Let me add one other twist to slaudenslag's excellent answer. Keep in mind that because you owned these properties with a co-owner who is now deceased, your basis may be higher than your original purchase price. That's because when you inherit property, you receive a step-up in basis to the value at the date of death. In other words, your capital gains exposure could be lower than it appears.
I will give an example to help illustrate this.
You and your late husband bought your house in 1989 for $135,000. Since you owned it jointly, think of this as you owning half of the house with a basis of $67,500 in your half, and him owning half of the house with a basis of $67,500 in his half. Now let's say that when he passed away, your house was worth $300,000 (I don't know when he passed, or anything about real estate prices in your area, so this is just for illustration). At that time, the value of his half of the house would have been $150,000 - half of $300,000. So, you inherited his half, and your basis in that half is $150,000. While you might think your total basis in the house is $135,000...it's not. In this example it would now be $217,500 ($67,500 basis in your half plus $150,000 stepped-up basis in his half) meaning you could apply the $250,000 exclusion up to a $467,500 sales price...in actuality higher because you may have made improvements to the house over the years and you will surely have some costs related to the sale.
Also, I don't know what state you live in, but there are special considerations in certain community property states (such as California). For example, in California, the entire property is stepped up upon the death of one co-owner. So in the example I just provided, your basis would be $300,000, not $217,500.
The same principle applies to your fiancee's house. Depending on when his late spouse passed away, his basis may be much greater than he thinks.
I hope this information is helpful in your planning process.
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