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Hillhouse Avenue Historic District

New Haven City, New Haven County, CT

The Hillhouse Avenue Historic District was listed on the National Register of Historic Places in 1985. Portions of the content on this web page were adapted from a copy of the original nomination documentation. []


The Hillhouse Avenue Historic District is located in New Haven, Connecticut, a medium-sized New England city located on the northern coast of Long Island Sound approximately 100 miles northeast of New York City. The Hillhouse Avenue Historic District includes 24 major structures on 18 acres of land lying roughly one-half mile north of the New Haven Green. All but one of these major structures were erected between 1800 and 1929 and contribute to the historical and/or architectural significance of the district.

The Hillhouse Avenue Historic District encompasses roughly two large city blocks flanked by four heavily trafficked thoroughfares: Whitney Avenue to the east, Trumbull Street to the south, Prospect Street to the west and Sachem Street to the north. The principal focus of the district is Hillhouse Avenue. Originally laid out in 1792 under the auspices of James Hillhouse in anticipation of the area's development as a fashionable, upper-class residential locus, the northern half of this extremely broad, quarter-mile long stately boulevard bisects the Hillhouse Avenue Historic District on a basically north/south axis.

The landscape in the Hillhouse Avenue Historic District rises gradually from Trumbull Street toward a prominent knoll overlooking the northern side of Sachem Street, which is currently dominated by Yale University's twentieth-century Pierson-Sage complex, dominated in turn by Philip Johnson's 1964 Kline Biology Tower. Near the mid-points of the lots fronting the eastern and western sides of Hillhouse Avenue, the landscape begins to slope gradually downward toward Whitney Avenue and Prospect Street respectively.

The Hillhouse Avenue Historic District's structures form an unusually well-preserved assemblage of major nineteenth and early twentieth-century revivalist and Picturesque architectural modes. Styles represented include Greek Revival, Italian Villa, High Victorian Gothic, Queen Anne, Richardsonian Romanesque, Neoclassical and Colonial Revival. The grand scale and siting of the majority of these buildings, in conjunction with the careful attention to proportion, massing and detailing exhibited in the design of their various components, clearly mark them as the works of professional architects. Most buildings are set well back from the street and each other on generous, well maintained lots; most Hillhouse Avenue lots continue to run the full depth of their respective blocks. Surviving landscape features, such as broad lawns and cast-iron fences set atop low-cut stone walls along much of Prospect Street and Whitney Avenue, help to maintain the Hillhouse Avenue Historic District's nineteenth- and early twentieth-century aura of gracious opulence.

Brick and stucco form the principal exterior finish materials for buildings in the district, although significant examples of buildings featuring exteriors executed in cut stone and wood are also present. A wide variety of decorative exterior features survive on district buildings, including prominent, classically derived, columned entry porticos; bracketed cornices, window sills, and pediments in cut stone or wood; and decorative cornice moldings. Late nineteenth-century brick buildings often feature significant examples of terra-cotta and/or polychromatic brick detailing on their exterior walls. When considered as a group, and because of the wealth of variation in massing, detailing and color, the Hillhouse Avenue Historic District's buildings provide the viewer with an unusually rich collage depicting the full range of development of high-style American residential architecture between the early nineteenth and early twentieth centuries.

Virtually all buildings retain the bulk of their exterior as well as interior historic fabric. Many exterior alterations were executed prior to 1935 and are generally not only compatible to a given structure's original design but in some cases are themselves significant representations of the work of important later architects, such as Henry Austin. In virtually all cases, the alterations contribute to the evolutionary character which typified development of the Hillhouse Avenue Historic District's architecture through the early decades of the twentieth century.

The Hillhouse Avenue Historic District has suffered a few notable losses to demolition, including the 1840 Benjamin Silliman Jr. House at 34 Hillhouse Avenue (demolished 1936 - now a vacant lot) and the 1862 Second Empire-style James M. Hoppin House at 47 Hillhouse Avenue (demolished 1941 - now a vacant lot). Significant new construction is limited to the Yale Computer Center and the addition designed by Edward Larrabee Barnes in 1977-79 at the rear of the Apthorp House and Norton House (52 and 56 Hillhouse Avenue). Built to house Yale University's School of Organization and Management, this modern steel and glass structure features a low-profile design which is highly sensitive to its historic setting.

