I Love The Houses In Historic Charlottetown, PEI

House And Home, Tales Of Upper Hillsborough, Travel

Welcome to my blog on housing, culture, and design. If you’re new to it – many of my posts focus on Toronto where I make my living as a realtor – but there are many occasions when I cast my net more broadly. Like today, where I’m going to share my love for the homes in Historic Charlottetown, PEI.

I first passed through Charlottetown, Prince Edward Island, in 2005 en route to the celebratory union of my friend Stephanie to her partner Meril at his family’s farm in Meat Cove, Cape Breton. It was one stop of several on a circuitous road trip beginning and ending in Halifax, Nova Scotia, that would see me loop around the east coast for the first time in my life. I’ve commented in the past that we Canucks have a habit of travelling the world and never seeing our own entire country. Even though I’ve been to some pretty remote places, including hiking the mountains in Bhutan and the canyons of Utah in the USA, I’m somewhat embarrassed to admit I have yet to visit the Yukon, Northwest Territories and Nunavut.

Charlottetown was originally on my itinerary in order to see one of my bestie’s James, who has played in the Charlottetown Festival Orchestra since 1999. The festival’s headliner musical – heading into its 56th year – is renown for the irrepressible ‘Anne of Green Gables’ tale based on the bestselling novel first published in 1908 by author Lucy Maud Montgomery. The story, set in 1878, tells the tale of two elderly siblings who share a farmstead and are mistakenly sent an orphan girl instead of a boy farmhand to help with the chores, yet decide to keep her to the dismay of residents until her tenacity and intelligence wins the hearts of the community.

Prince Edward Island is also renown as Canada’s Birthplace of Confederation, for its lush rolling green hills made of red clay ideal for growing potatoes, and for some of the country’s best seafood chowder.

For me, this island is gorgeous for all its elemental glory. No matter what time of year I’m here, I love how colour permeates the natural landscape with a pure palette.

Here’s a few pics from my sojourn here this wintry visit.



Charlottetown is relaxed, engaging, and feels a bit like stepping into yesteryear but with all the modern comforts. And it has some of the best food I’ve ever eaten. There’s enormous inventiveness and food awareness, in part because it’s home to The Culinary Institute Of Canada. But what I especially adore is that everything you need for daily life is within walking distance if your home is in Historic Charlottetown.

Back in June 2012, I posted a blog showing some of the area’s houses at night, in Good Night Charlottetown.

And here are some of my favourites right now:



Charlottetown is chockablock with colourful historic homes in varying degrees of condition, provenance, and character. They’re honest in their construction, many are humble, and some have seen better days. Which isn’t unusual in most downtown Canadian cities, towns and villages. What I like about the dwelling here is they reflect the time, landscape and vernacular of island life, and the domestic architecture of place.


How I Came To Buy A House In Charlottetown, PEI

Three years after that first visit in 2005, I returned to visit James. It was at that time he suggested we co-purchase a property, where it could be both summer accommodations when he’s working here and a getaway throughout the year, with the long-term objective that come retirement we would each have a suite for personal use with the third unit creating an income to offset the operating costs. The idea appealed to me, both because I instantly bonded with Charlottetown’s insouciant charm and because I like subscribing to a long-term plan of aging in place with a best friend. In the interim, we’d rent the three suites to cover the mortgage.

It didn’t take long for us to find ‘the one’. Here’s what we bought ten years ago now – a dilapidated vintage triplex on Upper Hillsborough Street dating from the 1880s, which is an eight-minute stroll to the epicenter of town.

Here’s a pic of the house originally:


And here’s the place now:



Like many buyers of vintage houses who hope to restore their property gently over time, what began as a slow upgrade program unravelled when we discovered an entire 3-storey exterior wall cavity that was part of a 1980s extension had been leaking from top to bottom for quite some time, becoming a breeding ground for mold rendering the place unsafe. It forced us to fast-track our twenty-five-year plan into a systematic retrofit of pretty much every building component (roof, windows, wiring, heating, plumbing), put on a 3-storey tower to create more living space both indoors and out, reconfigure the space plan and install 3 new kitchens and 4 washrooms. It took us eight years to get most of it completed, though when it’s a labour of love one never really is done, is it? You can read the whole journey in my blog called The Tales Of Upper Hillsborough if you share my love for renovation and design, or you can check out the suites in these posts:

This is our airy causal Attic Atelier with its sun-drenched roof terrace which is opposite a massive 100-year-old ash tree home to crows and blue jays.

Here’s Inside The Captain’s Quarters located on the second level, which had the most original features which we’ve carefully restored. It has a magical covered sleeping porch perfect for naps on rainy afternoons.

And this is The Garden Suite on the first floor, which was the level most substantially reconfigured and transformed into the perfect space for hosting family and friends with its well-proportioned indoor/outdoor Entertainment Space.

And if you love landscape design like we do, here’s how we came to have a Black Garden By Dan Does Design.


As time passes, the gift of being able to reside in Charlottetown, Prince Edward Island – if only periodically throughout the year for now – continues to deepen each visit into one of heartfelt gratitude. This is a place where – even for those of us who Come From Away – are embraced by a community of genuine open people and always made welcome. If you ever have the opportunity to visit, I’m quite confident you’ll be both delighted and intrigued.

Wishing you, and yours, a Happy New Year!


~ Steven

Steven Fudge, Sales Representative
& The Innovative Urbaneer Team
Bosley Real Estate Ltd., Brokerage – (416) 322-8000

– we’re here to earn your trust, then your business –

Celebrating Twenty-Five Years As A Top-Producing Toronto Realtor


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