Rare opportunity to own a truly unique mixed-use corner property in the heart of Cabbagetown, directly across from Riverdale Park and Riverdale Farm. This character-filled property features a functioning main floor corner commercial space currently operating as a well-established ice cream/snack bar, along with two separate and self-contained one-bedroom residential units known as the Loft and the Cottage. The property also offers two private decks and a large backyard, creating exceptional outdoor space rarely found in the city. A landmark location with incredible charm, strong visibility, and income in one of Toronto's most sought-after neighbourhoods. Steps to parks, transit, local shops, and downtown amenities. An exceptional opportunity for investors, end users, or those seeking a unique live/work property. Parking Currently Not In Use.
About this home
Photos of 161 Winchester Street
Facts and features of 161 Winchester Street
| Type | Detached |
|---|---|
| Style | 2-Storey |
| Bedrooms | 2 |
| Bathrooms | 3 |
| Size | 2500-3000 sq ft |
| Lot | 28.29 x 80 Feet |
| Parking | 2 |
| Garage | None |
| Heating | Forced Air |
| Cooling | Other |
| Basement | Partial Basement |
| Exterior | Brick, Board & Batten |
| Taxes | $14,779 (2025) |
| Days on market | 157 |
| Listing brokerage | SOTHEBY'S INTERNATIONAL REALTY CANADA |
Around this home
What’s near 161 Winchester Street
From 161 Winchester Street, the nearest station is Castle Frank station (Line 2 Bloor-Danforth), 17 minutes on foot; the nearest grocery store is Star Fruit Market, 6 minutes on foot; the nearest TDSB elementary school is Sprucecourt Junior Public School, 6 minutes on foot; and the nearest park is Riverdale Park West, 3 minutes on foot.
Transit
- Castle Frank station Line 2 Bloor-Danforth 17 min walk 5 min drive
- Broadview station Line 2 Bloor-Danforth 24 min walk 9 min drive
Groceries and pharmacies
- Rexall Pharmacy 6 min walk
- Star Fruit Market Grocery 6 min walk
- Fairway Market Variety & Grocery Grocery 6 min walk
- Cabbagetown Organics Grocery 7 min walk
- Shoppers Drug Mart Pharmacy 8 min walk
Parks
- Riverdale Park West Park 3 min walk
- Wellesley Park Park 5 min walk
- Anniversary Park Park 11 min walk
Schools
- St Martin Catholic School (StMartin) Catholic secondary · 9-12 2 min walk
- Sprucecourt Junior Public School TDSB elementary · JK-8 EQAO 2024-25: Gr 6 reading 85% · Gr 6 math 25% 6 min walk
- Winchester Junior and Senior Public School TDSB elementary · JK-8 EQAO 2024-25: Gr 6 reading 89% · Gr 6 math 57% 9 min walk
- Rosedale Heights School of the Arts TDSB secondary · 9-12 EQAO 2024-25: Gr 9 math 66% · Gr 10 literacy 95% 19 min walk 7 min drive
- Our Lady of Lourdes Catholic School Catholic elementary · JK-8 EQAO 2024-25: Gr 6 reading 80% · Gr 6 math 43% 15 min walk
- Quest Alternative School Senior TDSB middle school · 7-8 16 min walk 11 min drive
Nearest schools, not necessarily the ones that serve this address. Check with the TDSB and TCDSB school locators.
Community
- Parliament Street Library Library 12 min walk
- St. James Town Community Corner Community centre 13 min walk
- Riverdale Pool Pool or arena 19 min walk 10 min drive
Restaurants
- Park Snacks Google reviews 1 min walk
- Kinyo Google reviews 5 min walk
- Kingyo Google reviews 5 min walk
- Kibo Sushi House Google reviews 6 min walk
- F'Amelia Google reviews 7 min walk
Places: OpenStreetMap contributors, October 2026. Walking and driving times: Mapbox. Schools: EQAO 2024-25, Ontario Ministry of Education.
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161 Winchester Street
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161 Winchester Street
Listing information is deemed reliable but is not guaranteed accurate by PropTx or the Toronto Regional Real Estate Board. Data source: PropTx. Listings are refreshed from the MLS® at least daily.
The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial purpose or any other purpose.
Royal LePage Terrequity Seymour Real Estate, Brokerage. Independently owned and operated.
MLS® C13171756 Data source: PropTx Listed May 25, 2026
