106 Highland Avenue

FOR SALE
$3,795,000
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
Browsing Limit Reached
Please Register for Unlimited Access
4 + 1
BEDROOMS
5
BATHROOMS
1
KITCHENS
8 + 2
ROOMS
C13104898
MLSID
Contact Us
Property Description
Welcome to 106 Highland Ave, a gorgeous Red Brick Home w/ incredible curb appeal, impressively set back on an irreg. wide ~39' & ~150' lot ideally situated in prime North Rosedale on one of the most coveted tree-lined streets in the area. Completely renovated in 2015 by Architect Peter Higgins w/ superior quality construction thru/out & timeless design savvy finishes, this extraordinary home is "move in ready" w/ the quality of the home immediately evident as you enter the inviting entrance w/ heated floors & design savvy fluted wood wall which sets the tone for the rest of the home. The open concept main floor greets you with streaming light from front to back & the front sitting rm/great rm features an open flame gas fireplace - the perfect place to start & end your day. The heart of the main floor is the chef inspired custom kitchen w/ bespoke millwork & an oversized island which seamlessly flows into the lg dining area, ideal for everyday living & hosting parties of 12+. The cozy family rm French Doors open to the back deck o/looking the generous backyard. Bask in the generous Primary retreat on the 2nd fl w/ gas f/pl & incredible built-ins as well as 2 walk-in closets. The primary ensuite is truly an escape w/luxurious designer wallpaper, indulgent soaker tub, & twinkling chandelier floating. A 2nd generously sized bedrm also enjoys the convenience of a private ensuite & walk-in closet. 2 additional bedrms, a well-appointed bathrm, & extra laundry rm make up the spacious 3rd floor. Downstairs the lwr lvl has incredible ceiling height thru/out & heated floors in the coveted mudrm easily accessible via the walk out to the side of the house. The massive rec rm is the perfect place for kids to play, watch TV or simply hang out. The long driveway comfortably parks up to 3 cars. Enjoy your private grg offering ample storage for bikes, strollers & more. Steps to Rosedale & Chorley Parks & ravines, Branksome Hall, Whitney P.S., Summerhill Market, & the TTC.
Nearby Intersections
Property Features
None, Private, Irregular Lot
Property Details
Address
106 Highland Avenue
Postal Code
M4W 2A6
Property Type
Semi-Detached , Semi-Detached
Lot Size
38' x 148'
Taxes
$16,175 (2025
Basement
Finished
Heat Type
Forced Air
Heat Source
Gas
Water
Municipal
Parking Spaces
2
Garage Type
Attached
Listing contracted with Royal Lepage Real Estate Services Oxley Real Estate
55 Lonsdale Road, Toronto
4+1
BEDS
5
BATHS
$3,495,000
FOR SALE
Impressive 3-Storey Custom Home with Striking Stone Facade. Built in 2007 and totally renovated by the current owner with the highest of quality and attention to detail. Exceptional eye for craftsmanship this home offers the next home owner the luxury and freedom to just move in, unpack and enjoy! Offering 2759 Sq. Ft. above grade with an additional 782 sq.ft. with walk-out to breathtaking south facing deep lot and low maintenance with Astroturf. The main floor features soaring 10'1" ceilings and recently sanded and stained hardwood floors. The bespoke Hinged kitchen and all bathrooms were fully redone in 2024, showcasing premium flooring, tiles, mirrors, and fixtures-including a Victoria & Albert porcelain tub and basins in the primary ensuite. The second floor offers 9' ceilings, an oversized primary retreat with wall-to-wall built-ins with an additional walk-in closet, and a large balcony overlooking the rear garden. A second bedroom with ensuite, walk-in closet, and additional laundry complete this level. The third floor includes two more bedrooms-one generous sized bedroom with a large walk-in closet, the other with walkout to a private balcony. The walk-out lower level has 9' ceilings, a large recreation room, bedroom, second laundry area, wine closet, storage, furnace room, and access to the garage. Additional highlights include an epoxy garage floor, new garage opener, and BBQ-ready outdoor gas line. Ideally located on a quiet, coveted street near Yonge & St. Clair in the Deer Park neighbourhood -steps to shops, dining, transit, Upper Canada College, Bishop Strachan, and Brown School.
