

441 Courtlea Oaks BoulevardWinter Garden, FL, 34787
- Price per sqft
- $290
- Sold on
- Jun 15, 2026
About this property
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.

Property details
- Property type
- Single Family Residence
- Street address
- 441 Courtlea Oaks Boulevard
- City
- Winter Garden
- State
- FL
- ZIP code
- 34787
- Year built
- 2000
- New construction
- No
- Faces
- Northwest
- Rooms
- 3
- Living area
- 4,001 sqft
- Total building area
- 4,870 sqft
- Levels
- Two
Price & sale history
| Date | Event | Price | Change from previous recorded asking price |
|---|---|---|---|
| SoldMLS #O6385964 | $1,160,000 | Not applicable | |
| Price reducedMLS #O6385964 | $1,199,900Change: −12.7%−$175,100 | −12.7%−$175,100 | |
| Listed for saleMLS #O6385964 | $1,375,000 | Not applicable |
Location
Recent sales nearby






















