Horace Belden School and Central Grammar School

The Captain Elisha Phelps House is a historic house museum at 800 Hopmeadow Street in Simsbury, Connecticut. The colonial-era house was built by David Phelps in 1711. His son Elisha Phelps received the land from his father and expanded the house in 1771. Elisha Phelps along with his brother Noah Phelps and others took part in the capture of Fort Ticonderoga in 1775. Capt. Phelps was appointed as commissary of the Northern Department by the Continental Congress.The house was used as a hotel named the Canal Hotel, after the War of 1812. It is located along what was the New Haven and Northampton Canal line.

Hendrick Cottage is a historic building in Simsbury, Connecticut, United States. Dating to around 1795, it is believed to have been built by John Poisson. In 1965, it was moved half a mile from its original location (on the north bank of Hop Brook facing West Street) to become part of the collection of nine buildings comprising the Massacoh Plantation, part of Simsbury Center Historic District. It is named for its last owner, Fanny Josephine Pomeroy Hendrick.The building is listed on the National Register of Historic Places.

The Simsbury Bank and Trust Company Building, also known as the former Town Hall Building, is a historic commercial and civic building at 760 Hopmeadow Street in Simsbury, Connecticut. Built in 1917, it is a prominent local example of Colonial Revival architecture with Beaux Arts features. It originally housed the town's first bank, and was its town hall between 1969 and 1984. The building was listed on the National Register of Historic Places in 1986.

The Simsbury Center Historic District is a 75-acre (30 ha) historic district located in the town center area of Simsbury, Connecticut. It encompasses seven blocks of Hopmeadow Street, as well as the cluster of commercial, civic, and residential buildings along Railroad, Station, and Wilcox Streets, and Phelps Lane. Although its oldest element is the cemetery (established 1688), most of its buildings were built in the late 19th and early 20th century. It was listed on the National Register of Historic Places in 1996.: 2 

Eno Memorial Hall is a historic civic building at 754 Hopmeadow Street in Simsbury, Connecticut. Built in 1932, it served historically as a courthouse, as a city hall, as an auditorium, and as government offices. It was designed by Roy D. Bassette, and was given to the town by Antoinette Eno Wood, who was descended from some of the town's early settlers. It presently serves as the town's senior center. The hall was listed on the National Register of Historic Places in 1993.

Simsbury station is a former railroad station in the center of Simsbury, Connecticut. Built in 1875, it is a distinctive example of a railroad station with Italianate styling. The building was listed on the National Register of Historic Places on March 26, 1976 as Simsbury Railroad Depot. Presently, it houses a restaurant, called "Plan B".

The Amos Eno House, also known as the Simsbury 1820 House, is a historic home at 731 Hopmeadow Street in Simsbury, Connecticut.

Westminster School is a private, coeducational college-preparatory, boarding and day school located in Simsbury, Connecticut accepting around 20% of applicants. The total student population is approximately 400, and includes pupils from 25 US states and 30 countries. It is also a member of the Founders League, an athletic league comprising ten college preparatory boarding schools in Connecticut and one in New York.

The Robert and Julia Darling House, now the Cannon Building, is a historic house at 728 Hopmeadow Street in Simsbury, Connecticut. Built in 1927 for a local business leader, it is one of the town's largest and most distinctive examples of Colonial Revival architecture. The house was listed on the National Register of Historic Places in 1991. It now houses professional offices.

Belden Forest is a 40-acre (16 ha) wooded area owned by the Town of Simsbury, which was inducted into the Old-Growth Forest Network in October 2019. The trails are open to the public.The property was previously part of the summer residence and estate of Amos R. Eno, and was acquired by the Town of Simsbury in 1946. The forest includes a large stand of old eastern white pines; many of which are over 100 feet tall. It also has beech trees, eastern hemlocks, oaks, maples and birch trees. All of the trees in the forest are permanently protected from commercial logging.

The Simsbury Townhouse is a historic municipal building at 695 Hopmeadow Street in Simsbury, Connecticut. Built in 1839, it was Simsbury's town hall until 1931, and is a good local example of Greek Revival architecture. It was listed on the National Register of Historic Places in 1993. It continues to serve as a community resource.

Simsbury Center is a census-designated place (CDP) that consists of the central settlement, and the neighborhoods immediately surrounding it, in the town of Simsbury, Connecticut, in the United States. As of the 2010 census, the CDP had a population of 5,836. The core area of the CDP is listed as the Simsbury Center Historic District on the National Register of Historic Places.