New Listing - 03/05/2026 Price Reduced 6.91%

$1,280,000 ($319.92 per sqft)

Est. Mortgage $6,222/mo *

Quick Pre-Approval

Price History

$1,375,000
3/5/2026

$1,280,000
3/12/2026


441 COURTLEA OAKS BOULEVARD, Winter Garden, FL, 34787

441 COURTLEA OAKS BOULEVARD, Winter Garden, FL, 34787

3 rooms

5 beds

4 Full / 1 Half baths

2000

4,001 sqft

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.


Status:

Active

Type:

Single-family residential

Furnished Remarks:

Unfurnished

Laundry Remarks:

Inside, Laundry Room

Subdivision:

COURTLEA OAKS

Garage:

3-car Driveway

Heating:

Central, Electric

Cooling:

Central Air

Common Charge:

$500 Semi-Annually

Acreage:

0.43

Est. Taxes:

$5,551

HOA Fee

$500

Construction

Block, Concrete, Stucco, Wood Frame

Utilities

Cable Available, Electricity Connected, Public, Water Connected

Elementary School:

Tildenville Elem

Middle School:

Lakeview Middle

High School:

West Orange High

Days on Market:

7

Pet Policy:

Yes

Appliances:

Built-In Oven, Cooktop, Dishwasher, Refrigerator

Pool:

Gunite, In Ground, Lighting

Min Lease Term:

7 Months

MLS #:

O6385964


Community Info

School Info

Walk Score

Yelp


Listing courtesy of LAKESIDE REALTY WINDERMERE INC 407-876-5575