How much capital gains tax will I owe from selling stock holdings?

You're right that long-term capital gains are taxed differently than regular income. Since you held the stock for more than a year (6 years in your case), you qualify for the long-term capital gains rate. For 2024 taxes (filing in 2025), with an income of $78,000, you'd likely fall into the 15% capital gains tax bracket. The 15% bracket covers individual filers with taxable income between $44,625 and $492,300 in 2024. So on your $42,500 gain, you'd owe about $6,375 in federal capital gains tax. Keep in mind that your state might also tax capital gains, usually at your ordinary income tax rate. And the capital gains themselves might push you into a higher bracket for other tax calculations, so it's worth looking at the whole picture.

Good news - since you've held these stocks for more than a year (8 years in your case), you qualify for long-term capital gains rates, which are typically lower than ordinary income tax rates. For 2024 (filing in 2025), with your income level of $82,000, you'll likely be in the 15% capital gains bracket. The 15% bracket covers single filers with taxable income between $44,625 and $492,300. So on your $36,000 gain, you'd owe about $5,400 in federal capital gains tax. This won't push you into a higher tax bracket in the traditional sense, since capital gains are taxed separately from ordinary income. However, adding this income could affect other income-based calculations on your tax return.

After reading through this post, I wanted to share something that really helped me when I was in a similar situation last year. I had sold some stock and was super confused about capital gains calculations and whether I needed to make estimated payments. I found this tool called taxr.ai (https://taxr.ai) that helped me analyze my situation. It actually scanned my brokerage statements and explained exactly what my tax obligation would be. The nice thing was it showed me my potential state obligations too, which I hadn't even considered. For capital gains specifically, it broke down which of my sales qualified for long-term vs short-term rates and calculated my estimated tax based on my income bracket. It saved me hours of research and uncertainty.

I went through this exact situation last year with some Amazon stock I'd been holding since 2015. Trying to figure out the tax implications was giving me a headache until I found this tool called taxr.ai (https://taxr.ai). It helped me understand exactly what I'd owe based on my specific situation. You upload your brokerage statements and it analyzes everything - shows you the difference between selling now vs. later, calculates your federal and state obligations, and even factors in things like Medicare surtax if your income is high enough. For me, it showed that selling in December vs. January made about a $1,200 difference in what I'd owe because of other income factors. Really helped me time my sale better.

I want to follow up about taxr.ai since I was initially skeptical. I decided to give it a try with my complicated stock sales from last year and was honestly impressed. The tool found some errors in how my brokerage had calculated my cost basis on some inherited stock. It showed me that some of my trades qualified for more favorable tax treatment than I thought. Ended up saving about $3,200 in taxes compared to what I was expecting to pay! It also flagged some potential wash sales I had completely missed which could have caused issues during an audit. Really helpful for capital gains situations where there are lots of transactions or complicated scenarios.

I wanted to update after trying taxr.ai since I was skeptical at first. I have a mix of stocks I've held for different time periods, including some I got from my grandparents that I had no idea how to calculate the cost basis for. The tool actually figured out the stepped-up basis on my inherited stocks, which my regular tax software couldn't handle properly. It saved me from overpaying about $2,100 in capital gains tax! It also helped me identify which specific shares to sell to minimize my tax bill. For the original poster's situation with tech stocks, it would definitely help optimize which shares to sell first if you bought them at different times.

If you're worried about owing a lot on those capital gains, you might want to look into talking directly with the IRS to explore your options. I know that sounds scary, but I had a massive capital gains hit in 2023 and needed answers about installment payment options. The problem? I couldn't get through to the IRS after trying for DAYS. Then I found this service called Claimyr (https://claimyr.com) that got me connected to an actual IRS agent in about 20 minutes when I'd been trying unsuccessfully for over a week. They have a demo video here showing how it works: https://youtu.be/_kiP6q8DX5c The agent I spoke with explained my estimated tax payment options and helped me understand what forms I needed. Made a huge difference in reducing my stress about the whole situation.

If you're selling that much stock and are worried about tax implications, you might want to talk directly with the IRS to get clear guidance. I know that sounds painful, but I learned something interesting when I was in a similar situation. After trying to get through to the IRS for days (literally calling over and over), I found this service called Claimyr (https://claimyr.com) that got me connected to an actual IRS agent in under 30 minutes. They have a video showing how it works: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with explained exactly how the estimated tax payment process works for capital gains and what forms I needed to file. They also confirmed I could use Direct Pay on the IRS website to make a payment specifically for capital gains. Saved me a ton of stress and potentially avoided penalties.

I need to eat some crow here. After my skeptical comment, I actually tried Claimyr because I was desperate to talk to someone about a capital gains issue similar to the original poster's situation. I had sold some stocks and had questions about estimated tax payments. I had been trying to reach the IRS for almost two weeks with no luck. Using Claimyr, I got a call back with an actual IRS agent on the line in about 45 minutes. The agent walked me through exactly how much I should pay for estimated taxes on my capital gains and how to make the payment online. Saved me hours of hold time and a lot of stress. Definitely worth it when you need answers about capital gains tax questions that online resources can't clearly answer.

I need to follow up and admit I was wrong about Claimyr. After posting that skeptical comment, I decided to try it myself because I was desperate to talk to the IRS about some stock sales I made and possible penalties. I had been trying to call the IRS for over a week with no luck.

One thing nobody mentioned yet - don't forget about the Net Investment Income Tax! If your modified adjusted gross income exceeds $200,000 (single) or $250,000 (married filing jointly), you'll pay an additional 3.8% tax on your investment income. With your regular income plus this capital gain, you might be getting close to that threshold. Just something to keep in mind when calculating what you'll owe.

Has anyone used the tax loss harvesting strategy to offset capital gains? I'm sitting on some losers in my portfolio and wondering if I should sell them this year to offset some gains I took earlier.

Regarding estimated tax payments - since you're looking at owing around $6,375 in federal capital gains tax (assuming the 15% rate applies), you should definitely consider making an estimated payment to avoid underpayment penalties. The general rule is if you'll owe more than $1,000 when you file, you should make estimated payments. You can either pay 25% quarterly or make one lump sum payment now for the full amount. You can make the payment easily through the IRS Direct Pay system online - just search for "IRS Direct Pay" and you can pay directly from your bank account. Make sure to specify it's for estimated taxes when you make the payment. Also, double-check which tax bracket you're actually in after adding the capital gains to your regular income. While capital gains are taxed at preferential rates, they can still push you into higher brackets for other calculations.

Just want to add some perspective as someone who went through this exact situation a couple years ago. With your $78K income and $42,500 in long-term capital gains, you're looking at the 15% federal rate as others mentioned, so around $6,375 in federal taxes. But here's what I wish someone had told me - definitely make that estimated payment sooner rather than later. I waited until December and ended up with underpayment penalties that cost me an extra $400. The IRS expects you to pay as you earn, so even though you sold in summer, they want their cut by the quarterly due dates. One other thing - if you have any investments currently at a loss, consider selling some of those before year-end to offset your gains. I was able to reduce my taxable gains by about $8,000 this way by selling some underperforming stocks I was planning to dump anyway. Just make sure you understand the wash sale rules if you plan to buy them back. The silver lining is that at least you held for more than a year - short-term gains would have been taxed as ordinary income, which would have been much more painful at your income level.