Sgt. John Smith House // c.1690

According to local historians, this historic saltbox house was built around 1690 by John Smith, a volunteer Sargent in the Fairfield Trainband (a band of citizens trained as soldiers to supplement the regular army) or Militia. The position involved training, strategizing, storing military weaponry of the town, and being responsible for the preparedness of the community in the event of an attack by Native tribes, Dutch, or French forces. The house was later renovated in the Colonial Revival style, but has since been restored closer to its original design as an early First Period saltbox.

Sturges House // 1855

One of the finest examples of Italianate residential architecture in the state of Connecticut can be found in Fairfield in the Sturges House. This property was built in 1855 for Henry Sturges Thorp a New York City merchant from a Fairfield family and his wife Julia Ann Thorp, likely as a summer home away from the city. Both Henry and Julia died in 1869 and the property was acquired by Frederick Sturges, the son of Jonathan Sturges a wealthy businessman and philanthropist who had a stunning early Gothic Revival mansion nearby. The Sturges House as it is now known, is a landmark example of the Italianate style with broad overhanging eaves, massive belvedere at the roof, round arched windows, and the tripartite blind windows capped by an elaborate cornice.

Frederic Bronson Barn // c.1895

Not many buildings in Greenfield Hill, Fairfield, Connecticut showcase the neighborhood’s transition from farming community to affluent suburb quite as well as this stone barn turned house on Hillside Road. The stone barn was constructed around c.1895 for Frederic Bronson Jr. (1851-1900) a prominent New York attorney and treasurer of the New York Life and Trust Company which was founded by his grandfather, Isaac Bronson. In about 1892, Frederic demolished his ancestral home and hired architect Richard Morris Hunt to design a new country estate for his family. The house was called Verna and is also located in Fairfield. Today Verna is known best as the Fairfield County Day School. As with many wealthy men of the Gilded Age, Frederic wanted his rural retreat to also work as a gentleman’s farm, where he could have staff farm and tend to livestock on the expansive rolling hills bounded by historic stone walls. He appears to have had this barn built for his livestock shortly after the main house, Verna was completed nearby. Bronson died in 1900 and some of the property was later sold off. This property was acquired by a Charles Stillman in 1941 and it is likely him that converted the barn into a charming residence.

Harold C. Bullard House // 1927

Some towns have the best (and high quantity of) examples of Colonial Revival houses in New England, and Fairfield, Connecticut is definitely one of those towns! This house on Barlow Road was erected in 1927 by Harold Camp Bullard (1879-1949), an engineer at the Bullard Machine Tool Company of Bridgeport, which was started by his father. The architect of the house is unknown, but the property stands out for its bold proportions, prominent Palladian window over the rounded entry portico, and rounded dormers at the gambrel roof.

Bradley-Wakeman House // c.1815

While the Greenfield Hill section of Fairfield, Connecticut has some of the grandest houses (old and new) in the state, there are some more average size homes that just ooze charm and curb appeal. This example on Hillside Road, dates to the 1810s and was seemingly built by Alban Bradley (1767-1832) on land inherited by him from his late father, Seth Bradley. The family farmed on the land from this Federal period farmhouse until it sold out of the family by Alban’s only son, Burritt in 1825. Burritt sold the farm to Zalmon Wakeman who farmed on the many acres of valuable land there. Sometime before his death before the Civil War, the house was “modernized” with Italianate-style porch, which is supported by delicate cut trelliswork. This is a great illustration as to how modest renovations which apply up-to-date decorative details can be done to historic properties without compromising the original structure or its architectural integrity.

Bradley-Baldwin House // pre-1750

WOW this is an absolute dream home! Tucked away on Meetinghouse Lane in the Greenfield Hill section of Fairfield, CT, you will find the Zalmon Bradley House. It was originally built around 1750 as a modest saltbox and later owned by Zalmon Bradley. The property was inherited by Zalmon’s sister, Sarah, who recently married Dudley Baldwin, an “ardent patriot”. The property was likely updated in appearance by Sarah and Dudley Baldwin giving the house its current four-sided hip roof, chimneys and an exquisite doorway. Dudley and Sarah died young in 1794 and 1795 (at ages 40 and 37 respectively), and the property was inherited by their only child, Abraham Dudley Baldwin. Abraham was watched for years by family, including his namesake, Abraham Baldwin (1754-1807), a senator, congressman, and key figure of the drafting and signing the U.S. Constitution. Abraham stayed in this house often during his time in Connecticut, watching after his nephew along with his sister, Ruth Baldwin Barlow. Abraham Dudley Baldwin as an adult resided in this house with his own family, and was largely engaged in local and state politics and agricultural pursuits. The Bradley-Baldwin House was restored a few years back, and looks amazing!

