106 Highland Avenue

FOR SALE
$3,629,000
106 Highland Avenue, Toronto
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
106 Highland Avenue
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4 + 1
BEDROOMS
5
BATHROOMS
1
KITCHENS
8 + 2
ROOMS
C14107036
MLSID
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Property Description
There's a certain kind of house that feels made for family life, and 106 Highland Avenue is exactly that. Set well back from the street on an exceptional 39' x 150' lot in prime North Rosedale, this handsome red-brick semi offers privacy, space and permanence. Approximately 4,000 sf (total). Completely renovated in 2015 by architect Peter Higgins, it pairs remarkable craftsmanship with thoughtful, enduring design. Step into the foyer, where heated floors & a fluted wood feature wall offer the first glimpse of the detail found throughout. The main floor features a chef's kitchen with Wolf & Miele appliances and generous island seating, opening to a large dining area. Beyond, the family room overlooks the expansive rear garden, while the elegant living room features a gas fireplace & stone mantel. Upstairs, the private primary suite offers 2 walk-in closets, its own gas fireplace, & a beautifully appointed ensuite with deep soaker tub. A 2nd spacious bedroom includes a 4-piece ensuite & walk-in closet. The 3rd floor features 2 oversized, light-filled bedrooms with custom built-ins, a shared 3-piece bath and an additional laundry room. The L/L is exceptionally functional, with high ceilings & a walkout. A heated-floor mudroom provides plenty of storage, while the expansive rec room offers space to play & work, including a dedicated office area. An additional bedroom or gym, 3-piece bath & laundry room complete the level. Outside, the rear garden is beautifully centred around an elegant fountain, creating a tranquil setting for entertaining. A long private driveway & the home's generous setback create an added sense of privacy, while a covered side storage area keeps bikes, & all the equipment of family life neatly out of the way. Walk to Summerhill Market for Saturday-morning groceries, wander the nearby ravine trails, & enjoy close proximity to Branksome Hall & Whitney Junior P.S.- all while coming home to a quiet, established North Rosedale street.
Nearby Intersections
Property Features
Park, Public Transit, Rec./Commun.Centre, School, School Bus Route, Ravine, Bar Fridge, Built-In Oven, Countertop Range, ERV/HRV, In-Law Suite, Storage, Sump Pump, Carpet Free, In-Law Capability, Private, Alarm System, Monitored, Smoke Detector, Carbon Monoxide Detectors, Natural Gas
Property Details
Address
106 Highland Avenue
Postal Code
M4W 2A6
Property Type
Semi-Detached , Semi-Detached
Lot Size
38' x 148'
Taxes
$16,458 (2026
Basement
Finished, Full, Separate Entrance
Exterior
Year Round Living, Landscaped
Heat Type
Forced Air
Heat Source
Gas
Water
Municipal
Parking Spaces
2
Garage Type
None
Listing contracted with Sotheby's International Realty Canada
497 Brunswick Avenue, Toronto
3+1
BEDS
5
BATHS
$3,495,000
FOR SALE
A True Designer's Paradise, This 3+1 Bedroom, 5 Bathroom Restored Victorian Home Is Truly A Sight To Behold! With No Detail Spared, This 3 Storey Home Has Been Extensively Renovated & Features Showpiece Finishes In Every Room. Walk In Your Front Door Off Your Spacious Covered Front Porch To A Gorgeous Foyer Featuring Crown Moulding, Wall Paneling, Classic Checkered Floor Tile & A Deep, Rich Wallpaper That Invites You Into The Space. The Fabulous Design Selections Continue In The Living Room With Bold Colour, Built-In Shelving, Bay Windows Overlooking The Porch & A Nicely Framed Wood Burning Fireplace. The Dining Room Is The Heart Of The Home With A Custom Designed Built-In Banquette & Is Perfectly Situated Below The Backdrop Of The Spectacular Spiral Staircase Which Brings A Plethora Of Depth & Character. In The Kitchen You'll Find No Expense Has Been Spared With Stunning Stone Counters & Backsplash, A Brand New Bertazzoni Range, JennAir Fridge, Freezer & Dishwasher & A Farmhouse Sink With Custom Cabinetry & Hardware To Complement The Space Which Opens To The Beautifully Appointed Family Room Featuring A Handsome Brick Fireplace & Walk-Out To The Professionally Landscaped Backyard. The Beauty Of The Home Continues Upstairs Where You'll Find Three Well-Proportioned Bedrooms, Each Of Which Includes An Ensuite Bathroom Including The Third Floor Primary Bedroom Retreat Featuring Additional Built-Ins, Fabulous Natural Light, A 4 Piece Ensuite Spa-Inspired Bathroom That Includes A Perfectly Cylindrical Shower With Rainhead Shower Head & Bench Seating Plus A Breathtaking Rooftop Deck. Not To Be Forgotten Is The Fully Finished Lower Level With Polished Concrete Floors Which Includes A Spacious Recreation Room, Additional Bedroom/Office Space & A 4 Piece Bathroom. Outside, The Fully Fenced Backyard Offers A True Outdoor Oasis With Lush Gardens & Plenty Of Space For Entertaining Plus Legal 2 Car Front Yard Parking With Freshly Laid Pavers & Landscaping.
