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.- Scott Bird
- Re/Max Crosstown
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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
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13 Pemberton Lane in Oro-Medonte: Shanty Bay House for sale : MLS®# S12689286
13 Pemberton Lane Oro-Medonte L0L 2L0
$3,199,999Residential Freehold- Status:
- Active
- MLS® Num:
- S12689286
- Bedrooms:
- 4
- Bathrooms:
- 2
Rare opportunity to own an original log home on one of Kempenfelt Bay's most prestigious private roads, neighbouring some of the area's most notable luxury waterfront estates. Set on approximately 100 feet of prime, south-facing waterfront, this property enjoys all-day sun and stunning sunrise views over the bay.The interior showcases the preserved original log construction, complemented by soaring high ceilings, original wood flooring, and skylight windows that flood the home with natural light while enhancing its authentic character. The four-bedroom, open-concept layout offers inviting living spaces ideal for both everyday living and entertaining.Enjoy exceptional lake life with a waterside sitting area and new dock, providing direct access for boating, swimming, and all Lake Simcoe amenities. Located in the highly sought-after Shanty Bay area of Oro-Medonte, just 10 minutes to shopping, dining, and Highway 400. Approximately one hour to Toronto, one hour to Muskoka, and 30 minutes to premier skiing. Situated on the Trans Canada Rail Trail, ideal for walking, hiking, and biking, with water access to downtown Barrie and Friday Harbour Resort and marina.A rare opportunity to enjoy as-is, renovate, or rebuild in one of Kempenfelt Bay's most coveted waterfront settings. More detailsListed by HARVEY KALLES REAL ESTATE LTD.- Scott Bird
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167 Lakeshore Road W in Oro-Medonte: Shanty Bay House for sale : MLS®# S12726808
167 Lakeshore Road W Oro-Medonte L0L 2E0
$2,045,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12726808
- Bedrooms:
- 2
- Bathrooms:
- 2
What a treat! Delightful home, meticulously cared for. Custom Designed Kitchen with top quality Cambria Counters. Jennair Gas Range, built in double oven and terrific breakfast bar (Ideal for guests while entertaining & chef duties are happening)... that makes me think of the handy wine fridge.! Spacious dining area, suitable for large table & vaulted ceiling adds drama... flowing beautifully to the sunken living room, with built-in cabinets and cozy gas fireplace. All of this with gorgeous view of the sparkling sun on the water. (Isn't that what lakefront living is all about?) Main floor Primary Bedroom offers convenient privacy and another amazing view of the lake...along with a walkout to the deck and waterfront. The Primary Ensuite is awesome, heated floors, stand-alone tub, glass shower...just so nice! Then the large walk-in closet is perfectly positioned and well suited to handle your wardrobe. The main floor laundry and garage entrance make for handy access and convenience. Walk up the hardwood stairs, across the loft view over the great living areas and find a private bedroom area, with it's own 4pc ensuite (heated floors, no less). The waterfront is easy access, gently sloping with a terrific dock system (composite surface) approx 60ft long. Now, you can't miss the gracious size and high ceiling in the amazing sun room (very adjustable windows & screens) which can extend your enjoyment so much of the year. The Vieto Radiant heaters and custom blinds ensure you have all the comfort options you can imagine. All year long you can surely relax in the Jacuzzi Hot Tub, and there are 2 separate gas line hook-ups for BBQ etc. Worry free is a good thing, hence the full home Generac Generator is standing by at your service to ensure no interruptions...even during that dinner party, or waterfront gathering. Nice! More detailsListed by RE/MAX CROSSTOWN REALTY INC.- Scott Bird
- Re/Max Crosstown
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1 Sunnyside Avenue in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12763190
1 Sunnyside Avenue Oro-Medonte L0L 2E0
$3,399,998Residential Freehold- Status:
- Active
- MLS® Num:
- S12763190
- Bedrooms:
- 5
- Bathrooms:
- 4
