FAIRFIELD — Take a leisurely drive through the streets of Fairfield and Westport, which were one in early American history, and the influence of the region’s early families is visible in the street signs and on prominent buildings: Bulkley, Burr, Coley, Hull, Jennings, Meeker, Osborn, Sherwood, and Wakeman.

On the front of the antique colonial house at 825 Mill Hill Road in the Southport section of town is a plaque that identifies the house as built by David Sherwood circa 1857. Subsequent renovations have maintained the outer shell of the house, which looks much the same as it did in the mid-19th century, but the interior was completely transformed and bears no resemblance to a historic house. The last two owners did extensive work to this house modernizing and opening the floor plan.

Still, this house is steeped in history because of its attachment to the Sherwood family. A monument in the Old Burying Ground on Beach Road in Fairfield is dedicated to Thomas Sherwood (1586-1655) who, according to that monument, was “a founder of New England (and) a first settler of Fairfield.” According to the website for Sherwood Farm in Easton there were many noteworthy members of the Sherwood family, including the dwarf Charles Sherwood Stratton, better known to the world as P.T. Barnum’s Tom Thumb.

Following in the agricultural footsteps of Thomas Sherwood, who built the first grist mill in the Mill Plain section of Southport according to the website, were David Sherwood and his brother John who farmed the land 200 years later. Under the wooden plaque that identifies the house as that of David Sherwood there is a metal plaque that states this property is in the Historical and Architectural Survey of Fairfield as of July 1988, under the auspices of the Fairfield Historical Society and the Connecticut Historical Commission.

“One of the many Sherwood houses in this area, this house was built by farmer David Sherwood on land he acquired from his father, Hull Sherwood, in 1857,” the survey says, adding that the house was updated with “modern Italianate details and massing. Executed with rather square proportions, the house should be noted for the prominent brackets at the deep eaves, as well as the arched windows in the gable ends.

This 3,731-square-foot white house with black shutters sits on a 1.24-acre level property. A fieldstone wall sits along the front of the property. The Belgium block-lined driveway leads to the newer detached two-car garage, which has a second floor. At the covered entrance to the house the front door is topped with a rectangular transom that has leaded glass shaped like a fanlight.

Inside, there are three finished levels and wide-planked hardwood floors. As with many newer homes this house does not have a formal living room, which many people considered wasted space. Instead there is a smaller flexible-use room that can serve as a den, office, music room, or library. It has built-in bookshelves and one side of the glass double-sided gas-fueled fireplace that also opens into the formal dining room, which also has built-ins.

Real Estate Listings

The eat-in kitchen is so spacious that it comprises about 40 percent of the first floor. It has a center island/breakfast bar, Calacatta Gold marble counters, white ceramic subway tile backsplash, a hardwood floor, and high-end appliances including two Bosch dishwashers, a 48-inch Sub-Zero refrigerator, and a 48-inch Viking eight-burner cook top. Off the kitchen is a good-sized sun room, which has three walls of windows with plantation shutters, and French doors to the flagstone patio and backyard. This part of the house also has a large laundry room that doubles as a mudroom and has a counter space, cabinetry, a sink, and a half bath.

On the second floor the master bedroom suite features a walk-in closet and a marble bath with two separate vanities, a free-standing soaking tub, shower, and white subway tile backsplash. There are two more bedrooms and a full bath on this level. On the finished third level there are two more rooms and a full bath. One is a bedroom. The other can be used as a bedroom, if necessary. If not, it can be used for any number of purposes including an exercise room - as it is currently used, or an office, or the entire floor could serve as an au pair suite.

More Information


STYLE: Antique Colonial

ADDRESS: 825 Mill Hill Road

PRICE: $1,226,600


FEATURES: 1.24-acre level property, whole house generator, flagstone patio, insulated windows, some window treatments, professionally landscaped property, two irrigation systems, easy walk to Mill Hill Elementary School, minutes to Southport Village and its restaurants and shops, not far from Southport Harbor and train station, potting shed, detached two-car garage with a studio above, town approved site for pool and/or sport court, five bedrooms, three full and one half baths

SCHOOLS: Mill Hill Elementary, Roger Ludlowe Middle, Fairfield Ludlowe High School

ASSESSMENT: $886,340

MILL RATE: 26.59 mills

TAXES: $22,885

Outside, the property features mature specimen trees, perennials - including peonies, irises and hostas, and a large organic vegetable garden by Oliver Nurseries and Design Associates. There is an irrigation system for the whole yard and a separate irrigation system for the fenced vegetable garden. The property also has a town-approved site for pool and/or sport court.

For more information or to make an appointment to see the house contact JoAnne E. Fisher of William Pitt Sotheby’s International Realty at 203-858-0749 or jfisher@williampitt.com.