59 Chipstead Road, Toronto, ON M3B 3E8
A Grand Dame Ready for Her Next Chapter. This is an opportunity to apply your personal vision. Sitting tall and proud on a 65' x 120' corner lot, this Tudor-inspired residence with a storybook turret marks the entrance to the sought-after Banbury/Denlow neighbourhood. With over 4,800 sq. ft. of living space, including the lower level, and an arched, stone-framed entry, it is one of only a few homes of its kind in Banbury. A grand marble foyer with a circular staircase sets the tone. The living room has a large picture window, hardwood floors, and a fireplace. The formal dining area has easy access to the large kitchen with built-in appliances, island, tons of storage, and counter space. Both the kitchen and family room open to the sun-filled addition with two walkouts to the garden. Two-piece powder room and a laundry room with direct access to the double garage is an added bonus. Four large bedrooms, including a spacious primary with ensuite and walk-in closet. A dedicated nook is ideal for an office or play area. The lower level offers a large recreation room with built-in bar, a three-piece bathroom, and tons of storage. Potential for a +1. On the market for the first time in over 50 years. Improvements include: Sun-filled main floor addition with two walkouts to garden (1991) New hardwood on the second level (2020) Renovated 5-piece bath with jacuzzi (mid 90's) Windows replaced throughout (dining room excepted) (90's) Waterproofing with new weeping tile (2024) New boiler heating system and tankless water heater (2018) New roof (2011). Amazing family community, known for top-rated private schools (Crescent, Toronto French School, Bayview Glen). Public schools (Denlow, Windfields, York Mills Collegiate). Come see the possibilities this home can offer.
Foyer
Wainscoting, Marble Floor, Double Closet
4.42 x 4.01 m
Main
Living Room
Hardwood Floor, Fireplace, Crown Moulding
6.4 x 3.96 m
Main
Dining Room
Hardwood Floor, Swing Doors, Window
3.66 x 5.57 m
Main
Kitchen
French Doors, B/I Appliances, Centre Island
3.96 x 4.88 m
Main
Breakfast
Tile Floor, Breakfast Bar, Overlooks Backyard
3.56 x 8.15 m
Main
Family Room
Hardwood Floor, B/I Bookcase, Fireplace
5.18 x 3.66 m
Main
Primary Bedroom
5 Pc Ensuite, Walk-In Closet(s), Broadloom
5.36 x 3.96 m
Second
Bedroom 2
Hardwood Floor, Window, Double Closet
3.66 x 4.5 m
Second
Bedroom 3
Hardwood Floor, Window, Double Closet
3.56 x 3.96 m
Second
Bedroom 4
Hardwood Floor, Window, Closet
4.01 x 3.96 m
Second
Office
Hardwood Floor, Window, Circular Room
2.36 x 3.86 m
Second
Recreation
B/I Bar, Vinyl Floor, 3 Pc Bath
4.75 x 13.26 m
Lower
Other
Separate Room
5.03 x 4.93 m
Lower
Interior features
Built-In Oven, Countertop Range
Basement
Finished
Bathrooms
1 × 2-piece — Flat, 1 × 4-piece — Second, 1 × 3-piece — Lower, 1 × 5-piece — Second
Fireplace
Yes
Family room
Yes
Kitchens
1
Rooms (above / below grade)
9 above, 1 below
Architectural style
2-Storey
Construction materials
Brick
Foundation
Concrete
Roof
Shingles
Direction faces
East
Garage type
Attached
Garage spaces
2
Total parking spaces
6
Driveway parking
4
Parking features
Private
Lot size
65 x 120 ft
Cross street
York Mills and Leslie
Directions
East of Bayview south of York Mills
Neighbourhood
Banbury-Don Mills
Heating
Baseboard — Gas
Cooling
Central Air
Water
Sewer
Sewer
List price
$1,998,000
Original list price
Annual taxes
$11,832
Tax year
2026
Legal description
PARCEL 403 1 , SECTION M1453 LOT 403. PLAN 66M1453 TWP OF YORK/NORTH YORK CITY OF TORONTO
Inclusions
Exclusions
MLS #
C14030702
Status
Active
Transaction type
For Sale
Property type
Residential Freehold
Property sub type
Detached
Days on market
List date
Possession
Immediate
Occupancy
Vacant
Listing brokerage
CHESTNUT PARK REAL ESTATE LIMITED
$2,365,000
Median list price
40
Active listings
New in last 30 days
Median days on market
Estimated monthly payment
$9,578
Educational estimate only — actual payment depends on your lender, credit, and insurance requirements.
Sign in to see recent sold prices for homes like this one nearby.

$1,999,000
40 Tottenham Road, Toronto, ON M3C 2J4
TAIHOME REALTY INC.

$1,999,800
39 Apollo Drive, Toronto, ON M3B 2G9
CENTURY 21 PERCY FULTON LTD.

$1,999,800
55 Hemford Crescent, Toronto, ON M3B 2S4
ROYAL LEPAGE SIGNATURE REALTY

$1,990,000
11 Hollyhock Court, Toronto, ON M3B 0B4
RE/MAX REALTRON WENDY ZHENG REALTY

$1,900,000
19 Brookwood Court, Toronto, ON M3C 1C1
RE/MAX HALLMARK REALTY LTD.

$1,898,000
91 Larkfield Drive, Toronto, ON M3B 2H6
RE/MAX HALLMARK REALTY LTD.