Welcome to our latest Tales Of Upper Hillsborough post, which shares the journey of two friends, who share a friendship spanning 30 years and who both live in Toronto, Ontario. These friends buy a dilapidated vintage triplex in idyllic Charlottetown, Prince Edward Island, and transform it into a bespoke vacation guest house.

Right now James and I are pretty much squealing with joy, as we’re nearing completion of the last and middle of three furnished suites – which we affectionately call The Captain’s Quarters – six years since our original purchase in 2008. What was supposed to be a slow-simmer upgrade programme spanning the next twenty years – when we theoretically reach ‘retirement’ age – this $600,000 foundation-to-eaves rebuild unraveled (partly by accident but mostly on purpose) when we realized that this endearing ‘Home Away From Home’ desperately needed a comprehensive, thoughtful, transformation and rebirth.

This charming dwell was constructed in the 1880s – and in desperate need of some TLC. Once we reconciled that the right thing to do was restore, rejuvenate and well, ELEVATE this character wood-shingle manse into a revenue-producing Guest House for vacationing travelers, business consultants, and – most importantly – ourselves, we realized the opportunity to be proud owners of a domestically-satisfying profit-generating adventure. It’s also because we realized we LOVE spending time here, visiting regularly beyond the summer months when James takes up residence to play in the Charlottetown Festival, as he has done for the past 18 years. Plus James discovered this photo in the archives and, while it might sound strange to many, we intuitively feel those kids in the vintage photo walking up the street to the house – shown in elevation – are cosmically connected to who we are today.

The first suite we tackled was our two-bedroom Attic Atelier, which is easy breezy comfortable. Then we did a massive rebuild – including a three storey tower addition to ensure we had three bedrooms in The Garden Suite, which is now “pinch me perfect”. Lastly, we embarked on renovating the second floor, which we call The Captain’s Quarters. We instantly adored the vintage patina of this suite and, while there weren’t many original details intact, we made the commitment to restore and replicate as much of the character as possible. This included elevating the suite with modern conveniences while referencing the residence’s 1880s history.

Because we’ve been executing this transformation remotely from Toronto, which is a 2 hour 15 minute flight west of Charlottetown – we’ve had a bit of trial and error furnishing the suites. The main reason is the rooms in this character dwelling appear much larger in our heads than they do in person, so we often come up with elaborate decorating schemes or choose massive pieces which – we’ve had occasion to discover – swallow the space.

And nowhere has it been tested more than in tackling the Entertainment Space of this suite.

Being one of the former second floor bedrooms of the original house has, during its life span, seen a bedroom become a bathroom in the 1930s, another bedroom become a kitchen circa 1970s, and an addition added on the rear in the 1980s. When we bought the house, this two-bedroom suite was the only suite retaining original details like high baseboards, interior panel doors and bull-nosed carved trim.

Since our purchase, The Captain’s Quarters got some outdoor space, when we added a covered ‘sleeping porch’ off the rear bedroom as part of a three storey ‘deck tower’ addition and a balcony on the roof of the new side porch off this suite’s kitchen. The suite – like the entire house – has new windows and French doors, foam insulation, reconditioned radiators, new wiring, and upgraded plumbing. We refinished the original wood floors, installed new custom runners and crown molding in the centre hall after restoring the original staircase and banister. The front porch was rebuilt, and the front hall on street level was returned to its formal glory (albeit without access to the main level) including a custom marble mosaic ‘carpet’ and some nifty pendant lighting made out of mason jars. We dropped a bomb of big bucks into renovating the washroom with period style fixtures so that it feels old in a classic ‘vintage style’, with stacking laundry discreetly installed. And then we went crazy with a dreamy custom kitchen, including designing a china cabinet with antique leaded glass windows and recessed lighting to reference a bygone era.

And through all of it, the Sitting Room of this suite drove us bonkers, as it’s totally bijou.

As in 10 x 12 feet bijou.

More importantly, it had a lot of functions to fulfill. This room must include a pull out couch to accommodate two more guests – or their kids – if required. It also needed to fit a dining table that can accommodate a group, the requisite flat screen Apple TV necessary for any luxury furnished rental, and fit the 1960s record player we bought on Kijiji.ca for $150 including the family’s record collection. Here’s the floor plan, with the room in the bottom right corner

Here are some Before Pics when it was tenanted:

To make this space work, we went straight for our first-hand solution which was to build a custom dining banquette. A banquette is a great space saving way to create seating-for-many-in-a-squeeze – plus kids love the intimacy and novelty of bench seating which doesn’t seem to be around as much as it once did. We like how the bench can be additional storage for seasonal items – or in this case the record collection – and how it always pairs well with a round table. We also love a round table, as there’s no issue of a table leg blocking the ease of gathering extra chairs round.

Originally we ordered a round table which was too large, but we managed to cancel the order before it was processed when I had enough common sense to double check the measurements against ‘The Great Room’ living in our imagination. This reality hit hard when the Sleeper Loveseat from Sears – which was our only local option without incurring a great ‘shipping expense’ – arrived and appeared to swallow the room. I was aghast when the horrible truth dawned on me that this was not the romantic cloistered ‘room of my dreams library’ with built-in shelving showcasing vintage finds of island life, a reading/dining table replete with chess board, and an elegant comfortable chintzy sitting area with just a hint of grandma.

Nope. This room was a modest plain jane bedroom with no space for fantasy. It hit hard when the massive down-filled leather chair we splurged on from Restoration Hardware some years back – the one that had failed to fit in every room throughout the house thus far – didn’t fit here either. Nor would the contemporary soupcon of a light cube from Stylegarage. That they found their home in the Centre Hall – the last place we had considered – was a surprising delight – and relief.

Here’s how that worked out.

Don’t you love?

Truth be told, my imagination fools me every time. Having renovated small spaces in the past, I should know better by now. But it’s also part of the fun. Your fantasy has to translate into reality – which forces you to edit your design into something more clever, creative, and intelligent. Scale, proportion and precision rein supreme, leaving minimal room for error. Even at this stage, we’re still refining – I can see what I’d like to change already – but finishing a place is an evolution so even these “Reveal Photos” are images in progress.

One tip I happily pass on is my commitment to ensuring cocktail tables are always small and movable. This allows people to configure the space as they need – and creates opportunity for more room. After all, with an old record player you can be sure this room is home to some spontaneous dance parties. I originally thought the carpet should be a solid neutral similar to the walls to help keep the space unadorned and airy. But when we stumbled on this graphic carpet in the flooring store, we knew it gave us the ‘pop’ this unadorned space needed.

Here’s how the space looks right now… we’ve got some tweaking to do!

Unlike the other two suites which are more open concept, this bijou room challenged us to keep the colour a calming neutral while layering it with texture.  .

We LOVE The Captain’s Quarters!

Of course, being able to choose to stay in any of our three suites makes it impossible to choose a favourite. They’re all awesome!

Here’s our Black House website if you’re curious to learn more.

And stay tuned for more reveal of our Captain’s Quarters in The Tales Of Upper Hillsborough!

~ Steven and the urbaneer team

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Tales Of Upper Hillsborough