11 Seminary Street Built by Ruluff Lawrence in 1810, this house boasts a center hall with a curving staircase and twin chimney masses that merge in the attic. Its front door was later remodeled in the Greek Revival Style.
12 Seminary Street Built on the site of 39 North Pleasant Street by Dr. Joseph Clark in 1793 and moved by Ruluff Lawrence in 1804.
15 Seminary Street Built by Ruluff Lawrence in 1808 on land purchased from Daniel Chipman. This house has the unusual feature also seen in 11 Seminary St. of twin chimney stacks merging in the attic into the single mass that penetrates the roof. The house has been divided down the center and altered accordingly.
21 Seminary Street Built in 1813 by Middlebury printer Timothy C. Strong, publisher of the Vermont Mirror, the Christian Herald, and the Christian Messenger.
23 Seminary Street Built in the first quarter of the nineteenth century for Samuel Bent, manufacturer of candles, starch, and wool cards.
26 Seminary Street Built about 1804 by William Baker for Loudon Case. At mid-century it was the residence of Joseph Dyar, Middlebury silversmith and clockmaker.
33 Seminary Street Former District 6 Schoolhouse, built in 1823 and converted into a residence in 1872. The doorway with its etched red Victorian glass originally came from 11 Washington Street.
39 Seminary Street "Springside." This is the site on which Daniel Chipman, a cousin of John, had his frame residence built in 1802 – 03 according to the designs of Samuel D. Coe. Chipman settled in Middlebury in 1794 to practice law. From 1798 onwards he frequently represented the town in the General Assembly, in 1813 and 1814 served as Speaker of the House, and in 1814 was elected to Congress. Early in the century he founded a law school, for which he built a three-story building across the street from his home in 1816. In 1818 the great house, reputedly the most beautiful in Middlebury, burned, and the Chipmans took up residence in the law school and later moved to another fine house Daniel had built in Ripton.
In 1832 Epaphrus Miller bought the Chipman site and in 1836 had the present structure built. Surrounded by broad lawns and a fine wrought iron fence, it sits prominently on the southern slope of the hill, a great brick mass with handsome Greek Revival details and porch. In 1853 the property was purchased by wealthy sheep merchant Sylvester B. Rockwell, who added wide sliding doors between the front and back parlors, red and blue Bohemian pressed glass around the door, and the wooden wing behind the house. Rockwell's granddaughter married Professor (and later President) Ezra Brainerd, and the home became the president's house between 1885 and 1907, with Monday evening faculty meetings held in the front parlor.
Besides its site, its grand rooms and fine woodwork, the house boasts a large kitchen fireplace with two ovens and a basement spring which served as a natural refrigerator and from which the property takes its name of "Springside."
42 Seminary Street It was on this site that Daniel Chipman built his three-story law school, to which he moved after the 1818 fire in his home. In 1827 the Female School Association purchased the building and fitted it up for the Female Seminary (from which the street took its name). A two-story wing was added three years later. In 1869 Charles Munroe bought the property and, according to conflicting accounts, variously razed, moved and remodeled portions of the Seminary complex to develop the property for his residence. In 1925 the Munroe house was enlarged and remodeled into the present Colonial Revival structure. The building served as the Congregational parsonage from 1946 to 1975.
Stonecrop Ledge (Seminary Street Extension) This lot was settled in 1784 by Stephen Goodrich, who built first a cabin and then (about 1797) a house on the site. In 1800 he deeded his house and fifty acres to Dr. William Bass, a young and soon-to-prosper physician. Here by 1812 Dr. Bass had built one of the most prestigious houses in Middleburv. Its broad western front with its Georgian central pediment, Palladian window, and grand fan-lighted doorway was designed to be seen from Washington Street; but its operative entrance was toward Seminary Street, from which it appeared to be a large version of the Federal Style townhouse. The mass of the house is heightened and rendered even more impressive by the high attic with its series of fine elliptical windows.
Within, this house is of the "townhouse" type, with an off-center entry and curving staircase. The walls of the principal rooms have been thickened to permit the paneled window recesses usually possible only with masonry and the fireplaces have mantles of varied and elegant Federal Style designs. Elements of the house relate so closely to the Congregational Church and the S. S. Phelps House on Main Street that it is inconceivable that this could be the work of anyone other than Lavius Fillmore. The house was later acquired by Prof. D. Gregory Means, who added the elaborate porch to the west front and the winterized back apartments.The stuccoed house across the street from Stonecrop Ledge, at 62 Seminary Street Extension, is reputedly a section of the Female Seminary moved from the Munroe House site and converted into a residence. If so, it is the only element of the three buildings in town occupied by the Seminary to be left standing.
East of the Seminary building, at 66 Seminary Street Extension, is the Asa Chapman House, built at the corner of Court and Washington Streets in 1800 as Erastus Hawley's harness shop. It was purchased by Chapman for use as a shop and then remodeled as a dwelling in the Greek Revival Style. It was moved to the present site to make way for the building of the Chittenden Bank on Court Square.
4 High Street This much added-to story-and-a-half dwelling was built about 1815 by Martin Wood.
8 High Street Built in 1815 by Rowland Hack, this simple two-story postcolonial house has received a later doorway with etched glass lights.
11 High Street In spite of its added dormer and porch, this house, built about 1810 by Josiah Stowell, is one of the best preserved Cape Cod houses in Middlebury. Behind its large and very complete old kitchen fireplace is a smoke chamber, above which climbs the tiny, steep staircase to the upper floor.
17 High Street Another interesting and well-preserved post-colonial house is this one begun as a one-story, center-chimney dwelling by house joiner Bela Sawyer in 1798. Later owners added a full second story, Greek Revival door surround, and back wing, but the south front of the house (toward Seminary Street) maintains a staunchly late eighteenth century scale and air.
18 High Street The story-and-a-half dwelling built by Nathaniel Ripley, one of Middlebury's early carpenters, about 1800.