John Whittlesey Jr. House

The Jedidiah Dudley House, (also known as the John Whittlesey Jr. House) is a historic house on Springbrook Road in Old Saybrook, Connecticut. Built in the second half of the 18th century, it is a good example of period architecture, and is notable for its association with a family of ferry operators on the nearby Connecticut River. It was listed on the National Register of Historic Places in 1982.

The Amtrak Old Saybrook–Old Lyme Bridge is the last crossing of the Connecticut River before it reaches Long Island Sound. It is a Truss bridge with a bascule span, allowing boat traffic to pass through. The bridge is owned by Amtrak and used by Northeast Regional, Acela Express, Shore Line East and a few freight trains traversing the Northeast Corridor. It can be seen from the Raymond E. Baldwin Bridge (Interstate 95 and U.S. Route 1), as well as from various points on Route 154.

The Parker House is a historic house at 680 Middlesex Turnpike in Old Saybrook, Connecticut. It is a roughly square 1+1⁄2-story wood-frame structure with a gambrel roof, built in 1679 by Deacon William Parker. It is believed to be one of the oldest houses in the state, and was listed on the National Register of Historic Places in 1978.

Old Saybrook station is a regional rail station in Old Saybrook, Connecticut. It is served by both Amtrak Northeast Regional intercity trains and CTrail Shore Line East commuter service.

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 

The William Tully House, also known as Hartsease or Heartsease, is a historic house at 135 North Cove Road in Old Saybrook, Connecticut. Built about 1750, it is a well-preserved and architecturally unusual example of period architecture. It also has a well-documented history, having association with one of Connecticut's leading physicians of the early 19th century, and an incident in the American Revolutionary War. It was listed on the National Register of Historic Places in 1982.

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 Old Lyme Congregational Church is located in Old Lyme, Connecticut. The church is noted as a favorite subject of Old Lyme Art Colony painters. It is affiliated with the United Church of Christ.

Springbank is a historic country estate at 69 Neck Road in Old Lyme, Connecticut. Built upon a small core structure dating from around 1730, the main house consists of an 1844 Greek Revival brick structure, to which a number of Colonial Revival additions and alterations were made between about 1930 and 1945. The property also includes formal gardens designed by landscape architect Marian Cruger Coffin. The property is notable as a well-documented and preserved smaller-scale example of her work. The property was listed on the National Register of Historic Places on August 17, 2001.

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.

Old Saybrook is a town in Middlesex County, Connecticut, United States. The town is part of the Lower Connecticut River Valley Planning Region. The population was 10,481 at the 2020 census. It contains the incorporated borough of Fenwick, and the census-designated places of Old Saybrook Center and Saybrook Manor.