Massachusetts Multifamily Investor & General Contractor — Looking to Connect With Inv

Boston, Massachusetts
Multi-Family and Apartment Investing
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Massachusetts Multifamily Investor & General Contractor — Looking to Connect With Inv

Matthew Bailey
Rental Property Investor · Boston Ma · Member since 2025 · 7 posts · 2 votes

Hi everyone,

I’m Matthew Bailey, a Massachusetts-based real estate investor, general contractor, and business owner.

I currently own or co-own five investment properties, including multifamily buildings and other income-producing residential properties.

My background includes extensive experience in construction, property renovations, acquisition analysis, rental management, and identifying opportunities to increase property values.

I’m looking to expand my portfolio by acquiring additional multifamily properties and apartment buildings throughout Massachusetts and New England.

I’m particularly interested in connecting with experienced real estate investors and established investment groups interested in long-term joint ventures.

I bring hands-on construction knowledge, property management experience, and an existing investment portfolio to potential partnerships.

I’d love to connect with investors who are actively acquiring multifamily properties or looking to establish relationships with experienced local operators.

looking forward to discussions

Matthew Bailey

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Ali NajjarBusiness Member
Lender · NJ · Member since 2025 · 66 posts · 28 votes
1w

Hey Matthew, I’m a lender but figured it’s still worth a connection. Good luck with the search in Massachusetts. Happy to be a resource on the financing side when a deal comes up.

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  • Lien VuongBusiness Member
    Real Estate Agent · Boston, MA · Member since 2018 · 2k+ posts · 1k+ votes
    1w

    Hi Matt! Thanks for the warm intro! Where in Boston area do you invest in? Happy to connect as we look seek to expand our portfolios across New England - feel free to DM!

    [email protected]
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    • Matthew Bailey
      OP
      Rental Property Investor · Boston Ma · Member since 2025 · 7 posts · 2 votes
      1w

      Hi,

      I would love to connect. I’m open for any and all conversations!

      1Reply
  • Gregory AcsPro Member
    Lender · MD · Member since 2025 · 244 posts · 91 votes
    1w

    Great background, Matthew. Having both construction experience and an existing rental portfolio puts you in a strong position to evaluate multifamily opportunities.

    For larger acquisitions, having the right financing structure alongside reliable investment partners can make a big difference in how quickly you scale.

    Are you mainly looking for equity partners on your next deals, or are you also exploring financing options for larger multifamily acquisitions?

    0Reply
    • Matthew Bailey
      OP
      Rental Property Investor · Boston Ma · Member since 2025 · 7 posts · 2 votes
      1w

      Hey,

      Looking for an equity partner at this time yes.

      0Reply
  • Inder Singh
    Real Estate Agent · Boston, MA · Member since 2025 · 48 posts · 17 votes
    1w

    Welcome to BP, Matthew. A GC who also owns and operates multifamily is the exact combo a lot of buy-and-hold investors are hunting for right now — good contractors are the bottleneck on almost every deal I see.

    I'm an investor-agent licensed in MA/RI/NH with 17 units of my own (buy & hold multifamily in Worcester, Warren, and Revere), so I sit on both sides of the table. I'm always looking at multifamily in Worcester and across central MA — happy to compare notes on underwriting or share what renovation costs look like from the owner side.

    If you're open to talking deal flow or JV structures, my DMs are open. Good luck building out here.

    0Reply
    • Matthew Bailey
      OP
      Rental Property Investor · Boston Ma · Member since 2025 · 7 posts · 2 votes
      1w

      Hey,

      Absolutely! I’m free to chat and would like that very much.

      0Reply
    • Inder Singh
      Real Estate Agent · Boston, MA · Member since 2025 · 48 posts · 17 votes
      1w

      Glad to hear you're open to chatting, Matthew. Quick peer intro since we connected here: I started buying in Revere back in 2020 and now hold 17 rental units across MA, including Worcester and Warren, and I'm a licensed agent in MA/RI/NH with Candor Investment Group (eXp Realty).

      The investor-GC combo is exactly the profile I like partnering with — it takes the rehab guesswork out from day one. Since you're open to equity partners, I'd love to compare notes on deal flow and how you like to structure JVs on multifamily deals.

      My DMs are open — want to hop on a call this week?

      1Reply
    • Matthew Bailey
      OP
      Rental Property Investor · Boston Ma · Member since 2025 · 7 posts · 2 votes
      1w

      Hey,

      Feel free to give me a call 857-312-3935

      0Reply
  • Ali NajjarBusiness Member
    Lender · NJ · Member since 2025 · 66 posts · 28 votes
    1w

    Hey Matthew, I’m a lender but figured it’s still worth a connection. Good luck with the search in Massachusetts. Happy to be a resource on the financing side when a deal comes up.

    Quicker Home Loans527 Reviews
    WebsiteView Page
    1Reply
    • Matthew Bailey
      OP
      Rental Property Investor · Boston Ma · Member since 2025 · 7 posts · 2 votes
      1w

      Hey, thanks for message. Certainly will save your info if needed

      0Reply
  • Quetzaly TorresPro Member
    Investor · Jacksonville, FL · Member since 2026 · 51 posts · 6 votes
    1w

    Matthew, with your construction background and existing portfolio, are you primarily looking for partners who can bring capital, or investors who can bring you more acquisition opportunities?

    Also, do you come across off-market multifamily deals that don't necessarily fit your own buy box?

    I'm connected with an investment group looking at multifamily acquisitions, so there could be some interesting opportunities to collaborate...

    0Reply
    • Matthew Bailey
      OP
      Rental Property Investor · Boston Ma · Member since 2025 · 7 posts · 2 votes
      1w

      Hi,

      Looking for partners who can bring capital. Would love to chat.

      0Reply
  • Matthew MorrowBusiness Member
    Investor · PA - NY - NJ · Member since 2019 · 853 posts · 301 votes
    1w

    @Matthew Bailey welcome. Being a GC who also owns is a strong combo, since you can underwrite a rehab better than most people. With that background you could be an amazing resource for a lot of people on here. We work mostly in PA, NJ, and NY, so not your backyard, but always good connecting with other investors.

    [email protected]484-791-6200
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  • Levi Rawlings
    Real Estate Agent · Portland, ME · Member since 2021 · 9 posts · 3 votes
    1w

    Welcome, Matthew. Being both the GC and the operator can be a real advantage. On the acquisition side, for older New England 2–6 unit buildings, the controlling question is often whether the in-place rents carry the debt before any renovation upside is counted. Deals that only work after the rehab put most of the risk on execution. With your background, it sounds like you'll be able to evaluate this easily.

    I'm always happy to chat through a deal. I work for a real estate development company active in New England, so we can also provide some insights on buildable potential on deals you're looking at. That's one way to drive significant value when purchasing at reasonable market rates.

    0Reply
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