94B Admiral Road, Toronto
3+2
BEDS
5
BATHS
$3,290,000
FOR SALE
Spectacular opportunity in to live in a rare 2019 custom built and spacious semi-detached home on the most sought-after street in the heart of the Annex. Complete with a one bedroom self contained lower level apartment, this home is perfect for buyers who want to supplement the mortgage with rental income, for extended family stays, or for a private home office! This three-storey home greets you with a classic red brick exterior, and reveals a modern and sleek interior, with an impressive west-facing rear window wall that lets in an abundance of light to every level. The main floor offers elegant living and dining spaces as well as an oversized kitchen with abundant breakfast seating and a walk-out to a fully landscaped urban backyard. In the lower level, there is a family room with heated floors, a large family room with spectacular views and a full-height walk out to the back yard as well as self-contained nanny suite with a separate side entrance. The third floor has a spectacular loft, perfect for showcasing artwork, and with an oversized skylight, and large open terrace. Located steps from Yorkville, this home offers the best shops and restaurants the city has to offer right at your doorstep.
23 Lippincott Street, Toronto
3+1
BEDS
5
BATHS
$3,690,000
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 façade, 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. Every inch has been curated with intention, every surface designed to delight. 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. **FENG SHUI certified by Master PAUL NG** *5 Wealth centers, plus powerful energy for Health & Relationships*
46 Bernard Avenue, Toronto
3+1
BEDS
4
BATHS
$3,489,000
FOR SALE
Location, location! Welcome to 46 Bernard Avenue, an elegant 3+1 bedroom home in Toronto's prestigious Annex neighbourhood. Nestled on one of The Annex's most coveted streets, this Victorian home is a rare gem. This timeless residence blends historic character with modern comfort, featuring soaring ceilings, detailed moldings, bright living spaces . The main floor offers a spacious living and dining area, perfect for entertaining with a wood-burning fireplace, alongside a spacious chef's kitchen with Caesarstone Quartz Counters and backsplash (2020). Upstairs, you'll find three bright and spacious bedrooms with ample storage, including a luxurious primary retreat with a wood-burning fireplace and a lavish 5-piece ensuite with heated marble tile floors and a double vanity, fully renovated in 2023. The versatile lower level includes an additional bedroom or office-ideal for guests or remote work. Enjoy your own private back patio oasis, perfect for morning coffee or summer evenings under the stars. Located within easy reach of transit, top schools, and cultural landmarks, this home delivers both prestige and convenience. 46 Bernard Avenue is more than just a home; it's a lifestyle. Embrace the charm, character, and prominence of this magnificent Annex address. Don't miss your chance to own a truly exceptional property in one of Toronto's most desirable communities.
305 Manning Avenue, Toronto
4
BEDS
4
BATHS
$3,395,000
FOR SALE
Set in the heart of Little Italy on one of the neighbourhoods most coveted tree lined streets, 305 Manning Ave is an architecturally striking residence taken back to the foundation & completely reconstructed with intention & a focus on design, craftsmanship & modern functionality. This turnkey home offers over 3,100 sq. ft. of beautifully finished living space just steps to the city's best restaurants, cafés, shops, parks, schools & transit. The interior is defined by soaring ceiling heights, wide plank hardwood floors, custom millwork & a refined, contemporary aesthetic throughout. The main level is bright, open & designed for effortless everyday living & entertaining, anchored by a stunning chef's kitchen with sleek custom cabinetry, integrated appliances & waterfall stone island. A striking custom glass staircase & thoughtful lighting details elevate the home's architectural appeal. The 2nd floor offers 3 spacious bedrooms, each with built-in cabinetry, a well appointed five-piece bathroom & a full laundry room. Spanning the entire 3rd floor, the primary retreat feels like a boutique hotel suite with a large skylight w/ exceptional natural light, skyline views, a lg walk in closet & luxurious spa-inspired ensuite w/ heated micro-cement floors, a freestanding soaker tub & walk-in shower. The lower level, w/ ~9 ft ceilings & heated polished concrete floors has been transformed into a true wellness retreat complete w/ sauna, oversized steam shower & rec rm w/ an abundance of natural light that is perfect for a home gym. Thoughtfully designed for seamless indoor-outdoor living, the rear yard has a large composite deck, patio, hot tub & low-maintenance landscaping ideal for year-round entertaining. An oversized 2-car garage offers rare flexibility for parking, storage, a gym, studio or workspace. This one-of-a-kind home blends the quality and comfort of a luxury custom build with an unbeatable location in one of the city's most vibrant and sought-after neighbourhoods.
