155 South Drive, Toronto, ON M4W 1S3
Toronto C09
Welcome to 155 South Drive, a landmark residence on one of Rosedale's most prestigious crescents, overlooking the gated Craigleigh Gardens & steps to the renowned Branksome Hall. Gracefully positioned on a spectacular south- and west-facing lot, this timeless estate offers nearly 8,000 sq. ft. across four impeccably designed levels, where classic architecture meets modern luxury. Designed for elegant entertaining & exceptional family living, the home features soaring 10-foot ceilings, an elevator servicing every floor, exquisite custom millwork, oversized principal rooms, 3 fireplaces, and walls of windows that fill the home with natural light. The main level showcases formal living and dining rooms, a richly panelled library, inviting family room w/custom built-ins, & a chef's kitchen with centre island, generous breakfast area, & French doors opening to beautifully landscaped gardens. The second floor is anchored by an extraordinary primary retreat with sitting room, gas fireplace, dual walk-in closets, dressing room, & a spa-inspired ensuite. Two additional oversized bedrooms each feature their own ensuite. The sun-filled third level offers a fourth bedroom, sitting room, and an exceptional wraparound sky terrace with sweeping treetop & skyline views. The walk-out lower level includes a spacious recreation/media room, fitness studio or fifth bedroom with ensuite, steam room, mudroom & direct access to a rare underground 3-car garage-an extraordinary offering in Rosedale. Professionally landscaped for complete privacy, the gardens feature expansive stone terraces, mature cedar hedging, and remote-controlled awnings, creating an idyllic outdoor retreat. Surrounded by ravine trails, premier parks & some of Toronto's finest estates, yet minutes to Yorkville, downtown, top-ranked schools & the TTC, 155 South Drive offers an unmatched combination of location, scale, elegance, and convenience. A truly rare opportunity to own one of Rosedale's most distinguished homes.
Estimate only - excludes property tax, condo fees, utilities and home insurance. Rates vary by lender and term; based on semi-annual compounding.
Walkability, transit, and bike-friendliness for 155 South Drive, Toronto, ON M4W 1S3
Provided by Walk Score®. Walk Score, Transit Score, and Bike Score are trademarks of Walk Score.
MLS# C13593480
Listed by ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTATE
On market since Jul 22, 2026
What comparable homes actually sold for in the last 12 months.
155 South Drive, Toronto, ON M4W 1S3 is listed for $8,395,000 CAD.
155 South Drive, Toronto, ON M4W 1S3 has 5 bedrooms and 7 bathrooms.
155 South Drive, Toronto, ON M4W 1S3 is a Detached.
155 South Drive, Toronto, ON M4W 1S3 is in Toronto C09, Ontario.
155 South Drive, Toronto, ON M4W 1S3 is currently for sale.
Contact Michael Mezheritsky at +1 (416) 716-4439 to arrange a private showing of 155 South Drive, Toronto, ON M4W 1S3 (MLS# C13593480). You can also send a message through the contact form on this site.
