Winter Wind Cottage sits on an extra-wide waterfront lot on Hedge Road, one of Jacksons Point's most sought-after streets. Private and green, the property offers flat, usable table land that opens the door to sitting areas, family gatherings, and room for kids to play. A newly built stairway winds down through the hedges to two tiers of dockside deck at the water's edge, where the rock shelf gives way to sand - the kind of entry that makes a lake worth owning. Inside, the cottage unfolds around that same water. The kitchen, lit by a skylight beneath a cathedral ceiling, opens directly into a dining room walled in glass toward Lake Simcoe, with the great room set right alongside - beamed ceilings, a floor-to-ceiling fireplace, and windows that turn the lake into a permanent backdrop. Four bedrooms and three bathrooms give the layout real breathing room, and because the cottage runs wide rather than deep, that water view follows you through nearly every room. Live in it while you plan what comes next, or start reimagining now - this lot supports either path, and gives you the luxury of time to decide. This is Jacksons Point, a village that has held onto its identity as Toronto's original cottage country: a short walk to the Briars, an easy stroll for ice cream in the village, and a community with roots that go back generations. Lake Simcoe anchors it all - a four-season lake for boating and swimming through summer, skating and ice fishing once it freezes. Winter Wind Cottage is a chance to own a piece of it.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
Bungalow
Total Approx Floor Area:
1500-2000
Lot Depth:
122'9"37.4 m
Lot Frontage:
138'42.1 m
Lot Shape:
Irregular
Direction Faces:
North
Bedrooms:
4
Bathrooms:
3.0
Water supply:
Well
Kitchens:
1
Bedrooms Above Grade:
4
Kitchens Above Grade:
1
Rooms Above Grade:
9
Heating type:
Baseboard
Heating Fuel:
Oil
Fireplaces:
1
Foundation:
Poured Concrete
Roof:
Asphalt Shingle
Basement:
Crawl Space
Fireplace Features:
Family Room, Wood
Fireplace/Stove:
Yes
Alternative Power:
None
Garage:
None
Garage Spaces:
0.0
Parking Features:
Private
Parking Spaces:
4
Total Parking Spaces:
4.0
Rural services:
Cable Available, Electricity Connected, Garbage Pickup, Recycling Pickup, Telephone Available, Natural Gas On Road, Internet High Speed
Family Room:
No
Lot Irregularities:
138.00 Lakeside and 122.78 East Side.
Pool:
None
Link:
No
HST Applicable To Sale Price:
Included In
Assessment Year:
2025
Taxes:
$8,692 /
2026
Assessment:
$- /
2025
York
Georgina
Sutton & Jackson's Point
Beach, Clear View, Golf, Lake Access, Marina, Waterfront
Primary Bedroom - Main Floor, Sump Pump
Lighting, Privacy
Right Of Way
None
Existing stove with hood range, French door refrigerator, dishwasher and microwave . Attached lighting fixtures and window coverings.
Wood
132'40.15 m
Stairs to Waterfront, Breakwater
Direct
Rocky, Sandy, Clean
None
South
Clear, Lake, Skyline, Trees/Woods, Water
Direct, Unobstructive
Municipal Road, Paved Road, Year Round Municipal Road
Data was last updated July 17, 2026 at 04:15 PM (UTC)
Area Statistics
Listings on market:
96
Avg list price:
$893,916
Min list price:
$399,000
Max list price:
$4,500,000
Avg days on market:
35
Min days on market:
1
Max days on market:
260
These statistics are generated based on the current listing's property type
and located in
Sutton & Jackson's Point. Average values are
derived using median calculations. This data is not produced by
the MLS® system.
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website.
The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.