Ultimate Grilled Cheese and Roasted Tomato Sandwich

Image of Suzan Najjar
Suzan Najjar Website
Rated 5.0 based on 4 customer reviews
Ultimate Grilled Cheese and Roasted Tomato Sandwich
Ultimate Grilled Cheese and Roasted Tomato Sandwich
Recipe Image for Print


  • 1 tablespoon extra-virgin olive oil
  • 10 ounces plum tomatoes, sliced
  • salt and freshly ground black pepper
  • 1/4 cup of pesto
  • 4 slices bread
  • 2 slices Havarti cheese
  • 2 slices mozzarella cheese
  • 1/4 cup grated Gruyère cheese
  • 3 tablespoons butter


  1. Preheat oven to 350°F (180°C).
  2. Toss tomatoes with olive oil to coat; season with salt and pepper. Spread tomatoes into a small baking dish.
  3. Bake tomatoes in preheated oven until tender, about 25 minutes.
  4. To arrange the sandwiches. Spread 1 tablespoon pesto onto one side of each bread slice. Top two portions of pesto with Havarti slices; top remaining two with mozzarella slices. Spread roasted tomatoes over Havarti cheese. Sprinkle Gruyère cheese over the tomatoes. Finish sandwiches with remaining mozzarella-topped bread slices.
  5. Spread butter onto both sides of of each sandwich.
  6. Heat a cast-iron pan over medium-high heat. Cook sandwiches in hot pan until cheese is melted, 1 to 2 minutes per side. Cut sandwiches into halves to serve.
Mealthy tip:

Feel free to substitute your favorite cheeses, such as Swiss, Fontina, Brie or Monterey Jack.


5.0out of 5 Stars

(4 Reviews)

How would you rate this recipe?

What others are saying

Image of Aja A
September 12, 2017 at 7:33am

Aja A says:

I took everyone's suggestions into consideration and roasted the tomatoes first. Also added bacon, because WHY NOT?! Bacon goes with everything and certainly in this grilled cheese sandwich. Never had havarti cheese before and I really enjoyed it.

Image of Jen the Mighty
September 11, 2017 at 11:58pm

Jen the Mighty says:

Tomatoes on grilled cheese with pesto is a revelation, and roasting them ahead of time is definitely genius, although I will also grill tomatoes and use them that way as well. Very delicious!

Image of Shannon Whittier
September 10, 2017 at 2:25am

Shannon Whittier says:

If you love cheese this is the sandwich for you. I added bacon to add some protein but could easily have gone without. The roasted tomatoes were the best part. Very good spin on grilled cheese sandwiches!

Image of Caro Hodgin
September 03, 2017 at 6:03am

Caro Hodgin says:

I've always loved putting fresh tomato slices in my grilled cheeses, but they always left the bread a bit undesirably soggy. Roasting the tomatoes this way pulls so much of the moisture out, eliminating that problem, but still leaves the tomatoes incredibly juicy and succulent. YUM. Will definitely use these roasted tomatoes elsewhere too - polenta bowls, with fried eggs for breakfast, alongside a simple steak and side salad for dinner.... the list goes on. I like cooking my grilled cheese over medium heat for a longer amount of time (3 to 4 minutes per side) because I'm prone to burning them, but otherwise I followed this recipe verbatim. YUM!