Strategy of the European Union in efficient energy usage demands to have a higher proportion of renewable energy in the energy market. Since heat pumps are considered to be one of the most efficient heating and cooling systems, they will play an important role in the energy consumption reduction in buildings aimed to meet the target of nearly zero energy buildings set out in the EU Directive 2010/31/EU. Unfortunately, the declared heat pump Coefficient of Performance (COP) corresponds to a certain outdoor temperature (+7 °C), therefore different climate conditions, building characteristics and settings result in different COP values during the year. The aim of this research is to investigate the Seasonal Performance factor (SPF) values of air-to-water heat pump which better characterize the effectiveness of heat pump in a longer selected period of time, especially during the winter season, in different types of residential buildings in Latvian climate conditions. Latvia has four pronounced seasons of near-equal length. Winter starts in mid-December and lasts until mid-March. Latvia is characterized by cold, maritime climate (duration of the average heating period being 203 days, the average outdoor air temperature during the heating period being 0.0 °C, the coldest five-day average temperature being −20.7 °C, the average annual air temperature being +6.2 °C, the daily average relative humidity being 79 %). The first part of this research consists of operational air-to-water heat pump energy performance monitoring in different residential buildings during the winter season. The second part of the research takes place under natural conditions in an experimental construction stand which is located in an urban environment in Riga, Latvia. The inner area of this test stand, where air-to-water heat pump performance is analyzed, is 9 m2. The ceiling height is 3 m, all external wall constructions (U = 0.16 W/(m2K)) have ventilated facades. To calculate SPF, the experimental stand is equipped with sensors which provide measurements for electricity consumption and gained heat energy.