I spend a bit of time debugging this with xnox. Here some of the
results:

# How to reproduce:
I setup a isc-dhcp-server with a fixed IP for my test rpi2 set to default/max 
lifetime of 120sec. The rpi2 was connected to the network with the 
isc-dhcp-server but unmodified otherwise. Once the pi2 connected and got an IP 
I switched the default IP to +1 and reloaded the isc-dhcp-server configuration. 
When the lease expired I could see the same as the OP - i.e. both IPs got 
removed.

# Related upstream bugs:
The patch from https://github.com/systemd/systemd/issues/5625 did not help with 
the issue

# Log
The full log of systemd-networkd is available here: 
http://paste.ubuntu.com/25686225/ - it was obtained by adding 
[Service]\nEnvironment=SYSTEMD_LOG_LEVEL=debug for the systemd-networkd.service.

The relevant lines:

Mar 14 21:02:52 localhost.localdomain systemd-networkd[7660]: eth0: Adding 
address: 192.168.1.124/24 (valid for 2min)
Mar 14 21:02:52 localhost.localdomain systemd-networkd[7660]: Sent message 
type=signal sender=n/a destination=n/a 
object=/org/freedesktop/network1/link/_33 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=16 
reply_cookie=0 error=n/a
Mar 14 21:02:52 localhost.localdomain systemd-networkd[7660]: Sent message 
type=signal sender=n/a destination=n/a object=/org/freedesktop/network1 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=17 
reply_cookie=0 error=n/a
Mar 14 21:02:52 localhost.localdomain systemd-timesyncd[995]: Network 
configuration changed, trying to establish connection.
Mar 14 21:02:52 localhost.localdomain systemd[1]: Starting Update resolvconf 
for networkd DNS...
Mar 14 21:02:56 localhost.localdomain systemd-networkd[7660]: NDISC: Sent 
Router Solicitation
Mar 14 21:03:00 localhost.localdomain systemd-networkd[7660]: NDISC: Sent 
Router Solicitation
Mar 14 21:03:04 localhost.localdomain systemd-networkd[7660]: NDISC: Invoking 
callback for 't'.
Mar 14 21:03:22 localhost.localdomain systemd[1]: Started Update resolvconf for 
networkd DNS.
Mar 14 21:03:51 localhost.localdomain systemd-networkd[7660]: DHCP CLIENT 
(0x22f0fd4b): REQUEST (renewing)
Mar 14 21:04:36 localhost.localdomain systemd-networkd[7660]: DHCP CLIENT 
(0x22f0fd4b): REQUEST (rebinding)
Mar 14 21:04:36 localhost.localdomain systemd-networkd[7660]: DHCP CLIENT 
(0x22f0fd4b): NAK: requested address is incorrect
Mar 14 21:04:36 localhost.localdomain systemd-networkd[7660]: DHCP CLIENT 
(0x4d15b90b): REBOOT in 0
Mar 14 21:04:36 localhost.localdomain systemd-networkd[7660]: DHCP CLIENT 
(0x4d15b90b): DISCOVER
Mar 14 21:04:36 localhost.localdomain systemd-networkd[7660]: DHCP CLIENT 
(0x4d15b90b): OFFER
Mar 14 21:04:36 localhost.localdomain systemd-networkd[7660]: DHCP CLIENT 
(0x4d15b90b): REQUEST (requesting)
Mar 14 21:04:36 localhost.localdomain systemd-networkd[7660]: DHCP CLIENT 
(0x4d15b90b): ACK
Mar 14 21:04:36 localhost.localdomain systemd-networkd[7660]: DHCP CLIENT 
(0x4d15b90b): lease expires in 1min 57s
Mar 14 21:04:36 localhost.localdomain systemd-networkd[7660]: DHCP CLIENT 
(0x4d15b90b): T2 expires in 1min 43s
Mar 14 21:04:36 localhost.localdomain systemd-networkd[7660]: DHCP CLIENT 
(0x4d15b90b): T1 expires in 1min
Mar 14 21:04:36 localhost.localdomain systemd-networkd[7660]: eth0: DHCPv4 
address 192.168.1.125/24
Mar 14 21:04:36 localhost.localdomain systemd-timesyncd[995]: Network 
configuration changed, trying to establish connection.
Mar 14 21:04:36 localhost.localdomain systemd-networkd[7660]: eth0: Updating 
address: 192.168.1.125/24 (valid for 2min)
Mar 14 21:04:36 localhost.localdomain systemd[1]: Starting Update resolvconf 
for networkd DNS...
Mar 14 21:04:52 localhost.localdomain systemd-networkd[7660]: eth0: Removing 
address: 192.168.1.125/24 (valid for 1min 44s)
Mar 14 21:04:52 localhost.localdomain systemd-networkd[7660]: eth0: Removing 
address: 192.168.1.124/24 (valid for 0)
Mar 14 21:04:52 localhost.localdomain systemd-networkd[7660]: Sent message 
type=signal sender=n/a destination=n/a 
object=/org/freedesktop/network1/link/_33 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=18 
reply_cookie=0 error=n/a
Mar 14 21:04:52 localhost.localdomain systemd-networkd[7660]: Sent message 
type=signal sender=n/a destination=n/a object=/org/freedesktop/network1 
interface=org.freedesktop.DBus.Properties member=PropertiesChanged cookie=19 
reply_cookie=0 error=n/a
Mar 14 21:04:52 localhost.localdomain systemd-timesyncd[995]: Network 
configuration changed, trying to establish connection.
Mar 14 21:05:06 localhost.localdomain systemd[1]: Started Update resolvconf for 
networkd DNS.

** Bug watch added: github.com/systemd/systemd/issues #5625
   https://github.com/systemd/systemd/issues/5625

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https://bugs.launchpad.net/bugs/1721223

Title:
  Networkd fail to set ip address between leases if ip address changes
  on UbuntuCore

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