The Annex vs Leaside: Which Is Better for Families?

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

For a family, Leaside is the safer bet and the Annex is the more interesting one. Leaside’s case is a single number: Leaside High School ranks 15th of 742 Ontario secondary schools with a rating of 9.1 on Fraser Institute figures for data year 2023/24, which the TDSB and OPSBA both dispute. The Annex’s case is a walkable house district with four subway stations, Harbord Collegiate Institute (established 1892) and Central Technical School (founded 1915) inside it. The trade is what happens next: more than 3,400 units are proposed within a 300-metre radius of Bayview and Eglinton in a neighbourhood that is mostly two and three storeys today.

Two family bets, made in opposite directions

Families who look at both of these are usually choosing between a school and a lifestyle. Leaside is bought for its schools and its quiet, and has been for two generations. The Annex is bought for the house, the walk and the culture, and the schools are a secondary consideration that families sort out later. Both are defensible. What is not defensible is buying one while imagining the other’s advantages come with it.

Leaside runs Leslie St on the east, Bayview Ave on the west, the rail corridor and the Don valley to the south, extending north of Eglinton Ave E. Bennington Heights is the pocket south and west of the core between Moore Ave and the valley. “South Leaside” is a local trade name, not an official City or TRREB unit. The traditional Annex is Dupont St to Bloor St W, Bathurst St to Avenue Rd.

A C11 AVERAGE IS NOT A LEASIDE PRICETRREB’s C11 district contains Leaside and also Flemingdon Park and Thorncliffe Park, two of the city’s most apartment-heavy, lowest-priced communities. C11’s August 2026 condo apartment average of $442,533 across 15 sales is a Thorncliffe and Flemingdon number, not a Leaside one. If someone quotes you a C11 figure for Leaside, they have quoted you the wrong thing. Use the Leaside community line.

The school question, put plainly

On Fraser Institute figures for data year 2023/24, Leaside High School ranks 15 of 742 with a rating of 9.1, and its five-year rank is also 15 with a rating of 8.8 — so this is not a one-year spike. It opened in 1948. On the elementary side, Bessborough Drive Elementary and Middle School ranks 32 with a rating of 9.9 against a five-year rank of 76, Northlea Elementary and Middle School ranks 447 with 7.8, and Rolph Road Elementary ranks 532 with 7.6. St. Anselm Catholic School, established 1939, is in the area but sits outside the public-school table.

The Annex does not have a comparable headline number in front of me, and I am not going to invent one. What it has are named schools you can walk to: 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, more than 500 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, a composite high school with a dedicated Art Building and a pool. For a kid who is going to specialise in art or in trades, Central Tech is a genuinely unusual asset.

Two things to hold on to. The TDSB and OPSBA both dispute the Fraser methodology and OPSBA has called it a flawed picture, so treat a rank as one input among several. And I cannot tell you which school any particular address attends — that is not publishable from a source I would stand behind. Use the TDSB “Find Your School” tool by address before an offer depends on it.

The short version of the school comparison

Leaside sells you a top-1% Ontario public secondary school and three ranked elementaries in walking distance. The Annex sells you two historic secondaries with specialist programmes and a much shorter walk to the University of Toronto. One is a ranking; the other is a range of options.

What the money says

These are TRREB community figures for Q1 2026 (January to March 2026), the most recent quarter TRREB publishes at community level and therefore about six months old. I have put the sample size beside every average built on a thin count, because at these volumes the average moves with what happened to sell.

Q1 2026, TRREB community	Annex (C02)	Leaside (C11)
Detached average	$2,159K (5 sales)	$2,351K (16 sales)
Detached median	$2,171K	$2,250K
Detached days on market	34	36
Detached sale-to-list	104%	98%
Semi-detached average	$1,671K (9 sales)	$1,269K (4 sales)
Semi days on market / SP-LP	20 days, 99%	16 days, 101%
Condo apartment average	$1,192K (48 sales)	$697K (6 sales)
Condo days on market / SP-LP	42 days, 96%	28 days, 96%
Condo apartment new listings	207	not published
Detached sales-to-new-listings	—	53%

The detached numbers are closer than most people expect: a $2,159K Annex average on five sales against $2,351K in Leaside on sixteen. What separates them is what the money buys. In Leaside you are buying a house on a quiet residential grid in a neighbourhood that is 55.5% single-detached and 72.4% owner-occupied on 2021 Census figures, with a median household income of $148,000 in 2020. In the Annex you are buying a large late-Victorian or Edwardian house, often already carved into flats, on a street that carries students and through traffic.

