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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31 Grandview Crescent in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13711800
31 Grandview Crescent Oro-Medonte L0L 2E0 
$1,890,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13711800
- Bedrooms:
- 6
- Bathrooms:
- 3
Experience exceptional waterfront living in this beautifully updated home in a prime location of Oro-Medonte, offering panoramic lake views from almost every room and over 100 feet of private dockage with a breakwall seating area. Nestled on a quiet crescent with walkable beach access, this property combines luxury, comfort, and an unbeatable lakeside lifestyle. Featuring 5 Bedrooms + Den, with lake views from 4 of the bedrooms, this spacious home is designed to maximize its stunning setting. The attached oversized double-car garage provides convenient basement access, while the expansive driveway accommodates up to 8 vehicles. The outdoor living space is designed for relaxation, offering a new deck, hot tub, and fire pit seating area, all positioned to take full advantage of the stunning lake views. The bright and inviting interior has been extensively upgraded, including a fully renovated primary ensuite with a Schluter waterproofing system, oversized walk-in shower, and in-floor heating (2019). The upper-level family bathroom was also renovated with a Schluter system, and luxury vinyl flooring was installed throughout the upper level (2022). The kitchen features updated wall tile, upgraded lighting and electrical, and in-floor heating for year-round comfort (2019)Recent improvements include four new windows (2020), a new deck (2025), and upgrades to the hydronic heating system with a new motor and major components (2025). Additional highlights include a fenced lakeside yard, double access to the basement and armour stone driveway wall (2017). With breathtaking waterfront views throughout the home this is a rare opportunity to own a meticulously maintained waterfront property offering privacy, modern upgrades, and spectacular scenery. This is a MUST SEE home!!! More detailsListed by KINGDOM HOMES REALTY INC.- Scott Bird
- Re/Max Crosstown
- 416-407-8074
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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.- Scott Bird
- Re/Max Crosstown
- 416-407-8074
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2295 Lakeshore Road E in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12957458
2295 Lakeshore Road E Oro-Medonte L0L 1T0
$1,398,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12957458
- Bedrooms:
- 3
- Bathrooms:
- 2
Gorgeous south east views of Lake Simcoe sitting on the edge of Carthew Bay. This well cared for waterfront gem is ready to be your year round sanctuary. 60' of water frontage, located less than 15 minutes to Orillia for shopping, 25 mins to Barrie and an hour from the GTA, access and convenience is second to none. This home can be an ideal weekend retreat, or for those who cherish waterfront living, an all year round home. Bask in the sun on the 4'x45' + 8'x10' aluminum fixed dock with composite boards. Extensive hardscaping with armour stone at the rear of the lot leading down to the waterfront and multiple decks/patios to choose from. Full finished walk out basement containing finished rec room, two bedrooms and a 3 piece bath. Appliances included. Seller is Registered Sales Person New furnace and AC 2018, new HW tank 2024, new roof 2019, new septic 2017, new electrical panel 2023 More detailsListed by EXP REALTY- Scott Bird
- Re/Max Crosstown
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2533 Ridge Road W in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13123868
2533 Ridge Road W Oro-Medonte L0L 2L0
$15,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13123868
- 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, southfacing 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
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2683 Lakeshore Road E in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13137936
2683 Lakeshore Road E Oro-Medonte L0L 1T0
$2,100,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13137936
- Bedrooms:
- 3
- Bathrooms:
- 3
"Welcome to your private lakeside retreat on the serene shores of Carthew Bay. Perfectly positioned to capture Muskoka-like views, this exceptional waterfront property offers a rare opportunity to enjoy pristine waters with a clean hard rock and sandy shoreline, creating the ultimate year-round escape. Situated on a pool-size lot, this completely renovated and remodelled turnkey bungalow blends modern comfort with effortless waterfront living. The home offers a warm and inviting atmosphere with a custom eat-in kitchen with all granite worktops and stunning water views, while the dining room overlooks the sparkling lake and opens directly onto a spacious deck perfect for entertaining or relaxing in the tranquil surroundings.The open-concept living spaces are enhanced by expansive windows that frame spectacular lake views and fill the home with natural light.Step directly onto the oversized deck where morning coffee becomes part of your daily routine and enjoy new-moon views reflecting on the lake.Outside, a natural slope gracefully leads to the water and a private dock and boathouse offering easy access to boating, paddle boarding, fishing, and endless waterfront enjoyment.Additional space on the lower level provides the perfect area for guests,grandchildren, or extended family, adding to the property's versatility and appeal.Located in a quiet and friendly neighbourhood,this remarkable property offers the perfect balance of peaceful lakeside living and convenience,with easy access to Highway 11, just 10 minutes to Orillia and just over an hour to Toronto.Public boat launching,walking,hiking,and biking trails are all nearby,making this an ideal destination for outdoor enthusiasts and those seeking a private waterfront paradise.This is more than a home - it's a lifestyle where every day feels like a vacation.Come home to your special refuge and start a new chapter of lakeside living at this signature address on beautiful Lake Simcoe." More detailsListed by HOUSSPRO DL REALTY- Scott Bird
