This Edwardian building, formerly the New Dufferin Hotel, is a full 3-story red brick with a flat roof. It was purchased in 1917 by the Young Women's Christian Association for $7500. A campaign launched by the citizens of Woodstock raised $8000 to purchase furniture for the building, much of which was bought at the auction of the items belonging to the hotel. A fire nearly destroyed the building in 1934 when a wall that divided the YWCA form a feed company to the west burned through. Notable features are the decorative brickwork, patterned cornice and the drip mouldings above the windows. The YWCA and YMCA decided to amalgamate in the early 1980's, and moved to a new building at 808 Dundas. The Peel Street location was sold in 1985-1986 because the YM-YWCA could not afford to repair it to current standards. It has housed a variety of businesses since its sale.

This home is built on land owned by some of the earliest settlers of Woodstock, with Arthur Farmer and Henry de Blacquiere being listed as owners in 1853. This Gothic Revival home has a trunked hip gable roof above a 2-storey bay window, a central rectangular tower with triangular dormer, trifoil window and decorative corbel bricking. Note the finial. The small gable shaped hood with large brackets and interesting transom protects the doorway from the elements. Built in 1876, at the same time as New St. Paul's Anglican Church, it is still serving as the rectory for New St. Paul's Church.

Another de Blacquiere, Charles, originally owned the land where this home is located. This Edwardian style 2-storey brick home has a gable roof with skirt, lattice vergeboard, palladian window in the gable and a wide cornice. The beautiful shed roof open verandah features reeded Doric columns, turned balusters, a lattice skirt, dentils on the cornice and a pediment on the roof above the steps.

This Ontario Vernacular is an L-shaped 1 1/2-storey buff brick that now houses an apartment and commercial space. The gable roof has a delicate verge board with central pendant post. The complementing finial has been removed. There are paired 1/1 shuttered windows on the main floor. The first storey bay window is a replacement. The new bell roofed open porch supported by turned posts and balusters protect the door and rectangular transom. the foundation is brick to the ground.

Situated on land owned by some of the earliest settlers of Woodstock, such as Andrew Drew, Henry Vansittart, Peter de Bacquiere and Thomas J. Cottle, this Italianate 2-storey has buff brick, a trunked hip roof with two central flue chimneys and a deep white cornice, with singular small and large brackets. The beautiful open shed verandah has a circular entrance above the steps, with tapered Doric columns on wood pedestals, turned balusters and lattice skirt. Note the iron finial on the centre of the verandah roof. This home was built by the well known Woodstock construction business R. Bickerton and Co.

Situated on land originally owned by John and Sally Hatch, this Ontario cottage was owned at one time by William and Charles Canfield. It is a symmetrical square 1 1/2-storey red brick with a steep hip roof. The front gable has a decorative wooden sunburst in the peak. The central door is protected by an open porch with turned posts and balusters. The balcony has a central door in the gable. The shed roof side verandah is supported by turned posts and balusters.

Another residence situated on Hatch family land, this site was owned by three generations of the Hatch family; John, Edmund and Joseph. Both sides of the house remained under a single owner until 1926, when it went to separate owners. This Edwardian double house is a symmetrical square red brick full 2-storey. It has a trunked hip roof with front dormer, and larger windows for the front room. Doric Columns on wooden pedestals support the verandah. The home features a cut field stone foundation.

Constructed on land once owned by Andrew Ross, Sheriff of Oxford, this Italianate full 2-storey was owned by some of Woodstock's early notable citizens, such as Joseph Hatch, Joseph and William Peers and Henry Thomas Parker. Prominent businessman Vernon B. King owned this home in the 1940's. It has buff brick with quoins, and a trunked hip roof with wide cornice, dentils, and small paired brackets between larger paired brackets. The open porch with paired turned posts on wooden pedestals protects the door with an ellipse-shaped transom. Both the door and the transom have cut bevelled glass. A French door from the dining room leads to a side porch that is similar to the front porch but with single turned balusters.

John Hatch is listed as the owner of this land in 1854. It was owned by the White family for several years, and remained under Kerr ownership for decades. This Italianate 2-storey has buff brick with red brick quoins and a trunked hip roof with Neo-Classical pediment above the main entrance. The wide cornice has small brackets that end with larger paired brackets at the corners. Secured by chains, the flat hood porch protects the front entrance. There is a large semi-circular stained glass transom above the centre door. A French door leads from the dining room to the side verandah, which supports a small decorative balcony.

Yet another home situated on land owned by John and Sally Hatch, this residence remained in the family of James White, a prominent Woodstock businessman and owner of the John White Co., until 1949. This Neo-Classical cottage is a 1 1/2-storey buff brick home with a hip roof and centered dormer. The windows have wooden lintels and brackets supporting the sill. The three-panel double door on the storm porch features an interesting window shape in the door. The house has a field stone foundation. This home was built by David White, a prominent local contractor, in mid to late 19th century Woodstock.