Detached Oakwood Village 4-bed with legal-style basement suite on 125-foot L-shaped lot
A detached 4-bed, 4-bath in Oakwood Village with a separately entranced basement suite, full second kitchen, and a 125-foot deep L-shaped lot offering future redevelopment optionality. Listed at $1,599,000 with an estimated cap rate of 0.69%, the property is structured as an end-user or long-hold appreciation play, not a cash-flow asset.
Anatoli Chtcherbatov
Analyst · Sutton Group Admiral Realty
List price
$1,599,000
Cap rate
+0.69%
Est. monthly rent
$3,350
Source: comparables_widened
Est. net spread
+$365K
6mo hold
Annualized ROI
+45%
preliminary
The Deal
A detached 4-bed, 4-bath in Oakwood Village with a separately entranced basement suite, full second kitchen, and a 125-foot deep L-shaped lot offering future redevelopment optionality.
Fix-and-flip projection
The spread, before the buy-and-hold math.
Preliminary · adjust scope & uplift
Renovation scope
Projection
Preliminary estimate. Renovation costs use 6Yield default per-sqft figures. Post-renovation value is modeled as a multiple of list price — replace with comparable post-renovation sales for higher precision. Carrying costs include property tax, condo fees if any, and insurance; financing costs not yet modeled.
Section · Buy-and-hold backup
If you held instead. The carrying math, side by side.
Each column shows the actual monthly cash flow and cash-on-cash return at that leverage. Click a column for the full breakdown.
Acquisition
| Down payment | $559,650 |
| Mortgage principal | $1,039,350 |
| Land transfer tax | $23,985 |
| Closing costs | $23,985 |
| Total acquisition | $607,620 |
Monthly cash flow
| Estimated rent | +$3,350 |
| Operating expenses | -$2,434 |
| Mortgage payment | -$6,070 |
| Net cash flow | -$5,154/mo |
Expense breakdown
| Property tax | $0/mo |
| Vacancy allowance | $168/mo |
| Maintenance reserve | $1,333/mo |
| Insurance | $666/mo |
| Property management | $268/mo |
Math by deterministic Python calculator. Rate 4.99% over 25 years. Rent source: comparables_widened (24 comps).
Breakeven
This property turns cash-flow positive at 90.2% down.
Run your own scenario
Move the assumptions. See the math live.
Live result
All figures are estimates only and do not constitute financial advice. The sliders use the same math as the locked five-scenario calculator; only assumptions change. Total acquisition includes the down payment, land transfer tax ($23,985), and closing costs ($23,985).
Section · Investment Thesis
Why this property.
265 Glenholme Avenue is a detached 4-bed, 4-bath architectural home in Oakwood Village, listed at $1,599,000. The property includes a separately entranced basement suite with a full second kitchen, renovated bath, heated floors, and a private entry, providing in-law or accessory rental flexibility. The lot is described as a 125-foot deep L-shaped parcel with dual street access and a 3-car parking pad, which the listing identifies as offering possible future redevelopment optionality. With a walkability score of 92/100 and access to the St. Clair Streetcar, Ossington Bus, and the new Eglinton LRT line, the location underpins long-term owner-occupier and family-rental demand.
On the rent side, the estimated monthly rent of $3,350 (drawn from 24 widened comparables) produces gross annual rent of $40,200, annual NOI of $10,989, an estimated cap rate of 0.69%, and a gross yield of 2.51%. These metrics make clear that this is not a yield asset at the current list price; the investment case rests on land value, redevelopment optionality, and Oakwood Village appreciation rather than operating income.
Leverage sensitivity is high and the property is deeply negative on carry at every financed scenario. At 20% down ($319,800), the monthly mortgage is $7,470.62 and estimated monthly cash flow is -$6,554.87, with cash-on-cash of -21.39%. At 35% down, monthly cash flow improves to -$5,154.13 (cash-on-cash -10.18%); at 50% down, -$3,753.39 (-5.31%); and at 75% down, -$1,418.82 (-1.37%). The property only crosses into positive monthly cash flow at 100% cash, where estimated monthly cash flow is +$915.75 and cash-on-cash is 0.67% on a total acquisition cost of $1,646,970. The minimum recommended structure for neutral or positive carry is therefore an all-cash purchase.
