Gaudy Or Grand: Behind The Doors Of Multi-Million Dollar Mansions In Bridle Path & St Andrews-Windfields (Plus Lessons On The Lifecycles Of Neighbourhoods & Houses)

Real Estate


Welcome to the Urbaneer blog on housing, culture, and design! I’m Steve Fudge and I’m celebrating my 31st year as a realtor and property consultant in Toronto, Ontario, Canada.

First, if you just crave some eye candy on how Toronto’s elite live in status markers valued from $4,425,000 to $15,200,000 in Toronto’s tony Bridle Point & St. Andrews Windfields just scroll on down to see the insane sales team member Nadia brought to our attention. But if you’re curious about how our housing and the neighbourhoods in which they’re contained have their own lifecycles, stay the course and learn some interesting and fun facts about Toronto real estate!

Thanks Nadia for finding these! And, dear reader, thank you for checking out our post!

I’ve written a lot about how Toronto – the City of Neighbourhoods – has been undergoing a massive change since the 1990s, evolving from a gritty industrial port city into a glittering global post-modern metropolis. I’ve explored the dynamics of gentrification and densification, how a booming technology economy has fuelled demand, and how existing archaic residential zoning policies contribute to a lack of affordable ownership options while ensuring property owners in established centrally-located neighbourhoods will reap huge financial rewards when they sell in the years to come.




The Lifecycle Of Housing

Consumer products we buy at an electronics store, such as an iPhone for example are designed for obsolescence. Similarly, dwellings and even the neighbourhoods in which they’re located have what is commonly referred to as a “lifecycle”. In fact, the lifecycle of a dwelling is predetermined just like the intentionally planned obsolescence of your Apple iPhone, except it doesn’t occur as quickly (Surprise Fact: The average life span of an Apple Device is four years and three months).

In Canada, the life cycle of the typical wood-framed ‘stick-built’ dwelling sitting on a concrete foundation and covered in vinyl siding, plastic trim, and faux stone located in a mass-produced planned suburban community newly built today isn’t intended to last much longer than 50 years. The reason is mostly economic. Once you add up all the soft and hard development costs associated with getting the land secured and serviced; the planning approvals, permits, and development charges required; the fees to design the facades, space plans & interior finishes as well as the structural, engineering and major building component systems drawn and detailed;  the costs allocated to physically create the shelter using qualified construction labour using mid-grade materials; the budgets being spent on financing, legal, sales & marketing over the 3 to 7 years it can take to complete development, plus the developer’s profit, the cost to purchase is either the top end of budget or the most consumers are willing to pay.

I’m not overtly political but it’s also important to note that for all the cheers and chatter about the City of Toronto and the Ontario government’s commitment to building more economical housing (Fordnation, please don’t sacrifice the Greenbelt), “developers in Toronto pay an average of $86 per square foot in government fees, compared to $70 in Vancouver and $24 in Montreal”; the development charges for a dwelling this year range from $52,367 for a studio or one-bedroom apartment to $137,040 for a semi-detached or detached house which “account for between 10.4 to 23.5 percent of the cost of construction in Toronto” according to this CBC article “Developers, Housing Advocate Criticize Development Fee Increase Amid Housing Crisis“.

Because the costs to deliver shelter to our current building code standards are at the top end of affordability, building to extend the lifespan of these residences  – like installing a metal roof, high-performance windows, composite decking, superinsulation, sustainable materials, and green building practices – are ultimately left to the homeowner to initiate and complete. And while I believe we need to take a hard look at what we build in the context of our Climate Crisis & Risk Assessment, I don’t want to argue that it’s necessary to build for a longer period of time, because what’s fashionable in housing is always evolving (as you’ll soon see), and our collective need for shelter is ever-changing. For example, I can’t imagine Torontonians in the 1960s ever envisioned the two-storey commercial / residential buildings or big box stores that line Danforth Avenue from Greenwood to Victoria Park would be slated for several thousand mid-rise and high-density dwellings in the 2020s – some as tall as 55 storeys – to meet Toronto’s housing crisis. After all, Crescent Town at Victoria Park & Danforth Avenue wasn’t even completed until 1971. If you’re interested in learning how this main street arterial road is being transformed, here’s my post that explains Why I Believe More Condominiums On The Danforth Is Good.



Above Is An 1880s Bay & Gable Victorian In West Queen West We Sold In 48 Hours!


