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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. 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, cafs 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. (id:58753)
St. Clair/Oakwood/Dufferin
Source: Public Records
| Street Address | Beds | Baths | Sold Date | List Price |
|---|---|---|---|---|
| 27 PENWOOD CRESCENT | 8 | 11 | Jun 06, 2026 | $12,350,000 |
| 83 JOHN GARLAND BOULEVARD | 5 | 3 | May 17, 2026 | $995,000 |
| 24 RANEE AVENUE | 6 | 5 | May 31, 2026 | $2,149,900 |
| 35 PATON ROAD | 3 | 2 | Jun 09, 2026 | $1,099,000 |
| 49 Holland Park Avenue, York ON M6C 1M2 | 0 | 0 | May 29, 2026 | $949,000 |
| 49 Holland Park Avenue, York ON M6C 1M2 | 0 | 0 | May 29, 2026 | $949,000 |
Discover key demographics, population statistics, and environmental insights for the Toronto (oakwood Village), ON area.
96/100
Walker's Paradise
Walk Score ®
79/100
Excellent Transit
Transit Score ®
74/100
Very Bikeable
Bike Score ®
Daily errands do not require a car. Transit is convenient for most trips. Biking is convenient for most trips.
13 nearby routes: 12 bus, 1 rail, 0 other
The average walkability score in the surrounding area is Walk Score: 81/100, Transit Score: 78/100, Bike Score: 71/100.
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393A ARLINGTON AVENUE
Source: Realty.com
185 GLENHOLME AVENUE, Toronto (Oakwood Village), ON M6E3C5 in Toronto (Oakwood Village), ON M6E3C5 is a single family residence listed at $2,749,000. Highlights include 6 bedrooms, 4 bathrooms. Realty.ca has 50 photos, sales history, school insights, and mortgage tools for this listing.
Realty.com has 50 photos of 185 GLENHOLME AVENUE.
The full address for this home is 185 GLENHOLME AVENUE, Toronto (Oakwood Village), ON M6E3C5.
185 GLENHOLME AVENUE has been listed on Realty.com since Wed June 10, 2026
Daily errands do not require a car. Transit is convenient for most trips. Biking is convenient for most trips.
The average walkability score in the surrounding area is Walk Score: 81/100, Transit Score: 78/100, Bike Score: 71/100.
Listing provided courtesy of:
ORION REALTY CORPORATION
Listing agent:
RYAN GOSSIN
This content last refreshed on 2026-06-13 21:43:55. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.