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$37,000,000
8 Beds ⋅ 11 Baths ⋅ S6655772 MLS® #
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.

1775 Ridge Road W, Oro-Medonte

Listing courtesy of RE/MAX HALLMARK YORK GROUP REALTY LTD..

$24,000,000
S13502654 MLS® #
* APPROVED REDEVELOPMENT *WATERFRONT*EQUESTRIAN Set Within The Coveted Stretch Known As "Millionaires Row". Unlock The Full Potential Of Casa Lago Estate. Comprising Three Separately Titled Parcels With Dual Road Frontage And Four Gated Access Points. A Truly Exceptional, Permit-Ready Offering With Approved Plans Already In Place, Allowing You To Begin Building Your Dream Lakefront Estate Without Delay. Elevate The Property With A Spectacular 8,000-14,000 Sq. Ft. plus, Main Waterfront Residence, Complemented By An Guest House, Lakeside Pool, And An Impressive Three-Bay Boathouse-Excavation Completed-Featuring Second-Storey Storage Space And A Wrap-Around Deck. PLUS Two Stable Buildings, 8400 Sqft Indoor Riding Arena, 2400 Sqft Equipment Building. A Rare Opportunity To Own One Of The Most Significant Private Holdings Just 45 Minutes North Of Toronto. This Extraordinary 37-Acre Waterfront Estate Offers Over 515 Feet Of Pristine Shoreline Along The Prestigious Shores Of Kempenfelt Bay On Lake Simcoe. Framed By Mature Landscapes And Accessed Through Grand Private Gated Entrance, The Property Delivers A Remarkable Sense Of Scale, Privacy, And Natural Beauty. Including A Dedicated Service Entrance And Private Stable Access-This Estate Offers Unparalleled Flexibility For Customization, Expansion, Or Multigenerational Living. A True Legacy Property In One Of Ontario's Most Exclusive Waterfront Enclaves, Casa Lago Estate Represents A Seamless Blend Of Vision, Scale, And Readiness-An Unmatched Opportunity To Create A World-Class Lakefront Estate.

21 Pemberton Lane, Oro-Medonte

Listing courtesy of RE/MAX REALTRON BARRY COHEN HOMES INC..

$16,995,000
5 Beds ⋅ 8 Baths ⋅ S13567726 MLS® #
A contemporary waterfront masterpiece overlooking the turquoise waters of Georgian Bay & spectacular sunsets. Designed by acclaimed architect Richard Wengle built by Big East Construction, this rare Mountain Modern estate sits on 4.61 private acres with 234 ft of pristine Georgian Bay shoreline. Completed in 2023, the residence offers over 11,000 sf of impeccably crafted living space, where timeless architecture & resort-inspired amenities come together in one of Ontario's most spectacular waterfront settings. Soaring walls of glass blur the boundary between indoors & out, bringing the turquoise waters of Georgian Bay into every principal room. Natural Eramosa limestone, warm wood ceilings, structural steel, expansive glazing create a refined yet welcoming atmosphere, while the home's coveted western exposure delivers breathtaking sunsets as part of everyday living. Thoughtfully designed for entertaining, wellness & working from home, the residence includes a waterfront office overlooking Georgian Bay & the collector's garage, while the walkout lower level offers a golf simulator, home theatre, fitness studio, soaking bathtubs, steam showers, and generous gathering spaces. Outdoor living is equally impressive, featuring a saltwater pool, hot tub, fully equipped outdoor kitchen, glass-walled sauna, cold tub, multiple lounge areas & generous spaces for dining and entertaining - creating the feel of a private waterfront resort. A rare highlight is the impressive heated collector's pavilion accommodating six vehicles, complemented by an additional heated two-car garage. A 210 ft pier system with three boat lifts provides exceptional access to Georgian Bay. Located within the prestigious Thunder Beach community, residents enjoy exclusive access to private golf course, tennis, pickleball courts, private marinas, children's programs, & an active social club, while nearby Awenda Provincial Park offers kilometres of hiking & cycling trails, beaches & outdoor recreation.

240 Silver Birch Drive, Tiny

Listing courtesy of HARVEY KALLES REAL ESTATE LTD..

$15,995,000
5 Beds ⋅ 6 Baths ⋅ S13123868 MLS® #
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.

2533 Ridge Road W, Oro-Medonte

Listing courtesy of Sotheby's International Realty Canada.

$15,800,000
9 Beds ⋅ 8 Baths ⋅ S13073314 MLS® #
Over 14 acres with 531 ft of prime frontage on Lake Simcoe. Ideally positioned-open views without being tucked into a corner, yet not overly exposed to the main lake.Featuring gourmet kitchen, great room, family room & sunroom with stunning water views. Exceptional outdoor amenities include large patio, lookout, boathouse with concrete pier, and lighted tennis court. New unfinished bunkie offers added potential.Property severed into 4 lots: main residence, boathouse lot + 2 vacant parcels. Ideal for family compound or future resale.Prestigious lakefront setting with exceptional privacy and long-term upside.

1811 Ridge Road W, Oro-Medonte

Listing courtesy of HOMELIFE GOLCONDA REALTY INC..

