| 301 | Cornerways (Cheltenham and Gloucester College of Higher Education)GL50 2RF | Grade II |
| 302 | County Court with Attached Gate Pier Wall and RailingsGL50 1ND | Grade II |
| 303 | County HouseGL50 3BA | Grade II |
| 304 | Court House (28) and Attached RailingsGL52 6DJ | Grade II |
| 305 | Crescent Parade and Attached RailingsGL50 3PJ | Grade II |
| 306 | Crimean War Memorial Approximately 14 Metres North of the Queens HotelGL50 1NN | Grade II |
| 307 | Crofton Lodge and Attached Wall and PiersGL50 2ET | Grade II |
| 308 | Darley House and Attached Railings Number 25 and Attached RailingsGL52 6AQ | Grade II |
| 309 | Dawn Run InnGL52 2LP | Grade II |
| 310 | Dean Close HouseGL51 6QD | Grade II |
| 311 | Denham Lodge and Crenden with Attached RailingsGL51 6QB | Grade II |
| 312 | Devonshire House Lonsdale House and Attached Area RailingsGL53 7JX | Grade II |
| 313 | Dewerstone HouseGL53 7AD | Grade II |
| 314 | Dorset House (Shukutoku College)GL52 2BP | Grade II |
| 315 | Douglas House (Conservative Club)GL50 1UH | Grade II |
| 316 | Douro House and Attached Railings with Attached Wall and Gate Pier to RightGL50 2PQ | Grade II |
| 317 | Douro LodgeGL50 2PQ | Grade II |
| 318 | Dragon and Onion Lamp Post Approximately 14 Metres South West of Number 20GL50 1JU | Grade II |
| 319 | Dragon and Onion Lamp Post Behind Number 23 Imperial SquareGL50 1QZ | Grade II |
| 320 | Dragon and Onion Lamp Post Behind Number 33 Imperial SquareGL50 1UH | Grade II |
| 321 | Dragon and Onion Lamp Post Opposite Stamford HouseGL50 1HN | Grade II |
| 322 | Drake House with Attached Railings Piers and Garden WallGL50 2JH | Grade II |
| 323 | Drive Pier to South End of Carriage Sweep to Numbers 96 to 104GL53 7FE | Grade II |
| 324 | Dunalley HouseGL50 4ES | Grade II |
| 325 | Dunalley Street Primary School GL50 4AP | Grade II |
| 326 | Eagle LodgeGL50 1TY | Grade II |
| 327 | EastholmeGL52 2AJ | Grade II |
| 328 | Eaton Lodge (Cheltenham and Gloucester College of Higher Education)GL50 2SL | Grade II |
| 329 | Edenham and Westbury and Attached Area RailingsGL50 4JZ | Grade II |
| 330 | Edmonsone House (That Part to the Right)GL50 4EG | Grade II |
| 331 | Edward VII Drinking Fountain Approximately 20 Metres Sw of Montpellier RotundaGL50 1SJ | Grade II |
| 332 | Eglinton East and Eglinton WestGL52 2PT | Grade II |
| 333 | Electricity HouseGL50 3PW | Grade II |
| 334 | Ellenborough House and Attached Area RailingsGL52 2BB | Grade II |
| 335 | Ellingham House (Numbers 1 and 2) and Attached Area RailingsGL52 2BW | Grade II |
| 336 | Elmfield and Hazelwood (Number 1), Fernleigh and Oakfield (Number 3), Ashley and the Linden (Number 5)GL50 2EW | Grade II |
| 337 | Elm VillaGL52 6HE | Grade II |
| 338 | Entrance Gateway to Pittville ParkGL52 2BB | Grade II |
| 339 | Entrance to Fullwood (Cheltenham and Gloucester College of Higher Education)GL50 2RW | Grade II |
| 340 | Eslington House and Attached RailingsGL53 7AS | Grade II |
| 341 | Essex House (Number 18) and Attached Area RailingsGL50 1JS | Grade II |
| 342 | Eversleigh House (Cheltenhams Ladies College)GL50 3AF | Grade II |
| 343 | Everyman TheatreGL50 1HQ | Grade II |
| 344 | Evesham House Little Evesham HouseGL52 2AE | Grade II |
| 345 | Faithfull House (Central and Southern Parts) and Attached RailingsGL50 2AD | Grade II |
| 346 | Faithfull House (Northern Part) and Attached Area BalustradeGL50 2DT | Grade II |
| 347 | Farnley Lodge (Ymca)GL50 1TP | Grade II |
| 348 | Fauconberg House (Cheltenham Ladies College) with Attached RailingsGL50 3EB | Grade II |
| 349 | Fish and Fiddle Wine Bar and Attached RailingsGL50 1PT | Grade II |
| 350 | Five Gate Piers to Carriage Sweep with Railings to Numbers 107 and 109GL50 2RW | Grade II |