Several biomedical applications, such as detection of dysplasia, require selective interrogation of superficial tissue structures less than a few hundred micrometers thick. Techniques and methods have been developed to limit the penetration depth of light in tissue, including the design of systems such as fiber-optic probes that have overlapping illumination and collection areas on the tissue surface. For such geometries, the diffusion approximation to the light-transport equation typically does not apply, and as a result there is no general model to extract tissue optical properties from reflectance measurements. In the current study, we employ Monte Carlo (MC) simulations to develop simple and compact analytical models for the light reflectance from these overlapping geometries. These models incorporate the size of the illumination and collection areas, the collection angle, the polarization of the incident light, and the optical properties of the sample. Moreover, these MC simulations use the Whittle–Matérn model to describe scattering from spatially continuous refractive index media such as tissue, which is more general than models based on the conventionally used Henyey–Greenstein model. We validated these models on tissue-simulating phantoms. The models developed herein will facilitate the extraction of optical properties and aid in the design of optical systems employing overlapping illumination and collection areas, including fiber-optic probes for in vivo tissue diagnosis.