Rare Waterfront Estate in Prestigious Shanty BayA rare opportunity to own an exceptional waterfront retreat in the heart of Shanty Bay. Tucked away on a quiet dead-end street, this remarkable property offers nearly 200 feet of pristine, south-facing shoreline on Kempenfelt Bay, with crystal-clear deep water ideal for swimming, boating, and enjoying breathtaking panoramic views. Set on a private, beautifully treed lot, the estate includes a main cottage, guest house, and bunkie above the garage, providing a total of 12 bedrooms, 8 bathrooms, and 3 kitchens. With ample space for extended family, guests, or potential rental income, this property offers outstanding versatility. Most principal rooms capture stunning lake views, while the outdoor spaces are designed to embrace waterfront living. Features include a lakeside concrete patio, marine railway with covered boat slip, and a spacious rooftop deck above the boathouse-perfect for entertaining and enjoying spectacular sunsets. The main cottage is filled with warmth and character, featuring hardwood floors, a stone fireplace, a charming Muskoka room overlooking the water, and a cozy third-level loft retreat. Additional highlights include a heated garage with bunkie accommodation above, parking for 10+ vehicles, and a secluded, park-like setting surrounded by mature trees for exceptional privacy. Conveniently located just 10 minutes from Barrie, Royal Victoria Regional Health Centre, shopping, dining, and everyday amenities, and approximately one hour from Toronto. Enjoy easy boat access to Friday Harbour Resort and nearby recreational trails. Whether enjoyed as a private family compound, multi-generational getaway, or investment opportunity with future severance or redevelopment potential, this is a rare chance to own a legacy waterfront property in one of Lake Simcoe's most coveted communities.
Single-familyProperty Type
0.72 acresLot Size
12 spacesParking
Listed by ELLIE LAFERRIERE• RE/MAX HALLMARK CHAY REALTY
Listed by RICK LAFERRIERE• RE/MAX HALLMARK CHAY REALTY
Two fireplaces (gas and wood burning) located in the living room and family room
Full unfinished basement
Heating & cooling
Central air conditioning
Natural gas forced-air heating
Exterior features
Private waterfront on Lake Simcoe with dock and boat slip
Deck and patio
Wooded, irregular lot
Frontage along waterfront (approx. 60.96')
Publicly maintained road access
Home design
Detached single-family home
Two-story
South-facing
Parking
Total of 12 parking spaces with 2 covered spaces
Detached garage with garage door opener
Construction
Vinyl siding
Asphalt roof
Utilities
Private well water
Septic tank sewage
Sale and tax history for 209 Bay St
Sale History
Tax History
Date
Event
Price
TREB #S13508726
Jul 1, 2026
Listed
$4,490,000
TREB #S12875984
Jul 1, 2026
Delisted
—
Mar 12, 2026
Listed
$4,799,900
+39
A rare opportunity to own a true waterfront retreat in the heart of Shanty Bay. Tucked away on a quiet dead-end street, this exceptional lakefront property boasts nearly 200 feet of pristine, south-facing shoreline with crystal-clear, deep water-perfect for swimming, boating, and enjoying breathtaking panoramic views across Kempenfelt Bay. Set on a beautifully treed and private lot, this remarkable estate features a main cottage, guest house, and a bunkie above the garage, offering a total of 12 bedrooms, 8 bathrooms, and 3 kitchens. Whether hosting extended family, entertaining guests, or exploring rental income opportunities, there is ample space for everyone. Most principal rooms capture stunning, unobstructed lake views, while the outdoor living spaces are designed to make the most of the waterfront lifestyle. Enjoy a private concrete lakeside patio, a marine railway with covered boat slip, and an expansive rooftop deck above the boathouse-an ideal setting for sunset entertaining. The main cottage is filled with warmth and character, featuring wood floors, a charming stone fireplace, a Muskoka room with spectacular water views, and a cozy third-level loft retreat. Additional highlights include a heated garage with bunkie above, parking for 10+ vehicles, and a secluded, park-like setting surrounded by mature trees for exceptional privacy. All of this is located just 10 minutes from Barrie, Royal Victoria Hospital, shops, and services, and only an hour from Toronto. Enjoy quick boat access to Friday Harbour's dining and amenities, or explore the nearby Simcoe Loop Trail for scenic walking and cycling. Whether you choose to enjoy this special property as it is, or explore its future severance or redevelopment potential, this is a once-in-a-lifetime opportunity to own a legacy lakefront estate in one of Lake Simcoe's most sought-after communities.
TREB #S12386085
Dec 1, 2025
Delisted
—
Sep 6, 2025
Listed
$4,999,900
+35
A rare opportunity to own a true waterfront retreat in the heart of Shanty Bay. Set on a quiet, dead-end street, this exceptional lakefront property offers almost 200 feet of south-facing shoreline with crystal-clear, deep waterperfect for swimming, boating, and soaking in panoramic views across Kempenfelt Bay. Set on a beautifully treed, private lot, this estate includes a main cottage, guest house, and a bunkie above the garagetotalling 12 bedrooms, 8 bathrooms, and 3 kitchens. Whether you're hosting extended family, entertaining guests, or exploring rental income, theres space for everyone. Enjoy unobstructed lake views from most principal rooms, and step outside to a host of outdoor features including: a Private concrete waterfront patio, a Marine railway with covered boat slip and an Expansive rooftop deck above the boat slipperfect for sunset entertaining. The main cottage exudes warmth and character, featuring wood floors, a charming stone fireplace, a Muskoka room with stunning views, and a cozy third-level loft. Additional highlights include: a Heated garage with bunkie above, Parking for 10+ vehicles, Secluded and a park-like setting with mature trees for total privacy. All this just 10 minutes to Barrie, Royal Victoria Hospital, shops, and servicesplus an easy 1-hour drive to Toronto. Enjoy quick boat access to Friday Harbours dining and amenities, and explore nearby Simcoe Loop Trail for walking and cycling. Whether you enjoy this special property as-is or explore its future severance or redevelopment potential, this is a once-in-a-lifetime opportunity to own a legacy lakefront estate in one of Lake Simcoes most desirable communities.
TREB #S12002759
Sep 6, 2025
Delisted
—
Mar 5, 2025
Listed
$4,999,900
TREB #S9247622
Nov 23, 2024
Delisted
—
Nov 1, 2024
Listed
$5,490,900
Nov 1, 2024
Delisted
—
Aug 9, 2024
Listed
$5,490,900
As the MLS and public records start to fill up, we'll list the details here.