$14,000,000
6 Beds ⋅ 7 Baths ⋅ S12723852 MLS® #
Step into the pinnacle of luxury living with this stunning custom-built waterfront home, meticulously renovated from top to bottom with the finest finishes and attention to detail. Set against the backdrop of panoramic lake views, this architectural masterpiece offers a luxurious floor plan designed for the most discerning tastes.Floor-to-ceiling windows and doors capture the picturesque lake vistas, infusing the home with natural light and creating an atmosphere of serenity. The heart of the home, the gourmet kitchen, features top-of-the-line appliances, premium cabinetry, and expansive countertops, providing the perfect setting for culinary masterpieces and casual gatherings alike.Entertain in style in the large formal dining room, adorned with custom built-ins and offering a sophisticated backdrop for memorable dinners and celebrations. Enhancing accessibility, an elevator ensures effortless movement between levels, catering to both practicality and luxury.A three-car garage provides ample space for vehicles and storage, while ensuring convenience and security. Step outside to your private retreat, where extensive landscaping and stonework create a picturesque backdrop for relaxation and entertainment.Enjoy a swim in the pool with cascading waterfalls, unwind in the hot tub, or indulge in a friendly game on the tennis court. Pamper yourself in the sauna and steam room, catch a movie in the theater room, or work from home in the tastefully designed office with a double-sided fireplace.An open-concept layout seamlessly connects the living spaces, offering a fluid transition from the kitchen to the poolside terrace, perfect for hosting gatherings and enjoying indoor-outdoor living.

36 Pioneer Trail, Barrie

Listing courtesy of QUEENSWAY REAL ESTATE BROKERAGE INC..

$13,999,999
10 Beds ⋅ 10 Baths ⋅ N12948024 MLS® #
A rare opportunity to own one of Kempenfelt Bay's most exclusive waterfront compounds. Nestled within a sheltered private bay at the end of a quiet cul-de-sac, this extraordinary estate offers 223 ft of privately held shoreline, exceptional privacy, and uninterrupted views with protected forest across the road.Designed for multi-generational living and entertaining, the property features four distinct structures including a luxurious main residence, a fully appointed boathouse, a private apartment, and a poolside cabana. Together they offer 10 bedrooms, a bunk room accommodating 8, 11 bathrooms, 2 full kitchens, and 3 kitchenettes.The main residence showcases reclaimed antique elm flooring, a custom wrought-iron staircase, four gas fireplaces, extensive soundproofing, refined millwork, and a chef-inspired kitchen built for large gatherings. A private one-bedroom loft with full kitchen and bath provides additional accommodation.The waterfront boathouse is a rare offering, complete with living quarters, folding glass doors, double-slip wet berths, remote lifts, and expansive lakefront decking. The self-contained apartment provides complete privacy for guests, family, or staff, while the cabana features fold-away doors, a wood-burning fireplace, and panoramic views across the pool to the lake.Resort-style grounds include a Betz Gunite infinity-edge pool, waterfall, integrated hot tub, covered and open-air entertaining areas, BBQ pavilion, stone terraces, frameless glass railings, and a permanent dock. Every detail has been thoughtfully designed to maximize the connection to the water.A truly generational estate combining protected bay frontage, exceptional privacy, and an unmatched family compound setting-just one hour from Toronto and worlds away.

1562 Ladywood Way, Innisfil

Listing courtesy of HARVEY KALLES REAL ESTATE LTD..

$11,888,000
9 Beds ⋅ 11 Baths ⋅ S12562972 MLS® #
Welcome to Goffat Island, your own private 11-acre sanctuary on the beautiful Lake Simcoe, offering the perfect blend of serene island living and modern convenience. This exceptional property, located just a two-hour drive from Toronto and a mere 350 meters from the mainland, includes a dedicated shoreline lot at 4739 Cedar Point Lane. This mainland base provides essential amenities like parking, a garage, hydro connection, and a 58-foot concrete boat dock, ensuring seamless access to your island retreat. The island itself is a fully-developed cottage resort, having undergone extensive renovations with nearly $9 million in investments, making it a pristine turn-key opportunity. This unique island property is supported by robust, independent utilities, highlighted by a dedicated 1,600-amp power supply running underground from the mainland. The island's 800-amp distribution system-substantiated by the main cottage's 700-amp panel-ensures ample capacity for modern resort operations, representing a $950,000 infrastructure investment. Wastewater is efficiently managed through three strategically placed septic beds, servicing key building areas and ensuring complete operational self-sufficiency. It features 9 versatile rental suites, a conference and dining hall ideal for events, a general store, and a total of 7 main buildings, all set amidst beautifully cleared and wooded level land. With a 65-foot concrete pier, additional docks, and multiple waterfront decks, the property is perfectly equipped for both private enjoyment as a luxurious family compound and as a lucrative revenue-generating business with potential for further expansion like campsites. This is a rare chance to own a complete, move-in ready island paradise that promises an unparalleled lifestyle and a sound investment.

1000 Goffatt Island N/A, Ramara

Listing courtesy of BAY STREET GROUP INC..

$6,999,900
10 Beds ⋅ 8 Baths ⋅ S13037376 MLS® #
Welcome to one of Canada's most iconic luxury log homes, a rare Georgian Bay waterfront estate often described as the "Yellowstone of the North." Located at the very tip of Cedar Point on Georgian Bay, this one-of-a-kind waterfront mansion offers exceptional privacy, panoramic bay views & an irreplaceable point-of-land setting.Built in 2002 as a private resort-style retreat, this custom log estate sits on 4.37 acres with 412+ ft of shoreline, featuring both sandy & pebble beaches, a 90ft stone pier & an 80ft seasonal dock - ideal for boating, swimming & luxury waterfront living. With approximately 14,000 sq ft of living space, the home showcases master craftsmanship, soaring vaulted ceilings, exposed timber construction & uninterrupted water views from nearly every room.The main residence offers 8 bedrooms & 8 bathrooms, plus separate guest or staff quarters w/ 2 additional bedrooms & 2 bathrooms, making it ideal for multi-generational living, executive retreats or luxury hosting. A striking 20-ft grand foyer w/ hand-carved log doors & a rare carved centerpiece sets the tone for this architectural masterpiece.Designed for entertaining, the home features formal & casual living areas, a chef's kitchen with premium Dacor, Thermador & Sub-Zero appliances, butler's pantry, stone fireplaces, wet bar, private office & a spectacular main-floor primary suite with vaulted ceilings, spa-style ensuite & private waterfront deck. The walk-out lower level includes a newly constructed accessible bedroom w/ ensuite, games room, gym, home theatre & an unforgettable 20-seat English-style pub.Outdoors, enjoy landscaped grounds, gentle streams, cabana, private beach & an 8-person in-ground hot tub. Additional features include in-floor radiant heating, heated 4-car garage, cedar shingle roof, irrigation system, cobblestone driveway, Starlink high-speed internet & reliable cell service. A true Georgian Bay luxury estate, offering rare frontage, resort-level amenities & legacy-level value.

