How To Win Monopoly - Full Guide

In this post, I’ll be showing you how to win the infamous friendship-ending money game, Monopoly. As a dice-heavy game, there’s a lot that’s out of your control - however there are a lot of things within your control that can radically improve your chances of winning. To the point where if your opponents don’t know them, you’ll probably win just about every time.

I should note that I did quite a bit of research discovering strategies from competitive monopoly players, articles, and even other strategy videos like this one. You can find a list of links to all of my sources in the description below.

So when analyzing games with a healthy dose of chance, I like to categorize elements of the game into things that are out of your control, and things that are in your control. A lot of people get frustrated with Monopoly because of all of the game-changing things that are out of your control. Don’t let those get to you. Understand what you can control and capitalize on those.

So in Monopoly, you can’t control what you roll, but you can understand probabilities and what they mean for where you and your opponents are likely to land. You can also control what you choose to buy and whether or not you start an auction when you land on a vacant property. You can’t control when you go to jail, but you can influence how long you stay there. You can’t control landing on opponents’ properties, but you can control how much money you keep on hand and when to strategically spend that money on things like houses. You can’t prevent frustrating things from happening to you in Monopoly, but you can (for the most part) control your emotions and keep a level head. And of course, there’s a lot within your power when it comes to selling, trading, and negotiating in this game. The social strategies.

Probabilities

First let’s talk about strategies related to understanding probability. Since you roll 2 dice in Monopoly, the most common number to roll is a 7, then a 6 or 8, then 5, or 9, and so on. You’ll notice that dice rolls between the range of 5 to 9 account for ⅔ of all possible rolls.

Due to chance cards sending you to jail, or others that direct you to specific areas of the board, there are specific spaces that are just more likely to be landed on. Since jail is the most common space for players, the orange properties are the best real estate on the board. Followed by red. In fact, all of the spaces after jail and before “go to jail” are pretty solid. This is called the “hot” side of the board. Always prioritize properties on the hot side. Naturally the other side of the board is the “cold” side.

Pro Monopoly players (yes there are pros) swear by this heatmap. Memorize it. Become one with it. All of your haggling and mortgaging should be done with the goal of controlling the most you can on these high-probability spaces.

Speaking of probabilities, the likelihood of drawing specific chance and community chest cards is something you can predict. If you’re feeling particularly saucy, you can memorize these cards and keep tabs on them throughout the game. Knowing what’s left in the deck can help you predict where the next card is going to take you or your opponent.

What You Buy

Next, let’s talk about what to buy. A simple rule of thumb is to buy everything you land on - except utilities. Those are pretty much trash. Railroads are also not that great unless you can get all 4 - which most people won’t let you do. They’re still decent… but with properties, you should basically buy all the ones you land in. This is a game of control after all. Buying properties early, even if you’ll likely need to mortgage them is generally a good idea. You prevent your opponents from owning them and you have bargaining power for later in the game when you’re trying to trade to get Monopolies.

On that note, you don’t always need to buy properties at face value. Commonly auctioning is actually a good idea, especially since you can still bid on the property. In this light, you need to use auctions strategically. On one hand, you might get the property for cheap. On the other, the price might go far above the normal price. This can work in your favor if you put properties up for auction that you know your opponents want so you can bleed them out of their cash. Remember your goal is to bully each opponent into bankruptcy. Pushing them to their limits with an auction can increase the chances of them landing on a space that deals that final blow.

Jail

Okay another aspect of Monopoly that’s in your control in managing your time in jail. In the early game, it’s critical that you’re buying properties, so at this point it’s usually a good idea to use bail or get out of jail free cards. Especially if it increases your chances of getting an orange or red property. You gotta get out there and buy stuff. In the late game though, you’re usually better off just hanging out in jail. You don’t want to be moving around the board when most or all of the properties are already owned. It’s a dangerous world out there and being forced to move wherever the dice take you can lead to painful consequences.

Spend/Save Money

Okay, my next strategic category for Monopoly is about spending and saving money.

Regarding spending, one of your top priorities should be to start building houses faster than your opponents. Specifically getting three on your monopolies is a critical goal to have. The rent goes way up, and the more houses you own, then less your opponents do. In fact, it’s important that you create a scarcity of houses. The rules themselves state that once houses are gone, nobody can build more until they re-enter the bank. In this light, you should rarely buy hotels. Doing so puts houses back in the pool, allowing your opponents to grow. You also should mortgage properties before ever considering selling houses. In a good game of monopoly, you should never sell any houses. Keep that scarcity high for your opponents. If you own all the houses, everyone else is just… stuck. This can be especially frustrating for your opponents when they have monopolies but can’t really do very much with them.

So in this light, once you have a monopoly, it might be a good idea to mortgage any other properties you don’t plan on maxing out so you can buy houses as fast as you can.

The timing of buying houses also matters. If you’re going to spend money just to put houses down where none of your opponents are, it might not be a good idea. Wait to put those houses down until you see your opponents are between 5-9 spaces away from where you plan to build them. You can preemptively invest in these things, maybe even mortgaging if you need to, so you can time the placement of those houses and suddenly hit your opponents harder than they expected.

Another simple rule of thumb with houses, is to always have enough cash on hand to pay the top rent on the board if you happen to land on it.

Emotions

Alright the next category is pretty simple. Emotions. Keep calm throughout the game. Understand that the dice will not behave. Don’t go into turns hoping not to roll a 10. Just throw the dice and roll with whatever happens. Keeping your cool will help you logically reason through your options and you’ll avoid making poor decisions based on emotion, anger, or frustration.

Social Strategies

Finally let’s look at social strategies. It’s very unlikely you’ll get monopolies without trading or buying properties from your opponents. With this in mind, it’s important to be likeable so people are more willing to trade and negotiate with you. Sometimes it can be advantageous to intentionally not charge rent. The rulebook states that you really don’t need to, and being nice like this can form alliances.

And speaking of collecting rent, the rulebook states that the owner “may not collect rent if he/she fails to ask to ask for it before the second player throws the dice.” It doesn’t say “forgets” it says “fails.” So here’s a shady social strategy for you. Try to distract people while your turn is happening. Get them talking about something other than asking for rent. All you need to do is get the next player to throw the dice before rent is asked and you’re safe. Is it honorable? Not really. Blame Hasbro for intentionally baking this loophole into the rules.

Okay and the last social strategy is how to approach trades. Being likeable is nice and all, but in competitive games, that’s not going to be enough to get good trades. You gotta provide value to your opponents. So with this in mind, generally people only trade or buy from each other if it gets them closer to a monopoly. This is great, but only surface-level. Remember that houses are the real game changer, so you might make trades or sell properties that on the surface don’t make sense for you, but they give you enough money up-front to buy houses before your opponents. Maybe you even intentionally let your opponent get a monopoly knowing that the trade will ultimately get you houses faster and further deplete the house supply. They get a monopoly, but can’t really do a lot with it if there aren’t houses for them to buy in the bank.