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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2371 Lakeshore Road E in Oro-Medonte: Hawkestone House for sale : MLS®# S12103747
2371 Lakeshore Road E Oro-Medonte L0L 1T0
$1,925,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12103747
- 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
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183 Lakeshore Road W in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12153515
183 Lakeshore Road W Oro-Medonte L0L 2E0
$2,999,900Residential Freehold- Status:
- Active
- MLS® Num:
- S12153515
- Bedrooms:
- 4
- Bathrooms:
- 5
Welcome to this exquisite 4 Bedroom, 7 Bath executive home on Lake Simcoe in Oro-Medonte. This residence epitomizes lakeside living, offering easy access to Barrie and Orillia, & the boundless opportunities provided by Lake Simcoe and the Trent-Severn Waterway. The grand entrance leads to an open-concept living/dining/eat-in kitchen area with oversized glass doors connecting you to a beautifully landscaped backyard & endless lake vistas. With over 97.09ft of water frontage, a private dock, marine railway system, play center, covered gazebo, glass balcony, meticulous landscaping, and privacy, there's no need for an additional seasonal home. The custom kitchen offers an elegant & functional space for both chefs and entertainers. Ample cupboards, glass-fronted doors, upgraded countertops, an eat-in banquette, open shelving, & a butler's pantry accommodate gatherings of all sizes. A grand Napoleon fireplace serves as a focal point, complemented by soaring cathedral ceilings reaching 16ft. All Bedrooms have their own ensuite bathrooms & walk-in closets. A wide hardwood staircase leads to the luxurious master suite, featuring a private oasis, custom walk-in closet, & a spacious ensuite. Wake up to spectacular lake views and mature trees, and enjoy the peaceful breeze on your private glass-paneled balcony. To the left of the main floor common areas, you'll find a butler's pantry, private laundry area, and a second tiled side/informal entrance. Inside access to the heated 2.5 car garage, which currently accommodates storage, & a workshop area. Additionally, there's access to the second floor (left wing) featuring an additional 3pc bathroom and a spacious office/gym with a wet bar and an open-concept layout. The partial-finished basement features a media room & 2pc bath. With proximity to major highways, one of the lowest tax rates in the region & a blend of rural and urban lifestyles, this home offers the best in both home ownership and real estate investment. More detailsListed by REVEL REALTY INC.- Scott Bird
- Re/Max Crosstown
- 416-407-8074
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2369 Lakeshore Road E in Oro-Medonte: Hawkestone House for sale : MLS®# S12216144
2369 Lakeshore Road E Oro-Medonte L0L 1T0
$2,699,999Residential Freehold- Status:
- Active
- MLS® Num:
- S12216144
- Bedrooms:
- 3
- Bathrooms:
- 2
Exceptional Waterfront Retreat on Lake Simcoe! This beautifully renovated home offers 50 feet of prime Lake Simcoe frontage in one of the areas most sought-after locations. With panoramic lake views and a thoughtfully designed layout, this property perfectly blends luxury and relaxation.The main home features a stunning open-concept design with cathedral ceilings and a seamless flow from the living space to the Muskoka room, complete with a cozy fireplace and walkout to a private deck overlooking the lake. The primary bedroom boasts a spa-like ensuite and walk-in closet, offering a serene escape. A separate guest suite ensures privacy and comfort for family and friends.The lower level presents breathtaking lake views, a family sitting room, and double walkouts, enhancing the connection to lakeside living. Outside, youll find a detached bunkie for additional accommodation and a waterside storage shed, versatile for all your waterfront needs.Located just minutes from Highway 400, this property is conveniently nestled between Barrie and Orillia, offering easy access to shopping, dining, and entertainment. Situated in a popular waterfront community, this home is a rare gem for year-round living or weekend escapes! Don't miss your chance to own this slice of paradise! More detailsListed by HARVEY KALLES REAL ESTATE LTD.- Scott Bird
- Re/Max Crosstown
- 416-407-8074
- Contact by Email
