Welcome To
1099 Ossington Ave
A Well-Composed Semi in Wychwood, With the Right Updates in Place
1099 Ossington Ave presents itself with clarity. The proportions make sense, the updates are considered, and the setting adds a layer that’s difficult to replicate.
Built in 1998—just 28 years ago—and recently renovated, this semi-detached home offers a more modern foundation than many homes in the area. The layout feels both open and intentional, with a generously scaled main floor. Living and dining areas connect seamlessly while maintaining structure, anchored by a gas fireplace that provides the space with a natural centre without interrupting the flow.
At the back of the house, the kitchen is designed for daily use. There’s ample storage and prep space, with deep green cabinetry and brand-new white Quartz countertops that provide contrast without excess. It functions as a true eat-in kitchen, giving the space a role beyond cooking. A direct walk-out leads to the deck, backyard and detached garage, creating a practical connection that simplifies everyday movement in and out of the home.
Upstairs, three bedrooms are arranged with efficiency in mind, along with a second-floor laundry placed exactly where it’s needed. Bathrooms have been updated with new vanities, toilets and mirrors, consistent with the broader set of improvements, which include new flooring throughout, updated lighting, and a full interior repaint, giving the home a fresh, cohesive feel throughout.
The finished basement extends the home in a way that’s immediately useful. A rec room provides additional living space, while an extra bedroom or office offers flexibility as needs evolve over time. There is also clear potential to create a more independent setup if priorities shift.
Outside, the backyard is intentionally low-maintenance, with new deck boards that makes it easy to use without adding upkeep. The detached garage provides secure parking for one car, with direct access from the yard.
The west-facing exposure brings consistent afternoon light, with open views toward the park and sunset. Geary Avenue Parkette sits directly across the street, and Garrison Creek Park is just a few doors down, making green space part of the immediate surroundings rather than a planned destination.
Transit access is straightforward, with the TTC at the doorstep and the Bloor subway within walking distance. Geary Ave, Bloor St W, and St. Clair West are all close by, offering a wide range of restaurants and neighbourhood spots that support day-to-day living.
1099 Ossington Ave is a house that feels resolved. The updates are complete, the layout holds up, and the location continues to make sense over time.
5 Things We Love
- A main floor that actually feels generous. The open living and dining area has real scale, not just openness—anchored by a gas fireplace that makes the space feel grounded and usable day to day.
- A kitchen that connects everything. Large enough to eat in, with generous storage and prep space on new quartz countertops, and a direct walk-out to the deck, backyard and garage—so the flow between inside and out is seamless.
- Low-maintenance outdoor space that works. The new deck and easy-care backyard make it usable without adding upkeep, with direct access to the detached garage for everyday convenience.
- Upstairs designed with practicality in mind. Second-floor laundry, right where it’s needed, keeps daily routines efficient without disrupting the flow of the home. Primary bedroom with walk-in closet.
- Flexibility built into the lower level—and the location. A finished basement with a rec room and extra bedroom or office creates immediate extra space, with the option to convert to an income suite. All set within easy reach of the subway, shops, Garrison Creek Park, groceries, and schools.
Floor Plans
3-D Walk-through
About Wychwood
Wychwood carries a sense of balance that’s increasingly hard to find—established, but still evolving in the right ways.
At 1099 Ossington Ave, that shows up immediately. Geary Avenue Parkette sits directly across the street, with Garrison Creek Park just a few doors down. Green space isn’t something you travel to—it’s built into the setting, shaping the feel of the street and the pace of the day.
From there, the neighbourhood layers outward. South toward Bloor, the energy becomes more active, with a mix of independent shops, bakeries, and long-standing local spots that give the area consistency. Christie Pits adds a larger, more social green space, often in use but never overwhelming.
To the West, Geary Avenue introduces a different dimension. Once defined by industrial buildings and auto shops, it has steadily evolved into one of the more distinctive strips in the west end—known for its mix of restaurants, small producers, and creative workspaces. The street still retains its industrial framework, but it’s now layered with independent food spots, breweries, galleries, and studios that lend it a sense of movement and originality.
What makes Geary work is that it hasn’t been over-finished. It’s active, but still feels local—somewhere you go often, not just occasionally. Whether it’s picking up fresh ingredients, stopping for a quick lunch, or spending time moving between a few familiar places, it becomes part of a regular routine.
Transit reinforces that ease. With the TTC at the doorstep and the Bloor-Danforth subway within walking distance, the rest of the city remains accessible without added complexity.
Wychwood works because of how these pieces come together—green space, independent retail, and a neighbourhood that continues to evolve while staying grounded.