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$1,160,000

  • Sold
  • Closed
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,001 Sq. Ft.
  • Updated 8 days ago
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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 for 441 Courtlea Oaks Blvd

General

  • Sold For: $1,160,000
  • HOA FEE: $83/month
  • HOA FEE FREQ.: Semi-Annually
  • Taxes: $5,551 (2024)
  • Status: Closed
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6385964
  • Added to Site: 110 day(s) ago

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: 4,001
  • Sq. Ft. Source: Appraiser
  • Living Area: 4,001 Sq. Ft.
  • 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
Sold by Avanti Way Realty Llc

Listing agent

— 441 Courtlea Oaks Blvd —

  • Lakeside Realty Windermere Inc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 441 Courtlea Oaks Blvd

School District:Orange County School District
NameGradesDistance
Dillard Street Elementary School
311 North Dillard Street, Winter Garden, FL 34787
PK-50.4 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-81.8 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-122 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 441 Courtlea Oaks Blvd

Date
Details
Price
Change
Source
6/15/2026
Sold
$1,160,000
-3.33%
MLS
4/03/2026
Price Increased
$1,199,900
7.23%
MLS
4/02/2026
Price Reduced
$1,119,000
-8.95%
MLS
3/19/2026
Price Reduced
$1,229,000
-3.98%
MLS
3/12/2026
Price Reduced
$1,280,000
-6.91%
MLS
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.

Listed by Lakeside Realty Windermere Inc
Sold by Avanti Way Realty Llc

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441 Courtlea Oaks Boulevard, Winter Garden, FL 34787 (MLS# O6385964) is a Single Family property that was sold at $1,160,000 on June 15, 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.