Roasted Tomato Pesto Grilled Cheese

Featured in: Oven-Finished Dishes

This elevated grilled cheese combines slow-roasted tomatoes with aromatic basil pesto and a blend of mozzarella and sharp cheddar cheese. The tomatoes are roasted low and slow for 50-60 minutes until deeply caramelized, then layered between buttered sourdough with pesto and melted cheese. Pan-seared until golden and crispy, it strikes the perfect balance between comfort food and gourmet indulgence. Ready in about 1 hour 15 minutes total.

Updated on Sat, 24 Jan 2026 02:11:35 GMT
Golden roasted tomatoes and melted mozzarella on a crispy sourdough sandwich spread with basil pesto.  Pin It
Golden roasted tomatoes and melted mozzarella on a crispy sourdough sandwich spread with basil pesto. | yummyhrira.com

This gourmet Roasted Tomato Pesto Grilled Cheese is a sophisticated twist on the classic childhood favorite. Featuring slow-roasted tomatoes that burst with concentrated sweetness, aromatic basil pesto, and a blend of gooey melted cheeses between slices of rustic sourdough, it is the ultimate choice for a comforting lunch or a light, flavorful dinner.

Golden roasted tomatoes and melted mozzarella on a crispy sourdough sandwich spread with basil pesto.  Pin It
Golden roasted tomatoes and melted mozzarella on a crispy sourdough sandwich spread with basil pesto. | yummyhrira.com

The secret to this sandwich's incredible flavor lies in the patience of roasting the tomatoes until they are perfectly caramelized. This step, combined with the herbal notes of the pesto and the richness of the buttered bread, creates a multi-layered taste experience that is both simple to achieve and incredibly rewarding.

Ingredients

  • Roasted Tomatoes: 2 large ripe tomatoes (sliced 1/4-inch thick), 1 tbsp olive oil, 1/4 tsp sea salt, 1/4 tsp freshly ground black pepper, 1/4 tsp dried oregano.
  • Sandwich Assembly: 4 slices rustic sourdough or country bread, 2 tbsp unsalted butter (softened), 2 tbsp basil pesto (homemade or store-bought), 4 slices mozzarella cheese (or provolone/fontina), 4 slices sharp cheddar cheese, optional handful of baby spinach or arugula leaves.
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Instructions

Step 1: Roast the Tomatoes
Preheat your oven to 300°F (150°C) and line a baking sheet with parchment paper. Arrange the tomato slices on the sheet, drizzle with olive oil, and sprinkle with salt, pepper, and oregano. Roast for 50–60 minutes, flipping halfway through, until the tomatoes are deeply caramelized but still hold their shape. Let them cool slightly.
Step 2: Prepare the Bread
Spread the softened butter on one side of each bread slice. Place two of the slices, buttered side down, on a clean surface.
Step 3: Assemble the Sandwiches
On the unbuttered side of the slices, spread 1 tablespoon of basil pesto. Layer each with two slices of mozzarella, the caramelized roasted tomatoes, two slices of sharp cheddar, and a handful of spinach or arugula if using. Top with the remaining bread slices, buttered side up.
Step 4: Grill to Perfection
Heat a large skillet or griddle over medium-low heat. Add the sandwiches and cook for 4–5 minutes per side. Press down gently with a spatula until the sourdough is golden brown and the cheese is completely melted and gooey.

Zusatztipps für die Zubereitung

For an extra kick of flavor, consider adding a pinch of red pepper flakes to your pesto before spreading. If you have dietary restrictions, this recipe can easily be made gluten-free by substituting the sourdough with your favorite gluten-free bread option.

Varianten und Anpassungen

Customize your cheese profile by experimenting with smoked gouda or gruyère instead of mozzarella or cheddar. You can also swap the basil pesto for a sun-dried tomato pesto to intensify the savory tomato notes in the sandwich.

Serviervorschläge

To round out this meal, serve the grilled cheese alongside a crisp green salad tossed in a light vinaigrette or a steaming cup of classic tomato soup for the ultimate comfort food pairing.

