How To Win At Monopoly Every Time – 16 Best Strategies To Use

Looking for the edge in the family game night? Or just sick of losing to that person who always seems to get all the luck?

If you’re in need of a sure-fire Monopoly strategy to secure the W then read on – I’ve picked the 16 best Monopoly strategies that won’t guarantee a win every time, but will definitely make sure you have a much better chance.

What is the best strategy to win Monopoly?

The best strategy for Monopoly is to buy the orange and red property sets and build 3 houses on them. Use other properties – including railroads – as ways to boost cash flow and trade high-value, low-return properties like the greens to secure the winning color sets you need.

Really, the best Monopoly strategy is a combination of different tactics, and a lot of it still relies on luck as well. So you need to have all of these tools and options available to you, and then you can pick the best strategies on the fly as the game unfolds.

1. Know The Rules Inside and Out

How do you win at Monopoly? If you don’t even know the rules then you have no chance – you can make some serious mistakes if you aren’t aiming for an actual win condition. 

The first thing you should do is make sure you’re fully aware of all the main rules of Monopoly, including auctioning, trading, buying properties, and mortgaging.

This also means making sure you fully know the rules that most people get wrong with Monopoly, because that way you can stop your opponents from doing something they shouldn’t be doing – something which could cause problems for your own game plan.

Once you have the rules sewn up and you can quote them with ease, you’ll be able to use them to your advantage. 

That doesn’t mean bending them (although I’ll come onto that), but it just means you’ll always be able to get the right rent payments from other players and you’ll know the best ways to escape from tricky situations without having to declare yourself bankrupt.

2. Acquire Properties Early

While it’s true that some Monopoly properties are better than others (jump to point 3 if you want to skip ahead), one of the worst decisions you can make in the game is to save your cash in the hope of only buying the properties you really want.

It’s instead really important to be picking up properties early, as soon as you land on them. Within your first few turns, you should land on at least 2-3 properties, unless you’re seriously unlucky, and these can form the basis of your early-game tactics.

Plus, if your opponents land on properties they don’t want, you can win them in auction and hopefully get them for cheap.

I don’t mean you should blow all $1500 on your first go-around of the board, but you’ll want to have some properties early – they’ll start accumulating you small amounts of rent, and they’ll be handy bargaining chips to use when the trading element of the game kicks in.

3. Aim For The Best Properties

Not all Monopoly properties are equal, and it might surprise you to learn which are the best in the game. Because it’s not as simple as just aiming for the most expensive properties, since they earn you the most rent.

Instead, you need to bear in mind ROI – Return On Investment. Those are the properties that give you the most money back in exchange for how much you have spent buying and upgrading them. 

ROI changes depending on how developed properties are, but across the board, the Orange set is one of the best. It’s never the absolute best for ROI – Dark Blue wins when undeveloped or with 3 houses, while surprisingly Light Blue has the best ROI for hotels.

But the orange set has another benefit – it is the most landed-on set in the game, meaning a higher chance of getting the rent payments. 

The Red properties are another good choice. They have middling ROI (though avoid hotels, not worth it) and they’re the second-most landed on set in the game.

4. Have A Plan B

This strategy goes hand-in-hand with point 3 above. While it is always best to aim for the orange properties, and then the reds or the dark blues to maximize both the chances of players landing on your properties and the money you can make, sometimes that just won’t be possible.

If another player ties up two oranges and two reds, you’re going to struggle to make a convincing offer to take them from them.

So the important thing to do is to have a Plan B in mind.

Work towards completing your primary sets, but if luck isn’t falling your way, have another two colors in mind.

Light Blue, Pink, and Yellow are good middle-of-the-pack choices in terms of both luck and ROI. Yellow will earn the most money of the three but the odds of players landing on them are slightly lower.

Ultimately the property sets you should be making your lowest priorities are the Brown and Green color sets. Green is too expensive, and you just don’t get the ROI that they deserve, while Brown is low value.

That being said, you can still win a game of Monopoly if you own these color sets and you follow the rest of the strategies in this guide.

5. Buy The Utilities

The Utilities in Monopoly have something of an odd reputation, and in fact when I was putting together this strategy guide I looked at what some other players thought and this was definitely the tactic that split opinion the most.

Some people argue you shouldn’t bother with the Utilities while others think they’re a good value pick-up. I’m in the latter camp, and here’s why.

The Electric Company and Water Works are relatively low cost at $150 each. Their rent rules are unique in that they vary depending on the dice roll used to reach them – the roll is multiplied by either 4 or 10 depending on whether you own one or both.

You want to aim to own both because then the average number of dice rolls needed to get your ROI is 79, which isn’t bad really – that’s taking into account the luck of players landing on the spaces, and the average rolls to do so.

