Gabriella Massaro

Gabriella Massaro Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

$1,199,900.00
441 COURTLEA OAKS BOULEVARD, WINTER GARDEN, FL - 34787
5 beds
4.5 baths
4,001 sqft
$1,199,900.00
441 COURTLEA OAKS BOULEVARD, WINTER GARDEN, FL - 34787
Gabriella Massaro
$1,199,900.00
5 beds
4.5 baths
4,001 sqft
441 COURTLEA OAKS BOULEVARD, WINTER GARDEN, FL - 34787
For Sale
Photo 1
  • Built in 2000
  • 3 garage spaces
  • $299.90/sqft
  • Lot size: 18,602 sqft
  • 28 days on market

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.

  • 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.
  • County: Orange
  • Geo subdivision: COURTLEA OAKS

Nearby Schools

Tildenville Elem

Lakeview Middle

West Orange High

Features

Financial

Let's get in touch!

Gabriella Massaro

Gabriella Massaro

Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

See also

For Sale
14254 SUNRIDGE BOULEVARD, WINTER GARDEN, FL - 34787
$1,150,000.00
5 bds
3.5 ba
4,004 sqft
14254 SUNRIDGE BOULEVARD, WINTER GARDEN, FL - 34787
For Sale
617 CANOPY ESTATES DRIVE, WINTER GARDEN, FL - 34787
$1,200,000.00
4 bds
4.5 ba
3,624 sqft
617 CANOPY ESTATES DRIVE, WINTER GARDEN, FL - 34787
For Sale
15226 SUNSET OVERLOOK CIRCLE, WINTER GARDEN, FL - 34787
$1,100,000.00
5 bds
4.0 ba
3,556 sqft
15226 SUNSET OVERLOOK CIRCLE, WINTER GARDEN, FL - 34787
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6385964
Listing updated: April 3, 2026 at 3:09AM
Listing provided by: Jennifer Coon, LAKESIDE REALTY WINDERMERE INC
Last checked 19 hours ago
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