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Four Winds Condos, 21-37 Four Winds Dr: Big 1970s Suites Near York U

Published 20 October 2026 · By Jatin Dua, Broker of Record, RE/MAX Quantum Realty

Building at a glance · York University Heights

Four Winds Condos in one look.

21-37 Four Winds Dr, Toronto

Built

1972

Storeys

11

Suites

3360

Developer

Cadillac Fairview Corporation

Corporation

TSCC-1749

Walk Score

88

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What is your unit at Four Winds Condos worth today?

Floor, exposure, parking and this building’s own recent sales move the number. Your estimate appears instantly, and a written CMA from me is one tap after.

  • Uses this building’s own recent sales
  • Adjusts for floor, view and parking
  • Your number appears instantly

How you get around

Scores from Walk Score®

Walk Score

Very Walkable

Transit Score

Excellent Transit

Bike Score

Very Bikeable

Transit, nearest first

  • 41KeeleTTC bus0.2 km
  • 106SentinelTTC bus0.2 km
  • 101Downsview ParkTTC bus0.6 km
  • 1Finch West stationLine 1 Yonge–University0.6 km
  • GODownsview Park GOBarrie line2.0 km

Distances are straight-line from the building.

How far is everything?

From the front door, in kilometres.

Big Daddy's Halal GrillSteps

Finch West station0.6 km

C W Jefferys Collegiate Institute0.6 km

Derrydown Public School0.7 km

FreshCo1.7 km

Downsview Park GO2.0 km

Schools for this address

Public schools from the TDSB school locator, checked 18 October 2026. Boundaries change: confirm with the board before you buy.

ElementaryJK–5

Derrydown Public School

120 Derrydown Rd, North York

0.7 km · ~11 min walk

Zoned for this address

MiddleGr 6–8

Elia Middle School

215 Sentinel Rd, North York

1.1 km · ~17 min walk

Zoned for this address

High schoolGr 9–12

C W Jefferys Collegiate Institute

340 Sentinel Rd, North York

0.6 km · ~9 min walk

Zoned for this address

Catholic elementary

St Wilfrid Catholic Elementary School

0.5 km · ~8 min walk

Nearest, confirm zoning

Catholic elementary

St Charles Garnier Catholic Elementary School

1.6 km · ~25 min walk

Nearest, confirm zoning

Catholic secondary

James Cardinal McGuigan Catholic High School

0.4 km · ~6 min walk

Nearest, confirm zoning

French-language · Viamonde (public)

Ecole Elementaire Mathieu Da Costa

5.4 km

Nearest, confirm zoning

Catholic (TCDSB) and French-language schools shown are the nearest to the building, not confirmed zoning. Check the TCDSB school locator, Viamonde or MonAvenir.

By the numbers

What units at Four Winds Condos actually trade for

$626Median sold price per sq ft, last 12 months-11% vs 2022 ($700)
25%of resales closed at or above asking, last 12 monthsRoom to negotiate
Unit typeSoldMedian priceLeasedMedian rent
2 bed4$532,0002too few

Table covers the last 24 months. TRREB MLS® System aggregates; a median is shown only with 3 or more deals, and sizes come from listing ranges. Not an appraisal: get an estimate for your unit.

Living here

Renters, Airbnb and elevators at Four Winds Condos

Do mostly owners or renters live here?

Leases 43%Sales 57%

Mix of owners and renters. Of 14 deals here in the last 24 months, 6 were leases and 8 were sales. A high lease share usually means more investor owners, more move-ins and a deeper pool of rental comparables.

Can you Airbnb a unit at Four Winds Condos?

1unit registered with the City as a short-term rental at this address

Some owners here hold City registrations, but the condo’s own declaration and rules can still forbid short stays. In Toronto you can only host in your principal residence, a whole unit for at most 180 nights a year, with a $390 yearly registration and 6% accommodation tax. You cannot buy here to run it as a full-time Airbnb. Check the condo’s rules in the status certificate before you count on it.

How reliable are the elevators?

0elevator outages of 48 hours or more reported to TSSA for this address since July 2022

Ontario requires residential buildings to report any elevator outage lasting 48 hours or more, and this address has none on record. Elevators still need modernizing every 25 to 30 years, so check the reserve fund study for the date.

Sources: TRREB MLS® System lease and sale counts; City of Toronto short-term rental registrations (Open Data, 18 Oct 2026); TSSA Residential Elevator Availability portal.

