The North Main Street Historic District was listed on the National Register of Historic Places in 1986. Portions of the content on this web page were adapted from a copy of the original nomination document. 
The North Main Street Historic District is located in the northern central section of the village near the heavily travelled Montauk Highway (the South Fork's only east-west access road). The North Main Street Historic District contains a largely unaltered concentration of period residences along the northernmost stretch of the village's Main Street and the nearby Railroad Plaza with its handsome station and small commercial enclave (for a total number of twenty-four contributing buildings and two non-contributing buildings). The residences along North Main Street are generally modest in size, design, and detail. The buildings on the east side of the street sit on small village lots and have uniform setbacks; the dwellings on the west side of North Main Street occupy larger more generous parcels. North Main Street is lined with mature trees and the residences have well-maintained, landscaped lots. The Railroad Station Plaza is visible from North Main Street and forms a small commercial enclave around a small landscaped park and parking lot at the southern end of the district. The historic residential and commercial district is separated from the large Southampton Village Historic District to the south by an area of altered historic and modern residential buildings (on the southeast and southwest). Other non-historic buildings and undeveloped land surround the North Main Street Historic District on the northeast and northwest.
The North Main Street Historic District residences are all wood-framed and sheathed, and represent a wide range of construction dates (mid-eighteenth century up to 1910) and residential designs. These designs are based on the village's conservative vernacular building tradition as well as local interpretations of popular American architectural styles. The cobblestone passenger station is the centerpiece of the Railroad Plaza, which is surrounded by wood frame and masonry commercial buildings. All these buildings face the parking area and landscaped park in front of the railroad station, which creates a wide, unifying open space for this small commercial enclave.
Although a majority of the residences within the North Main Street Historic District date from the late nineteenth and early twentieth centuries and reflect the village's extensive turn-of-the-century (1900) development, three dwellings on North Main Street date from Southampton's early settlement period. North Main Street was the village's primary access route from the north during the settlement period and these dwellings recall the area's initial growth. The 1740 Bishop Residence at 325 North Main Street is the earliest building within the North Main Street Historic District and one of a small group of extant eighteenth century buildings in the village. The remarkably intact Bishop Residence retains numerous original and period details and finishes. The two other settlement era buildings have circa 1750 sections which were incorporated into mid-nineteenth century residences. Of these two, the Reeves Residence at 219 North Main Street is the most intact and retains its three-bay, two-story, side entrance plan with substantial wings, and a handsome Greek Revival style entrance. The remaining turn-of-the-century (1900) residences along North Main Street display a variety of period architectural designs and details. Most exhibit traditional conservative building forms (three- and five-bay, two-story plans) with an overlay of popular eclectic picturesque details (decorative porches, bracketing, and classically inspired entrances).
The handsome railroad station (with its cobblestone and oyster shell exterior, decorative brick trim, deep overhanging eaves with scroll brackets, and round-arch windows) is the primary architectural focus of the Railroad Plaza. The nearby warehouse at 280 Elm Street is a distinguished period commercial building in the village. Its substantial brick exterior and gambrel roof are unusual features for a period warehouse building on eastern Long Island and make an important contribution to the North Main Street Historic District's overall visual quality. The plaza's remaining wood frame buildings (freight depot and 1900 commercial building) enhance and contribute to the enclave's historic appearance.
The North Main Street Historic District is historically and architecturally significant as a small, cohesive, largely intact concentration of residences and commercial buildings which reflect Southampton's early settlement and extensive turn-of-the-century development from 1740 up to 1910. North Main Street is one of the oldest thoroughfares in the village and the area around it was settled during the eighteenth century. The Bishop Residence (in the North Main Street Historic District's northwest corner) and portions of two other residences date from the mid-eighteenth century when the North Main Street area was undeveloped and primarily agricultural. The area remained relatively rural up until the last half of the nineteenth century when the railroad linked Southampton with western Long Island and New York City and the village began attracting large numbers of summer visitors. As a result of its proximity to the railroad station and inland location away from the choice waterfront real estate, North Main Street developed into a cohesive turn-of-the-century (1900), primarily working-class residential and commercial neighborhood which served the community's burgeoning resort development. The North Main Street Historic District contains a largely intact collection of buildings exhibiting a wide range of residential designs which are based on the village's ongoing conservative building tradition and local interpretations of popular turn-of-the-century architectural styles. In addition, the North Main Street Historic District includes the nearby Railroad Plaza, with its distinctive cobblestone and oyster shell sheathed passenger station and small commercial enclave. The Railroad Plaza and North Main Street residences constitute a largely unaltered concentration of period residential and commercial buildings which recall the area's agrarian settlement and reflect the community's extensive turn-of-the-century resort development.
