Listed by Orion Realty Corporation.

185 Glenholme Avenue is a Detached, 2 1/2 Storey and is currently for Sale @ $2,749,000. Taxes in 2026 were $10,709.99.

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Renovated top-to-bottom with exceptional care, this rare legal duplex offers incredible scale, flexibility and income potential in one of Toronto's most connected midtown pockets. The 2 1/2 Storey on 185 Glenholme Avenue has 4 bedrooms, 4 bathrooms, and is located on a 124.28 x 36.5 ft lot in the community of Oakwood Village . Floor plans show approx. 3,732 sq ft of measured interior floor area across all levels, including approx. 2,800 sq ft above grade plus a substantial 932 sq ft lower level, with additional structural, outdoor and auxiliary areas further enhancing the overall footprint. Ideal for multi-generational living, owner-occupancy with income, or a turn-key investment. Steps from St. Clair Ave W, TTC, parks, shops, cafés and everyday amenities, this character-filled 4+2 bedroom home features two separate property entrances, including rare dead-end street access, creating uniquely convenient access, privacy and parking with 2.5 detached garage spaces. The sun-filled interior blends historic charm with extensive modern upgrades, anchored by exposed brick and a striking spiral staircase and generous principal rooms. The 2-bedroom main floor unit provides immediate income potential with high-quality tenants already in place. The expansive two-level owner's suite offers generous living space, with a spectacular third-floor principal retreat with walk-out to an oversized private terrace - a rare elevated outdoor escape in the heart of the city.Outdoors, enjoy a private backyard oasis with beautifully landscaped space for lounging, dining and entertaining. The underpinned lower level is a true extension of the home, featuring impressive 8-ft ceiling heights, exposed structural steel beams, a 20 x 14.5 ft home gym, 20 x 12 ft recreation room, finished storage/flex space, 3-piece bath, dedicated mechanical room and premium hydronic in-floor radiant heating throughout. A rare offering with legal income, exceptional living space, major structural upgrades, private outdoor space, exceptional access, parking, and multiple ways to live, work and invest in a walkable, transit-connected Toronto neighbourhood.

2 Fridges, 2 Electric Ovens, 2 Dishwashers, 2 Microwaves, Stainless Steel Range Hood, 3 sets of washer/dryer (Basement, Ground Floor, 3rd floor). All Existing Electronic Light Fixtures, All Existing Window Coverings and Rods, B/I Cabinets, Central Air Conditioning Equipment, Tankless/On-Demand Water Heating System. 200 Amp.

The address 185 Glenholme Avenue was listed for sale (MLS# C13427712) on Wednesday, June 10, 2026.