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$1,375,000
New Listing

441 COURTLEA OAKS BOULEVARD
WINTER GARDEN, FL 34787

For Sale|Single Family Residence|Active
5
Beds
5
Total Baths
4
Full Baths
1
Partial Bath
4,089
SqFt
$336
/SqFt
2000
Built
Subdivision:
COURTLEA OAKS
County:
Orange
Call Now: +1 (407) 456-4820
Is this the listing for you? We can help make it yours.
+1 (407) 456-4820
441 COURTLEA OAKS BOULEVARD441 COURTLEA OAKS BOULEVARD441 COURTLEA OAKS BOULEVARD441 COURTLEA OAKS BOULEVARD
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Monthly Payment (Est.)

$6,273
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

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.

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Listing Snapshot
Price 
$1,375,000
Days On Site 
0 Days
Bedrooms 
5
Inside Area (SqFt) 
4,089 sqft
Total Baths 
5
Full Baths 
4
Partial Baths 
1
Lot Size 
0.43 Acres
Year Built 
2000
MLS® Number 
O6385964
Status 
Active
Property Tax 
$5,551
HOA/Condo/Coop Fees 
$500 Semi-Annually
Sq Ft Source 
Appraiser
Friends & Family
Recent Activity
3 hours agoListing updated with changes from the MLS®
20 hours agoListing first seen on site
General Features
Acres 
0.43
Attached Garage 
Yes
Direction Faces 
Northwest
Foundation 
Slab
Garage 
Yes
Garage Spaces 
3
Levels 
Two
Parking 
DrivewayAttached
Pets 
Yes
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Total 
4870
Utilities 
Cable AvailableElectricity ConnectedWater Connected
Water Source 
Public
Zoning 
R-1
Interior Features
Appliances 
CooktopDishwasherRefrigerator
Cooling 
Central Air
Fireplace 
Yes
Fireplace Features 
Family Room
Flooring 
CarpetTileWood
Furnished 
Unfurnished
Heating 
CentralElectric
Interior 
Crown MoldingHigh CeilingsOpen FloorplanWalk-In Closet(s)
Laundry Features 
InsideLaundry Room
Spa 
Yes
Great Room 
Dimensions - 27x18Level - First
Kitchen 
Dimensions - 11x10Level - First
Master Bedroom 
Dimensions - 18x13Level - Second
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Exterior Features
Construction Details 
BlockConcreteStuccoFrame
Exterior 
Outdoor ShowerRain Gutters
Fencing 
Vinyl
Pool Features 
GuniteIn GroundPrivate
Private Pool 
Yes
Roof 
Shingle
Spa 
Yes
Spa Features 
In Ground
Community Features
Association Dues 
500
Financing Terms Available 
CashConventionalFHAVA Loan
HOA Fee Frequency 
Semi-Annually
MLS Area 
34787 - Winter Garden/Oakland
Roads 
Asphalt
Township 
22
Schools
School District
Unknown
Elementary School
Tildenville Elem
Middle School
Lakeview Middle
High School
West Orange High
Listing courtesy of LAKESIDE REALTY WINDERMERE INC (321) 948-8056

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Listing information is provided by Participants of the Stellar MLS. 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. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-03-06 10:10 AM EST

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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