37 Walker Avenue, Toronto
4
BEDS
4
BATHS
$2,995,000
FOR SALE
Welcome to 37 Walker Ave, a remarkable 3-storey Victorian with picture-perfect front façade on one of Summerhill's most sought-after streets. Step past the wrought iron gate and into a professionally landscaped, low-maintenance city garden that provides distinct sophistication, privacy & calm. A front entry area opens into a formal living and dining room with soaring 10 ft ceilings and gas fireplace where dinner parties await. Walk past the powder room and into a spacious kitchen with peninsula, breakfast bar, wall-to-wall pantry, clever coat zone and desk nook. The rear of the home steps down into a relaxing family room with vaulted ceiling, wood-burning stone fireplace, and sliding glass walk-out to a very private back yard and coveted 2-car garage that qualifies for a laneway house. The 2nd floor provides a generous primary bedroom retreat with French door entry, Juliet balcony, 2 closets & ensuite with heated floors. The 2nd bedroom is large and bright. The 3rd floor features 2 additional bedrooms - the 4th would make a particularly great office - and boasts one of Toronto's best rooftop sundecks with an irrigation system, complete tranquil privacy, and superb city skyline views. The lower level benefits from its own separate walk-out at the front of the home and has nanny-suite potential. The recreation room is currently a practical storage zone with sleek wall-to-wall storage, and the front room is multi-purpose. This home is configured for easy, turnkey living...you can easily lock the front door and head up to the cottage for extended periods. 37 Walker provides the option of being move-in ready or it could shine even further with cosmetic or more extensive renovation work to the precise preferences of its next owners. All located within the Cottingham and OLPH catchment areas, close to the York School & De La Salle, and steps to shops, restaurants, private clubs, parks and the subway. In every form, this home provides incredible Summerhill lifestyle living.
1 Thurloe Avenue, Toronto
3
BEDS
4
BATHS
$2,875,000
FOR SALE
Luxury living has never been this effortless. Welcome to 1 Thurloe Avenue - one of six exclusive residences designed by renowned architect Richard Wengle, perfectly positioned in the heart of Davisville Village. Offering approximately 2,800 sq. ft. of beautifully curated living space, this south-facing home is flooded with natural light and showcases soaring ceilings, oversized windows, custom built-ins, and a dramatic rotunda family room that sets it apart from anything else on the market. A private elevator services every level, blending everyday convenience with elevated luxury. The chef's kitchen is equipped with Miele appliances, a wine fridge, integrated pantry, Caesarstone waterfall island, and seamless access to a spacious covered balcony with a gas BBQ hookup-perfect for entertaining or unwinding outdoors. Each bedroom features a private ensuite and custom closets, while the stunning primary retreat offers a custom walk-in dressing room and a spa-inspired 8-piece ensuite. Motorized blinds, abundant storage, a private locker, and secure underground parking complete the package. Professionally managed landscaping and snow removal provide a true lock-and-leave lifestyle. Just steps to cafes, restaurants, parks, shops, and the subway, this is the perfect blend of luxury, location, and low-maintenance living.
DIALOG CONTENT
Would you like to receive Similar Listing Alerts as soon as they are uploaded to MLS®?
How would you rate our website?
Would you like to rate us on Google?
Yes
273407483