206 feet of west-facing private shoreline on Lake Simcoe. A custom round-log home built in 2005 by Moonstone Timberframe. Nearly 5,000 square feet of finished living space with panoramic lake views from nearly every room. One of the rarest frontages in the region, and one of Orillia's most exceptional waterfront homes to sit on it. The property is set at the narrows connecting Lake Simcoe and Lake Couchiching, with direct access to the Trent-Severn Waterway. West-facing exposure delivers unforgettable sunsets year-round. Inside, an almost 30-foot vaulted great room showcases true round-log construction and stunning stonework around the gas fireplace. The chef's kitchen is the showpiece, with an oversized island, Elmira Heritage appliances, and wraparound views of the lake. The main-floor primary suite features a 5-piece ensuite, walk-in closet, in-suite laundry, and private access to the expansive glass-railed deck overlooking Lake Simcoe. Upstairs, an open loft currently functions as a lounge and home office, originally designed to accommodate two additional bedrooms and a full bathroom. The fully finished walkout lower level includes in-floor heating throughout, an entertainer's bar, media room, two large guest bedrooms, a full bathroom with laundry hookup, and access to a screened-in porch and covered patio. At the water's edge, a 458 square foot finished boathouse bunkie with waterfront deck adds guest accommodation steps from the shoreline. The 1,289 square foot heated garage and workshop easily stores a 38-foot boat plus at least two vehicles. On the water: a 60-foot cantilever dock, a large observation deck, a boat rail system, and an additional floating dock. The kind of waterfront setup that takes years to permit and years more to build. Ten minutes to Orillia, under an hour to Muskoka, and about an hour from the GTA. Lakeside living, on 206 feet you'll never find twice. See agent website for additional photos and floor plans.
Waterfront lot on Lake Simcoe with landscaped grounds
Dock and boat slip
Boat house
Deck
Outdoor lighting
Home design
Single family detached residence
Log and stone construction
Facing west
Parking
12 total parking spaces, 5 covered
Detached garage with garage door opener
Private circular driveway
Security
Security system
Smoke detectors
Construction
Metal roof
Utilities
Private well water
Septic tank
Cable available
Natural gas available
Sale and tax history for 99 Creighton St
Sale History
Tax History
Date
Event
Price
TREB #S13548536
Jul 10, 2026
Listed
$3,295,000
TREB #S12962850
Apr 7, 2026
Listed
$3,499,000
TREB #S12216119
Oct 1, 2025
Delisted
—
Jun 12, 2025
Listed
$3,899,900
+2
Welcome to 'Four Winds', one of Orillia's most exceptional waterfront properties located on Lake Simcoe. Situated on a rare 206 feet of private shoreline, this 2005-built round log home by Moonstone Timberframe with almost 5000 square feet of finished living space, offers timeless craftsmanship, remarkable design, and panoramic lake views from nearly every room. West-facing exposure delivers unforgettable sunsets, while the setting near the narrows connecting Lake Simcoe and Lake Couchiching offers incredible access to the Trent Severn Waterway and year-round enjoyment. Inside, a 30-ft vaulted great room showcases true log construction and stunning stonework around the gas fireplace. The chefs kitchen is a showpiece with an oversized island, high-end Elmira Heritage appliances, and wraparound views of the lake. The main floor primary suite features a 5-piece ensuite, walk-in closet, in-suite laundry, and private access to the expansive glass-railed deck overlooking the lake. Upstairs, a spacious open loft currently functions as a lounge and home office, originally designed to accommodate 2 additional bedrooms and a full bathroom. The fully finished walkout basement includes in-floor heating throughout, an entertainers bar, media room, two large guest bedrooms, full bathroom with laundry hookup, and access to a screened-in porch and covered patio. At the waters edge, a 458 sq ft finished boathouse bunkie with waterfront deck offers additional guest space. The 1,289 sq ft heated garage/workshop easily stores up to a 38-ft boat plus 2 vehicles. On the water, enjoy a 60ft cantilever dock, large observation deck, boat rail system and additional floating dock. Just 10 minutes to Orillia, under an hour to Muskoka, and only an hour from the GTA, this is lakeside living at its absolute finest. See agent website for info, photos and floor plans.
TREB #X2153145
Sep 16, 2011
Delisted
—
Jul 14, 2011
Listed
$1,499,999
TREB #X1356740
Apr 29, 2008
Delisted
—
Apr 23, 2008
Listed
$2,290,000
As the MLS and public records start to fill up, we'll list the details here.
Public record
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Single Family Residential
Region
Simcoe County
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Last updated by owner on Aug 9, 2023.
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