| Time | Building |
| 19th century | Existing buildings: White Horses, former blacksmith's shop; Castell Deudraeth (the hospital in The Prisoner); main building; gardener's house, stables |
| 1925 | Conversion of the main building into a hotel, gardener's house becomes Mermaid; stables become Salutation |
| 1925/26 | Angel & Neptune |
| 1926 | Watch House, opening of the hotel |
| 1927/28 | Campanile; Prior's Lodging |
| 1928/29 | Government House |
| 1929 | Toll House |
| 1930 | Amis Réunis |
| 1930s | Town Hall (Hercules Hall); Pilot House; Battery Cottage, Dolphin; Fountain; Anchor, Trinity |
| 1933/34 | Chantry |
| 1937/38 | Camera Obscura |
| 1954 | Lighthouse (after the end of building restrictions during the Second World War) |
| 1954/55 | Gate House |
| 1956/57 | Telford's Tower |
| 1958 | Bristol Colonnade; High Cloister (porch of the dome) |
| 1958/59 | Round House (residence of number 6 in The Prisoner), Bridge House |
| 1959 | Pantheon – dome (the green roofing had to be removed after renovations in the 1990s due to fire protection requirements) |
| 1960 | Belvedere |
| 1961/62 | Chantry Row |
| 1962 | Playhouse |
| 1963 | Triumphal Arch; Gothic Pavilion |
| 1963/64 | Arches |
| 1964 | Gloriette Balkon |
| 1964/65 | Unicorn |
| 1966 | Villa Winch; Central Piazza (replacing a tennis court) |
| 1968/70 | Cliff House |
| 1977 | New Toll Booth |
| 1978 | Terrace, self-service restaurant |
| 1981 | The hotel was destroyed by fire |
| 1983 | Centenary Gazebo; Prisoner information centre opened in the Round House |
| 1988 | Reopening of the hotel after reconstruction |
| 1998 | Tudor Room, annex to the Hercules Hall |
| 1999 | Prisoner Information Centre closed; second pay kiosk opposite Toll Booth; Castell Deudraeth reopened as hotel after renovations. |
| 2001 | New Prisoner shop in the Round House |
| 2007 | Caffi Glas (The Blue Café), Italian restaurant (built 1950 as garages for guests) |
| 2016 | Permanent chess set, built in remembrance of The Prisoner next to the central piazza |