100 Melissa Lane, Tiny

Listing courtesy of Royal LePage Locations North.

$5,590,000
8 Beds ⋅ 9 Baths ⋅ N13552700 MLS® #
Discover a rare opportunity to own an exceptional waterfront family estate on the prestigious Summer Place shoreline. Set on approximately 2.14 acres with 102 feet of private sandy beachfront and eastern exposure, this remarkable property captures breathtaking, uninterrupted views across Lake Simcoe, creating the perfect setting for spectacular sunrises.Designed for multi-generational living, entertaining, and year-round enjoyment, the home offers approximately 5,662 sq. ft. above grade and over 7,000 sq. ft. of finished living space. With eight generously sized bedrooms and nine bathrooms, including a primary retreat overlooking the lake, there is exceptional space for family and guests alike.The heart of the home is a spacious, light-filled eat-in kitchen featuring extensive cabinetry, generous preparation space, and a large centre island. The adjoining Muskoka room, formal dining room, and impressive great room flow seamlessly to an expansive waterfront deck, creating exceptional indoor-outdoor living and entertaining. Warm Muskoka-inspired architecture, soaring vaulted ceilings, four wood-burning fireplaces, and dramatic floor-to-ceiling windows beautifully frame the spectacular waterfront setting.Outside, the lifestyle is equally impressive. Enjoy a double dry boathouse with marine rail and rooftop patio, expansive docking, a separate guest bunkie, pickleball court, hot tub, beautifully landscaped grounds, and outstanding privacy-all designed to embrace waterfront living at its finest.Additional features include geothermal heating and cooling, 400-amp electrical service, a four-car attached garage, and numerous thoughtful upgrades throughout.Ideally located just one hour from the GTA and minutes to Friday Harbour, golf, marinas, shopping, and dining, this exceptional legacy property offers an extraordinary opportunity to create generations of cherished family memories on one of Lake Simcoe's most coveted waterfront shorelines.

3209 Summer Place, Innisfil

Listing courtesy of CHESTNUT PARK REAL ESTATE LIMITED.

$5,250,000
8 Beds ⋅ 8 Baths ⋅ S13472210 MLS® #
Incomparable Private West Facing 2 Acres With 239 Ft. Of Water Frontage in One of the Finest Large Lot Communities in Southern Georgian Bay. Private Sand Beach. New Heavy Duty Dock in the Box 2025 Architect Designed Home With Large Rooms, 10-27 Ft Ceilings, Rock Elm Floors, Stone Fireplaces, Walls of Glass Facing Sunsets. Over 9,000 Sq. Ft of Luxury Living. Entertainment Sized Kitchen and Dining, Sensational Burled Maple Media Room, Cocktail Room, and Lower Screened Muskoka room. This Exquisite Luxury Estate Is a Custom Designed Multi-Generational Retreat With 2 Kitchens, 8 Spacious Bedrooms, 8 Baths, 3 Laundry Rooms, Multiple Walkouts, Vaulted Ceilings. Every Corner of This Home Exudes Comfort, Tranquility and Functionality and the Meticulous Craftsmanship Is Evident in Its Design Details. Separate 2-Bedroom, 2 Bath Apartment or Guest Quarters Over Garage. Immersed in the Natural Beauty of Its Surroundings, This West-Facing Sanctuary With Crystal Clear Waters, Gifts Its Occupants With Breathtaking Sunsets and Picturesque Vistas of Georgian Bay and the Hills of the Blue Mountains, Plus the Best Boating in South Georgian Bay.

114 Melissa Lane, Tiny

Listing courtesy of FARQUHARSON REALTY LIMITED.

$4,998,000
5 Beds ⋅ 6 Baths ⋅ S13215634 MLS® #
Welcome To 39 Plunkett Court, An Extraordinary Custom-Built Waterfront Estate Offering 99' Of Frontage On Kempenfelt Bay In Barrie's Prestigious Tollendal Neighbourhood. Located On An Exclusive Cul-De-Sac, This Luxury Residence Showcases Timeless Architecture, Refined Finishes, And Resort-Style Living With Direct Waterfront Access. Built In 2017, This Exceptional Home Offers Over 5,300 Sq Ft Of Finished Living Space Featuring Soaring 22-Foot Ceilings, Dramatic Floor-To-Ceiling Windows, And A Bright Open-Concept Layout Designed To Capture Panoramic Lake Views And Spectacular Sunsets. The Gourmet Chef's Kitchen Features High-End Appliances, Sleek Finishes, And Seamless Flow Into The Expansive Living And Dining Areas. A Main Floor Den Provides The Perfect Space For A Private Office Or Retreat. The Main-Level Primary Suite Features A Custom Dressing Room, Spa-Inspired Ensuite, And Stunning Water Views. Upstairs Offers 3 Additional Spacious Bedrooms, Each With Their Own Private Ensuite Bathroom. The Fully Finished Walkout Lower Level Includes An Additional Bedroom, Second Kitchen, Custom Wine Cellar, Large Family Room With Pool Table, And A Bonus Room Ideal For A Home Office, Gym, Or Flex Space, Creating A Functional And Luxurious 4+1 Bedroom Layout. Outside, Enjoy A Private Lakeside Retreat Complete With A Saltwater Swimming Pool, Pool Cabana, Bocce Court, Open-To-Above Entertaining Patio, Covered Lower Patio, Soffit Lighting, Flagstone Steps To The Water, And A Steel Dock Perfect For Boating And Waterfront Enjoyment. Complete With A Triple-Car Garage And Exceptional Attention To Detail Throughout, This Rare Waterfront Offering Combines Luxury, Privacy, And The Ultimate Lake Simcoe Lifestyle.