Reverend Richard and Lavinia Dey House // 1823

Richard Varick Dey (1801-1837) was a young divinity student from New York City, attending the Theological Seminary in New Brunswick, New Jersey, when he met Lavinia Agnes Scott (1805-1886). Dey was the son of prominent New York attorney Anthony Dey and Catharine Laidlie; Catherine’s father, the Rev. Archibald Laidlie, was the first minister called to preach in English in the Dutch Church in New York City. Richard and Lavinia fell in love and became engaged on December 27, 1820. However, Lavinia’s parents were opposed to Richard, and her father even asked Richard’s theology professors at Rutgers to try to discourage his pursuit of Lavinia. It did not work and they married in September 1822. After graduating from the Seminary in 1822, Richard was licensed by the Congregationalists and the young couple moved to Greenfield Hill, in Fairfield, Connecticut, where he preached from 1822-1829. Local history states that it was actually Lavinia who designed this house in 1823 for their family and oversaw the builders during its construction. The Federal style house stands out for its clear Dutch form with its roof projecting to create a recessed verandah, likely influenced by the couple’s New York/New Jersey upbringing.

Reverend Dey, Lavinia, and their children relocated to New York City, and Richard preached at a number of churches the before he died unexpectedly in 1837, leaving his 32-year-old widow with four young children. Lavinia remained in New York, where she served as the manager of The Society for the Relief of Poor Widows with Small Children for over 25 years. She never would remarry and died in 1886.

Pomeroy-Belden House // c.1758

This stunning gambrel-roofed Georgian manse is located on Bronson Road in Fairfield’s Greenfield Hill neighborhood, a well-preserved in the northern part of town with large historic homes on large lots. The Pomeroy-Belden House was built in about 1760 for Seth Pomeroy (1733-1770), the son of Seth Pomeroy Sr. (1706-1777) a gunsmith and soldier from Northampton, Massachusetts, who served in King George’s War, the French and Indian War, and the Revolutionary War (at nearly seventy years old). Seth Jr. graduated from Yale in 1753, and would accept the call as the minister of the Greenfield Hill Congregational Church from 1757 until his death in 1770. He had this stately house built for his family during his time as minister. After his death, the house was purchased by Captain David Hubbell who used it as a store until it was purchased by Reverend William Belden, who served as pastor of the Greenfield Hill Congregational Church from 1812-1821. The Georgian mansion features a central double-door entry with traditional door surround, later shingle siding and a gambrel, wood shingle roof punctuated by three small dormers.

Greenfield Hill Congregational Church // 1855

Local residents of northern Fairfield successfully petitioned the General Assembly to establish a Congregational church in 1725 as a new Northwest Parish, a distinct group from the Fairfield Congregational Church. Their first meeting house was erected just years later in 1727. A larger, more substantial meetinghouse was built in 1760. The area of Greenfield Hill has always been remote and more suburban, but became important in the late 18th century when Timothy Dwight became minister of the Greenfield Hill Congregational Church in 1783. Dwight would go on to become the eighth president of Yale College (1795–1817). With increased funds and affluent members, another church was built in 1850 from plans by esteemed architect Richard Upjohn, in the Gothic style. Sadly, just years after it was completed, a fire from a furnace inside destroyed the church. So again, they rebuilt in 1855 with the building we see today, sort of. Architect Alfred Nash furnished plans for the building which was more Italianate in design. The church would be modernized in the 1940s in the Colonial Revival style, from plans by local architect Cameron Clark, likely inspired by the collection of Colonial-era homes nearby, including his own home in Greenfield Hill. The church remains a visual anchor for the affluent neighborhood.

The Tower Cottage // 1880

Tower Cottage was built in 1880 and is one of the best examples of Queen Anne architecture in the town of Ridgefield, CT. The home was designed and built by Charles Betts Northrup, a carpenter and builder who grew up in town. The home was eventually occupied as a summer retreat for Maude Bouvier Davis, who would spend some summers at the house away from the big city. In Ridgefield, Maude was sometimes visited by her niece, Jackie Bouvier, later known as Jackie Kennedy Onassis, First Lady to President John F. Kennedy. Maude owned the property until 1972 and the home has been lovingly preserved since.

