To accurately extract cultivated land boundaries based on high-resolution remote sensing imagery, an improved watershed segmentation algorithm was proposed herein based on a combination of pre- and post-improvement procedures. Image contrast enhancement was used as the pre-improvement, while the color distance of the Commission Internationale de l´Eclairage (CIE) color space, including the Lab and Luv, was used as the regional similarity measure for region merging as the post-improvement. Furthermore, the area relative error criterion (δA), the pixel quantity error criterion (δP), and the consistency criterion (Khat) were used for evaluating the image segmentation accuracy. The region merging in Red–Green–Blue (RGB) color space was selected to compare the proposed algorithm by extracting cultivated land boundaries. The validation experiments were performed using a subset of Chinese Gaofen-2 (GF-2) remote sensing image with a coverage area of 0.12 km2. The results showed the following: (1) The contrast-enhanced image exhibited an obvious gain in terms of improving the image segmentation effect and time efficiency using the improved algorithm. The time efficiency increased by 10.31%, 60.00%, and 40.28%, respectively, in the RGB, Lab, and Luv color spaces. (2) The optimal segmentation and merging scale parameters in the RGB, Lab, and Luv color spaces were C for minimum areas of 2000, 1900, and 2000, and D for a color difference of 1000, 40, and 40. (3) The algorithm improved the time efficiency of cultivated land boundary extraction in the Lab and Luv color spaces by 35.16% and 29.58%, respectively, compared to the RGB color space. The extraction accuracy was compared to the RGB color space using the δA, δP, and Khat, that were improved by 76.92%, 62.01%, and 16.83%, respectively, in the Lab color space, while they were 55.79%, 49.67%, and 13.42% in the Luv color space. (4) Through the visual comparison, time efficiency, and segmentation accuracy, the comprehensive extraction effect using the proposed algorithm was obviously better than that of RGB color-based space algorithm. The established accuracy evaluation indicators were also proven to be consistent with the visual evaluation. (5) The proposed method has a satisfying transferability by a wider test area with a coverage area of 1 km2. In addition, the proposed method, based on the image contrast enhancement, was to perform the region merging in the CIE color space according to the simulated immersion watershed segmentation results. It is a useful attempt for the watershed segmentation algorithm to extract cultivated land boundaries, which provides a reference for enhancing the watershed algorithm.