39 Plunkett Court, Barrie

Listing courtesy of ROYAL LEPAGE REALTY PLUS.

$4,995,000
5 Beds ⋅ 5 Baths ⋅ S13568450 MLS® #
Perched along pristine waters, this property is one of south-east Georgian Bay's most iconic waterfront estates. Built in 2007, the breathtaking 9,000+ sq ft bungalow with a walkout lower level is a masterpiece of custom millwork and craftsmanship. As your gateway to the 30,000 Islands, the property features a stone circle drive and a cement drive leading to a private harbor. With a 5-foot depth to accommodate a large motor yacht, the shoreline also boasts a sandy beach and a 2-bay dry boathouse topped by a stone observation patio. It is the ultimate spot for sunset views over Penetang Bay and unobstructed views north up the Gap to Cognashene, all framed by manicured perennial gardens.Inside, soaring vaulted ceilings and heated radiant floors run throughout. The open-concept main floor seamlessly integrates a great room with a wood-burning fireplace, lounge, TV area, formal dining, and a breakfast nook. The professional chef's kitchen features a Sub-Zero fridge, Miele coffee station, three Miele ovens, a steamer, and two dishwashers. A spacious mudroom leads to a massive walk-in pantry with a built-in second fridge and standup freezer, with a raised-bed vegetable garden just outside. Uniquely offering main-floor resort luxury, this level boasts a spectacular indoor saltwater pool with a swim system, an executive office with bay views, guest rooms, and a luxurious primary suite.An elevator provides easy transit to the walkout lower level, designed for premium entertainment with two patios, a custom wine cellar, and a cedar storage room. This level also features a self-contained 1-bedroom in-law suite. Complete with 5 bedrooms, 5.5 baths, a whole-home Generac generator, and two heated double-car garages with floor drains, this estate offers absolute peace of mind. Perfectly balancing privacy and accessibility, it is just 10 minutes from Midland and Penetanguishene.

250 Gordon Drive, Penetanguishene

Listing courtesy of Sotheby's International Realty Canada.

$4,899,000
5 Beds ⋅ 5 Baths ⋅ S13480050 MLS® #
Curated with pure intention, exceptionally executed - here's a spectacular opportunity to own one of Lake Simcoe's most admirable waterfront estates! This custom-built residence offers over 6,000 sq ft of refined living space on 1.2 acres of professionally landscaped grounds. With 107 feet of prime WESTERN shoreline, the property is perfectly positioned for unforgettable sunsets and an unmatched lakeside lifestyle. Crafted by award-winning West Brennen Construction, the home blends timeless elegance with modern performance. Solid 8' walnut doors and flooring, intricate plaster and imported tin ceiling details, natural quartzite, granite, and leathered granite surfaces create a sense of warmth, sophistication, and enduring quality. The layout features four spacious bedrooms, a dedicated office, and five impeccably designed bathrooms, including a spa-like primary ensuite featured in House & Home magazine. The walk-out lower level offers 9.5' ceilings, a custom media room, a games area, and an English-style pub with cherry wood millwork, marble floors, and granite counters, the ultimate entertaining space. Smart home technology controls lighting, irrigation, and security, while premium mechanical systems, including 400-amp service and a 30KW Generac generator, provide year-round comfort and reliability. Outside, park-inspired landscaping surrounds an outdoor kitchen, waterfall feature, and a charming gazebo ready for a hot tub or lakeside lounging. The heated four-car garage with Rhino-coated floors and custom storage adds practicality to luxury. At the waters edge, a rare dry boathouse with finished space above offers excellent flexibility ideal for guests, a studio, or office, while two marine railways, deep water access, and twin 40' docks easily accommodate a 28' boat and Seadoos. With flawless craftsmanship, modern functionality, and an unbeatable waterfront setting, this property offers a truly elevated lifestyle where every detail has been thoughtfully executed.

153 Creighton Street S, Ramara

Listing courtesy of Sotheby's International Realty Canada.

$4,699,900
8 Beds ⋅ 6 Baths ⋅ N13520652 MLS® #
Welcome to 262 Trillium Place on Kempenfelt Bay, a rare year-round waterfront cottage set on a deep 1.41 acre lot with about 125 feet of private shoreline. At this price point, the value is clear. You are not just buying lakefront, you are getting space, privacy, a large bungalow layout, a dock, boat lift, detached garage, & room for the whole family to gather. This is the kind of cottage that can hold every stage of life. Summer weekends with friends. Holidays with grandparents. Teens with their own space. Quiet workdays by the water. Full family weeks where the best plans are simple ones: swim, boat, eat, rest, repeat. The main floor is bright, open, & easy to live in. The kitchen is the heart of the space, with a large island, built-in fridge, gas stove, warm wood accents & room for everyone. It opens to the dining area & great room, where high ceilings, large windows & a wood-burning fireplace create a warm lake-house feel. The large main floor family room offers even more space to gather & features a large gas fireplace. A sunken living room with heated floors gives you another peaceful place to sit, read, or watch the bay. The layout gives rare flexibility. One wing has the primary suite with walk-in closet & spa-like ensuite. The other wing has more bedrooms, baths, & laundry, making it ideal for children, guests, or extended family. With 6 bedrooms on the main floor, this bungalow offers room to be together & room to step away. The lower level adds even more use, with 2 large bedrooms, a full bath, heated floors, an electric fireplace, & a glass-walled gym. It can serve teens, guests, in-laws, or a live-in nanny with ease. Outside, the property feels calm & private. Enjoy the lawn, the lake, the dock, & the space to add more, whether that means a pool, sport court, or guest space. For buyers looking for a move-in-ready waterfront cottage close to the GTA, this is a rare chance to own a true Lake Simcoe lifestyle property with comfort, scale, & strong value.

