Home in 15306 Gilligan Ct Winter Garden for sale with MLS# O6399653
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.
15306 Gilligan Ct, Winter Garden, FL 34787
- Price:
- $925,000.00
- Original List Price:
- $925,000.00
- List Price per Sq Ft (Calculated, Approx.):
- $295.81
- Listing Type:
- For Sale
- Status:
- Active
- Listing Category:
- Residential
- Property Type:
- Single Family House
- MLS Number:
- O6399653
- Bedrooms:
- 4
- Bathrooms Total:
- 4
- Full Bath:
- 3
- Half Bath:
- 1
- Additional Rooms:
- Den/library/office, Loft
- Living Area:
- 3,127 Sqft
- Built-Up Area:
- 4,208 Sqft
- Lot Area:
- 6,912 Sqft
- Building Area Source:
- Public Records
- Living Area Source:
- Public Records
- Lot Features:
- Cul-De-Sac, Paved, Sidewalk, Street Dead-end
- Lot Size Acres:
- 0.16
- View from the Property:
- Water
- Waterfront:
- Yes
- Waterfront Features:
- Pond
- Private Pool
- Swimming Pool Features:
- In Ground, Salt Water, Screen Enclosure, Child Safety Fence
- Security:
- Smoke Detector(s), Security System, Security System Owned
- Furnished:
- Unfurnished
- Appliances:
- Dishwasher, Disposal, Microwave, Refrigerator, Built-in Oven, Electric Water Heater, Range Hood
- Interior:
- Eat-in Kitchen, High Ceilings, Walk-In Closet(s), Ceiling Fans(s), Open Floorplan, Window Treatments, Solid Surface Counters, Solid Wood Cabinets, Primary Bedroom Main Floor
- Exterior:
- Outdoor Grill, Sidewalk, Sliding Doors, Rain Gutters, Sprinkler Metered
- Patio and Porch:
- Screened, Front Porch, Rear Porch
- Laundry:
- Washer Hookup, Inside, Laundry Room, Electric Dryer Hookup
- Fireplace
- Fireplace:
- Electric
- Air Conditioning System:
- Central Air
- Heating System:
- Central
- Fence:
- Fenced
- Vegetation and Trees:
- Trees/landscaped, Mature Landscaping
- Property Entrance Faces:
- North
- Other Equipment:
- Irrigation Equipment
- Water View
- Water View Details:
- Pond
- Year Built:
- 2020
- Roof:
- Shingle
- Architectural Style:
- Florida
- Levels:
- Two
- Construction Materials:
- Block, Stucco
- Flooring:
- Carpet, Tile
- Number of stories:
- 2
- Foundation Details:
- Slab
- Flood Zone Code:
- X
- Homestead Property
- Tax Annual Amount:
- $8,308.00
- Tax Year:
- 2025
- Association Fee:
- $102.00
- Association Fee Frequency:
- Monthly
- Total Annual Fees:
- $1,224.00
- Total Monthly Fees:
- $102.00
- Garage
- Garage Spaces:
- 2
- Attached Garage
- Sewer:
- Public Sewer
- Utilities Available:
- Electricity Connected, Cable Connected
- Water Source:
- Public
- Association
- Minimum Lease Term:
- 8-12 Months
- Pets Allowed?
- Amenities Provided by the Homeowner's Association (HOA):
- Pool
- Subdivision Name:
- WINDING BAY PH 1B
- Community Features:
- Park, Pool, Playground, Dog Park, Association Recreation - Owned, Deed Restrictions, Community Mailbox
- Association Fee Includes:
- Pool, Recreational Facilities
- Senior Community:
- No
- Association Fee Required:
- Required
- Association Management:
- Mariluz Onna - FS Residential
- Association Phone:
- 407-653-8134
- Occupant Type:
- Owner
- Lease Considered:
- Yes
- Tax Legal Description:
- WINDING BAY PHASE 1B 100/146 LOT 114
- Real Estate Folio Number (Parcel Number):
- 20-24-27-7826-01-140
- Zoning:
- P-D
- Title to the property is held by owner as:
- Fee Simple
- Elementary School:
- Water Spring Elementary
- High School:
- Horizon High School
- Middle Or Junior School:
- Water Spring Middle
- Originally published on:
- April 17, 2026 5:23 pm
- Active on the market since:
- April 17, 2026
- Listing Agreement executed on:
- April 17, 2026
- Listing Status Last Changed On:
- April 17, 2026 5:23 pm
- Photos updated on:
- April 17, 2026 5:26 pm
- Last Modified:
- April 17, 2026 5:40 pm
- Courtesy of:
- REAL ESTATE HOUSE FL INC
- Attribution:
- 407-484-0005
- Road Surface Type:
- Asphalt
- Street Name:
- GILLIGAN
- Street Number:
- 15306
- City:
- WINTER GARDEN
- State:
- Florida
- Zip Code:
- 34787
- County:
- Orange
- Latitude:
- N28° 23' 20.3''
- Longitude:
- W82° 22' 4.3''
Neighborhood Stats
Source: U.S. Census Bureau, ACS 5-Year Estimates
Air Quality
Source: AirNow.gov · Lake County
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