The Oldest Homes in Fairfield

Photographs by: Kendra Wingate

A set of legal and administrative regulations called ‘The Fundamental Orders’ was adopted on January 14, 1639, establishing Connecticut as a self-ruled entity. That autumn Roger Ludlow, one of the founders of the Colony of Connecticut, led a small group of men and a large herd of cattle to the shores of the Long Island Sound, known to the local Native Americans as Unquowa. Ludlow and his men established a settlement that became known as Fairfield, named for the hundreds of acres of salt marsh that bordered Connecticut’s Coast.

In the years between the early settlement and today, much change has occurred, yet extraordinarily, some of the original homes have victoriously remained, even after miraculously escaping the burning of Fairfield by British Troops in 1779 during the American Revolutionary War.

These homes are amongst those that survived the ‘burning’ in 1779.

The oldest homes in Fairfield, CT

The John Osborne House (the oldest house in Fairfield) circa 1673

This antique saltbox house is architecturally significant as an early Colonial era house whose intact framing is unusual in its nonconformance to supposed patterns. The house’s exact age in not known however there are suggestions it may have been built as early as 1673. It is located adjacent to the Pequot Swamp, the site of the last battle in the Pequot War of 1637.

909 Kings Highway West

Ebenezer Peter Bulkley House: circa 1750

Image via Historic Buildings of CT

A saltbox house that survived the ‘burning.’

349 Beach Road

David Ogden House: 1750

Built in 1750 as an integral saltbox, this house is an exceptional survivor of a typical mid-18th century Connecticut farmhouse featuring a massive central field stone fireplace and chimney, topped with brick. It remained home to the Ogden family for the next 125 years, in this farming and coastal shipping town. The house presently serves as a museum for the Fairfield Historical Society.

1520 Bronson Road

Nathan Bulkley House: 1750

Photographed By Michael Herrick / via The Historical Marker Database

Nathan Bulkley was said to have been the ‘Deacon in the Congregational Church; a prominent man in town affairs and the Town Clerk for 82 consecutive years’. This Colonial house was built in 1750.

303 Beach Road

General Gold Selleck Silliman House: 1756

Built in 1756 and known as ‘The Orchard’ this home was owned by Revolutionary War General Silliman who took part in the battle of Ridgefield in 1777. In May 1779, he and his sons were captured in this home by a party of Tories who had crossed Long Island Sound during the night. U.S. Navy Captain David Hawley later captured Thomas Jones, a highly reputed loyalist, to exchange for Silliman a year after his capture. This house was also used as a place of refuge by citizens fleeing the British burning of Fairfield. Silliman’s son Benjamin became the first professor of science at Yale University and the first to distill petroleum.

506 Jennings Road

Justin Hobart House: 1765

Built in 1765 by a local cabinetmaker, this house became the meeting place where church and court sessions where held, after the burning, until a new meeting house was built in 1785.  During World War I this house also served as the headquarters for the Fairfield Chapter of the American Red Cross.

289 Beach Road

Isaac Tucker House: 1766

Tradition holds that a servant, hiding upstairs, put out the flames and saved this house from destruction, after the British Troops torched it. Burn marks remain to this day inside. The house was later owned by Edmund Hobart, who served as the Postmaster in Fairfield in the mid-nineteenth century.

249 Beach Road

The not so lucky prevailed on the Fairfield Green:

The Sun Tavern: was rebuilt in 1780 after having been burned during the British raid. The Tavern was operated by Samuel Penfield, who acquired the property in 1761. George Washington stayed at the Tavern the night of October 16, 1789, during a Presidential tour of New England. This Tavern had an early ball room on the third floor and remained a Tavern until Penfield’s death in 1811.

The Burr Homestead, Old Post Road, is a mansion that was rebuilt in 1790 by Thaddeus Burr, a wealthy landowner (after the original 1732 house was burned down – in spite of the pleas from Burr’s wife, Eunice, who even had the silver buckles stolen from her shoes by British Soldiers). In the earlier house, in 1775, Burr’s friend John Hancock married Dorothy Quincy, whose father was an old friend.

The Old Town Hall was rebuilt in 1794 as a county courthouse, replacing its 1769 predecessor that was burned by the British. The structure replaced the earliest courthouse in town which was built in 1720. The 1769 building “had only recently been erected in place of the one standing before where Mr. Hobart’s store now stands. A noted thief named Fraser, confined in the jail then connected with it, had set that building on fire April 4th, 1768. Hence had come the rebuilding, and the erection of a separate prison which was located where St. Paul’s Church now stands,” according to the Centennial Commemoration of the Burning of Fairfield, Connecticut.

611 Old Post Road

For more info about Fairfield’s historic homes, visit:

Related Articles

Eleish Van Breems Home’s Sunny New Collection

Nantucket-inspired daffodils adorn Agneta Livijn’s new Springtime dinnerware for Eleish Van Breems

SouthPaw: Darien Student’s New Novel

Darien Student Publishes Novel about Left-Handed Heroines at a...

Let’s Get the (Greenwich Town) Party Started

Welcoming Mumford & Sons to the Town Party stage • Q &A with key players and famous faces behind GTP