Click photos to enlarge.
Notes in italics from Hampshire and the Isle of Wight by Nikolaus Pevsner and David Lloyd (1967)
Yale University Press, New Haven and London. Other information is from Hampshire Treasures. 

KINGSGATE. C14 gateway and above it the church of St Swithun with small domestic late C15 or early C16 windows. Only the E window is of three lights (but so is the W window). The gate has two pedestrian entrances of the C18. ... The church has a single-framed roof ...

East Side. Kingsgate Street is very rewarding. ... No. 5, of c.1700, is of chequer brick and has raised brick surrounds with lugs to the windows. ... Again of the same time Nos. 8 to 9a, see the raised brickwork on the upper floor. Three pretty later doorcases, and also the most charming of the typical Winchester upper bows.
No.12, C18. Colour-washed stucco. Tall panels with rustications each side of projecting centre. Arched central door with plain fan and console keystone 

West Side. The Wykeham Arms. Circa 1760. Red brick with old tile mansard roof. Four attic dormers. Double doorway with large fanlight circa 1830.
Next, C20 front on possibly older building. Red brick with stone dressings. Stone mullioned casement windows. Projecting pediment with large wooden modillion cornice. Modern doorway.
Next house is of c.1700. Wooden cross windows.

C18. Red brick. Original double-bowed shop front. Modern first floor bow window.

No. 69 is Moberley's (a house of Winchester College). This is dated 1571. It is of brick with blue diaper and has two gables. One original five-light mullioned window remains on the ground floor. The doorcase with Tuscan columns belonged originally to the next house. 
Gable ends have 2-light C16 windows. C19 extension to right of two  storeys and attic.

1st: C17, but possibly of earlier date. Brick ground floor, overhanging timber-framed roughcast above. Tile hung gable end and old tiled roof. C19 alterations and gable with applied timbering.
2nd: C18. Plum brick with dark brick string course between floors. Painted brick dentil cornice. Old tile roof. Central arched door with simple fan.
3rd and 4th: C18. Plum-coloured brick walls, brick dentil cornice, and stucco blocking course with stone coping. Old tile roof. Two doors, one with doorcase of engaged Roman-Doric columns and entablature.

1st: C18. 3-storey. Red brick with grey brick string courses between floors, painted brick dentil cornice and parapet. Central, square, grey brick panel. Arched door with fanlight. Doorcase with open pediment.
2nd: C18. Red brick with burnt headers and string course on first floor. Old tile roof. Late C18 bow window on first floor with bracketed cornice and bead and reel ornament. 6-panel door with panelled reveals.
3rd: C18. Painted brick with old tile roof. Door case with reeded pilasters and brackets, cornice broken forward over brackets. Sash and casement windows in wide frames.

In Kingsgate Road, the continuation of Kingsgate Street: C17 houses. Red brick, with brick string course between floors, and grey brick panels. Old tile roof. Next house of red brick with dark headers. C.19 tripartite sash windows below, casement above.