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Thomas Painter House, 1682

17th Century

This circa 1682 center chimney saltbox home of Thomas Painter (1695) was featured as an example of early New Haven, Connecticut architecture in Isham & Brown’s 1905 Early Connecticut. It is one of the oldest houses in Connecticut.

In 1959-1960, the house was removed, except for its Victorian wing, to the National Historic North Street site in Litchfield, the former home of Dr. Lyman Beecher and the birth site of Henry Ward Beecher and Harriet Beecher Stowe. It was painstakingly reconstructed at this location stone by stone and board by board. A gambrel service wing was added, while the Long Island Sound Dutch influenced sweep, or “kick” of its roof line and door hoods was retained. The color of the beaded siding replicated an original mulberry infused stain.

Entering the wide, for its time, front porch and double door, of note is the hand crafted staircase with twice curved balusters and scrim mortgage button. The building’s front windows are an early 18th century improvement. The post and beam framing and the public rooms’ flooring is oak and chestnut. The parlor’s beams were boxed at an early date and complemented with plaster, fine paneling and a corner cupboard.

In 1989, the kitchen was enlarged, and in 1997, the office was expanded to reflect the owners’ interests which are also seen in other rooms replete with collections, fine arts and family mementos.

The Tapping Reeve House, 1773 & Law School, 1784  

From 1774 to 1833 the Litchfield Law School attracted over 1000 young men from all over the Country to study law with Judge Tapping Reeve.  Reeve taught his first students in the home he built in 1774, but by 1784 the number of students had had outgrown the house and he built the law school building.  The home and law school, owned and operated by the Litchfield Historical Society. The award winning exhibition offers role-playing, hands-on areas, and interpretive exhibits allowing visitors the opportunity to explore timeless issues of travel, communication, education, and community.

18th Century

The Colonel Benjamin Tallmadge House, 1775


The Charles Butler aka Corner House, 1792


The Ozias Lewis House Garden, 1806


The Litchfield County Jail, 1812


The Phineas Miner Law Office, 1820


The George C. Woodruff House, 1829


The G. Morris Woodruff House, 1855


The Frederick A. P. Barnard House, 1886


The Kingsbury Bull House, 1939


A Litchfield Marcel Breuer House, 1954


The Tapping Reeve Meadow, 2017

This gracious, gambrel-roofed dwelling was built by Giles Kilbourne for Thomas Sheldon and purchased by Col. Benjamin Tallmadge in 1782. Tallmadge, a legendary figure in General Washington’s notorious spy ring, lived here until his death in 1817. The home is one of the finest High Georgian residences in the Litchfield Borough. Tallmadge enlarged the original dwelling with the addition of columned porticos on the north and south sides of the home lending and air of monumentality not exhibited by other 18th century structures in the Borough.

Sited on a prominent corner in the Borough, this house is a two story Federal structure with quoins at the corners, pedimented gable ends and a denticulated cornice oriented toward North and East Street. In 1813, Frederick Deming added the north wing with its giant order Tuscan columned portico similar to those found on the Tallmadge House across the street. The primary entrance of the original section is on the west side where the four panel door and small light transom are surrounded by a fluted pilaster frontispiece. Original features abound including a large walk-in fireplace in the keeping room with its stone hearth and working beehive ovens and a paneled dining room. An Olmstead-designed pocket garden and antique garden house (gazebo?) grace the north side of the property.

Garden Highlights: “Pocket” garden designed by Olmsted Bros.

19th Century

Complementing the architectural beauty of this stately 1806 home, is a beautifully designed garden. With an artistic eye toward color, texture and form, the harmonious perennial beds are interconnected to resemble interlocking puzzle pieces. The numerous plantings seem to share a dialogue by communicating with each other in individual beds as well as across facing garden beds. To create points of interest, pieces of contemporary sculpture are strategically placed throughout the landscape. Focusing on a specific color theme in each individual garden bed presents a juggling act throughout the growing season. This landscape design rises to the challenge effortlessly. One particular grouping flanks herbaceous peonies, lady’s mantle, yarrow and phlox with navy blue irises and an edge of midnight blue salvia. Shades of pink Oriental poppies mingle with Sarah Bernhardt peonies in just the right color combinations. Bold choices such as mingling the bright oranges of poppies with various pink perennials work in this landscape.

Garden Highlights: Features many rare specimens including collection of peonies, pool and outdoor sculpture garden, perennial gardens, old espaliered species and more.

