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Why choose between a premium family home and an income property when you can have both? Live in a house-sized owner's residence while generating meaningful income from a separate legal suite. This rare, fully renovated legal duplex offers the scale, character, parking, outdoor living and flexibility of a substantial single-family home, with built-in rental income. The expansive owner's suite spans nearly 3, 000 sq ft across the upper and lower levels, creating an impressive private home with multiple living zones, generous principal rooms, exposed brick, a striking spiral staircase, and a spectacular third-floor primary retreat with walk-out to an oversized private terrace. Ideal for buyers who want elevated everyday living, room to grow, and the ability to offset carrying costs without compromising their own space. The separate 2-bedroom main floor unit is currently leased at $2, 950/month, providing immediate income from quality tenants already in place. The lower level is currently enjoyed as a substantial extension of the owner's residence, featuring impressive 8-ft ceiling heights, exposed structural steel beams and hydronic in-floor radiant heating. For buyers seeking additional income or multi-unit flexibility, permits are already available for triplex conversion, giving the next owner the choice to maintain the expansive primary suite or pursue the approved conversion plan. Steps from St. Clair Ave W, TTC, parks, shops & cafs, the property offers two separate entrances, rare dead-end street access, and 2.5 detached garages (Glenholme & Glenhurst Access).Outdoors, enjoy a private landscaped backyard designed for lounging, dining and entertaining. A rare opportunity to own a beautifully upgraded, character-filled home with the scale and comfort of a premium primary residence, the security of rental income, private outdoor space, excellent parking, and multiple ways to live, work and invest in a walkable, transit-connected Toronto neighborhood. ** This is a linked property.** (id:58753)
St. Clair/Oakwood/Dufferin
Source: Public Records
| Street Address | Beds | Baths | Sold Date | List Price |
|---|---|---|---|---|
| 71 YORKVIEW DRIVE | 5 | 6 | Jun 30, 2026 | $3,498,000 |
| 12 KING MAPLE PLACE | 6 | 3 | Jun 16, 2026 | $2,800,000 |
| 27 DELL PARK AVENUE | 3 | 2 | Jun 20, 2026 | $1,495,000 |
| 505 SOUDAN AVENUE | 5 | 5 | Jun 23, 2026 | $3,988,000 |
| 1 GLEN EDYTH PLACE | 5 | 6 | Jun 17, 2026 | $9,990,000 |
| 116 PATRICE CRESCENT | 4 | 3 | Jun 16, 2026 | $1,199,900 |
| 287 VALERMO DRIVE | 5 | 4 | Jul 06, 2026 | $1,650,000 |
| 295 STRATHMORE BOULEVARD | 4 | 3 | Jun 25, 2026 | $2,235,000 |
| 128 NORTHLAND AVENUE | 4 | 2 | Jun 16, 2026 | $768,000 |
| 8 NORBROOK CRESCENT | 4 | 4 | Jun 25, 2026 | $899,999 |
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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0 bds • 0 ba • 0 sqft
462 NORTHCLIFFE BOULEVARD, Toronto (Oakwood Village), ON M6E3L2
0 bds • 8 ba • 0 sqft
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4 bds • 4 ba • 0 sqft
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3 bds • 3 ba • 0 sqft
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4 bds • 5 ba • 0 sqft
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4 bds • 5 ba • 0 sqft
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8 bds • 6 ba • 0 sqft
14399 KENNEDY RD, Caledon, ON L7C2H4
4 bds • 4 ba • 0 sqft
1722 CONCESSION RD 8, Adjala-Tosorontio, ON L0G1W0
5 bds • 3 ba • 0 sqft
791 ESSA RD, Barrie, ON L4N9G5
6 bds • 4 ba • sqft
185 GLENHOLME AVENUE
8 bds • 4 ba • sqft
93 NORTHCLIFFE BOULEVARD
5 bds • 4 ba • sqft
2 ROSENEATH GARDENS
5 bds • 4 ba • sqft
21 BIGGAR AVENUE
5 bds • 3 ba • sqft
114 ROSEMOUNT AVENUE
8 bds • 3 ba • sqft
46 HIGHVIEW CRESCENT
bds • 0 ba • 3180 sqft
16 ROSEMOUNT AVENUE
5 bds • 6 ba • sqft
16 ROSEMOUNT AVENUE
5 bds • 4 ba • sqft
302 WINONA DRIVE
5 bds • 4 ba • sqft
25 GLENHOLME AVENUE
5 bds • 3 ba • sqft
35 WESTMOUNT AVENUE
5 bds • 5 ba • sqft
15 HOLLAND PARK AVENUE
7 bds • 3 ba • sqft
33 ATLAS AVENUE
6 bds • 4 ba • sqft
89 ALBERTA AVENUE W
6 bds • 4 ba • sqft
89 ALBERTA AVENUE W
4 bds • 4 ba • sqft
32 REGAL ROAD
4 bds • 4 ba • sqft
32 REGAL ROAD
6 bds • 5 ba • sqft
163 ARLINGTON AVENUE
6 bds • 5 ba • sqft
163 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 $2,495,000. Highlights include 7 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 Fri July 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 2026-07-14 14:21:46. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.