38 Whippoorwill Road

About this Property

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.

Listing Details

MLS #

40868320

Board

ITSO

Market

ontario

Property Type

Single Family Residence

Style

Cottage

Parking Spaces

4

Basement

Crawl Space, Unfinished

Heating

Wood, Wood Stove

Cooling

None

Lot Size

63.50 × 260 ft

Annual Taxes

$3,382/yr

Listed By (Primary)

Real Broker Ontario Ltd.

Co-Listed By

Real Broker Ontario Ltd

Presented By

REMAX Hallmark®

Listed On

October 2, 2026

Days on Market

3

Features & Extras