Hillside Historic District

Waterbury City, New Haven County, CT

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The Hillside Historic District was listed on the National Register of Historic Places in 1979. Portions of the content on this web page were adapted from a copy of the original nomination document. [‡]


Located just north of the Green in downtown Waterbury, the Hillside Historic District is a 116-acre residential area rising on a steep slope above the central business district. Bounded to the south by the downtown historic district along West Main Street, to the west by Willow Street and Cliff and Frederick Streets, and to the east by Cooke Street, it includes as its northern boundary the north side of Buckingham Street and Woodlawn Terrace. These bounds encompass all of Gaffney Place and Park Place, Prospect Street, First Avenue, Second Avenue, Central Avenue, Holmes Avenue, Linden Street, Mitchell Avenue, Kellogg Street, Glenridge Street, Cliff Street, Frederick Street, Trowbridge Street, and most of Hillside Avenue, Grove Street and Pine Street. The location and direction of the streets have evolved over 100 years into an interrupted orthogonal grid pattern. The area's residential buildings contribute to the Hillside Historic District's significance as excellent examples of the Greek Revival, Italianate, Gothic Revival, Queen Anne, Colonial Revival, Tudor Revival, Arts and Crafts, and Beaux-Arts inspired Classical Revival styles. The overwhelming majority of structures were built in the Queen Anne style. For the most part the non-contributing structures are office and apartment buildings of very recent construction. There is a small park on the northern side of Grove Avenue at its western end and few vacant lots. Two buildings in the Hillside Historic District are already individually listed on the National Register: Wilby High School and the Benedict-Miller House. The Hillside Historic District contains 398 contributing buildings (322 residences, 312 of which are considered contributing because their date, style, materials, and/or massing contribute to the architectural cohesiveness of the district; 1 contributing windmill; 7 contributing barns; and 105 detached garages, 78 of which are considered contributing "period" structures).

Since the character of the Hillside Historic District evolved over the 80 years from 1840 to 1920, there is a certain diversity of forms, but each individual streetscape is relatively uniform and predominantly Queen Anne in style. As one would expect, the grander houses are located on the upper streets, or what represented the uppermost streets during their era. Consequently, the residences on Hillside Avenue, upper Pine Street, Prospect Street, and Woodlawn Terrace, the homes of captains of industry, are much larger in scale and set back further from the street than those on Central Avenue and Holmes, First, and Second Streets, the homes of foremen and skilled craftsmen. In terms of style, the majority of streets (Cooke Street, Central Avenue, Holmes Avenue, Welton Place, Park Place, Cliff Street, Mitchell Avenue, Linden Street, First and Second Streets, Gaffney Place, Glen Ridge, and Hillside Avenue) are predominantly Queen Anne in style, with some Colonial Revival and Beaux-Arts structures. Woodlawn Terrace, Buckingham Street, Kellogg Street, and Pine Street have predominantly Arts and Crafts, Tudor Revival, and Colonial Revival structures. Prospect Street is the most heterogeneous street, with every style from Greek Revival to Colonial Revival represented. Grove Avenue is only slightly less diverse, while Willow Street and West Main Street are flanked by Queen Anne and Colonial Revival houses and Beaux-Arts apartment buildings.

The oldest houses surviving in the area were built in the Greek Revival style and are located on or near the two earliest streets: West Main Street and Cooke Street. Most of these are vernacular interpretations of the style and several were remodeled in the early 20th century (202 and 210 Prospect Street) and 3, 5, and 7 Cooke Street are excellent examples of the vernacular interpretation of this style. 174 and 180 Prospect Street, with their pronounced cornices and trabeated entries with transoms and sidelights accompanied by heavy cornices over the windows, are more refined examples of the Greek Revival style. The most elaborate example of the style is the Leavenworth House, moved approximately 150 feet north from its original West Main Street site when its underlying land was given to the YMCA and the house was given to the Girls' Club of Waterbury (c.1900). The flat-roofed three-bay house with side entry has been altered by the replacement of siding and some window sash, but has retained its elegant Corinthian-columned porch and heavy cornice.

