(1) Background: Frailty in older adults is a condition that involves an interaction of psychological, biological, and social factors. This study aimed to assess the frailty status of older adults (65 years old and above) who receive home care services. Additionally, this work aimed to explore the key factors that have a statistically significant impact on the frailty of this vulnerable population. (2) Methods: This study represents the first phase of an intervention trial involving individuals aged 65 and over who received primary healthcare services and resided in the municipality of Archanes-Asterousia in Crete, Greece. Frailty was assessed using the SHARE-Frailty Instrument, while nutritional status was evaluated with the Mini Nutritional Assessment. Diet-related factors were analyzed, including health factors (oral hygiene, depression, cognitive decline, impaired functioning, quality of life), social factors (educational attainment, marital status, type of work before the age of 60), and lifestyle factors (smoking, alcohol consumption, diet). (3) Results: A total of 730 older adults were evaluated (31.5% male), with an average age (±SD) of 76.83 (±6.68) years. The frailty status analysis revealed 108 (14.8%) to be frail, 249 (34.1%) to be pre-frail, and 373 (51.1%) to be non-frail. Statistically significant associations were found between the MNA and Barthel scores (rs = 0.822, p < 0.001). Higher nutritional evaluations (MNA) were revealed in non-frail adults (mean (±SD); 26.97 ± 1.96) compared to pre-fail (mean (±SD); 19.37 ± 3.36) and frail adults (mean (±SD); 13.08 ± 3.16), as well as in pre-fail compared to frail adults (F = 1338.08, p < 0.001). Functional independence (Barthel) significantly differed with the frailty status of older adults (H = 521.98, p < 0.001; median for non-frail: 20.00, pre-fail: 19.00, frail adults: 15.00). (4) Conclusions: This study demonstrated that good nutritional status, good oral health, functional independence, and good quality of life are strongly correlated with lower frailty. Additionally, having chronic conditions is positively associated with one’s frailty status. Educational programs for both healthcare personnel and older adults are recommended.