$1,999,999
35 Dupont Street, Toronto, ON M5R 1V3
Annex · C02
Listing courtesy of HOMELIFE LANDMARK REALTY INC.
Annex · C02 · M5R 1S6
$1,779,000
$1,186 / sq ftListed yesterday
27 Hillsboro Avenue Opportunity Meets Lifestyle in the Heart of Avenue & DavenportWelcome to a rare and versatile offering in one of Toronto's most coveted neighbourhoods. 27 Hillsboro Avenue is a duplex-zoned property with exceptional flexibility for investors, end-users, or visionaries looking to unlock long-term value in this century brick home. The home features a shared driveway with parking for two vehicles-a true bonus for this location. Main level freshly updated with new flooring, paint, and modern lighting. Lower level recently updated, new windows and water proofing.currently leased. Each upper level enjoys its own private porch and includes a sun porch, offering wonderful bonus family space, a home office, or a cozy reading retreatThe basement in-law suite currently leased.Laundry and utilities are shared, keeping operations straightforwardFrom a future-planning perspective, the options here are compelling:Keep the current duplex configuration with basement suite,Restore to a stunning single-family home (all stairways are intact),Upgrade or reposition the property to maximize its potentialAn initial zoning review indicates potential 6-plex compliance (buyers to confirm independently), making this an exciting prospect for those exploring gentle density and long-term development upside.All of this is wrapped in an unbeatable location: steps to Ramsden Park, minutes to Rosedale subway station, and a short walk to Yorkville, with its world-class dining, shopping, and culture.Live in it. Rent it. Reimagine it. This is a property that grows with your goals-and opportunities like this on Hillsboro Avenue don't come around often. Book your showing and explore the possibilities.
15 rooms. Dimensions as published by the listing brokerage.
| Room | Level | Dimensions | Features |
|---|---|---|---|
| Living Room | Main | 4.50 × 3.02 m14.8 × 9.9 ft | Fireplace |
| Dining Room | Main | 4.50 × 3.02 m14.8 × 9.9 ft | Window |
| Kitchen | Main | 2.88 × 2.28 m9.4 × 7.5 ft | Window |
| Bedroom | Main | 3.19 × 2.52 m10.5 × 8.3 ft | Window |
| Bedroom 2 | Main | 3.82 × 2.54 m12.5 × 8.3 ft | Window |
| Living Room | Upper | 4.49 × 3.00 m14.7 × 9.8 ft | Window |
| Dining Room | Upper | 2.79 × 2.65 m9.2 × 8.7 ft | Window |
| Kitchen | Upper | 2.90 × 2.29 m9.5 × 7.5 ft | — |
| Primary Bedroom | Upper | 4.49 × 3.00 m14.7 × 9.8 ft | Fireplace · W/O To Balcony |
| Bedroom 2 | Upper | 3.85 × 2.44 m12.6 × 8.0 ft | Window |
| Bedroom 3 | Upper | 3.19 × 2.49 m10.5 × 8.2 ft | Window |
| Living Room | Lower | 4.67 × 2.74 m15.3 × 9.0 ft | Window |
| Kitchen | Lower | 3.95 × 2.78 m13.0 × 9.1 ft | Eat-in Kitchen |
| Bedroom | Lower | 5.33 × 3.42 m17.5 × 11.2 ft | Window |
| Utility Room | Lower | 6.35 × 2.99 m20.8 × 9.8 ft | Combined w/Laundry · Window |
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What this home costs beyond the asking price, and how that price compares to what else is on the market.
This home is priced below most comparable listings — about 22% of comparable multiplex listings in Annex are asking less.
Based on 9 comparable active multiplex listings in Annex. These are asking prices, not sale prices.
Estimate only. Excludes CMHC insurance premiums, which apply below 20% down, and does not constitute a mortgage approval or an offer of credit.
Payable on closing, on top of the purchase price.
An estimate on the asking price of $1,779,000. Rates current as of September 2026; confirm the final figure with your real estate lawyer.
Listing courtesy of ROYAL LEPAGE SIGNATURE REALTY. Listing data is provided in part by the Toronto Regional Real Estate Board (TRREB) and is deemed reliable but is not guaranteed accurate. Information is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties. Data is updated every 15 minutes.
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$1,999,999
Annex · C02
Listing courtesy of HOMELIFE LANDMARK REALTY INC.
$1,699,000
Annex · C02
Listing courtesy of Johnston & Daniel