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.
5 bedrooms, 3 bathrooms, about 3,000 sq ft, works out to roughly $1,497 per square foot. Chat with Zara if you'd like a deeper read on whether this detached fits your budget and timing.
Inside 209 Bay St
Every detail from the listing, in one place.
Type
Detached
Style
2-Storey
Living space
3000-3500 sq ftas stated on the listing
Parking
12 spacesYes garage
Basement
Full, Unfinished
Features & systems
Parking & garage
Garage
Yes
Parking spaces
12
Interior
Basement
Full · Unfinished
Lot & land
Lot size (sqft)
0
Listing & possession
Property style
2-Storey
Property class
Detached
209 Bay St Price & Sale History
Earlier listings of this property, list-price changes, and the most recent annual property tax on the listing.
For saleListedThis listingMLS® S13508726$4,490,000
Sourced from MLS®. Includes earlier listings of this property on record.
What's it worth?
How 209 Bay St Compares to the Oro-Medonte Market
Zara compares it with recent sales of similar homes nearby. It's a guide, not an appraisal.
Independent mortgage broker · OAC · rates subject to change and underwritingMortgage Squad →
Referral disclosure: Summitly may refer you to Mortgage Squad Advisors, an affiliated mortgage partner. You are free to choose any lender or mortgage professional.
Monthly cost
Enter a rate to see the monthly cost
An estimate, not a quote. Utilities and insurance are extra.
Affordability calculator
Estimated monthly payment
$22,058
/mo
based on the purchase price of $4,490,000
$898,000 cash
$3,592,000 financed
$3,025,407 total interest
Principal54%$3,592,000
Interest46%$3,025,407
20% down · 25-yr amortization · 5.50% rate. Principal & interest only — taxes, condo fees, and insurance not included.
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Figures are Summitly estimates for illustration only — not from TRREB or the MLS® feed, and not a mortgage approval, appraisal, or financial advice.
Rental income potential
Est. monthly rent
low–high
Gross yield
rent × 12 ÷ price
Cap rate (est.)
net of tax + fees
Summitly AI estimate for discussion only — not from TRREB or the MLS® feed, and not an appraisal or investment advice. Yield and cap rate are derived from the estimated rent versus the asking price.
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Mortgage financing is arranged through Mortgage Squad Advisors. Summitly is the technology platform that powers this site. Estimated values, AI insights, calculator results, and rental projections shown on this page are generated by Summitly and are not provided by, reviewed by, or sourced from TRREB, the MLS®, or the listing brokerage; they are not appraisals or opinions of value. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by the Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The Coldwell Banker® name and logo are trademarks of Coldwell Banker Real Estate LLC.
Keep looking near 209 Bay St
Homes for sale in Oro-Medonte
Every active Oro-Medonte MLS® listing, updated all day.
Average days on market38Homes sold in about 38 days on average.
Sale-to-list ratio95.9%On average, homes sold below asking.
Active listings254Homes for sale here right now.
Median vs prior 90 days+2.9%Compared with Apr 24 – Jul 23, 2026: prices up.
Based on 130 sales from Jul 23 – Oct 21, 2026 (91 in the prior 90 days). Aggregate MLS® figures for closed sales; individual sold prices are shown only to signed-in members.
Questions About 209 Bay St
How much is 209 Bay St listed for?
209 Bay St is listed at $4,490,000 (MLS® S13508726). Summitly updates the price as soon as the MLS® record changes.
Is $4,490,000 a good price for 209 Bay St?
Summitly rates it Well Above Market: the asking price is 15% or more above Zara's estimate, an estimate built from recent sales in Oro-Medonte. The rating is an automated opinion, not an appraisal; "What's it worth?" on this page shows how it is worked out. See Zara's estimate
Has the price of 209 Bay St changed?
No — 209 Bay St is still listed at its original asking price of $4,490,000.
How many bedrooms and bathrooms does 209 Bay St have?
209 Bay St has 5 bedrooms and 3 bathrooms, with about 3,000–3,500 square feet of living space. It is a detached home in Oro-Medonte.
How much would the monthly mortgage be on 209 Bay St?
About $22,058 a month — principal and interest on $4,490,000 with 20% down ($898,000), a 25-year amortization and an assumed 5.5% interest rate. The mortgage calculator on this page lets you change the down payment, amortization and rate.
How does 209 Bay St compare with other homes in Oro-Medonte?
Its asking price of $4,490,000 is about 399% above the median sold price in Oro-Medonte over the last 90 days, $900,000, across 130 closed sales on the TRREB MLS®. A city median mixes every type and size of home, so the comparable sales on this page are the closer guide.
Has 209 Bay St been sold before?
Summitly has no earlier MLS® sale or lease of 209 Bay St on record from the last two years. Older records aren't shown under TRREB rules.
Where is 209 Bay St?
209 Bay St is in Oro-Medonte, ON. Schools, transit, parks and shops nearby are under Location & lifestyle on this page.
How long has 209 Bay St been on the market?
112 days — 209 Bay St was listed on July 1, 2026.
What is the price per square foot of 209 Bay St?
About $1,283 to $1,497 per square foot: the asking price of $4,490,000 over the 3,000–3,500 sq ft the listing gives as its size range.
Does 209 Bay St have parking or a garage?
Yes — the listing gives 12 parking spaces. Garage: Yes.
Does 209 Bay St have a basement, and is it finished?
The listing describes the basement as: Full, Unfinished.