Mister Waterfront Real Estate Team
416-407-8074
scott@misterwaterfront.com
RE/MAX Crosstown
566 Bryne Dr., Unit A
Barrie, ON
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RE/MAX Crosstown
RE/MAX Crosstown
Oro-medonte Waterfront properties
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1775 Ridge Road W in Oro-Medonte: Shanty Bay House for sale : MLS®# S6655772
1775 Ridge Road W Oro-Medonte L0L 2L0 
$37,000,000Residential Freehold- Status:
- Active
- MLS® Num:
- S6655772
- Bedrooms:
- 8
- Bathrooms:
- 11
Welcome to this exquisite waterfront estate nestled on sprawling 10 acres. The palatial mansion is truly a masterpiece, offering breathtaking vistas of Kempenfelt Bay on Lake Simcoe. Boasting expansive views of blue water, complemented by a range of luxe amenities. Featuring garage space for 8-cars, an indoor pool and spa, an outdoor pool and meticulously terraced grounds and tennis court. Boathouse with a finished loft and separate 3-bedroom gate house ensure ample space for guests, Designer interiors impress with gorgeous custom chef's kitchen. The primary suite offers an enormous walk-in closet, dressing room and spa-like bathroom. Towering trees line the winding drive that leads to this private oasis, located just a 1-hour drive from Toronto and 10 minutes to private airport. With 385 feet of shoreline, a private pier and unparalleled beauty both inside and out, this waterfront estate is truly a dream come true. **EXTRAS** Local Lake Simcoe Regional Airport supplies full service for private jets, helicopters and charters. Situated in the historic hamlet of Shanty Bay, one of Ontario's most desired areas for country homes and private waterfront estates. More detailsListed by RE/MAX HALLMARK YORK GROUP REALTY LTD. BROKERAGE and RE/MAX HALLMARK YORK GROUP REALTY LTD.- Scott Bird
- Re/Max Crosstown
- 416-407-8074
- Contact by Email
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2653 Ridge Road W in Oro-Medonte: Shanty Bay House for sale : MLS®# S12303760
2653 Ridge Road W Oro-Medonte L0L 2L0
$17,900,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12303760
- Bedrooms:
- 6
- Bathrooms:
- 7
One Of A Kind! Lighthouse Estate Family Compound ~ Rare 17.24-Acres And 525 Ft Of Prime Waterfront On Kempenfelt Bay/Lake Simcoe With Impressive Panoramic Views! Picturesque Drive Leading To 2 Magnificent Homes Each Inc: Aprox 15,000 Sf, Lower Level Walk/Outs, Apartments Over Both 3-Car Garage, Floor To Ceiling Glass Windows Throughout, 6 Bdrms, 6 Baths, Gym, Spa, Detached Utility Garagex 2. Sandy Beach, Rare Oversized Inwater Boathouse W/Living And Terrace More detailsListed by HARVEY KALLES REAL ESTATE LTD. and RE/MAX REALTRON BARRY COHEN HOMES INC.- Scott Bird
- Re/Max Crosstown
- 416-407-8074
- Contact by Email
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2533 Ridge Road W in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12345254
2533 Ridge Road W Oro-Medonte L0L 2L0
$15,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12345254
- Bedrooms:
- 5
- Bathrooms:
- 6
Welcome to 2533 Ridge Road West - A Private Waterfront Sanctuary on Lake Simcoe. Discover an extraordinary opportunity to own a 17.5-acre private resort estate nestled along the pristine shores of Kempenfelt Bay. This one-of-a-kind sanctuary boasts 893 feet of uninterrupted, south-facing waterfront a rare and coveted offering that perfectly blends natural beauty with luxury living. As you pass through the gated entrance, you are greeted by impeccably manicured grounds that set the tone for this exceptional lakeside retreat. Located just one hour from Toronto and mere minutes from the heart of downtown Barrie, this secluded paradise offers unmatched privacy without compromising convenience. The main residence spans over 6,100 square feet of refined living space, featuring 5 spacious bedrooms and 6 luxurious bathrooms. Designed to embrace its breathtaking surroundings, the home is lined with floor-to-ceiling windows that flood every room with natural light and offer sweeping, uninterrupted views of the tranquil lake. Step outside to experience an entertainers dream. Expansive, multi-level stone terraces lead to a custom-designed infinity pool, complete with a swim-up covered bar, cascading stone waterfalls, and a resort-style pool house perfect for hosting unforgettable summer gatherings. Soak in the built-in hot tub or unwind in the multiple outdoor lounge areas as you take in the serenity of the water and landscaped grounds. Follow the stone pathway down to the waters edge where a permanent dock, gazebo, custom bar, and lakeside hot tub (increasingly hard to find these days) await all perched on a beautifully crafted waterfront patio designed for ultimate relaxation and enjoyment. Whether you're seeking a luxurious family compound, a serene weekend retreat, or a unique waterfront investment, this spectacular estate delivers on every level. Welcome to lakeside living at its finest. More detailsListed by Sotheby's International Realty Canada- Scott Bird
