Getting started in real estate in the Boston Area

Boston, Massachusetts
House Hacking
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Getting started in real estate in the Boston Area

Garrett Hirsch
Boston · Member since 2026 · 5 posts · 3 votes

Hi! I am looking to get started in real estate investing by using the house hacking strategy. I am 25 years old, living in the Greater Boston area. I'm very early in my process, so I would love to connect with as many people as I can to learn more about real estate. I'd appreciate any advice as well.

Thanks!

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Diana KhanPro Member
Attorney · 10451 Mill Run Cir #755 Owings Mills, MD 21117 · Member since 2024 · 398 posts · 154 votes
21h
Quote from @Garrett Hirsch:

Hi! I am looking to get started in real estate investing by using the house hacking strategy. I am 25 years old, living in the Greater Boston area. I'm very early in my process, so I would love to connect with as many people as I can to learn more about real estate. I'd appreciate any advice as well.

Thanks!

@Garrett Hirsch, house hacking can be a great way to get your first experience as both an owner and a landlord. Since you’re still early in the process, I’d spend some time learning what makes a property work as a rental before getting too attached to a particular deal. The numbers matter, but so does choosing a property you can comfortably live in while renting part of it out.

I’ve worked with newer investors who were excited about the purchase but didn’t initially think much about the landlord side of the plan. Things like the lease, how the property will be shared, and your responsibilities once someone is paying you rent are much easier to think through before you buy.

It’s great that you’re starting by asking questions and connecting with people, @Garrett Hirsch. I’m a real estate attorney and investor, and I work with landlords and investors regularly, so I always enjoy connecting with people who are just getting started. Happy to stay connected as you learn more about the process.

[email protected]240-266-0291
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  • Kasing Ng
    Accountant · San Francisco, CA | Remote · Member since 2026 · 70 posts · 37 votes
    22h

    Welcome Garrett, house hacking is a great way to start, someone else helps cover your mortgage while you learn.

    One tax thing worth tucking away early, since that is my world as a CPA: on a two to four unit, the side you rent out gets you write offs through depreciation even while you live there, and if you stay at least two years, a big chunk of the profit on your own side comes out tax free when you sell. Nothing to act on now, just good to know when you pick the first one.

    Good luck!

    1Reply
  • Diana KhanPro Member
    Attorney · 10451 Mill Run Cir #755 Owings Mills, MD 21117 · Member since 2024 · 398 posts · 154 votes
    21h
    Quote from @Garrett Hirsch:

    Hi! I am looking to get started in real estate investing by using the house hacking strategy. I am 25 years old, living in the Greater Boston area. I'm very early in my process, so I would love to connect with as many people as I can to learn more about real estate. I'd appreciate any advice as well.

    Thanks!

    @Garrett Hirsch, house hacking can be a great way to get your first experience as both an owner and a landlord. Since you’re still early in the process, I’d spend some time learning what makes a property work as a rental before getting too attached to a particular deal. The numbers matter, but so does choosing a property you can comfortably live in while renting part of it out.

    I’ve worked with newer investors who were excited about the purchase but didn’t initially think much about the landlord side of the plan. Things like the lease, how the property will be shared, and your responsibilities once someone is paying you rent are much easier to think through before you buy.

    It’s great that you’re starting by asking questions and connecting with people, @Garrett Hirsch. I’m a real estate attorney and investor, and I work with landlords and investors regularly, so I always enjoy connecting with people who are just getting started. Happy to stay connected as you learn more about the process.

    [email protected]240-266-0291
    1Reply
    • Garrett Hirsch
      OP
      Boston · Member since 2026 · 5 posts · 3 votes
      19h

      Thanks, Diana, happy to connect!

      0Reply
  • Nicholas FloydBusiness Member
    NY · Member since 2026 · 198 posts · 74 votes
    21h

    Garrett, you’re doing the right thing by learning and building your network before jumping into a deal. With house hacking, I’d focus heavily on understanding the numbers—purchase price, expected rents, taxes, insurance, repairs, reserves, and what the property looks like if one unit is vacant.

    I’d also talk with a few lenders early so you understand what you qualify for and what financing options are available before you start making offers. That way, when the right property comes up, you’re already prepared instead of trying to figure out the funding afterward.

    Keep connecting with investors, agents, lenders, contractors and property managers in the Boston area. The relationships you build now can make a big difference when you find your first deal.

    0Reply
  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
    10h

    Garrett, house hacking can be a great way to get started, especially if you’re willing to learn the numbers before jumping into the first property. Since you’re in the Greater Boston area, I’d focus first on understanding what your actual monthly housing cost would look like after rental income. Don’t just look at the purchase price, run the mortgage, taxes, insurance, maintenance, vacancy, and realistic rent for the other unit or rooms.

    I’d also spend some time learning how to analyze properties before worrying about finding the perfect deal. Once you can quickly tell whether a property works, you’ll be much more confident when something interesting comes along. And build your local network early. Agents, lenders, investors, contractors, and property managers can teach you things that you won’t get from simply looking at listings.
    Happy to connect!

    [email protected]941-914-7779
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    • Garrett Hirsch
      OP
      Boston · Member since 2026 · 5 posts · 3 votes
      4h

      Hi Ashish, thank you for responding!

      I'd like to ask a few follow up questions. First when you say "analyze properties" what exactly does that look like? Second, how should I be approaching lenders/agents when I don't have a set timeline on when I'd like to purchase a property? Thanks again for the help

      0Reply
  • Chris SeveneyBusiness Member
    Moderator
    Investor · VA · Member since 2015 · 21k+ posts · 19k+ votes
    8h

    As you know, Boston is a high-priced market but many of the surrounding areas hold their value very well. I would make sure to continue to save money for a decent down payment. Then as others mentioned, consider a house hack: whether you rent out another bedroom in the house or get a home with a basement and rent out the basement 

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