Portland is about 1.8 times smaller than Stamford.

Stamford is approximately 97 sq km, while Portland (map shows its 17 named neighbourhoods; the area covers the whole city) is approximately 56 sq km, making Portland 57.24% the size of Stamford.
Tip: This to-scale comparison of Stamford vs. Portland uses the Mercator projection, which distorts the size of regions near the poles.
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