Win Monopoly Every Time – 6 Simple Tricks

You probably played Monopoly many times, without thinking too much into what you are actually doing, just trying to have fun. Perhaps you were more successful than others, perhaps less, or maybe you didn’t even care as long it was a good time spent with friends. But if you’re more of a curious type, you possibly asked yourself how can some players win monopoly almost every time they play?

If you are interested in the history of Monopoly, you can find out more on Wikipedia.

Win Monopoly Every Time header

How to Win Monopoly Every Time?

Although luck plays a large role in monopoly, there is plenty of skill involved. Below are the 6 most important elements:

1. Owning Real Estate Is The Best Investment

Properties are the key asset in Monopoly and you should strive to own as many as possible. Don’t save your money – buy, buy, buy. It means that you have more property – and it means your opponents have less as there is a limited number of them available.

At the beginning of the game, you should buy every property you possibly can. This is especially true for the properties you can get a monopoly on or can prevent other players to get a monopoly. Mortgage properties that you currently don’t need, if you have to.

2. Three Houses Are The Best Kind Of Houses

As soon as you get your first monopoly, spend everything on houses – including mortgages. If you look at the property card, you’ll notice there is a big difference in rent from two to three houses, so three is the number you should be aiming for on your properties. When you have three houses, you are better off spending your money on another color.

You should upgrade to four houses later on, but don’t build hotels. Hotels are your enemy because they free up the houses for other players. Only build hotels, if you can also build those houses on other properties.

There are 32 houses in a standard set of Monopoly, and you should aim to lock down as many of them. If you have 24 on board, that only leaves 8 to your opponents – guess who is going to win that game?

Win Monopoly Every Time buildings

3. Being Locked Up Is Not That Bad

If you were ever in prison (hopefully you don’t have that experience), your first natural instinct was probably (I say probably, because I don’t have jail time experience myself) that you should try to get out as soon as possible by any means possible.

Many people make the same mistake in monopoly because they feel jail has excluded them from the game and they want to keep playing. They understand “playing” as moving on the board, while you should understand “playing” as collecting the rent and not having to pay any.

So, relax, stay in jail for as long as possible, and collect rent without any danger of paying one.

There is one exception to this rule though. At the beginning of the game, before you have any monopolies and plenty of property is still for sale, you should get out of jail as soon as possible and continue to buy.

Win Monopoly Every Time miniatures


4. Orange Property Is Prime Property

What? You always thought the best property in the game is at the end of the board, those two super luxurious tiles? That’s a popular fallacy (and the one you can use profitably when trading).

Statistically, jail is the most visited tile, and when you move out of jail, 7 is the most common roll of the dice. This lands you right in the middle of the orange. Combine that with relatively cheap housing, and you get the most profitable tiles in Monopoly.

Of course, you won’t always have the luxury of luck to own orange:  red is second best. Then, the further away you go from there, the worst off you are.

As a rule of thumb, use properties on the second and third sides of the board as your prime source of income.

5. Trade

The first player to have a monopoly (all properties of a certain color) has a big advantage over others and you should do everything in your power to be that player. Even though the orange is best, having a purple monopoly is still better than having no monopoly.

Remember all those properties you bought at the beginning? They are gonna come real handy in negotiations. It’s fine to give monopolies to other players, as long as you get a better one. And with the knowledge of prime properties, you can get a better deal, while making the other side think they got the better deal.

It’s a win-win scenario, only it’s a win for you … and another win for you.

Remember that you can still trade and negotiate, even when it’s not your turn. Besides collecting rent, that should be your main off-turn activity. Use all of your selling tricks – it’s what makes monopoly fun – and it will pay dividends.

Win Monopoly Every Time money

6. Be Ruthless When Collecting Rent

When someone visits your property, you have the upper hand – use it. Insist on accepting cash only. That will put a lot of pressure on the person paying (especially if they are tight on cash).

When they start to offer their property to other players to pay off the rent, and if that would give the third party a monopoly, that’s when you can start considering accepting property.

Just keep in mind that your goal is to bankrupt the other player(s) eventually. When you say “cash only” and you sadistically observe them scraping for funds, you know that this game is yours.

Win Monopoly Every Time cards back

Luck Still Plays a Part

Even if you do all the things right, there is still no guarantee of winning. A couple of wrong dice rolls and everything goes down the drain.

In that case, stay calm. Luck is something you have no influence over. Derive your pleasure from knowing you did everything right and you can’t win every time. After all, who is going to play with you if you win Monopoly every time?

Have you tried any of the mentioned strategies yourself, even without knowing you do them? Do you have any strategies of your own? Let me know in the comments below.

Check out my top 5 monopoly editions.

10 thoughts on “Win Monopoly Every Time – 6 Simple Tricks”

  1. Owning estate is definitely the best investment in monopoly. Whenever I’m playing it, I try to own as much as I can because I know it would later on tell on the game. These tips are spot on and definitely will help any individual to win more when playing monopoly. Another top tip that I found helpful is the collection of rent and being very brutal with it. Surely, those will help improve my performances in monopoly. Thanks for sharing these simple but very powerful tips

  2. This is a really great niche! I couldn’t have ever thought of it. There are so many board games and video games available to the public that most people get confused on how to actually play them. Thanks for the quick and short introductions and explanations! I love your Monopoly post a lot!

    • That’s exactly what I’m trying to do – to introduce people to board games, but also to give them another perspective to them, like ways to to get better.

  3. I have played monopoly a couple of times and the truth is I never won. It’s funny but it’s the truth. As that,I tagged it as a bad game for me and it wouldn’t help me mentally. Lol. Having read your post, I can see now that I have always played the game a wrong way. I want ruthless when collecting rent and I was always sloppy. I think I have to agree with you that in a way, monopoly is a game of luck. I think I should try your tips still. Thanks!

    • It’s a game of luck yes, but there is plenty of skill involved. With these tips, you are guaranteed to do much better, so start winning. 🙂

  4. I have spent many many hours playing monopoly, I mean, it really is a fantastic board game, actually it is like being in the real business world of buying and selling, wheeling and dealing etc, when you think of the number of countries this game is played in and how many monopoly sets have been sold world wide over the years, it really is a game that has endured for generations and has been played and enjoyed by so many people for decades, there has also been many different variations of monopoly, however, next time I play, I will be sure to use the winning strategies that you have recommended here, I hope I can win, thank you for sharing.

    • I enjoy haggling and negotiating over properties the most. And then when you finally have your monopoly with houses built and someone visits them … happy times! 🙂

  5. Monopoly is one game that help you learn how to manage your limited money, invest and make more money. Although I kept laughing as I was reading through this really nice post. My son have been the domineering champ in the house when it comes to monopoly and his streak doesn’t seem like its ending anytime soon. I’ll love to beat him in monopoly someday using these tips I have gotten from this post.


Leave a Comment

Our website uses cookies to provide the best experience for the user.


Test your board gaming knowledge: