$1,779,000
27 Hillsboro Avenue, Toronto, ON M5R 1S6
Annex · C02
Listing courtesy of ROYAL LEPAGE SIGNATURE REALTY
Annex · C02 · M5R 2X6
$2,199,000
$628 / sq ft1 months on market
A five-unit Annex Semi Detached property with the kind of envelope and location that is not being built at today's replacement cost. Legal four-plex above grade plus a legal non-conforming lower suite across 5,225+ sq.ft. on Walmer Road, one of the most tenured income streets in central Toronto. In-place rents sit well below current Annex benchmarks. Income reflects long-tenured tenancies rather than today's market. The unit mix is differentiated - not five interchangeable bachelors. Unit 2 on the main floor is a 1,396 sq.ft. parlour-floor residence with a 21-foot living room, fireplace, oversized kitchen, and a 17-foot principal bedroom. Unit 5 on the third floor (1,171 sq.ft.) is configured with two kitchens, two four-piece baths, two primary bedrooms, an office, and a dining room - lives as one generous suite today. Unit 4 (758 sq.ft.) has a four-piece ensuite, walk-in closet, and living space. Unit 3 (710 sq.ft.) is a full one-bedroom with fireplace, kitchen, and dining. Unit 1 in the lower level (1,191 sq.ft., legal non-conforming) reads as a proper apartment: one-bedroom plus 15-foot den, full kitchen, three-piece bath, and private utility room. Three distinct buyer paths converge here. For the investor, five legal income streams on a single folio, a demand floor set by U of T, downtown professionals, and the Dupont / Spadina subway corridor. For the owner-investor - Multiple units are suitable and are amongst the most substantial owner's suites found inside a purpose-built Annex income property; live in it and let the other four units carry the debt while optionality is preserved. For the long-view buyer planning a single-family reversion - 5,225+ sq. ft. of interior envelope is a credible footprint for a top-of-market Annex restoration, and the existing plumbing stacks, kitchens, and floor plates make either path possible without starting from zero. Walking distance to Bloor Street, Casa Loma, the University of Toronto, and the Spadina subway line.
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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 in line with comparable listings — about 44% 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 $2,199,000. Rates current as of September 2026; confirm the final figure with your real estate lawyer.
Listing courtesy of BOSLEY REAL ESTATE LTD.. 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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$1,779,000
Annex · C02
Listing courtesy of ROYAL LEPAGE SIGNATURE REALTY
$1,999,999
Annex · C02
Listing courtesy of HOMELIFE LANDMARK REALTY INC.
$2,389,000
Annex · C02
Listing courtesy of SUTTON-HEADWATERS REALTY INC.