What about option #4 - Redirect your existing domain to the old domain? I bought an old domain that is 100% relevant to my current domain but currently has with very little content. It did have more content fours years ago. The old domain is 13 years old, pr=3, while my current is 7 months old pr=1 and a decent amount of content. The old domain I purchased was not expired though and I do not know if this makes a difference. What are the pros and cons of option #4? Am I correct to think that option #1 would result in no benefit from the old domain's age value and if so why is it not listed as a con, a MAJOR one. Its hard to believe that a 301 using option 1 would give my existing domain 13 years credit but I'll take it if it does.
Aside from places where you buy and sell domain names, there are some companies around that support the business of domain flipping. GoDaddy is one of the bigger names out there that does. There, you can not only trade domain names but also park those you’ve bought. The buying, parking and selling is relatively painless and all you must give up is a small percentage of your selling price.

Flipping domains are similar to flipping houses in real estate: You buy a property with potential, improve it, and then sell quickly for twice the profit (or more). Between 2005 and 2012, internet marketers had been obsessed with flipping domains… and for good reason. Many were successful at buying plain old domain names, spicing them up with keyword-stuffed content, giving them much-needed traffic, and then selling them off to the highest bidder. But in 2017, can this still be a viable online business?
As .COM is the natural domain extension for the United States based websites, it does get some priority in the Google.com’s search engine results (based on Google’s US datacenters) when competing against other countries’ domain extensions like .CO.UK, .CO.ZA, .COM.AU etc. However, .COMs don’t get automatic priority over other similar extensions like .ORG, .NET etc. that are also commonly used in the United States. All these domain extensions compete with .COMs on a level playing field.
If you are feeling ambitious, you can link each of your domain names to its matching “buy it now” purchase page at one of the marketplaces. Another more sophisticated option would be to “park” your domain with one of the leading domain parking companies, such as DomainSponsor or SmartName and enable their built-in “for sale” message and contact mechanisms.
The first thing you need to do is signup at Namejet in order to get your account (signup is free).  You can then use their search functionality to sort through all the upcoming domains for auction.  Place bids for $69 on the ones you want to go to auction for.  If you bid on 100 different domains for $69 each, and there is 50 bidders for each auction you need to understand you aren’t going to owe any money, you are not committing $6,900 to Namejet.  By entering that $69 you are getting an entry into the live bidding when the 30 days expire.  Only if you are the ONLY bidder on a domain would you automatically win the domain and owe $69 to Namejet.
So how do you develop that instinct? NameBio maintains a database of over 500,000 historical domain sales (as of writing this post). They have interesting filtering features by which you can narrow down domains by price range, date sold, keywords and more. Simply sifting through the listings on NameBio long enough will quickly develop your domain appraisal “instinct”.
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