New Member - South Boston

9 Replies

Hi All,

My name is Blaine.  I currently live in Southie and work in Newton.  My wife and I are taking the first steps to investing in Real Estate.  We have very demanding, time consuming jobs, so we think buy-and-hold rental properties are a better fit for us than wholesaling, flipping, etc.  Like everyone else, our goal is to generate enough passive income in the next 5-10 years for one or both of us to escape the corporate rate race.  We have little-to-no experience, but we have been studying some of the recommended books on here and listening to the BP podcasts.  I also have a single family rental property in Atlanta.  It was my primary home and it is now rented out and handled by a property management company.  There isn't a lot of cash flow in it, but it has allowed me to build equity as the real estate market begins to recover down there from the recession.  That's primarily the extent of our experience.

Our goal is to buy 2-3 multi-family properties per year.  We'd love advice on how best to get started and the common pitfalls to avoid.  We are looking in the Dorchester, JP, East Boston, Malden, Everett and Chelsea markets.  How do people feel about these areas?  Is it possible to find cashflowing properties for $500k or less?

Thanks in advance for the advice.  Look forward to getting to know everyone on here.



Welcome Blaine! We have a real estate company and dog walking company in Southie. We lived there for 8 years before moving to the Savin Hill part of Dorchester. I actually joined Biggerpockets because of all of the development that is happening in South Boston. The amount of 3 family condo conversions really interested me so after doing some searching online, I found my way here.

You can certainly find multi's in those neighborhoods at that price range, many of which are on the MLS. Another avenue would be to purchase an absentee owner list from Listsource and see if any of them are interested in selling. The networking events are key too!

There is a strong community here in MA. I would suggest attending the networking events in the area. @Ann Bellamy  has a great event called Black Diamond held the 4th Tuesday of the month in Waltham. @Justin Silverio  also has a great meet up at rehabs that he's done. Even if you aren't interested in flipping or rehabbing, the networking and people you meet will open doors for you. There was a gentleman at Justin's last event that will be having an event specifically for multi-family investing. I don't remember the dates off the top of my head but I'm sure Justin knows.

You should also join Meetup and join the different investor groups. They are always holding events and you can acquire properties through the people that you meet and learn more about buy & holds. Boston Wealth Builders is a great group on Meetup and I believe focus on the Dorchester area.

In the past couple of months that I have been on BP, I have learned a ton from listening to the podcasts and reading through the forums. I've also met many of the key players at the networking events. The BP community is fantastic because everyone is here to help other out.

Best of luck! Feel free to reach out to me if you have any questions or are planning on attending a local event :)


Hi Blaine, welcome to BP.

This is a great place to learn. Make sure to listen to all the BP podcasts, read the articles on the main blog and be active in these forums to learn a ton very quickly about any topic in real estate you want to know more about.

This is also a great place to meet people that can be assets to your business. Lots of great connections all over but we also have a very strong and active contingent here in MA on here so make sure to find them (Set up some keyword alerts to find out about local topics) and get connected.

Besides doing that on here make sure to get out to some of the many local investor events we have, as Josh mentioned. He is on the money that Justin puts on a great event (His is quarterly so you will have to wait to December for the next one) and also the Black Diamond in Waltham is a must see. They actually have a 2nd location in Worcester that meets tonight. Probably to short notice for you but it is about out of state investing so you might get some useful information, or even better be able to contribute what you have learned. No better way to make strides at a meeting than contributing (Ditto for the BP forums FYI). Besides those there is also the Boston Area REIA in Medford which happens to be on Thursday. This month is just a networking meeting, but that can give you more of a chance to connect with people so not a bad thing at all (And I think she is providing some free appetizers. :) ).

As I'm sure you know you gave a bit of a range in the quality and desirability of areas, as well as long term development plays, but they all have merit.  Cash flow around here is usually pretty tough upon initial purchase unless you get a smoking hot deal, force a ton of appreciation (I.e buy a shell and put more into fixing it than you paid) or put down a really big downpayment to lower your financing costs.  What you do have here that a lot of markets don't is pretty consistent appreciation in both values and rents.  So you might just be scraping by at first but in a couple years your place might be worth 30-40% than you paid and rents may be up 20+% and off of a sudden you have a lot of equity and decent cashflow. 

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Hey @Blaine Page . Welcome to BP! I have a day job as well so it adds a layer of complexity to investing. However, you just need to be much more focused and create great systems. That's great that your wife is interested in getting into REI as well.

I'm happy to add you to my mailing list for my networking events.  Just PM me with your email address.  Also, I'll be speaking at the Real Estate SUCCESS event at Petite Robert Central in Boston on October 29th.  My presentation will be about how to invest while working a 9-5.  Here's the link to the event if you're interested -

Hey Blaine! Where did you live in Atlanta? I'm from there and that's where all my properties are (but I live in LA).

Have you thought about buying more in Atlanta or out-of-state? Boston is a hard place to make cash flow.

Welcome @Blaine Page  ! I am a newly-joined member of the site as well and already being welcomed by plenty of people. It is also nice to know another real estate investor in MA. I hope to talk to you soon.

Hey @Blaine Page  welcome to BiggerPockets! It is great to have you and please feel free to jump in the community - there are certainly great people around here!

And oh, learn how to use BiggerPockets to grow your business by checking this quick guide:

See you around!

@Blaine Page  Welcome Blaine 

BP is a great resource. Full of great tips and reads. One tip that I picked up here is while you are starting out and saving money for your investments, start driving / visiting areas you would like to invest in so you get a feel for prices, rents , house conditions etc, and visit and look at lots of homes and open houses so your eye get used to looking at repairs / upgrades that are normal in a particular market. I really dont think you can look at too many properties, and the more you look, the more knowledge you will gain for that market.

Boston can be a pretty expensive market, especially trying to cash flow on a buy and hold.  I would echo Ali's advice about looking at other markets.  There are forum posts about out of state investing and what markets to look at

Thank you all for your responses.  It is easy to see why BP is such a great community.  I really appreciate each of you taking the time to reply to my post and providing extremely helpful information.  We're already looking into the different area meetings and networking events that were mentioned, as well as reading the recommended BP articles.  We're really looking forward to being more involved on BP and hope to eventually meet some of you soon.

Thanks again!


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