Before you buy here

Five things the listing will not tell you about Four Winds Condos

  1. Reserve fund health. Ask for the latest reserve fund study and its date. A thin fund in an older building usually means fee jumps or a special assessment.
  2. Special assessments and big repairs. Check the status certificate for planned levies and for balcony, garage, window or elevator work.
  3. Insurance deductible. Find the corporation’s deductible for water damage. If it is higher than your own policy covers, raise your coverage before closing.
  4. Fee trend. Compare this year’s budget with last year’s. Rises of 2–5% a year are typical; bigger jumps need an explanation.
  5. Lawsuits and rules. Look for legal claims against the corporation, and for rules on pets, short-term rentals and leasing.

Send me the status certificate and I will flag anything that matters before your conditional period runs out.

Get my status certificate reviewed

Watch this building

Know the moment a unit at Four Winds Condos lists or sells.

Portals tell you a listing exists. I tell you whether it is priced right for this building, which stack it is in, and what the last comparable unit actually went for.

  • New listings for sale or rent here
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Building alerts

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Eat, drink and shop nearby

Within about a 10-minute walk.

Restaurant

Big Daddy's Halal Grill

Steps away

Restaurant

Picasso Grillz Fusion Grill Kitchen

Steps away

Restaurant

Tonia's Kitchen

Steps away

Coffee

Cooper's Coffee & Bubble Tea

Steps away

Pizza

Macaan Pizzeria

Steps away

Restaurant

Mama P's Gold Coast Kitchen

Steps away

Places from OpenStreetMap. Check hours before you go.

Parks nearby

  • Four Winds Allotment Gardens
  • Fountainhead Park
  • Jack Evelyn Wiggins Park

Nearest grocery

FreshCo

1.7 km

Prices: TRREB MLS® System aggregate medians for 21-37 Four Winds Dr, last 12 months (updated 18 October 2026), compiled by Jatin Dua, Broker of Record, RE/MAX Quantum Realty Inc., Brokerage; deemed reliable, not guaranteed. Schools: TDSB school locator; Catholic and French schools: nearest by distance. Transit and scores: Walk Score® and TTC/GO station locations. Nearby places: OpenStreetMap. Distances are straight-line estimates.

Four Winds Condos is where I look when a buyer near York University needs three or four bedrooms and a budget that a new tower cannot meet. The suites at 21-37 Four Winds Drive date from the early 1970s, they are generously sized, and the fee includes parking. The records for this address also contain some contradictions, and I would sort those out before writing an offer. I’m Jatin Dua, RE/MAX Quantum Realty.

Quick answer

Four Winds Condos is a condominium at 21-37 Four Winds Drive in the York University Heights neighbourhood of North York, Toronto. Condos.ca lists it as an 11-storey high-rise built in 1972 by Cadillac Fairview Corporation (its overview also names Cadillac Development Corporation Ltd), with Percel Property Management as manager. The condominium corporation is TSCC-1749, with a recorded registration date of 20 November 1972. Condos.ca lists the maintenance fees as covering common elements, building insurance and parking.

Four Winds Condos at a glance

Address
21-37 Four Winds Dr
Storeys
11
Suites
3360
Built
1972
Developer
Cadillac Fairview Corporation
Corp #
TSCC-1749

A 1970s complex built for families, not investors

Four Winds Drive was built in the era when developers like Cadillac Fairview were putting up large suburban complexes for households, not for one-bedroom investors. You can see it in the unit mix. Of the seven suites for sale when I checked, every one had at least two bedrooms, and several had three or four bedrooms plus a den.

That is the main reason this building exists for a buyer today. A new condo near the York University and Finch West stations will give you a glossy one-bedroom; it will rarely give you a four-bedroom suite at a price an ordinary family can carry. Four Winds does, and the trade-off is a building that is more than 50 years old.

Listing addresses run from 21 to 37 Four Winds Drive, and the suites do not all look alike. Some carry low unit numbers that suggest ground-related or multi-level suites, while others are on upper floors of an apartment block. Ask your agent which kind of suite you are looking at, because the floor plan, the entrance and the parking arrangement can all differ.

The records here do not all agree

Condos.ca lists 3,360 suites for this corporation. I do not believe that number describes 21-37 Four Winds Drive; it is far too large for an 11-storey building and its neighbours, and it may be counting a wider area. Treat the suite count as unconfirmed and get the real figure from the status certificate.

The second puzzle is the corporation number. TSCC-1749 sits in a range Toronto issued in the mid-2000s, yet the recorded registration date is 1972. One explanation is that the property was built in the early 1970s and registered as a condominium later, but I have not confirmed that. If it is the case, the corporation’s own reserve fund history is shorter than the building’s age, and that is worth understanding.

