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.
- Built in 2000
- 3 garage spaces
- $299.90/sqft
- Lot size: 18,602 sqft
- 28 days on market
- Directions: Heading South on FL-429, take exit 24 for Plant Street. Turn right onto Plant St. Turn right onto N Dillard Street. Turn right onto Courtlea Oaks Blvd. Home is on the right.
- County: Orange
- Geo subdivision: COURTLEA OAKS
Nearby Schools
Tildenville Elem
Lakeview Middle
West Orange High
Features
Interior
Exterior
Utilities
Structure
Pets, Accessibility & Amenities
Community Info
Financial
Lease Information
Tax, Legal & Financing
Let's get in touch!
Let's get in touch!

Gabriella Massaro
Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990
- Source: Stellar MLS
- MLS #: O6385964
Listing updated: April 3, 2026 at 3:09AM
Listing provided by: Jennifer Coon, LAKESIDE REALTY WINDERMERE INC
Last checked 19 hours ago
Listing provided by: Jennifer Coon, LAKESIDE REALTY WINDERMERE INC
Last checked 19 hours ago
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. Some IDX listings have been excluded from this website.







