Greenport’s historic architecture is a modern-day link to the village’s storied past. The buildings illustrate its progression from pre-Revolutionary roots through its commercial peak as a whaling hub into a modern-day working waterfront with a thriving tourism industry.
The historic district of the village contains 254 wood-framed structures. A bird’s-eye view shows that the buildings are not laid out in a traditional grid style, but rather in a fan-shaped design that spreads out into the residential neighborhoods from the waterfront business district on Main and Front streets.
Many of the homes date to the 1800s and reflect the social standing of their original occupants.
Members of Greenport’s merchant class built their homes on or near Bay Avenue (above). They favored the Italianate style, which features decorative molding, often in a floral motif, and open front porches with tapered square columns, according to the book “Greenport” by local historians Antonia Booth and Thomas Monsell.
The home at 168 Bay Ave. is characteristic of the Italianate style, with two open porches, the typical tapered square columns and a front door flanked by sidelights with an etched floral pattern.
Wealthy captains and businessmen selected Main Street to construct their grand, impressive houses, the book “Greenport” states. The Ebenezer W. Case House on Main Street (above) is an example of a 19th Century upper-class house in Greenport.
Today, Greenport Village’s Historic Preservation Commission keeps a watchful eye on its oldest residences and publishes “Recommendations for Homeowners,” containing guidelines aimed at protecting the historic integrity of the buildings.
The village Business Improvement District has also created a self-guided walking tour for visitors with a map that allows them to discover Greenport’s most noteworthy historic homes for themselves.
The tour materials can be accessed at greenportvillage.com.
There are several prominent houses along Sterling Street, which were also owned by wealth businessmen.
The above house on Sterling St., built in 1835, is among those featured in a pamphlet about historic village homes produced by the Greenport Business Improvement District.
That home sits on spacious waterfront grounds and has several unique features, including a Palladian style window and wooden fanlight carving in the front gable.