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1174 15 Line N in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13151618
1174 15 Line N Oro-Medonte L3V 8C6
$1,299,900Residential Freehold- Status:
- Active
- MLS® Num:
- S13151618
- Bedrooms:
- 5
- Bathrooms:
- 2
Rare opportunity to own a west facing, waterfront home on sought-after Bass Lake. Situated on a generous lot with 40 ft of sandy shoreline, this property offers excellent swimming, boating, and year-round recreation. Enjoy stunning lake views and breathtaking sunsets from your own dock or the glass-railed deck.The open-concept main floor features a kitchen overlooking the sunken living room, ideal for entertaining. The upper level offers 2 bedrooms, including a spacious primary suite with walk-in closet and jacuzzi tub. The finished lower level includes 3 additional bedrooms, a rec room, 3-piece bath, separate entrance, and large lake-view windows; perfect for guests or potential in-law suite. Further features include energy efficient construction with ICF foundation and exterior walls, in-floor radiant heating, thermal pane casement windows, gas stove, attached heated garage with loft storage, updated roof, landscaped gardens, fenced yard, shed, and water treatment system. Located steps from Bass Lake Provincial Park with access to swimming, boating, snowshoeing, and cross-country skiing. *Some photos have been digitally staged to showcase potential* More detailsListed by RE/MAX RIGHT MOVE- Scott Bird
- Re/Max Crosstown
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17 Stanley Avenue in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13433188
17 Stanley Avenue Oro-Medonte L0L 1T0
$1,049,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13433188
- Bedrooms:
- 2
- Bathrooms:
- 2
EXCEPTIONAL LAKE SIMCOE ESCAPE WITH 50 FT OF SHORELINE SERENITY, PRIVATE DOCK ACCESS, & AN AIRY OPEN-CONCEPT DESIGN! 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. 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
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209 Bay Street in Oro-Medonte: Shanty Bay House for sale : MLS®# S13508726
209 Bay Street Oro-Medonte L0L 2L0
$4,490,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13508726
- Bedrooms:
- 5
- Bathrooms:
- 5
Rare Waterfront Estate in Prestigious Shanty BayA rare opportunity to own an exceptional waterfront retreat in the heart of Shanty Bay. Tucked away on a quiet dead-end street, this remarkable property offers nearly 200 feet of pristine, south-facing shoreline on Kempenfelt Bay, with crystal-clear deep water ideal for swimming, boating, and enjoying breathtaking panoramic views.Set on a private, beautifully treed lot, the estate includes a main cottage, guest house, and bunkie above the garage, providing a total of 12 bedrooms, 8 bathrooms, and 3 kitchens. With ample space for extended family, guests, or potential rental income, this property offers outstanding versatility.Most principal rooms capture stunning lake views, while the outdoor spaces are designed to embrace waterfront living. Features include a lakeside concrete patio, marine railway with covered boat slip, and a spacious rooftop deck above the boathouse-perfect for entertaining and enjoying spectacular sunsets.The main cottage is filled with warmth and character, featuring hardwood floors, a stone fireplace, a charming Muskoka room overlooking the water, and a cozy third-level loft retreat.Additional highlights include a heated garage with bunkie accommodation above, parking for 10+ vehicles, and a secluded, park-like setting surrounded by mature trees for exceptional privacy.Conveniently located just 10 minutes from Barrie, Royal Victoria Regional Health Centre, shopping, dining, and everyday amenities, and approximately one hour from Toronto. Enjoy easy boat access to Friday Harbour Resort and nearby recreational trails.Whether enjoyed as a private family compound, multi-generational getaway, or investment opportunity with future severance or redevelopment potential, this is a rare chance to own a legacy waterfront property in one of Lake Simcoe's most coveted communities. More detailsListed by RE/MAX HALLMARK CHAY REALTY- Scott Bird
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6 Orillia Road in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13551310
6 Orillia Road Oro-Medonte L0L 2E0
$499,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13551310
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 lake 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
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2289 Lakeshore Road E in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13594762
2289 Lakeshore Road E Oro-Medonte L0L 1T0
$1,690,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13594762
- Bedrooms:
- 3
- Bathrooms:
- 3