262 Trillium Place, Innisfil

Listing courtesy of ENGEL & VOLKERS BARRIE.

$4,699,000
5 Beds ⋅ 3 Baths ⋅ S13473724 MLS® #
Top Reasons You Will Love This Home: Experience the epitome of lakeside living in this breathtaking 5,348 square foot waterfront estate, gracefully set on nearly two acres of pristine privacy. With 317' of clean, gently sloping shoreline, you'll enjoy effortless access for swimming, boating, and pure relaxation. A detached boathouse with an inviting second-level deck offers front-row seats to awe-inspiring sunsets. Impeccably landscaped grounds frame this retreat, highlighted by a striking 50' natural stone fireplace and a cedar-lined, wood-fired sauna with a private changing area. Inside, thoughtful design meets timeless Muskoka charm. Crafted with custom hand-hewn Douglas fir trim, doors, and staircases, made on-site. Expansive tilt-and-slide windows and wall-to-wall rear doors seamlessly blend indoor and outdoor living. Throughout, premium flooring and high-end cabinetry echo the home's commitment to quality, while a Sonos multi-zone audio system fills every corner with music. An advanced automated security system keeps watch. Wake each day to panoramic water views from the serene primary suite, where oversized windows invite the outdoors in. A grand living room crowned by a soaring 23' natural stone fireplace creates a warm, dramatic focal point. The chef's kitchen with top-of-the-line appliances, Caesarstone centre island, premium cabinetry, and a spacious pantry. Adjacent, the Muskoka room offers a natural stone fireplace, built-in barbeque with granite counters, and expansive sliding doors and screens. Discover the impressive 2,000 square foot oversized three-car garage. Above, a private guest suite offers a spacious bedroom and a cozy living room with a corner fireplace. Inside the main home, four additional bedrooms on the upper level ensure everyone has their own space. This estate captures the true spirit of Muskoka living, offering both an elegant family home and a timeless retreat. 5,348 above grade sq.ft plus an unfinished basement.

1250 Frankland Lane, Severn

Listing courtesy of FARIS TEAM REAL ESTATE BROKERAGE.

$4,499,999
5 Beds ⋅ 5 Baths ⋅ S13251518 MLS® #
Welcome to 376 Brewery Lane, a stunning luxury waterfront home situated on one of Orillias finest streets. This exceptional property offers 104 feet of prime Lake Couchiching frontage on a beautifully landscaped half-acre lot with western exposureperfect for soaking in spectacular sunsets and views of downtown Orillia. Completely renovated from top to bottom, this home offers nearly 5400 square feet of high-end living space, featuring 5 bedrooms and 4.5 bathrooms. The gourmet kitchen is a showstopper with two impressive 10-foot islands, granite countertops, and premium appliances from WOLF, SUBZERO, and Thermador. The open-concept main floor boasts large windows that frame lake views, a cozy gas fireplace in the living room, and a walkout to an expansive deckideal for both relaxation and entertaining. The upper level features 3 spacious bedrooms, each with its own ensuite, and a laundry room for added convenience. The primary suite is a true retreat with vaulted ceilings, a grand walk-in closet complete with built-ins and an island, and a spa-like ensuite featuring a walk-in shower, soaking tub, heated floors, and double vanity. The finished walkout basement offers 9-foot ceilings, a second full kitchen, separate laundry, and a private entrance, making it perfect for extended family or guests. Outside, the property truly shines with a heated saltwater pool surrounded by interlock patios, multiple seating areas, and a large dock complete with sea doo lifts. The private stone path leads to a hard-packed lakefront, perfect for enjoying summer days by the water. Double gated entries and a heated interlock driveway provide both privacy and convenience. This rare waterfront gem is located at the end of a quiet court, offering tranquility and luxury living.

376 Brewery Lane, Orillia

Listing courtesy of ENGEL & VOLKERS BARRIE.

$4,490,000
5 Beds ⋅ 5 Baths ⋅ S13508726 MLS® #
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.

209 Bay Street, Oro-Medonte

Listing courtesy of RE/MAX HALLMARK CHAY REALTY.

$4,199,000
4 Beds ⋅ 6 Baths ⋅ S13447998 MLS® #
Perched majestically on Midland Point, this magnificent 4-bedroom, 5.5-bathroom estate commands 99 feet of pristine private Georgian Bay shoreline, offering an unparalleled canvas of panoramic water views and inspiring sunrises. Spanning 4,841 sq ft, this impeccably updated residence embodies sophisticated waterfront living. A culinary masterpiece awaits in the gourmet kitchen, featuring professional-grade appliances and a sprawling island, all designed to maximize the breathtaking bay vistas. Convenience meets luxury with a main floor primary suite and dedicated laundry. The expansive main deck is an entertainer's paradise, boasting an outdoor kitchen, a unique retractable garage door, and crystal-clear Invisirail for unobstructed views. The lower walk-out level transforms into a world of leisure, complete with a dedicated billiards room, an impressive office/library, a family room warmed by a fireplace, a private fitness area, and an exquisite wine cellar. Step directly from here into a covered three-season sanctuary, featuring a crackling wood fireplace and a bubbling hot tub. Enhancing this exceptional property are a contemporary 600+ sq ft street-front office with a 4-piece bath, ideal for remote work or a home business, and a charming, 1,200 sq ft 1-bedroom, 2-bathroom guest house, offering a cozy retreat with its own wood-burning fireplace. The waterfront truly defines this property, with a natural sandy beach, a welcoming fire pit, and a double dry boathouse equipped with a rail system for two vessels and a private dock. Above the boathouse, a private putting green offers a unique opportunity to refine your short game while soaking in the stellar views of the private beach and Midland Bay. As you arrive, meticulously manicured perennial gardens unfold, creating a serene, park-like drive that leads to the heart of this extraordinary home.

