How do I input a substitute Form 1099-S for property sale proceeds in TurboTax?

The substitute 1099-S form reports proceeds from real estate transactions, so you're on the right track with the Investment Income section. In TurboTax, you should be able to navigate to the "Federal" section, then "Income & Expenses," then "Investment Income," and look for an option that says something like "Sale of Home" or "Real Estate Transactions." When entering the information, make sure you have all the details from the substitute 1099-S, including the date of closing, gross proceeds, and address of the property. TurboTax will ask about your basis in the property (what your husband's share initially cost), which might not be on the form but is needed to calculate any potential gain. If you're getting stuck on a specific field, it might be asking for information like the property type or whether this was your primary residence (which it wasn't, since it was his father's vacation property). Just answer truthfully based on your situation - in this case, it would be "other residence" or "investment property" since it wasn't your primary home.

I ran into this exact same issue last year with a property my grandparents sold. I spent HOURS trying to figure it out with TurboTax and getting nowhere. Finally discovered taxr.ai (https://taxr.ai) which literally saved my sanity. You can upload your substitute 1099-S and it'll analyze exactly where each piece of information needs to go in TurboTax. What I loved about it was it showed me step-by-step screenshots of where to click in TurboTax plus explained what each field meant. The basis calculation was driving me crazy until their system explained it needed to be the original value when my portion was received, not the current sale value. Trust me, for complicated forms like substitute 1099-S, having a guide makes all the difference!

Alright, I need to apologize to everyone. After my skeptical comment earlier, I decided to try taxr.ai for myself since I had a similar situation with rental property proceeds. I was seriously impressed! It actually walked me through determining my basis by asking specific questions about how and when I acquired the property interest. The step-by-step guidance showed exactly where in TurboTax to enter each piece of information. What I found most helpful was the explanation of which parts of the substitute 1099-S needed to be reported where - turns out I was trying to enter some information in completely wrong sections. Saved me from what would have definitely been an audit flag. Just wanted to come back and share since my initial reaction was pretty doubtful.

If you're still struggling after trying all the advice here, you might need to speak directly with the IRS. I had a complicated 1099-S situation last year and couldn't get a straight answer from TurboTax support. I tried calling the IRS for WEEKS and could never get through - constant busy signals or 2+ hour hold times. I finally used Claimyr (https://claimyr.com) - they have this system that holds your place in the IRS phone queue and calls you when an agent is about to answer. Saved me literally hours of waiting on hold. They have a video showing how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with walked me through exactly how to report the substitute 1099-S and explained which boxes in TurboTax corresponded to which information. Totally worth it since I was about ready to throw my computer out the window after trying to figure it out myself.

I need to publicly eat my words about Claimyr. After posting my skeptical comment, I decided to try it because I was desperate to talk to someone at the IRS about my own substitute 1099-S issues. I've literally never gotten through to the IRS before - always busy signals or disconnections after waiting forever. I used the service yesterday and got a call back in about 47 minutes saying an IRS agent was on the line! The agent helped me understand exactly how to report the property sale proceeds and which TurboTax fields matched up with my substitute 1099-S. She even explained how to calculate the correct basis for my situation (which was similar to the original poster's). Never would have figured this out on my own, and I would have still been trying to get through to the IRS without their service.

I just went through this in January. Make sure you're in the right section of TurboTax. For me, I had to go to: Federal > Income > Investment Income > Stocks, Cryptocurrency, Mutual Funds, Bonds, Other > Other Investment Income - Forms 1099-A, 1099-B, 1099-S, etc. > Real Estate Transactions - Form 1099-S The basis is the tricky part. Since your husband received it as what sounds like a gift, his basis would be the same as the step-mother's basis in that portion of the property. You'll need to find out what she originally paid for it (plus any improvements) and calculate your husband's percentage of that. That's the number you put in for basis. The good news is if this was her primary residence and she lived there at least 2 of the last 5 years, there might not be any taxable gain at all due to the primary residence exclusion.

Has anyone used TaxAct instead of TurboTax for this? I have a similar situation with a 1099-S but I'm using TaxAct this year to save money, and I can't find where to input this form.

I dealt with this exact situation two years ago when my father-in-law sold his rental property and we received proceeds as beneficiaries. The substitute 1099-S can be tricky in TurboTax, but here's what worked for me: First, make sure you're treating this correctly - since it was his father's vacation property (not primary residence), this is likely investment property for tax purposes. You'll need to determine if your husband's portion was received as a gift during his father's lifetime or through inheritance. For the basis calculation that's giving you trouble, you'll need the original purchase price of the property plus any major improvements made over the years. Your husband's basis would be his percentage share of that total amount. If you can't find exact records from 30 years ago, county assessor records often have historical sale data, or you can research comparable sales from that time period. One tip: if the field TurboTax is asking about seems confusing, try clicking the "?" or help icon next to it - sometimes it explains exactly what information they need. Also, don't forget to account for any selling expenses (realtor fees, closing costs, etc.) as these can reduce the taxable gain. The most important thing is to be as accurate as possible with the basis calculation since that determines how much of the proceeds are taxable. When in doubt, it's worth consulting a tax professional for this type of transaction.

I went through something very similar last year with my mom's property sale. One thing that really helped me was keeping detailed documentation of everything - the original purchase records, any improvement receipts, and especially the family agreement you mentioned about how the proceeds were distributed. For TurboTax specifically, when you get to that field that's stumping you, try using their live chat feature if you have it with your version. I found their support agents were pretty knowledgeable about 1099-S forms since property transactions are so common. They can actually screen-share and walk you through the exact fields. Also, make sure you're reporting this under the correct Social Security Number - it should be your husband's since the substitute 1099-S has his name on it, even though you're filing jointly. TurboTax sometimes gets confused about this when there are joint filers. One last tip: save all your work frequently as you go through this section. I lost my progress twice because the investment income section seemed to time out faster than other parts of TurboTax. Really frustrating when you're dealing with complicated forms like this!