There is also a conflict on amenities. One online building profile mentions a seasonal outdoor pool, while condos.ca lists only visitor parking, a parking garage, BBQs permitted and pet restrictions. Do not pay for a pool until you have seen it in the declaration and the budget.

Thinking about buying or selling here?

I work this area every week and I will give you a straight answer, including when the answer is to wait. No pressure, and no drip campaign you cannot get out of.

Call or text 833-330-1925 Send me a message

Jatin Dua, Broker of Record — RE/MAX Quantum Realty Inc., Brokerage. Not intended to solicit buyers or sellers currently under contract with another brokerage.

Fees, parking and what a 50-year-old building costs to run

The fee covers common elements, building insurance and parking. Heat, hydro and water are not listed as inclusions, so ask for actual utility bills before you compare this with an all-inclusive building nearby.

Across the active listings, fees averaged about $0.88 per square foot. Monthly fees ranged from roughly $376 to $1,051. The lowest figure is far below the rest, so check whether it reflects a different suite type or a data entry error rather than a bargain.

Age is the real cost driver. A complex from the early 1970s has been through windows, roofs, garage repairs and at least one generation of mechanical systems, or it has those projects still ahead. The reserve fund study tells you which. It is the single most important document in this purchase. Read the last few years of board minutes too, because they show which projects the board has been putting off and why.

Living in York University Heights

The daily reality here is shaped by York University. Demand for rentals is steady because students and staff want to live close to campus, which helps an investor. For an owner-occupier, it can mean more turnover in the hallways than a quieter suburban building would have.

The neighbourhood has changed a great deal since this complex was built. The subway extension and the stations it brought have made the area far easier to reach, and the data panel on this page shows the nearest stops. Black Creek Pioneer Village and the green space around the campus are part of the local landscape.

That rental demand has a financing side too. In a building near a campus, some lenders look closely at how many suites are owner-occupied and what the leasing rules allow. If you need a high-ratio mortgage, ask your lender early whether this corporation raises any questions, and get the leasing figures from the status certificate rather than guessing from the hallway.

Pets are listed under restrictions rather than as allowed. If you have a dog, read the declaration and rules before you fall in love with a suite.

What Four Winds Condos costs

Condos.ca puts the building average at about $613 per square foot. That is modest for Toronto, and it reflects both the age of the building and the large suite sizes, which pull the per-square-foot figure down.

When I checked, there were seven suites for sale and none for lease. Asking prices ran from $410,000 to $769,900. That is a lot of bedrooms for the money compared with newer buildings around the subway, but asking prices are not sale prices. My building sold report will show you what actually traded here.

When you compare fees, add the utilities that are not included back in. A newer one-bedroom nearby may have a lower fee, but it is not the same product, and per-square-foot fees in older buildings almost always look higher because they fund more repairs.

Building specifications

Building nameFour Winds Condos
Address21-37 Four Winds Dr, North York, Toronto M3J 1K7
DeveloperCadillac Fairview Corporation (overview also names Cadillac Development Corporation Ltd)
Storeys11 (as listed)
Total suitesUnconfirmed; condos.ca lists 3,360, which looks too high for this address
Condo corporationTSCC-1749
Registered20 November 1972 (as recorded)
Property managementPercel Property Management
Unit typesTwo-bedroom to four-bedroom-plus-den suites among current listings
Maintenance feesAbout $0.88 per sq ft across active listings
Fees includeCommon elements, building insurance and parking

Amenities at Four Winds Condos

Parking garageVisitor parkingBBQs permittedPet restrictions

This is not an amenity building. What you are buying is space and parking, and if a pool or gym matters to you, confirm what actually exists and what it costs to run before you count it.

Jatin’s honest take on Four Winds Condos

Who this building suits

Families who need three or four bedrooms near York University, and investors who want steady student and staff rental demand without paying new-build prices. It also suits buyers who would rather have a big suite in an older building than a small suite in a new tower.

What I’d want you to check

Get the status certificate and the reserve fund study, and read them line by line. Confirm the real number of suites in the corporation, the registration history behind TSCC-1749, what the fee actually covers, and whether a pool exists. Ask about windows, the garage, balconies and plumbing risers, which are the big-ticket items in a building of this era. Check the rules on pets and leasing.

The value question

At around $613 per square foot with parking included, the price per bedroom is hard to beat near the subway. The value holds only if the reserve fund is healthy and the major repairs are funded. If the documents show a shortfall, the low price is simply the market pricing in a future bill, and I would walk away or negotiate hard.