Although you might be quick to point out that a fair bit of Toronto’s Victorian and Edwardian solid brick housing in the central core still stands 100 to 150 years after its construction, these residences were predominantly constructed using hand-crafted materials that were made to a higher spec than the machine-manufactured products made today. In particular – and unique to Toronto – the Bay & Gable Victorian Architecture that was coveted by the merchant class in the 1880s through 1900s is celebrated for its architectural flourishes including solid brick detailing, gingerbread fretwork, slate roofs, and bejeweled stained glass windows. If you’re interested in seeing some of T0ronto’s exemplary architecture, consider Strolling The Tree-Lined Streets Of Historic Cabbagetown which contains North America’s largest collection of preserved Victorian residences.

I would be remiss if I didn’t mention that these often historically-designated dwellings were also built for the well-heeled rather than the working class, though there were many poor sister copies built by the aspiring but less affluent. If you didn’t have pots of money you could purchase a pared-down version. For example, instead of the entire dwelling having double-brick construction the front facade might have a brick veneer while the side and rear elevations were covered in wood plank and tar paper, the hand-carved spindle gingerbread fretwork might be replaced with frieze boards, and the elaborate faceted glass jewel and bevel pieces in the stained glass windows of the merchant class would have simpler patterns and less embellishment. Alternatively, if that was still too rich for you, you could buy a row house or an Ontario Gothic Revival Cottage.

It’s not much different today. Every model home – whether a freehold or a condominium property – offers a basic version with the option to pay a further premium to select an upgrade package on fixtures and finishes that reflect the latest trends in domesticity. Otherwise, there’s a lot of consistency to what is constructed today. The foundations and structures are built to last around 50 years, while the materials and major building components (heating/cooling, windows, wiring, plumbing, and roofing) are made with a planned obsolescence of 25 years or less. And to extend their lifespan, the owners are obliged to do ongoing maintenance and repair if they want to protect their investment and ensure the occupants stay dry. Want a crash course in this? My post on Understanding The Six Essential Layers Of Housing breaks it all down in an easy peasey read and this post On The History – And Popularity – Of The Open Concept Space Plan shares how renovators in the 1970s began resolving Buyer resistance to the warren of rooms typical of our original Victorian and Edwardian housing stock.




The Lifecycle Of Neighbourhoods

Did you know how and when our neighbourhoods developed has been shaped by the arrival and popularity of different modes of transportation, including the bicycle, the horse & buggy, the railway, the streetcar, and the rise and dominance of the automobile which still exists to this day? It’s also been shaped by the evolution and practice of urban planning. In my piece about Urban Planning And Toronto Real Estate I examine how The Garden City Movement of the 1900s contributed to the design of our post-war suburbs in Canada.

As a result, just as our dwellings have lifecycles, so do our neighbourhoods, which ebb and flow through four stages: growth, stability, decline, and renewal. Sometimes these four phases can occur in a relatively brief period of time, but it usually takes decades.

During the growth period, the location is coveted, growing in demand and popularity. The growth period is when rents rise, real estate values increase and the area is considered highly desirable and a status marker. A few years ago I wrote How Toronto Real Estate Near Queen Street – East & West – Is Climbing In Value, which explores how former working-class neighbourhoods to the east and west of the central core have seen their property values explode due to the proximity and ease of access to a direct streetcar line to the financial district.

The stability phase is when a neighbourhood is in equilibrium and consistent in its high rate of owner occupancy, stability, and pride of ownership. By those criteria, many of our city neighbourhoods would be considered stable. However, a 2017 Ryerson University report found the majority of Toronto’s 140 residential neighbourhoods have had a stagnant or declining population for the past 30 years, because households are having fewer children and residents are choosing to age-in-place rather than sell their homes. This translates into a reduction in the use of amenities (like schools, libraries, and recreational facilities) that are coveted by families, diminishes community engagement and vitality (fewer residents supporting local retailers, fewer kids playing road hockey) while restricting the filtering of housing stock necessary to maintain a balanced real estate market. Furthermore, although these residential neighbourhoods are well-established, much of its vintage housing stock – ranging in age from 60 to 180 years – is reaching a lifespan where it is becoming structurally or operationally compromised. Fortunately, along with the existing as-of-right approvals for laneway housing and garden suites, the Province is looking to override municipal zoning laws and implement as-of-right approvals for up to 3 units per property in an effort to fast track the creation of much-needed housing.