If you have a 4-player game then it’s only 20 turns each, which most Monopoly games will reach. So the odds are in your favor of making a profit.

But also they’re useful backup plan properties – you can use them later in the game for mortgage cash, or to trade, and potentially most importantly they become ‘free’ spaces for you to land on if other players have built up dangerous color sets around them.

Sometimes just owning a cheap property can be a lifesaver late in the game, if you get lucky with your rolls. So I would still buy them – they’ve got a lot of flexibility in how you use them.

6. Buy The Railroads

In terms of ROI, the Railroads have some of the best potential on the whole Monopoly board – provided you can get hold of all four of them.

With the Monopoly Railroads, the rent that you can charge increases with each one that you own. So the more you have, the more you’ll charge each turn – either $25, $50, $100 or $200.

The goal is to get to owning all four, because then every time a player lands on a Railroad, you’re earning $200. And you will have only paid $800 to acquire all four. So within 4 landings, you’ve made your money back and can start turning a profit.

And while many people don’t view them as a property set, they are really – and the only set in the game with four spaces, so they have a higher chance of players landing on them. In fact, if you can own all four Railroads, it should only take 35 dice rolls to make your money back.

Plus, again, late in the game they can be valuable rest spaces to avoid other players’ color sets. So definitely make the Railroads a priority if you can.

7. Be Strategic With Trades

If you want to know how to always win Monopoly, you’re going to need to get good at trading. It is virtually impossible to always land on the properties you want to buy, which means other players are likely to end up with specific properties you need in order to complete a set and execute your strategy.

To take it from them, you’ll need to be able to make sharp trades that don’t always represent the best face value, and yet that can ultimately lead to a seriously advantageous position for you.

The best trading strategies for Monopoly involve acquiring high-value properties that you don’t intend to complete a set for. This is why you should still look to buy the Greens if you land on them, and definitely the Dark Blues.

If you can offer a Dark Blue to a player who doesn’t own the second Dark Blue, you can sometimes get two other properties in exchange – potentially even two Oranges. That could be a seriously smart way to boost your winning odds. Greens could even be traded in exchange for an Orange or Red and some cash.

Remember that cash and Get Out Of Jail Free cards can be traded, but houses and hotels cannot – so consider all your tradable assets when making deals.

8. Keep An Eye On Your Opponents

You can’t win Monopoly if you don’t keep tabs on what your opponents are doing. If you only focus on yourself then you’re putting yourself at a massive disadvantage.

There are a few things you need to be looking for when analyzing your opponents’ play:

• Are they getting close to a color set that you own, and is it worth building up those properties due to the higher chance of them landing on one of them?
• Are their cash levels low, and do you have the chance of doing some serious damage/potentially wiping them out of the game with a power move?
• Do they seem to know the best strategies themselves or are they aiming to complete some of the less-useful color sets?

All of this is useful information that can influence your moves. Remember that players should always have their cash available for other players to see – not necessarily super-clear but at least giving an indication, and hiding cash is cheating.

Don’t be afraid to call it out.

9. Keep Some Cash On Hand

While it can be tempting to go all-in on a color set and build as many houses as possible, especially with players approaching, you need to be careful and keep some cash reserves on hand.

You never know when you might just get unlucky, and have the other players miss your built-up set while you land on one of theirs that has a couple of houses on it.

While you can mortgage properties if you need to, you’ll just be throwing away money due to the interest you’ll have to pay to unmortgage them. This is a useful tactic to have if needed but ideally, it shouldn’t be necessary.

So keep some cash in hand at all times, just in case you need it before you get back around to Go.

10. Relax In Jail

In the latter stages of a Monopoly game, the board can become extremely hazardous. Most of the properties may be owned as part of a set with at least a couple of houses on them, which can make every roll of the dice treacherous. You’re almost hoping to hit Chance and Community Chest or Free Parking to avoid paying huge sums to other players.

This is where Jail gets interesting.

According to the Monopoly Jail rules, you’re still very much an active player while you’re in Jail. You can still trade, mortgage and unmortgage properties, and crucially you can still collect rent.

So why, if the board is mostly owned, would you want to get out of Jail as quickly as possible? Instead, you should be taking as long as possible in there, always taking the full three turns and trying to roll doubles.

The only advantage to moving around the board in late Monopoly is to pass Go, but often you’ll spend more from the rent you pay. So take advantage of the breather that Jail offers.

11. Build Smart

Building houses and hotels in Monopoly is not a race to see who can get to a hotel quickly.

In fact, in most cases, hotels aren’t actually the best option! 

When we’re purely talking about Return on Investment, the optimum level for most color sets is to build three houses on each property. Three houses will usually see a significant jump in rent you can charge from having two houses, but you aren’t paying the high fees to get to four houses or a hotel.

