38 Whippoorwill Road, Lion's Head

Lion's Head

38 Whippoorwill Road
38 Whippoorwill Road
38 Whippoorwill Road
+29
3
 bed
1
 bath
4
 parking
700 - 1100
 sqft
Detached
$499,900
For Sale
6 hours
 on site
$499,900
Click to open the pre-gallery to get the direction
Size
-
Lot size
16510 sqft
Street frontage
-
Possession
Immediate
Price per sqft
$454 - $714
Taxes
$3,382 (2025)
Parking Type
-
Style
Bungalow
See what's nearby
Description
A rare opportunity to own a deep Georgian Bay waterfront property on one of Lion's Head's most desirable no-exit roads. The property extends to the 100-year high-water mark with no shore road allowance between the lot and Georgian Bay. A recent survey is available, with exact dimensions to be confirmed.Classic Bruce Peninsula limestone shoreline sets the scene for incredible views across the bay toward the iconic Lion's Head cliffs. Watch the sun rise over Georgian Bay, evening light sweep across the Escarpment and, on the right night, the full moon rise over the cliffs.The deep lot is what makes this property especially compelling, offering the space and setting to consider a future cottage or year-round home while the existing three-season cabin lets you enjoy the property now. Dating back to the 1930s, the rustic cottage is full of character with three sleeping areas, including a primary bedroom overlooking the water, a guest room and bunk room. A full wall of windows captures the waterfront views, while a cozy wood stove, functional kitchen and bathroom, and a mix of stone and wood flooring add to its timeless cottage charm.The cottage is serviced by a lake-drawn water system with shoreline pump house and a private septic system currently in working order. A storage shed provides additional space for tools and waterfront gear. The cottage could use some TLC, but remains a usable family retreat with plenty of life left in it-enjoy it as-is, improve it over time, or use it while exploring future plans.Set on a quiet, year-round municipally maintained road, the property is only minutes from Lion's Head for groceries, the marina, beach, hardware, medical services and the Saturday farmers' market. The Bruce Trail runs behind this stretch of Whippoorwill Road and is accessible on foot. Georgian Bay is at your doorstep for swimming, paddling, boating, sailing and fishing, while Bruce Peninsula National Park and Tobermory are an easy drive north.
Broker: Real Broker Ontario Ltd.
MLS®#: X13856940
Property details
Parking:
4
Parking type:
-
Property type:
Detached
Heating type:
Other
Style:
Bungalow
MLS Size:
700-1100 sqft
Lot front:
63 Ft
Lot depth:
260 Ft
Listed on:
Oct 2, 2026
Show all details
Instant estimate:
orto view instant estimate
$15,834
higher than listed price
i
High
$540,704
Mid
$515,734
Low
$489,477
Have a home? See what it's worth with an instant estimate

Use our AI-assisted tool to get an instant estimate of your home's value, up-to-date neighbourhood sales data, and tips on how to sell for more.

1 Helen Street
1/46
$499,900
9 days
1 Helen Street
2+2BD
2BA
6 Parking
700-1,100 sqft
MLS#: X13819750
RE/MAX REALTY SERVICES INC.
9 days

About 38 Whippoorwill Road

38 Whippoorwill Road is a Lion's Head detached house for sale. It has been listed at $499900 since October 2026. This 700-1100 sqft detached house has 3 beds and 1 bathroom.

For groceries or a pharmacy you'll likely need to hop into your car as there is not much near this detached house.

Getting around the area will require a vehicle, as there are no nearby transit stops.