| 34 S Main St | The U.S. Hotel |
| 36 S Main St | Rose Furniture Store: T.V. Howell Building |
| 44-46 S Main St | State of Ohio Liquor Control Store No. 56: F.P. Vorhis Home |
| 50-52 S Main St | Peck's Flower Shop: N.S. Selby, Shaffenberger Floral; Miami Valley Electric |
| 56 S Main St | Pickwick Building: Dr. David Bundy House |
| 65-67 S Main St | Commercial Building, Colonial Theater, Sorg Opera House |
| 68 S Main St | Brandenburg and Switzer, Architects: Old Barnitz Bank, Creo, Barnitz House |
| 71 S Main St | Sears Automobile Service Center |
| 100 S Main St | Kings Kitchen |
| 103 S Main St | 1002 E. First Ave.: 103 S Main St |
| 105 N Main St | Elks Temple |
| 107 S Main St | Sol Finkelman Real Estate and Insurance: Casper Fenzel house |
| 109 S Main St | 109 S Main St |
| 115 S Main St | Thompson House: Victor Hatfield House, Dr. John Corson House |
| 116 S Main St | American Legion, Middletown Post #218: Captain Robert Wilson House |
| 117 S Main St | Dr. John L. Bauer, Charles Denny House |
| 119 S Main St | Middletown Baptist Temple: First Baptist Church |
| 121 S Main St | Lindeman Home: Simon Goldman Residence |
| 124-126 S Main St | Chapple Leasing Company: Wilson House |
| 125 S Main St | American Red Cross, Middletown Chapter,: George Shafor House |
| 129 S Main St | 129 S Main St |
| 140 S Main St | Sohio Station |
| 201 S Main St | 201 S Main St |
| 206 S Main St | Sorg Mansion: Paul J. Sorg Home |
| 210 S Main St | Riggs Funeral Home Inc.: Alexander Hill House |
| 214-216 S Main St | 214-216 S Main St:Reiliartz home, Theodore Marston House |
| 218 S Main St | Calvin Verity Residence: F.P.Loeur House |
| 219 S Main St | 219 S Main St: Winchester House |
| 223-225 S Main St | 223-225 S Main St |
| 228 S Main St | 228 S Main St.: Daniel McCallay house |
| 229 S Main St | 229 S Main St: Judge Todhunter House |
| 231 S Main St | 231 S Main St: Wampler, Denny House |
| 300 S Main St | Tytus Mansion: John B. Tytus Mansion |
| 301 S Main St | 301 S Main St: Thomas Woodward House |
| 305 S Main St | 305 S Main St: Sabin Robbins Sr. House |
| 306 S Main St | 306 S Main St: Oglesby House |
| 308 S Main St | 308 S Main St: C.B. Johnson House |
| 309 S Main St | 309 S Main St: Sabin Robbins Jr. House |
| 313 S Main St | 313 S Main St |
| 314 S Main St | 314 S Main St: Jacoby house |
| 317 S Main St | 317 S Main St |
| 320 S Main St | 320 S Main St |
| 321 S Main St | 321 S Main St: Niederlander House |
| 400 S Main St | 400 S Main St: Iseminger House |
| 404 S Main St | Lefferson Home: Arthur Lefferson Home, Bates House |
| 501 S Main St | 501 S. Main : Sampson House, Breiel House |
| 502 S Main St | 502 S Main St: R. C. Phillips house |
| 503 S Main St | 503 S Main St |
| 507 S Main St | 507 S Main St: Stahl house |
| 508 S Main St | Colonial Manner Nursing Home:LeiBee house |
| 509 S Main St | 509 S Main St: Renick house |
| 510 S Main St | 510 S Main St: Carnahan House |
| 512 S Main St | 512 S Main St: John Boyd House |
| 514 S Main St | 514 S Main St: William Hanger Johnson house |
| 517 S Main St | 517 S Main St |
| 520 S Main St | 520 S Main St |
| 521 S Main St | 521 S Main St |
| 525 S Main St | 525 S Main St |
| 600 S Main St | 600 S Main St |
| 601 S Main St | 601 S Main St: Gabe Mayer |
| 603 S Main St | 603 S Main St |
| 604 S Main St | 604 S Main St.: D. E. Harlan House |
| 605 S Main St | 605 S Main St |
| 606 S Main St | 606 S Main St |
| 609 S Main St | 609 S Main St: W. T. Harrison |
| 610 S Main St | 610 S Main St: Anthony Walberg |
| 614 S Main St | 614 S Main St: Harding |
| 700 S Main St | 700 S Main St: James Lawrence House |
| 704 S Main St | 704 S Main St: E. Smith House |
| 715 S Main St | Dr. E. Norwood Clark house: Gibson house |
| 830 S Main St | George M. Verity Homesite |
| 915 S Main St | 915 S Main St |
| 2002 S Main St | ONG Armory Motor Vehicle Storage Building |
