On the north side of the village parking lot and north of the gazebo. Ireland House is the home of the Stirling Historical Society. The house was built in the early 1830s on the south side of Adams Street about 100 feet from its present location. The house was home to numerous Greenport working families many of whom rented from the property owners.

The house style is Greenport Vernacular, a common house form built from the 1750s. It is a simple small-scale half house with a plain façade, painted clapboard, a doorway with sidelight and transom and 6/6 pane windows. It is a half house because windows are on one side of the front door.

In 1973, Mr. and Mrs. Frederick Preston donated the house to the Stirling Historical Society and in 1976, the Society moved it to the present location at 319 Main Street.

The Society named the house after Margaret E. Ireland, a well known civic worker and an admired, colorful resident of Greenport. She was a newspaper correspondent for the NY Herald Tribune, the NY Journal American and local papers; a tireless fund raiser for Eastern Long Island Hospital and Burton Potter Post American Legion, and matron of Greenport Police Department. Ms. Ireland's grandparents lived in the house in the late 1800s and raised their family there. Later Ms. Ireland's parents, James and Margaret Grady, lived in the house and when Ms. Ireland returned to Greenport in 1918, she also took up residency with her children. She lived in the house until her death in 1962 at the age of about-83. Because Ms. Ireland said, "ladies never tell their age," the family cannot confirm her date of birth. Photo

Built by Charles Langton Corwin for the First National Bank after the bank received the first national bank charter on Long Island in March 1864. The bank is one of the last original brick structures and the only original of its period in this sector of Main Street. The second story, side and rear sections were added between 1897 and 1909. The brackets are cast iron; sills and keystones are granite. The first drive-up teller window on Eastern Long Island was added in 1958. Photo

This is one of the most ornamental commercial structures in the business district. It has an arched parapet with wide bracketing and dentil work along the cornice with wood lettering that spells Reeve's Building. Note the scalloped shingles and ornate false front at the roofline. The Freemasons met on the second floor for years before completing the Johnston Memorial Masonic Temple located at 430 Main Street in 1901. Photo

A fine Italianate brick store and key building in the heart of the commercial district, this is one of the few buildings of this type and vintage that were not lost to fire or random replacement. The first of three druggists to occupy the building was G. H. Corwin. A rear addition housed the first telephone exchange in Greenport in 1906 and in the 1920s, a speakeasy was situated on the second-floor rear. Photo

Over the years and even today, this building was most often used as a studio or art gallery. It was the gallery of famous American Impressionist artist Whitney Hubbard (1875-1965) whose works are shown in the Corcoran Gallery, Brooklyn Museum, Connecticut Academy of Fine Arts, the Atlanta Museum and numerous others. Photographers rented studio space from 1897 through the 1920's. Frank Hartley and Hugo Frey were among the other notable tenants. Photo

Manuel Claudio arrived in Greenport aboard the Portuguese whaler Neve in 1854. Upon retirement in 1870, he established a saloon on lower Main Street. He later acquired the present property at the Main Street Wharf and opened the restaurant and a hotel. Claudio's quickly became an integral part of the Greenport harborscape and has been operated by the Claudio family ever since. The building, on the National Historic Register since 1945, has a two-story enclosed porch and paneled door entries with spindled brackets. Inside is an ornate mirrored bar that Manuel salvaged from a New York Bowery hotel and installed in 1886. Photo

This site is symbolic of Greenport: Since 1827 when Main Street was laid out with the wharf at its foot, ship captains met, provisioned and transported people and products from this location. The main building complex facing Main Street consists of two joined stores and a separate shop that was formerly a coal storage building. The latter was moved by the Navy in WW II and used as a machine shop for boat repairs and construction. Over the years, Preston's has serviced and provisioned a large assortment of yachts, including those of the Vanderbilts and the Astors. Photo

The configuration of the marine railway in this yacht yard has remained relatively unchanged since its installation in the 1850s. Boats of up to 1000 tons can be hauled on it. In the early 1900s, members of the New York Yacht Club had their boats overhauled here and America Cup contenders recruited crew from the yard. During World War II, the yard employed 1200 employees who worked on the construction of minesweepers and landing craft. Photo

