C.B.
My stroller rocks! It sounds exactly like what you need. It is a Silver Cross. I got it as a gift, so I don't know the price, but it is honestly an amazing stroller. I get asked/complimented about it all the time. I'm a single mom, just did a trip to Disney and I could not do it without this stroller. My son is almost 4 and it's still ideal.
Characteristics:
1) Large basket underneath
2) Has a pouch for keys, etc in between the handles up high. It does not have a drink holder, but I put water bottles, sippy cups in here no problem.
3)Nice folding canopy
4)Large/fat sturdy tires that handle rough terrain amazingly well.
5)Has a 5 harness strap, at this point I don't use it but great when they are little.
6)It reclines, has an adjustable buckle. Snap the buckle and seat is all the way forward. Unsnap and it lays almost flat.
7)Its a freakin umbrella stroller! Step on 2 levers and "poof" folds flat! I can do this with a 45lb kid sleeping in one arm.
8)Has a handle on the side for easy carrying when its folded.
People are honestly amazed when they see me with this stroller. I know I sound a little nuts bragging about it, lol, but it is one of the best things I received and the only gift I am still using. When folded up it is larger then the cheap umbrella strollers, longer not really thicker. But it sounds like exactly what you need.
Hope that helps!