Welcome to the Regency, an exclusive residence in one of Toronto's most prestigious neighbourhoods, directly across from the iconic Four Seasons Hotel. Surrounded by luxury brand boutiques, Michelin-awarded and -mentioned restaurants, charming cafes and cultural landmarks like the Royal Ontario Museum, this home places you in the centre of refined city living. This expansive suite offers the comfort of a true family home: three private terraces, a grand primary bedroom suite, a generous second bedroom suite, three full bathrooms, a versatile den that can easily convert to a third bedroom and an open-concept living/dining area along which spans a huge terrace. Enjoy the ease and security of two underground parking spaces, the warmth of a dedicated, service-oriented concierge team and the convenience of a well-managed condominium. Just steps from amenities and public transportation, this residence combines the best of luxurious comfort and urban accessibility. City living rarely feels this personal. Come experience this stunning home - you won't want to leave...More details
Listed by RE/MAX Escarpment Realty Inc., Brokerage
This grand dame home sits on the iconic Madison Avenue in the prime Annex. Circa 1905, 135 Madison Avenue is just under 4,000 square feet above grade and filled with original character including 4 fireplaces, original trim, wainscotting, crown moulding, and stained glass windows. The well proportioned house features 9.5" ceilings on the main floor, a large formal living and dining room as well as an oversized kitchen with a butlers pantry, and a beautiful main floor family room that leads out to the lush garden. On the second floor you will find a generous primary bedroom with a sitting area, fireplace and a three piece ensuite. There are an additional 2 large bedrooms on the second floor as well as 2 full washrooms, a dedicated laundry room, and a large sunny deck. The third floor would make a fabulous primary suite and currently includes a large living room, kitchen, two additional bedrooms and a large deck with skyline and treetop views. The basement is partially finished with 7 foot ceilings and features a separate entrance. This home has been used as single family for many years but has potential for many layouts and possibilities. Two car private drive parking and garden suite potential. The Annex speaks for its self with easy TTC, fabulous shops, restaurants, parks and schools. Floor plans attached to listing.More details
A great opportunity for someone to create a perfect city home. This 125 year-old Edwardian residence on sunny South exposure is waiting for a creative person to reimagine the interior. Probate is just completed. Owners are offering very flexible closing date early or later - whatever suits your needs. The property is now vacant and very easy to show. Great project for builders or architects who can create a very attractive home for professionals. Two car parking off the rear lane way is currently rented. Please park on the street for showings and open houses. Chicora Avenue is a tree line street of Century Edwardian homes. Built in 1900 and has been occupied by the current family since 1952.The property is listed with the city of Toronto as a duplex, but does not have two separate apartments currently. It is a handsome 2.75 floors, red brick semi detached home. Currently three cars are parked at the rear of the property. Parking is accessed from laneway off Bedford Road. Great opportunity to renovate to suit.More details
Bright, upgraded, and spacious duplex in the prime central neighbourhood of Tarragon Village/Casa Loma. Three self-contained units: two bedroom suite on the main level, another two bedroom unit on the upper level, and one bedroom unit in the lower level. All of the units have been recently renovated, including new kitchens and bathrooms. Each unit with in-suite laundry. The suites are ready to be rented out as a prime opportunity for excellent income. Great area for steady rental income, in walking distance to George Brown College and University of Toronto, and close to TTC. Two car private parking in driveway. A great outdoor space that is fenced in and low maintenance. This is an unbeatable opportunity to own a well maintained, updated property with great rental income.More details
Welcome to one of the most sophisticated homes in Rosedale. This immaculate residence offers a lifestyle of gracious living with the charm of a Mayfair Townhome. The soaring ceilings, architectural details, and high-quality finishes and design come together to create a residence of great distinction. This condo TH is located in one of the grand mansions of Rosedale, just two blocks from Yonge St., with 4000 sq ft of glorious living space on all three levels. The grand staircase sets the tone as you enter this magnificent suite. The enormous great room offers the perfect environment for delicious dining and fabulous conversation by the heavenly fireplace. The original panelled library will become the center of family life with its magnificent fireplace and sublime bay window. The gourmet eat-in kitchen will be the perfect backdrop for joyous gatherings. The second floor boasts three fabulous bedrooms with en-suite bathrooms and a wonderful walkout to the most picturesque terrace in the trees. The lower level boasts a walk-in wine cellar and an additional bedroom with fireplace, full bathroom, great storage, and practical amenities to enjoy.More details
