Systemic osteoporosis is one of the most significant systemic factors capable of worsening bone tissue quality and affect osseointegration of dental implants. The increase in the number of patients of older age groups in need of implant treatment determines high clinical significance of preoperative assessment of the implant bed condition in this category of patients. The study aimed to assess clinical and morphological features of bone tissue in the dental implantation zone in patients with osteoporosis and determine the correlation of those with the primary stability of implants and early marginal bone remodeling. A total of 84 patients aged 55–75 were included in a prospective pilot study, who were planned for implantation in the areas of maxillar and mandibular premolars and molars: 42 with the confirmed systemic osteoporosis and 42 having no signs of osteoporosis. All the patients underwent CBCT with the bone quality and type determination in accordance with the Lekholm and Zarb classification; histological and histo-morphometric analysis of bone biopsy specimens was performed in a subgroup of 32 patients. Primary stability was assessed by the resonance frequency analysis; clinical monitoring was conducted after 2, 6, and 12 months. The D3–D4 type bones were more often found in patients with osteoporosis, along with lower bone density and implant stability quotient (ISQ) values, reduced bone volume fraction (BV/TV), trabecular thinning, and increased RANKL/OPG ratio. There was a positive correlation between the BV/TV, radiological bone density, and primary stability of implants. Systemic osteoporosis degrades the implant bed quality, therefore, the implantation protocol personalization and comprehensive preoperative assessment are required.