The earliest owner of this property is listed in 1844 as Ham Voice. Montalieu Nesbitt, father of local politician Wally Nesbitt, owned the home in the 1940's. This Edwardian red brick single family home is a full 2-storey with attic. The front door is protected by an open verandah with tapered Doric posts on large cement piers.

Built in 1876 for James Canfield, this L-shaped full 2-storey white brick has a grey slate hip roof, with many small brackets. The off-centered double doors feature a new segmental etched glass transom. The windows have the original shutters. This home has a field stone foundation.

This home is a full 2-storey Edwardian with open verandah supported by Doric Pillars. This was the residence of Bernadette Smith, on of the first elected women Mayors in Canada. She entered a field dominated by men and was elected on Monday December 3, 1951 to become the first woman Mayor of Woodstock. She served 6 years as Mayor and 12 years as Alderman. Smith was instrumental in preserving the Old Town Hall, now the Woodstock Museum National Historic Site.

This residence was built in 1875 for Emma and Henry J. Finkle, parents of Judge Alexander Finkle. Judge Finkle was born in 1843 and passed the Law Society examination at the tender age of 17. He was admitted to the Bar in 1883, and was appointed Judge at Woodstock on the death of Judge D.S. McQueen. This Italianate Gothic full 2-storey is a buff brick single unit with attic and trunked hip roof. The gables, dormers and towers all have decorated vergeboards.

H.C. Barwich and D.J. Hughes are listed as the first buyers of this lot. James Gunn, proprietor of James Gunn Grocer at 405 Dundas, owned this Neo-Classical home in 1853. It is a symmetrical full 2-storey with painted brick. The bays have 6/6 double hung windows and decorated shutters. Tapered Doric pillars support an open new verandah and open balcony. Sidelights and transom flank a centered entrance. The foundation is cut stone.

This Italianate town house has paired brackets, segmented windows, double front doors and a uniquely-shaped verandah supported by Doric pillars. The offset section of the verandah would have allowed cooler air to circulate around those enjoying the band concerts held in Victoria Park.

The home at 99 Light is a magnificent Queen Anne house built by William L. MacKay who owned several early clothing stores. He was a noted horticulturist, specializing in peonies, and his gardens at this address were widely known. This full 2-storey wood-clad home has a hip roof with gables. A window in the stairwell has round, diamond and painted stained glass. There is also a stained glass window decorated with a pink flamingo between the chimney flues. There is an open verandah decorated with brackets and bric-a-brac and supported by Doric columns is topped by a small balcony.

77 Light was built in 1878 by James Hay Jr., noted industrialist, was one of the founders of the Board of Trade in 1878, Mayor of Woodstock 1893-1894, and the first citizen to install a telephone in his home as well as his business. The brick building that housed James Hay & Co. was at one time the largest furniture factory in Canada. In 1900, Hay designed and built a new house at 785 Dundas, and his son Thomas lived at 77 Light. There is a lamppost from the Vansittart Farm on the property. This Italianate style full 2-storey buff brick home on a cut field stone foundation has a decorative cornice with paired brackets and dentils. It later became the law office of George Calder, Q.C.

Built on what was originally Crown land, this symmetrical, full 2-storey with attic, cleaned red brick home was owned by the family of David and James White for almost 90 years. It has a trunked hip roof, centered dormer with vergeboard and paired brackets. The windows have decorative lintels and original shutters. The closed porch has double doors, teardrop windows, decorative posts and brackets. Note the soldier-style drip course basket weave above the central window and corbel brick ins to form pilasters. The central door is new, with a semi-circular transom. Paired Doric columns support the open porch.