287 Macpherson Avenue is a rare opportunity to acquire a freestanding brick and beam office building perfect for users and/or investors in one of Toronto's most coveted neighbourhoods. Strategically located in Midtown Toronto's prestigious Casa Loma area, steps from the Annex and Summerhill communities, this character-rich property offers exceptional flexibility for investors and users with significant long-term upside. Located just an eight-minute walk to Dupont Station, Tenants can enjoy seamless access to public transit while surrounded by the city's vibrant cultural, dining and shopping districts. The property represents a rare chance to own or reposition a distinctive asset in a highly desirable urban enclave.More details
Modern city living in one of Toronto's most connected neighbourhoods. This sleek New Yorks tyle residence offers the best of urban living with a fresh, contemporary edge. Designed with both style and practicality in mind, the home features three spacious bedrooms and two beautifully renovated bathrooms, each finished with clean lines and high-quality materials. The open-concept layout centers around a chefs kitchen that's as functional as it is impressive. Outfitted with premium appliances, custom cabinetry, and expansive countertops, it's a space built for cooking, gathering, and entertaining with ease. Natural light pours through large windows, highlighting the high ceilings and creating a bright, airy feel throughout the main living areas. The primary suite offers a peaceful retreat, complete with its own ensuite bathroom, in-suite laundry, and a Juliette balcony. Two additional bedrooms are generously sized and share access to a well-designed second bathroom, making the home ideal for families, guests, or flexible work-from-home setups. Outdoor living is a highlight, with a private terrace that offers a quiet escape from the city, whether you're enjoying your morning coffee or hosting friends in the evening. Practicality meets luxury with two rare underground parking spots and an extraordinarily large private locker, amenities few homes in this sought-after neighbourhood can offer. Just steps from St. Clair West Station, this home offers effortless connectivity across the city. Enjoy the charm of local cafés, boutique shopping, and cultural attractions, all while being part of a vibrant, close-knit community. Wychwood Barns serves as a dynamic neighbourhood hub, and families will appreciate the top-rated Hillcrest Community School. This is a home that delivers on every level. Smart layout, quality finishes, unbeatable location.More details
Welcome to Suite 329 at 40 Oaklands Ave, a fully reimagined 2-storey condo in The Oaklands, an award-winning boutique building by architect Macy DuBois. This 2+den, 3-bath home combines striking design with the ultimate Summerhill address. Close Proximity to Grocery Stores, LCBO, transit, and Yonge Sts boutiques and dining, with Yorkville, Bloor St, and the city's best parks minutes away. Inside, wide-plank white oak floors, expansive windows, and a porcelain tile fireplace set the tone. The custom kitchen boasts sleek cabinetry, quartz counters, porcelain slab backsplash, and premium integrated appliances. Two bedrooms with private balconies, a versatile den, and laundry. The primary suite features a boutique-style closet and spa-like 5pc ensuite with freestanding tub, glass shower, and double vanity. Cottingham PS catchment and steps to De La Salle College. Architecture, lifestyle, and convenience converge in this rare urban retreat.More details
Welcome to Rosedale Terraces! Experience boutique style living at its finest in the heart of Summerhill! This pedestrian-friendly neighborhood and has no shortage of shops, restaurants, parks and trails, two subway stations and every amenity you could ask for! Be the first to enjoy a soon to come pedestrian-focused laneway at Scrivener Square with curated retail and public space. Enjoy this one bedroom unit that has been upgraded top to bottom: hardwood floors, Corian counters,Jenn-Air s/s appl, Erth Coverings stone accent walls, and enjoy beautiful warm days at your very own private terrace overlooking the courtyard! A True Gem!More details
