10 Precedent-Setting Sales In Toronto’s Oakwood Village Neighbourhood This Past Year

Midtown, Real Estate

Welcome to my blog on housing, culture, and design in Toronto! This is where I share my insights and experiences on almost every aspect of the Toronto Real Estate Market – and life here in the 6ix!

During the Covid19 pandemic, I spent a lot of time researching and writing about the ways the pandemic was reshaping our lives, both in terms of our domestic spaces (How To Resolve Your Work From Home Dilemma + Demand For ‘Forever Homes’ In Toronto’s Downtown Family Neighbourhoods Persists), how we spent our leisure time (The Movement To Hipsteading) and how the search criteria of buyers shifted to prioritizing square footage (The New Space Race), more private outdoor space, and fueled an exodus from urban centres as I wrote in Going East: A Toronto Real Estate Exodus To Atlantic Canada.

Although my attention for the past 2+ years has been on the newly emerging shelter trends wrought by Covid19 (including Post-Pandemic Housing Trends To Watch For), as we move out of our collective pandemic survival mode to one where we’re repeating the mantra “the worst is over, the worst is over, the worst is over”, I can confirm the evolving market conditions I’ve been observing in the real estate trenches remain omniscient. Namely, neighbourhoods in the original City of Toronto are undergoing a massive rejuvenation – initially through the renovation of the existing housing stock during the first 15 of my 30 years as a realtor but, more commonly since is the acquisition of properties that are torn down and then substantially rebuilt or are newly constructed into luxury executive residences.

In Exploring Toronto Real Estate – which I posted nearly 6 years ago – I explain the three approaches to establishing value, which is a Market Value Comparison approach, an Income approach and a Land Value + Development = Cost approach. All three are legitimate ways one might determine the value of a property. In that blog, I also cite several houses which had been recently sold, and which were effectively ‘tear downs’ and valued for their lots.

Since that blog – despite the temporary impact of the Provincial Government’s ‘Fair Housing Plan’ intervention back in 2017 – our robust market continues at a time when our original housing stock is increasingly obsolete and no longer serving the needs of most modern households. And it spans the entire original City, which I illustrated back in 2018 with a post called Ten Toronto New Builds That Recently Sold For Between $2M And $10M. It exemplifies there is a massive amount of redevelopment in Toronto, where small-scale builders to large real estate corporations are paying top dollar to acquire sites and invest substantial sums to transform a property into its current highest and best use. In almost all cases this also means creating shelter for the most affluent, leaving a rapidly diminishing supply of (somewhat) habitable housing for the rest of us, as I wrote in The Affordability Conundrum For Toronto House Buyers: Location, Condition & Costs.

Today, there is no neighbourhood that is not being redeveloped. For example, four years ago in How Toronto Real Estate Near Queen Street – East & West – Is Climbing In Value I shared some recent sales of substantially transformed residences flanking either side of the Financial District to demonstrate how once marginal locations are now setting new price precedents in the downtown core. These sales signal that once upon a time you could get a pretty significant discount for a depreciated property that was in proximity to urban blight (like industrial sites and sewage treatment plants), but this is no longer the case.

This kind of change is occurring in many neighbourhoods across the original City Of Toronto – like Oakwood Village which is the focus of today’s post. Our urban fabric is changing. And, as we’re witnessing, the more a location sees newly rebuilt and renovated swish houses come to market (over $2mil+ price range), the more it reassures other Builders and Buyers to follow suit.

This blog details 10 new or substantially rebuilt houses to sell in the Oakwood Village Neighbourhood over the past year. Where is Oakwood Village? This multi-cultural family-friendly neighbourhood – represented by Portuguese, Italian, Spanish, Jamaican and Filipino immigrants – has the geographic boundaries of St Clair Avenue West on its south end and Eglinton Avenue West on the north, and Arlington & Winnet Avenues on the east side, with Dufferin Street/Westmount Avenue on the west.



There are two aesthetics in domesticity that are dominating our urban neighbourhoods: the growing modern contemporary cube or the more traditional classic contemporary pastiche. They represent what’s on-trend right now. Observationally, Oakwood Village tends to have more modern infills being built than neo-traditional dwellings. I’m not entirely certain as to why, but when you see the exterior facades you’ll know what I mean by this.

