Depending on your association by laws- you could possibly do a 4 month lease for summertime. Many people from Florida, come up to Gloucester for summer. I have sold many condos at The Heights of Cape Ann and Many buyers were people from Florida who come up here in summer to escape the hot southern heat.
If you and your association allow dogs, you will have a easy time renitng. Many people now own dogs and not all landlords allow pets.
Depending on location , condition and view you can get a very decent return .
Parking is important to have as well.
Micghele allison Elwell CBR
Certified Buyer Representative
224 Washington St
Gloucester, ma 01930
http://www.beangroup.com/search/?frm=agt&aid=775262 and let me know if you would like to schedule a showing to view any of these lovely properties!