Compact growth habit (CGH) tomatoes (Solanum lycopersicum) are determinate plants with shortened internodes and strong side branching due to the brachytic gene (br) that grow either prostrate or upright as a result of unidentified gene(s). Compact growth habit tomatoes do not require staking, tying, or pruning and can potentially be mechanically harvested, lowering Florida fresh-market tomato production costs. Therefore, the objective of this study was to evaluate the effects of two planting configurations (single and double row) and breeding lines (BLs) on CGH tomato plant growth, flowering pattern, yield, and postharvest fruit quality. Two experiments were conducted in Immokalee, FL, during Spring 2013 and 2014 in a split-plot design with four replications. Planting configurations affected CGH tomato growth at midseason in 2013 but not in 2014; however, in 2014, CGH tomato vines grew outside the beds into the row middles, which is uncommon for this tomato type and undesirable. Plants of CGH tomatoes had a similar flowering pattern to a conventional upright tomato cultivar, which was unexpected. Planting configurations did not affect marketable yields in 2013, but single-row plots produced higher extra-large and total marketable yields at first and total season harvests in 2014. Total season marketable harvests ranged from 26.1 to 53.6 and 29.3 to 45.6 Mg·ha−1 in 2013 and 2014, respectively. Fla 8916 was among the highest yielding BLs, maximizing extra-large and total season marketable yields. Unmarketable fruit ranged from 22% to 31% and 25% to 52% of the total season harvest in 2013 and 2014, respectively, and the most common defects were sunscald, off-shape, catface, and graywall. All CGH evaluated may be suitable for mature-green harvest regarding postharvest fruit quality, although fruit ripening uniformity was of concern in 2014. Average CGH total season marketable yields harvested twice were lower than expected yields of staked-upright tomato cultivars that may be harvested three times, but higher than Florida average yields. However, CGH tomato total production cost can potentially be lower than staked-upright cultivars making CGH tomatoes a viable alternative for the Florida mature-green fresh-market industry to remain sustainable.