I should note that some of these houses are entirely new construction while many retained some – albeit minor – parts of the original dwelling. This is in part because getting a permit to renovate an existing dwelling (even if you keep one foundation wall of the original house) is faster and less costly than securing a permit for a new home (which is often significantly more expensive, too). This bureaucracy may explain some of the time differences from acquisition to resale, though many other factors likely also played a part in the duration of each project.



House One

A detached 2-storey dwelling with a private drive on a 38′ x117′ lot sold in May 2019 for $1,177,000.



It was then severed into two 19 foot wide parcels and 27B Lanark – a 3-storey 3000 square foot 5+1bed, 4.5bath semi – sold two years later in May 2021 for $2,025,000!



House Two

A detached 2bed bungalow constructed in 1925 having a mutual drive on a 21.5′ x 105.5′ lot sold in January 2017 for $615,000.



It was then transformed into a detached 3 storey 4+1bed, 4.5bath dwelling. Five years later, in January 2022, it sold for $2,255,000!



House 3

A detached 1.5-storey 3bed, 1.5bath residence built in 1945 having a private drive on a 25′ x 120′ lot last sold in July 2014 for $460,000.



Retaining the yellow brick first-floor facade with rounded bay window brickwork, it was reimagined as a 2.5-storey 4+2bed, 3.5bath detached residence with a private drive, artfully balancing the dwelling’s Arts and Crafts roots with contemporary materials. In June of 2021, it sold for $2,125,000.



House Four

A detached 2bed, 1bath bungalow with a private drive on a 27′ x 100′ lot sold in December 1996 for $153,000.



Torn down, the bungalow was replaced with a detached 2storey 3bed 4.5bath contemporary cube with built-in garage that sold in November 2021 for $2,120,000!



House Five

A detached 2-storey 4+1bed, 2bath house dating from 1918 with a private drive on a 26′ x 105′ lot sold in October 2016 for $800,500.



In 2018 it was substantially transformed into a 2200 square foot (above grade) 3-storey 4+1bed, 3.5bath dwelling that sold for $1,450,000. I resold most recently in September 2021 for $2,125,000!



House Six

Originally constructed just after 1910, this detached 2bed 1bath bungalow with a mutual drive on a 21′ x 140′ lot was sold in November 2013 for $360,000.



In 2016 the dwelling was replaced by a modern, detached 3-storey 3bed, 2.5bath lofty swell dwell selling in March 2016 for $1,250,000. It was more recently sold in February 2022 for $2,040,018!



House Seven

Originally this property was a 2bed, 2bath bungalow built in the 1940s with a mutual drive on a 25.75′ x 110′ lot that sold in November 2013 for $528,000.



In 2015 it was reimagined into a detached 2storey 3bed 3.5bath classic contemporary residence with no on-site parking, selling in December 2015 for $1,110,000. It was resold for $2,201,000 in August 2021.



House Eight

Here’s a 2bed, 1bath bungalow originally built in 1942. It was situated on a small 33′ x 61′ lot, and it sold in May 2017 for $807,000.



It was then substantially renovated – including an addition – to become a 2-storey 3bed, 2.5bath, contemporary residence with carport, selling in April 2022 for $2,325,000.



House Nine

Below is a detached 2-storey 4bed, 3bath house constructed in 1920 with a mutual drive on a 25′ x 121′ lot that previously sold under a power of sale in July 1993 for $195,000.



Substantially renovated in 2021, this 3-storey legal duplex with a detached 2-car garage and a mutual drive offered a flexible design to accommodate one to three units, including three kitchens and three independent heating / cooling systems. It sold in January 2022 for $2,327000.



House Ten

Finally, this was a 2bed, 2bath bungalow dating from the 1940s with a private drive on a premium 30′ x 140.8′ lot. It last sold in March 2017 for $1,250,000.



In its place, a detached 2-storey custom-built smart home of around 4000 square feet was constructed having 3+1beds 4.5baths, a single car garage and a comprehensive landscaping package. It sold in May 2021 for $3,025,000 – setting a new price precedent for the Oakwood neighbourhood.



