Grand Danbury

Finding #GrandDanbury

February 5, 2018

It took almost a year of searching to find my house. My brief was Vaguely Specific:

  • Pre-1930s, preferably Victorian, but really just anything old
  • Something that could make money (rentable cottage/apartment, bed and breakfast potential, ability to renovate and resell at a profit – that kind of thing)
  • Some land around it. Maybe an acre, maybe more?
  • Commutable to my work
  • A project. No new build, recently flipped for me – no, I wanted spider webs and original details and the ability to add value with a restoration

So began the search…

The Perfect One that Got Away

I started looking before my house in Sydney had sold, and immediately found the perfect property. It was a short sale, a beautiful Greek Revivial home in need of renovations with 2 accessory cottages and the most perfect dilapidated red barn. The walk-out basement featured a moldy-yet-awesome 70’s bar. There was a lake and a stream and acres of land which was surrounded by vineyards and horse properties. If I had been quicker, and had I had any experience with full renovations at all, it would have been perfect. Hindsight has 20/20 vision though and looking back on it now, although it was everything I wanted, that property would have been far too much work for a novice like me… and likely would have sent me broke. I viewed some other properties on both sides of the Hudson but nothing was quite clicking for me like that one had.


A promotion at work prompted a move from Manhattan to Connecticut, and my search then shifted from Hudson-centric to within-an-hour-or-so-of-Danbury-Connecticut. I hadn’t completely discounted New York state, but Connecticut was proving to be absolutely charming… and the property taxes far more affordable! The move happened quite quickly and I came across my wonderful broker Robert Morey whilst looking for a Connecticut rental. The rental he was representing did not allow pets, but he followed up and was extremely helpful/pleasant… so I gave him my Vaguely Specific Brief.

We drove up and down western Connecticut, scouring the countryside for possible purchases (just imagine the Benny Hill theme song here)
We looked at a 1930s cottage that was charming but I’m certain was haunted.
We looked at a Christmas tree farm just outside of Litchfield (a brilliant interpretation of the ‘must be able to make money’ part of the Vageuly Specific Brief, but the house itself, unfortunately, was a bit of a let down)
We looked at older homes that had fallen into disrepair and were just too much work.
We looked at older homes that had been carefully restored and were not the project I was after.
We looked at many, many basements – and one former hospital (!!) – that could have doubled as sets for horror films.

That man has the patience of a saint.

The Not-So-Old Farmhouse

The first Connecticut property that really piqued my interest was on 3 acres on top of a hill. It was perfectly set up for a small bed and breakfast – large bedrooms, each with a bathroom, and lovely gathering spaces with big fireplaces. To the rear, off the kitchen, was a little apartment that could have served as the innkeepers residence or been rented out on its own. I visited many times, and in my visits I began to realize more and more how much had been altered. The stair was no longer in it’s original location (nor could I determine where it might have been) and now blocked a window. The beams I thought added character were actually added after the fact. I found a dilapidated pool in a pile of unruly bushes – a nice idea in theory, but another expense to remove and replace. I concluded with a heavy heart it just wasn’t the right one for me.

The Overpriced Victorian

The next property that grabbed my attention was a darling Victorian. I had scouted it out before requesting a showing, and as I drove up the hill towards it my heart skipped beat. It was delightful. A turret, fabulous details, standing proudly on a generous corner lot. Now granted, it was about 45mins away and was not in the best town (I heard many locals refer to it as ‘The Armpit of Connecticut’…not a very promising review), but it was on the edge of a State Park and two doors down from a well-visited historic homeย – so it was a possible bed and breakfast. I attended a town hall meeting discussing the reinvigoration of the town’s main street. I daydreamed about how I would renovate the kitchen. I made an offer.

And for months I heard…nothing. The occasional small counteroffer, but no proper negotiations and rarely any contact from the seller’s broker. It was frustrating to say the least. To be fair, I had made a lowball offer – not to be a jerk, but because the house needed extensive renovations/repairs and it really wasn’t in the greatest area. I wanted that house, but I did not want to be the sucker from the city that set the price record for the street. In the end the seller accepted another offer and I walked away, disappointed but relieved to have not overpaid.


After the overpriced Victorian I did some rethinking. It had cemented for me that I wanted a Victorian home, so my Vaguely Specific Brief got slightly more specific and honed in on homes built in the 1800s. My bravado had also worn off and I was looking for a more, ahem, realistic project for my first foray into home renovation. I started the search again.


The One: Grand Danbury

Almost immediately after my rethink I found the listing for Grand Danbury. It was in a great area of town – just two streets over from my rental and minutes from work – but it despite it’s city location it had 1.5 acres of land. It was a multifamily with rental income. It was frigging adorable. We set up an appointment to see it and another nearby home on the same day.

Wouldn’t you know it – both were fantastic. I instructed my broker to make offers on both.

The other property I viewed that day was a sharply priced little home, in need of a rehab but with no major issues. It had just been listed but went so fast we couldn’t even get an offer in on it! It has since had a really quite well done flip and is back on the market for $100k more than it was purchased for last year. Note to self: get faster Danielle!

Grand Danbury had multiple offers on the table – some at full asking price, most with smaller deposits. The sale of my Sydney home afforded me the luxury of being able to give a larger deposit with a lower offer on the price. I expressed to the seller my desire to have a home to cherish and restore. He himself had lovingly restored the exterior and downstairs apartment (with the upstairs apartment being rented to the same tenant for 20+ years) and thankfully chose me as the next custodian of the house.

The upstairs tenants moved out, leaving an unrenovated apartment as my home and project. The downstairs tenants had purchased their own home, but recommended their cousins as new tenants – boom, uninterrupted rental income.


It’s not my forever home, and lacks some of the mystery and magic of a completely unrenovated house, but it is an absolutely perfect way to start my Connecticut real estate adventure.


My Top Tips When Searching for an Older Home

  • Write down what’s most important to you (aka a Vaguely Specific – or even an Actually Specific – Brief) Schools and new kitchens and pools were not important to me. Age, character, and money making potential were. Think about what you need, what’s unimportant, and what you might be willing to compromise on.
  • Find a good broker. I luckily stumbled upon mine, but if I had to start again I would do research and ask for recommendations. Pay attention to how they follow up when you enquire about available properties. Listen to see if they’re giving you spin to get a sale or actually looking out for your best interests (Robert, for example, would NOT let me offer more than I should have on The Overpriced Victorian)
  • Take your time, and be prepared to reassess along the way. After losing out on The Overpriced Victorian, I was able to adjust my focus and find the right property for me. I also rented instead of rushing into a purchase, which took the pressure off the search.
  • Don’t start too early. It’s a good idea to research the market and see what is available at certain price points, but don’t get your heart set on a property before you are prepared to move forward. Have your financing preapproved and deposit ready before really getting into your search.
  • Use what you have to make a strong offer – and I’m not just talking about money. If you can offer a larger deposit, that’s a great way to negotiate on the asking price. But there are also other factors that influence a seller’s decision on which offer to accept – let them know why you want that property, that you’ll cherish it like they did.
  • Get a good inspection. I cannot emphasise this enough. My inspector gave so many great insights into things to keep an eye on, potential problems down the line, how my house was built. Go into your purchase with eyes wide open.

You Might Also Like

No Comments

Leave a Reply