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106 Highland Avenue — Semi-Detached

For Sale

Toronto, ON M4W 2A6

5 Bed · 5 Bath · Semi-Detached

MLS #C13104898

$3,795,000

Listed Price

About This Property

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.

Property Details

Bedrooms

5

Bathrooms

5

Square Feet

2500-3000 sqft

Property Type

Semi-Detached

Style2 1/2 Storey
Approx. Age100+ years
Lot Size38 148 ft
Frontage38.2 ft
Depth148.5 ft
GarageAttached
BasementFinished
CoolingCentral Air
HeatingForced Air
FireplaceYes
Parking Spaces2
Listed OnMay 7, 2026
MLS Size2500-3000
Property Tax$16,175/year

Rooms

NameSize (m)Size (ft)Features
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Living Room(Main)5.08 x 4.1416.7 x 13.6-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Dining Room(Main)4.78 x 3.7815.7 x 12.4-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Kitchen(Main)4.8 x 2.7415.7 x 9.0-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Family Room(Main)3.45 x 3.2511.3 x 10.7-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Primary Bedroom(Second)4.04 x 3.6613.3 x 12.0-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 2(Second)5.61 x 3.2818.4 x 10.8-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 3(Third)5.23 x 3.8617.2 x 12.7-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Bedroom 4(Third)4.98 x 3.3516.3 x 11.0-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Recreation(Basement)5.11 x 4.7816.8 x 15.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-
Bedroom(Basement)4.27 x 2.9514.0 x 9.7-

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Home Features

Property TypeSemi-Detached
Style2 1/2 Storey
Approx. Age100+ years
Lot Size38 × 148 ft
Frontage38.2 ft
Depth148.5 ft
GarageAttached
BasementFinished
CoolingCentral Air
FireplaceYes

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About 106 Highland Avenue, Toronto, ON M4W 2A6

106 Highland Avenue, Toronto, ON M4W 2A6 is a 5-bedroom, 5-bathroom 2 1/2 storey semi-detached with approximately 2500-3000 square feet of living space, situated on a 38 148 foot lot. This property is currently for sale at $3,795,000. The home features a attached garage and a finished basement, built approximately 100+ years ago.

Rosedale-Moore Park Neighbourhood

This home is located in Rosedale-Moore Park, part of Toronto C09 in the Toronto area. Explore more homes for sale and recently sold properties in this neighbourhood.

Whether you are looking to buy, sell, or lease in Rosedale-Moore Park, our team of experienced real estate professionals can help you navigate the market and find the perfect home. Contact us today for a free consultation.

106 Highland Avenue, Toronto, ON M4W 2A6

106 Highland Avenue, Toronto, ON M4W 2A6 for sale,5 bedroom semi-detached Rosedale-Moore Park,Toronto C09 homes for sale,Toronto real estate,2 1/2 Storey homes, semi-detached for sale