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6 Orillia Road in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12248709
6 Orillia Road Oro-Medonte L0L 2E0
$259,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12248709
Build your dream cottage or year-round home just steps from the shores of Lake Simcoe, yet only 90 minutes from the GTA! This quiet lot is located on a cul de sac in a peaceful waterfront community and is just a short walk away from deeded access to the beautiful waters of Lake Simcoe, perfect for swimming, boating and enjoying sunsets by the water. Nearby hotspots include Bayview Memorial Park offering a long stretch of sandy beach, the 28km of Oro's Rail Trail for hiking, running or biking, as well as the Line 9 boat launch for a more relaxing day on the lake. Whether you're looking to create a custom family getaway or invest in a highly desirable lakeside location, this property offers endless potential. Don't miss your chance to own a rare piece of paradise near Lake Simcoe! More detailsListed by KELLER WILLIAMS EXPERIENCE REALTY- Scott Bird
- Re/Max Crosstown
- 416-407-8074
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3 Greenwood Forest Road in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12300128
3 Greenwood Forest Road Oro-Medonte L0L 2E0
$2,395,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12300128
- Bedrooms:
- 4
- Bathrooms:
- 3
Invest in the View!! Welcome to your Lakefront Dream Home ,nestled on Greenwood Forest Road in one of Oro MEDONTE 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 Café 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 Resort. More detailsListed by PINE TREE REAL ESTATE BROKERAGE INC.- 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
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7 Lakeshore Road E in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12307983
7 Lakeshore Road E Oro-Medonte L0L 2E0
$2,299,900Residential Freehold- Status:
- Active
- MLS® Num:
- S12307983
- Bedrooms:
- 4
- Bathrooms:
- 3
South-facing, 100 ft private, level lot on Lake Simcoe with a stunning park-like setting. The beautifully enhanced waterfront features granite stonework, including elegant stairs and a reinforced shoreline. Enjoy peaceful lake views from the waterside stone patioperfect for relaxing or entertaining. The property also includes front and rear patios, surrounded by lush, professionally landscaped gardens. This charming 3+1-bedroom bungalow including a spacious 17' x 10' guest Bunkie, complete with a 3-piece bathideal for hosting friends or extended family. The open-concept interior includes a well-appointed kitchen with breakfast bar, built-in oven, microwave, and stovetop, all overlooking the large living room with a stone fireplace and breathtaking water views. Generously sized bedrooms, a dedicated office space, and a laundry room with excellent storage make this home as practical as it is beautiful. Conveniently located midway between Barrie and Orillia for easy access to shopping and amenities, and just minutes from Simcoe Loop Trail (walking, biking, running etc), skiing, and golf. More detailsListed by RE/MAX HALLMARK CHAY REALTY- Scott Bird
- Re/Max Crosstown
- 416-407-8074
- Contact by Email
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47 Eight Mile Point Road in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12342310
47 Eight Mile Point Road Oro-Medonte L3V 6H1
$3,390,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12342310
- Bedrooms:
- 5
- Bathrooms:
- 4
On a quiet, tree-lined crescent, this turnkey brick bungalow offers an exceptional lifestyle on one of Lake Simcoes most sought-after stretches of shoreline. 5 bedrooms, 4 bathrooms & a beautifully renovated bunkie above the single-slip boathouse, lakeside living at its finest.Professionally landscaped front and back with lush perennials, a full irrigation system. Engineered hardwood throughout the main floor. Kitchen with quartz countertops, Thermador WiFi-enabled gas range, pot filler & premium finishes. Living room with gas fireplace & dining area with walkout to a sprawling 75-ft deck (gas BBQ hookup)overlooking the lake - perfect for entertaining. Main floor primary features a luxurious ensuite with heated floors, large walk-in shower, Bluetooth in-wall speaker, in-suite laundry hook-up & a private walkout with water views. Two additional main floor bedrooms share a 4-piece bath.Recreation room with fireplace & walkout to a private hot tub area overlooking the water. Wet bar with fridge and dishwasher. 