High Ridge Manor // 1893

Edward Payson Dutton (1831–1923) was a prominent American book publisher who founded the E. P. Dutton bookselling company in 1852 in Boston, Massachusetts. The business sold fiction and non-fiction, and within a short time expanded into the selling of children’s literature. In 1864, he opened a branch office to sell books in New York City and in 1869 moved his company’s headquarters there and entered the book publishing business. The company did very well, allowing Edward and his wife, Julia the means to build this large summer “cottage” in Ridgefield, Connecticut to escape the rustle and bustle of New York City. The couple purchased the lot in 1893 and appear to have built it soon after. High Ridge Manor is a stunning example of the Queen Anne and Shingle styles of architecture with its asymmetrical plan, continuous shingle siding with rubblestone foundation and chimney, gambrel roof, and towers.

Lewis June House // 1865

The Lewis June House sits on North Salem Road in northern Ridgefield, Connecticut, and is one of the finest Second Empire style homes in this part of the state. The c.1865 home was built for Lewis June (1824-1888), who was in the circus business, and it replaced an earlier home on the site that burned. Lewis June was a partner in the June, Titus and Angevine & Co. Circus that as early as 1842 toured 85 towns in six states. The circus wintered in Ridgefield. Past owners have since found many horseshoes, largely of small horses, on the property, suggesting that June kept the circus’ horses and ponies on this property. The home has been preserved thoughtfully and was listed on the National Register of Historic Places in 1984.

David Scott House // 1714

One of the oldest extant houses in Ridgefield, Connecticut is this charmer, which was moved not once, but twice! The house was built for David Scott (1678-1760), an Irish-born resident of the town, who purchased one of the town’s original Main Street house lots which sat undeveloped. Scott had abandoned his wife, Mary in Ireland, and settled in Ridgefield, entering into a new relationship with Elizabeth St. John. A woman scorned, Mary unexpectedly arrived in America and filed suit against her husband, citing Elizabeth as the “pretended wife of David Scott.” A judge awarded Mary three acres of her husband’s land. David Scott and his second wife lived at this 1714 house until they moved in 1740. His property (which included two enslaved Africans) was sold to Vivus Dauchy, a Frenchman. In the 1920s, as the Scott House section of Main Street commercialized, the owners relocated this house to Catoonah Street, building a commercial block in the former location. After numerous other owners, the most recent owner, The Ridgefield Preservation Trust (now the Ridgefield Historical Society) put it to use as a new historical society headquarters, after saving the Colonial-era home from demolition for stores and a parking lot! It was relocated to its current site and has been meticulously restored.

David Bradley House // c.1803

According to a dated board in the attic, this house was built c.1803! The David Bradley House on Old South Road in Southport, Connecticut is a great example of a traditionally designed house that does not need all the bells and whistles to stand out! The house was owned for a number of years by David Bradley, who worked as the village’s postmaster. It was David who likely added the Gothic Revival gable with lancet window and a (since removed) front porch.

William W. Wakeman Mansion // c.1833

William Webb Wakeman was born in Southport, Connecticut on June 19, 1799, the son of Jesup Wakeman, an eminent citizen of the community. As a young man, William worked with his father in his commercial and trade enterprises. He acquired his own vessel early in his career, and gradually accumulated a line of trade vessels, sailing to New York, Savannah, Georgia and Galveston, Texas. By mid-century he was involved in the East Indian and China trade under the firm name of Wakeman, Dimon & Co. He built and owned a line of steamships during the late 50s, and was commissioned by the Federal government during the Civil War to transport troops and equipment. His massive Greek Revival mansion was built around 1833 on one of the largest house lots in the village, perched high on a hill overlooking the harbor. The three-bayed facade is framed by a two-story portico. Supported by four fluted columns, the capitals and entablature are similar to the “composed” order of Minard Lafever and the “composite” order of Asher Benjamin, popularized in the 1830s and 40s in their pattern books for architects and builders. After William died in 1869, it was likely his widow, Mary Catherine (who lived to be 99 years old, outliving all of her six children) who enlarged the home with massive two-story ells.