- Re/Max Crosstown
- 416-407-8074
- Contact by Email
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1125 Woodland Drive in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12423947
1125 Woodland Drive Oro-Medonte L3V 6H1
$1,499,900Residential Freehold- Status:
- Active
- MLS® Num:
- S12423947
- Bedrooms:
- 3
- Bathrooms:
- 2
Welcome to your private lakeside retreat, where 72 feet of pristine, hard-bottom lakefront meets sparkling, crystal-clear watersideal for swimming, boating, and unforgettable sunsets. This fully winterized 3-bedroom, 2-bathroom bungalow sits on a beautifully treed lot, offering a peaceful, natural setting with uninterrupted water views from the moment you arrive. The open-concept living area with new vinyl flooring features a cozy wood-burning fireplace and a walkout to an expansive deck that stretches toward the lake perfect for relaxing or entertaining with the water just steps away. The lakeside eat-in kitchen is designed for both function and view, featuring stainless steel appliances including a 6-burner gas stove, fridge, and dishwasher all while enjoying panoramic views of the shoreline. Wake up every morning to the beauty of the lake in your primary bedroom with ensuite. Two additional bedrooms and a full 4-piece bath provide comfortable space for guests or family. Downstairs, a basement offers laundry and abundant storage space. But the true centerpiece? The 30' x 33' waterfront deck ideal for lakeside lounging or hosting summer gatherings with the gentle sound of the water below. Take full advantage of lake life with a 26.5' x 16' boathouse featuring a marine railway, ready for your boat and water toys. Above it, a 29' x 18' concrete deck sets the scene for unforgettable evenings under the stars. This is more than a home its a lifestyle on the lake. More detailsListed by RE/MAX HALLMARK CHAY REALTY- Scott Bird
- Re/Max Crosstown
- 416-407-8074
- Contact by Email
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3 Greenwood Forest Road in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12472828
3 Greenwood Forest Road Oro-Medonte L0L 2E0
$2,395,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12472828
- Bedrooms:
- 4
- Bathrooms:
- 3
Client RemarksWelcome to your Lakefront Dream Home, nestled on Greenwood Forest Road in one of Oro Medontes sought after neighborhoods. Luxury living meets a relaxed lakeside lifestyle. This meticulously updated waterfront bungalow on a quiet street offers breathtaking, open concept unobstructed views across to Big Bay Point. Enjoy spectacular sunrises from this 50 x 259 picturesque lot with over 3,200 sq. ft. of finished living space with a custom detached 3 bay 30 x 24 1.5 -storey garage, heated with natural gas. The show-stopping custom kitchen filled with natural light and vaulted ceilings is an entertainers dream. Finished with quartz counters, quartz backsplash, a striking oversized island with GE Cafe appliances with built-in bar/servery. This home features 3 bedrooms on the main floor with one 3 piece full bathroom and one 2 piece powder room. In the fully finished lower level, you will find 1 bedroom with ensuite , walk in shower ,heated floors and large family room with gas fireplace, custom built office space and high speed internet perfect for those that work from home. Outside youll find a concrete pier at the waters edge with cantilever dock, outdoor kitchen with dual Napoleon gas and charcoal BBQs, lush landscaping, interlock patios with walkway to the lake and fire pit seating area with a stunning view. New Lennox furnace and AC (2022), new Generac (2023), 200 AMP service. New septic system (2018), new water softener system with iron filter (2022).Ideal location for a short commute, 1 hr to Toronto, 10 minutes to Barrie/Orillia and a short boat ride to the prestigious Friday Harbour. Property has an invisible dog fence. More detailsListed by FOREST HILL REAL ESTATE INC.- Scott Bird
- Re/Max Crosstown
- 416-407-8074
- Contact by Email
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17 Stanley Avenue in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12512838
