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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. (id:58753)
St. Clair/Oakwood/Dufferin
Source: Public Records
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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4 bds • 3 ba • 0 sqft
195 GLEN CEDAR ROAD, Toronto C03, ON M6C3G9
3 bds • 2 ba • 0 sqft
56 CAMBERWELL ROAD, Toronto, ON M6C3E8
3 bds • 3 ba • 0 sqft
905 - 328 DUPONT STREET, Toronto, ON M5R1V9
7 bds • 4 ba • 0 sqft
188 HUMBERSIDE AVENUE, Toronto W02, ON M6P1K5
2 bds • 2 ba • 0 sqft
805 - 61 ST CLAIR AVENUE W, Toronto, ON M4V2Y8
7 bds • 4 ba • 0 sqft
415 PARKSIDE DRIVE, Toronto, ON M6R2Z7
3 bds • 3 ba • 0 sqft
205 - 77 AVENUE ROAD, Toronto, ON M5R3R8
3 bds • 3 ba • 0 sqft
412 - 6 JACKES AVENUE, Toronto C09, ON M4T0A5
4 bds • 4 ba • 0 sqft
168 LANSDOWNE AVENUE, Toronto W01, ON M6K2V9
3 bds • 3 ba • 0 sqft
5103 - 1 YORKVILLE AVENUE, Toronto C02, ON M4W1L1
6 bds • 6 ba • 0 sqft
3 CIRCLE RIDGE, Toronto W04, ON M6L2H7
4 bds • 4 ba • 0 sqft
TH05 - 101 ERSKINE AVENUE, Toronto C10, ON M4P0C5
4 bds • 4 ba • 0 sqft
811 - 250 LAWRENCE AVENUE, Toronto C04, ON M5M1B1
4 bds • 3 ba • 0 sqft
221 ROE AVENUE, Toronto, ON M5M2J3
4 bds • 4 ba • 0 sqft
6 MARQUIS AVENUE, Toronto, ON M8X1V4
8 bds • 7 ba • 0 sqft
6 ALLEGREZZA COURT, Toronto, ON M6A1T9
8 bds • 8 ba • 0 sqft
103 ALLINGHAM GARDENS, Toronto C06, ON M3H1X9
3 bds • 3 ba • 0 sqft
PH105 - 88 HARBOUR STREET, Toronto C01, ON M5J0C3
4 bds • 4 ba • 0 sqft
398 SUTHERLAND DRIVE, Toronto, ON M4G1K3
3 bds • 3 ba • 0 sqft
TH103 - 39 QUEENS QUAY E, Toronto, ON M5E0A5
bds • 0 ba • 3200 sqft
1167 ST CLAIR AVENUE W
5 bds • 3 ba • sqft
114 ROSEMOUNT AVENUE
8 bds • 3 ba • sqft
46 HIGHVIEW CRESCENT
5 bds • 4 ba • sqft
302 WINONA DRIVE
5 bds • 4 ba • sqft
313 ROBINA AVENUE
15 bds • 4 ba • sqft
9B HUMEWOOD DRIVE
8 bds • 4 ba • sqft
9A HUMEWOOD DRIVE
6 bds • 5 ba • sqft
163 WYCHWOOD AVENUE
5 bds • 6 ba • sqft
311 WYCHWOOD AVENUE
bds • 0 ba • 3162 sqft
405 - 300 GEARY AVENUE
4 bds • 5 ba • sqft
80 BUDE STREET
8 bds • 4 ba • sqft
1563 BATHURST STREET
bds • 0 ba • 3628 sqft
1923 DAVENPORT ROAD
bds • 0 ba • 2831 sqft
1602 EGLINTON AVENUE W
bds • 0 ba • 3800 sqft
1774 EGLINTON AVENUE W
bds • 0 ba • 2830 sqft
1586 EGLINTON AVENUE W
5 bds • 6 ba • sqft
613 HARVIE AVENUE
bds • 0 ba • 3175 sqft
1531 DUPONT STREET
4 bds • 6 ba • 0 sqft
1531 DUPONT STREET
Source: Realty.com
185 GLENHOLME AVENUE, Toronto (Oakwood Village), ON M6E3C5 in Toronto (Oakwood Village), ON M6E3C5 is a duplex 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.
This content last refreshed on 2026-10-02 07:31:33. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.