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Preheat oven to 350 degrees. Spread almonds on a small rimmed baking sheet; toast, stirring occasionally, until golden brown, 6–8 minutes. Let cool; coarsely chop.
Increase oven temperature to 425 degrees. Toss squash, carrots, fennel, beet and 2 tablespoons oil on a large rimmed baking sheet; season with sea salt and pepper. Roast vegetables, tossing occasionally, until soft and golden brown, 25–30 minutes. Let cool slightly.
Meanwhile, whisk vinegar, cumin, and remaining 3 tablespoons oil in a large bowl. Add roasted vegetables and toss to coat; season with sea salt, pepper and more vinegar, if desired.
Serve vegetables topped with toasted almonds and mint.