Massachusetts - Significance region: Local
| Prospect Park |
| Providence Court |
| Providence Street Historic District |
| Provincetown Public Library |
| Provost, Arthur, Three-Decker |
| Publicity Building |
| Purchase-Ferre House |
| Puritan House |
| Quaker Meetinghouse |
| Quincy Electric Light and Power Company Station |
| Quincy Grammar School |
| Quincy, Josiah, House |
| Quincy Point Fire Station |
| Quincy Police Station |
| Quincy Savings Bank |
| Quincy School |
| Quincy Water Company Pumping Station |
| Rabbit Hill Historic District |
| Radding Building |
| Railway Village Historic District |
| Ramsdell Public Library |
| Randall-Hale Homestead |
| Rawson, Warren, Building |
| Rawson, Warren, House |
| Reading Municipal Building |
| Reading Municipal Light and Power Station |
| Reading Standpipe |
| Record, Jonathan Dexter, House |
| Red Brick School |
| Reed and Barton Complex |
| Reed, Frank, Three-Decker |
| Reed, H.R., House |
| Reed, Timothy, House |
| Reed-Wood Place |
| Reeves Tavern |
| Rehoboth Village Historic District |
| Remick, Joseph, House |
| Renfrew Mill No. 2 |
| Repertory Theatre of Boston |
| Revere City Hall and Police Station |
| R. H. Long Company Factory |
| Rhodes, M.M. and Sons Co. |
| Rice, A.H., Silk Mill |
| Rice, Capt. Peter, House |
| Richards, Alfred H., House |
| Richardson Block |
| Richardson, Dr. S. O., House |
| Richardson, John, House |
| Richardson, Zachariah, House |
| Richard, Stephen, House |
| Richmond Court |
| Rider Tavern |
| Ridgewood Cemetery |
| Ridyard, Albert, Three-Decker |
| Ridyard, B. E., Three-Decker |
| Ringville Cemetery |
| Riordan, John, Three-Decker |
| Ritter House |
| River Road-Cross Street Historic District |
| Riverside Concrete Company-Lamont's Market |
| Riverside Village Historic District |
| Riviera, The |
| Robbins, John, House |
| Robbins, Joseph, House |
| Robbins, Royal E., School |
| Robert, Clovis, Block |
| Roberts House |
| Roberts School |
| Robindreau, Alfred E., House |
| Robin Hill Cemetery |
| Robinson Building |
| Robinson, Capt. Joel, House |
| Robinson House |
| Robinson-Lewis-G. F. Fessenden House |
| Rock Castle School |
| Rockdale Common Housing District |
| Rockland High School |
| Rockland Memorial Library |
| Rockland Trust Company |
| Rocklawn Cemetery |
| Rockport Downtown Main Street Historic District |
| Rockport High School |
| Rockport High School, Old |
| Rock Ridge |
| Rocks Village Historic District |
| Rockwood Road Historic District |
| Rocky Neck Historic District |
| Roebuck Tavern |
| Rogers Fort Hill Park Historic District |
| Rogers House |
| Rollins, John R., School |
| Ronan, Mary, T., School |
| Rose, John and Ruth, House |
| Roslindale Baptist Church |
| Roslindale Congregational Church |
| Roslindale Substation |
| Roughan Hall |
| Round House |
| Rowell House |
| Rowhouses at 256-274 Haven Street |
Data from United States Park Service and Wikidata
