27 Boswell Avenue

Annex, Toronto, M5R 1M5

$4,995,000

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  • 3 bedrooms
  • 4 bathrooms
  • 3 parking
  • 2000-2500 sq ft

Listed 34 days ago · MLS® C13784186

About this home

Breathtaking, fully renovated 3-bedroom, 4-bathroom showstopper on one of the best blocks in Yorkville/East Annex. Featuring garage parking and a private drive accommodating up to 3 vehicles, exceptionally rare for the neighbourhood, this property has been taken back to the studs with nothing left untouched in this contemporary renovation, which beautifully blends modern style and timeless elegance. Walk into your architecturally designed front entryway with heated floors and into a gorgeously open concept main floor plan that includes a jaw-dropping chef's kitchen with high-end appliances, including an 8-burner LaCanche gas stove, oversized island with seating, an elegant dining room and a sunken living room with a gas fireplace overlooking the south-facing rear upper terrace, gardens and lower patio. Upstairs, you'll enjoy a true primary retreat complete with a large walk-in closet and spa-inspired ensuite bath with a gorgeous, glass-enclosed steam shower with bench seating, Toto toilet, double vanity and heated floors. Two additional upstairs bedrooms are both exceptionally well-proportioned and include an additional 3-piece bath. The at-grade lower level of the property is not to be missed and offers exceptionally designed additional living space, including an enormous recreation space with another wood-burning fireplace and a fully retractable door system that opens up to the rear gardens, a built-in wet bar, a full bath, and plenty of built-in storage, including the laundry/utility room. This home is truly one to behold, with countless upgrades throughout, including white oak herringbone hardwood floors throughout and laminated security glass film at all entry points. Enjoy everything this wonderful neighbourhood has to offer with every amenity imaginable at your doorstep, including some of Toronto's finest shopping, restaurants and entertainment, plus easy access to transit and major thoroughfares.

Details

Type
Semi-Detached
Style
2-Storey
Age
51-99 years
Size
2000-2500 sq ft
Lot
25 × 95.91 ft
Basement
Finished with Walk-Out
Garage
Built-In
Kitchens
1
Property tax
$21,009 (2025)
Neighbourhood
Annex
Municipality
Toronto C02

Interior

Bedrooms
3 above ground
Bathrooms
1 × 2-piece (main), 1 × 4-piece (upper), 1 × 3-piece (upper), 1 × 3-piece (lower)
Rooms
7 above ground
Family room or den
Yes
Fireplace
Yes
Features
Carpet Free, Bar Fridge

Heating, cooling and services

Heating
Forced Air, Gas
Air conditioning
Central Air
Water and sewer
Sewer

Building and exterior

Style
2-Storey
Exterior
Brick
Roof
Asphalt Shingle
Foundation
Concrete Block
Age
51-99 years
Faces
South

Parking

Garage spaces
1
Total parking
3
Driveway and parking
Private

Lot

Size
25 × 95.91 ft

More

Possession
TBA
Nearby
Arts Centre, Cul de Sac/Dead End, Hospital, Library, Public Transit, School
Cross street
Avenue Road & Bloor Street West

Rooms

RoomLevelSizeFeatures
Primary BedroomUpper4.65 × 3.2 m (15'3" × 10'6")6 Pc Ensuite, Closet Organizers, B/I Vanity
Living RoomMain5.66 × 4.42 m (18'7" × 14'6")Sunken Room, W/O To Terrace, Gas Fireplace
KitchenMain6.48 × 5.38 m (21'3" × 17'8")Eat-in Kitchen, B/I Appliances, Casement Windows
Bedroom 2Upper3.91 × 3.15 m (12'10" × 10'4")Double Closet, Hardwood Floor, Casement Windows
LaundryLower2.72 × 1.7 m (8'11" × 5'7")Glass Block Window, Porcelain Floor, Access To Garage
Utility RoomLower4.14 × 2.54 m (13'7" × 8'4")
Bedroom 3Upper3.81 × 3 m (12'6" × 9'10")Casement Windows, 3 Pc Bath, Skylight
Dining RoomMain3.81 × 2.72 m (12'6" × 8'11")Open Concept, Pot Lights, Hardwood Floor
FoyerMain2.46 × 2.13 m (8'1" × 7')Vaulted Ceiling(s), Double Closet, Stone Floor
Family RoomLower5.41 × 4.65 m (17'9" × 15'3")Combined w/Office, W/O To Patio, Fireplace

History of this address

3 earlier listings at this address, with sold and leased prices. Create a free account or sign in to see them.

Location

Location is approximate. See nearby homes on the map

Recent sales nearby

See what similar homes within 1 km sold for in the last year. Create a free account or sign in to see them.

The neighbourhood

Getting around Very walkable

  • 🚇 St. George Subway7 min walk
  • 🚇 Bay Subway9 min walk
  • 🚆 Toronto Union Station GO3.3 km

Within a 10-minute walk: 10 grocery stores, 161 cafés and restaurants, 34 parks, 11 pharmacies. Nearest grocery: Whole Foods Market (150 m). Nearest park: Boswell Parkette (100 m).

Schools nearby

Elementary

  • Jesse Ketchum Junior and Senior Public School
    EQAO: Gr 6 reading 96%, math 71%
    6 min walk
  • Huron Street Junior Public School
    EQAO: Gr 6 reading 79%, math 59%
    7 min walk
  • Cottingham Junior Public School
    EQAO: Gr 6 reading 100%, math 100%
    14 min walk

Secondary

  • St. Joseph's College School Catholic
    EQAO: Gr 9 math 66%, literacy test 87%
    17 min walk

EQAO: share of students meeting the provincial standard (2024–25). Ontario average: Gr 6 reading 86%, math 51%; Gr 9 math 55%; literacy test 83%.

