Is there anything better than the nostalgic taste of tomato soup and a grilled cheese sandwich? This recipe is a go-to for those cooler nights when you need the comfort food from your childhood to warm you up. The best part is that this grown-up version is packed with a natural sweetness from roasting the tomatoes yourself. As with all my recipes, I encourage you to pin this to your board for later. You'll definitely want to make this!

WW Friendly Recipe for Roasted Heirloom Tomato Soup with Grilled Cheese Croutons

Roasted Heirloom Tomato Soup with grilled cheese crouton

If you have never roasted your own tomatoes before, I encourage you to really give it a shot. There's something so delicious about freshly roasted tomatoes, so much so that I often love to roast a huge batch at a time for various different recipes, including canning my own tomato sauce. (If you click that little hyperlink by the way, there's a free course on there to teach you the basics of canning!)

What is the difference between Heirloom tomatoes and regular tomatoes?

Tomatoes actually come in thousands of different varieties, although the most common type of tomato is the Globe which is a large, round and red tomato which are the ones you would find easily on the supermarket shelf. An heirloom tomato is defined as a plant that has not been crossbred or hybridized for at least 40 years. This means that the farmer growing these tomatoes use the seeds from one harvest to plant the next one. These tomatoes will typically have a darker color and often have less acid than a more red tomato.

Can I Use Different Varieties and Colors of Tomatoes?

I know it can be tempting to use different varieties and mix up red and yellow tomatoes. While the taste should still be amazing, you may find that the look of the soup comes out with an unpleasant color. When you roast tomatoes, they will get a nice browning and that can create a darker color and sweeter flavor than you may be used to.

How Do You Roast Tomatoes?

Roasted Heirloom Tomatoes

Start off with slicing your tomatoes and placing them in a single layer on a rimmed baking sheet with parchment so that they aren't touching each other. Season them with a little salt and pepper and let them roast in a 300 degree oven for about 2 hours or until the tomatoes are browned around the edges.

What Products Do You Need For This Recipe?

You don't necessarily need anything fancy, however you should at least have a basic baking sheet, a blender or food processor and a stock pot. For the grilled cheese, you can make it extra fancy by using a grill pan or a panini press but a regular flat pan can work just as well. In the past, I have also used my instapot to make this tomato soup to speed up the process when I was too impatient. If you decide you want to go shopping, these are the products I use at home:

Can I use a different kind of cheese?

If you don't like brie, then by all means, use something different! My husband's favorite kind of cheese is brie, so it's worth the extra points if I can do something nice for him! However, myWW did post a guide to choosing the best cheese for the lowest points. You could try some of these varieties to really change up the flavor of the grilled cheese croutons to take your myww friendly lunch to the next level.

  • Laughing Cow Light Swiss or Light Queso Fresco & Chipotle or Light French Onion (1 point)
  • Velveeta Slices in Original or Cheddar (1 point)
  • President Fat Free Feta Crumbles (ZERO points)
  • Any Kraft Fat Free Cheese (Zero Points)
  • Alouette crumbled goat cheese (3 points for 1 oz)

Is there a brie that is low points?

Trader Joes has so many awesome products for those of us following myww plans. In fact, they offer mini brie bites that are only 3 points!

How Do You Make Roasted Heirloom Tomato Soup with Grilled Cheese Croutons?

Start with simple, fresh ingredients: heirlooms tomatoes, basil, garlic, onions, garlic and celery. (If you can get them from a local farmer's market, that's even better!) This recipe uses heavy cream and sourdough bread, but you can easily lighten up the points by using wheat bread, light butter and skim milk. Just keep in mind that a lot of the richness in the soup comes from the cream and butter so it can affect the taste.

How Many Points Are In This Recipe?

With the new PersonalPoints Plan, points can vary for each individual person based on their unique list of zero point foods. Points can also vary with different brands. Please use your recipe maker to determine your exact points.

Are You on WW Connect?

Find me on WW Connect @Sassycooking_Alyssa to see my full recipe list!

Weight Watcher Roasted Heirloom Tomato Soup with Grilled Cheese Croutons

Roasted Heirloom Tomato Soup with Grilled Cheese Croutons

Yield: 4
Prep Time: 20 minutes
Cook Time: 2 hours
Total Time: 2 hours 20 minutes


  • 2 lbs. ripe yellow or red tomatoes, cut into ½ inch slices
  • 1 tbsp garlic powder
  • Sea salt and black pepper, to taste
  • 2 slices sourdough bread, crusts removed
  • 2 tbsp unsalted butter, melted
  • ½ cup chicken or vegetable broth
  • 1/3 cup fresh basil, roughly chopped, plus additional sprigs for garnish
  • 1 medium yellow onion, quartered
  • 2 large stalks celery, roughly chopped
  • 2 cloves fresh garlic, peeled
  • 1 tsp ground cumin
  • 3 tbsp heavy whipping cream, room temperature
  • 3 oz. Brie cheese, crust removed, cut into thin slices


  1. Preheat oven to 300ºF and line a large rimmed baking sheet with parchment paper or a Silpat™ baking sheet.
  2. Arrange sliced tomatoes on the prepared baking sheet without overcrowding. Sprinkle with garlic powder, and season with salt and black pepper, to taste. Place baking sheet in pre-heated oven and roast approximately 2 hours or until the tomatoes are browned around the edges.
  3. When the tomatoes are almost ready, cut each slice of sourdough bread into equal-sized rectangles and brush one side with melted butter. Place buttered side down on a grill pan set over medium heat. Once grill marks appear, remove from heat and flip each piece of sourdough over so the grill marks are facing up. Set aside.
  4. Remove tomatoes from oven and transfer to a high-powered blender or food-processor, along with the broth, basil, yellow onion, celery, garlic, cumin, and heavy cream. Season with salt and black pepper, to taste.
  5. Blend on high until smooth and thoroughly combined. Taste and adjust seasonings as needed. If desired, add additional broth or water, one tablespoon at a time, and re-blend to achieve desired consistency. Set aside.
  6. Place top oven rack on the second highest position and pre-heat the broiler to high.
  7. Top each slice of grilled bread with a piece of sliced Brie and place the grill pan under broiler for 1-2 minutes, or until the Brie is soft and just starting to melt. Don’t broil too long or the Brie will run off the bread base.
  8. To serve, transfer the hot soup to individual serving bowls and top with the grilled cheese croutons and a sprig of fresh basil, if desired. Enjoy!
Nutrition Information
Yield 4 Serving Size 1 grams
Amount Per Serving Unsaturated Fat 0g

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Roasted Heirloom Tomato Soup with Grilled Cheese Croutons
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