The Charles and Joseph Raymond Houses (38 and 37 N. Union St) were listed on the National Register of Historic Places in 1979. Text below was selected and adapted from a copy of the original nomination document. 
The Raymond Houses were built at the height of the Victorian period. These irregularly shaped stone and brick mansions face each other across North Union Street.
While the architect is not known, it is safe to assume that the same architect built both structures due to the many common features and decorative designs.
The Charles Raymond House (38 North Union Street) is the more elaborate of the two both in its exterior and interior features.
Rusticated stone forms the first story giving the structure a heavy and solid base. A stone belt course separates this base level from the 2nd story of brick. However, the heavy stone is used for lintels, sills and quoins on this level. A wide frieze and boxed cornice help to separate the roof level from the lower levels. The many roof shapes and their decorations give the Charles Raymond House its exuberant and complex appearance. Four articulated brick chimneys are located one on each side elevation and two to the rear of the roof. Two conical roofed towers topped with cast-iron finials also pierce the roof line, one at the southwest corner and one on the north elevation. A bell-shaped roof tops the small oriel window located in the northwest corner. A hipped-roofed dormer topped with a cast-iron cresting is located over the center doorway. Above this dormer at the apex of the roof is a decorative gable roof dormer. Cast-iron cresting runs along the top of this dormer and the central roof line. A gable roofed stone dormer is located to the south of the hipped roof former. An elaborate comma shaped stained glass window is located in this dormer.
Windows throughout this five bay by five bay house vary in size, shape and arrangement. The majority are 1 over 1 double hung sash in varying widths. However some tower windows are fixed rectangles with stained glass transoms. Stained glass plays an important part in the decoration of the Raymond house, only the use of carved and turned spindles is more prevalent and that many on the interior. However some of this spindle work can be seen in the treatment on the 2nd story porch located over the main door. The detailed main door is original however the present owners extended and enclosed the porch to form a cloak room, in 1975. The doors were moved from the inner entrance to the new porch entrance.
The Joseph Raymond House (37 North Union Street) is similar in design and decoration. The 1st floor is also rusticated stone and the 2nd story brick. A circular verandah lines the front, south and north elevations. The northeast corner tower is square with an irregular pyramidal roof. The southeast corner has a large circular tower with a conical roof. An elaborate balcony with wrought-iron balustrade and circular arch is located in a decorative dormer over the main door. This dormer is comparable to the comma window dormer in 38 North Union.
Decorative features of this structure include wooden spindle porch brackets, banister, and star and cross shaped panels on the towers.
The residence at 37 North Union Street has been altered very little since it was first built. Fixtures have been converted from gas to electricity, but the fixtures are, where possible, the originals. To enter this house, one passes through the porch to the vestibule which opens onto the hall. The vestibule is very small, but the floor is done in ceramic tiles, the walls are panelled. The interior door from the vestibule has a stained glass transom. The wood at the head of the door frame is carved with a leaf and flower motif. This same motif appears above windows and doors throughout the 1st floor of the house. Also throughout the 1st floor is the wainscot, of darkly stained, carved wood. The wood is probably oak, and the wainscot covers approximately five feet up the walls. Approximately 20 inches from the ceiling the walls are bounded by a 1 inch strip of wood. The floors are light wood, of 2 inch width, patterned horizontally and vertically against each other in the manner of parquet floors. The staircase confronts the visitor immediately upon entering from the vestibule, and the effect is overwhelming. One first feels the sturdiness of the heavy structure, box-like and surrounded by the ornate wainscoting, with large posts at the foot and at the turn, elaborately turned balusters supporting the handrail. One newel bears a carved monogram, the other newel shorter and supports a candelabra, once a gaslight, now converted to electricity. The ceiling above the staircase is faceted because of the turn in the stairs midway between floors. The cream colored plaster contrasts well with the dark wood. The bases of the 2nd floor newel posts extend below the ceiling line on the 1st floor, and are visible from the hall. Windows above the stairs are filled with vari-colored pieces of stained glass, and are shorter as the stairs ascend. The fireplace in the hall is off center, and its wooden face is not symmetrically designed, the pillars and shelves are on one side, having no partners on the other. The heaviness on one side which results may have been intended to counter-balance the effect of the off-center location of the fireplace in the room. To the right of the vestibule, the irregularity of the room caused by the tower like projection becomes a small retreat from the main part of the hall. It is further isolated, or made to give the impression of separateness, by the grille of ornately arranged spindles and bails, in the same wood as the wainscot and the staircase, which is inserted between the walls of the vestibule and the edge of the fireplace.