29 McArthur Drive, Penetanguishene

Listing courtesy of Sotheby's International Realty Canada.

$3,999,999
5 Beds ⋅ 5 Baths ⋅ S13479230 MLS® #
Welcome to 1688 Lakeshore, a spectacular custom-built waterfront estate set on an impressive 151'x 305' lot. Offering over 5,000 sq. ft. of beautifully designed living space, breathtaking water views, and exceptional craftsmanship throughout, this fully winterized retreat is designed for those seeking luxury, comfort, and the ultimate waterfront lifestyle. From the moment you enter, you'll be captivated by the bright open-concept design, soaring ceilings, exposed beams, designer finishes, and stunning modern lighting. The heart of the home is the gourmet kitchen, complete with a massive centre island that seamlessly connects to the living and dining areas, creating the perfect space for entertaining family and friends. This exceptional residence features 5 spacious bedrooms and 5 beautifully appointed bathrooms. The luxurious primary suite is conveniently located on the main floor and offers a cozy fireplace, stunning waterfront views, and a peaceful retreat from everyday life. Upstairs, four generously sized bedrooms provide plenty of space for family and guests, many enjoying picturesque views of the water and access to an expansive deck overlooking the shoreline. Designed for year-round enjoyment, the home is equipped with surround sound throughout, creating an incredible atmosphere both indoors and outdoors. The fully finished basement provides additional living and recreational space, perfect for hosting gatherings, movie nights, a games room, home gym, or guest accommodations. Step outside and discover your own private oasis. Beautifully landscaped gardens, multiple outdoor entertaining areas, a separate sauna, and spectacular waterfront scenery create a setting that feels like a luxury resort. Whether enjoying a quiet morning coffee by the water or hosting unforgettable summer gatherings, every day feels like a vacation. Complete with a spacious 3-car garage and situated on a rare oversized waterfront lot with potential severance opportunities.

1688 Lakeshore Drive, Ramara

Listing courtesy of PROPERTY.CA INC..

$3,999,900
4 Beds ⋅ 6 Baths ⋅ S13582762 MLS® #
Some homes exist in a category all their own, and this is that home. Set on 116 feet of prized east-exposure shoreline on Lake Couchiching, on one of Orillia's most sought-after waterfront streets. This exceptional custom-built residence is a rare opportunity to own a truly remarkable waterfront estate. From the moment you step through the grand entrance, the craftsmanship and attention to detail are evident. Expansive lake views serve as a backdrop throughout more than 6,700 square feet of finished living space.The showpiece kitchen features two separate serveries and flows seamlessly into the formal dining room, family room with fireplace, and an impressive screened-in porch spanning approximately 650 sq. ft. with waterfront views. The outdoor living space offers multiple areas for dining, entertaining and relaxing. The main-floor primary suite is a private retreat with separate walk-in closets, dual vanities and a spa-inspired ensuite. A three-car garage, laundry room and office nook round out the main level. Upstairs, two spacious bedrooms each enjoy their own ensuite, connected by an executive-style office with a fireplace and ensuite privileges. A custom elevator provides access to every level of the home.The lower level is built for recreation and relaxation, with a home theatre featuring a projector screen and surround sound, a wine cellar, an additional bedroom, a fitness area and a steam shower. A whole-home generator adds convenience and peace of mind. At the water's edge, the boathouse complements the property with a one-bedroom unit, complete with its own kitchen, bathroom and laundry, ideal for extended family or guests. Rarely does a property of this calibre come available. Exceptional craftsmanship, extensive amenities and a premier Lake Couchiching setting come together in this truly extraordinary waterfront offering.

28 Maple Drive, Orillia

Listing courtesy of RE/MAX RIGHT MOVE.

$3,999,900
N12724870 MLS® #
Build your dream home here on 105 sprawling acres in the peaceful countryside. This parcel of vacant land offers endless opportunities with forested acreage, 38 workable acres, the beauty of the Nottawasaga River flowing through it, and the possibility of severance to create multiple building lots. Situated only minutes from Alliston, and just 40 minutes to the GTA.

7468 25th Side Road, Adjala-Tosorontio

Listing courtesy of CENTURY 21 B.J. ROTH REALTY LTD..

$3,995,000
6 Beds ⋅ 5 Baths ⋅ S13514876 MLS® #
Top 5 Reasons You Will Love This Home: 1) Executive waterfront living in one of Orillia's most prestigious communities, showcasing fresh contemporary style throughout 6,339 finished square feet with open-concept living spaces, sprawling bedrooms, and luxurious bathrooms 2) Lower level featuring a large walkout recreation room, home theatre, and excellent in-law potential, providing exceptional flexibility for family living and entertaining 3) Situated on approximately one acre with 100' of shoreline on Lake Couchiching, part of the renowned Trent-Severn Waterway system 4) Outdoor living enhanced by a private dock, stone firepit patio, and gazebo, creating the perfect setting for relaxation and waterfront enjoyment 5) Recently built boathouse featuring a marine rail system, along with a large new deck and a dedicated hot tub room below, offering an exceptional waterfront lifestyle experience. 3,351 above grade sq.ft. plus a finished lower level.