The more romantic and picturesque styles, such as the Italianate and Gothic Revival, are not well represented numerically. However, the Gothic Revival Rose Hill at 63 Prospect Street is an excellent example of Henry Austin's mastery of the Gothic Cottage form. The building's stucco exterior is scored to emulate masonry, while the elaborate porch on its southern elevation is festooned with Gothic detailing. All windows are shaded by deep hood moldings of Gothic design, and steeply pitched gabled dormers enliven the roofline. The northern facade is more planar, with a porte cochere and enclosed porch.

The few Italianate houses are scattered throughout the Hillside Historic District, the best example being 36 Buckingham Street: it has a characteristic deep, flat cornice, and its planar facade is broken by a bay window, and vestiges of a removed tower. A more typical example is 125-9 Grove Avenue, which has retained its overhanging eaves and entry porches with scrolled balusters, curved brackets, and shafted columns resting on square, chamfered bases.

The single largest category of buildings erected during the era of aggressive eclecticism are those in the Queen Anne mode. The Hillside Historic District contains numerous excellent examples of this style. 45, 54, and 86 Hillside Avenue, all designed by the Palliser brothers between 1880 and 1883, are quintessential examples of the style with their asymmetrical massing, deep porches, varied polychromatic building materials, and picturesque rooflines. 37 First Avenue (1880) and 80 Central Avenue (1885) share juxtapositions of material, particularly terra-cotta banding with wooden half-timbering, that create vibrant textures. The western side of Holmes Avenue presents a very well-preserved Queen Anne streetscape, as does the southerly section of Central Avenue. The western end of Hillside Avenue contains a very impressive collection of well-designed residences whose walls and roofs flow together with a plastic fluidity that is rarely found in any Queen Anne design. The upper reaches of Central Avenue, Park Place, Gaffney Place, and Glen Ridge present excellent examples of more vernacular interpretations of the style.

The Hillside Historic District has an impressive collection of Colonial Revival and Tudor Revival houses as well. The best Colonial Revival houses can be found on Prospect Street, Woodlawn Terrace, Pine Street, and West Main Street. At 92 Prospect Street, the Martha Driggs House, designed by Murphy and Dana, is an excellent interpretation of the Georgian style. The Schlegel House at 270 West Main Street (1908-10) is a more ostentatious interpretation of the style, with deep, classically decorated porches, while the Hamilton home at 98 Woodlawn Terrace (1916), with its stylized Georgian entry, is a simpler, more academic interpretation of the style.

The Tudor mode was somewhat less popular in the district, but several excellent examples were built there in the first two decades of this century. 163 Woodlawn Terrace, with its asymmetrical massing, limestone hood moldings, and Tudor arched entry, is an excellent example of the style. 70 Hillside, with its H-shaped plan, Flemish gables, and exuberant detailing, is a good example of a Tudor Revival/Early Spanish Baroque amalgam. The Helen Chase home at 155 Grove Street, with its simple details designed by Cram, Ferguson and Goodhue, mimics an English country house. Several half-timber houses designed by Wilfred Griggs are found on Pine Street. 70 and 185 Pine Street share similar rectilinear timber patterns decorating large squarish, dormered residences, while 175 Pine Street has more elaborate curvilinear half-timbering atop a ground story of Flemish bond brick which has windows with limestone lintels.

There are also a few Arts and Crafts style buildings in the Hillside Historic District. The three best examples are found on Hillside Avenue, Prospect Street, and Pine Street. 129 Prospect Street is notable for its use of an arched entryway with extensive glass sidelights and slit windows, a projecting second story over a brick ground floor, and a recessed balcony with latticework topped by a textile frieze. 90 Pine Street is much more elaborate in massing, and its detailing is reminiscent of the work of Greene and Greene.

During the first decade of the early 20th century, several apartment buildings were built in the district. All were classically inspired and almost all of their facades follow the same basic parti: a central entry with classically derived decoration; upper stories delineated by distinctive belt courses; pairs of bow windows with decorated spandrels on each story; quoining; and heavy overhanging cornices. Two exceptions are 80 Willow Street and 144 Grove Street. The former is articulated with colossal pilasters and heavy keystones over flat-arched window openings and the latter is decorated with Adamesque details.