2nd primary with fireplace, built-ins, water views, walkout access & an opulent ensuite featuring a soaker tub on a solid walnut base, heated floors, double vanity & glass shower. Additional 5th bedroom, 2-piece powder room, laundry room, 6-person sauna with separate shower & mudroom with built-in dog bath. Renovated bunkie above the 26' x 12' boathouse, complete with kitchen & 3-piece bath ideal for guests "who won't want to leave. Marine railway to the boathouse. Waterside 10' x 19' deck, concrete stairs, break wall & 100 of clean, hard-bottom pebble shoreline with approximately 5 feet of depth off the dock with hard bottom sand perfect for swimming & water activities. Association dues include access to 62 acres of private parkland with nature trails for walking, cross-country skiing, etc & two waterfront tennis courts. Minutes to the Simcoe Rail Trail for biking, running, walking, or snowmobiling. Close to Orillia for amenities. 1 hour to the GTA. More detailsListed by RE/MAX HALLMARK CHAY REALTY- 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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43 Moon Point Drive in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12364088
43 Moon Point Drive Oro-Medonte L3V 0R8
$1,649,900Residential Freehold- Status:
- Active
- MLS® Num:
- S12364088
- Bedrooms:
- 5
- Bathrooms:
- 3
Welcome to Moon Point A Rare Waterfront Opportunity! This stunning point-lot property with North-East exposure offers 106 feet of shoreline, complete with a boathouse (roller door with remote) and marine railway (with remote), ideal for boating enthusiasts. Enjoy panoramic water views from three sides of the cottage and take in both sunrises and sunsets from this uniquely positioned retreat. Inside, youll find five spacious bedrooms and three bathrooms, perfect for hosting family and friends. The home is turn-key with a newer kitchen, bathrooms, floors, ceilings, lighting, and moreready for immediate enjoyment. Working remotely? This property is optimized for productivity with high-speed internet (500+ MB down and 50MB+ up) and multiple flexible spaces for a home office setup. Step outside to crystal-clear water with a firm bottom and ample depth for swimming and boating. The private point location offers peace and seclusion, while still being minutes to Orillias shops, dining, and services. Located on a quiet, walkable road, near the rail trail for hiking and biking, and close to golf courses and ski hills, this four-season property has it all. Bonus: excellent year-round access with city snow removal thanks to its position on a school bus route. Dont miss your chance to own this exceptional waterfront getaway! More detailsListed by RE/MAX HALLMARK CHAY REALTY- Scott Bird
- Re/Max Crosstown
- 416-407-8074
- Contact by Email
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9 Beach Road in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12372775
9 Beach Road Oro-Medonte L3V 0R9
$545,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12372775
This private waterfront lot on Bass Lake has been partially cleared and is located minutes west of Orillia and 75-minutes from the GTA. Build your dream home in a peaceful, treed, natural setting with wildlife and water fowl in abundance. The property has east/northeast exposure and is located at the end of a cul-de-sac turn around, adjacent to a pedestrian entrance near the south side of Bass Lake Provincial Park. The lot has had significant shoreline improvements that include a sheet pile retaining wall spanning the width of the property, a covered wet-slip supported by steel pillars, a channel dredged in front of the wet-slip and a permanent concrete & aluminum framed dock ready for your finishing touches. Beach Road is a private road that is maintained by the township with winter snow removal and garbage/recycling available. This property is being sold 'AS IS' by a non-occupying estate trustees with no representations or warranties. Easy to show. Offers considered any time. More detailsListed by RE/MAX RIGHT MOVE- Scott Bird
- Re/Max Crosstown
- 416-407-8074
- Contact by Email
Data was last updated October 16, 2025 at 05:15 PM (UTC)
RE/MAX Crosstown
Office Address:
566 Bryne Dr., Unit A
Barrie, ON, L4N 9P6