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So, I am working on a site which has property listings, after some of the properties are expired its giving 404 errors. From what I understand, good way to handle these expired pages is to 301 redirect them to their nearest region pages.

Now the main confusion is, what if a property comes up again for any reason its not sold or rented out, but that property url is already 301 redirected to other page. What would be the best way here? Because removing 301 on this page will take manual effort as well it might take some time for google to re-index that page again.

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Neither 404 errors or 301 redirects seem preferable in this situation. The page should still return a 200 status code, but inform the user that the property listing has expired. Then provide a manual link for finding properties nearby. You should also change the meta information to noindex so the search engine knows the page is finished. If the property goes back up as a listing remove the noindex so the search engine knows to re-index the page.

Why is 404 bad?

The 404 error is bad because you are providing the end-user with a negative experience making your site appear broken.

Why is 301 bad?

In this case it seems that you're forcing the user into an area that they didn't anticipate. It's also not the same listing, so you're telling the search engine that your content moved, but in reality it didn't. It just went away. Also it creates the negative effect you stated that occurs when a property goes back up for listing.

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    Why does 404 mean negative user experience? The user doesn't care what the status code is, they care about the content. Your suggestions as to what should appear on the page don't prevent that page sending a 404 status code, which avoids the need to jump through hoops to prevent robots indexing it. Aug 24, 2016 at 23:15
  • Thanks JMC for the explanation, I really like the 200 status code thing wherein you can simple say this property is not on sale with XYZ company name. I am not sure about the no-index part, is this something which can be automated, I mean there are like hundreds of listing going down everyday and it would be quite a task to go through them and no-index them manually. Also @tim I am not sure what exactly you mean here, are you saying that no-index is not a good option?
    – NRose
    Aug 25, 2016 at 13:46
  • @TimFountain: A 404 can be made into a normal user experience of course, but it comes down to the use case and if you're okay with telling search engines that you don't really know whats going on with hundreds or thousands of pages that were once indexed. Webmaster Tools calls 404 "crawl errors". Seems preferable to keep those to a minimum. Maybe it doesn't matter in the grand scheme.
    – JMC
    Aug 25, 2016 at 19:09
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The best way is to create a custom 404 page where you can display: "Unfortunately, there are no ads for this property right now, below is a listing of other properties in your area that you can visit."

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You should not use 301 redirect in your situation. 301 Redirect helpful when you moved same content to other permalink. I never recommend to use 301 to display relative product or property, instead you can write that, this property is sold out or something else, which gives better experience in my eyes. Checkout amazon website, they use same content, they just change option from available to sold out when they have no product, so you don't need use noindex tag either.

301 redirect is equal to 1 webpage with 1 link, both pass same pagerank, as far I understand. So better to provide useful information to user. Just think yourself, if someone redirect you to some other webpage which you have not requested, do you like that experience? No, but what if you see the page that says product is not available at this time, so you can checkout some alternative here or something like that, so that is good user experience.

If the product/property is expired, then matt cutts recommended to use unavailable_after tag. .

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