House hacking a duplex in Winsted

9 Replies

Hi all,

I'm currently looking at a duplex to live in over in Winsted. Price seems good. Does anyone have any experience investing or living in that area? There seems to be a lot of single and multi famiy houses for sale. I know it's sort of isolated but was wondering if anybody has any input on the area. 


Hi Dana,

I guess I would like to know peoples opinion on the town. If they invest there, how's the schools, crime, outlook, etc. I've done some research on it and driven through parts of town but I'd love to hear your thoughts on it!


The town of Winsted has some beautiful areas. I personally think of Northwest CT to be one of the prettiest areas in CT and perhaps New England. However, Winsted does not share the school system of region 7 and it does have some negative reputations floating around. The Region 7 high school and middle school located in Winsted doesn't serve that town. Just the neighboring ones. As far as opinions go on the school system of Winchester, I cannot inform you from personal experience. I have found online reviews to sometimes be misleading. It would be wise to consult with some people who actually have kids there. I like the neighboring areas of New Hartford, Harwinton, and Burlington better as far as crime and schools go. There are some areas within those towns to purchase multi family units as well. There are just far less options than Winsted. Demographically, most of Connecticut isn't growing. And one of the problems with the Northwest corner is that it follows suit. 

The Northwest corner is very sheltered as far as values on property go anywhere you want to actually live. I have no issue living in Torrington or Winsted... however many people see it as a stigma. People joke around and call Winsted Wincest. I for one have zero issues investing there or Torrington. You just have to realize what you are getting into. Winsted was a factory town for the most part and you can see the shells of buildings downtown that used to be the factories. 

The prices in places like New Hartford, Canton, Avon, Burlington etc are much higher because they have better schools and probably attract a much higher rent and possibly a better tenant. The only issue nobody wants to talk about in this entire area is heroin. It is here like any other place and nobody wants to talk about it. Shoot me a PM and I am happy to kind of draw out a map of where I would invest and where I wouldn't in the Winsted area. If the price is right I do not think you can go wrong. That being said I house hack in New Hartford and I am losing a tenant of 3 years as he bought his own home. I am going to renovate and probably relist my unit for 1250. If I was single I would rent out my extra bedroom for another 650... unfortunately I am not lol 

Originally posted by @Nicholas Anton :

@Dana Cardwell and @James McCard

I am new to REI and looking to learn more about opportunities in northwest CT. Are you seeing similar things to two years ago when this thread was active? Any differences in recent months?

 I am seeing that the market is very hot right now. Covid is a game changer, I am not sure what the market will do but my tenants are paying rent and that is all that matters. I am still buying but only deals, I do not flip or wholesale, although I might try my hand at wholesaling. The whole thing right now is stuff is so high. 

Earlier this year I purchased a house for 24,000 that was move in ready. I renovated the kitchen and updated the upstairs a bit and now a house one street over is being wholesaled for 93,000. It is a bigger house no doubt and therefore rents for more than mine but I fail to see a lot of value. 

Anything else just shoot me a PM or call or text.