Heat olive oil in a large pot over medium heat for one minute. Add diced onion and sauté for 4-5 minutes until softened and fragrant, stirring occasionally to prevent browning.

Stir in minced garlic and tomato paste, cooking for 1-2 minutes until the mixture becomes deeply aromatic. This step builds incredible depth that elevates your summer tomato soup family recipe above ordinary versions.

Add chopped fresh tomatoes and vegetable broth to the pot, bringing the mixture to a gentle boil. Reduce heat to medium-low and simmer for 15-20 minutes, allowing flavors to meld beautifully while tomatoes break down completely.

Remove from heat and carefully blend the soup using an immersion blender until your desired consistency is reached. For chunkier texture, blend halfway; for silky smoothness, blend until completely uniform and creamy.

Stir in heavy cream, dried basil, dried oregano, sugar, salt, and pepper. Heat through gently for 2-3 minutes without boiling to preserve the delicate cream texture and fresh herb flavors.

While soup simmers, butter bread slices generously on both sides. Toast in a skillet over medium-high heat for 2-3 minutes per side until golden brown and crispy throughout.

Ladle soup into bowls and top with buttered toast pieces and shredded cheddar cheese. Serve immediately while everything is hot and the cheese begins melting into creamy pockets throughout the bowl.