luxury houses with sea view for sale Oro-Medonte, Canada

Welcome to your new Grape Island family cottage compound! This stunning Lake Simcoe property overlooks tranquil Lake Simcoe in Orillia, just one hour from the Greater Toronto Area. Viceroy-style main cottage with 565 feet of south-east and west shoreline on 1.146 acres on a very private south-facing point of land for all-day sun, along with east sunrise and west sunset views. The soaring great room and open-concept kitchen with plenty of natural light is perfect for preparing dinner for family and friends. For those who prefer to be outside, the deck that spans the front of this property also offers a fully-equipped outdoor barbecue kitchen. A multitude of windows span the entire front of the cottage and provide breathtaking long lake views! Open concept living spaces afford easy guest flow throughout the cottage. Stunning natural landscapes feature stone steps leading down to a dock and boat lift with forested trails that surround the property. Excellent swimming and boating with deep water off the dock and a sandy entry. Enjoy long sun-drenched days on the south-west-facing decks or warm you and your guests by the fire or in the hot tub. Includes two guest bunkies and a water closet with access to the garden.

Welcome to 45 Ivy Lane on Grape Island, a rare private island retreat offering 1.2 acres of landscaped grounds and 233 feet of pristine Lake Simcoe shoreline. Designed for exceptional waterfront living, this one-of-a-kind compound combines luxury accommodations, resort-inspired amenities, and remarkable privacy just a short boat ride from the mainland. The property offers multiple gathering and accommodation spaces, comfortably hosting family and guests across five distinct sleeping areas. At its heart is a spectacular boathouse with waterfront primary suite, complemented by thoughtfully designed indoor and outdoor living spaces that embrace the lake from every angle. Extensive improvements and upgrades have transformed the property into a sophisticated island escape. A rooftop deck captures panoramic lake views, while the swim spa, yoga room, outdoor showers, and expansive multi-level decks create an atmosphere more reminiscent of a boutique resort than a traditional cottage. The retractable dock system and waterfront infrastructure provide seamless enjoyment of Lake Simcoe's boating and water recreation. Over two million dollars has been invested in the property, including significant renovations, infrastructure improvements, and modernization of key systems including $200k in 2023 for new septic and landscaping. Documentation relating to permits, inspections, renovations, and major improvements is available for review. Whether envisioned as a private family compound, a multi-generational retreat, or an unforgettable place to entertain, 45 Ivy Lane offers a rare opportunity to own one of Lake Simcoe's most distinctive island properties. A 600 foot cedar hedge and 6 foot high wrought iron fencing encloses the property. Fully furnished (perfect mix of mid-century and contemporary cottage) and move-in ready. Be in total privacy less than two hours from Toronto. VTB available for qualified buyers.

Waterstone Estate on Hedge Road does not announce itself. It does not need to. For those who know, the name alone is enough - a quiet signal of something earned over time, passed through time, and understood rather than explained. 30 Hedge Road is offered for the first time in nearly 50 years, and it arrives carrying the full weight of that history. Set behind a curtain of mature cedars on 178 feet of private Lake Simcoe shoreline, this property offers a rare and complete sense of seclusion - a world apart, entirely your own. This meticulously maintained 2,687 square foot Colonial Revival stone cottage has sheltered summers of extraordinary grace - mornings that begin with the sound of waves against the dock, long afternoons of children swimming in clear water, a short walk to the ice cream store on a sunny afternoon, and evenings that belong entirely to a breathtaking sunset over the lake and a glass of wine raised in celebration of nowhere else you would rather be. At night, the bedroom windows stay open and the breeze off the lake carries you to sleep. The Great Room commands with vaulted coffered ceilings, skylights, hardwood floors, and a stone fireplace that has warmed three generations. A gracious columned veranda greets you at the front, while a sun-drenched flagstone patio extends living gracefully toward the water. Three fully self-contained guest suites - one within the residence with a private bedroom, bathroom, living room, and separate entrance; a third bedroom with its own private bathroom; and a waterfront retreat with bedroom, bathroom, and screened-in sun porch above the lake - ensure family, near and far, is always welcome and never crowded. Seasonal dock with deep water access. Directly across from Briars Resort and Golf Club. Just over an hour to Toronto. A legacy, by every measure, is waiting for you.

Winter Wind Cottage sits on an extra-wide waterfront lot on Hedge Road, one of Jacksons Point's most sought-after streets. Private and surrounded by mature greenery, the property offers flat, usable table land that creates the perfect setting for outdoor entertaining, family gatherings, and space for children to play. A newly built staircase winds through the hedges to two tiers of waterfront decking, where the natural rock shelf transitions to a sandy lake entry, creating an exceptional waterfront experience. Inside, the home is thoughtfully designed around its connection to the water. The kitchen, illuminated by a skylight beneath a cathedral ceiling, flows into a glass-lined dining room overlooking Lake Simcoe, while the adjoining great room features exposed beams, a dramatic floor-to-ceiling fireplace, and expansive windows that frame the lake as a constant backdrop. With four bedrooms and three bathrooms, the layout offers generous space for family and guests. Designed with a wide footprint rather than a deep one, the home captures lake views from nearly every principal room. Enjoy the cottage as it is while planning future possibilities, or begin reimagining the property immediately. The exceptional lot offers the flexibility to renovate, expand, or build new, while giving you the freedom to move at your own pace. Located in the heart of Jacksons Point, a community that has long been regarded as Toronto's original cottage country, you're just a short walk to The Briars, village shops, and the local ice cream store. Lake Simcoe offers exceptional four-season recreation, from boating, swimming, and fishing in the summer to skating and ice fishing in the winter. Winter Wind Cottage is a rare opportunity to own a timeless waterfront property in one of Lake Simcoe's most cherished communities.

In the same family for nearly 60 years and lovingly maintained, Sunset Serenade is a rare offering set on a deep lot, with nearly 60 feet of waterfront in the storied Orchard Beach enclave of Georgina's Historic Lakeshore. A true four-season retreat for the whole family, this home includes a private waterfront parcel with its own pebbled sandy beach- perfect for swimming all day long - while a generous front garden gives way to a mature, treed and private back yard. Spend mornings at the beach, lunch in the front garden, steal an afternoon nap on the enclosed front porch overlooking the lake, then BBQ dinner on the side deck as the day winds down. As evening falls, gather family & friends at the private beach firepit for uninterrupted, west-facing sunsets over the water - the namesake views that make this property special. In winter you can enjoy ice-fishing or skating from your lakefront and relish the same sunsets from a cozy, upstairs lounge or the winterized front porch. Lake views find you throughout the home, from the front porch to two separate sitting areas. Inside, a sky-lit breakfast area flows off the kitchen for easy everyday living, complemented by a dedicated office. A formal sitting room - anchored by a handsome stone fireplace - and a third rec room on the second level with its own lake views, offer exceptional space for a large, growing family. The home is protected by a durable metal roof, classic persiana-style shutters, interlocking stone, and vinyl-cladding. Part of the original orchard itself, this home is set within one of Ontario's most exclusive lakeshore communities, with roots dating to the Roches Point land grant and Eastbourne Golf Club, Orchard Beach remains one of the last communities blending cottage charm, lake recreation and year-round living less an hour from Toronto. This is a once-in-a-generation opportunity to own a true piece of Lake Simcoe history, moments from marinas, restaurants & golf. Some AI-generated photos, not real.