Institutional architecture comprises a small minority of Hillside's buildings. The few found in the Hillside Historic District date from the late 19th and early 20th centuries and were designed in traditional Classical Revival styles. The Driggs School on Woodlawn Terrace, built as part of Waterbury's earliest public school expansion in 1889, is a rather typical adaptation of the Georgian style to a long, horizontally massed facade. The Baptist Church on Grove Street, built 1915-17, replaced an earlier, smaller church destroyed by fire, and dominates its corner. The 1917 Classical Revival Christian Science Church on Holmes Street presents a formal contrast to the surrounding Queen Anne streetscape.

The Hillside Historic District now contains a college campus (a branch of the University of Connecticut) which consists of three noncontributing contemporary buildings on the same Hillside Avenue lot as the Benedict-Miller House, which serves as the school's administrative offices.

Most of the non-contributing structures in the Hillside Historic District were built after 1936 and are either modern low-rise offices or large apartment buildings. For the most part these are designed in variant modes of the International Style, with the exception of the Juvenile Court on Linden Street, which is Colonial Revival in style.


The Hillside Historic District is significant as a well-preserved 19th century neighborhood containing excellent examples of Greek Revival, Italianate, Gothic Revival, Queen Anne, Arts and Crafts, Tudor Revival, and Colonial Revival residences designed by locally and nationally prominent architects. The development in the area began c.1850, but its most dramatic growth occurred in the last quarter of the 19th century, when a large middle-class population built homes that created an architecturally cohesive district dominated by the Queen Anne style. The development of the area ceased by 1920.

Historical Background

Although Waterbury was settled in 1677, the Hillside area remained relatively undeveloped land until the early 19th century, coming into its own as the city's premier residential community c.1860. The residential development of the Hillside area paralleled the commercial development of the city, and the neighborhood traditionally housed a wide range of Waterbury's prosperous economic and social classes. The landscape of the upper regions of the district provided the area's most prosperous residents with impressive parcels on which to build imposing homes, while the area's proximity to the industrial area also made it a convenient and desirable location for Waterbury's growing working population to settle.

Throughout its period of growth, from c.1860 to World War II, Hillside served as home to Waterbury's powerful industrial and political leaders. Typical early residents of the lower Hillside included Scovill Merrill Buckingham, a founder of Scovill Manufacturing; brass manufacturer Israel Holmes; inventor Hiram Hayden, and Elisha Leavenworth, who was one of the last industrialists to live in a residential estate on Main Street.

The migration of Waterbury's wealthy above Rose Hill, an estate at the foot of the hill, was begun by D.F. Maltby, founder of Maltby and Morton Button Makers, who laid out tree-lined Hillside Avenue across the length of the hill in 1845 and built a house (demolished), located at the corner of Hillside Avenue and Prospect Street. With this construction, the uphill settlement of Hillside was established and the area's demographics slowly changed to include a wider range of residents. Rose Hill (1852), on lower Prospect, was alternately the home of members of the three most prominent manufacturing families in Waterbury, the Scovills, the Weltons, and the Chases. Infill properties were first occupied by lesser executives of the brass industry. Subsequently, lower Hillside's population included employees of the city's many new businesses spawned by the brass industry; bankers and real estate developers were typical residents and included A.F. Abbott, Secretary of the City Savings Bank and Building Association, and real estate entrepreneur C.C. Horn. The upper section of the Hillside district, however, was still dominated by industrialist families, including the Haydens, the Maltbys, and the Weltons, who had located along Prospect Street and Grove Street. The (1879) Queen Anne style mansion of brass industrialist Charles Benedict, president of Benedict and Burnham, situated on Hillside Avenue at the top of First Avenue, set the tone for the many imposing residences built thereafter, and established Hillside Avenue's role as a distinct boundary between the mansions and simpler houses of the neighborhood to the south.

Through 1880, Hillside's population gradually increased. The area's c.1868 residents, who were primarily pinmakers, bookkeepers, clockmakers, generally employed or supervised by the wealthy who lived above them, were, by 1879, joined by neighbors who provided services, such as physicians, dentists, travel agents, insurance agents, bankers, teachers, and butchers. From about 1880 to 1895, however, the population increase was more dramatic when several property owners, such as S.J. Holmes and Charles Mitchell, subdivided land in response to the tremendous demand for housing created by the blossoming brass industry.

