South Shore Investment Property

Chicago's densest concentration of courtyard multifamily buildings, close to the lakefront.

Housing stock: Vintage courtyard walk-ups, three-flats and small apartment buildings, many still on original systems. Units are often occupied, so tenancy transfers with the building.

Strategies that fit: Buy and hold, BRRRR.

Worth knowing: Most deals here are multifamily rather than single-family. Occupied buildings mean the Chicago Residential Landlord and Tenant Ordinance applies from day one — worth understanding before you close.

Chicago neighborhood in Cook County, Illinois.