Between the hall and the parlor are dark wood doors which slide into the walls when not in use. The wood in the parlor is cherry. The wainscoting is identical to that in the hall. The fireplace here, as in the other rooms on the 1st floor, is equipped to burn either coal or wood. It is high and elaborately carved, with an inlay of pink and white ceramic tiles, some bearing small rosettes. Each fireplace is distinctive. The windows in this room are topped by transoms designed with flower abstracts in yellow, green, blue and rose tones. The windows are deep-set, and the ten inch sills are hinged. When lifted, the sill reveals louvered shutters, of the same dark wood as the wainscot, which are constructed to slide up into place over the window when shade is desired. Sliding doors also permit complete separation of the parlor from the living room. This room opens onto the dining room, the hall, and the porch. The door to the porch and the large square-headed windows in the bay all have transoms filled with colorful glass designs. The fireplace in this room is of brown and tan ceramic tiles with the rosette imprinted on some of them.
The sliding doors retreat into the walls to reveal the dining room to the right of the living room. Here too the windows are set in the bay, which spans the width of the room and is vaguely separated from the rest of the room by an arch across its entire length. The location of this arch which implies a wall without completely isolating the section of the room contained in the bay. The wainscot is continued in this room, identical to that in the other room. Set into the wall between the doors to the living room and the door to the butler's pantry is a china cupboard. The fireplace is off-center and, like that of the hall, is non-symmetrical to off-set the imbalance. It is carved wood and sports shelves, a mirror, and, on the side toward the center of the room, a small cupboard which makes this side "heavier" than the side by the windows. The ceramic tiles here are blue and white, with rosettes. As was previously mentioned, the doors and windows here, as elsewhere on the first floor, are headed by simplistic leaf and flower designs engraved on the frame. A strip of wood below the ceiling line also bounds the walls here, as we described in the hall.
The renovations done in this house occurred primarily in the rear of the house. The pantry became an office with little alteration except the creation of a door leading to the living room. Remodeling the kitchen to accommodate modern appliances also required little real change in the house. The size of the room, the location of windows and doors, the presence of the servant's stairway, a large closet, a "chimney corner," remain. The chimney corner was converted to a toilet, however, and the doorway to the stairs, which would lead to the second floor, was closed off. The stairs to the basement remain. Below the kitchen and approximately the same size is a room which at one time was equipped to serve as a summer kitchen. The walls are white-washed, the ceiling finished with board. Off this room are the nonfunctional remnants of a dumb-waiter which once carried food from this kitchen to the butler's pantry above, where it could be taken, still hot, to be served to the family in the dining room. Another room in the basement, to the front of the house beyond the area in which the dumb-waiter was located, was unfinished and contained bins for coal, and such necessary but unattractive facilities.
The interior of 38 North Union is similar to 37 North Union, however all features are on a much grander scale.
The fireplace in the 1st floor has stands in the corner behind the stairs. It is not large, but the ceramic tiles which face it are not simply oblongs and squares but are large tiles which bear the image of a minstrel approximately seventeen inches high, five inches wide. There is a minstrel, each with a different instrument, on either side of the fireplace. Next to the fireplace is a single sliding door of dark, carved wood, which leads to the dining room. The salon, living room and dining room all open onto the hall. Opposite the door to the dining room is a door leading into the tower, which contains a rounded vestibule. This vestibule contains two large, square headed windows with leaded glass-transoms, and, on its inside wall, a decorative, miniature oriel. On the inside of the house this oriel forms a semi-circular; marble-topped table in the turn of the stairs. The massive body of the staircase is paneled in the same wood as the wainscot, and under the stairs is a small door which once led through to the kitchen or up to the 2nd floor by way of the servant's staircase. Since remodeling called for the removal of this lower part of the staircase, the passage under the stairs was closed off and is now used for storage. The stairs are the sliding doors which lead to the parlor. The room is larger than that of 37 North Union Street, and in the doorways are very elaborate grilles. While the other house had only one grille, here there are several, not only on the 1st floor but on the 2nd as well. Each of the large doorways off the main hall is topped by a grille of variously arranged spindles and balls. The fireplaces, other than that already described in the hall, are of ceramic tiles as in 37 North Union, some imprinted with a rosette design. The shutters here are of dark wood and are louvered, but are hinged rather than concealed under the sills. Built into the small tower off the right corner of the living room is a rounded window seat. The windows in this cubby-hole can also be covered with their hinged shutters, on left open to the sun. The sliding doors between the rooms here are not solid wood, but their upper hall contains a very elaborate design of colorful leaded glass. A small extravagance but one of many.
