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$8,395,000
5 Beds ⋅ 7 Baths ⋅ C13593480 MLS
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.

155 South Drive, Toronto
$3,699,000
3 Beds ⋅ 3 Baths ⋅ C13570754 MLS
Framed by the endless green canopy of the Rosedale Ravine, this residence commands one of the most coveted vantage points in Toronto. Spanning over 3,000 Sq.ft., it is designed with both elegance and ease in mind. Floor-to-ceiling windows flood the space with natural light, framing uninterrupted majestic views of the Ravine and beyond, while travertine and custom wood-accent walls add warmth and timeless sophistication. The thoughtful split-level layout strikes the perfect balance between connection and privacy, featuring expansive principal rooms, a cozy family room with fireplace, and a chefs kitchen appointed with a Wolf Gas Cooktop, StainlessSteel Appliances, Wine and Beverage Fridges, and a splendid Centre Island with integrated storage making meal prep effortless. A custom-designed servery enhances both everyday living and grand entertaining, while the surround-sound system and independent temperature control zones elevate comfort and convenience. New Hardwood Flooring throughout main living areas. The primary suite is a private retreat, with a sitting area and fireplace, a resort-worthy five-piece ensuite with jacuzzi, a walk-in closet with custom organizers, and a walkout to a private balcony. Two Parking Spaces with EV chargers, all-inclusive Maintenance Fees, and a walkable location in the heart of Toronto mere steps to Yorkville complete this exceptional offering. Residents also enjoy access to the indoor pool, newly renovated guest suites, and an impeccable 24/7 security services.

300 Bloor Street E Unit 2701, Toronto
$509,000
1 Beds ⋅ 1 Baths ⋅ C13554686 MLS ⋅ The Rosedale Ravine Residences BLDG.
Rarely available in a sought-after Rosedale luxury boutique building, this beautifully appointed suite offers an exceptional blend of space, style and convenience. The king-sized primary bedroom features a built-in closet, while the open-concept living and dining area is enhanced by upgraded hardwood flooring and a charming Juliet balcony. The spacious kitchen is designed for both everyday living and entertaining, with a peninsula island and breakfast bar, full-sized stainless steel appliances and granite countertops.Enjoy the comfort of a well-managed building with beautifully renovated hallways and common areas, ideally located just steps from the subway, shops, restaurants, parks and scenic trails. Minutes to Yorkville, University of Toronto and Toronto's Financial District. Heat, hydro and water are all included in the monthly maintenance fees-an increasingly rare benefit.EXTRAS: Hotel-inspired amenities include a 24-hour concierge, visitor parking, fitness centre, sauna, guest suite and party room. Locker included.

388 Bloor Street E Unit 507, Toronto
$7,900,000
5 Beds ⋅ 6 Baths ⋅ C13123366 MLS
A truly exceptional residence in prestigious Rosedale, this custom-built home is a rare expression of architectural significance, craftsmanship, and timeless design. Created by acclaimed architect Robert Le Blond, recipient of the Governor General's Award in Architecture, the residence reflects remarkable artistry and enduring sophistication. Near Chorley Park, the home offers over 5,000 square feet of beautifully curated living space, clad in rare Manitoba Tyndall stone known for its distinctive fossilized beauty. Inspired by French Art Deco design, every detail has been thoughtfully considered, from extraordinary ironwork imported from Spain to the rich natural materials and elegant proportions throughout. The interiors are both grand and inviting, anchored by a dramatic 17-foot living room with statement lighting, custom millwork, and warm mahogany-stained Jatoba wood finishes. Formal principal rooms are designed for elegant entertaining, while the chef's kitchen, breakfast area, and adjoining family room create a seamless flow for everyday living. Floor-to-ceiling windows open onto a beautifully landscaped garden retreat, offering privacy and tranquility, while heated outdoor spaces, including the front porch and rear veranda, extend comfort through every season. With five bedrooms, two private offices, six bathrooms, five fireplaces, and a wraparound balcony, the home offers exceptional scale for family living. A detached heated garage with skylight, wet bar, shower, and custom storage adds incredible flexibility for a studio, workshop, or private retreat. A gated drive and meticulous design complete this extraordinary offering, where architecture and livability exist in perfect balance.

177 Roxborough Drive, Toronto
$4,850,000
5 Beds ⋅ 6 Baths ⋅ C13002612 MLS
Luxury meets location is South Rosedale! Nestled in one of Torontos most prestigious neighbourhoods, this South Rosedale gem is part of a rare, exclusive enclave developed approximately 25 years ago. A true prize, this home blends timeless craftsmanship with refined elegance, custom mouldings vaulted ceilings, and top-tier construction speak to its luxurious pedigree.Enjoy unparalleled convenience: you're just a 5-minute walk to the Summerhill subway, fine dining, boutique shopping, and more. This is a rare opportunity to own a distinguished home in a location where luxury truly meets lifestyle.

45 Mathersfield Drive, Toronto
$4,199,000
5 Beds ⋅ 5 Baths ⋅ C13001090 MLS
40 Summerhill Gardens, an exceptional offering in the prestigious Summerhill & Yonge neighbourhood - where refined design meets the serenity of ravine living. This architecturally striking residence offers approximately 4,000 square feet above grade, thoughtfully designed to deliver both elegance and functionality across every level. The main floor unfolds with seamless sophistication, featuring expansive principal rooms ideal for both everyday living and upscale entertaining. A warm gas fireplace anchors the living space, while the open-concept layout flows effortlessly through the living, dining, and family areas. The chef-inspired kitchen is appointed with premium stainless steel appliances, sleek finishes, and ample workspace, perfectly suited for hosting or quiet family meals. Designed with privacy and versatility in mind, the home's 3+2 bedroom, 5 bathroom layout spans multiple levels, offering well-defined spaces for relaxation, work, and recreation. A standout home office, framed by a picturesque ravine backdrop, creates an inspiring work-from-home environment. The primary suite is a true retreat, complete with a spa-like 6-piece ensuite and generous proportions. Additional features include a fully customized home gym, a stylish and functional mudroom, and beautifully appointed secondary bedrooms. Outdoors, a spacious deck provides a tranquil setting for entertaining or unwinding, surrounded by lush ravine views. With parking for three vehicles, including a private garage, and just steps to transit, upscale shops, and acclaimed dining, this residence offers a rare blend of urban convenience and natural beauty-an extraordinary opportunity in one of Toronto's most sought-after enclaves.

40 Summerhill Gardens, Toronto