The oldest public building in Litchfield, and one of the oldest penal facilities in the state, the Federal styled Litchfield Jail was built in 1812. The jail had a cell block added in 1846 and a three-story wing with additional cell blocks in 1900. In 1992 the state closed the jail as a penal facility; afterward it served for a short time as a rehabilitation center for women. In 2014 it was purchased by a private developer who proposed that it be reinvented for residential, retail and multipurpose use while preserving the historic character of the building. Following an arduous challenge by the Litchfield Historic Commission, the renovated jail today functions as a lively public building housing shops, condominiums, office space, a bakery and soon to be opened pub/restaurant where patrons will dine within an old, three-story cell block.

The tidy gray building at 35 South Street where attorney Phineas Miner practiced was built in 1820 in the Greek Revival style, an architectural style very popular in the country during the nineteenth century. It was used as the Bronson Family Store and later sold in 1905 to a civic-minded group who has owned and lovingly maintained it for over 110 years. The façade owes its elegance and symmetry to the influence of the ancient Greek temples and their imposing columned exteriors. Its fluted square posts, tall front door, and very large windows topped by and expressed frieze board, are all typical Greek Revival features.

Built in 1829 and purchased by George C. Woodruff in in 1842, this house remained in the Woodruff family for 137 years. The original structure was flanked by matching covered side porches with geometric latticework and frieze panels. A rear two-story addition dates to the late 19th century. In 1916, the south porch was removed and a two-story wing added with a single-story Tuscan covered veranda on the rear. At the same time, the original entrance was eliminated and replaced with a bay window.  Another rear addition was created for the staff in the early 1900’s. Since 2000, the current owners have continued with extensive restoration including renovation of the three-bay carriage house, transforming it into an entertaining area finished in reclaimed barn wood and complete with state-of-the-art kitchen, music system, blue stone patio and fountain.  

Garden Highlights: 20 year long development of landscape and gardens, including a rose garden, kitchen pocket garden, carriage house renovation with newly designed terrace and garden.

In 1855, the Major Moses Seymour saltbox-style residence (built in 1735) was demolished on this site to build the George M. Woodruff House. This home is the finest and most ambitious example of the Italianate villa style in the Litchfield Borough. The handsome well-preserved structure is three bays wide with broad overhanging eaves and a deep plain frieze. The shallow hip-roofed structure is crowned by a rectangular-windowed belvedere (cupola). Two-story octagonal-ended bays with four-over-four windows on the north and south elevations are unusual due to the diminishing second level feature. Of particular significance is the front porch supported by distinctive fluted columnar-like posts with bulbous bases atop pedestals. The frieze replicates the deep design on the main eave level.

Garden Highlights: 30 year long and continuing development of landscaping, flower gardens and pool landscaping.

This statuesque Colonial Revival home was built by Frederick Augustus Porter Barnard as a summer residence. Barnard was born with hereditary hearing loss and had a successful career teaching the hearing impaired, and was later president of Columbia University of NYC. In 1929, the owners embarked on an ambition renovation. The north elevation suggests that the original styling was in the Colonial Revival mode. The three-bay façade has a shallow vestibule and a fluted pilaster frontispiece and a wooden lunette transom with iron grill. Additional renovations have been made by the current owners including a magnificent master bedroom and bath suite, highly sophisticated décor and a stately garden facing the west.

Garden Highlights: Newly designed gardens by Glen Hillman including shade garden, perennial gardens, stone wall features and reproduction French trellises forming an allee on the west lawn terrace.

20th century

The Bull House is a gracious mid-20th century Colonial Revival estate situated on 11 acres and includes many diverse adaptations of a Federal styled home. Both the main entrance and the central garden entrance on the south are set with magnificent Federal Revival frontispieces.  The current owners undertook a major renovation to accommodate a growing family, while preserving precious historic detail. Major interior dividing walls were removed to create brighter, open interior spaces. Several recent past owners have meticulously restored the landscape, pool house and arbor to retain its original design.

Marcel Breuer, a leader in the architectural Mid-Century Modernist design movement, built this 10,000 square foot villa for a local family in 1954. It was constructed of steel framing elements and reinforced-concrete slabs. The upper level is on grade with the entrance and features a large open dining-living area space, service area and a large outdoor terrace with dance floor. The bush hammered fireplace is possibly Breuer’s most sculptural and iconic. The lower rooms were designed to accommodate their children and open to a private pool area.

21st Century

The six acres surrounding the Tapping Reeve House has been re-imagined – not as a strict interpretation of a time period, but rather with landscape elements that would have been found in Litchfield from the 18th to the 20th centuries.  The site features a children’s garden, a traditional post and beam pavilion, heirloom apple orchard, a chestnut nursery, a wet meadow, and stone walls.  The Meadow is designed to provide visitors with opportunities for learning, relaxation and reflection.  Meadow programs give visitors up-close and personal interactions with nature – not as passive bystanders, but as active participants who touch, smell, taste, learn new vocabulary and develop observational and listening skills.