Your situation sounds a lot like mine!
I'm operating a Deere 790 on 2½ acres plus another three I'm field mowing for a neighbor. I've an acre of finished lawn (plus or minus), some field and some woods. There's also a 150 foot drive and parking pad to maintain and plow.
Originally, I had a Deere 670 which was a perfect fit (for my property, finished lawn and field, but not the neighbor's acreage), but I needed more PTO HP for a
chipper I was going to buy.
The
chipper never worked out, so I kind of wished I'd kept the 670 (it would have been paid for a year or so ago), although I really enjoy using the 790.
So, that said...
The first tractor I would look at and would probably fit your needs best would be a
Kubota B7510 or B7610. Other then the machines' weights, these two are equivalent to the Deere 670 (the 670 weighed more).
Power wise, these two are in the high teens or low twenties for engine HP. You can use 60" mowers and cutters behind either of these Kubota's. Some folks here will argue a 60" cutter is too big, but I did use one behind that 670 (16.5 PTO HP) with no problems. I just went slow or made a partial pass (not using the full width of the cutter) if necessary.
There are New Holland and Deere equivalents to the B7510/B7610 you can look at too. That's the size tractor that would fit you best, IMHO.