209 Bay Street, Oro-Medonte, ON L0L 2L0, Oro-Medonte, ON
Bed 5
Bath 5
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.
Property Highlights
For Sale
MLS NO.
S13508726
Type
Residential Freehold
Sub Type
Detached
Bedrooms
5
Bathrooms
5
Parking
12.0
Garage
Yes
Complete Property Details
Property Type
Residential Freehold
Sub Type
Detached
Transaction Type
For Sale
Status
Active
Contract Status
Available
MLS® Number
S13508726
Living Area Range
3000-3500
Total Bedrooms
5
Bedrooms Above Grade
5
Total Bathrooms
5
Total Kitchens
1
Kitchens Above Grade
1
Rooms Above Grade
9
Interior Features
Generator - Partial, Auto Garage Door Remote
Fireplace
Yes
Fireplace Features
Living Room, Family Room, Wood, Natural Gas
Central Vacuum Yn
No
Construction
Vinyl Siding
Roof
Asphalt Shingle
Lot Width
200.0
Parking Features
Private Triple
Parking Total
12.0
Covered Spaces
2.0
Garage Type
Detached
Garage
Yes
Pool
None
Direction Facing
South
Cooling
Central Air
Heat Source
Gas
Heat Type
Forced Air
Internet Address Display Yn
Yes
Internet Entire Listing Display Yn
Yes
Full Address
209 Bay Street, Oro-Medonte, ON L0L 2L0
City
Oro-Medonte
Neighbourhood
Shanty Bay
County / Region
Simcoe
Province / State
ON
Postal Code
L0L 2L0
Cross Street
Ridge/Line 2
Directions
Ridge Road to Line 2 South To Bay
Country
CA
List Price
$4,490,000
Annual Taxes
$15,001
Tax Year
2025
Legal Description
LT 2 PL 742 ORO; ORO-MEDONTE
Possession Type
Flexible
Listing Office
RE/MAX HALLMARK CHAY REALTY
Board
Toronto Regional Real Estate Board
Original Entry
2026-07-01T14:24:57Z
Media Updated
2026-07-01T14:24:57Z
Photos Updated
2026-07-01T14:24:57Z
Last Modified
2026-07-01T14:24:57Z
System Modified
2026-07-06T21:41:50.607707Z
MLS Status
New
Architectural Style
2-Storey
Basement
Full, Unfinished
Co List Office Name
RE/MAX HALLMARK CHAY REALTY
Ddfyn
Yes
Expiration Date
2026-10-15
Foundation Details
Concrete Block
Heat Source Multi
Gas
Heat Type Multi
Forced Air
Hstapplication
Included In
Link Yn
No
Occupant Type
Vacant
Originating System Id
A00001796
Parcel Number
585550037
Parking Spaces
10
Property Features
Waterfront, Wooded/Treed, Lake/Pond, Cul de Sac/Dead End
Public Remarks
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.