A neighbourhood’s period of decline comes when properties show signs of deferred maintenance and repair, there is a decrease in owner-occupied dwellings with conversion into multi-units, and the resident profile switches. Toronto’s Parkdale neighbourhood is undergoing a rebirth right now as existing residents fight gentrification – which is ironic given this neighbourhood was originally developed for Toronto’s wealthy elite – but it fell in decline with the building of the Gardiner Expressway in 1955-56. With Toronto’s growth and the popularity of the automobile taking precedence over the preservation of the urban fabric, around 170 residences and the Sunnyside Amusement Park were demolished, leaving the balance of this affluent neighbourhood cut off from its direct access to the sandy beaches of Lake Ontario. Deeply scarred, the wealthy exited leaving many grand houses to become rooming houses, whole streets were blockbusted for the creation of rental housing, and in its decline came rebirth, including emerging ‘Little Tibet’. Here’s more about this in my post called Eclectic, Elegant and Cool: The Housing Stock of Parkdale

Renewal – which is often associated with gentrification – is when a location starts to attract a new resident profile. It often begins with artists, non-conformists, and liberated progressives moving to a location because it’s economical and their own presence spurns reinvention and rejuvenation. These early adopters attract buyers who begin to invest in upgrading the housing stock which snowballs into it becoming hotly commodified. Want to learn more? Here’s my post called Gentrification, Densification, And The History Of Toronto Real Estate shares my own undergraduate research on this topic.

No story illustrates it better than a piece I wrote back in 2015 called A $15 Million Mansion In Toronto’s Tony Forest Hill that I posted on my student mentorship site called Canadian Real Estate. Housing & Home. It shares the history of Forest Hill, a prestigious Toronto neighbourhood developed in the 1930s for wealthy Jews, and the sale of a $4,000,000 residence in 2010 that was purchased as a ‘tear down’, from which its ashes emerged a new mansion five years later that subsequently listed for $15,000,000 and sold for $13,000,000. In many ways, the impact of this sale was significant, both for the once high-status movers and shakers of the Jewish community suddenly finding themselves demoted to occupying the ‘tear downs next door’ and for the impact it had on property values throughout the central core. Imagine throwing a stone into a pond and watching the water ripple from where it lands. The sale of that $13,000,000 mansion had the same effect, such that long-standing working-class neighborhoods like Oakwood Village to the west saw property values skyrocket. In 2015, the average sale price of a dwelling was $684,090, with the most expensive sale clocking in at $1,399,000. Just 7 years later Oakwood Village had Ten New Builds Sell For Up To $3,025,000!




From Rich, To Richer In Bridle Path and St Andrews-Windfields!

Just like Forest Hill, I’m fascinated by the extent other affluent neighbourhoods are gentrifying. At one time gentrification was defined by the movement of middle-class households into working-class neighbourhoods, but today it refers to people with a higher status and greater affluence than the existing ones taking residence. And to illustrate this, we looked at the recent sales in two exclusive pockets.  The first originally catered to the jaunty equestrian set who settled in the Bridle Path and the second being in the master-planned communities marketed by E.P. Taylor to the upper-middle class – like Bayview York Mills and the St Andrews-Windfields area – recognized as one of Toronto’s Millionaires’ neighbourhoods.

We were astonished, in part because if a neighbourhood doesn’t stipulate any urban design guidelines, which is common in Toronto, decades later what was once a collection of dwellings in a similar aesthetic evolves into an eclectic pastiche of architectural styles that Disneyfies the pomp and circumstance of status. Sometimes it’s well-executed and sometimes it’s McMansion Hell!

So here’s a taste with 7 sales we thought we’d share with you, with the photos and information taken from the Multiple Listings Service.