After 1900, development in the Hillside area slowed. Single-family development was primarily restricted to the building of larger homes or estates on upper Hillside, and homes for the middle-class consisted of Beaux Arts apartment buildings situated in the vicinity of Hillside's southern boundaries. Wealthy industrialists such as Chauncy P. Goss and his sons, Edward and John, Scovill Manufacturing executives, continued to build large residences in upper Hillside along Pine Street and Hillside Avenue.

By World War I, Hillside was much as it appears today. Hillside was a thriving community until, according to area residents, it began to decline about 1960 when the middle class began moving out to the suburbs away from the noise and crime of the city. Recently, Hillside has experienced a resurgence, becoming popular again both as housing for Waterbury's downtown employees and as professional offices.

Architectural Significance

Architecturally, the Hillside area is a well-preserved neighborhood presenting a cohesive image. If contains excellent examples of all levels of interpretation of the various architectural modes from c.1850-1930. Most buildings constructed were in the Queen Anne mode, creating lively and vibrant streetscapes of modest-sized houses that are subordinate to the vast residences of wealthy industrialists and financiers on the upper third of the Hillside Historic District.

During the 1830s, 40s, and 50s, development in Waterbury was focused on the Green to the south. The few Greek Revival houses that were built in the area were located on the fringes of the district, West Main Street, Cooke Street, and Prospect Street. Those that have survived are good examples of the style. The best example, the Leavenworth House, was moved c.1900 as part of the family's bequest of its Main Street land to the local Girls' Club, but it has retained its basic form and Corinthian-columned porch. It is surrounded by Queen Anne and Beaux-Arts style buildings and stands as a reminder of the original character of the northern side of the now-commercial Waterbury Green.

Italianate, Gothic Revival, and other picturesque mode houses are few in number, but are good examples of their style. There were few houses on the hill during this period and most of those were large estates that were replaced by more intensive development during the post-Civil War era. The surviving houses are either altered, such as the Morton House at 36 Buckingham Street, or excellent examples, such as "Rose Hill" at 63 Prospect Street. Built in 1852 for industrialist W.H. Scoville, who lived there for only six months, "Rose Hill" is a quintessential Gothic Cottage with steep-pitched dormers, heavy hood moldings, and compact plan. The house was designed for Scoville by New Haven-based Henry Austin, one of the country's prominent designers of the romantic styles. The best Italianate example, the Morton House (c.1845), has overhanging bracketed eaves. It was once adorned with a tower on its western elevation which was removed before the turn of the century.

The single largest category of Victorian buildings in the Hillside Historic District are those built in the Queen Anne mode, reflecting Waterbury's exuberant and ostentatious rise to fame as an important industrial city during the last three decades of the 19th century. The number of buildings in the Hillside area was greatly increased between 1875 and 1900. The Queen Anne facades feature elegant combinations of stone and brickwork (or shingles), half-timbering, walls of casement windows, and Tudor chimney groups. A similar complexity was found in the interior spaces. A plan of irregularly shaped rooms was focused around a massive fireplace and elaborate open staircase. These were often combined in a characteristic living hall. The Hillside survey district includes three houses, 32, 54, and 86 Hillside Avenue, all designed by the Palliser brothers between 1880 and 1883, that are among the best examples of their mode in the state. The Pallisers, English builders who came to Bridgeport in 1873, gained enormous fame through their pattern books devoted to Queen Anne designs. The Benedict-Miller House, 32 Hillside Avenue, is already listed on the National Register (1981). Its neighbor to the west was built for Mary Mitchell by her brother, Charles Benedict, while N.J. Welton, a financier and engineer, commissioned his Palliser house in 1883. All of these houses were designed just as the firm began working in the Queen Anne mode; nevertheless, they are fully realized examples of the style and are excellent expressions of the vitality of the Gilded Age in Waterbury. There are other Queen Anne Houses that rival the Pallisers' work on a smaller scale: 30 First Avenue and 80 Central Avenue are equally dynamic in massing, while their monochromatic brick surfaces are enlivened by mousetooth courses and terra-cotta panels. The western sides of Holmes Avenue and Central Avenue, laid out in the late 1880s, are virtually unscathed Queen Anne streetscapes. The northern end of Central Avenue, built on a speculative basis by developer Frederick B. Rice, is an excellent example of more vernacular interpretation of the style. The western end of Hillside Avenue contains an impressive collection of well-designed residences whose walls and roofs flow with a plasticity that is rarely found in any Queen Anne design.