This was the village's first official jail; its predecessor was a tool shed behind the old village hall. The village lock-up was called The Greenlight Hotel because when occupied, a green light in front was turned on. Located in the historic commercial district, the jail stands out because of the barred window and all-brick exterior. The jail has three cells with pressed tin walls. It is no longer used in its official capacity. Photo

This location is an important introduction to the residential neighborhood that borders the village's commercial center. The house originally on the site was moved and only the rear kitchen wing was kept when the main Queen Anne house was built prior to 1897. John G. Champlin, grocer and dry goods, was an early owner of the 2 1/2-story house. There is a wrap-around porch and 5-window bay on the first story with tower above. Double-bracketed cornices are featured throughout. Photo

One of several large Bay Avenue homes built by the rising merchant class of Greenport. Italianate style with double bracketed cornice above two open front porches with tapered square columns. Porch columns have beveled corners that create illusion of arches; the single porch rail has decorative bracketing along the bottom. Eastern front door is flanked by sidelights with etched floral pattern. Photo

D. Kendrick, a ship carpenter, was the original owner of the house that is the oldest on this tour. This small Greek Revival gem is one of the few 1 1/2-story houses on a 2-story block. Photo

The house was originally owned by the Lyons, a prominent family in 19th century Greenport that included a lawyer and department store owner. The building is a 2-story Italianate with flat roof, double bracketed cornice and ornate widow's walk with arched windows on 4 sides. The porches have gingerbread railings, decorative brackets and square columns. Photo

One of the more original houses on the block. The front door is located directly below a center gable and has a gabled pediment with square columns. Long 2/2 windows flank the front door and are in the gable above the door. The house has irregular bracketing and 3/3 eyebrow windows on the front 2nd story. B Before heading one block north (left) to Central Avenue (Tuthill Street prior to 1897), take a moment to admire the bay view from the public dock at the end of Bay Avenue. Photo

One of the major houses on the street and originally part of the Tuthill estate. Remodeled in the mid-1890s. This is a flat-roofed 2 1/2-story house with a front porch that wraps to the east side. The porch has square column bases, paired brackets, decorative finials and spindle balustrade. The front door is Greek Revival. The first floor windows fronting the porch are 9/9 floor-to-ceiling. Photo

One of the few examples in Greenport of a 1 1/2-story half-house that developed into a full house. The first portion was built between 1838 and 1858; the west half was added between 1858 and 1873 when the A. Waynes family were residents. Photo

The house belonged to George Webb, a ship painter and dealer in paints and oils. It is a 2 1/2-story building with a 1 1/2-story eastern wing. A one story porch with turned columns on pedestals extends across the frontage of both wings. This is an excellent example of Italianate architecture that retains many notable features of the style. It has excellent bracketing and an articulated entablature over the main doorway and sidelights. Photo

On the southeast corner of Central and Carpenter is a smaller scaled, 1-story 3-bayed house built in Federal style near the beginning of the 1800s. This is one of Greenport's earliest surviving residences. Pilasters and a decorative pediment with dentiled cornices flank the centered front entry. The house has three small eyebrow windows of 12 panes each located under the eaves. Photo

The original 2-story house, built in the 1840s, is small and narrow and can be seen at the rear of the property. It was moved to give frontage room to the new cross-gabled house built in 1873. The houses are good examples of the simple Victorian vernacular for working class families of the time. Photo

This former boathouse was moved from the Mitchell property at the foot of Bay Avenue in 1971 and extensively renovated in the late 1990s. It is a 2-story house with a deep sloping gambrel roof. Large double doors with diamond windows face north and south. It is on a small lot and is one of the few residences on the west side of Carpenter since Main Street properties extended through to Carpenter. Photo

Sitting close to the street, this is one of several original saltbox homes on Carpenter Street. These small old houses are sited close to the street on deep narrow lots. They compliment and add to the diversity of architectural styles on the street. Photo

The corner complex includes 1885 Arnott's drug store (see stained glass on south side), Swain's Livery with carriage house and auto barn at east rear and a gabled house on the north frontage unchanged by commercial use. The drug store has heavily sculpted bracketing along the Italianate roofline. Photos

In 1864-65, this was a country store owned by Walter Havens. It is a fine example of a Cape Cod half-house. The doorway is Greek Revival with slender round pilasters. The eight-paneled door has bentwood sidelights with a matching transom above. Photo