Enjoy 60 feet of crystal-clear Lake Simcoe waterfront with a shallow, rocky shoreline, ideal for swimming, boating, and family fun. Perfectly positioned to capture stunning eastern views across the lake and picturesque Carthew Bay to Eight Mile Point, this inviting waterfront home offers the ideal setting for year-round living or a relaxing cottage retreat. This spacious two-storey home features 3 bedrooms and 2 full bathrooms, with bright, open living spaces designed for entertaining. The generous living and dining rooms easily accommodate family gatherings, while a convenient 2-piece powder room is located on the main level. The heart of the home is the open-concept eat-in kitchen, complete with stainless steel appliances, a centre island with breakfast bar, and seamless flow into the family room, where a cozy gas fireplace and expansive lake views create the perfect place to unwind. Step through the walkout to the large lakeside deck, an ideal space for outdoor dining, entertaining, or simply enjoying the peaceful waterfront setting. Practical features include direct access from the attached garage into the laundry/mudroom with abundant storage cabinetry, along with hardwood flooring throughout most of the main floor. Upstairs, the spacious primary suite offers a 3-piece ensuite and private walkout to a lakeside deck-the perfect spot to enjoy your morning coffee while watching the sunrise over the water. The second bedroom also shares access to the deck, while a third bedroom and a 4-piece bathroom complete the upper level. Outside, you'll appreciate the low-maintenance metal roof and concrete double driveway. The lakeside yard provides plenty of room for children to play, while easy access to the shoreline and a generous dock make it effortless to enjoy everything Lake Simcoe has to offer. Located minutes from Orillia's shopping, restaurants, and hospital, and an easy walk or bike ride to the Simcoe Loop Trail combining lakeside living with everyday convenience. More detailsListed by RE/MAX HALLMARK CHAY REALTY- Scott Bird
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1189 Woodland Drive in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13607388
1189 Woodland Drive Oro-Medonte L3V 0R8
$2,999,900Residential Freehold- Status:
- Active
- MLS® Num:
- S13607388
- Bedrooms:
- 4
- Bathrooms:
- 4
Some properties offer waterfront. Others offer a lifestyle that simply can't be replicated. From the curb appeal to the breathtaking lake views the moment you step inside, this is a home designed to be experienced. Along the shores of Lake Simcoe in Oro-Medonte, this luxury waterfront home offers peaceful lakeside living just 10 min from the amenities of Orillia. Rich in arts, culture, waterfront parks, dining & year-round events, putting the best of city conveniences & small-town charm just minutes from your doorstep. Every inch of 1189 Woodland Drive has been shaped with a commitment to premium materials & enduring craftsmanship. Redesigned in 2022, the thoughtfully re-imagined floor plan blends timeless design with modern comfort. Extensive upgrades & carefully selected finishes elevate this home well above the ordinary, including multiple heating zones. The open-concept main living area was designed to maximize the panoramic lake views, anchored by a beautifully appointed chef's kitchen at the heart of the home. A fully finished walkout lower level with a self-contained in-law suite offers outstanding flexibility for multi-generational living or guests. Outside, multiple outdoor living spaces embrace every aspect of waterfront living. Relax on the waterside patio, entertain on expansive decks, gather around the outdoor gas fireplace, unwind on the rooftop patio atop the rare double boathouse, or spend the day on the lake from your private dock. The sheltered shoreline provides calmer conditions and a more comfortable outdoor experience throughout the season. With over 100ft of private Lake Simcoe shoreline, extensive updates, a whole-home generator & finished walkout lower level, this property offers a truly distinctive waterfront setting. The combination of location, atmosphere & design must be experienced in person. This is more than a waterfront home-it's a lifestyle defined by luxury, connection to the water & memories waiting to be made. More detailsListed by RE/MAX RIGHT MOVE- Scott Bird
- Re/Max Crosstown
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15 Stanley Avenue in Oro-Medonte: Rural Oro-Medonte House for lease : MLS®# S13608476
15 Stanley Avenue Oro-Medonte L0L 1T0
$5,500Residential Freehold- Status:
- For Lease
- MLS® Num:
- S13608476
- Bedrooms:
- 3
- Bathrooms:
- 4
Welcome to this newly built waterfront home in the tranquil community of Hawkstone. Boasting 3bdrms + den and 4 bathrooms, all hardwood floors thru-out and fully finished lower level with walk-out to the backyard overlooking lake Simcoe. Featuring family room with floor to ceiling windows (20ft high ceiling) and gas fireplace, dining area combined with living room, breakfast area with walk-out to the balcony, master bedroom with 5pc ensuite and Juliette balcony, large interlocking patio. Few minutes away from picturesque Bayview Memorial Park. Great location offering year round activities, like swimming, fishing, ice-skating and ice fishing from your private dock. More detailsListed by CENTURY 21 PARKLAND LTD.- Scott Bird
- Re/Max Crosstown
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Data was last updated September 9, 2026 at 04:15 AM (UTC)
RE/MAX Crosstown
Office Address:
566 Bryne Dr., Unit A
Barrie, ON, L4N 9P6