Partially found my answer:
http://www.calgary.ca/PDA/LUPP/Pages/He ... #DHCresultResidences put in order from the earliest:
Edworthy House & Sandstone Quarry
5050 SPRUCE DR SW
1883
WILDWOOD
Rouleau House
141 18 AV SW
1885
MISSION
Major Stewart House
26 NEW ST SE
1885
INGLEWOOD
Knight House (Van Wort)
1036 8 AV SE
1890
INGLEWOOD
A.E. Cross House
1240 8 AV SE
1891
INGLEWOOD
Senator Lougheed Residence
707 13 AV SW
1891
BELTLINE
Costigan Residence
219 17 AV SW
1893
MISSION
Bow Valley Ranch House
15979 BOW BOTTOM TR SE
1896
FISH CREEK PARK
McHugh House
110 18 AV SW
1896
MISSION
Poplar Grove Ranch Homestead House (Demolished)
40 SPRINGBOROUGH BV SW
1896
SPRINGBANK HILL
Christy Ranch House
13616 30 ST NW
1898
SAGE HILL
Nimmons Residence
1827 14 ST SW
1898
BANKVIEW
Union Cemetery Caretaker's Cottage
3025 SPILLER RD SE
1900
MANCHESTER INDUSTRIAL