Buying in The Annex vs Willowdale: Houses or Towers?

Published 10 September 2026 · By Jatin Dua, Broker of Record, RE/MAX Quantum Realty

Last updated 10 September 2026. Written by Jatin Dua, Broker of Record at RE/MAX Quantum Realty, 799 The Queensway, Etobicoke · Toronto neighbourhood comparison · 9 min read

Quick answer

These two are barely the same product. The Annex follows Simeon Janes’s 1886 subdivision, was annexed to Toronto in 1887, and its houses date from 1886 to the 1910s — the type’s original is 37 Madison Avenue, built for Lewis Lukes and finished in 1887. The Willowdale condo core at Yonge and Sheppard is a 1990s and 2000s creation: the City’s #151 Yonge-Doris counts 9,090 apartment units in buildings of five storeys or more and twenty single-detached houses in the whole neighbourhood. Willowdale is far cheaper per unit and far further out — Sheppard-Yonge to Union is 14 stops on Line 1, Finch is 16. The Annex costs more and puts you four stations from everywhere.

One neighbourhood was drawn in 1886, the other built in the 1990s

I have taken buyers north from Bloor and south from Sheppard on the same weekend, and the two conversations have almost nothing in common. In the Annex the questions are about knob-and-tube, third-floor flats and whether the front porch is original. In Willowdale they are about which building, which exposure, which floor and what the maintenance picture looks like. Neither buyer is wrong. They are shopping in different centuries.

The traditional Annex runs Dupont St on the north, Bloor St W on the south, Bathurst St on the west and Avenue Rd on the east. Willowdale runs Bathurst St to Bayview Ave and Finch Ave down to Highway 401 at the southeast, and grew out of three postal villages — Newtonbrook, Willowdale and Lansing — named for the willow trees on the Gibson property.

The codes, and the traps hiding in both names

The Annex trap is size. The City’s #95 Annex retained its legacy number through the 2022 restructure, but it extends east across Avenue Rd to Yonge and swallows Yorkville, with a Toronto Police Service projected 2025 population of 38,487. TRREB’s Annex community in C02 is a different shape again. Crime and census claims almost always use the City’s larger boundary; price claims use TRREB’s.

Willowdale’s trap is that it is at least five things. Yonge St is the dividing spine: east of Yonge is C14, west is C07. C14 covers Willowdale East and Newtonbrook East; C07 covers Willowdale West, Lansing-Westgate, Newtonbrook West and Westminster-Branson. On the City map, legacy #51 Willowdale East was split in April 2022 into #151 Yonge-Doris, #152 East Willowdale and #153 Avondale, while #37 Willowdale West was not split at all.

“WILLOWDALE” CAN MEAN A TOWER OR A 52.9% DETACHED SUBURB#151 Yonge-Doris is 92.3% apartments of five storeys or more with twenty detached houses in it. #152 East Willowdale, immediately beside it, is 52.9% single-detached with 69.8% owner-occupancy and a 2020 median household income of $95,000. Same name, opposite neighbourhoods. Ask which unit any statistic you are shown belongs to.

The money

TRREB community figures below are Q1 2026 (January to March 2026), the most recent quarter published at community level and therefore roughly six months old. District figures are August 2026. Sample sizes are beside each thin average.

Q1 2026, TRREB community	Annex (C02)	Willowdale East (C14)	Willowdale West (C07)
Detached average	$2,159K (5 sales)	$1,998K (24 sales)	$1,975K (13 sales)
Detached median	$2,171K	$1,684K	$2,170K
Detached days on market	34	34	32
Detached sale-to-list	104%	94%	98%
Semi-detached average	$1,671K (9 sales)	not published	not published
Condo apartment average	$1,192K (48 sales)	$625K (78 sales)	$598K (30 sales)
Condo apartment median	$818K	$595K	$580K
Condo days on market / SP-LP	42 days, 96%	40 days, 98%	42 days, 96%
Condo new listings	207	321	not published
Condo sales-to-new-listings	23%	24%	—

Two things jump out. First, detached prices are not that far apart — a $2,159K Annex average on five sales against $1,998K in Willowdale East on twenty-four — but the sale-to-list ratios go opposite ways: 104% in the Annex, 94% in Willowdale East. Annex houses go over ask; Willowdale East detached houses do not. Second, the condo gap is enormous: a $818K Annex median against $595K in Willowdale East, with 321 new listings behind 78 sales.