Welcome to luxurious living at Rosedale's prestigious Thornwood. Step into this Stunning one bedroom light-filled apartment with high-end finishes throughout. Enjoy a bright, open layout with chevron white oak floors and floor-to-ceiling windows. Step out onto your private terrace where you can enjoy serene courtyard views. Kitchen has custom high-end cabinetry & Bosch appliances. Relax at the kitchen island or by the cozy fire. Conveniently located just steps from the LCBO, Gourmet Food Shops, and restaurants. One car parking and a large locker with custom California closets built-ins. Thornwood's luxurious amenities include a 24-hour concierge, valet parking, a state-of-the-art fitness room, a spacious party room with a large terrace, guest suites, and visitor parking. Easy access to Summerhill and Rosedale subway stations, parks, Don Valley trails, and Bloor/Yorkville. This location offers unbeatable walkability and lifestyle. Sophisticated city living at its finest!More details
Welcome to 68 Mathersfield Ave - an elegant semi-detached hm in the heart of South Rosedale, one of Toronto's most prestigious & picturesque neighbourhoods. Offered for the first time in 25 years, this rare new build features over 4,600 square ft over 2 floors plus an amazing lower level & is while located in a heritage district it provides all the bells & whistles of a modern hm on a quiet cul-de-sac for ultimate privacy. The main floor welcomes you with a generous front hall & lg closet, a private office, & a spacious formal living/dining rm w/ 9' ceilings. A few steps down, the heart of the home unfolds a spectacular oversized kitchen w/ a large island & breakfast area, flowing into a stunning family room w/ 11' ceilings overlooking the green long views of the backyard & beyond. Bathed in natural light & featuring gleaming hardwood floors thru/out, you can cozy up to 1 of 2 gas fireplaces either in the living rm or family rm. Upstairs, the spacious primary suite offers a peaceful retreat, complete w/ a unique turret ceiling & bay window overlooking treetops. Two additional bedrooms each feature en-suite baths and large closets, providing luxurious comfort for family or guests. A skylight above the curved staircase brings light cascading through every level of the home. The lower level is truly exceptional w/ 8' ceilings & multiple windows that make the space an extension of the home. This level includes a large recreation room, exercise room, a fourth bedroom, and abundant storage perfect for a growing family or organization. Outside, enjoy a rare 2-car garage, a highly sought-after feature in this historic neighbourhood. Located just steps to highly rated Rosedale Jr. Public School, Mathersfield Park, the TTC, and Toronto's extensive ravine trail system, this home offers the ultimate in convenience, lifestyle, and natural beauty. A truly rare and coveted offering in the centre of the city.More details
Listed by ROYAL LEPAGE REAL ESTATE SERVICES OXLEY REAL ESTATE
Extraordinary South Hill Landmark Residence. A rare offering of architectural brilliance and historic significance, this storybook red-brick estate was originally built in 1908 and is attributed as the early residence of Lawrence Harris, celebrated founder of Canadas famed Group of Seven. Painstakingly rebuilt w/a full-scale reconstruction and rear addition in 2018, followed by an elevated design renovation in 2020 by Sherwood Homes and Connie Braemer Design, this property masterfully blends heritage charm w/modern luxury. Behind its romantic façade lies a sophisticated contemporary interior, curated with exceptional attention to detail. The dramatic foyer showcases a Nero Marquina and Oriental White marble checkered floor beneath a mirrored bronze ceiling, with Macassar ebony archways and custom aged-metal French doors. The living room offers a bespoke black metal fireplace with nero assoluto stone and custom window seating, while the jewel-like powder room is wrapped in Phillip Jeffries cork wallpaper. The chefs kitchen by Cando Woodworking features rift-cut ebony-stained oak cabinetry w/brass detailing, a custom metal hood, Belvedere quartzite counters, 10 sliding glass doors that connect seamlessly to the outdoors. Ebony-stained mahogany millwork and a sleek black metal mantel enrich the adjoining family room. The primary suite is a private retreat w/custom Sapele mahogany furnishings, a Noir St. Laurent marble fireplace, and a boutique-style walk-in closet. The ensuite is clad in Noir St. Laurent marble with a dramatic backlit feature wall, custom vanity, and integrated sinks. Outdoors, a spectacular acrylic and stainless-steel pool by Elite Pools anchors the private garden oasis, complemented by extensive cedar decking, multiple terraces, and retractable awnings. A heated driveway with custom pavers and illuminated walkway complete this world-class residence. This is more than a home, it is a South Hill landmark, where history, design, and luxury converge.More details
Data was last updated September 9, 2025 at 02:15 AM (UTC)
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website.
The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.