With the exception of the Henry Farnam House (43 Hillhouse Avenue), Russell Chittenden House (83 Trumbull Street), William Lyon Phelps House (110 Whitney Avenue) and New Haven Colony Historical Society (114 Whitney Avenue), all buildings within the Hillhouse Avenue Historic District are currently utilized by Yale University for institutional purposes. Since 1937, the Farnam House has served as the residence of Yale's presidents. The Chittenden House is currently used as an apartment house, while the Phelps House provides commercial office space. The Historical Society building retains its original museum oriented usage. However, despite extensive usage conversion, especially on the part of Yale, the dominant nineteenth/early twentieth-century residential appearance of the Hillhouse Avenue Historic District has been preserved through adaptive reuse of structures in a manner compatible with their size and interior arrangements, by limiting the encroachment of parking facilities, and through a lack of extensive new construction.

The Hillhouse Avenue Historic District forms the surviving middle portion of a larger fashionable nineteenth-century residential neighborhood, the southern and northern portions of which were systematically redeveloped between the latter decades of the nineteenth century and the 1970s. With the exception of the Dana House and lot at 24 Hillhouse Avenue, the blocks flanking the entire southern half of Hillhouse Avenue were excluded from the district since the residences built here in the nineteenth century were demolished and replaced by later structures designed solely for institutional use. To the north, on the knoll which rises above the northern side of Sachem Street, stands Yale University's twentieth-century Pierson-Sage complex dominated by Philip Johnson's 1964 Kline Biology Tower. Formerly the site of James Abraham Hillhouse's expansive Sachem's Wood estate, the square flanked by this complex designed for institutional use fortunately remains open at its southern end, preserving the green space at the northern terminus of Hillhouse Avenue which fronted James A. Hillhouse's 1829 mansion prior to its demolition in 1942. The Hillhouse Avenue Historic District's eastern edge is visually defined by the change in scale, siting and/or usage which takes place between district buildings and those found along the eastern side of Whitney Avenue. The western boundary of the Hillhouse Avenue Historic District is defined by a similar transition which takes place along Prospect Street.


The Hillhouse Avenue Historic District encompasses the most complete and best-preserved contiguous array of high-style nineteenth- and early twentieth-century suburban villa architecture surviving in the City of New Haven. The Hillhouse Avenue Historic District also ranks as one of the finest extant examples of its type in the State of Connecticut. A high proportion of the buildings included within the Hillhouse Avenue Historic District stand as examples of the work of architects of national and local renown. The Hillhouse Avenue Historic District's development was both conceived and initiated under the auspices of James Hillhouse, one of the most prominent civic leaders and urban programmers in late eighteenth/early nineteenth-century New Haven.

Historical and Architectural Summary

James Hillhouse (1754-1832) was a well-educated man of means who travelled in the post-Revolutionary world of the movers and shakers of his day. Heavily involved in local real estate speculation, he eventually owned and fostered the initial modern development of vast tracts of land throughout the city. Known throughout the state as cagey, he was also highly active in politics at all levels. During the 1780s, he served as a representative for New Haven in the Connecticut General Assembly. In 1790, he was elected to the U.S. House of Representatives, a post which he continued to hold until his election to the U.S. Senate in 1796. "When Mr. Jefferson, after being elected President, withdrew from the presidency of that body, Mr. Hillhouse was made President pro tempore of that body."[l] In the tradition of the true eighteenth-century amateur, Hillhouse was also extremely active locally as an urban programmer and real estate developer.

The planning and initial development of the modern Hillhouse Avenue area is but one example of James Hillhouse's driving ambition to transform New Haven into one of the nation's most beautiful cities through personal involvement in both public and private improvement projects. For example, through his extensive planting of elm trees on the New Haven Green and nearby right-of-ways, he established the city's modern image as a bucolic community of tree-lined streets and parks that gave New Haven its nickname "the Elm City." In the late eighteenth century, it was Hillhouse who spearheaded the transformation of the New Haven Green from an undistinguished 17-acre reserve into a formally shaped urban square. He was also the driving force behind the establishment of Grove Street Cemetery, a "garden for the dead" incorporated in 1797 and believed to be the first corporately owned and maintained cemetery in the country.[2] Although maturation, disease and/or storms have claimed the elm trees originally set out by Hillhouse in many areas of the city, the character which he created for New Haven survives.

