The architecture of Greenport illustrates the village’s growth from its pre-Revolutionary beginnings through its heyday as a commercial whaling center into a modern-day working waterfront that serves locals and visitors alike.
After the Revolutionary War, the village was called Green Hill — named for its expansive marshland and a hill located near present-day Greenport Yacht and Ship Building. The hill was leveled at the turn of the century to fill in the marsh that would become the incorporated village.
Lacking the natural materials to make their own, residents relied on bricks shipped from Europe to build the foundation of the village’s earliest homes until the discovery of clay, according to local historian Carlos DeJesus.
Many buildings were even floated into Greenport, village historian Gail Horton said.
Today, Greenport’s historic district consists of 254 wood-framed structures, a mix of residential and commercial, laid out in a fan shape from the village’s Main Street waterfront business district.
Vernacular, Greek revival, Italianate, Queen Anne and Victorian styles were among the most popular home designs.
“The architecture of this village is fascinating,” Ms. Horton said. “You can walk around and really see the past in the housing. You can tell what people did for a living.”
Turn-of-the-century dwellings occupied by the working class are typically found on cross-streets near Carpenter Street. Most are small, simply designed homes sited close to the street on deep, narrow lots.
The village’s official jailhouse was also located on Carpenter Street. The jail was nicknamed the Greenlight Hotel because a green light was turned on out front when the jail was occupied. While no longer used in any official capacity, the brick building still stands at 232 Carpenter St.
Members of Greenport’s rising merchant class built their homes on Bay Avenue. They favored the Italianate style, which features decorative molding, often in a floral motif, and open front porches with tapered square columns.
Main Street was where wealthy captains constructed grand, impressive houses. At one point the road was called High Street or Captain’s Walk after the stately homes. It even held the name Murray Hill — a reference to the upscale Manhattan neighborhood.
An example of the upper-class-style house is the Ebenezer W. Case House at 527 Main St. Mr. Case resided there through the mid-1800s. The two-story house is a vintage Victorian with a side bay window and a double front door.
Sterling Street was also the site of prominent homes. Built in 1835, the waterfront residence at 162 Sterling was home to the president of New York City Fire Insurance Co. The house, set on spacious grounds, has several unique features, including a Palladian style window in the front gable and wood fanlight carving in the gable.
Many of the multi-room houses in the village were later transformed into bed-and-breakfasts.
Today, Greenport’s Historic Preservation Commission keeps a watchful eye on its oldest residences, and has even published a pamphlet, “Recommendations for Homeowners,” as a guide for protecting the historic integrity of the buildings.