Property One – 7 York Road – Built in 1989

Listed $4,488,80   •  Sold: $4,425,000

From MLS: *An Opportunity To Make This Quality-Built (4828 Sq Ft Plus Lower Level) Home On A Fabulous 65′ X 145′ Lot, With A South-Facing Backyard, Your Own!*Custom-Built, Well-Maintained & Thoughtfully Designed With Features That Stand The Test Of Time* Main Floor Boasts: 10 Ft Ceilings / Elegant Entertaining Space / A Home Office / A Spacious Kitchen & Family Room / Convenient Side Door Entry & Laundry* The Upper-Level Features: 9 Ft Ceilings / A Primary Retreat With: Sitting Room, Fireplace, 2 Walk-In Closets & 7-Piece Ensuite* The Lower-Level Offers Storage & Recreation Space, And Direct Access To The Rare 4-Car Garage*Update/Decorate To Make It Yours On This Lovely, Quiet Street In The Heart Of This Sought-After Neighbourhood*

Note the surprising use of the colour black




Property Two – 2 Royal Oak Drive – Built in 1968

Listed: $4,688,000  •  Sold: $4,380,000 (Aug 2022)

From MLS: Situated In The Prestigious Neighbourhood Of The Coveted Iconic The Bridle Path. This Corner Lot Beckons You To Either Build Your Dream Home Or Work With The Existing Builders Own 1968 Family Home. The Possibilities Are Endless On This 130 X 135 Foot Lot. Dare To Dream And Reimagine This Wonderful Property Located In One Of Canada’s Premier Enclaves, Minutes To Granite Club, Elite Private Schools, Superb Public Schools, Edwards Gardens +++Endless Opportunities To Create Your Dream Home – Build New Or Work With The Existing. Perfect Corner For A Modernist Design Or Classic Beauty, Or Renovate And Add On. *No square footage provided.*

This 5.5M Toronto Home Is a Stellar 60s Time Capsule – BlogTO

We thought the rounded wooden trim accents on the cabinetry are so out, they’re back in! How mod!






Property Three – 32 Suncrest Drive – Built in 1969

This dwelling wasn’t newly constructed. Instead, the owner secured permits to substantially renovate it using portions of the original dwelling (often just a piece of the foundation to circumvent the high permit fees for new construction. See the photo above as it looked when it sold in 1997 for $723,000 before it was transformed.

Listed: $6,590,000  •  Sold: $6,328,000 (Feb 2022)

From MLS: Bright & Elegant Fully Renovated Home In Exclusive Bridle Path With Over 8,000 Sq. Ft. Of Living Space + Basement. Impressive Design Highlighting Modern Finishes & Amenities. Grand Foyer W/ Soaring Ceils & Architectural Skylight. Entertain In Sprawling W/O Bsmt W/ Wet Bar. Backyard Oasis W/ Huge Stone Patio & Ample Greenery. Walk To Edwards Garden, Wilket Creek & Sunnybrook Parks. Near Renowned Schools In Quiet Neighbourhood.

Now that’s a crazy two-storey entry!




Property Four – 38 York Road – Built In 2018

Listed: $7,995,000  •  Sold: $7,495,000 (April 2022)

From MLS: Architecturally Significant 9,200′ Of Liv. Area On Premium Corner Locale. Georgio Lolos Arch. One Yr New. Car Afficiando’s Lift W/Glass 8 Car Show Rm. State Of The Art. W/Finest Luxe Appts. O/Concept Kit/Fam W/O To Stn.Loggia W/Wood Fp. Cascading Nat Light. Soaring Ceils.Feels Like 6 Star Hotel Fin. Mn Floor Lib. Mudrm. Chef Kit W/Pntry, Servry & 7Pc Appl, Marble Island, Bfast Area & Bar. Master W/10Pc Mrbl Ens,Boudoir,Fp & Terr. L/L Wine Cel,Wet Bar & Nanny Rm

We call this Modern Baronial!




Property Five – 12 Baytree Crescent – Built In 1995 & Backing onto St Andrews Park

Listed: $10,888,000  •  Sold: $8,750,000 (February 2022)

From MLS: *Truly A Rare Opp-Hm Of Imagination & Inspiration**Majestically Set On A Magical Ravine In Highly Coveted Neghd(Apx 1 Ac)*Distinguished-Unique Estate(Apx 15000 Sf Living Area-6Bedrms/12Washrms-Entertainer Paradise)-Unique Designed/Ececuted W/Remarable Craftsmanship-This Is A Hm 4 All Seasons W/Impeccable Details-Luxurious Details:Zen-Like Waterfall Cmbd Ravine View-Indr Pl W/Retractable Rf-Fun Sty Rec Rm,Leather Flr(Lib),Guest/Nanny Quarter-More!*

This property is featured in a 2021 BlogTO article: The 10 Most Expensive Homes For Sale In Toronto Right Now

Post-Modern Space Galore!




