Investment Strategery – Buy in towns called Chester

As you can imagine, I’ve gotten a boatload of questions from family and friends about WHY I bought three houses, all needing renovation, at the same time, all in towns called Chester.

The truth is,

It was an accident.

I mean, the timing anyway. I knew I wanted to purchase real estate as an investment.

I knew I wanted to start in quaint towns. My husband and I have used as a rule of thumb, ‘would I live there’. And for all three properties, the answer is YES.

It started actually with interest in the town of Grafton. We couldn’t negotiate on the house we were interested in – which is good because as much work as the ‘original’ Chester house needs, this other house needed EVERY SQUARE INCH touched. From foundation to rafters. It is an amazing house but legit money pit city!

So we continued to scout the area and found the Green Mountain Tpke house. I have to admit the listing didn’t make it sound as appealing as it really is and when I went to see it I was pleasantly surprised. 

Chester is a great village town, very close to ski locations like Okemo, Bromley, & Magic Mountain. The Grafton Inn which hosts around 40 weddings a year is just 7 miles away, and Chester is just a short drive to the outlet shopping of Manchester. 

This particular property also has a surprising 5+ acres in spite of its village outskirts location. Perfect for, ummm…. 3 horses, a pony, a mule, two goats, 13 chickens and ummm a pet cow. See, we’re sort of thinking maybe one day we’ll move to Vermont when we can figure out how to be there 7 months out of the year and somewhere warm the balance of the time. 

I digress.

So, an insomniac who is looking at real estate does what with her time at 3AM? That’s right! Peruse and Zillow.

Enter house #2. This foreclosure looked by the pictures to be not so bad. We already love the town of Chester VT and see the benefit of investing in the location. Dubbed the ‘healthcare house’ (years from now we hope the monthly rental income will you know, help pay our healthcare expense) this ranch is only about 1/4 mile from the town village. A tenant could literally walk their child to the elements school in town.

And, in spite of being a foreclosure it definitely falls in the category of ‘not so bad’. We’ll fix her up and this is going to be a great spot for anyone to live. And yes, I’d definitely live there! In fact I was at Lowes today designing the new kitchen. It’s going to be great! Not sure there’s room for the entourage of four-legged creatures though….

So I had two properties in the hopper. That’s when the phone rang. It was my realtor in CT, MJ. She said ‘TJ, this is MJ’ (sorry I had to) and then she told me a property had just come on the market in Chester village and it’s a 2 family – a great investment opportunity. Chester CONNECTICUT that is. 

Oi! Don’t I have my hands full already?

So i went to look.

Chester CT is another amazing village town. Wonderful shops and restaurants abound and the Norma Terris Theater is right up the road – and the Goodspeed opera house, Gillette castle and the Connecticut River along with the scenic ferry crossing is all a stones throw away. 

The house can definitely be categorized as the ‘deferred maintenance house’. There’s a lot to be done but the location is awesome- just on the edge of the village, the sidewalk is just across the street as is the historical society. Now if we could just convince the fire department that the siren is not needed in the year 2020. 

The upstairs apartment is adorable and sweet with amazing views. We’ll update the kitchen and bathroom, paint and this will be ready for Airbnb guests. The downstairs will get new closets (IT HAS NOT ONE CLOSET!) a bathroom update, paint and it will be ready for a long term tenant. 

The house itself however will get the asbestos siding removed and a whole lot of odds and ends much needed maintenance and TLC

So there you have it. 3 houses all in Chester all at the same time.

Pray for me. But at least follow along. We’re on the IG @fireflylifeadventures 

Grafton St Chester VT

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