The genteel character of the Hillhouse Avenue Historic District was predestined by Hillhouse when he laid out the subdivision in 1792 along both sides of the majestic boulevard which today bears his name. Following the laying out of this street and the subdivision of the land along both its sides, Hillhouse immediately began to set out elms along the boulevard in anticipation of the lush green canopy for which the street would later gain great renown. However, further development in the area proceeded very slowly over the next several decades. The lack of rapid development was probably due in some measure to financial reverses suffered by Hillhouse and men of similar social and financial stature as a result of the Embargo of 1807 and the ensuing War of 1812.

In 1823, Hillhouse transferred title to his still-extensive holdings in the area to his son, the poet James Abraham Hillhouse (1789-1841), on the occasion of the younger Hillhouse's marriage to a wealthy New York City heiress. At the time of this transaction, only three houses were standing in the district.

James A. Hillhouse's efforts to further his father's goal of developing the area as a fashionable residential locus combining idyllic beauty with the convenience of metropolitan living were stimulated by the construction of the Farmington Canal, an enterprise which, not surprisingly, involved the Hillhouse family. Begun in 1825, the waterway traversed the family's subdivision on its way toward its terminus at New Haven Harbor. Though the canal itself failed to meet its commercial expectations, it did create a new era of optimism among members of New Haven's social and financial hierarchy; lot sales and the construction of houses in the Hillhouse subdivision picked up significantly after 1825. (A portion of the canal cut still borders the southwestern edge of the Hillhouse Avenue Historic District.)

While the concept and initial development of the Hillhouse subdivision were the product of James Hillhouse, the single most important factor in the specific architectural development of the district proved to be James Abraham Hillhouse's large mansion, Sachem's Wood. Built in 1829 atop the knoll rising above the northern side of Sachem Street, the house was one of the finest Grecian Villas in the state. Originally known as Highwood, this expansive and highly elegant structure situated on generous park-like grounds introduced the large villa house form that would come to dominate the district, and instantly became the standard for all subsequent development. The younger Hillhouse, an enthusiastic patron of architecture, continued to work closely with A.J. Davis, one of Sachem's Wood's designers, to plan and shape the appearance of the neighborhood until his death in 1841. It is hardly surprising, therefore, that most of the pre-1840 villas standing in the Hillhouse Avenue Historic District were designed by Davis and that, as a group, they form an important early record of Davis' development as one of the country's leading proponents of the Picturesque and villa house forms. Unfortunately, Sachem's Wood was demolished.

Davis was responsible for the Mary Prichard House, a stately two-story, three-bay-wide stuccoed brick Greek Revival style dwelling with a flat roof and slightly embellished Greek Corinthian-order front portico, built in 1836. His 1835 Elizabeth Apthorp House, with its bracketed overhanging eaves, elongated coupled fenestration, and bracketed window hoods, was described by Davis as an "Etruscan Villa," although its cubic massing, symmetry and flat-roofed front-entrance portico are strongly Greek Revival in character. The Aaron Skinner House, designed by Davis in 1830, is one of the most significant antebellum structures in the district. Highly similar in massing and style to Sachem's Wood, this elegant villa with its pedimented, giant Ionic-order portico, is a quintessential Grecian suburban villa featuring later additions designed by Henry Austin in 1859.

By the 1850s, the relatively chaste serenity of the Greek Revival mode had begun to give way to the more decorative Italianate style. One of the most significant Italianate residences in the Hillhouse Avenue Historic District is the well-preserved Pelatiah Perit House designed by Sidney Mason Stone in 1861. A relatively rare example of Stone's work, the basic box-like, symmetrical massing of this palazzo-form house is richly embellished with bold, classical frontispieces and projecting eaves elaborated with modillions and denticulated moldings. The more flamboyant bent of the Italianate is well-represented by the Graves-Dwight House. Built in 1862, this house is the most exuberant and picturesque in the Hillhouse Avenue Historic District, with its bold, classically inspired detailing and varied roof silhouette. The 1848-49 John P. Norton House designed by Henry Austin is perhaps the most studied example of the Italian-Villa form, featuring a projecting four-story front tower, arcaded front entry, and coupled semicircular-arch window openings. Austin's predilection toward exotic, oriental detailing applied to Italian villa house forms is well-represented by the plant-like front porch columns and a main cornice "...imitating the fringe of some lavish oriental canopy..." found on his 1849 James Dwight Dana House, which was individually listed on the National Register in 1966.[3]