Toronto’s freehold housing stock – which is typically 70 to 170 years old – is neither energy-efficient, nor environmentally sustainable, nor does most of it cater to the demographics or lifestyles of today’s urban households. Setting aside the issue of ‘affordability’ – which is the political hot potatoes du jour with excellent reasons – in our free-market economy it’s not unreasonable for the shelter industry to pursue property for profit, especially when there are consumers with hunger and appetite to purchase one as their primary residence.

The shift in land use and valuation has had enormous repercussions for those seeking freehold housing at lower price points, as those options are quickly evaporating. Even locations once considered marginal are ripe for redevelopment. And I am not immune to the reality that this has consequences for the natural filtering of housing stock, as we need buyers and sellers moving up and down all price points and housing types to keep a market healthy and, more broadly, rental housing spanning all levels of affordability to keep city living healthy, diverse and inclusive.



If you’re looking for an opportunity to create a custom home like any of the ones above, we can help you find the property to do it! Here’s a 2bed bungalow we just sold on Clovelly Avenue that we call An Opportunity To Transform A Vintage Bungalow Steps To The New Oakwood Station





Further reading. If you enjoyed this, you might like these other Urbaneer posts:

Since I started the blog 11 years ago, along with writing about buying and selling property, design, culture and urban life, healthy (and unhealthy) housing, and my real estate forecasts, I’ve explored a number of different facets that shape our housing market including:

2013 –> Why Toronto’s East Side Real Estate Has Historically Been Cheaper

2015 –> What Are The Real Financial, Emotional And Health Costs Of Commuting?

2016 –> Buying A Toronto Condominium Pre-Construction With A 2020 Update –> More On Buying A Toronto Condo Preconstruction

2017 –> On Building Sustainable Housing In Canada & In 2020 –> Hello Toronto, Ontario, Canada! Make Your Home A ‘Net Zero’ Hero

2017 –> The History Of The Ontario Gothic Revival CottageBay & Gable Victorian Architecture In TorontoEdwardian Residential Architecture In Toronto

2017 –> In 2010 I Predicted Why Toronto Real Estate Prices Would Skyrocketed Over The Next Decade

2018 –> The Psychology Of Real Estate, Housing & Home

2018 –> Gentrification, Densification, And The History Of Toronto Real, Estate

2018 –> Why Toronto Real Estate Near Queen Street – East & West – Is Climbing In Value

2018 –> Ten Toronto New Builds That Recently Sold For Between $2M And $10M

2018 –> About Laneway Housing In Toronto, By Sustainable And Urbaneer

2018 –> Foreign Buyers, Property Prices, And Toronto Real Estate – and – Foreign Buyers, Inadequate Policy, And Canadian Real Estate

2019 –> Toronto Real Estate, Yellowbelt Zoning & The Missing Middle: Part One & Part Two

2019 –> How Toronto Real Estate Is Shifting From ‘Fixer-Upper’ Flips To ‘Tear Down’ New Construction

2020 –> Trending In Toronto: Single Family Houses Replaced By Boutique Condo Townhomes

2020 –> Demand For ‘Forever Homes’ In Toronto’s Downtown Family Neighbourhoods Persists Despite COVID-19

2020 –> Exploring COVID-19, Urban Planning And Toronto Real Estate

2021 –> Toronto’s Booming Technology Economy And Our Real Estate Market

2021 –> The Growing Trend Of Financial Landlords In Toronto Real Estate

2021 –> On Garden Suites In Toronto, By The Architect Builders Collaborative, Sustainable, & Urbaneer

2021 –> Multi-Generational Living Is Trending In Toronto

2021 –> Shades Of Duplicity In The Foreign Buyer Tax For Canadian Housing

2022 –> When Dreams Of Domesticity Became Nightmares: A Recollection Of The 1989 Toronto Housing Market Crash



Thanks for reading!

– Steve & The Urbaneer Team


Now more than ever, it is essential to plan a well-researched, data-driven, tactical strategy if you are in the market for a new home. Especially in changing times, when the pandemic has prompted many to shift their focus and objectives. Have yours changed? Please know The Urbaneer team is here to help!

May we be of assistance to you, or someone you love?



The Urbaneer Team

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 –


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