59 High Park Blvd 4 Unit Apartment Building Offered at $4,950,000 CAD at a 3.51% Cap Rate Toronto, ON M6R 1M9

59 High Park Blvd
A rare and flexible investment opportunity in one of Toronto’s most sought-after neighbourhoods, 59 High Park Blvd is a century home offering over 5,000 sq. ft. of living space across a grand three-storey main house plus a detached one-bedroom pool house.
Currently configured as four self-contained apartments, the main residence offers remarkable versatility for investors, end users, or multigenerational living. The home can also be easily converted back to a single-family residence by opening one small wall on the main floor, restoring access to the original central staircase connecting all levels.
The property features 9 bedrooms and 7 bathrooms in the main house, plus a detached one-bedroom pool house with independent in-floor heating, gas fireplace, and access to the backyard oasis. The outdoor space includes natural stone walkways, new fencing, a pool, and a 15-foot swim spa hot tub with a 250,000 BTU pool heater.
For buyers seeking both lifestyle and income, the property offers several attractive use options. Live on the main floor with exclusive use of the backyard, pool, and pool house while renting the basement, second floor, and loft apartments. Occupy the main and second floors for additional bedrooms and access to a 400 sq. ft. second-floor deck, while renting the loft and basement. Or enjoy the main, second, and third floors while generating income from the basement apartment.
Seller-provided income projections show substantial potential from both short-term and long-term rental strategies. Based on 180 days of short-term rental use, projected gross income is approximately $281,340 annually. Estimated long-term monthly rents total approximately $17,500 per month, or $210,000 annually, including the loft, second floor, main floor, basement, and pool house.
Notable mechanical and comfort upgrades include a high-efficiency Viessmann boiler for the main house, snow-melt heating under all stone walkways, a backup boiler system, heat pump air conditioning in all apartments, independent heating for the pool house, and premium outdoor amenities designed for year-round enjoyment.
A truly unique High Park property offering scale, character, income potential, and multiple paths for future use: investment property, owner-occupied income property, multigenerational residence, or restored single-family estate.