No, you won't have to enter these transactions separately. During the 1099-B interview, you'll have the option to enter a summary for each sales category. (Click the attachment below to enlarge it for reference.) If you need help, just click the How do I figure this out? links when you are on the Tell us about your 1099-B page.
Note: You may be able to import your 1099-B if your brokerage participates in the TurboTax Partner program. See the FAQ below for more information.
How do I import my 1099? https://ttlc.intuit.com/replies/3389470Maybe... The 1099-B import *almost* works. See https://ttlc.intuit.com/community/taxes/discussion/re-i-imported-my-1099-b-directly-from-betterment-and-now-turbotax-is-telling-me-the-disallowed/01/1963147/highlight/false#M706341 for some details. You may be able to import but still have to make hand edits to dozens to hundreds of transactions because the import does rounding incorrectly. I’m not sure I’ll use TurboTax next year for this reason alone as I’m in the same boat using Betterment TLH+ myself.