$925,000

15306 Gilligan Court Winter Garden, FL 34787 Residential - Single Family Active

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Description

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 Highlights

Property Type: Residential - Single Family
Cooling: Central Air
Fenced: Yes
Garage: 2 car attached
Heating: Central
Home Style: Florida
Lot Size: 0.16 Acres
Roof Type: Shingle
Stories: 2.0
Taxes: $8,308
Year Built: 2020

General Information

Bedrooms: 4
Bathrooms: 3 Full 1 Half
Sqft: 3,127
County: Orange
High School: Horizon High School
Subdivision: WINDING BAY
Listed By:
Gretchen Carlson REAL ESTATE HOUSE FL INC 407-484-0005

Amenities

Ceiling Fans(s)
Eat-in Kitchen
High Ceilings
Open Floorplan
Primary Bedroom Main Floor
Solid Surface Counters
Solid Wood Cabinets
Walk-In Closet(s)
Window Treatments
Outdoor Grill
Rain Gutters
Sidewalk
Sliding Doors
Sprinkler Metered

Room Information

Living Room: 16.8x16.11
Dining Room: 10.8x12.11
Kitchen: 29.5x12.9
Primary Bedroom: 16.3x17.1
Primary Bathroom: 9.2x8.4
Bedroom 2: 10.4x13.5
Bathroom 2: 11.61x5.3
Bedroom 3: 10.4x13.6
Bathroom 3: 5x5.2
Laundry: 6.3x11.6
Bedroom 4: 10.1x12.9
Bathroom 4: 8.1x5.4
Loft: 19.4x15.11

Property Features

Additional Rooms: Den/Library/Office, Loft
Appliances: Built-In Oven, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
Association Amenities: Pool
Community Features: Association Recreation - Owned, Community Mailbox, Deed Restrictions, Dog Park, Park, Playground, Pool
Directions: Community is located on the left while traveling south on Avalon Rd. 2/3 mile south of Flamingo Crossings Blvd. intersection where Avalon Rd begins to curve right (to the west).
Exterior: Block, Stucco
Fencing: Fenced
Fireplace: Electric
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Carpet, Tile
Foundation: Slab
Frontage Pond: 1000
HOA Fee: 102/ Monthly
HOA Y/N: Yes
Home Warranty Y/N: No
Lot: Cul-De-Sac, Sidewalk, Street Dead-End, Paved
Lot Dimensions: 0.16
Other Equipment: Irrigation Equipment
Ownership: Fee Simple
Patio/Porch: Front Porch, Rear Porch, Screened
Pets Allowed: Yes
Pool: Child Safety Fence, In Ground, Salt Water, Screen Enclosure
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Security: Security System, Security System Owned, Smoke Detector(s)
Sewer: Public Sewer
Showing Instructions: ShowingTime
Special Sale Provisions: None
Swimming Pool: Yes
Utilities: Cable Connected, Electricity Connected
Vegetation: Mature Landscaping, Trees/Landscaped
Water: Public
Water Access Y/N: No
Waterfront Features: Pond
Water View: Pond
Zoning: P-D
$925,000
4beds
3.5baths
3,127sqft
2cars
New to the Market Active
BEDS4 BATHS3 full 1 partial SQUARE FEET3,127 MLS#O6399653
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONWINDING BAY

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15306 Gilligan Court , Winter Garden, FL 34787.

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Estimated Payment

$ 4,081.99 per month $3,119.87 Principal & Interest $692.33 Property Tax $269.79 Homeowner's Insurance

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