The properties of the novel compound cyclopropylmethylphosphine (C3H5CH2PH2) have been investigated by means of Stark-modulation microwave spectroscopy and high-level quantum chemical calculations. Spectra attributable to the three conformers of the molecule with a synclinal arrangement of the H-C-C-P atoms were recorded and assigned. The experimental rotational constants obtained for these conformers were found to be in good agreement with those generated by ab initio geometry optimizations at the MP2/aug-cc-pVTZ level of theory. An estimate of the relative energies of the three conformers with observable spectra, by means of relative intensity measurements, compared favorably with the results of G3 energy calculations performed for the molecule. In addition to the observation of ground-state rotational spectra for three conformers, spectra belonging to a number of vibrationally excited states were also assigned with the aid of radio frequency microwave double-resonance experiments. A tentative assignment of these excited-state spectra was proposed by appealing to the results of density functional theory vibrational frequency calculations performed at the B3LYP/6-311++(3df,2pd) level. The energetically preferred conformer of the molecule allowed a close approach between a hydrogen atom belonging to the phosphino group and the edge of the cyclopropyl ring. The possibility of the formation of an intramolecular hydrogen bond to electron density associated with so-called banana bonds is discussed.