Free building report: Four Winds Condos

Send me your email and I’ll put together a current report on Four Winds Condos — real sold comparables, what’s listed right now, and what the maintenance fees actually cover.

  • Every sale in the building over the last 12 months
  • Current active listings and asking prices
  • Maintenance fee breakdown and what’s included
  • My read on which exposures and floors hold value

Tell me what you are planning

Three quick answers so I come back with something useful, usually the same day.

Your details go to me only, never sold or shared. Prefer a set time? Book a 15-minute call.

Thinking about buying or selling here?

I work this area every week and I will give you a straight answer, including when the answer is to wait. No pressure, and no drip campaign you cannot get out of.

Call or text 833-330-1925 Send me a message

Jatin Dua, Broker of Record — RE/MAX Quantum Realty Inc., Brokerage. Not intended to solicit buyers or sellers currently under contract with another brokerage.

Four Winds Condos — frequently asked questions

Who built Four Winds Condos?

Condos.ca names Cadillac Fairview Corporation as the developer, and its overview also refers to Cadillac Development Corporation Ltd. Both are part of the same large developer family that built extensively in Toronto in that era.

How old is Four Winds Condos?

It is recorded as built in 1972, with a registration date of 20 November 1972. The corporation number, TSCC-1749, is in a range normally issued in the mid-2000s, so ask the status certificate to confirm the registration history.

How many suites are at Four Winds Condos?

Condos.ca lists 3,360, which I think is far too high for 21-37 Four Winds Drive. Treat it as unconfirmed and get the real count from the corporation.

What do the maintenance fees include?

Condos.ca lists common elements, building insurance and parking. Heat, hydro and water are not listed, so ask for utility costs.

Is parking included?

Parking is listed among the fee inclusions. Confirm whether the suite you are buying has an owned or assigned space and where it is.

Are pets allowed?

Condos.ca lists pet restrictions. Read the declaration and rules for the exact limits before you buy.

Does Four Winds have a pool?

One online profile mentions a seasonal outdoor pool, but condos.ca does not list one. Confirm it in the status certificate and budget.

Who manages Four Winds Condos?

Condos.ca lists Percel Property Management. Confirm the current manager in the status certificate.

Who is Four Winds Condos best for?

Families who need three or more bedrooms near York University and investors who want steady rental demand at a lower price per square foot.

How big are the suites?

Current listings run from two bedrooms to four bedrooms plus a den, with some two-bedrooms in the 900 to 999 sq ft range. Floor plans vary between addresses, so check each one.

How much do condos at Four Winds Condos sell for?

Over the last 12 months the median resale at Four Winds Condos was $532,000, across 4 sales. The typical unit sold in 23 days at about 98% of the asking price. That works out to roughly $626 per square foot.

How much is rent at Four Winds Condos?

The median lease at Four Winds Condos over the last 12 months was $2,400/mo, from 4 leases. Units typically leased in 45 days.

What does each unit type cost at Four Winds Condos?

Over the last 24 months: Two-bedrooms sold for a median $532,000. Each median uses three or more deals.

Are prices at Four Winds Condos up or down since 2022?

Down about 11%. The median sold price per square foot was $700 in 2022 and $626 over the last 12 months. Pricing off 2022 comparables is the most common mistake sellers make here.

What rental yield does Four Winds Condos offer an investor?

At a median price of $532,000 and a median rent of $2,400 a month, the gross yield is about 5.4%, before maintenance fees, property tax, insurance and mortgage interest. Net cash flow depends on the fee and your down payment, so run the numbers for the exact unit.

Do mostly owners or renters live at Four Winds Condos?

A mix of both. Of the deals here in the last 24 months, 43% were leases and 57% were sales.

Can you Airbnb a unit at Four Winds Condos?

Only in limited cases. Toronto allows short-term rentals only in your principal residence, a whole unit for at most 180 nights a year, with a $390 yearly City registration and 6% accommodation tax. The City’s register shows 1 active short-term rental registration at this address. The condo’s declaration and rules can ban short stays outright, so check them in the status certificate.

Has Four Winds Condos had elevator outages?

None on record. Ontario requires residential buildings to report elevator outages of 48 hours or more to TSSA, and this address has no reported outage since July 2022.

What schools is Four Winds Condos zoned for?

For TDSB public schools, the address is zoned for Derrydown Public School (Elementary, JK–5), Elia Middle School (Middle, Gr 6–8), C W Jefferys Collegiate Institute (High school, Gr 9–12). Catholic and French-language schools are listed on this page by distance. Boundaries change, so confirm with the board before you buy.