At district level in August 2026, C14 recorded 72 sales, 380 active listings and 5.7 months of inventory against 4.6 city-wide, at 96% of list in 38 days. C07 recorded 59 sales, 317 active and 5.8 months, at 94% in 38 days. Both are slower than the city. If you are buying, that is leverage.

The short version of that table

The Annex is a scarce freehold market with a soft condo segment attached to it. Willowdale is a deep, oversupplied condo market with a detached market that is also negotiating. In one, houses go over ask; in the other, almost nothing does.

Two housing stocks, a century apart

The Annex’s stock is large late-Victorian and Edwardian detached and semi-detached houses, very heavily converted into multiplexes, rooming houses and student rentals, plus low-rise apartment blocks along Bloor and Spadina and a small number of condo buildings. “Annex style” is a genuine named architectural type — a Toronto synthesis of American Richardsonian Romanesque and British Queen Anne Revival, with big rounded Romanesque arches and Queen Anne detail such as turrets. The type’s template is E.J. Lennox’s Lewis Lukes residence at 37 Madison Avenue, finished in 1887 by the architect of Old City Hall and Casa Loma.

Willowdale’s is the opposite kind of record. In #151 Yonge-Doris, 2,845 households live in stock built 1991 to 2000 and another 2,840 in stock built 2001 to 2005, with only 105 households in anything pre-1960. #153 Avondale is 77.8% apartments of five storeys or more. #37 Willowdale West is 63.0% apartments and 26.0% detached; #38 Lansing-Westgate is 50.1% apartments and 36.3% detached with a 2020 median income of $98,000. Across the low-rise side, so-called monster homes have been replacing 1910s to 1950s single-family stock since the 1990s — East Willowdale’s construction is spread evenly across every decade since 1960, which is the signature of continuous lot-by-lot replacement.

Willowdale is also the most international neighbourhood in this comparison: roughly 70% immigrants, with the largest groups Chinese at 22%, Korean at 9.35% and Iranian at 8.77%, and home languages running English 31.4%, Chinese 12.3%, Persian 11.1% and Korean 8.9%. The Yonge St strip from Sheppard to Finch is the densest Korean, Chinese and Persian retail in the city. That is a genuine reason to choose it that has nothing to do with price.

Getting around: four stations and no highway against sixteen stops and the 401

The Annex is served by Spadina, St George and Dupont on Line 1 and Bathurst, Spadina and St George on Line 2, with St George and Spadina both interchanges, plus the 511 Bathurst and 510 Spadina streetcars and the 26 Dupont bus. No GO station. No expressway either — the neighbourhood stopped the Spadina Expressway that would have cut it in half, and it has lived with the consequences ever since.

Willowdale has Finch (the northern terminus), North York Centre, Sheppard-Yonge and York Mills on Line 1, plus Line 4 Sheppard running east from Sheppard-Yonge to Don Mills. Surface service at Sheppard-Yonge includes the 84 Sheppard West family, the 984A express, 98C Willowdale-Senlac, 185 Sheppard Central, 97A/97B Yonge and the 320, 384 and 385 Blue Night routes. There is no GO station on Yonge in Willowdale. Highway 401 forms the southeast boundary with interchanges at Yonge and at Avenue Rd/Bathurst, and the 404 and DVP are to the east.