354 Brewery Lane, Orillia

Listing courtesy of FARIS TEAM REAL ESTATE BROKERAGE.

$3,995,000
S13130562 MLS® #
A Truly Exceptional Fall And Winter Opportunity To Own Strawberry Island-A 26-Acre Private, Iconic, And Historically Significant Sanctuary On Lake Simcoe And A Haven All Year Round. A Rare Dual Offering: 26-Acre Private Island + Marina Del Rey Mainland Lot With Direct Access. Paired With A Coveted 80 X 303 Ft Mainland Lot At 4123 Glen Cedar Drive With Direct Canal Access Through Marina Del Rey, This Package Delivers Unmatched Convenience And Year-Round Accessibility. Steeped In Centuries Of History, From Its Importance To Indigenous Communities As A Gathering Place And Lookout Post, To Its Victorian-Era Resort Days, To Its Quiet Spiritual Retreat That Hosted Pope John Paul II In 2002, This Island Offers Extraordinary Privacy, Natural Beauty, And Legacy. As The Seasons Change, The Island Becomes Even More Magical With Crisp Fall Colours Wrapping The Shoreline, Peaceful Winter Trails For Snowshoeing Or Quiet Hikes, Expansive Frozen Panoramas Ideal For Photography And Serene Escapes, And A Tranquil Setting Perfect For Cold-Weather Activities, Fireside Gatherings, And Ultimate Privacy. Surrounded By Calm Waters, Mature Trees, And Panoramic Views, Strawberry Island Stands Alone As One Of The Rarest Opportunities On Lake Simcoe. Combined With The Convenience Of The Marina Del Rey Mainland Lot For Easy Year-Round Access And Docking, This Is Not Just Land-It Is A Remarkable Piece Of Ontario's Living History.

1000 Strawberry Island, Ramara

Listing courtesy of RE/MAX HALLMARK YORK GROUP REALTY LTD..

$3,950,000
6 Beds ⋅ 6 Baths ⋅ S13502250 MLS® #
A rare offering on the shores of Georgian Bay in Tiny Township, this extraordinary waterfront estate redefines luxury living with an unmatched blend of privacy, craftsmanship, and versatility. Set on nearly 2 acres w/approx 200 ft of pristine sandy shoreline, this remarkable property captures breathtaking sunsets and panoramic water views stretching toward Blue Mountains. Designed for those who value both connection and independence, the residence seamlessly incorporates two fully self-contained living spaces under one roof, creating an opportunity for multi-generational living, executive retreats, luxury guest accommodations, or an unparalleled family compound. From the moment you arrive, the setting evokes a sense of exclusivity. A mature forest canopy, circular driveway, and expansive grounds create a private sanctuary where the pace of life slows and the beauty of nature takes centre stage. Inside, timeless architectural details showcase exceptional quality throughout. Reclaimed timber beams, rich wood finishes, handcrafted stone fireplaces, and thoughtfully designed gathering spaces create a refined and welcoming atmosphere. Expansive windows frame spectacular waterfront vistas, filling the home with natural light and ensuring the views remain the focal point. With six bedrooms, seven bathrooms, multiple living and entertaining areas, finished lower-level spaces, and several walkouts to the outdoors, the home is designed to accommodate both intimate family moments and large-scale entertaining with ease. Step outside to discover a lifestyle few properties can offer. Spend your days swimming from the sandy beach, kayaking along the shoreline, hosting waterfront gatherings, or simply enjoying the serenity of your own private stretch of Georgian Bay. A legacy property in every sense, this is more than a waterfront home-it is a destination for generations to come, offering an exceptional opportunity to experience one of Ontario's most coveted waterfront settings..

731 Concession 15 N/A W, Tiny

Listing courtesy of Revel Realty Inc.

$3,950,000
9 Beds ⋅ 5 Baths ⋅ S12794486 MLS® #
Welcome to your dream waterfront oasis in Collingwood, Ontario. This stunning home offers the rare luxury of docking your boat right at your property, giving you immediate access to the sparkling waters of Georgian Bay, renowned for its boating and breathtaking views. With nine grand bedrooms and a spacious coach house, theres ample room for everyone to savour the luxury and serenity of this unique property. The cozy coach house serves as the perfect in-law suite or guest retreat, offering privacy and comfort with high ceilings and an array of games for entertainment.

156 Bartlett Boulevard, Collingwood

Listing courtesy of SOTHEBY'S INTERNATIONAL REALTY CANADA.

$3,799,900
S12147670 MLS® #
An exceptional opportunity to own 72.62 acres of pristine, vacant land with an expansive lakefront along stunning Sturgeon Bay, a gateway to the world-renowned Georgian Bay. This rare offering boasts natural beauty, privacy, and unlimited potential for development or a private estate retreat. Excellent location near Midland and Waubaushene with easy access to Highway 400 under two hours from the GTA. Whether you're seeking a tranquil escape, investment potential, or the perfect cavas for your vision, this property offers endless possibilities. Don't miss this chance to own a large tract of lakefront land in one of Ontarios most desirable recreational areas.

185 Park Street, Tay

Listing courtesy of RE/MAX ALL-STARS REALTY INC..

