LOOP DRIVE, Windermere, FL 34786
0.07
$1,500,000
4
4.5
3,447
Recently Sold
6222 LECCO WAY, Windermere, FL 34786
0.08
$1,550,000
5
3.5
3,967
Recently Sold
6228 LECCO WAY, Windermere, FL 34786
0.09
$1,252,800
4
3
2,755
Off Market
12706 S LAKE SAWYER LN, Windermere, FL 34786
0.19
$1,391,300
5
5
3,894
Off Market
6518 SAWYER SHORES LANE LOT 2, Windermere, FL 34786
0.18
$725,000
-
-
-
Recently Sold
12012 WATERSTONE LOOP DRIVE, Windermere, FL 34786
0.15
$2,098,600
5
5.5
4,715
Off Market
11628 WATERSTONE LOOP DR DRIVE, Windermere, FL 34786
0.20
$2,587,400
5
6
5,161
Off Market

Local Information

  • Map ViewExplore the area around 11755 WATERSTONE LOOP DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2012
Lot Size
0.29 acres
Living Area
3,665 sqft
Price/Sqft
$418
Parking
3 Car Garage
HOA
$433/Monthly

About this House

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.
11755 WATERSTONE LOOP DRIVE, Windermere, FL 34786 is a 5 bedroom, 5 bathroom, 3,665 sqft single-family home built in 2012. It last sold for $1,535,000 on Sep 19, 2025 (4% below the $1,595,000 asking price). It is currently off market. The Trulia Estimate is $1,530,400, with a rent estimate of $6,633/month.
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

Home Details for 11755 WATERSTONE LOOP DRIVE

Interior Features

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

Exterior Features

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

Days on Market

Cumulative Days on Market: 60

Property Information

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

Price & Status

Price
List Price: $1,595,000
Status Change & Dates
Off Market Date: Wed Aug 20 2025

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINDERMERECommunity: WATERSTONE
School Information
Elementary School: Windermere ElemJr High / Middle School: Bridgewater MiddleHigh School: Windermere High School

Building

Building Details
Builder Name: Silliman
Building Area
Building Area: 5245 Square Feet

Community

Community Features: Deed Restrictions, SidewalksNot Senior Community

HOA

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

Lot Information

Lot Area: 0.29 acres

Listing Info

Special Conditions: None

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6308061Back On Market Date: Fri Aug 01 2025Showing Requirements: ShowingTimeUniversal Property Id: US-12095-N-242327900901150-R-N

Additional Information

HOA Amenities: Fence Restrictions,Gated

Price and Tax history

DateEventPrice
Sep 19, 2025
Source: Stellar MLS #O6308061
Sold
$1,535,000
Aug 21, 2025
Source: Stellar MLS #O6308061
Pending
$1,595,000
Aug 1, 2025
Source: Stellar MLS #O6308061
PendingToActive
$1,595,000
Jul 7, 2025
Source: Stellar MLS #O6308061
Pending
$1,595,000
Jun 9, 2025
Source: Stellar MLS #O6308061
PendingToActive
$1,595,000

Market trends in Windermere

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$814K
$92.5KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$292
$18MoM
Available listings
296
11MoM

Around this home

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 271 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

  • 80 % 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
    Flag
  • 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
    Flag
  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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

Frequently asked questions about 11755 WATERSTONE LOOP DRIVE

  • What is 11755 WATERSTONE LOOP DRIVE estimated to be worth?
    Trulia's estimated value for 11755 WATERSTONE LOOP DRIVE in Windermere, FL is $1,530,400.
  • What is the price history for 11755 WATERSTONE LOOP DRIVE?
    11755 WATERSTONE LOOP DRIVE in Windermere, FL last sold for $1,535,000 in September 2025.
  • Is Windermere a buyer's or seller's market?
    Windermere is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Windermere?
    The median sale price in Windermere is $814K. That is up $92.5K from the prior month.
  • Does 11755 WATERSTONE LOOP DRIVE have air conditioning?
    Yes, 11755 WATERSTONE LOOP DRIVE in Windermere, FL has air conditioning.
  • Does 11755 WATERSTONE LOOP DRIVE have a pool?
    Yes, 11755 WATERSTONE LOOP DRIVE in Windermere, FL has a pool.

Explore by feature - Pet Friendly

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