Attention Investors and End-Users! A high-potential property has arrived just north of the vibrant crossroads of St. Clair Avenue West and Winona Drive. Nestled in a quiet, coveted, and family-friendly neighbourhood where Humewood, Hillcrest, Oakwood Village, and Wychwood meet, this versatile detached home offers an amazing opportunity to make it your own, providing the ultimate canvas for a spectacular single-family home transformation.This bright, spacious, and updated home features 6 bedrooms, 3 bathrooms, and 3 kitchens. Complete with on site parking for two vehicles total and a garage for parking for one of those 2 vehicles andor extra storage, the property is exceptionally accessible with the TTC just steps away. Enjoy a quick commute to both St. Clair subway stations via the streetcar, with cafes, bars, restaurants, and vibrant city life all within walking distance. With a Walk Score of 95, you do not want to miss this opportunity-act now!
About this home
Photos of 229 Winona Drive
Facts and features of 229 Winona Drive
| Type | Detached |
|---|---|
| Style | 2-Storey |
| Bedrooms | 6 + 1 |
| Bathrooms | 3 |
| Size | 2000-2500 sq ft |
| Lot | 33 x 100 Feet |
| Parking | 2 |
| Garage | Detached |
| Heating | Radiant |
| Cooling | Wall Unit(s) |
| Basement | Finished with Walk-Out |
| Exterior | Brick |
| Taxes | $6,637 (2026) |
| Days on market | 51 |
| Listing brokerage | ROYAL LEPAGE SUPREME REALTY |
Rooms
18 rooms, with sizes
| Room | Level | Size | Features |
|---|---|---|---|
| Kitchen | Basement | 13′ 5″ × 10′ 1″ 4.08 × 3.08 m | w/o to yard, tile floor |
| Bathroom | Basement | 7′ 1″ × 3′ 1″ 2.17 × 0.95 m | window, tile floor |
| Kitchen | Main | 18′ 7″ × 9′ 5″ 5.67 × 2.87 m | window, east view, tile floor |
| Furnace Room | Basement | 8′ 10″ × 4′ 1″ 2.68 × 1.25 m | Concrete Floor |
| Kitchen | Second | 12′ 7″ × 12′ 1″ 3.84 × 3.69 m | window, tile floor |
| Primary Bedroom | Main | 11′ 0″ × 9′ 10″ 3.35 × 2.99 m | window, closet |
| Bedroom 4 | Second | 14′ 5″ × 10′ 8″ 4.39 × 3.26 m | window, laminate |
| Laundry | Basement | 8′ 0″ × 7′ 4″ 2.44 × 2.23 m | Concrete Floor |
| Bedroom | Basement | 13′ 2″ × 7′ 6″ 4.02 × 2.29 m | window, tile floor |
| Recreation | Basement | 18′ 7″ × 14′ 0″ 5.67 × 4.27 m | laminate, window |
| Dining Room | Main | 13′ 0″ × 10′ 8″ 3.96 × 3.26 m | window, linen closet, overlooks living |
| Bedroom 3 | Second | 14′ 5″ × 8′ 10″ 4.39 × 2.68 m | window, laminate |
| Bathroom | Main | 6′ 6″ × 4′ 1″ 1.98 × 1.25 m | Glass Block Window |
| Living Room | Main | 13′ 6″ × 12′ 1″ 4.12 × 3.69 m | window, west view, overlooks dining |
| Primary Bedroom | Second | 15′ 10″ × 10′ 0″ 4.82 × 3.05 m | window, laminate |
| Bedroom 2 | Second | 11′ 11″ × 9′ 1″ 3.63 × 2.77 m | window, laminate |
| Bathroom | Second | 7′ 9″ × 7′ 7″ 2.35 × 2.32 m | window, tile floor |
| Bedroom 2 | Main | 9′ 11″ × 9′ 0″ 3.02 × 2.74 m | window, laminate |
Around this home
What’s near 229 Winona Drive
From 229 Winona Drive, the nearest station is St Clair West station (Line 1 Yonge-University), about 1.5 km away; the nearest grocery store is St. Clair Fruit Market, about 250 m away; the nearest TDSB elementary school is McMurrich Junior Public School, about 400 m away; and the nearest park is Graham Park, about 200 m away.
Transit
- St Clair West station Line 1 Yonge-University about 1.5 km
- Ossington station Line 2 Bloor-Danforth about 2.2 km
- Dupont station Line 1 Yonge-University about 2.2 km
Groceries and pharmacies
- St. Clair Fruit Market Grocery about 250 m
- Christie Pharmacy Pharmacy about 550 m
- Moberly Natural Foods Grocery about 550 m
- Pharmacia Drugstore Pharmacy about 1000 m
- St. Clair Fruits Market Grocery about 1.0 km
Parks
- Graham Park Park about 200 m
- Humewood Park Park about 600 m
- Wychwood Barns Park Park about 750 m
Schools
- McMurrich Junior Public School TDSB elementary · JK-6 EQAO 2024-25: Gr 6 reading 96% · Gr 6 math 75% about 400 m
- Rawlinson Community School TDSB elementary · JK-8 EQAO 2024-25: Gr 6 reading 82% · Gr 6 math 39% about 600 m
- Winona Drive Senior Public School TDSB middle school · 7-8 about 550 m
- St Alphonsus Catholic School Catholic elementary · JK-8 EQAO 2024-25: Gr 6 reading 96% · Gr 6 math 50% about 200 m
- Oakwood Collegiate Institute TDSB secondary · 9-12 EQAO 2024-25: Gr 9 math 44% · Gr 10 literacy 88% about 450 m
- Msgr Fraser Orientation Centre Catholic secondary · 9-12 about 2.3 km
Nearest schools, not necessarily the ones that serve this address. Check with the TDSB and TCDSB school locators.
Community
- Davenport Library Library about 850 m
- Chabad of Midtown Community Centre Community centre about 1000 m
- Phil White Arena Pool or arena about 1.1 km
Private schools
- Girls
- The Bishop Strachan School JK to Grade 12 about 2.1 km
- Boys
- St. Michael's College School Grades 7 to 12 about 1.3 km
- Royal St. George's College Grades 3 to 12 about 2.2 km
- Upper Canada College JK to Grade 12 about 2.7 km
- Co-ed
- Arrowsmith School Ages 6 and up about 2.2 km
- The Mabin School JK to Grade 6 about 2.4 km
- De La Salle College "Oaklands" Grades 5 to 12 about 2.8 km
- Howlett Academy JK to Grade 8 about 2.9 km
Within a 40-minute walk, from our list of private schools in central Toronto (checked October 2026). Fees and admissions on each school’s site. See all private schools
Restaurants
- Mi Tierra Google reviews about 150 m
- Hungry Jack's Italian Mediterranean Grill Google reviews about 200 m
- Dragon Delight Chinese Cuisine Google reviews about 200 m
- Wings N Dip Google reviews about 200 m
- Savera Google reviews about 200 m
Places: OpenStreetMap contributors, October 2026. Straight-line distances. Schools: EQAO 2024-25, Ontario Ministry of Education.
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229 Winona Drive
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® C13757114 Data source: PropTx Listed September 8, 2026
