$1,375,000

441 COURTLEA OAKS BOULEVARD, Winter Garden, FL 34787

5 beds |
5 baths |
4,089 sqft

Single-Family Home
Built in 2000
0.43acre lot
3 car garage
$336/sqft
Listed 6 days ago

Property Description

One or more photo(s) has been virtually staged. One of the largest homes in the highly desirable Courtlea Oaks community, this spacious 5-bedroom, 4.5-bath pool home offers over 4,000 square feet of living space and an exceptional opportunity in the heart of Winter Garden’s golf cart district. The flexible floor plan includes a rare apartment above the garage connected to the main home, providing ideal space for guests, extended family, a private office, or additional living quarters. Important updates have already been completed by these original to the home owners, including a new roof and A/C systems installed just two years ago, offering peace of mind for the next owner. Step outside to enjoy a beautiful pool and a private setting backing to the West Orange Trail, perfect for biking, walking, and outdoor recreation right from your backyard. Located just minutes from historic downtown Winter Garden, residents enjoy boutique shopping, dining, breweries, and the award-winning Saturday Farmers Market, along with numerous festivals and community events throughout the year. With its generous square footage, versatile layout, and unbeatable location, homes like this rarely come available in Courtlea Oaks.

Listing Status:: Active
Date Added:: March 5, 2026
Data Last Updated:: March 12, 2026 at 4:23AM
Listing Office:: LAKESIDE REALTY WINDERMERE INC : 407-876-5575
Listing Agent:: Jennifer Coon : 321-948-8056
MLS ID:: O6385964

General: Ceiling Fans(s)Crown MoldingHigh CeilingsOpen FloorplanSolid Surface CountersSolid Wood CabinetsThermostatWalk-In Closet(s)
Appliances: Built-In OvenCooktopDishwasherRefrigerator
Laundry: InsideLaundry Room
Flooring: CarpetTileWood
A/C: Central Air
Heating: CentralElectric
Fireplace: Family RoomFireplace

General: French DoorsOutdoor ShowerRain GuttersSidewalkIn Ground
Pool: GuniteIn GroundLighting
Parking: Driveway

Roofing: Shingle
General: BlockConcreteStuccoFrameTwoSlab

Road/Access: Asphalt
HOA Amenities: 500.0Semi-Annually
Originating MLS: Stellar MLS
County: Orange

Zoning: R-1COURTLEA OAKS PHASE 2B 41/67 LOT 2614-22-27-1944-00-260
Fencing: Vinyl

Utilities: Cable AvailableElectricity ConnectedPublicWater Connected
Water: Public
Sewer: Public Sewer

Source: Stellar MLS
Ownership: Fee Simple

This listing courtesy of Jennifer Coon , LAKESIDE REALTY WINDERMERE INC

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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Location

Schools Nearby

Dillard Street Elementary School

311 N Dillard St, Winter Garden, FL, 34787

Grades PK-5

0.49 miles away

Lakeview Middle School

1200 W Bay St, Winter Garden, FL, 34787

Grades 6-8

1.75 miles away

West Orange High School

1625 Beulah Rd, Winter Garden, FL, 34787

Grades 9-12

2.06 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.