During the first three decades of the 20th century, Waterbury's prominence as an industrial city continued and the wealthy continued to build large, often architect-designed, houses along the top of the hill. Buildings were designed in several academically correct revival styles. 92 Prospect Street, designed for Martha Driggs by Colonial specialists Murphy and Dana of New York, is an excellent interpretation of the mid-18th century Georgian mode. At 270 West Main Street, the Schlegel house (1908-1910) is an ostentatious interpretation of the mode. The Hamilton home (1916) at 98 Woodlawn Terrace is an academic interpretation of the style by Wilfred Griggs, a local architect who was trained at Columbia University.

The Tudor mode was popular among the wealthiest classes because of its association with a manorial past and Anglo-Saxon heritage. The best example of this style is 163 Woodlawn Terrace, designed by Taylor and Levi, while the John Goss house at 70 Hillside is an equally excellent example of the late Tudor Revival/Early English baroque style. 155 Grove Street, designed for Helen Chase by Cram, Ferguson and Goodhue, also echoes a similar English influence. Several more half-timber houses were designed by local architect Wilfred Griggs, including the Marjorie Hayden House at 70 Pine Street. It is in near perfect condition and is an excellent example of the style.

There are few Arts and Crafts style houses in the Hillside Historic District; however, those built are good examples of the style and include 121 Hillside Avenue and 90 Pine Street. The Frisbie House, by Davis and Brooks, at 129 Prospect Street, with its subtle use of various materials, is an excellent example of the style. From 1900 to 1910, several apartment buildings were built in the area. All are classically inspired, the finest being "The Carroll" at 88 Willow Street. They were described as being among the best in New England.

By the end of World War I, almost every building lot was occupied and very few buildings were erected in the district. However, two apartment buildings were constructed on Grove Street; the larger of the two, the "Watorian," was built in 1923 in a severe adaptation of the Adamesque mode. During the 1950s and 60s, several major houses on Hillside Avenue were lost and were replaced by large high-rises.


Anderson, Joseph (ed.). The Town and City of Waterbury, Connecticut. 3 vols. New Haven: Price and Lee, 1896.

Pape, William J. (ed). History of Waterbury and the Naugatuck Valley. 3 vols. Chicago-New York: S.J. Clarke, 1918.

Waterbury CETA Program and Office of Community Development, Waterbury Victorian, The Hillside District nd.

Maps and Views

Bailey, O. K. View of the City of Waterbury. Milwaukee, 1876.

Beer, F. W. Plan of the City of Waterbury. New York, 1868.

Hopkins, G. M. Atlas of the City of Waterbury. Philadelphia, 1879.

Miller, D. L. Atlas of the City of Waterbury. Philadelphia, 1896.

Sanborn-Perris Map Company. Waterbury, New Haven County, Connecticut. New York, 1890.

‡ Steven Bedford & Nora Lucas, Historic Neighborhood Preservation Program, Stamford, CT and John Herzan, editor, Connecticut Historical Commission, Hillside Historic District, Waterbury Connecticut, nomination document, 1987, National Park Service, National Register of Historic Places, Washington, D.C.

Nearby Neighborhoods

Street Names
1st Avenue • 2nd Avenue • Buckingham Street • Central Avenue • Cliff Street • Cooke Street • Frederick Street • Gaffney Place • Glenridge Street • Grove Street • Hillside Avenue • Holmes Avenue • Kellogg Street • Linden Street • Main Street North • Main Street West • Mitchell Avenue • Park Place • Pine Street • Prospect Street • Ridgewood Street • Trowbridge Street • Welton Place • Willow Street • Woodlawn Terrace

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