One thing to note here is that dropping a user in oracle will not release space from its tablespace. A tablespace takes its own space and it acts as a virtual storage space for database users. So dropping a user will create free space in that tablespace, which can then be used by another user of that tablespace.
To check the available Free space in all tablespaces use this query:
select tot.tablespace_name, tot.file_name, tot.bytes/1024/1024 size_mb, free.free_mb
from dba_data_files tot, (select file_id, sum(bytes/1024/1024) free_mb FROM dba_free_space free group by file_id) free
where tot.file_id=free.file_id
order by free.free_mb;
For reorganizing a tablespace, you will have to reorganize its contents ie, tables and indexes. The reorganizing will need to have double the space in your tablespace, as it will move tables and indexes into new blocks, but after reorganize, you can reclaim the space by resizing the tablespace datafiles.
To Move tables and indexes, first determine which objects are using your tablespace using dba_segments view and then move/rebuild those objects using these commands:
alter table TABLENAME move;
alter index INDEXNAME rebuild online;