Ultimate Grilled Cheese and Roasted Tomato Sandwich

Image of Suzan Najjar
Rated 5.0 based on 5 customer reviews
Ultimate Grilled Cheese and Roasted Tomato Sandwich
Ultimate Grilled Cheese and Roasted Tomato Sandwich


  • 10 ounces plum tomatoes, sliced
  • 1 tablespoon extra-virgin olive oil
  • salt and freshly ground black pepper to taste
  • ¼ cup pesto
  • 4 slices store-bought or homemade bread
  • 2 slices Havarti cheese
  • 2 slices mozzarella cheese
  • ¼ 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 in the preheated oven until tender, about 25 minutes.
  4. Spread 1 tablespoon pesto onto one side of each bread slice. Top 2 pieces of bread with Havarti cheese slices; top remaining 2 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 each sandwich in half.
Mealthy tip:

Substitute your favorite cheeses, such as Swiss, Fontina, Brie, or Monterey Jack for the Havarti, mozzarella, or Gruyere cheese. Baked kale chips are a nice crunchy side to this decadent sandwich. Sparkling water with lemon pairs well with this grilled cheese. Or if you are in the mood for wine, have a glass of Pinot Gris.


5.0out of 5 Stars

(5 Reviews)

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What others are saying

Image of Aja A

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 Caro Hodgin

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!

Image of Shannon Whittier

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 Jen the Mighty

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 Jenny J

Jenny J says:

I added salami to this grilled cheese and tomato sandwich. My husband love, love, loved it. I also used a homemade pesto sauce, yum.