441 COURTLEA OAKS BOULEVARD Winter Garden, FL $ 1,375,000
441 COURTLEA OAKS BOULEVARD
$ 1,375,000
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441 COURTLEA OAKS BOULEVARD

Winter Garden, FL, 34787
$ 1,375,000
Bedrooms5 Baths4.1 Sq 4,089

Monthly Estimate*

$ 8,466

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View a Virtual Tour

Single Family Home for sale in Winter Garden, FL

for $1,375,000 with 5 bedrooms and 4 full baths, 1 half bath. This 4,089 square foot home was built in 2000 on a lot size of 0.43.

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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Single Family Active

Price

$ 1,375,000

Bedrooms

5

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 5,551

Style

Single Family Residence

Lot Size

0.43

Year Built

2000

Town/City

Winter Garden

County/Region

Orange

MLS | Web ID

O6385964

Features
General
Sewer Public Sewer
Heating Central Electric
Cooling Central Air
Utilities Cable Available Electricity Connected Public Water Connected
Roof Shingle
Appliances Built-In Oven Cooktop Dishwasher Refrigerator
Zoning R-1
HOA Fee 500
Garage Spaces 3
Pool Features Gunite In Ground Lighting
Construction Materials Block Concrete Stucco Wood Frame
Pets Allowed Yes
Year Built 2000
Levels Two
Property Subtype Single Family Residence
Tax Year 2024
Ownership Fee Simple
Assoc Fee Paid Per Semi-Annually
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name COURTLEA OAKS
Facing Direction Northwest
Garage Y/N true
Total Rooms 3
Full Baths 4
Status Active
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.
High School West Orange High
City WINTER GARDEN
Association Name Edison Association Management
Senior Community Y/N false
MLS Area 34787 - Winter Garden/Oakland
Lot Size Units Square Feet
Lot Size Square Feet 18602
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Spa Features In Ground
Elementary School Tildenville Elem
Land Lease Y/N false
Tax Annual Amount 5551
Middle/Junior High School Lakeview Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6385964
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 26
Legal Description COURTLEA OAKS PHASE 2B 41/67 LOT 26
Minimum Lease 7 Months
Water Access Y/N false
Monthly HOA Amount 83.33
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Ceiling Fan(s) Crown Molding High Ceilings Open Floorplan Solid Surface Counters Solid Wood Cabinets Thermostat Walk-In Closet(s)
Flooring Carpet Tile Hardwood
Furnished Y/N Unfurnished
Fireplace Features Family Room
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 1
Laundry Features Inside Laundry Room
Total Bedrooms 5
Total Baths 5
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Exterior
Exterior Amenities French Doors Outdoor Shower Rain Gutters Sidewalk
Fencing Vinyl
Parking Features Driveway
Water Source Public
Lot Size Area 18602
Foundation Details Slab
Spa true
Building Area Total 4870
Lot Size Acres 0.43
Road Surface Type Asphalt
Private Pool true
Waterfront Y/N false
Covered Spaces 3
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* Excluded Features
List By
Lakeside Realty Windermere Inc

Broker

jenshopshouses@gmail.com

Email

Affordability Calculator

$8,929
Per Month
95%
5%
0%
Monthly Principal & Interest
$8,466
Monthly Property Taxes
$463
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
West Orange High High School High School
Pricing History
DatePricePrice ChangeDescription
3/5/2026$1,375,000 Listed Price

Map


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441 COURTLEA OAKS BOULEVARD, Winter Garden, FL, 34787 is a Single Family Home for sale at $1,375,000 with 4,089 sqft and a lot size of 0.43. 441 COURTLEA OAKS BOULEVARD has 5 bedrooms, 4.1 baths, and was built in 2000. The property's zip code is 34787 which is in Winter Garden, FL