Winesap is one of America's most beloved heirlooms apples, particularly in the southern states, where the variety performs well in spite of hot, dry summers and clay soils. The tree is moderately vigorous, slightly droopy, and crops reliably, though thinning will improve fruit size. It is highly resistant to cedar-apple rust, moderately resistant to powdery mildew and fireblight, but susceptible to scab. Although Winesap has an unusual and attractive pink bloom, it is triploid and cannot be used as a pollenizer; two diploid trees should be present for full fertility.

The apple is smallish, particularly if crops are not well thinned. The skin is a deep, dark purple-red over yellow with russeting around the stem. The flesh is yellowish, crisp, and juicy and firm enough to be a good baking apple. The spicy and vinous flavor also lends itself to cider making, and Albemarle Ciderworks make a single-variety cider from Virginia Winesap, which contains notes of "baked apple, cedar, and strawberry." These apples will store well for more than three months.

This was once one of the most widely propagated varieties in America. Although the ultimate origin of Winesap is unknown, Virginia Winesap is a redder sport of Winesap that grew in Troutville, Virginia in 1922. Stayman, Blacktwig, and Arkansas Black are all seedlings of Winesap.