The number that decides it for a lot of downtown workers: Sheppard-Yonge to Union is 14 stops on Line 1 and Finch to Union is 16. That is the longest transit run of any neighbourhood I write about. The Annex is four stations, two of them interchanges, and everything downtown is a short ride. In exchange, Willowdale gives you a highway on your doorstep and the Annex gives you none.

The Yonge North Subway Extension is under construction — 6.3 km north from Finch with five stations at Steeles, Clark Avenue, Royal Orchard Boulevard, Bridge and High Tech. A $1.4B tunnelling contract went to North End Connectors in August 2025, a stations, rails and systems package worth roughly $4B went out for qualifications in October 2025, and preliminary works began at Finch station in February 2023. There is no confirmed opening date, and I would not price one in.

Schools: the widest spread in the comparison

Willowdale’s Fraser Institute figures, data year 2023/24, run from excellent to poor within a short walk. Secondary: Earl Haig Secondary School rank 23 of 742, rating 8.9; A Y Jackson SS also rank 23 at 8.9; William Lyon Mackenzie CI rank 33 at 8.7; Georges Vanier SS rank 275 at 6.7; Newtonbrook Secondary School rank 401, rating 5.9, improving sharply from a five-year rank of 539; and Cardinal Carter Academy for the Arts, a TCDSB school, at rank 8 with a rating of 9.3. Elementary: Avondale Alternative at rank 1 with a rating of 10.0, and Avondale PS at rank 702 with 7.3. Hollywood, McKee, Cummer Valley, Yorkview, Churchill and Finch are not ranked, which is not a low rating.

The spread between Earl Haig at 23rd and Newtonbrook at 401st is the point. In Willowdale the catchment line is worth six figures, and it is the one variable I would nail down before anything else. I cannot tell you which address attends which school — no source I trust publishes that reliably — so use the TDSB “Find Your School” tool by address, and do it before you write an offer, not after.

The Annex’s schools are named rather than ranked here: Huron Street Junior Public School, 541 Huron St, JK to 6, roughly 270 students with an on-site daycare; Jesse Ketchum Junior and Senior Public School, 61 Davenport Rd, JK to 8, 500-plus students; Harbord Collegiate Institute, 286 Harbord St, established 1892, over 900 students with French Immersion and a Math and Science Focus programme; and Central Technical School, 725 Bathurst St, founded 1915, with a dedicated Art Building and a pool. And a standing caveat: the TDSB and OPSBA both dispute the Fraser methodology.

Where each one will disappoint you

Willowdale: the steepest apartment decline in the north. C14’s August 2026 apartment benchmark was $558,700, down 10.12% year over year, against a city apartment figure of −6.88%. In the same district townhouses fell 0.53% and detached 2.02%. If you are buying a unit, you are buying into the worst-performing segment in midtown and north Toronto.
Willowdale: oversupply you can count. Willowdale East recorded 321 new condo listings against 78 sales in Q1 2026, a 24% sales-to-new-listings ratio, with C14 sitting at 5.7 months of inventory and C07 at 5.8 against 4.6 city-wide.
Willowdale: the planning rules are unsettled. The Secondary Plan dates to 1997 and governs an area now holding over 50,000 residents and 35,000 employees. Council adopted the North York at the Centre Directions Report with amendments on 25 to 26 March 2026 and staff report back in Q1 2027. Anyone buying near Yonge on the expectation of a specific height permission is buying ahead of the rules.
The Annex: crime well above the city. In 2025 the neighbourhood recorded 387.1 break-and-enters per 100,000 against a city figure of 189.5, with assault at 1,080.9 and auto theft at 116.9.
The Annex: an expensive, thin freehold market. Five detached and nine semi sales in a quarter, at a detached median of $2,171K and a semi median of $1,430K. Very little choice, and no negotiating room when something good appears.
The Annex: conversions and old bones. Heavy student and transient demand means rooming-house conversions, absentee landlords and inconsistent upkeep, on stock built between 1886 and the 1910s with everything that implies for wiring, plumbing and insulation.