$3,795,000
4 Beds ⋅ 4 Baths ⋅ S13138142 MLS® #
Welcome To The Beach Life! Built In 2026, This Gorgeous Beachfront Home Is Completely Custom Finished From Top-To-Bottom With Luxury Upgrades & WOW Factor Galore. Nestled Along The Sandy Shores Of Georgian Bay, This Beautiful 4-Bedroom, 4-Bathroom Dream Home Offers Long Breathtaking Views Out Over The Crystal-Clear Water Across To Blue Mountain. Anchoring The Open Concept Main Floor Is A Jaw-Dropping, Professionally Designed, Eat-In Kitchen Boasting A Chef's Waterview, Custom White-Oak Cabinetry, Natural Quartzite Countertops, Huge Island & Built-In Premium Appliances. Open Living/Dinning Room Features A Massive Floor-To-Ceiling Window Wall Showcasing The Most Incredible Georgian Bay Views, Woodburning Guillotine Fireplace, 10 Ft. Ceilings, Heated Floors Throughout & Walk-Out To Huge Two-Tier Composite Deck Overlooking Your Beachfront Oasis (West Facing For Maximum Sunsets). A Full Wet Bar & Beautiful Guest Bath Finish Off The Main Floor. Huge Primary Suite Offers Private Waterview Balcony, Large Walk-In Closet & Incredible Spa-Like Ensuite With Deep Soaker Tub, Heated Hot-Stone Lounge, Custom White-Oak Double Vanity, Rain-Shower & Even More Beautiful Beach-Views. Two More Good-Sized Bedrooms, Each With Waterviews, & A Third Stunning Bathroom With Double Rain-Head Glass Shower Completes The Second Floor Perfectly. Fully Finished Lower-Level Features A Open Family Room, 4th Large Bedroom, Another Gorgeous Bathroom, Laundry Room & Tons Of Storage. Beautifully Treed Property Provides Both Privacy & Shade After A Relaxing Day At The Beach & Is The Perfect Spot To Entertain, Relax And Enjoy Evenings Around The Bonfire With Friends & Family. Beachside Sundeck Offers A Nice Private Retreat To Lay-Out, Read A Book Or Catch Some Rays While Listening To The Sound Of The Waves. Potential For Full Guest Suite Above Garage Would Be Perfect For Visitors Or Provide A Great Space For Kids Or Grandkids. Full-Home Natural Gas Generac Generator. 3-Car Garage. 10/10 Quality - MUST SEE!

160 Tiny Beaches Road N, Tiny

Listing courtesy of Royal LePage In Touch Realty.

$3,699,900
4 Beds ⋅ 3 Baths ⋅ S13537858 MLS® #
Welcome to one of Barrie's most exceptional waterfront offerings. Nestled along the shores of Kempenfelt Bay on one of the city's most coveted streets, this architecturally distinctive custom residence blends timeless craftsmanship with contemporary luxury in an unforgettable setting. From the moment you arrive, the home makes a lasting impression. Set on a beautifully landscaped estate lot beneath a canopy of mature trees, the striking timber-frame design, natural stone exterior, standing seam metal roof and expansive covered entrance create a warm yet sophisticated presence unlike anything else on the market. Designed to embrace its spectacular waterfront setting, the home offers breathtaking views of Kempenfelt Bay from principal living spaces while seamlessly connecting indoor and outdoor living. Oversized windows flood the home with natural light and frame the ever-changing beauty of the lake throughout every season. Exceptional craftsmanship is evident throughout, with exposed wood beams, custom millwork, designer finishes, and thoughtfully curated living spaces that balance elegance with everyday comfort. The open-concept layout is ideal for entertaining while maintaining intimate spaces for quiet relaxation. The professionally landscaped grounds provide exceptional privacy and multiple outdoor living areas to enjoy morning coffee, summer evenings, or spectacular sunsets over the water. The lower level continues to impress with generous living space, additional bedrooms, recreation areas, and direct access to the property, making it ideal for guests, multi-generational living, or year-round enjoyment. Located just minutes from downtown Barrie, waterfront trails, marinas, fine dining, shopping, golf, and commuter routes, this is a rare opportunity to own one of Kempenfelt Bay's premier luxury residences where exceptional design, privacy, and an extraordinary waterfront lifestyle come together. *Some Images Virtually Staged*

9 Barrie Terrace, Oro-Medonte

Listing courtesy of CENTURY 21 B.J. ROTH REALTY LTD..

$3,599,000
5 Beds ⋅ 4 Baths ⋅ N13026976 MLS® #
This exceptional 2011 custom-built home with over 3,000 sq ft of finished living space offers the perfect blend of modern luxury and classic cottage charm. Located just one hour north of Toronto on a private road, this stunning property provides just shy of 75 feet of private shoreline and panoramic eastern views for unforgettable sunrises. Gaze out across the lake and catch sight of both Fox and Snake Islands to the south. The waterfront is truly one-of-a-kind, featuring a beautifully crafted stone wall and patio that stretches across the entire frontage, creating an inviting space for entertaining, relaxing, or enjoying direct lake access - this is lakeside living at its finest. A custom-built boathouse with room for a 24-foot boat, a railway system, and a spacious dock make boating and waterfront activities effortless. Inside, the main floor is designed for comfort and connection, with an open-concept layout that includes a great room with a floor-to-ceiling stone wood-burning fireplace, a kitchen, and a main-floor primary bedroom that faces the water. Walk out to the expansive deck for seamless indoor-outdoor living. Upstairs, two more bedrooms and a full bath offer space for family or guests. The fully finished basement adds two additional bedrooms, a full bathroom, and a generous rec room perfect for movie nights, games, or cozy winter gatherings. An attached two-car garage provides direct access to the home, and above it, a partially finished bonus room offers additional square footage for a studio, office, or playroom. Outside, a paved driveway and a second detached two-car garage offer even more storage for recreational gear and vehicles. Low-maintenance landscaping means more time enjoying the lake and less time on upkeep. Whether you're looking for a summer escape or a four-season home, this property delivers the lifestyle you've been waiting for on beautiful Lake Simcoe.

3531 Crescent Harbour Road, Innisfil

Listing courtesy of CHESTNUT PARK REAL ESTATE LIMITED.