North Main Street is one of the oldest roads in the village and follows the path of Towne Street, which was laid out in 1648. From Southampton's mid-seventeenth century settlement up to the mid-nineteenth century, the community was primarily agricultural with fishing and shipping providing additional sources of income for the village's early economy. North Main Street was a well-travelled road during Southampton's settlement period linking the village with communities to the north and intersecting with Montauk Highway, a heavily travelled thoroughfare which runs the length of eastern Long Island's South Fork and is its primary east-west access route. As Southampton became an established farming community during the eighteenth century, a village center emerged along South Main Street near the northern end of Lake Agawam. In addition, homesteads were also established in the village's outlying undeveloped areas. North Main Street developed slowly during the eighteenth century and scattered farmsteads were established along its route; three buildings which date from this period are included with the North Main Street Historic District. The remarkably unaltered Bishop Residence (325 North Main Street) was built in 1740 and is the oldest building in the district. Its two-story, five-bay, center entrance and central chimney plan is representative of eastern Long Island's local settlement period building practices. In addition, 208 and 219 North Main Street, although enlarged during the mid-nineteenth century, also retain building sections which date to the mid-eighteenth century. With its two-story, three-bay, side entrance hall plan, 219 North Main Street is a particularly well-preserved example of a nineteenth-century Long Island farmhouse and its eighteenth-century wing and classically inspired main entrance further enhance its significance. The majority of buildings within the North Main Street Historic District date to the late nineteenth century and early twentieth century and reflect Southampton's rapid development as a fashionable vacation retreat. As compared with other historic residential areas within the community, the North Main Street dwellings are relatively modest in size and decorative detail. Numbers 305, 310, and 314 North Main Street are noteworthy examples of Victorian era residential architecture in the district. All are well-preserved and display local interpretations of Italianate and Stick style ornamentation including decorative porches, bracketing, and sheathings. As a result of its decorative sheathing and details, 310 North Main Street is a particularly fine example of a Stick style cottage within the village and its picturesque facade helps define the North Main Street Historic District's northern boundary.
In addition, several of the residences within the North Main Street Historic District are not only representative examples of period domestic design in the village but are also associated with prominent local families. Jagger family members settled along North Main Street during the late nineteenth century and six dwellings (244, 276, 281, 300, 305, and 310 North Main Street) within the North Main Street Historic District were built by various branches of the family. The Jagger family name appears on many of the early maps of eastern Long Island's South Fork and the family figured prominently in the settlement of the region. The Jagger family residences within the district range from the mid-nineteenth century Stick style cottage at 310 North Main Street, to the substantial Italianate style farmstead at 305 North Main Street, to the 1910 hipped-roof Foursquare house at 276 North Main Street. The various Jagger family residences have played an important role in the North Main Street Historic District's turn-of-the-century architectural development.
The cottages at 328 and 338 North Main Street are small yet representative examples of early twentieth century residential design in the village and display simplified Colonial Revival designs. Built in the early 1900's, distinctive roof shapes and porches are their most noteworthy design elements. Moreover, these cottages were designed by prominent local builder George Elliston, who became a successful building contractor whose primarily residential works are represented in many of Southampton's intact period neighborhoods. Number 338 North Main Street, with its distinctive cross-gambrel roof, was built by Elliston as his own home.
The majority of the North Main Street Historic District's early twentieth century buildings are situated near the railroad plaza. The most distinguished of these is the largely intact railroad station. Its picturesque eclectic design includes a variety of textures and details including oyster shell and stone walls, decorative brick trim, deep overhangs with scroll brackets, and tripartite windows with round-arched transoms. The handsome station is the centerpiece of the plaza and is the primary visual element within the North Main Street Historic District's small commercial enclave. Number 268 and 280 Elm Street define and enclose the plaza's eastern boundary and their relatively intact exteriors reinforce the enclave's overall period commercial appearance. Although built as a rail-side warehouse building, 268 Elm Street has a brick exterior, prominent gambrel roof and segmentally arched windows. Built in 1900, it is one of the North Main Street Historic District's and village's most distinguished historic commercial warehouses and, together with the surrounding plaza, reflects the community's thriving turn-of-the-century growth.
The North Main Street Historic District contains a cohesive collection of residential and commercial buildings which span Southampton's eighteenth century settlement through its extensive turn-of-the-century (1900) resort development. Unlike many other historic areas within the Southampton Village Multiple Resource Area, North Main Street reflects an important episode in the village's historic development, recalling the year-round working-class development which accompanied the community's transformation into a fashionable turn-of-the-century vacation retreat.
Main Street North • Powell Avenue