Where’s better to invest, CT or Western MA?

Question

I live in CT but am interest in determining if over the boarder in Wester MA is a better territory to invest in BRRRR. Anyone have experience in that area and any specific areas to consider or stay away from?

Kate L. · Answer

Yes, Berkshire County is basically CT border all the way up to Vermont boarder on the west side of MA. Both as an agent and an investor, I focus on south of Pittsfield and West of Becket.  Great Barrington, Lenox and Stockbridge were destinations pre-pandemic. Sheffield, Egremont, New Malborough, Monterey, Tyringham, Lee, Richmond and Sandisfield have picked up SINCE the pandemic. I should clarify, it’s a brrrr STR. Prices in Berkshire County are too high for long term rentals, at least south of Pittsfield.

Bill Keane · Answer

@Kate L.

So I am going to be so naive right now; when you say you’re brrrr’ing in the Berkshires, does that include towns near the CT boarder?? I’m clearly new to this whole area.

Bill Keane · Answer

@Jessica Sovronsky

Thanks for the local insight! This is why I love this community. Everyone, like you, is awesome. I’m definitely going to check this area out.

Kate L. · Answer

Working on a brrr now in The Berkshires. I must say, it’s not easy to « make money when you buy ». The market here is so hot. Even the ugly houses sell above asking. Cash is definitely king, but still… Staying in CT may be a good bet for now. Good luck!

Jessica Sovronsky · Answer

Sheffield MA is close enough and has a lot going for it. I can't say I've watched the market there, but personally I know people who have moved there because it's cheaper than, but still close to, Great Barrington which is a very popular destination and has a lot going on! I would say anything near Great Barrington is a good bet. Anything relatively close to Route 7 is prime, I believe, because that will take you right up and down the county, with access to everything from shops to mountain views!

Bill Keane · Answer

@Jessica Sovronsky

Thanks for the info! I can imagine the amount of action in the Berkshires. Do you recommend looking into any areas closer to the MA/CT boarder? I’m looking for both SFH and MFH.

Bill Keane · Answer

@Jordon Bell

Thanks for the encouragement! I agree with you on the opportunities still present in CT. I’m close to the MA boarder, over in Avon. I’m just curious if I can find some new territories in my radius that I’m not aware of.

Jessica Sovronsky · Answer

I lived in Western MA for 5 years, and the market moves FAST. There are a ton of flippers in the Berkshires. From knowing the area, I would say surrounding counties are probably cheaper and with less competition. BUT if you can buy fast I would say go for it! I know a flipper who made 100k on a house that hadn't been touched since the 70's. There aren't many of those left, but when you find them, they're lucrative!

Jordon Bell · Answer

@Bill Keane I currently invest in CT with no experience in Western MA. There are still markets in CT that are affordable that cash flow! I believe you can find a good deal in any market