Kentucky - Criteria: C (architecture/engineering)
| Old Statehouse Historic District |
| Old Stone Tavern |
| Old Talbott Tavern |
| Old Taylor Distillery |
| Oldtown Covered Bridge |
| Old Town Historic District |
| Old U.S. Courthouse and Post Office |
| Old U.S. Customshouse and Post Office |
| Old Wash Place |
| Old Zion Methodist Church |
| Olive Branch Methodist Episcopal Church |
| Olive Hill C & O Depot |
| Olmsted Park System |
| Olympic, The |
| O'Neal, James, House |
| Opera House and Yates Bookshop Building |
| Overby, L. B., House |
| Owen County Courthouse and Jail |
| Owings, Col. Thomas Deye, House |
| Owingsville Commercial District and Courthouse Square |
| Oxford Historic District |
| Oxmoor |
| Paducah City Hall |
| Paducah Coca-Cola Bottling Plant |
| Page, William House |
| Paint Lick Presbyterian Church |
| Paintsville City Hall |
| Paintsville Country Club |
| Paintsville High School |
| Paintsville Public Library |
| Paramount Theatre |
| Paris Courthouse Square Historic District |
| Parke-Moore House |
| Parker House |
| Parkland Evangelical Church |
| Passmore, Benjamin, House |
| Passmore, George, House |
| Patterson, Horace, House |
| Patterson House |
| Patterson, Thomas, House |
| Patton, Robert, House |
| Pauley Bridge |
| Payne House |
| Payne House |
| Payne, Lewis, House |
| Peacock House |
| Peacock-Miller House |
| Peak, Henry C., House |
| Peak House |
| Peaslee-Gaulbert Warehouse |
| Peebles, Dr. Thomas C., House |
| Pell, Joe, Building |
| Pendennis Club |
| Pendleton House |
| Pendleton House |
| Pennsylvania Run Presbyterian Church |
| People's First National Bank and Trust Company Building |
| Perryville Historic District |
| Peters House |
| Peterson-Dumesnil House |
| Pettit's, James, Mill |
| Phillips' Folly |
| Piatt's Landing |
| Pikeville College Academy Building |
| Pile, Benjamin, House |
| Pineville Courthouse Square Historic District |
| Pinkerton Hall |
| Pioneer Log Cabin |
| Pirtle House |
| Pisgah Presbyterian Church |
| Pisgah Rural Historic District |
| Pleasant Run Methodist Church |
| Pleasant Run Stone House I |
| Pleasant Run Stone House II |
| Poague House |
| Poindexter, William, House |
| Point Au View |
| Pope, John, House |
| Pope Villa |
| Poplar Hill |
| Porter, Bradford, House |
| Porter-Todd House |
| Portsmouth Earthworks, Group A |
| Powell, William S., House |
| Poynter Building |
| Presbyterian Manse |
| Presentation Academy |
| President's Home |
| Preston House |
| Prewitt, Levi, House |
| Price, Dr. A. D., House |
| Prichett House |
| Princeton Downtown Commercial District |
| Proctor, George N., House |
| Proffitt, George W., Jr., House |
| Prospect Farm |
| Providence Baptist Church |
| Providence Church |
| Purdom, Clel, House |
| Pusey, Dr. Robert B., House |
Data from United States Park Service and Wikidata