17 Stanley Avenue Oro-Medonte L0L 1T0
$1,249,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12512838
- Bedrooms:
- 2
- Bathrooms:
- 2
UNMATCHED LAKE SIMCOE LIVING WITH 50 FT OF PRIVATE SHORELINE - RELAX, UNWIND, & ENJOY LAKESIDE SERENITY EVERY DAY! Experience the best of lakeside living with this charming bungalow nestled in the tranquil Simcoeside neighbourhood along the scenic shores of Lake Simcoe. Wake up to mesmerizing sunrises and enjoy 50 feet of private waterfront, complete with a personal dock for effortless access to boating, fishing, and swimming. The landscaped and fully fenced yard offers lush greenery, vibrant gardens, and a stamped concrete walkway leading to the inviting front entrance, while the back porch and patio create the ideal space to unwind and take in panoramic lake views, with a staircase leading directly down to the dock. Inside, the open-concept main floor showcases a seamless connection between the kitchen, living room, and dining area, all bathed in natural light from expansive windows and a sliding glass walkout that beautifully frames the water. The main level includes a stylish 4-piece bath and a large primary bedroom with a walk-in closet, while the fully finished basement extends the living space with a generous rec room featuring an electric fireplace, a second bedroom, a 3-piece bath, and laundry with storage - plus the potential to add another bedroom if desired. The detached garage has been thoughtfully converted into a cozy multi-purpose retreat with a ductless heat pump, easily returned to a traditional garage if preferred. A trailer is also included for guests, creating the perfect setup for entertaining or extended summer stays. Ideally located just moments from the Hawkstone Yacht Club, Trehaven Golf and Country Club, Bayview Memorial Park and Beach, and scenic trails, plus only a short drive to Orillia, Barrie, and Horseshoe Valley for shopping, dining, and year-round recreation, this inviting #HomeToStay combines privacy, comfort, and lakeside charm - a rare opportunity to truly embrace the Lake Simcoe lifestyle! More detailsListed by RE/MAX HALLMARK PEGGY HILL GROUP REALTY- Scott Bird
- Re/Max Crosstown
- 416-407-8074
- Contact by Email
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2371 Lakeshore Road E in Oro-Medonte: Hawkestone House for sale : MLS®# S12527924
2371 Lakeshore Road E Oro-Medonte L0L 1T0
$1,925,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12527924
- Bedrooms:
- 3
- Bathrooms:
- 2
Welcome to this beautifully renovated bungalow, perfectly positioned on the inviting shores of Lake Simcoe. This home is an ideal retreat for those who cherish waterfront living with modern comforts. Completely remodeled from top to bottom this cottage or waterfront home is practically brand new inside and out. Upon entering, you are welcomed into a spacious open-concept area, where stunning lake views meet high-end finishes. The kitchen boasts quartz countertops and new stainless steel appliances, creating a stylish and functional space for cooking and entertaining. Adjacent is the living and dining area, complete with a new gas fireplace, adding warmth and ambiance to the room. The home features two large bedrooms, ample space for family and guests. Additionally, a quaint one-bedroom bunkie with a private balcony offers extra accommodation, perfect for visitors seeking privacy. For those considering future expansions, permit-ready plans are available. These include adding a main floor primary suite with a full en-suite bathroom and a third bedroom on the lower level, enhancing the homes versatility and appeal. Outside, a new 40-foot dock and expansive deck await with a stand for kayaks and paddle boards, setting the stage for unforgettable summer days filled with water activities and relaxation. Upgrades include new James Hardie siding, new electrical panel and wiring throughout the house, upgraded well & UV system, new asphalt driveway, landscaping completely redone, new glass railings throughout interior & exterior, new soffit and fascia (2021) and more. With gorgeous south east views across Carthew Bay and Lake Simcoe, this waterfront gem is ready to be your summer sanctuary. Located less than 15 minutes to Orillia for shopping, and an hour from the GTA, access and convenience is a breeze. More detailsListed by ENGEL & VOLKERS BARRIE- Scott Bird
- Re/Max Crosstown
- 416-407-8074
- Contact by Email
Data was last updated November 30, 2025 at 07:15 PM (UTC)
RE/MAX Crosstown
Office Address:
566 Bryne Dr., Unit A
Barrie, ON, L4N 9P6