Exceptional south-facing lakefront estate offering 4370 sq ft of fully renovated living on 100' x 194' of flat, steel-pile protected shoreline. Breathtaking water views from nearly every room. Luxury waterfront just 15 minutes from Barrie or Orillia.Thoughtfully redesigned in 2023, features two spectacular Primary Bedrooms, 1 main floor & 2nd upstairs - each with ensuite bathrooms, heated floors, separate water closets, walk-in closets, floor-to-ceiling windows opening to private Lakeview decks. The lower suite offers covered deck hot tub access, while the upper suite features a glass railing deck. The 3rd spacious upper bedroom could be split into 2, has 5 pc ensuite & heated floors. House designed for a fifth bedroom/office or fitness space upstairs, easily converted. The Show-Stopping Great Room has floor-to-ceiling glass, ceiling wood beams, Napoleon wood-burning fp w/ Owen Sound stone and custom built-in cabinets. Hardwood flooring throughout w/ luxury carpet in bedrms. The chef's kitchen offers water views, Bosch Wall Oven & Microwave, gas range, custom cabinetry, Quartz countertops & backsplash, large island for six, and dedicated coffee bar. Enclosed 3 season Sunroom with Douglas Fir floors & ceiling, Sun-Tek windows/screens, room for sitting and eating area. Inside entry from garage into family sized mud/ laundry room, dog wash & powder room. Amenities continue: UV water system, whole-home generator, automated irrigation and lighting, new septic system, lakeside patio & fire pit, dry double boathouse with dual railways, workshop, storage for water toys, new 60' dock with huge seating area. A 2-storey Detached heated/air-conditioned garage built to fit a golf simulator, second story for 5th bedroom or games room. 21' Bow-rider boat included. Refined waterfront living at its absolute best - impeccably renovated, thoughtfully designed, and built for unforgettable moments on the water. Homes of this calibre, condition, and location are rarely offered. More detailsListed by RE/MAX HALLMARK CHAY REALTY- Scott Bird
- Re/Max Crosstown
- 416-407-8074
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1125 Woodland Drive in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12769786
1125 Woodland Drive Oro-Medonte L3V 6H1 OPEN HOUSE: Apr 18, 202612:00 PM - 02:00 PM EDTOpen House on Saturday, April 18, 2026 12:00PM - 2:00PM
$1,449,900Residential Freehold- Status:
- Active
- MLS® Num:
- S12769786
- Bedrooms:
- 3
- Bathrooms:
- 2
Welcome to your private lakeside retreat, featuring 72 feet of pristine, hard-bottom and sparkling, crystal-clear water-ideal for swimming, boating, and unforgettable sunsets. This fully winterized 3-bedroom, 2-bathroom bungalow is nestled on a beautifully treed lot, offering a peaceful natural setting with uninterrupted lake views from the moment you arrive.The open-concept living area showcases new vinyl flooring, a cozy wood-burning fireplace, and a walkout to an expansive deck that extends toward the water-perfect for relaxing or entertaining just steps from the lake. The lakeside eat-in kitchen blends function and scenery, featuring stainless steel appliances including a 6-burner gas stove, fridge, and dishwasher, all complemented by panoramic shoreline views.Wake up to the beauty of the lake in the primary bedroom with ensuite. Two additional bedrooms and a full 4-piece bath provide comfortable accommodations for family or guests. The lower level offers laundry facilities and ample storage space.The true showstopper is the impressive 30' x 33' waterfront deck-an ideal setting for lakeside lounging or summer gatherings, enhanced by the gentle sounds of the water below. Enjoy the ultimate lake lifestyle with a 26.5' x 16' boathouse complete with a marine railway, perfectly suited for your boat and water toys. Above, a 29' x 18' concrete rooftop deck creates an unforgettable space for evening entertaining under the stars.This is more than a home-it's a lifestyle on the lake. More detailsListed by RE/MAX HALLMARK CHAY REALTY- Scott Bird
- Re/Max Crosstown
- 416-407-8074
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73 Parkside Drive in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12873050
73 Parkside Drive Oro-Medonte L0L 1T0
$1,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12873050
- Bedrooms:
- 4
- Bathrooms:
- 3