Gourmet roasted tomato pesto grilled cheese with gooey cheese and caramelized tomatoes in rustic bread.  Pin It
Gourmet roasted tomato pesto grilled cheese with gooey cheese and caramelized tomatoes in rustic bread. | yummyhrira.com

Once the sandwiches are beautifully golden and the cheese is oozing out the sides, remove them from the heat. Slice them in half and serve immediately while the bread is crispy and the interior is warm and delicious.

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Recipe FAQs

Can I prepare the roasted tomatoes ahead of time?

Yes, roast the tomatoes up to 2 days in advance. Store them in an airtight container in the refrigerator. Bring them to room temperature before assembling your sandwich.

What's the best cheese combination for this sandwich?

Mozzarella provides creaminess while sharp cheddar adds depth and flavor. For variations, try smoked gouda, gruyère, or provolone. Avoid using cheese that won't melt smoothly.

How do I prevent the bread from getting soggy?

Butter both outer sides of the bread generously before cooking. This creates a protective barrier. Let roasted tomatoes cool completely before assembling, and don't over-layer toppings.

Can I make this gluten-free?

Absolutely. Simply substitute your favorite gluten-free bread. The rest of the ingredients are naturally gluten-free. Ensure your pesto is also gluten-free if store-bought.

What's the ideal cooking temperature for the pan?

Medium-low heat is essential. This allows the cheese to melt completely while the bread toasts to golden brown without burning. Cook 4-5 minutes per side, pressing gently with a spatula.

Are there allergens I should be aware of?

This contains wheat, milk, and often nuts depending on pesto. Many store-bought pestos include pine nuts, so check labels carefully if you have nut allergies.

Roasted Tomato Pesto Grilled Cheese

A gourmet twist on classic grilled cheese with slow-roasted tomatoes, basil pesto, and melted cheese on rustic bread.

Prep Duration
15 minutes
Cook Duration
65 minutes
Overall Time
80 minutes


Level Easy

Cuisine American Italian Fusion

Makes 2 Portions

Diet Preferences Meat-Free

What You Need

Roasted Tomatoes

01 2 large ripe tomatoes, sliced 1/4 inch thick
02 1 tablespoon olive oil
03 1/4 teaspoon sea salt
04 1/4 teaspoon freshly ground black pepper
05 1/4 teaspoon dried oregano

Sandwich

01 4 slices rustic sourdough or country bread
02 2 tablespoons unsalted butter, softened
03 2 tablespoons basil pesto, homemade or store-bought
04 4 slices mozzarella cheese
05 4 slices sharp cheddar cheese
06 Handful of baby spinach or arugula leaves, optional

Step-by-Step

Step 01

Prepare Oven and Baking Sheet: Preheat oven to 300°F. Line a baking sheet with parchment paper.

Step 02

Roast Tomatoes: Arrange tomato slices on the prepared baking sheet. Drizzle with olive oil and sprinkle with salt, pepper, and oregano. Roast for 50 to 60 minutes, flipping halfway through, until tomatoes are deeply caramelized but still hold their shape. Allow to cool slightly.

Step 03

Butter Bread Slices: Spread butter on one side of each bread slice. Place 2 slices with buttered side down on a clean work surface.

Step 04

Layer Sandwich Fillings: Spread 1 tablespoon pesto on the unbuttered side of each bread slice. Top each with 2 slices mozzarella cheese, a layer of roasted tomatoes, 2 slices cheddar cheese, and spinach or arugula if desired. Cover with remaining bread slices, buttered side facing up.

Step 05

Cook Sandwiches: Heat a large skillet or griddle over medium-low heat. Add sandwiches and cook 4 to 5 minutes per side, pressing gently, until golden brown and cheese is fully melted.

Step 06

Serve: Slice each sandwich in half and serve immediately.

Cooking Tools

  • Baking sheet
  • Parchment paper
  • Large skillet or griddle
  • Spatula
  • Sharp knife

Allergy Details

Look at each ingredient for allergens. Not sure? Please check with your doctor.
  • Contains wheat from bread
  • Contains milk from butter and cheese
  • Pesto may contain tree nuts such as pine nuts
  • Verify pesto ingredients for potential allergens including milk and nuts

Nutrition Details (per serving)

This is for general reference. For health matters, turn to your doctor.
  • Calorie Count: 520
  • Fat Content: 30 grams
  • Carbohydrates: 38 grams
  • Proteins: 22 grams