Hastings House // c.1941

Many neighborhoods in New England held on to historical revival styles even when the International style and Mid-Century Modern homes began to proliferate all across the region. Some owners (even today) prefer traditionally designed houses to blend into their surroundings and historical context. This charming gingerbread Tudor Revival style house in Fairfield is one of them! The Hastings House was built in 1941 and designed by the powerhouse design couple of Cameron Clark (architect) and Agnes Clark (landscape architect) who designed and renovated properties all over Fairfield. The house is notable for its use of stucco with half-timbering, steeply pitched roofline, red tile roof, and more Colonial-inspired door treatments.

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.

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.

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.

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.

Hawley House // c.1865

Located next to the Reverend Thomas Hawley House (last post), this gingerbread cottage on Ridgefield’s Main Street looks straight out of a fairy tale! The home appears to have been built around the Civil War (or a renovation of an earlier house) and blends Italianate and Gothic detailing elegantly under one roof. The home was built on land that was owned by the Hawley descendants and was occupied by a few members of the family until it sold out of Hawley ownership in the 20th century. The house was purchased in 2002 by Gregory and Valerie Jensen who restored the home. Mrs. Jensen is the founder of the Prospector Theatre, a non-profit cinema dedicated to providing a higher quality of life through meaningful employment to people with disabilities.

Czar Jones House // c.1787

Czar Jones (1789-1869), a woodworker and a justice of the peace, served in the War of 1812 and later was a partner in the local carriage manufacturing company in Ridgefield, CT. Jones bought a circa 1787 house on Main Street in 1818 and modernized it to serve as his family’s residence. The modest late-Georgian house was updated in the Federal style. Not long after Czar’s death (his only wife died 1851) the home was then purchased by New York City publisher, Albert H. Storer and his wife Sophie, the latter was the founder and first president of the local Ridgefield Garden Club. The couple divorced in 1915, and Sophie moved to Europe before remarrying and settling in California. The home that was intended as a summer getaway for the family, became Mr. Storer’s primary residence as he remained in Ridgefield with his son Francis, daughter-in-law, and grandchildren, until his death in 1933.

Rockwell House // c.1850

Built in 1850, likely as a late-Greek Revival or Italianate style home, this property on Main Street in Ridgefield was completely “modernized” in the 1880s in the Queen Anne style popular at the time. The home was originally built for Francis Asbury Rockwell (1818-1881), a tin-smith, wine-maker and inventor who married Mary Lee Everest, who also had deep roots in the community and was a daughter of a local Revolutionary War captain. The couple built a home on Main Street and raised their children there until Francis and Mary died in 1881 and 1883 respectively. The family home was inherited by their eldest son, Charles Lee Rockwell, who became the director of the First National Bank in town. Charles updated the house to give it the Queen Anne Victorian flair we see today.

King Mansion // 1894

After the American Revolution, Lt. Joshua King settled in Ridgefield and built the King Mansion in 1801, a Federal style home that commanded the Main Street lot. King was born in Bridgewater, Massachusetts and fought in the Revolutionary War near the border of Connecticut and New York. After the war, he settled in Ridgefield and married one of the most eligible bachelorettes in town Anne Ingersoll. Anne was the daughter of the Rev. Jonathan Ingersoll, pastor of the Congregational Church of Ridgefield. After a long life running a store and raising a family, Joshua died in 1839, a year after his wife. The mansion was inherited by their son Joshua Jr. until his death in 1887. In 1889, a fire destroyed much of the house. When it burned down, The New York Times described it as “the grandest old mansion in the village.” It was quickly replaced by the current house, modeled after the original but larger, which was placed much farther back from the road in the Colonial Revival style. Fire damaged the house again in the 1990s, and the present structure was restored and enlarged from 2002-2004, its HUGE!