Lovely open concept bungalow on a 100 ft of prime waterfront and 203 ft deep lot, on quiet Parkside Drive, a short walk to Bayview Memorial Park. Large front & back yards, unobstructed views of Lake Simcoe, 4 bedrooms, 3 baths, 1788 sq ft on main, 3004 sq ft finished on 2 levels. At the water are a boathouse 24'4" x 12'0" (9'10" wide inside), marine rail & dock, enjoy sitting on the water side deck or the upper deck of the boathouse with glass railings. Beautifully renovated both upstairs and down with stylish kitchen, dining & living room with stone fireplace center piece, all with amazing views of the water. Updated bedrooms & baths as well. It all shows to perfection up & down. Find a gas fireplace down as well, with a nice family room, office & storage alongside the bedroom & bath. Spacious main floor laundry, inside entrance from an oversized double garage with a 6+ car driveway. Well maintained & updated: windows, doors & garage doors, furnace & air conditioner, deck, front tumble stone walkway and driveway have been replaced. There is a shed, 10kw backup generator, hot tub, central vac & UV filter, extra spray foam insulation, cable & high speed internet..... Pride of Ownership. More detailsListed by ROYAL LEPAGE FIRST CONTACT REALTY and Royal LePage Locations North- Scott Bird
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209 Bay Street in Oro-Medonte: Shanty Bay House for sale : MLS®# S12875984
209 Bay Street Oro-Medonte L0L 2L0 OPEN HOUSE: Apr 19, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, April 19, 2026 2:00PM - 4:00PM
$4,799,900Residential Freehold- Status:
- Active
- MLS® Num:
- S12875984
- Bedrooms:
- 5
- Bathrooms:
- 5
A rare opportunity to own a true waterfront retreat in the heart of Shanty Bay. Tucked away on a quiet dead-end street, this exceptional lakefront property boasts nearly 200 feet of pristine, south-facing shoreline with crystal-clear, deep water-perfect for swimming, boating, and enjoying breathtaking panoramic views across Kempenfelt Bay.Set on a beautifully treed and private lot, this remarkable estate features a main cottage, guest house, and a bunkie above the garage, offering a total of 12 bedrooms, 8 bathrooms, and 3 kitchens. Whether hosting extended family, entertaining guests, or exploring rental income opportunities, there is ample space for everyone.Most principal rooms capture stunning, unobstructed lake views, while the outdoor living spaces are designed to make the most of the waterfront lifestyle. Enjoy a private concrete lakeside patio, a marine railway with covered boat slip, and an expansive rooftop deck above the boathouse-an ideal setting for sunset entertaining.The main cottage is filled with warmth and character, featuring wood floors, a charming stone fireplace, a Muskoka room with spectacular water views, and a cozy third-level loft retreat.Additional highlights include a heated garage with bunkie above, parking for 10+ vehicles, and a secluded, park-like setting surrounded by mature trees for exceptional privacy.All of this is located just 10 minutes from Barrie, Royal Victoria Hospital, shops, and services, and only an hour from Toronto. Enjoy quick boat access to Friday Harbour's dining and amenities, or explore the nearby Simcoe Loop Trail for scenic walking and cycling.Whether you choose to enjoy this special property as it is, or explore its future severance or redevelopment potential, this is a once-in-a-lifetime opportunity to own a legacy lakefront estate in one of Lake Simcoe's most sought-after communities. More detailsListed by RE/MAX HALLMARK CHAY REALTY- Scott Bird
- Re/Max Crosstown
- 416-407-8074
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1189 Woodland Drive in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12885716
1189 Woodland Drive Oro-Medonte L3V 0R8
$3,289,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12885716
- Bedrooms:
- 4
- Bathrooms:
- 4
FOR THE SELECTIVE BUYER: Over 100ft of south-east Lake Simcoe waterfront & 3890 sq ft of exceptional multi-generational flexibility. Remarkable remodel since 2022 guided by thoughtful planning & supported by an updated survey, the result is a seamless modern, sophisticated lakefront retreat minutes to Orillia & Hwy 11. A high-end custom home is evident from curb appeal of the new covered front porch to opening the front door. Designed for waterfront living, all principal rooms are waterside & walls of glass capture panoramic lake views. Private & serene lot naturally protected from prevailing winds. Striking open riser custom staircase makes an architectural statement while a stunning three-sided DaVinci fireplace elegantly defines living & dining spaces preserving an open-concept flow. Beauty & performance, the kitchen showcases solid maple cabinetry, premium hardware, a 10-ft quartzite island, Built-in 36" gas Café apron-front range, Bosch wall oven w/ microwave/speed/convection