Roasted Tomato Pesto Grilled Cheese

Featured in: Easy Side Plates

This gourmet grilled cheese features slow-roasted tomatoes that caramelize for 50-60 minutes, bringing deep, sweet flavor to every bite. Layer them with fresh basil pesto, creamy mozzarella, and sharp cheddar between buttered sourdough slices. Toast on a skillet until the bread turns golden and the cheese melts into gooey perfection. Ready in just over an hour, it's comfort food elevated for lunch or dinner.

Updated on Sat, 24 Jan 2026 22:47:29 GMT
Golden roasted tomato slices and melted mozzarella peek from a toasted sourdough sandwich, with a side of fresh basil pesto and a green salad garnish. Pin it
Golden roasted tomato slices and melted mozzarella peek from a toasted sourdough sandwich, with a side of fresh basil pesto and a green salad garnish. | cozybatbout.com

A gourmet twist on the classic grilled cheese, this Roasted Tomato Pesto Grilled Cheese features slow-roasted tomatoes, vibrant basil pesto, and gooey melted cheese between slices of rustic bread. It is perfect for a comforting lunch or a light dinner that brings a touch of Italian-American fusion to your kitchen.

Golden roasted tomato slices and melted mozzarella peek from a toasted sourdough sandwich, with a side of fresh basil pesto and a green salad garnish. Pin it
Golden roasted tomato slices and melted mozzarella peek from a toasted sourdough sandwich, with a side of fresh basil pesto and a green salad garnish. | cozybatbout.com

Transforming basic ingredients into a gourmet meal is all about the details. By roasting the tomatoes slowly, you concentrate their flavor, which pairs beautifully with the herbal notes of the basil pesto and the richness of the melted cheese.

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: 4 slices rustic sourdough or country bread, 2 tbsp unsalted butter (softened), 2 tbsp basil pesto, 4 slices mozzarella cheese (or provolone or fontina), 4 slices sharp cheddar cheese, and an optional handful of baby spinach or arugula leaves.
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Instructions

Step 1
Preheat oven to 300°F (150°C). Line a baking sheet with parchment paper.
Step 2
Arrange tomato slices on the prepared baking sheet. Drizzle with olive oil, sprinkle with salt, pepper, and oregano. Roast for 50–60 minutes, flipping halfway, until tomatoes are deeply caramelized but still hold their shape. Let cool slightly.
Step 3
Spread butter on one side of each bread slice. Place 2 slices, buttered side down, on a clean surface.
Step 4
Spread 1 tbsp pesto on each unbuttered side. Top each with 2 slices mozzarella, a layer of roasted tomatoes, 2 slices cheddar, and spinach or arugula if using. Cover with remaining bread slices, buttered side up.
Step 5
Heat a large skillet or griddle over medium-low heat. Add sandwiches and cook 4–5 minutes per side, pressing gently, until golden brown and cheese is fully melted.
Step 6
Slice in half and serve immediately.

Zusatztipps für die Zubereitung

When preparing the tomatoes, ensure they are sliced 1/4-inch thick for even roasting. Letting them cool slightly after they are deeply caramelized will help maintain the sandwich's structure and prevent the bread from getting too soft during assembly.

Varianten und Anpassungen

For extra flavor, use sun-dried tomato pesto or add a pinch of red pepper flakes to the pesto. You can substitute gluten-free bread to make this recipe gluten-free, or try using smoked gouda or gruyère for a different cheese profile.

Serviervorschläge

This sandwich pairs exceptionally well with a crisp green salad or a cup of warm tomato soup. It is a hearty main dish that serves two people comfortably.

This gourmet Roasted Tomato Pesto Grilled Cheese features slow-roasted tomatoes and sharp cheddar between buttery, golden-brown bread slices, served as a comforting lunch. Pin it
This gourmet Roasted Tomato Pesto Grilled Cheese features slow-roasted tomatoes and sharp cheddar between buttery, golden-brown bread slices, served as a comforting lunch. | cozybatbout.com

Once the bread is perfectly golden and the cheese is gooey, slice your Roasted Tomato Pesto Grilled Cheese in half and serve it immediately for the best experience. Enjoy this delicious gourmet meal!

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Recipe FAQs

How do I get the tomatoes deeply caramelized?

Roast tomato slices at 300°F for 50-60 minutes, flipping halfway through. They should be shriveled and concentrated in flavor while still holding their shape. This slow roasting brings out natural sweetness and depth.

Can I make this with store-bought pesto?

Absolutely. Store-bought basil pesto works perfectly and saves time. For extra flavor, try sun-dried tomato pesto or add a pinch of red pepper flakes to the store-bought version.

What's the best way to get a crispy exterior?

Cook over medium-low heat for 4-5 minutes per side, pressing gently with a spatula. This allows the bread to crisp and brown evenly while giving the cheese time to fully melt without burning the exterior.

Can I substitute the cheese types?

Yes, experiment with smoked gouda, gruyère, provolone, or fontina. The combination of a creamy and a sharp cheese works best, but you can adjust based on your preferences.

How do I make this gluten-free?

Simply substitute gluten-free bread for the sourdough. The roasted tomatoes, pesto, and cheese work beautifully with gluten-free bread—just ensure your pesto is also gluten-free if using store-bought.

What should I serve alongside this sandwich?

A crisp green salad or cup of tomato soup pairs wonderfully. The acidity and freshness of the salad or soup complements the rich, melted cheese and roasted tomato flavors perfectly.

Roasted Tomato Pesto Grilled Cheese

Slow-roasted tomatoes meet basil pesto and melted cheese in this gourmet grilled cheese on rustic sourdough bread.

Prep duration
15 minutes
Cook duration
60 minutes
Overall time
75 minutes
Recipe by Noah Kendrick


Skill Level Easy

Cuisine American/Italian Fusion

Makes 2 Portions

Diet Info Vegetarian friendly

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
04 4 slices mozzarella cheese
05 4 slices sharp cheddar cheese
06 Handful of baby spinach or arugula leaves, optional

Directions

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 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, buttered side down, on a clean surface.

Step 04

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

Finish and serve: Slice sandwiches in half and serve immediately.

Tools Needed

  • Baking sheet
  • Parchment paper
  • Skillet or griddle
  • Spatula
  • Sharp knife

Allergy Notice

Check every item for allergens and ask a health expert if unsure.
  • Contains wheat from bread
  • Contains milk from butter and cheese
  • May contain tree nuts, specifically pine nuts from pesto
  • Verify pesto ingredient label for additional allergens including dairy and nuts

Nutrition details (per portion)

Nutrition details are for general reference. Don’t substitute for professional advice.
  • Calorie count: 520
  • Fat content: 30 g
  • Carbohydrates: 38 g
  • Proteins: 22 g