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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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
- Re/Max Crosstown
- 416-407-8074
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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
- Re/Max Crosstown
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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
$1,199,900Residential 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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209 Bay Street in Oro-Medonte: Shanty Bay House for sale : MLS®# S13508726
209 Bay Street Oro-Medonte L0L 2L0 OPEN HOUSE: Oct 25, 202612:00 PM - 02:00 PM EDTOpen House on Sunday, October 25, 2026 12:00PM - 2:00PM
$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
$475,000Residential 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
- Re/Max Crosstown
- 416-407-8074
- Contact by Email
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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
- Re/Max Crosstown
- 416-407-8074
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47 Moon Point Drive in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13690360
47 Moon Point Drive Oro-Medonte L3V 0R8
$749,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13690360
- Bedrooms:
- 2
- Bathrooms:
- 1
The Lot. The Location. The Lake. Prime Lake Simcoe Waterfront On A Sought-After Stretch Of Shoreline, Offering Over 100 Feet Of Pristine Frontage With Crystal-Clear Water, Natural Rocky Shoreline, And A Hard Sandy/Rock Bottom Ideal For Swimming, Boating, And Enjoying Lake Life. Whether You Choose To Enjoy The Existing Cottage, Renovate, Expand, Or Build New, This Property Presents An Opportunity To Create Your Ideal Lakefront Retreat In An Area Known For Luxury Redevelopment, With The True Value Found In The Exceptional Lot And Location. The Property Is Being Offered In Its Current Condition, With Hydro And High-Speed Internet In Place, Natural Gas Available At The Street For Future Use, And An Existing Septic System On Site. Peaceful Setting Just Minutes To Orillia For Amenities, Dining, And Hospital Access, Offering A Premium Piece Of Lake Simcoe Shoreline To Bring Your Vision To Life. More detailsListed by LPT REALTY- Scott Bird
- Re/Max Crosstown
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797 Woodland Drive in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13743864
797 Woodland Drive Oro-Medonte L3V 0R8 OPEN HOUSE: Oct 25, 202601:00 PM - 03:00 PM EDTOpen House on Sunday, October 25, 2026 1:00PM - 3:00PM
$1,850,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13743864
- Bedrooms:
- 3
- Bathrooms:
- 3
More than 110 feet of Lake Simcoe shoreline frames a home built by its current owners in 2011, designed by Kimberley Morris Interior Design and offered turnkey. Year-round dual road access leads through a wooded setting to a lot that runs flat from roadside to water. Open the front door and floor-to-ceiling windows draw the eye to one of Lake Simcoe's most picturesque expanses, where the sun comes up over the water each morning. To the left, a natural gas fireplace anchors the room. A calming, sophisticated country palette carries through more than 2,700 square feet, while the staircase sits tucked out of sight so the vaulted great room reads as one uninterrupted space. Living and dining flow to the kitchen, where family and friends remain part of everything and the large quartz island becomes a gathering place for grandkids and guests. Tucked privately to one side of the main floor, the serene primary bedroom overlooks the lake, with a spa-like ensuite: heated floors, jetted tub and glassed-in shower. Upstairs, two further bedrooms are joined by a family room and a home office. A generous mudroom with its own outdoor entrance holds laundry and extensive built-in storage. From the kitchen, step onto the cedar deck with its covered overhang and gas line for barbecuing in any season. Beyond is a broad lawn with room for games and gatherings, easing down to a shallow, sheltered bay - rocky at the shoreline, sandy beyond and wadable from shore. A seasonal irrigation line draws from the lake to water the gardens and yard, separate from the drilled well that serves the home. Woodland Drive is a street where properties seldom come available. Privacy and serenity are part of it; so is a real sense of community. Orillia is minutes away for shopping, dining and services, with golf and skiing close by. Exceptionally well built, timeless, and ready as it stands. Take the key and move in. More detailsListed by EXP REALTY- Scott Bird
- Re/Max Crosstown
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2371 Lakeshore Road E in Oro-Medonte: Hawkestone House for sale : MLS®# S13746640
2371 Lakeshore Road E Oro-Medonte L0L 1T0
$1,875,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13746640
- Bedrooms:
- 3
- Bathrooms:
- 2