functionality, Built-in refrigerator w/ double freezers, ice maker, filtered water, dedicated coffee bar w/ bar sink & beverage fridge. Primary suite features spa-inspired en-suite bath, large walk-in closet & a private deck/glass railings w/unobstructed water views. Secondary bedrooms w/custom maple built-ins, a gorgeous bath & upper laundry. Work from home w/ 2 dedicated offices for a busy lifestyle. Finished walkout featuring gorgeous self-contained waterside in-law suite w/exquisite features & separate laundry. On-demand water, multiple water filtration systems, gas heat & standby generator offer the best in comfort. Outdoor showcases impressive 70ft dock + 20' x 20' sitting area w/southerly views. Main floor deck is 45'x16', trex decking, glass railings, & hookups for BBQ & fire table & 16x16 covered space. Rare double boathouse w/rooftop patio anchors the waterfront for extraordinary vantages & lakeside relaxation. 3-car garage + workshop plumbed w/water & heat for gym/hobby room. More detailsListed by RE/MAX RIGHT MOVE- Scott Bird
- Re/Max Crosstown
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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
$1,445,000Residential 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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7 Lakeshore Road E in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12963020
7 Lakeshore Road E Oro-Medonte L0L 2E0 OPEN HOUSE: Apr 18, 202602:30 PM - 04:30 PM EDTOpen House on Saturday, April 18, 2026 2:30PM - 4:30PM
$2,149,900Residential Freehold- Status:
- Active
- MLS® Num:
- S12963020
- Bedrooms:
- 4
- Bathrooms:
- 3
One hundred feet of level shoreline along the South-facing shores of Lake Simcoe. This exceptional property offers a truly picturesque, private, park-like setting. The thoughtfully enhanced waterfront showcases beautiful granite stonework, complete with elegant stairs and a reinforced shoreline-perfectly designed for both beauty and function. Unwind or entertain on the stunning waterside stone patio while taking in serene, panoramic lake views.Surrounded by lush, professionally landscaped gardens, the home also features inviting front and rear patios that create multiple outdoor living spaces to enjoy throughout the day.This charming 3+1 bedroom bungalow includes a spacious 17' x 10' guest bunkie with its own 3-piece bath-ideal for hosting family and friends in comfort and privacy.Inside, the open-concept layout is designed to capture the views, with a well-appointed kitchen featuring a breakfast bar, built-in oven, microwave, and stovetop, all overlooking a generous living room anchored by a striking stone fireplace and wall-to-wall water views. Spacious bedrooms, a dedicated home office, and a laundry room with ample storage add to the home's everyday functionality.Perfectly situated between Barrie and Orillia, this property offers convenient access to shopping, dining, and amenities, while being just minutes from the Simcoe Loop Trail, skiing, and golf-making it an ideal four-season retreat. More detailsListed by RE/MAX HALLMARK CHAY REALTY- Scott Bird
- Re/Max Crosstown
- 416-407-8074
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47 Moon Point Drive in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S12999798
47 Moon Point Drive Oro-Medonte L3V 0R8
$899,000Residential Freehold- Status:
- Active
- MLS® Num:
- S12999798
- Bedrooms:
- 1
- Bathrooms:
- 1
Prime Lake Simcoe Waterfront On A Sought-After Stretch Of Shoreline. Offering 100 Feet Of Pristine Shoreline With Crystal-Clear Water, Natural Rocky Shore & Hard Sandy/Rock Bottom, Ideal For Swimming, Boating & Relaxing. Whether You Choose To Update, Expand Or Build New, This Is A Rare Opportunity To Create Your Dream Lakefront Escape In An Area Known For Luxury Redevelopment. The Existing Cottage Provides A Starting Point, Currently Serviced By Electric Heating, With Natural Gas Available At The Street For Future Conversion. Hydro, High-Speed Internet & Septic Are Already In Place, Saving Time And Development Costs. Enjoy Peaceful Surroundings Just Minutes To Orillia's Amenities, Restaurants & Hospital. Invest In The Location, Maximize The Potential & Bring Your Vision To Life On One Of Lake Simcoe's Most Desirable Shorelines. More detailsListed by LPT REALTY- Scott Bird
- Re/Max Crosstown
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Data was last updated April 17, 2026 at 04:15 AM (UTC)
RE/MAX Crosstown
Office Address:
566 Bryne Dr., Unit A
Barrie, ON, L4N 9P6