One Leaside income figure is worth pausing on: average household income was $284,400 against a median of $148,000 — the average is 1.9 times the median, the widest gap in midtown. That is a small very-high-income cohort sitting on a solid professional middle. It explains why the top of the Leaside market can look detached from the rest of it.

What roughly $1.3M actually buys in each

This is where the abstraction breaks down. In Leaside, $1.3M lands you in the semi-detached market — four sold in Q1 2026 at an average of $1,269K and a median of $1,343K, in 16 days at 101% of list. That is a small sample, so treat the average loosely, but the shape is right: a semi on a residential street, in a neighbourhood that is two-thirds pre-1960 stock, with Leaside High School’s catchment somewhere nearby to confirm.

In the Annex the same money is a condo apartment or nothing. The nine semi-detached sales that quarter averaged $1,671K with a median of $1,430K, so $1.3M is under the semi market rather than in it. What $1.3M does buy comfortably is a unit: 48 condo apartments sold at an average of $1,192K and a median of $818K, with 207 new listings behind them, so there is choice and there is room to negotiate. It is a very different life from a Leaside semi — and, if you have two children, a much harder one.

Getting around: four stations against two that opened this year

The Annex has four subway stations — Spadina, St George and Dupont on Line 1; Bathurst, Spadina and St George on Line 2 — with St George and Spadina both being Line 1/Line 2 interchanges, plus the 511 Bathurst and 510 Spadina streetcars and the 26 Dupont bus. No GO station. And no expressway, because the neighbourhood stopped the Spadina Expressway that would have divided it in half.

Leaside had no rapid transit at all until Line 5 Eglinton opened on 8 February 2026, and gained two underground stations in a single day. Leaside station sits at Bayview and Eglinton with two entrances, connecting to the 11 Bayview, 34 Eglinton and 334 Blue Night. Laird station at Laird Dr and Eglinton is the easternmost underground station on the line’s main tunnel, connecting to the 34 Eglinton, 51A/51B Leslie, 88 South Leaside and 334. There is no Line 1 or Line 2 station in Leaside: you transfer to Line 1 at Eglinton and to Line 2 at Kennedy. No GO station either. The DVP is reached via Millwood Rd and Overlea Blvd to the south, or Eglinton Ave E and Leslie St to the east.

THE LRT DID NOT FLOAT PRICESIn the six months after Line 5 opened, C11’s MLS HPI single-family detached benchmark fell 6.93% year over year and attached fell 8.43% — steeper than the City of Toronto’s own detached figure of −4.33% in August 2026. Anyone telling you the Crosstown will lift Leaside values is currently being contradicted by TRREB’s own index. It may still prove true over a decade. It is not true yet.

What is being built, and why Leaside buyers argue about it

This is the defining local fight of the next five years. More than 3,400 residential units are proposed within a 300-metre radius of Bayview and Eglinton, now a Major Transit Station Area, in a neighbourhood whose tallest existing form is largely two to three storeys. Named applications include 1718 Bayview “Leaside Common” (Gairloch/Harlo), 197 units at 9 storeys and already under construction; 1802 Bayview at 419 units and 46 storeys; 589 Eglinton E at 442 units and 35 storeys; 1779 Bayview at 373 units and 35 storeys; 1840 Bayview at 377 and 34; 2 Glazebrook at 434 and 34; 586 Eglinton E at 249 and 32; 1837 Bayview at 288 and 25; 545 Eglinton E at 300 and 25; 660 Eglinton E, Sunnybrook Plaza (RioCan/Concert) at 412 units in 16 and 12 storeys; and 503 Eglinton E at 174 units and 13 storeys.

Laird in Focus is the City’s planning study for the Laird Dr and Eglinton Ave E area. Note that three other Focus Areas advanced to Site and Area Specific Policies while Laird “required additional study and public consultation” — so nobody should be quoting you permitted heights on Laird Dr, including me.

The Annex’s equivalent is finishing rather than starting. Mirvish Village on the Honest Ed’s site delivers roughly 900 purpose-built rental units across seven buildings of 8 to 27 storeys, 200,000 sq ft of commercial space and direct access to Bathurst station, with The Kitchen as a 19,000 sq ft food hall and 25 micro-retail pods in Honest Ed’s Alley. Peterson Group took full control from Westbank in early 2026; the remaining buildings were due late summer or early September 2026. Ten restored heritage houses line Markham Street.

The construction trade

In Leaside you are buying before the change and will live through it. In the Annex you are buying after a decade of it at Bloor and Bathurst, as that corner finally finishes. If a quiet decade matters more to you than a top-15 school, that alone may settle it.