The front vestibule of the house is entered into by narrow double doors. The floor of the vestibule is of inlaid ceramics, the side walls are mirrors -- very lavish, and very much more impressive than the simple wood and tile and single doors of the vestibule across the street. Another unique, rather extravagant feature is found in the large dining room. Here a slight bay projects onto the side porch. What appear to be floor to ceiling windows are actually doors which are not hinged but which slide up into the ceiling to allow passage between the dining room and porch. The step is still present on the inside of these windows. The Charles Raymond House is used as a restaurant today. The owner has maintained the structure in its original condition with only minor alterations to accommodate fire and safety regulations.
Associated with 38 North Union Street is brick and frame carriage house. Its slate covered hip roof has wooden cresting and a square louvered tower. A circular tower is located in the west elevation. The main door is circular arched and faces the mansion.
A door on the 2nd floor is located on the alley for the leading and storage of feed. The tower area is finished and was once used as an apartment, possible by servants. The carriage house is in poor shape and needs immediate roof and wall repair.
At the height of the Victorian period two brothers built mansions facing each other in the small community of Middletown. The Joseph Raymond House (37 North Union St.) was completed in 1883 and the Charles Raymond House (38 North Union St.) in 1891. Both houses are similar in plan and decoration, however the Charles Raymond House was constructed on a much grander scale, with more expensive and varied features.
The house at 37 North Union was built in 1889. The land on which it stands was 1st offered for rent, at 15 dollars per year, by the Emaus Orphans House. This institution was created by the will of George Fray, who died leaving property which included one hundred and twenty lots in Middletown. The income from his properties was to support the Emaus Orphans House. Lot number 148 in the Emaus Orphans House plan became what is now 37 North Union St. It was first leased in June 1872 for a period of 99 years at a rate of 15 dollars per year. The title to the land was acquired by Seymour Raymond, who died in 1885 leaving it to his wife, Anna Raymond. Anna kept the property in the family, selling to Joseph Raymond in 1892. It did not change hands again for 20 years; when Joseph Raymond sold it to Isaac Doutrich in 1912 it was valued at 8,900 dollars. The present owners and residents, Maurice Metzger and his wife, purchased the house in 1922. They have maintained it, making improvements when demanded, for modern heating and electricity and so on, and made very few alterations of the original plan.
The property on which the Charles Raymond House stands came into the Raymond family in 1888, when Charles Raymond built the house on this lot, which he had purchased for $2,300. Apparently the extravagance exemplified by this house extended to other matters as well since in 1896 the property was sold to Ben Nead, receiver for the Middletown National Bank, for the benefits of Charles Raymond's creditors. There were several liens against his property. The next purchaser was Redsecker Young, who bought the house in 1898 for $6,600. In the settlement of his estate in 1904 his attorney, Robert Snodgrass, sold the house to Simon Cameron Young for $7,500. At his death, Simon Cameron Young left the house to his 2 daughters, Emma & Eliza Young. The Middletown Farmers Trust had become the guardian of the estate of Emma Young, who had formally been adjudged a weak minded person, and it sold her "Half- interest, 1/2 right, title and interest to this 3 story brownstone and other building," to Herman B. Baum and his wife, Sara for $10,000.
Currently the property is owned by Alfred D. Pellegrini who operates the structure as a restaurant.
The Raymond Houses are fine examples of the elaborate decorative mode that the Victorian period Queen Anne style developed at its height of popularity. The 2 structures typify the variety of decoration and detail that was present in this style. While the decorative details of 37 North Union are elaborate and complex, the details of 38 N. Union are even more exaggerated and exuberant. The community of Middletown has quite a variety of large Victorian structures however the 2 Raymond houses are among the most elaborate and detailed.