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$925,000
10 Days On Site

15306 GILLIGAN COURT
WINTER GARDEN, FL 34787

For Sale|Single Family Residence|Pending
4
Beds
4
Total Baths
3
Full Baths
1
Partial Bath
3,127
SqFt
$296
/SqFt
2020
Built
Subdivision:
WINDING BAY PH 1B
County:
Orange
Call Now: 321-804-3112
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321-804-3112
15306 GILLIGAN COURT15306 GILLIGAN COURT15306 GILLIGAN COURT15306 GILLIGAN COURT
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Monthly Payment (Est.)

$4,220
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

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.

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Listing Snapshot
Price 
$925,000
Days On Site 
10 Days
Bedrooms 
4
Inside Area (SqFt) 
3,127 sqft
Total Baths 
4
Full Baths 
3
Partial Baths 
1
Lot Size 
0.16 Acres
Year Built 
2020
MLS® Number 
O6399653
Status 
Pending
Property Tax 
$8,308
HOA/Condo/Coop Fees 
$102 monthly
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
5 days agoListing updated with changes from the MLS®
5 days agoStatus changed to Pending
2 weeks agoListing first seen on site
General Features
Acres 
0.16
Attached Garage 
Yes
Direction Faces 
North
Foundation 
Slab
Garage 
Yes
Garage Spaces 
2
Levels 
Two
Number Of Stories 
2
Parking 
Attached
Pets 
Yes
Property Sub Type 
Single Family Residence
Security 
Security SystemSecurity System OwnedSmoke Detector(s)
Sewer 
Public Sewer
SqFt Total 
4208
Style 
Florida
Utilities 
Cable AvailableCable ConnectedElectricity Connected
Water Source 
Public
Zoning 
P-D
Interior Features
Appliances 
DishwasherDisposalElectric Water HeaterMicrowaveRange HoodRefrigerator
Cooling 
Central Air
Fireplace 
Yes
Fireplace Features 
Electric
Flooring 
CarpetTile
Furnished 
Unfurnished
Heating 
Central
Interior 
Eat-in KitchenHigh CeilingsOpen FloorplanWalk-In Closet(s)
Laundry Features 
Electric Dryer HookupInsideLaundry RoomWasher Hookup
Bathroom 2 
Dimensions - 11.61x5.3Level - FirstFeatures - Double Vanity, Stone Counters
Bathroom 3 
Dimensions - 5x5.2Level - First
Bathroom 4 
Dimensions - 8.1x5.4Level - Second
Bedroom 2 
Dimensions - 10.4x13.5Level - FirstFeatures - Ceiling Fan(s)
Bedroom 3 
Dimensions - 10.4x13.6Level - FirstFeatures - Ceiling Fan(s)
Bedroom 4 
Dimensions - 10.1x12.9Level - SecondFeatures - Ceiling Fan(s)
Den 
Level - FirstFeatures - Ceiling Fan(s)
Dining Room 
Dimensions - 10.8x12.11Level - First
Kitchen 
Dimensions - 29.5x12.9Level - FirstFeatures - Breakfast Bar, Granite Counters, Kitchen Island, Pantry
Laundry 
Dimensions - 6.3x11.6Level - First
Living Room 
Dimensions - 16.8x16.11Level - FirstFeatures - Ceiling Fan(s)
Loft 
Dimensions - 19.4x15.11Level - SecondFeatures - Ceiling Fan(s)
Master Bathroom 
Dimensions - 9.2x8.4Level - FirstFeatures - Double Vanity, Stone Counters
Master Bedroom 
Dimensions - 16.3x17.1Level - FirstFeatures - Ceiling Fan(s)
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Exterior Features
Construction Details 
BlockStucco
Exterior 
Outdoor GrillRain Gutters
Fencing 
Fenced
Lot Features 
Cul-De-SacPavedWaterfront
Patio And Porch 
Front PorchRear PorchScreened
Pool Features 
In GroundSalt WaterScreen EnclosurePrivate
Private Pool 
Yes
Roof 
Shingle
View 
PondWater
Waterfront 
Yes
Waterfront Features 
Pond
Waterview 
PondWater
Community Features
Association Amenities 
Pool
Association Dues 
102
Community Features 
ParkPlaygroundPool
HOA Fee Frequency 
Monthly
MLS Area 
34787 - Winter Garden/Oakland
Roads 
Asphalt
Township 
24
Schools
School District
Unknown
Elementary School
Water Spring Elementary
Middle School
Water Spring Middle
High School
Horizon High School
Listing courtesy of REAL ESTATE HOUSE FL INC (407) 484-0005



Listing information is provided by Participants of the Stellar MLS. 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. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-04-28 11:32 AM EDT

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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