I haven't stayed at Extended Stay in North Orlando but I have stayed at both Extended Stay Deluxe and Extended Stay America in the Seaworld Westwood Blvd area - actually stayed at Extended Stay America for several months while moving to Orlando. I know there are a couple in the Maitland area but I don't know about closer to Winter Park.
My thoughts -
I loved the staff at ESA/ESD - as a woman on her own I felt very safe where I was - the hotel has a main entrance - doors do not open to the outside - I liked this. Housekeeping was good - the hotel was clean and well maintained - problems fixed immediately. It was basic - no frills - toiletries minimal - the beds at ESD are more comfortable than the beds at ESA - thought the bed was fairly hard but I got used to it. The laundry facilities are good. For the price I paid it was great - if you stay for more than a month - you get a monthly rate which is very cheap. The breakfast at ESD was basic - bagels, muffins, orange drink and coffee. It was nice to have the cooktop at ESA - nice to be able to cook some meals in the room. All in all - my experience was very positive - the staff were really great - felt like "family" since I stayed there for so long. Wifi at ESD good - wifi as ESA was minimal so I always upgraded to the higher speed - $30/month extra charge but totally worth it. Free parking both places.
I wouldn't hesitate to recommend Extended Stay hotels in the future and would stay try them again if I needed an extended stay type hotel.