4-Bedroom Heritage Home in Cabbagetown, Toronto (85 Winchester St)


On a street lined with history, in a neighborhood teeming with history, in a city bursting with history, it can be hard to stand out. 85 Winchester Street simply can’t be missed.

For decades, this 1857 Centre Hall Georgian — built by Samuel G. Lyn and now one of the oldest intact homes in the Don Vale neighborhood — has garnered acclaim for its architectural and historical significance to the Old Cabbagetown district while simultaneously standing out as a quintessential Georgian design within an area renowned for its abundance of Victorian homes.

The interior of this classic manse underwent a complete rebuild from 1992 through 1994 to restore many original features while preserving its authentic brick façade. It has received the prized “Certificate of Commendation” from the Toronto Historical Board, is designated a “Historical Structure of Architectural Value” under the Ontario Heritage Act, and is a regular stop on the Cabbagetown Preservation Association’s annual walking tour.

A magnificent Japanese magnolia arbour over the wrought-iron gate and a 9-foot cedar hedge lend a mystical intrigue to this estate’s streetside charisma. Thriving elm, maple and pear trees, as well as climbing vines and a perennial garden infuse the front yard with an intoxicating aroma nearly year round. Pour a glass of chablis and step onto your expansive front veranda or second-floor walkout balcony for a relaxed overlook.

The extremely private, south-facing city garden in the rear — also well-viewed from a tranquil second-floor balcony — is even more vivacious, featuring climbing roses and hydrangea, clematis and honeysuckle.


The 4-bedroom, 2.5-bath, 2,861-square-foot main residence is a testament to the skilled and thoughtful build quality of its era, now merged with modern amenities to accommodate easy, refined living.

Entering guests are immediately charmed by the juxtaposition of yesteryear combined with a current style as they enter through the granite and terracotta tile foyer and find themselves enveloped by the winsome living room featuring a traditional wood-burning fireplace with authentic 1857 mantle, walk-out French windows still bearing original panes, crown moulding, a captivating antique wall lamp, and stunning drapery.

A large country kitchen offers excellent storage with signature maple hardwood cabinetry, quartz countertops, hand-painted ceramic tiles, wainscotting with custom moulding, and plenty of space for meal preparation. Wide southern-facing black French glass doors draw you to the serene cedar rear deck and tranquil city garden. Also on the first level, an ample library/office makes study or work time a pleasure with its sunroom feel proffered by a wall of west- and south-facing windows.

Upstairs, family and guests are smoothly accommodated with four bedrooms and two full baths. The hallway features an eye-catching wall sconce by renowned Ontario potter Harlan House and a walkout to the sweeping veranda overlooking the front gardens. The primary suite is a study in tranquility with broad north- and west-facing windows, plus dual double closets with built-in shelving. It also presents a 4-piece ensuite with a handsome custom vanity and a whirlpool bath featuring Carrera marble. Also on this level, a relaxing sunroom has windows on three sides, whitewashed ash paneled walls with floor to match, and a walkout to the south balcony. The main bathroom on this floor also features a sauna.


The home is remarkable for 9-plus-foot ceiling heights on both floors, unusual for its time, and a thoughtful combination of original styling blended to all the amenities essential to modern living.

Cabbagetown is a hamlet within a metropolis, and residents truly enjoy the best of both those worlds. Proximate to downtown yet maintaining that small-town feel. The sense of community and pride of ownership among its denizens is evident with every step along its historic, tree-canopied streets. The area’s demographics are diverse and welcoming, as incoming residents are quickly invited to add their own culture and personality to the vibe. Its eclectic personality has lured many artists, musicians and writers to call Cabbagetown home.

Art and culture play a premium here, with a plethora of galleries, vintage shops, music venues and contemporary restaurants all within a short walk. A multitude of monthly and annual social activities are designed to take advantage of the area’s opportunities, including the Cabbagetown Festival, the Riverdale Farm Fall Harvest Festival, and the Cabbagetown Short Video & Film Festival. Parliament’s shopping district offers an engaging assortment of antique shops that perfectly complement the district’s charm.

Address:85 Winchester St
Zip Code:M4X 1B1
Year Built:1857
Square Feet:2,861
Property Type:Detached House (Heritage Designation)
Lot size:42.12' x 104.61'

Location Map

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