The honest downsides of each

Leaside: the benchmark is falling faster than the city. C11’s August 2026 HPI showed detached at $2,227,300 down 6.93%, attached $1,348,400 down 8.43% and townhouse $547,800 down 8.49%, against a city composite of −3.73%. Fast schools do not make a rising market.
Leaside: the skyline is going to change around you. Over 3,400 units are proposed at one intersection and the Laird study is unresolved. If you buy on Bayview expecting the view and the traffic to stay as they are, you are buying a version of Leaside that is ending.
Leaside: no subway of its own and no GO. Line 5 is a transfer line here. Everything downtown is a change of trains, and the DVP is a drive through Millwood or Leslie to reach.
The Annex: crime is well above the city average. In 2025 break-and-enter ran at 387.1 per 100,000 against 189.5 city-wide, with assault at 1,080.9 against 767.9 and auto theft at 116.9. For a family that is the number I would want on the table early.
The Annex: transience and conversions. Heavy student and rental demand means rooming-house conversions, absentee landlords and upkeep that varies house by house. The stock is 1886 to the 1910s and carries all the burdens that implies.
The Annex: no highway, and a thin freehold market. Five detached sales and nine semi sales in a quarter is not much to choose from, at a detached median of $2,171K. If you need to move quickly and specifically, you may wait.

So which one, and for whom

Choose Leaside if the school run is the organising fact of your next ten years, if you want a detached house on a quiet grid with a 72.4% owner-occupied neighbourhood around you, if Leaside Memorial Community Gardens and Trace Manes Park are the shape of your weekends, and if you can accept both a falling benchmark and a skyline argument at Bayview and Eglinton. Buy away from the Bayview and Eglinton radius if the construction matters to you, and read the Laird in Focus material before you fall in love with anything near Laird Dr.

Choose the Annex if you want your children to grow up walking to school, to Koerner Hall and to the Royal Ontario Museum along the Bloor Street Culture Corridor, if a house from the 1880s with original detail is worth more to you than a ranking, if you or your partner work at the University of Toronto, and if you have the tolerance and the budget for an old, heavily converted house on a busy neighbourhood grid. Do not choose it expecting a suburban school-district experience: that is Leaside’s product, not the Annex’s.

If you want a straight read on what your current place is worth before you commit to either, start with a home valuation and work backwards from what you can actually carry.

Common questions

Is Leaside High School really one of the best in Ontario?

On Fraser Institute figures for data year 2023/24 it ranks 15 of 742 secondary schools with a rating of 9.1, and its five-year rank is also 15 at 8.8, so the result is consistent rather than a one-year spike. The school opened in 1948. The TDSB and OPSBA both dispute the Fraser methodology, and OPSBA has called it a flawed picture, so treat it as one input.

Did the Eglinton Crosstown raise Leaside house prices?

Not so far. Line 5 opened on 8 February 2026 and Leaside gained two underground stations, Leaside and Laird. In the six months that followed, C11’s MLS HPI detached benchmark fell 6.93% year over year and attached fell 8.43%, steeper than the city-wide composite decline of 3.73%. Any claim the LRT has lifted values is contradicted by TRREB’s own index.

Can you buy a detached house in the Annex for Leaside money?

Roughly, yes, though both are expensive and thin. In Q1 2026 the Annex recorded five detached sales averaging $2,159,000 with a median of $2,171,000, while Leaside recorded sixteen averaging $2,351,000 with a median of $2,250,000. The difference is what you get: a converted Victorian on a busy grid versus a house on a quiet residential street.

How many units are proposed at Bayview and Eglinton?

More than 3,400 residential units within a 300-metre radius, in an area now designated a Major Transit Station Area. Named applications range from 1718 Bayview at 197 units and 9 storeys, already under construction, up to 1802 Bayview at 419 units and 46 storeys. The Laird in Focus study is unresolved, so no one should quote permitted heights for Laird Drive.

Does Leaside have a subway station?

Not on Line 1 or Line 2. Leaside has two Line 5 Eglinton stations, Leaside at Bayview and Eglinton and Laird at Laird Drive and Eglinton, both underground and both open since 8 February 2026. You transfer to Line 1 at Eglinton station and to Line 2 at Kennedy. There is no GO station in Leaside.

What are the real drawbacks of raising a family in the Annex?

Three worth weighing. Break-and-enter ran at 387.1 per 100,000 in 2025 against 189.5 city-wide. The housing stock dates from 1886 to the 1910s and is heavily converted to flats and rooming houses, so upkeep varies block to block. And there is no expressway access at all, which shapes every trip out of the city.

Leaside schools or an Annex house?

Tell me your children’s ages and your real budget and I will tell you which of these two actually fits, including the case for buying neither. If it is Leaside, I will show you which streets sit outside the Bayview and Eglinton construction radius.

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 Leaside: Two Very Different Bets for Families