Property Six – 21 Old Colony Road – Built In 1992

Listed: $11,980,000  •  Sold: $9,420,000 (January 2022)

From MLS: *Magnificent Masterpiece ! One Of A Kind! Located In One Of The Most Prestigious Neighborhood. Pure Sophistication And Luxury! Unprecedented Quality. This Exclusive Residence Was Custom Built By Award Winner Builder Adam Smuszkowicz For Its Current Owners With Unsurpassed Craftsmanship And An Easy Flowing Floor Plan Ideal For Comfortable Family Living And Entertaining. A Wealth Of Windows And Skylights Provide Ample Natural Light For This Spacious And Charming Home. This Refined Residence Contains Too Many Wonderful Features To Mention In This Description. Over 16,000 Sq. Ft. Of Living Space.*

Here’s a 2021 Storeys article about the property: This North York Estate is More Like a High-End Art Gallery Than a House

This is full-on Glamansion!



Before In 2007:

After: New Build In 2014:


30 Fifeshire Road – Built in 2014 – Otherwise known as the Schitt’s Creek mansion

Listed: $17,888,000  •  Sold: $15,200,000 (October 2022)

From MLS: *La Belle Maison-Luxurious, Custom Build Residence In The Heart Of Prestigious Neighborhood Of St Andrew Winfield’s. This 24000 Sq. Feet Residence Combines Old Artisanship With Very Latest Of 21 Century State Of The Art Luxurious Amenities ,Foyer, Marble Stairs ,Breathtaking Balustrades And Ceiling Motifs Will Transfer The Visitors To The 19 Century France . Features A Unique Architecturally Crafted Carved Limestone Exterior * Home Theatre W/ 10 Comfortable Seats Equipped W/ Modern Sound System, Audio, Video & Gaming (Lutron Home System), Features On The Big Screen, Amazingly Crafted Wine Cellar, Billiard Room.*

Storey’s Article: Toronto’s “Schitt’s Creek” Mansion Back on the Market for the 10th Time



Are You Looking For A Property To Purchase?

While our client roster includes some rich and famous, we serve first and second-time buyers, relocations, renovators, and those building their long-term property portfolios. Our mandate is to help our clients choose the property that will realize the highest future return on their investment while ensuring the property best serves their practical needs and their dream of “Home” during their tenure. At Urbaneer, we identify a property’s best qualities, features, and insouciant charm in the context of your wishes and wants, plus your future target market. Although searching for the right property can be an intense and sometimes lengthy process it is, without fail, rewarding both to our clients and the Urbaneer team. We are so grateful to be the realtor of choice for both established Torontonians, and the newly arrived.


If you enjoyed this post, here are some other blogs you might like:

Housing As A Symbol Of Self
Understanding The Development Process: Part One – and – Part Two
Hello Toronto, Ontario, Canada! Make Your Home A Net Zero Hero!
On Building Sustainable Housing In Canada
Exploring COVID-19, Urban Planning And Toronto Real Estate
Exploring Toronto Real Estate Property Values
The Psychology Of Real Estate, Housing & Home
Dear Urbaneer: Does Canada Have A History Of Building Affordable Economical Housing?
Dear Urbaneer: What Do I Do With My Dated Bungalow? (Plus A Brief History On This Housing Type)


Are you dwell hunting for a house or a condo? Consider letting Urbaneer guide you through your purchase process. At, we’re here to help – all without pressure or hassle. We simply love what we do! With a multi-disciplinary education in housing, sound knowledge of the mechanics of real estate, and a sharp skill set in evaluating properties for over three decades, my team and I are here to guide you through all the factors which play into Toronto’s real estate market.

Sincerely & With Thanks,

~ 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 Thirty-One  Years As A Top-Producing Toronto Realtor


*Like what you’ve read? Did you know we were recently listed as one of  The Top 25 Toronto Real Estate Agents To Follow On Twitter, The Top 50 Blogs On Toronto, and the Top 100 Real Estate Blogs In Canada!!? Consider signing up in the box below to receive our FREE monthly e-newsletter on housing, culture, and design including our love for unique urban homes and other Toronto real estate!

*Love Canadian Housing? Check out Steve’s University Student Mentorship site called Canadian Real Estate, Housing and Home which focuses on architecture, landscape, design, products, and real estate in Canada.


Previous Post
Toronto Real Estate Sale Prices Dropped In February 2023
Next Post
A Climate Risk Assessment Tool Is Now Available For Canadian Homebuyers & Homeowners