If you are buying a unit

Willowdale is cheaper and deeper, but its apartment benchmark fell 10.12% year over year to August 2026 while the city fell 6.88%. Cheap and still falling is a real combination. Buy it for the neighbourhood and the space, not as a bet on the next twelve months.

Who each one is actually for

Choose Willowdale if you want more square footage for your money, if Mel Lastman Square, the Toronto Centre for the Arts, the North York Central Library and Empress Walk are the amenities you will actually use, if the Yonge retail strip and its Korean, Chinese and Persian food are part of why you are moving, and if a longer commute is a fair trade for a bigger place. Choose it especially if you are buying for a family and can land inside the Earl Haig or A Y Jackson catchment — confirm that by address rather than by listing copy.

Choose the Annex if you want a house rather than a unit, if you want to be four stations from everything and never need a car, if the Bloor Street Culture Corridor with its 24 partner organisations and the University of Toronto St George campus are your daily life, and if you can carry a freehold at these levels. It is a worse deal on space and a better one on the hours you spend commuting.

If you are a first-time buyer weighing the two, the honest answer is usually Willowdale on affordability and the Annex on lifestyle — and the first-time buyer guide is a better place to start than either listing feed.

Common questions

How many detached houses are there in the Yonge-Doris condo core?

Twenty, on 2021 Census figures for City neighbourhood #151 Yonge-Doris. The same neighbourhood counts 9,090 apartment units in buildings of five storeys or more, 92.3% of its 9,845 households, with only 105 households in stock built before 1960. It is a purpose-built 1990s and 2000s condo district rather than a converted older neighbourhood.

Why did Willowdale condo values fall more than the rest of the city?

C14’s MLS HPI apartment benchmark was $558,700 in August 2026, down 10.12% year over year against the City of Toronto apartment figure of −6.88%. It is the steepest single-segment decline among midtown and north districts. Supply is the visible cause: Willowdale East saw 321 new condo listings against 78 sales in Q1 2026, and C14 carried 5.7 months of inventory.

How many subway stops is it from Willowdale to Union?

Sheppard-Yonge to Union is 14 stops on Line 1 and Finch to Union is 16. Willowdale also has North York Centre and York Mills on Line 1 and Line 4 Sheppard running east to Don Mills. There is no GO station on Yonge in Willowdale, so the subway is the through route downtown.

Which Willowdale high school ranks highest?

On Fraser Institute figures for data year 2023/24, Cardinal Carter Academy for the Arts, a TCDSB school, ranks 8 of 742 with a rating of 9.3, and Earl Haig Secondary School and A Y Jackson SS both rank 23 with 8.9. Newtonbrook Secondary sits at 401 with 5.9, though improving sharply. The TDSB and OPSBA dispute the methodology, and catchments must be confirmed by address.

Is the Annex a realistic option for a first-time buyer?

For a house, rarely. In Q1 2026 the Annex’s five detached sales carried a $2,171,000 median and nine semi sales a $1,430,000 median. For a unit it is possible but pricey: 48 condo apartment sales averaged $1,192,000 with a median of $818,000, at 96% of list in 42 days. Willowdale’s condo median of $595,000 is a far easier entry point.

Is the Yonge North Subway Extension worth waiting for?

Not as a purchase decision. The 6.3 km extension north from Finch with five stations at Steeles, Clark, Royal Orchard, Bridge and High Tech is under construction, with a $1.4B tunnelling contract awarded in August 2025 and preliminary works at Finch from February 2023. There is no confirmed opening date, so pricing one in is speculation.

Annex house or Willowdale tower?

Give me your budget and how often you actually need to be downtown, and I will tell you which of these two your money works harder in. If it is Willowdale, I will tell you which side of Yonge and which catchment before you look at a single unit.

Book a 15-minute call or call or text 833-330-1925.

No pressure, no drip campaign. If the answer is “neither, wait six months”, I will tell you that.

The Annex vs Willowdale: 1887 Houses or a 1990s Condo Core