Welcome to this beautifully renovated bungalow, perfectly positioned on the inviting shores of 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 home's 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. Come visit and envision the lakeside memories you'll create in this serene setting. Boathouse shown is for display purposes only. Buyer to do their own due diligence. More detailsListed by ENGEL & VOLKERS BARRIE- Scott Bird
- Re/Max Crosstown
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247 Lakeshore Road W in Oro-Medonte: Hawkestone House for sale : MLS®# S13829078
247 Lakeshore Road W Oro-Medonte L0L 2E0
$5,999,500Residential Freehold- Status:
- Active
- MLS® Num:
- S13829078
- Bedrooms:
- 4
- Bathrooms:
- 5
If Lake Simcoe had a front row, this would be it. Set on 1.09 private acres along Lake Simcoe's prestigious North Shore, 247 Lakeshore Rd West pairs 91 ft of south frontage with panoramic views, inclusive of Big Bay Point, with authentic Timber Frame craftsmanship. This entire home has been masterfully re-envisioned, inside and out, evolving into 5,340 sq-ft of modern luxury living. Situated close to the waters edge, an easy few steps on cut granite stairs lead to an exceptional shoreline including a dock and natural sandy beach with gradual entry into clear waters, ideal for swimming and children. The protected bay provides calmer waters from prevailing northwest winds. The great-room ceiling rises to 28 feet showcasing ever popular wood ceilings, a majestic natural stone fireplace and towering window views. Soaring architecture adds warmth and unmistakable character, achieving panoramic views from almost every room in the home. Custom kitchen features, Cambria quartz, JennAir appliances, oversized island seating for 6, and a walk-in pantry. Vaulted ceiling bedrooms & baths simply must be experienced. An office, games room, gym, media room & covered porches all provide space for both everyday living and entertaining. Outside is a custom concrete pool with a motorized solar/winter cover, surrounded by Brazilian walnut decking (IPE), a large flagstone terrace, hot tub and a linear natural gas fire feature. Upgraded granite shoring extends along the waterfront. A 58-ft cedar topped galvanized dock extends out into your uncommon water lot ownership. An oversized luxurious heated 4-car garage with professional epoxy flooring is a car lovers dream with TV & sound system. Whole home Generac generator, 3 zone HVAC, Sonos audio throughout, commercial grade property-wide cameras and Wi-Fi. This caliber of waterfront would be exceptionally difficult to replicate as the acreage, architecture, finishings, privacy, southern exposure & truly outstanding shoreline are a rare find. More detailsListed by CENTURY 21 B.J. ROTH REALTY LTD.- Scott Bird
- Re/Max Crosstown
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1125 Woodland Drive in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13847482
1125 Woodland Drive Oro-Medonte L3V 6H1 OPEN HOUSE: Oct 25, 202602:30 PM - 04:30 PM EDTOpen House on Sunday, October 25, 2026 2:30PM - 4:30PM
$1,349,900Residential Freehold- Status:
- Active
- MLS® Num:
- S13847482
- Bedrooms:
- 3
- Bathrooms:
- 2
Welcome to your own private waterfront retreat, where 72 feet of pristine shoreline and crystal-clear, hard-bottom water create the perfect setting for swimming, boating, fishing, and breathtaking sunrises. Nestled among mature trees, this fully winterized 3-bedroom, 2-bathroom bungalow offers exceptional privacy and spectacular lake views from the moment you arrive.The bright, open-concept interior is designed to showcase the waterfront setting, with new vinyl flooring, expansive windows, and a cozy wood-burning fireplace creating a warm and inviting atmosphere. A walkout leads to the impressive lakeside deck, making indoor-outdoor living and entertaining effortless. The eat-in kitchen overlooks the water and features stainless steel appliances, including a 6-burner gas stove, refrigerator, and dishwasher.Wake up to tranquil lake views from the spacious primary bedroom, complete with a private ensuite. Two additional bedrooms and a 4-piece bathroom provide comfortable accommodations for family and guests, while the lower level offers convenient laundry and plenty of storage.Outside, the lake lifestyle truly shines. The expansive 30' x 33' waterfront deck is perfect for entertaining, relaxing, and enjoying the spectacular surroundings. The 26.5' x 16' boathouse with marine railway provides excellent convenience for boating enthusiasts, while the 29' x 18' concrete rooftop deck offers an incredible space for morning coffee, sunrise gatherings, or evenings beneath the stars.Whether you're looking for a year-round home or the perfect four-season cottage, this exceptional property offers a rare opportunity to embrace waterfront living at its finest. Move in, relax, and start creating unforgettable memories on the lake. More detailsListed by RE/MAX HALLMARK CHAY REALTY- Scott Bird
- Re/Max Crosstown
- 416-407-8074
- Contact by Email
Data was last updated October 25, 2026 at 06:15 AM (UTC)
RE/MAX Crosstown
Office Address:
566 Bryne Dr., Unit A
Barrie, ON, L4N 9P6