209 Bay Street
Oro-Medonte, ON
- 5 bed
- 5 bath
- approx. 3000-3500 sqft
- Detached
- 78 days on market
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.
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Listing Details
- Taxes (2025)
- $15,001
- Listed
- July 1, 2026
Price History
Listing history
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Property
- Style
- 2-Storey
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete Block
- Interior
- Generator - Partial, Auto Garage Door Remote
- Lot Size
- 200 x 156 Feet
Parking
- Garage
- Detached
- Covered Spaces
- 2
- Total Parking
- 12
Utilities
- Water
- Drilled Well
- Sewer
- Septic
- Heat Source
- Gas
Location & Legal
- Cross Street
- Ridge/Line 2
- Parcel Number
- 585550037
- Possession
- Flexible
- Occupancy
- Vacant
Included
- Inclusions
- Dishwasher, Dryer, Gas Oven/Range, Refrigerator, Washer, Appliances in bunkie and guest house. Docking. Generator.
- Exclusions
- NONE
- Rental Items
- NONE
Waterfront
- Water Body
- Lake Simcoe
- Shoreline
- Clean, Rocky, Hard Bottom
- Docking
- Private
Schools
Elementary
- Shanty Bay Public School1.2 km
Public · Simcoe County DSB · 185 students
Grade 3 reading: 72% met the provincial standard · Grade 6 math: 70% met the provincial standard
Straight-line distance. Nearby schools are not necessarily the assigned schools — confirm catchment with the school board. Scores are EQAO provincial test results for 2024-2025.
Community
Postal area L0L
- Population
- 42,022
- Private dwellings
- 19,252
- Median age
- 46.8
- Average household size
- 2.7
- Median household income
- $106,000
Source: Statistics Canada, 2021 Census of Population, catalogue 98-401-X2021013. Adapted from Statistics Canada. This does not constitute an endorsement by Statistics Canada of this product.
Local market
Residential Freehold in Oro-Medonte · last 12 months
- Median sold price
- $890,000
- Homes sold
- 323
- Median days on market
- 32
- Sale-to-list price
- 95.9%
Based on 323 recorded sales of residential freehold properties in Oro-Medonte over the last 12 months.
Rooms
2-piece on Main, 5-piece on Second, 1-piece on Second, 3-piece on Second, 3-piece on Second
Third
- Bedroom12' x 8'
Second
- Bathroom6' x 6'
- Bathroom10' x 8'
- Bathroom6'7" x 8'2"
- Bathroom3'7" x 3'7"
- Bedroom12' x 12'
- Bedroom16' x 14'
- Bedroom13' x 11'
- Primary Bedroom16' x 14'
Main
- Bathroom6' x 4'
- Dining Room18' x 14'
- Family Room27' x 11'
- Kitchen13' x 15'
- Living Room21' x 15'
Listed by
RE/MAX HALLMARK CHAY REALTY
Walk Score
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Location
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Mortgage Calculator
$898,000
Estimated Monthly Payment
$22,058
Land transfer tax
Ontario land transfer tax only. An estimate — not legal or financial advice. Municipal land transfer tax applies in Toronto and is not included.
Investment Analysis
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Mortgage: $22,058/mo (20% down, 5.5%)
Taxes: $1,250/mo · Insurance: $1,123/mo
Estimates only. Consult a financial advisor.
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Reita is an automated assistant, not a licensed real estate agent. This listing mentions 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…. I can help you explore neighbourhoods, understand the market, and find our free tools. What are you looking for?