William Tully House

The Black Horse Tavern is a historic building at 175 North Cove Road in Old Saybrook, Connecticut. Built c. 1712 by John Burrows, this 2+1⁄2-story wood-frame structure is one of few early 18th-century buildings still standing in Connecticut, built on land that was among the earliest settled in the area. Now a private residence, it was listed on the National Register of Historic Places in 1978.

The North Cove Historic District encompasses a historic waterfront community on North Cove Road in Saybrook, Connecticut. Laid out in the 17th century, the area has housing stock mostly built between 1700 and 1855, a period in which it flourished as a port and shipbuilding community. The district was listed on the National Register of Historic Places in 1994.

The Saybrook Colony was an English colony established in New England in late 1635 at the mouth of the Connecticut River which today is Old Saybrook, Connecticut. Saybrook was founded by John Winthrop, the Younger, son of John Winthrop the Governor of the Massachusetts Bay Colony. Winthrop the Younger was designated Governor by the original settlers, including Colonel George Fenwick and Captain Lion Gardiner. They claimed possession of the land via a deed of conveyance from Robert Rich, 2nd Earl of Warwick. The colony was named in honor of Lords Saye and Brooke, prominent Parliamentarians and holders of the colony's land grants.

Cypress Cemetery is an historic cemetery at 100 College Street in Old Saybrook, Connecticut. Established sometime in the 17th century, and still in active use, it is the town's oldest cemetery, with a wide variety of funerary art dating from the 17th to 21st centuries. The cemetery's oldest portion was listed on the National Register of Historic Places in 2018.

The Connecticut Valley Railroad Roundhouse and Turntable Site is a former railroad facility located in Fort Saybrook Monument Park off Main Street in Old Saybrook, Connecticut. The roundhouse and turntable were built in 1871 by the Connecticut Valley Railroad, which was later acquired by the New York, New Haven and Hartford Railroad. The rail facilities are built partly on the archaeological remains of Fort Saybrook, the main fortification of the 17th-century Saybrook Colony, and are the only surviving remnant of what was once a large facility, with an icehouse, coal bin, steamboat dock, depot, and signal tower. Archaeological remains of these other facilities are believed to lie under other parts of the park and adjacent properties. The exposed facilities were excavated in 1981-2. Both structures were added to the National Register of Historic Places on April 28, 1994.The Connecticut Valley Railroad was chartered in 1868, and began operations three years later, providing service between Saybrook Point and Hartford, with a connection to the Shore Line Railway at the Saybrook Junction station. The extension to Saybrook Point ceased operations in 1922, and its facilities were abandoned. The roundhouse was a quarter-round structure housing six bays, with foundations of brick and stone, supporting both the structure and the tracks on which the railroad cars ran. The turntable had a concrete base. Portions of these features are exposed in the park, with interpretive signage explaining the use and history of the site.

The Samuel Eliot House is a historic house at 500 Main Street in Old Saybrook, Connecticut. Probably built in 1737, it is a well-preserved example of Georgian residential architecture, and one of Old Saybrook's older buildings. The house was listed on the National Register of Historic Places in 1972.

The Gen. William Hart House is a historic house at 350 Main Street in Old Saybrook, Connecticut. Built in 1767 for a politician and colonial militia leader, it is a good example of Georgian residential architecture. The house was listed on the National Register of Historic Places in 1972, and is a contributing property to the Old Saybrook South Green historic district.

Fenwick is a borough in Middlesex County, Connecticut, United States, in the town of Old Saybrook. The borough is part of the Lower Connecticut River Valley Planning Region. The population was 53 at the 2020 census, making it the least populous borough in Connecticut. Most of the borough is included in the Fenwick Historic District, listed on the National Register of Historic Places. In 1995, the district included 66 contributing buildings and one other contributing site.Fenwick is set off from the town center of Old Saybrook by a large cove crossed by a causeway. It is located exactly where the Connecticut River flows into Long Island Sound, and sits on the river's west side. The town has two lighthouses, the Inner and the Outer. The Inner is at the tip of Lynde Point, Fenwick's peninsula, and the Outer is a quarter mile off shore, connected by a rough jetty. The Outer Light is the lighthouse shown on many Connecticut license plates.

The Humphrey Pratt Tavern is a historic house at 287 Main Street in Old Saybrook, Connecticut. Built in 1785, it was associated with the locally prominent Pratt family for many years, and served as a tavern and stagecoach stop in the 18th and 19th centuries. It was listed on the National Register of Historic Places in 1976.

The James Pharmacy is a historic building at 2 Pennywise Lane in Old Saybrook, Connecticut. Built in an evolutionary manner beginning about 1820, it is significant as the home and workplace of Anna Louise James (1886–1977), who was the first African-American woman pharmacist in the state, and owned the pharmacy for some time. It is also the birthplace and childhood home of author Ann Petry, who was James' niece. The building was listed on the National Register of Historic Places in 1994, and is a contributing element in the Old Saybrook South Green district.

The Old Saybrook South Green is a 20-acre (8.1 ha) historic district that encompasses the historic town green and nearby streets in Old Saybrook, Connecticut. Established in the 1630s, most of the buildings arrayed around the green were built between 1760 and 1900, and reflect the prosperity of the town, which was a major port and shipbuilding center. The district was listed on the National Register of Historic Places in 1976.

The Ambrose Whittlesey House is a historic house at 14 Main Street in Old Saybrook, Connecticut that was listed on the National Register of Historic Places in 1985. The house was built in two sections. The first section was one story high, built in 1765, measuring 16 feet (4.9 m) by 30 feet (9.1 m). This is now at the rear of the house. Around 1800, a two-story main block measuring 30 feet (9.1 m) by 34 feet (10 m) was added. The main block has a relatively plain facade, but it has a Georgian style portico to accent it. The columns holding up the portico are consistent with Georgian proportions, but the fanlight over the door is more related to Federal architecture in style and design.: 2  The interior of the 1800 section of the house is generally consistent with Federal-style architecture.: 4  This section contains a massive center chimney, dating back to Colonial architecture in its simplicity. The chimney contains flues for six hearths, three on each floor.: 5 The house has architectural influences indicating a transition between Georgian architecture and Federal architecture. There are only a few such buildings remaining in this section of Old Saybrook. The actual identification of architectural styles is complicated by the mix of elements such as the large central chimney, reminiscent of colonial-period architecture; the Georgian-style portico, and the Federal-style detailing in the interior. Since there are few other Georgian-style details in the house, it appears likely that the portico was added later.: 5 The owner, Ambrose Whittlesey, was the great-great-grandson of John Whittlesey, who was an early settler of the Saybrook Colony in the 17th century. The Whittlesey family was involved in farming, the merchandise trade, and shipbuilding. Ambrose started his career as a sea captain at age 21, trading with the West Indies. He later went on to voyages to Spain and Portugal after the War of 1812. When he died in 1827, his house was inherited by his youngest son, also named Ambrose, although his mother had an encumbrance on the property until her death in 1838. In 1839, his surviving siblings granted him full ownership via a quitclaim deed. The house remained in the Whittlesey family until 1967.: 5