Wall Street RegretsThe regret calculator.

What if you'd held Z?

A $1,000 investment in Zillow Group, Inc. (Z) at the month-end close of 2015-08 would be worth $1,483 at the close of 2026-08 — +48.3% total return, dividends reinvested. The same $1,000 in the S&P 500 would be worth $3,908.

$1,000 since 2015$1,483Total return+48.3%Multiple1.5×CAGR+3.6%

Your scenario

Dates resolve to the nearest month-end close.
Leave empty for "held until today".
Invested at each month-end. Starts on the buy date.

Result

Worth$1,483Gain+$483 (+48.3%)Multiple1.5×CAGR+3.6%

    If you'd bought $1,000 at the start of each year

    Value of $1,000 invested on January 1 of each year, held to 2026-08, dividends included.

    2015$1,4832016$1,5582017$1,0032018$8942019$1,1582020$7962021$2822022$5732023$1,1362024$6322025$4942026$536

    Every year, $1,000 from 2015

    YearValue of $1,000Year return
    2015$1,000
    2016$1,553+55.3%
    2017$1,743+12.2%
    2018$1,345-22.8%
    2019$1,957+45.5%
    2020$5,528+182.5%
    2021$2,719-50.8%
    2022$1,372-49.6%
    2023$2,464+79.6%
    2024$3,154+28.0%
    2025$2,905-7.9%
    2026$1,558-46.4%

    Best and worst month-end to buy

    The best single month-end close to have bought Z was 2016-01 ($20.50): $1,000 then is $1,784 today. The worst was 2021-02 ($161): $1,000 then is $227.

    FAQ

    What would $1,000 in Z be worth today?

    A $1,000 investment in Zillow Group, Inc. (Z) at the start of 2015 would be worth about $1,483 today, a total return of +48.3%. Dividends are reinvested in these figures.

    What were the best and worst years for Z?

    Zillow Group, Inc. (Z)'s strongest calendar year since 2015 was 2020, a +182.5% return — $1,000 held through that year became about $2,825 by year-end. Its weakest year was 2021, at -50.8%.

    Does the calculator include dividends and splits?

    Yes where available. Prices are adjusted for both stock splits and reinvested dividends (total return), the same measure brokerages use.

    How much would $100 per month in Z have grown?

    Investing $100 at the end of every month since 2015-08 would have grown to about $10,859 on $13,300 invested.

    Did Z beat the S&P 500?

    Over the same period, $1,000 in the S&P 500 index would be worth $3,908. Z trailed the S&P 500 by +62.0% in total return.

    Is this investment advice?

    No. Wall Street Regrets is an entertainment and education tool. Every number is a historical calculation, not a prediction, and past performance never guarantees future results.

    Methodology

    Zillow Group, Inc. (Z) historical total-return data from 2015-08 to 2026-08, reduced to month-end closes for the tables above.

    Returns use adjusted close prices from Yahoo Finance historical data — adjusted for stock splits and reinvested dividends — the same convention used by major brokerages. A "year" scenario invests $1,000 at the prior December's month-end close and values it at the latest available month-end close. Non-USD amounts are converted at historical month-end exchange rates (Yahoo Finance): to USD on the buy date and back to your currency at the latest rate, so the return reflects the currency move as well as the asset.

    Month-end resolution means intra-month extremes are not captured in tables; the calculator uses exact trading-day closes where daily data is available. Figures ignore taxes, fees, and the currency effects of non-USD listings. History is not a forecast. Wall Street Regrets is entertainment, not investment advice.

    Full methodology →

    What if you'd held…

    Data: adjusted close prices via Yahoo Finance. As of 2026-08. Not financial advice.