What is the closest subway or GO station to Four Winds Condos?

The nearest subway is Finch West station (Line 1 Yonge–University), 0.6 km away; the nearest GO station is Downsview Park GO on the Barrie line, 2.0 km; the closest bus is the Keele (TTC bus). Distances are straight-line from the building.

What is the Walk Score of Four Winds Condos?

Walk Score 88, Transit Score 79 and Bike Score 83. Most daily errands can be done on foot.

What restaurants and shops are near Four Winds Condos?

Within about a 10-minute walk: Big Daddy's Halal Grill (Restaurant), Picasso Grillz Fusion Grill Kitchen (Restaurant), Tonia's Kitchen (Restaurant), Cooper's Coffee & Bubble Tea (Coffee), Macaan Pizzeria (Pizza). The closest grocery store is FreshCo, 1.7 km away.

Which parks are near Four Winds Condos?

Four Winds Allotment Gardens, Fountainhead Park, Jack Evelyn Wiggins Park are the closest green spaces.

What is my unit at Four Winds Condos worth?

Use the free AI estimator at the top of this page. It uses this building’s own recent sales and adjusts for floor, view and parking, and your number appears instantly. For a written CMA, I will price your exact unit against the latest comparable sales.

How do I find out when a unit at Four Winds Condos lists or sells?

Join the building alerts on this page. I watch this building by hand and will tell you when a unit lists, sells or drops in price, with my read on whether it is priced right.

Still have a question about Four Winds Condos?Ask me directly: a 15-minute call, no pressure.
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Looking at Downsview, Weston, York University Heights, Rexdale and northwest Toronto more broadly? Start with my Toronto community guide — the neighbourhoods, what each pocket is like, and how they compare.

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Reading recent condo sales…

Estimated market value

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Most likely $0 · about $0 per square foot

What moved the number

Starting from what comparable units in your area sell for, here’s what your specifics added or subtracted.

Market context

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Average condo sale, your area
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Days on market

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Two units, same floor plan,
$90,000 apart.

That happens constantly in condos — one has the parking, the right exposure, or a board that keeps the reserve fund healthy. A model can’t see your status certificate. I can.

How this works — your estimate comes from a model built on recent Toronto & GTA condo sale data, weighting area, size, layout, floor, exposure, view, parking, locker, age and condition. It is an automated estimate for information only — not an appraisal and not a Comparative Market Analysis. Condo values also depend on the building’s reserve fund, maintenance fees, recent special assessments and status certificate, none of which a model can read. Ask me for a written CMA before you make a decision.

About the author — Jatin Dua, Toronto condo broker

I’m Jatin Dua, Broker of Record at RE/MAX Quantum Realty. I work condo buildings across Toronto and the GTA every week, including Downsview, Weston, York University Heights, Rexdale and northwest Toronto. What buyers and sellers usually need is someone who knows the individual buildings: which exposures get the light, which corporations keep healthy reserve funds, and which units are priced past what they will appraise for.

If you’re buying or selling at Four Winds Condos, I’ll give you the honest version — including when I think you should walk away. Reach me at [email protected] or 833-330-1925, or book a free consultation.

More Downsview, Weston, York University Heights, Rexdale and northwest Toronto building guides: 1 San Carmeloway Townhouses · 10 Eddystone Avenue Condos · 100 Charlton Settlement Avenue Townhouses · Rory Road Townhomes · 121 Charlton Settlement Avenue Townhouses · 125 Isaac Devins Condos

More resources: GTA condo directory · Building sold report · Book a call

Figures on this page were compiled from publicly available sources including condos.ca, strata.ca, City of Toronto open data and developer materials as at October 2026, and are provided for general information only. Sources frequently disagree on unit counts, storeys, square footage and maintenance-fee inclusions, and pricing changes constantly — where sources conflicted I’ve said so rather than picking one. Nothing here is an appraisal, a valuation, or a substitute for a status certificate reviewed by your lawyer. Verify all figures independently before making a decision. Jatin Dua, Broker of Record, RE/MAX Quantum Realty. Not intended to solicit buyers or sellers currently under contract. E. & O.E.

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© 2026 Jatin Dua, Broker of Record, RE/MAX Quantum Realty Inc., Brokerage. The building data on this page was compiled and verified by Jatin Dua. Reproduction or republication, in whole or in part, requires written permission. To request permission, call 833-330-1925.

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