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148 Winchester Rd E, Whitby — Rare 15,200 sqft Brooklin Lot Inside the Community Secondary Plan

Aidan Holt4 min read

Aerial view of 148 Winchester Rd E showing the 15,200 sqft Brooklin lot

List Price: $795,000 MLS#: E13064912 Lot: 80 x 190 ft (15,200 sqft) Type: Detached Bungalow + Finished Basement (Side Entrance) Beds / Baths: 2+1 / 2 Status: New on Market Listing on Realtor.ca: View Listing

Why this listing is different

Most Brooklin houses come with Brooklin lots — 30 to 50 ft frontages. This one comes with 80 ft of frontage and a 190 ft deep lot. That's 15,200 square feet — roughly 3-4x the size of a typical Brooklin lot.

It's also inside the Brooklin Community Secondary Plan, which is the planning framework Whitby uses to guide where the town grows next. Lots inside that plan have a different ceiling than lots outside it. That's the part most buyers and most agents miss.

The bungalow on it is solid, livable, and tenanted-ready: 2 beds up, 1 down, finished basement with a side entrance, central A/C, gas forced-air heat, 4 parking spots, no shared driveway. Vacant. Immediate possession.

Front exterior of 148 Winchester Rd E in Whitby

Three different buyers, three different math problems

This property doesn't have one "right" buyer. It has three.

1. The developer

For builders and small-scale developers, the math here isn't about the house — it's about the land. 80 x 190 ft inside a Secondary Plan area is the kind of lot you build a future on, not a Saturday project.

What matters to a developer:

  • Frontage: 80 ft
  • Depth: 190 ft
  • Total: 15,200 sqft
  • Located inside Brooklin Community Secondary Plan
  • Cross streets: Anderson / Winchester
  • Steps to Winchester PS
  • Less than 5 minutes to Hwy 407 access

If you're building in Whitby and your acquisition team isn't already looking at this, they should be.

Aerial view showing the depth of the 15,200 sqft lot

2. The investor

For investors, the math is income today + upside tomorrow.

Income today: A 2-bed bungalow plus a 1-bed basement with a separate side entrance is a clean two-unit setup. Brooklin rent comps support solid revenue out of the gate, with low operational headache thanks to the bungalow form factor.

Upside tomorrow: You're holding a 15,200 sqft lot in a Secondary Plan area in one of Whitby's fastest-growing neighborhoods. Cash-flowing while you wait is the cleanest version of this trade.

Finished basement with separate side entrance

3. The owner-occupant

For first-time buyers, downsizers, or families looking to renovate — this is rare. You don't usually get this much land at this price point, this close to good schools, this close to the 407.

  • Winchester PS is walking distance
  • Forced-air gas + central A/C
  • Asphalt shingle roof
  • Alum siding (low maintenance)
  • 4 parking spots (no garage, but generous private drive)
  • Bungalow form = single-floor living, future accessibility upside
  • Vacant + immediate possession

For families: room to expand, room to garden, room to grow.

Living room interior

Kitchen with dining area

What it would cost to operate (rough math)

For an owner-occupant at 20% down:

ItemAmount
Purchase price$795,000
Down payment (20%)$159,000
Mortgage (5-yr fixed @ ~5.0%, 25-yr am)~$3,710/mo
Property tax (2025 actual)$5,555/yr → $463/mo
Insurance (est.)~$120/mo
Utilities (gas + hydro + water)~$300/mo
Estimated total monthly carry~$4,593/mo

For an investor running the basement as a rental:

  • Brooklin 1-bedroom basement comps: ~$1,800-2,200/mo
  • Net carry after basement income: ~$2,400-2,800/mo
  • Live upstairs, rent the basement = effective housing cost cut roughly in half

All numbers above are illustrative only. Always verify with your mortgage broker, accountant, and a real estate professional. Rates and rents change.

Bedroom

Brooklin context

Brooklin is one of Whitby's fastest-changing neighbourhoods. Population growth, school growth, infrastructure growth — all moving the same direction. The Secondary Plan was put in place specifically to manage that growth thoughtfully, which means the lots inside it are the lots town planning has flagged for future intensification.

That's not a guarantee of anything — every project still needs proper approvals, due diligence, and time. But the planning framework is on this side of the property line.

Aerial view of property in context of Brooklin neighborhood

How to see the space

The fastest way: text me at (647) 557-5358 and I'll send a link to book a showing. Lockbox access for agents.

You can also email aidan@tirupopalgroup.com.

Listing on Realtor.ca: View 148 Winchester Rd E on Realtor.ca MLS#: E13064912

If you're a developer or investor who wants the full lot package — site plan, frontage, depth, Secondary Plan documentation — I can email you the package. Just say "Winchester package" in your reply.


Posted by Aidan Holt — Sales Representative with Tiru Popal Group at RE/MAX Metropolis Realty. I work with developers, investors, and owner-occupants across the GTA, with a focus on properties where the lot tells a different story than the house. If you're exploring Whitby or Durham region opportunities, book a 15-min strategy call or text me directly at (647) 557-5358.

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