209 Bay Street, Oro-Medonte, ON L0L 2L0, Oro-Medonte, ON
Bed 5
Bath 5
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.
Property Highlights
For Sale
MLS NO.
S12875984
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
S12875984
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
$4,799,900
Annual Taxes
$15,001
Tax Year
2025
Legal Description
LT 2 PL 742 ORO; ORO-MEDONTE
Possession Type
Flexible
Possession Details
Flexible
Listing Office
RE/MAX HALLMARK CHAY REALTY
Board
Toronto Regional Real Estate Board
Original Entry
2026-03-12T15:24:56Z
Media Updated
2026-03-12T15:24:57Z
Photos Updated
2026-03-12T15:24:57Z
Last Modified
2026-03-19T20:48:57Z
System Modified
2026-03-19T20:49:08.015201Z
MLS Status
New
Architectural Style
2-Storey
Basement
Full, Unfinished
Co List Office Name
RE/MAX HALLMARK CHAY REALTY
Ddfyn
Yes
Expiration Date
2026-06-30
Foundation Details
Concrete Block
Heat Source Multi
Gas
Heat Type Multi
Forced Air
Hstapplication
Included In
Link Yn
No
Occupant Type
Owner
Originating System Id
A00001796
Parking Spaces
10
Property Features
Waterfront, Wooded/Treed, Lake/Pond, Cul de Sac/Dead End
Public Remarks
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.