23 Lippincott Street, Toronto
3+1
BEDS
5
BATHS
$3,196,000
FOR SALE
In a city celebrated for its eclectic design and dynamic spirit, this breathtaking residence stands alone, a showpiece of contemporary design by award-winning Ancerl Studio. From the moment you arrive, its distinctive brick facade, copper detailing, and privately fenced corner lot evoke the quiet sophistication of a New York brownstone, seamlessly set within a vibrant Toronto neighbourhood. Inside, a world of extraordinary detail unfolds, a fusion of Parisian refinement and metropolitan sophistication throughout 3,600 square feet of finished living space across four storeys. A soaring two-storey mezzanine at the center sets a dramatic tone, while custom woodwork and sculptural lines anchor the home in both scale and intimacy. Custom furnishings, sweeping sightlines, and meticulously selected materials create a narrative of quiet luxury and timeless design. At its heart, this three-storey home with three plus one bedrooms and five bathrooms elevates both daily life and entertaining. The third level is an indulgent primary suite, complete with a walk-through dressing room, five-piece spa-like ensuite, marble fireplace, and private balcony with striking CN Tower views, an ever-present reminder of the city's pulse just beyond the serenity. The lower level offers a generous recreation room with natural light, private guest bedroom, full bathroom, a second laundry, and ample storage. Outdoors, landscaped rear gardens offer a tranquil escape. A stone patio off the main level creates an ideal setting for indoor-outdoor living. The detached garage via laneway completes this urban sanctuary with seamless functionality. Every element reflects a commitment to design excellence and thoughtful craftsmanship, a singular opportunity to live beautifully in the heart of the city. The custom and curated furnishings and decor are included in the sale of the residence. *FENG SHUI certified by Master PAUL NG** *5 Wealth centers, plus powerful energy for Health & Relationships*
33 Tranby Avenue, Toronto
3
BEDS
5
BATHS
$3,425,000
FOR SALE
Welcome to 33 Tranby Avenue - a Walker's Paradise in the heart of the Annex. Steps to Yorkville's shops, restaurants and cafes, U of T, Hospital Row and two subway lines, this transitional residence delivers the highest level of finishings with a warmth that makes it a true home. 2,441 sqft of living space includes 3 bedrooms, 4.5 bathrooms designed for the way professionals and families actually live. A complete renovation by GES Contracting with interiors by Wise Nadel - a fully renovated chef's kitchen, spa-inspired bathrooms, and integrated Sonos sound In Built In Speakers throughout. The garden has been reimagined by AHS Landscaping into a private outdoor sanctuary featuring a gourmet outdoor kitchen, alfresco dining area, and fire pit lounge for cooler evenings. Professional irrigation and architectural outdoor lighting extend the living space into the trees. Lock-and-leave ease meets entertainer's dream - the rare downtown home delivering walkability, design, and outdoor living in one address. Private viewings by appointment. Great Options for parking, whether its street parking or renting near by underground.
54 Stewart Street, Toronto
5+2
BEDS
5
BATHS
$2,800,000
FOR SALE
30 story high rise assembly potential. Currently fully rented strong monthly rental income. Turnkey commercial/residential property situated directly adjacent to the future King Bathurst station on the Ontario Line (development opportunity). This 15.6 km rapid transit line, connecting Exhibition Place to the Ontario Science Centre, is set to revolutionize connectivity in Toronto. Located at 54 Stewart Street, this property is steps away from the upcoming King Bathurst station, enhancing its appeal for both commercial and residential purposes. It is extensively renovated in 2024, with over $700,000 invested in gutting the property to the studs, ensuring a maintenance-free experience for the next 20+ years. Currently houses 3 commercial tenants and 2 residential apartments. It includes a large rear addition with a private backyard patio, providing a serene outdoor retreat.
46 Bernard Avenue, Toronto
3
BEDS
4
BATHS
$3,395,000
FOR SALE
46 Bernard Ave - your dream home you never thought you could buy! Located where the Annex meets Yorkville, steps to the shops, restaurants & energy of Ave & Dav, sits a Heritage Red-Brick Victorian w/ arched windows, incredible entertaining space & serious style. A true AAA+ location where you walk out your front door & are in the middle of it all without sacrificing the charm, space & privacy of a house. And not just any house! Move-in ready. Beautifully finished. 3 bedrms. 4 bathrms. Parking. A gym. Woodburning F/Place. Did I mention the Curved Windows?! And, if that wasn't enough to swoon over, there is an absolutely magical courtyard garden oasis that feels worlds away from the city all yours to enjoy. Inside, soaring proportions & oversized principal rooms are made for city living on a grand scale - dinner for 16? No problem. Cocktails for 50? Easy. The renovated eat-in kitchen is bright, design savvy & inviting, while the primary suite delivers the full wish list: fireplace, walk-in closet & a gorgeous marble ensuite w/ heated floors. The second bedrm overlooks the backyard w/ a lovely 4 piece, & the 3rd bedrm has multiple use options: Queen Bed for family or guests; office/den; or a fantasy dressing room/custom 'Carrie Bradshaw' closet for the primary! But the real story here is the opportunity: Coveted Red Brick Victorian. Incredible space. Stunning finishes. Outdoor space. Parking. Ample storage space. Move-in ready. And, all the excitement & energy of Yorkville just steps away on one of the most coveted streets in Prime Annex. This is the rare moment when the location you've always wanted, the house you thought was out of reach and an exceptional price all meet at the same address. Come view 46 Bernard before someone else buys your home!
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