Peter Parley Schoolhouse // 1756

The Peter Parley Schoolhouse (also known as the West Lane Schoolhouse) in Ridgefield, CT, is an excellent example of a well-preserved one-room school building in Fairfield County. The little red schoolhouse was originally built in 1756 and either replaced or enlarged in the early 1800s. As Ridgefield in the early days was primarily an agricultural community, many children split their time either helping family on the farm or in school, with work almost always coming before education. The school is named for its most famous student, Samuel Griswold Goodrich. Goodrich went by the alias Peter Parley and was born in Ridgefield, attending the school between 1799-1803. He was a prolific writer, with over 170 books to his credit, and is believed by many to have written the first American textbooks. Samuel wrote about his experiences as a student there, giving locals and historians a look into early life in the town. In the early 1900s, the town consolidated schools and this building was closed. The town seemed to simply close the building and it saw some neglect over time until the Ridgefield Historical Society assumed a lease of the property, recently restoring it.

Bailey-Keeler House // c.1860

Lewis H. Bailey (1818-1899) was a local banker, merchant, and hotel proprietor in Ridgefield, Connecticut. He had this stunning Italianate Villa home built on Main Street before the American Civil War. Bailey was savvy in realizing the upcoming development boom in town as wealthy New Yorkers began to arrive in town to build summer houses to escape the cramped city living and polluted air, and he began to sell off land and develop streets in the village. To house some shorter-term summer residents, Bailey constructed and operated the old Bailey Inn on a lot adjacent to his own home. The inn was torn down in the 1920s as the town’s dynamic as a summer town began to change with more more year-round residency. The Italianate Villa is a lasting legacy of Bailey and his impact on the town. The home with its square tower and detached carriage house are in a great state of preservation and significantly contribute to the character of Main Street.

St. Stephen’s Episcopal Church // 1914

When Ridgefield, Connecticut was settled in 1708 by Europeans, there was only one Episcopal Church in the state, and the general assembly allowed dissenters their own churches so long as they continued to pay taxes to support the Congregational Church. Ridgefield’s first Episcopal church, St. Stephen’s was built in 1740 on land granted by the Proprietors who founded the town and laid out lots along the towns new Main Street. In 1776, St. Stephen’s minister, Epenetus Townsend, a Tory (loyal to the British), was ordered to leave town with his wife and five children when the Revolution picked up steam. He was appointed chaplain to a British regiment and in 1779, the battalion was ordered to Nova Scotia. En route by vessel, a severe storm arose and all passengers were lost. The church was taken over by the commissary department of the American Army. During the Battle of Ridgefield, British troops set it on fire as a statement to the townspeople. The church was replaced two more times until 1914 when the present building was constructed. The Colonial Revival church is absolutely stunning and built from plans by (unknown to me) architect Walter Kerr Rainsford. The rubblestone church is one of the most pleasing designs I have seen in Connecticut!

Seymour House // 1760

While this house appears to have been built in the mid-1800s as a Greek Revival home, it was actually built nearly a century earlier as one of the oldest extant properties on Main Street in Ridgefield, CT! Located on proprietors lot #20, the original building lots laid out for the new town of Ridgefield, this house appears to have been constructed in 1760 for Matthew Seymour (Seamore) and consisted of what is now the ell of the home (left side). Seymour operated one of the trade posts in town that engaged in trade with a nearby native Ramapo Tribe. The home was likely re-oriented and added onto with a more formal Greek Revival wing with its gable roof facing the street before the Civil War, a configuration it retains to this day.

Rev. Thomas Hawley House // 1713


This old Georgian house was built in 1713 on the Proprietors Lot 5, on Ridgefield’s Main Street. Constructed for the first minister of Ridgefield, the home was originally occupied by 25-year-old Reverend Thomas Hawley (1689-1738) not long after his graduation from Harvard in 1709. In addition to being minister of the newly formed Congregational Church, Hawley (also spelled Hauley) also served as school teacher and town clerk. The house employs Dutch Colonial detailing from the gambrel roof to the extended portico over the front door, common in the Dutch colonies in the Hudson River Valley in New York.