Date
Details
Price
Change
Source
3/05/2026
Listed
$1,375,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/79
$1,375,000 Just Listed
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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.
Full Property Details
Full Property Details for 441 Courtlea Oaks Blvd
General
- Price: $1,375,000
- HOA FEE: $83/month
- HOA FEE FREQ.: Semi-Annually
- Taxes: $5,551 (2024)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6385964
- Updated: Today (3/5/2026)
- Added to Site: Today
Rental Information
- Min. Lease: 7 Months
Interior
- Number of Rooms: 3
- Interior Features: Ceiling Fan(s), Crown Molding, High Ceilings, Open Floorplan, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Family Room
- Appliances: Built-In Oven, Cooktop, Dishwasher, Refrigerator
- Furnishings: Unfurnished
- Flooring: Carpet, Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 4
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 5
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, In Ground, Lighting
- Spa: Yes
- Spa Description: In Ground
Exterior
- Exterior Features: French Doors, Outdoor Shower, Rain Gutters, Sidewalk
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Driveway
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: COURTLEA OAKS
- Driving 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.
- Direction Faces: Northwest
School Information
- Elementary School: Tildenville Elem
- Middle School: Lakeview Middle
- High School: West Orange High
Community
- Community Name: 34787 - Winter Garden/Oakland
- Association: Yes
- Assoc. Name: Edison Association Management
- Pet Restrictions: Please confirm any restrictions with HOA.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable TV Available, Electricity Connected, Public, Water Connected
Structural Information
- Exterior Const.: Block, Concrete, Stucco, Wood Frame
- Roof: Shingle
- Stories/Levels: Two
- Square Feet: 4,089
- Sq. Ft. Source: Appraiser
- Year Built: 2000
Lot Features
- Lot Size (Acres): 0.43
- Lot Size (Sq. Ft.): 18,602
- Lot Size: 18602
- Street/Road Desc.: Asphalt
- Fencing (Description): Vinyl
Financial Considerations
- Association Fee: $500
- Assoc Fee Freq.: Semi-Annually
- Assoc Fee Desc.: Required
- Tax Amount: $5,551
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: COURTLEA OAKS PHASE 2B 41/67 LOT 26
- Flood Zone Info: X
- APN: 142227194400260
- Property ID: 142227194400260
- Block/Lot/Section: P
Listed by Lakeside Realty Windermere Inc
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 441 Courtlea Oaks Blvd —
Lakeside Realty Windermere Inc
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 441 Courtlea Oaks Blvd
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Dillard Street Elementary School 311 North Dillard Street, Winter Garden, FL 34787 | PK-5 | 0.4 mi |
Lakeview Middle School 1200 West Bay Street, Winter Garden, FL 34787 | 6-8 | 1.8 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 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 441 Courtlea Oaks Blvd
Tax History
Tax History for 441 Courtlea Oaks Blvd
Year
Property Taxes
Change
Tax Assessment
Change
2024
$5,551
—
$399,113
3%
2024
$5,551
4%
$387,865
3%
2023
$5,356
4%
$376,568
6%
2021
$5,129
-1%
$354,951
-3%
2022
$5,201
1%
$365,600
4%
2021
$5,129
2%
$350,050
2%
2019
$5,045
1%
$342,180
2%
2018
$5,002
3%
$335,800
2%
2017
$4,873
—
$328,893
2%
2016
$4,865
-2%
$322,128
1%
2015
$4,950
-1%
$319,889
1%
2014
$4,984
2%
$317,350
2%
2013
$4,871
—
$312,660
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 441 Courtlea Oaks Blvd
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441 Courtlea Oaks Boulevard, Winter Garden, FL 34787 (MLS# O6385964) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 441 Courtlea Oaks Boulevard is currently listed for $1,375,000 and was received on March 05, 2026. Want to learn more about 441 Courtlea Oaks Boulevard? 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.