Listed by Re/Max Hallmark Chay Realty.

209 Bay Street is a Detached, 2-Storey and is currently for Sale @ $4,799,900. Taxes in 2025 were $15,001.45.

More homes for sale under 4.8M in Oro-Medonte

A rare opportunity to own a true waterfront retreat in the heart of Shanty Bay. The 2-Storey on 209 Bay Street has 5 bedrooms, 5 bathrooms, and is located on a 156 x 200 ft lot in the community 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.

Dishwasher, Dryer, Gas Oven/Range, Refrigerator, Washer, Appliances in bunkie and guest house. Docking. Generator.

The address 209 Bay Street was listed for sale (MLS# S12875984) on Thursday, March 12, 2026.