The Union School is in the center of rural Hartford, Oxford County, Maine. The gable front vernacular schoolhouse with minimal Colonial Revival Style details is significant at the local level under Criterion A for its association with patterns of rural education and under Criterion C for its distinctive architectural characteristics of a rural one room schoolhouse. The building represents Hartford's response to evolving educational practices which were often mandated by state law.

The circa 1807 Captain Johnson H. Stover Jr. House in Harpswell, Cumberland County, Maine, is significant under Criterion C for Architecture as a locally significant example of Federal style architecture with mid-nineteenth century Greek Revival style interior updates to several rooms. Its character-defining features include a symmetrical five-bay faade with pilastered door surround; a hipped roof; Federal style mantles and trim in the principal rooms and a triple-run stair with a newel post typical of local early-nineteenth century design.

Southgate Farm in Scarborough, Cumberland County, Maine is significant as a well-preserved example of a rural New England Federal style brick farmhouse with later Colonial Revival additions. The house embodies distinctive characteristics of Federal style design in its form, proportions, plan, detailing, and materials. The original main block features a rectangular footprint (nearly square), low hip roof, and elegant neoclassical ornamentation, all hallmarks of the Federal style.

The Rangeley Tavern in Rangeley, Franklin County, Maine was constructed in 1908 on the site of an earlier hotel which was moved in 1895. Designed by the Maine architectural firm of Miller and Mayo, the three-story Colonial Revival style building with wraparound porch overshadowed a small two-story section of the earlier hotel that remained on the site and was incorporated into the Tavern. The Rangeley Lakes region was and remains a tourist destination centered on outdoor pursuits, particularly fishing.

The Herbert in Kingfield, Franklin County, Maine is a small-town hotel associated with tourism in the Maine woods. The Kingfield House hotel was purchased in 1917 by Herbert S. Wing, heavily remodeled and reopened as the Herbert. The hotel is significant under Criteria A for its association with Entertainment / Recreation centered around outdoor pursuits like hunting, fishing, hiking, and skiing. The building is also significant under Criteria C, Architecture for its Colonial Revival style design and typical early twentieth century hotel construction.

The 1920 Hartford Fire Station in Augusta, Kennebec County, Maine is eligible for the National Register of Historic Places at the local level of significance under Criterion A: Politics/Government for its association with municipal fire protection services in the city of Augusta. It represents one period within the local city government's efforts to provide modern and efficient fire protection services to the community, as required under the city charter and ordinances.

The Tolman Cemetery is located in a built-up rural section of Rockland, Knox County, Maine. The cemetery was donated to the town by Isaiah Tolman in 1783 as the first public burial ground in the vicinity. The cemetery is significant under Criterion A for its association with early exploration and settlement in the area. The majority of graves dates from 1788 to 1850 and represents early families who settled the area. A large number of the graves are of early town officials, Revolutionary War soldiers and War of 1812 soldiers.

The Dark Harbor Shop on the island town of Islesboro, Waldo County, Maine meets National Register eligibility Criterion A, for its associations with commerce related to the development of the Dark Harbor summer colony on Islesboro. This summer colony is representative of the leisure time development that occurred along the coast of Maine in the last half of the nineteenth century, as middle and upper class urban residents sought to escape the summer heat and disease of crowded eastern cities for what they considered a simpler and more healthful way of life.

The Fives Court is a specialized recreation building located in Lovell, Oxford County, Maine. The building was originally constructed in 1924 as part of Westways Kezar a vacation and corporate retreat built by William Armstrong Fairburn. The complex was built on Kezar Lake near the White Mountains and a few miles from New Hampshire. Built in a Craftsman style with limited decorative details on the exterior, the one-story, one-room Fives Court interior reveals distinct characteristics common to this rare type of sporting court.

The Brick School is eligible for the National Register under Criteria A: Education at the local level, as an example of a community school that was enlarged and adapted to meet the changing educational needs of the South Paris community over a period of many decades. The rebuilding of the 1883 Italianate style Brick School in a restrained Classical Revival style in1940 reflected changing national standards for school construction and a trend toward consolidation of small (typically one room) neighborhood schoolhouses into larger buildings serving children from a wider area.