Also, some experts will tell you to build as quickly as you can in Monopoly, but I say that comes with a caveat – only build if you definitely have the cash.

If you have to mortgage a property, you only ‘lose’ the interest payment of 10% when you mortgage it back.

If you have to sell a house back to the banker, you only get half the value back. So you’re wasting 50% of the cost of a house or hotel every time you buy and then sell it.

So yes, buy houses when you can, but only if you can definitely afford them. Selling houses is a sign you’re in trouble.

12. Use Mortgaging Strategically

A lot of players are reluctant to mortgage properties in Monopoly except as a complete last resort. They will only do it when they are about to lose the game and need to get some desperation cash to pay off a large rent bill.

And yes, I agree that it’s frustrating to have properties that you own that aren’t collecting rent, but it shouldn’t be exclusively a last resort.

There are some situations where mortgaging earlier can be useful:

• When you’re only buying a property to prevent another player from getting a color set, and you want some money back
• When you’ve bought a property purely for trading value, especially since the other player is forced to pay 10% or 20% interest when they take it from you, depending on when they unmortgage it
• When you want to build houses on a color set and need some spare cash

Don’t be afraid to mortgage properties. Remember that they’re still useful to own as a ‘free’ space to land on, even if they’re also a free space for other players too.

13. Avoid House Rules

Monopoly is famous for having all kinds of house rules – subtle tweaks or adjustments to the main rules that players either mistakenly believe are official, or that are seen as being more fun.

An example is throwing your fines in the middle of the board to be won by whoever lands on Free Parking. That’s not a real rule!

Here’s the thing though – the standard rules of Monopoly are almost perfectly balanced. And if you start changing them, the game can become pretty messed up, particularly from a strategy perspective.

If you play a game using house rules, then a lot of the strategies in this guide won’t work. Try to convince the players you’re up against to stick to the main rules if you want the best chance of success.

14. Target Weaker Players

Monopoly games are rarely balanced. By the time the color sets are sewn up and players are building houses, there tends to be one or two players who are in a position of strength, with the rest lagging behind as underdogs.

Hopefully, by following the tips in this guide you’re one of the players in a good position, and then it can become tempting to target your main rival to try to take them down. Don’t! Target the weaker players instead and try to wipe them out of the game.

If you can bankrupt another player using your own properties, you’ll take everything they own from them. Make sure you build houses as the weaker players get close to your color sets, and you can significantly boost your portfolio.

This is the best way to win – you’ll get stronger, and also prevent your main rival from increasing their own winning chances.

15. Form Alliances – But Don’t Be Afraid To Break Them

A controversial one, but it is possible to team up with other players and form an alliance. This won’t always be suitable, but sometimes it can help to give each other advantageous trades.

The only time I would be 100% against alliances is if you’re playing a three-player game. That’s not fair on the third player, no matter how strong they are.

Unless they’re a parent and the other two players are kids. Or they’re a jerk. Then, go for it!

Technically you could cheat with an alliance by not charging rent. According to the official rules, rent must be asked for, so if you don’t ask for it from your ally, they won’t have to pay it.

But I think that’s too far. I would only advocate teaming up if you’re behind in a game and need to recover your position, and even then I’d play it by the rules.

Having said that…

16. If All Else Fails… Cheat!

I know, I know, this isn’t really a ‘strategy’ for winning at Monopoly, but if you’re having issues winning and the other players are too strong, there are several sneaky ways to cheat.

I wouldn’t really advocate it – it’s always better to win fair – but sometimes (if you’re playing with friends especially) you can have fun doing it and not upset everyone.

Sneaky ways to cheat in Monopoly include:

• Stealing money from the bank
• Moving the incorrect number of spaces
• Bribing players with real-life rewards.

And you’ll find a whole lot more ways here.

Get creative – just don’t get caught!

The Bottom Line

So, is there a strategy to Monopoly? Well, not one single one – you need to make use of everything I’ve included above.

The best way to win Monopoly is to know the rules, because if you don’t know what is and isn’t permitted, then you can’t make sure that your opponents don’t take liberties (intentionally or not), and you can’t make use of the other tactics in this list to their full effect.

No two games of Monopoly are the same, and so you can’t guarantee that you’ll always have a clear and easy route to victory, even using the strategies in this guide. But if you make sure you know these tips then you’ll be able to make much more informed decisions during tense, quick-thinking moments. And more often than not, that’ll help you secure the win.

It’s also good to understand some of the key Monopoly statistics that tell you the odds of certain events happening – that way you’ll know whether a Hail Mary play is worth a try or if you’re better changing things up and playing it safer.