Best areas to invest in Connecticut?

15 Replies

Hey! I'm a beginner investor looking to buy my first multifamily property in the next few months and start earning some cashflow. In your opinion, what are the best areas to start investing in in CT? I live in Stonington, so I'm not too familiar with the west part of the state. Any help is appreciated.


@Abbie Gibson

Hello Abbie, in our neck of the woods, the best areas for cashflow are New London, Norwich and Groton. That being said, you can find a property that cashflows well in other towns in New London County, but it is definitely tougher now with all the competition for on market deals.

You can search for your own off market deals or you could get on some wholesaler lists. Ronald Jude Dutes is a wholesaler in the area. I'll send you a PM with contact information. 

Hi @Abbie Gibson , here are my thoughts on the greater Hartford (Hartford county, really) rental market in the event that you come up this far. As a licensed real estate agent myself, I can get into trouble for "steering" you to an area, so please accept these as just some generally vague thoughts based on my experience of the area and property management industry.

Windsor is a great "small town" that generates good cashflow with moderate chances of appreciation (relative to the CT Market)

Granby even a smaller town feel than Windsor, rentals are in high demand and rent prices are high. Expect high prices too, though. Appreciation likely.

Enfield is better on cashflow, but has some rough parts of town that I personally avoid (Specifically T'ville). It does have a busy shopping area, and a mall that desperately needs attention. The proximity to MA is a benefit.

Manchester strong rents, but getting into the market can be tough, as multis are priced accordingly.

West Hartford if you're in this town you're probably banking on appreciation, not cashflow.

Glastonbury Strong rents, but expensive. Multis / rentals are not common, and in demand. Appreciation likely.

East Hartford Mostly a B/C class community. I like it. Rents are strong, proximity to downtown Hartford is a major plus. Prices have gone up steadily since 2015/2016.

New Britain
Still has quite a negative stigma, mostly due to crime. I hear it all the time when I'm showing tenants units in other towns and I get asked "Do you have any other units available." You can see the expressions if you say "Yes we have one in New Britain." We manage in town, but I don't feel comfortable enough to purchase in NB myself. That being said, prices can be attractive.

Bristol Strong rental market. Seems to always have demand given proximity to Hartford, Waterbury and Meriden.

Filipe Pereira that's a great summary of towns in the GH area! After renting in West Hartford for a couple years it's tough to accept its not ideal if the goal is cashflow. 

I'm also on the hunt for my first investment property and have been focusing my search on primarily off market properties. Has anyone had experience with the BRRRR strategy?


I sold a single family rental up in the Northwest corner of CT that I had owned since 2005. I highly recommend staying clear of purchasing multi-families in towns such as Torrington, Winsted, or Winchester. Yes, these places are the gateway to New Englands Berkshires but do not believe any hype. No matter where you are looking to invest in CT really take the time to do your market research on the town or city. Do a full return on investment evaluation as well. This site has all the tools to help complete those tasks. Be mindful of rumored grants towns or cities are trying to secure for community revitalization programs. Track jobs markets and school district scores they will tell you which communities are healthy and growing. Towns/cities can have unsecured grants dry up in a heartbeat and then you could be stuck with a property in a way off the beaten path community like I was. Again do the research.

Hope this snapshot example and thoughts help your quest.


Welcome and congratulations on your real estate journey, @Abbie Gibson !

The first steps I would recommend as a new investor is to get a handle on analyzing the income, expenses and ROI of these properties in Bridgeport.

You can use the Bigger Pockets calculators to start. Use Zillow and to get data and analyze a few from your home to see what type if returns there are.

If these meet your investment criteria then start looking in person.

Let me know if you have any questions.

- Craig

Welcome aboard to multi-family investing @Abbie Gibson .   I hope your investing journey starts off on a great note.  Prior to the virus pandemic, Connecticut had several monthly meetup groups where investors would get together and network with each other.  This included Fairfield Cty, New Haven, and Hartford.   A lot of those meetings slowed down since the pandemic, but New Haven continues to have monthly meetings at the beginning of every month.  

Go to the events page on BP and search for upcoming events near your zip code.

BTW: I like @Filipe Pereira breakdown of the Hartford County rental market.  Wish there was a similar breakdown for Fairfield and New Haven counties.   I may need to draft something and get input for fellow investors & PMs in the area so we can post it here.   

@Abbie Gibson a lot of good advice all around. I think every town has certain elements and deals that can work. It is definitely not a buyers market as houses are selling for more than asking ( at least I can speak for Fairfield County) due to the high demand from New Yorkers moving to CT. With that said, I have investment properties in Bridgeport and Stratford. Of those markets interest you, reach out and I can give you my 2 cents. Best of luck.