Seven residences were constructed in the latter decades of the nineteenth century, the last period of substantial building activity in the district. While those structures fronting Trumbull Street are representative of the flamboyant eclecticism and picturesque massing of the Queen Anne style, those built on Hillhouse Avenue generally defer to the conservative restraint established by Davis' earlier villas. The 1884 Charles Henry Farnam House reflects more of an academic than eclectic approach in its design, placing it well within the conservative genre of Hillhouse Avenue. The street's conservative bent was reinforced in the twentieth century when the impressive Edwin Wheeler House (1884) and the great pile designed for Henry Farnam by Russell Sturgis, Jr. in 1871 were both remodelled by later owners in more restrained modes. The ca.1882 Russell Chittenden House, however, continues to retain virtually all of its original Queen Anne-style exterior features, and stands as an excellent and well-preserved example of the massing and detailing combinations which typify the style as it appears locally.

The last residence built in the Hillhouse Avenue Historic District prior the early decades of the twentieth century was the 1892 Henry Fowler English House, designed by Bruce Price in the restrained Neoclassical mode, marking the full-circle triumph of classicism. The handsome, classically inspired detailing of this expansive building's exterior is matched by its gracious and opulent interior. Like many other late nineteenth-century structures in the Hillhouse Avenue Historic District, the English House in its first floor rooms features rich panelling, marble mantels, parquet floors and elaborately detailed staircases. Both the 1908-09 William Lyon Phelps House and the 1929 New Haven Colony Historical Society (designed by J. Frederick Kelly), which front on Whitney Avenue, are well-designed and well-preserved examples of the Colonial Revival style which mark the end of the district's historic architectural development.

End Notes

  1. Edward E. Atwater, ed., History of the City of New Haven to the Present Time, p. 99.
  2. Elizabeth Mills Brown, New Haven; A Guide to Architecture and Urban Design, p. 128.
  3. Brown, New Haven: A Guide to Architecture and Urban Design, p. 138.


Atwater, Edward E., ed. History of the City of New Haven to the Present Time. New York: W.W. Munsell and Company, 1887.

Brown, Elizabeth Mills. New Haven: A Guide to Architecture and Urban Design. New Haven: Yale University Press, 1976.

Chittenden, Russel H. History of the Sheffield Scientific School. 2 vols. New Haven: Yale University Press, 1928.

Dana, Henrietta Frances. Hillhouse Avenue from 1809 to 1900. New Haven: Tuttle, Morehouse and Taylor Company, 1900, reprinted 1907.

Kelley, Brooks Mather. New Haven Heritage; An Area of Historic Houses on Hillhouse Avenue and Trumbull Street. New Haven: The New Haven Preservation Trust, 1974.

Maslen, John J. "Hillhouse Avenue: A Museum of American Nineteenth Century Architecture, MS. (Unpublished Senior Paper, Yale University), 1949. On file in Yale University Art Library.

Miller, Robert. "Hillhouse Avenue: The Buildings of New Haven, Series II, Number I." MS. 1966. On file at Yale University Art Library.

New Haven Architecture: Selections from the Historic American Buildings Survey, Number 9 Washington, D.C.: U.S. Department of the Interior/National Park Service, 1970.

"New Haven Assessors Records." Tax Lot Maps and Grand List, 1983-84. On file at the New Haven Assessors Office, Kennedy Mitchell Hall of Records, New Haven, CT.

New Haven Historic Resources Inventory, Phase I; Central New Haven. New Haven: The New Haven Preservation Trust, 1982.

"New Haven Land Records." 1730 to 1930. On file at the Town/City Clerks Office, Kennedy Mitchell Hall of Records, New Haven, CT.

J. Paul Loether, New Haven Preservation Trust, Mary McCahon, Architectural Historian, and John Hezan, National Register Coordinator, Hillhouse Avenue Historic District, New Have, CT, nomination document, 1984, National Park Service, National Register of Historic Places, Washington, D.C.

Nearby Neighborhoods

Street Names
Hillhouse Avenue • Prospect Street • Sachem Street • Temple Street • Trumbull Street • Whitney Avenue