Given the negative carry across all leveraged scenarios and the thin all-cash yield, this is best viewed as an end-user home with rental optionality, or a long-hold (60+ months) appreciation and redevelopment play for a well-capitalized buyer. Investors should underwrite to land value and the L-shaped lot's redevelopment potential, not to operating cash flow. Mortgage figures assume a 4.99% rate over 25-year amortization.
Key features
- Detached 4-bed, 4-bath with separately entranced basement suite and full second kitchen
- 125-foot deep L-shaped lot with dual street access and 3-car parking pad
- Walkability score 92/100; steps to St. Clair Streetcar, Ossington Bus, Eglinton LRT
- Possible future redevelopment optionality cited in listing
- Primary suite occupies entire top floor with skylights, soaker tub, walk-in closet, ductless A/C
- Fully finished basement with heated floors, renovated bath, private entry
Original MLS description
Gorgeous Glenholme! 4 Bed, 4 Bath Architectural Gem with a separately entranced basement suite with an extra full kitchen in a highly sought-after family-friendly neighbourhood! Set on an impressive 125-foot deep L-shaped lot with dual street access and a 3-car parking pad. The chef's kitchen is the true centrepiece of the home, featuring expansive windows, marble countertops, abundant cabinetry, & premium appliances: Porter & Charles stove, Miele dishwasher, KitchenAid Professional Series S/S Fridge. 2nd Level has 3 great-sized bedrooms plus an amazing sunroom big enough for an at-home gym with bike AND treadmill. Built-in bookcases in 3rd bed, ideal for home office. Beautiful charm everywhere: wainscoting, custom trim, a secret staircase book nook, new carpet stair runner, fresh paint and a dramatic sloped-staircase window that brings in natural light and architectural character. The entire top floor is dedicated to the primary bedroom featuring a spa-inspired soaker tub, multiple skylights, two vanities, a separate glass shower, beautiful built-ins, a walk-in closet and extra ductless A/C. The fully finished basement has private entry, a fully equipped kitchen, renovated full bath, heated floors, 2 storage closets, & a flexible layout ideal for in-law living or great income potential. Beautiful Oakwood Village, walkability score of 92/100 with great access to transit, steps to St. Clair Street Car, Ossington Bus, New Eglinton LRT line, so daily errands & weekend fun is a breeze! What do the Sellers love most about this home? The warm "welcome home" feeling, the sun-filled interiors from skylights and oversized windows, the oversized backyard oasis, and the stunning wood fireplace for cozy winter nights. Great main floor mudroom at the back of the house adds extra functionality. Possible future redevelopment with L-Shaped Lot! Minutes from St. Clair West, on a big tree-lined stret, this is truly a beautiful forever home, ready for the next family to call it hom (42896626)
All photos
32 additional · click any to expand
Section · Neighborhood
Where it sits.
Oakwood Village
Oakwood Village sits just north of St. Clair West and benefits from a walkability score of 92/100, with steps to the St. Clair Streetcar, Ossington Bus, and the new Eglinton Crosstown LRT line. The area has seen steady gentrification driven by transit investment, proximity to downtown Toronto, and demand for detached family homes within the old City of Toronto boundary.
The LRT corridor is a structural demand driver for both end-user resale and long-term rental tenancy, while the tree-lined residential streets continue to attract family buyers priced out of adjacent Wychwood and Hillcrest pockets.
Section · Risk
What could go wrong.
Honest framing of unknowns, assumptions, and downside scenarios.
High leverage sensitivity: property is cash-flow negative at 20%, 35%, 50%, and 75% down scenarios.
Only reaches positive monthly carry at 100% cash, and even then cash-on-cash is just 0.67%.
Estimated cap rate of 0.69% and gross yield of 2.51% are well below typical investor thresholds; investment case depends on appreciation and redevelopment optionality, not income.
Property tax shown as $0 in supplied financials; buyers should verify actual municipal tax burden, which will further reduce cash flow once applied.
Redevelopment potential of the L-shaped lot is described in the listing but is subject to City of Toronto zoning, severance, and permitting outcomes that are not guaranteed.
Rent estimate derived from widened comparables (24 comps), which can introduce variance versus the subject's actual achievable rent.