Closest schools, not school zones. Check which school serves this address with the school board before relying on it.

Who lives here postal area M5R

Owners / renters
39% / 61%
Median household income
$86,000
Average age
46
Children under 15
8%
Homes
5% detached, 54% high-rise
Commute by transit
25%
Population
26,197

Languages spoken most at home besides English: Mandarin 1.3%, Spanish 1%, Yue (Cantonese) 0.7%, Iranian Persian 0.6%.

Flood and conservation No mapped hazard

Not inside a mapped flood plain or regulated area.

Screening maps only. Ask the conservation authority for a property inquiry before relying on this.

Safety

Major crime per resident in Annex (2025): 35% above the Toronto average, down 12% from the year before.

  • Assault41% above average
  • Break and enter104% above average
  • Auto theft48% below average
  • Robberyabout average
  • Theft from vehiclesabout average
  • Shootings36% below average

Crime Severity Index for Toronto police: 60 vs 57 for Ontario (2025).

Police-reported figures for the whole neighbourhood, not this street. Rates use the area’s resident population.

Development nearby 18 active

  • 208 BLOOR ST W · 400 m
    Official Plan / Zoning By-law Amendment · Under Review · applied 2026
    Proposed redevelopment of the lands with a 36-storey Private Student Residence (112.58 metres in height, including the mechanical penthouse) with 426 dwelling…
    Application details
  • 262 ST GEORGE ST · 450 m
    Official Plan / Zoning By-law Amendment · OMB Appeal · applied 2025
    Appealed on April 24, 2026.Combined Official Plan & Zoning By-law Amendment for an 18-storey building containing 121 dwelling units, and the adaptive re-use of…
    Application details
  • 200 CUMBERLAND ST · 350 m
    Plan of Condominium · Under Review · applied 2024
    Amendment to Approved Condo Plan. Condo Exemption process
    Application details
  • 126 AVENUE RD · 200 m
    Official Plan / Zoning By-law Amendment · Council Approved · applied 2023
    Zoning By-law Amendment application to permit an 11-storey mixed-use building, containing 60 dwelling units (of which 11 are replacement rental units) and 169…
    Application details
  • 116 AVENUE RD · 150 m
    Site Plan · NOAC Issued · applied 2022
    The proposal is for a 9-storey (38 metres plus mechanical) mixed-use building with a total of 55 residential dwelling units. The gross floor area is 5,056…
    Application details
  • 141 BEDFORD RD · 300 m
    Site Plan · NOAC Issued · applied 2021
    Site Plan Approval for a 13-storey mixed-use building with 63 residential units.
    Application details

21 more within 500 m.

Rezoning, site plan, subdivision and condominium applications filed with the city.

Distances are approximate. Places © OpenStreetMap contributors. Neighbourhood figures: Statistics Canada, 2021 Census. School results: EQAO via Ontario Data Catalogue (Open Government Licence – Ontario). Neighbourhood crime: Toronto Police Service Public Safety Data Portal (Open Government Licence – Toronto Police Service). Crime Severity Index: Statistics Canada. Planning applications: City of Toronto open data.

Living here

Commute

To Union Station (downtown Toronto): 3 km. Transit times · Driving times

Noise Nothing major nearby

No highway within 500 m, rail line within 300 m, or airport flight path nearby.

Distances from the map, not noise measurements. Visit at rush hour to judge for yourself.

What can be built R

Residential (with a site-specific exception).

  • ✅ Up to 6 homes on the lot (multiplex): a sixplex ward
  • ✅ Garden suite in the backyard
  • ✅ Laneway suite, if the lot backs onto a lane

From Toronto’s Zoning By-law 569-2013 map. Lot size, setbacks and trees decide what actually fits; check with a planner before you buy.

Full lot check · Run the numbers

Heritage Protected

This address is on Toronto’s Heritage Register: Heritage Conservation District (Part V). Changes to the outside (and sometimes inside) usually need a heritage permit, and demolition is restricted.

Heritage Register entry

Building permits

  • Multiple Projects · 2021 · Inspection
    Interior alteration to existing single family semi detached brick dwelling. Replace rear deck w/ minor alterations to existing exterior…

1 permit on this block of the street in the last 2 years.

Permits filed with the City of Toronto. A permit doesn’t mean the work passed final inspection.

Trees

63 City street trees within 100 m. That’s more than the Toronto average of 42.

Trees on City boulevards only, not private yards or parks.

Internet High-speed

50/10 Mbps or faster available here by cable, fibre or DSL (the federal high-speed target).

From the federal broadband map. Check exact speeds and providers for the address.

Short-term rentals

Only in your principal residence (where you live). The entire home can be rented up to 180 nights a year; renting up to 3 bedrooms while you live there has no limit. Hosts register with the City and collect the 6% accommodation tax.

City rules

Zoning, heritage, building permits and street trees: City of Toronto open data (Open Government Licence – Toronto). Roads, rail, airports and planned stations © OpenStreetMap contributors. Internet: Innovation, Science and Economic Development Canada, National Broadband Data.

Listed by CHESTNUT PARK REAL ESTATE LIMITED.

Listing information provided by PropTx Innovations Inc. and TRREB; deemed reliable but not guaranteed accurate by PropTx.

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