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15306 GILLIGAN COURT
WINTER GARDEN, FL, 34787
$925,000
4 Beds
3.5 Baths
3,127 SqFt
0.16 Acres
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MLS #O6399653 image #0
Set within one of Winter Garden’s most sought-after communities, this thoughtfully designed two-story home offers a lifestyle defined by ease, connection, and everyday enjoyment. This 4-bedroom, 3.5-bath home with over 3,000 square feet features an open floor plan with a gourmet kitchen and a large island, perfect for both everyday living and entertaining. The main level includes a dedicated den/office, while the second floor offers a spacious loft, along with a fourth bedroom and full bath—ideal for guests or multi-generational living. Tree-lined sidewalks, friendly neighbors, nearby parks, and resort-style amenities create a setting that feels both relaxed and vibrant, while top-rated schools, convenient access to shopping and dining, and close proximity to Walt Disney World Resort. Positioned on arguably one of the BEST lots in the community, this home sits at the end of a quiet cul-de-sac with breathtaking, unobstructed pond and tree-lined views that create a peaceful and private backdrop. Inside, the home showcases extensive upgrades and thoughtful design throughout, including a kitchen with 42-inch cabinetry and additional custom upper cabinets, GE Profile appliances, and a seamless flow into the main living space highlighted by two expansive tri-sliders opening to the outdoor oasis. Custom floor-to-ceiling drapery adds elegance, while upgrades such as 8-foot doors throughout, level 4 wood-look tile flooring, upgraded carpet with 8-pound padding, 5 1/4-inch baseboards, and 7 1/4-inch shiplap accents in the hallway, kitchen, tech nook, and primary bedroom elevate the interior. Additional features include custom plantation shutters on the first floor, upgraded glass doors in the front den/office, Cat 6 wiring throughout with pre-wiring for PoE security cameras, and a new alarm system with wireless sensors on all doors and windows. The home has been meticulously maintained with quarterly HVAC servicing, gutters installed since purchase, and a freshly painted exterior completed in 2025 using upgraded Sherwin Williams 25-year paint. Step outside to a private outdoor retreat featuring fresh landscaping, a fully fenced side yard, a privacy-enhancing podocarpus hedge, and custom paver walkways with additional space for storage. The backyard feels like a private Central Florida escape, where an 18,000-gallon resort-style saltwater pool serves as the true centerpiece, complete with a lounging platform overlooking the serene pond and tree-lined backdrop. The pool is thoughtfully designed with sealed pavers, a striking midnight blue interior finish, a fountain with dual deck jets, two multicolor LED lights, and a Pentair smart system for remote control, all professionally serviced weekly. The screened enclosure allows for year-round enjoyment, while the community dog park directly across the street adds everyday convenience for pet lovers. From the upstairs loft and bedrooms, enjoy views of Disney fireworks, adding a magical touch to everyday living. This move-in ready home is prepared for its next chapter, with community amenities that include a resort-style pool, oversized cabana, sports fields, playground, sidewalks, and a dog park. More than just beautifully upgraded, this home offers a rare opportunity to own a meticulously maintained, design-forward property in a premier location, delivering both luxury and lifestyle in one exceptional package—a place to settle in, build memories, and truly feel at home in Winter Garden.

Property Details

Price:
$925,000
MLS #:
O6399653
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDING BAY PH 1B
Neighborhood:
34787wintergardenoakland
Listed Date:
Apr 17, 2026
Finished Sq Ft:
3,127
Total Sq Ft:
4,208
Lot Size:
6,912 sqft / 0.16 acres (approx)
Year Built:
2020
FloridaWaterfrontPoolPrimary Bedroom Main Floor34787 – Winter Garden/oakland34787wintergardenoaklandWinding Bay Ph 1bWater Spring ElementaryWater Spring MiddleHorizon High SchoolWater8-12 MonthsPets Allowed

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Schools

Elementary School:
Water Spring Elementary
Middle School:
Water Spring Middle
High School:
Horizon High School

Interior

Appliances
Built-In Oven, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Tile
Heating
Central
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Walk-In Closet(s), Window Treatments
Laundry Features
Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
Levels
Two

Exterior

Architectural Style
Florida
Association Amenities
Pool
Attached Garage YN
1
Community Features
Association Recreation – Owned, Community Mailbox, Deed Restrictions, Dog Park, Park, Playground, Pool
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
North
Exterior Features
Irrigation System, Outdoor Grill, Rain Gutters, Sidewalk, Sliding Doors, Sprinkler Metered
Fencing
Fenced
Garage Spaces
2
Lot Features
Cul-De-Sac, Sidewalk, Street Dead-End
Patio And Porch Features
Front Porch, Rear Porch, Screened
Roof
Shingle
Security Features
Security System, Security System Owned, Smoke Detector(s)
View
Water
Waterfront Features
Pond

Financial

HOA Fee
$102
HOA Fee Frequency
Monthly
HOA Includes
Community Pool, Pool Maintenance, Recreational Facilities
HOA Name
Mariluz Onna – FS Residential
HOA Phone
407-653-8134
Tax Year
2025
Taxes
$8,308

Map

Community

Subdivisions in WINTER GARDEN

Market Summary

Current real estate data for Single Family in WINTER GARDEN as of Apr 23, 2026
779
Single Family Listed
109
Avg DOM
282
Avg $ / SqFt
$749,092
Avg List Price

Property Summary

    Located in the WINDING BAY PH 1B subdivision, 15306 GILLIGAN COURT WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $925,000 and features 4 beds, 4 baths, and has approximately 3,127 square feet of living space, and was originally constructed in 2020. The current price per square foot is $296. The average price per square foot for Single Family listings in WINTER GARDEN is $282. The average listing price for Single Family in WINTER GARDEN is $749,092. To schedule a showing of MLS#o6399653 at 15306 GILLIGAN COURT in WINTER GARDEN, FL, contact your Preferred Real Estate Brokers agent at 4076987254.

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15306 GILLIGAN COURT
WINTER GARDEN, FL