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/3389470
