The first glimpse of the Monastery which the pilgrim gets as he descends the agricultural road approaching from Karyes is the impression of a well-fortified castle, ruled over by the iconic tower of its defenders, while the exterior structures seem to be trying to protectively hide the cathedral and the other interior buildings. This obviously defensive arrangement reminds one of the historic 'adventures' of the Monastery which, mainly during the critical period of its founding, but also for all the years of the Ottoman period, had to face a variety of enemies and raiders.
Everyone who has been involved with the architecture of the Monastery defines its shape as being irregular or polygonal. This most likely results from the construction interventions and extensions which were done over the course of the centuries to such a degree, in fact, that it is hard to believe that “The buildings within the compound which we see today date basically to the 17th and 18th century.” Thus, it is theorized that the original building construction must be confined to the northwestern section of today's building complex and to the cathedral, surrounded by the rooms of the monks. According to more recent evidence, the extension of the buildings toward the southeast probably dates from between 1483 to1535, a view which has been confirmed by the relevant references of Barsky and Komnino that the “new courtyard” of the Monastery is the work of Barboulou.
The buildings are not higher than three floors, and are characterized on the interior by well-built roofed arcades and rich ceramic decoration, while on the exterior, wooden balconies and sachnisia (i.e., enclosed balconies with windows) offer an exceptional view of the sea or the sheer peak of Mt Athos.
The main entrance to the Monastery is found on the southwestern corner, where a small, low, square tower stands. The Chapel of St Panteleimonos is located on the top floor of this tower, and this tower also had cannons and other means of defense, which are shown in engravings depicting the Monastery. Directly aligned with this and in front of the entrance to the Monastery is a gate, supported on two pillars and two columns. To the right of the gates, there is a marble fountain filled by a natural spring of fresh water. The fountain was built as part of the renovation work done at the end of the 18th century. That work was financed by grants from Cyrillos and Georgios, as can be seen in an engraved inscription. (According to the inscription, Cyrillos was the Sacristan of the Monastery.)
At the edge of the sheer cliff a few metres north of the gates, there is a square pavilion, which is depicted in the plans of the Monastery made by Barsky in 1744. From there, visitors can enjoy a singular view towards the sea, the neighboring Stavronikita Monastery, and in the distant horizon, the rocky peak of Mt. Athos.
The north side of the cathedral is visible to a visitor entering the courtyard area of the Monastery, which slopes upward at this point. However, this area did not always have the shape that it has today: According to Barsky, there were two small courtyards, separated with a wall. The purpose of the wall was to separate the Brothers of the Monastery from the craftsmen and workers who lived in the area of the first small yard. The two yards were merged into one after the middle of the 18th century.
At the left, at about the centre of the west wing, there is a second marble fountain, which also was built with a grant from the Cyrillo mentioned above, and the well-known palindrome ΝΙΨΟΝ ΑNOMHMΑTΑ ΜΗ ΜΟΝΑΝ ΟΨΙΝ (“Wash [away] your sins, not only your face”) is inscribed on it.
Today, all of the wings which surround the cathedral of the Monastery have been completely renovated by the new Brotherhood of the Monastery. The north wing houses the rooms of the monks, the offices, the Prior's office, as well as the chapels of St Andrew and Ioanniko, the Archangels, and St Georgios. This area is part of the original building complex and had suffered damage in the fire of 1392. It has undergone repeated renovations, first by the autocrat Manuel II Palaiologo and the Patriarch Antonio IV, and later, in 1781, by the above-mentioned Cyrillos and Georgios, as evidenced by the extant inscriptions from that year.
It is worth noting that on the ground floor of this wing, the storage jar which is associated with the miracle of the olive oil performed by the icon of Panagia Gerontissa ('The Virgin Mary, the Wise and Venerable' or 'The Abbess'). The west wing houses the kitchen (a building of the 16th century), the dining hall, the storage room, the chapel of St John the Baptist (Timio Prodromou), and the rooms of the monks. Earlier renovations to sections of the west wing around 1637 and 1776 are evidenced by the surviving inscriptions on the outer walls.
Visitors to the monastery are accommodated in the south wing, which also houses the conference room and the chapel of St Nikolaos. According to tradition, this wing was formerly the location of the Prior's office, the dining hall (or refectory), a room for dignatires and guests, and the rooms of the monks.
The garden is located a short distance to the west of the Monastery, which is also the site of the Seat of St Trifonas, surrounded by olive trees, as well as the cemetery and the Seat of the Sts Anargyrioi (i.e. 'Those who work without being paid in silver').
At a short distance north of the small harbour of the Monastery is the well where the miraculous icon of Panagia Gerontissa has continued to stand for almost 80 years.