@Sean Maiden as others have mentioned I think your best bet is to find a multi family house (preferably 3 units) and house hack. You can rent out the other units and also try to get some buddies to rent out a bedroom in your own unit.
Have you spoken to a bank yet to get pre-approved? If you tell the bank what you are looking to purchase (an owner occupied multi family property) I think you would be pleasantly surprised that you can afford a higher price point. As Charlie mentioned, the bank will take into account 75% of the projected rents of the property and add that # to your income which will increase your purchasing power (I wouldnt be surprised if you could get pre-approved for a price in the $400s or $500s, although I dont know your full profile including credit and income). Also, keep in mind as an owner occupant you would be able to put less than 20% down on the purchase.
You may not find a situation where you will cash flow very much (you may even still have to pay a couple hundred bucks/month) but at least you are now owning a property, not throwing a large chunk of your money away in rent (assuming you rent now), your tenants are paying down your mortgage, you are gaining equity each month and gaining tax benefits. You will be able to add to your savings each month to use towards a future purchase. If your house gains equity over the years you could pull out some equity to use as a down payment towards your next house hack and repeat the process while backfilling your previous unit with a new tenant with the goal of turning the original property into a positive cash flowing property.
For starters I would suggest playing around with mortgage calculators under different scenarios to see what the monthly payments would look like at different price points, down payments and projected rents (dont forget to add in taxes, insurance, repairs/maintenance etc) and then speak to some local community banks or credit unions to see what sort of pre-approval you can get up to. Once you have a solid pre-approval you can begin to consider towns that may work (off the top of my head I think Framingham, Marlboro are two solid areas that could possibly work and gives you a decent commute). I think the biggest problem you will find is the majority of the inventory will be 2 families making it more difficult to make the #s work and majority will need some sort of work/cosmetic upgrades.
Bets of luck and if you need help getting into any properties let me know.
-Nick