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$874,500 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 3,672 Sq. Ft.
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Under contract-accepting backup offers. BEST VALUE IN WINTER GARDEN! Welcome home to this CORNER LOT, private POOL HOME in the active and welcoming WINDING BAY neighborhood of Winter Garden. This home has more than $150,000 in UPGRADES! Your first floor includes a dedicated OVERSIZED office, a SEPARATE guest room with ensuite - PERFECT for MULTI GENERATIONAL living. Continue to your kitchen and be greeted by an oversized open floor plan with a family room that exudes natural light with a view of your private FULLY FENCED outdoor living space. Kitchen is UPGRADED with double wall ovens, newer appliances, 42" cabinets, quartz countertops, and modern backsplash. Upstairs you will find your primary suite, an ADDITIONAL living room loft space, and three bedrooms - one of which has its own ensuite. Double sinks in the fourth bathroom makes getting ready easy for larger families. The backyard OASIS functions as a massive, additional living space and is a magazine worthy gathering place. When you're ready to unwind enjoy your HEATED saltwater pool and HUGE, custom HOT TUB. If that's not enough, enjoy endless hours of outdoor fun with your own POOL SLIDE for your family. The pool bath and Mansford cage guarantee convenience and bug-free relaxation all year round. The upgrades don't end there- the backyard is pre-plumbed for your dream outdoor kitchen. You also have a whole house water treatment/softener system AND upgraded lighting features throughout the home. Winding Bay is situated in a GRADE A school district with a community pool, four playgrounds, nature trail, and two dog parks. You are right off the 429 and less than 15 minutes from Disney. Orlando International airport, Universal and numerous other amusement parks are less than 30 minutes away. Brand new hospital close by as well. WELCOME HOME!

Full Property Details for 15378 Gilligan Ct

General

  • Price: $874,500
  • HOA FEE: $105/month
  • Taxes: $9,354 (2024)
  • Status: Pending
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6355206
  • Updated: 12/29/2025
  • Added to Site: 87 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 4
  • Interior Features: Attic Fan, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Tray Ceiling(s)
  • Appliances: Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range Hood, Refrigerator, Washer, Water Filtration System
  • Flooring: Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Heated, In Ground

Exterior

  • Exterior Features: Irrigation System, Lighting

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: WINDING BAY PH 1B
  • Driving Directions: Take 429 South to Avalon Rd. Make left onto Micelli Dr. Right onto Petrillo Way Right onto Gilligan Ct
  • Direction Faces: North

School Information

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

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Association: Yes
  • Assoc. Name: First Service Residential
  • Pet Restrictions: Please contact HOA for pet restrictions. Buyer responsibility

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable Connected, Electricity Connected, Underground Utilities

Structural Information

  • Exterior Const.: Stucco
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 3,672
  • Sq. Ft. Source: Public Records
  • Year Built: 2021

Lot Features

  • Lot Size (Acres): 0.18
  • Lot Size (Sq. Ft.): 7,775
  • Lot Size: 7775
  • Street/Road Desc.: Paved

Financial Considerations

  • Association Fee: $105
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $9,354
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINDING BAY PHASE 1B REPLAT 103/1 LOT 101A
  • Flood Zone Info: X
  • APN: 202427782801011
  • Property ID: 202427782801011
  • Block/Lot/Section: 1

Listed by Lokation

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— 15378 Gilligan Ct —

  • Lokation

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 15378 Gilligan Ct

School District:Orange County School District
NameGradesDistance
Water Spring Elementary
16000 Water Spring Boulevard, Winter Garden, FL 34787
PK-51.3 mi
Water Spring Middle School-0482
10393 Seidel Road, Winter Garden, FL 34787
6-82.2 mi
Horizon High School
10393 Seidel Road, Winter Garden, FL 34787
9-122.2 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 15378 Gilligan Ct Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/11/2025
Price Reduced
$874,500
-2.82%
MLS
11/03/2025
Price Reduced
$899,900
-2.7%
MLS
10/24/2025
Listed
$924,900
71.85%
MLS
7/30/2021
Sold
$538,202
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 15378 Gilligan Ct

Year
Property Taxes
Change
Tax Assessment
Change
2024
$9,354
—
$602,592
3%
2024
$9,354
18%
$585,609
13%
2023
$7,936
341%
$517,096
508%
2021
$1,800
-77%
$85,000
-83%
2022
$7,665
326%
$502,035
813%
2021
$1,800
—
$55,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Lokation

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15378 Gilligan Court, Winter Garden, FL 34787 (MLS# O6355206) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 15378 Gilligan Court is currently listed for $874,500 and was received on October 24, 2025. Want to learn more about 15378 Gilligan Court? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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