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$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. (id:5764)

209 Bay Street, Oro-Medonte

Listing courtesy of RE/MAX HALLMARK CHAY REALTY.

$929,900
4 Beds ⋅ 3 Baths ⋅ S13485848 MLS® #
Fully Renovated From Top To Bottom In The Heart Of Horseshoe Valley! This Turnkey Home Features New Hardwood Flooring, Designer Lighting, Custom Feature Walls, A Stunning Kitchen With Premium Built-In Appliances, Updated Bathrooms With Heated Floors And Glass Walk-In Showers, New Washer & Dryer, Exterior Interlock, And A Custom Front Entry Door.The Fully Finished Walkout Basement Adds Exceptional Value With In-Law Suite Or Secondary Living Space Potential, Offering A Kitchenette, Separate Laundry, Two Bedrooms, Full Bathroom, And Private Walkout Access.Located Minutes From Horseshoe Resort, Vettä Nordic Spa, Golf, Skiing, Trails, And Outdoor Recreation. A Rare Opportunity To Own A Fully Updated Home In One Of Simcoe County's Most Desirable Lifestyle Communities. (id:5764)

16 Oakmont Avenue, Oro-Medonte

Listing courtesy of RE/MAX HALLMARK CHAY REALTY.

$829,000
5 Beds ⋅ 4 Baths ⋅ S13475644 MLS® #
MULTI-GENERATIONAL LIVING MEETS FOUR-SEASON HORSESHOE VALLEY ADVENTURE! Nearly 2,500 finished sq. ft. is only the beginning, with a finished lower level designed for different stages of life, offering in-law potential with its own kitchen, living space, two bedrooms and a full bath. Add a beautifully finished interior, a garage with a custom bar and a lush treed backyard that feels more like a cottage-country escape than a typical in-town lot. Rich hardwood floors flow through the main living areas, where a gas fireplace anchors the space and sliding doors open to a deck overlooking layers of mature greenery. The kitchen pairs timeless shaker-style cabinetry with stainless steel appliances including a gas stove, a tiled backsplash, generous prep space, and a large island that naturally draws people together. The primary suite includes a walk-in closet and 4-piece ensuite featuring a soaker tub, separate shower, and oversized vanity, while two additional bedrooms complete the upper level. Beautifully landscaped front and back, the property is framed by colourful perennial gardens, natural stone walkways, mature trees, and a backyard that feels tucked into the forest. The garage adds an unexpected bonus with a custom bar, wood ceiling, lounge area, and bug-screened doors, creating a casual hangout spot for evenings with friends. Set in a quiet, friendly Horseshoe Valley neighbourhood near parks, trails, skiing, golf, Horseshoe Resort, Vettä Nordic Spa, Horseshoe Heights P.S. and Simcoe Woods Community Centre, with Barrie, Orillia and Lake Simcoe within easy reach. (id:5764)

11 Oakmont Avenue, Oro-Medonte

Listing courtesy of RE/MAX HALLMARK PEGGY HILL GROUP REALTY.

$1,799,900
5 Beds ⋅ 5 Baths ⋅ S13475136 MLS® #
Brand new custom-built bungalow with 5,000 Sqft + living space offering elevated luxury, exceptional craftsmanship, and ultimate comfort on a sprawling 1.3-acre lot. This stunning home features 5 spacious bedrooms and 5 beautifully appointed bathrooms, designed with both elegance and functionality in mind. The open-concept layout is complemented by high-end finishes throughout, creating a seamless blend of sophistication and warmth. The fully finished basement is equipped with radiant in-floor heating throughout, ensuring year-round comfort. Enjoy premium lifestyle features including a private sauna, a dedicated theater room for cinematic experiences at home, and a quiet study perfect for remote work or reading. Car enthusiasts and families alike will appreciate the oversized 3-car garage, offering ample space for vehicles, storage, and more. Experience refined country living with modern luxury in this exceptional custom residence (id:5764)

11 Caldwell Drive, Oro-Medonte

Listing courtesy of CENTURY 21 PEOPLE'S CHOICE REALTY INC..

$1,348,000
4 Beds ⋅ 3 Baths ⋅ S13417362 MLS® #
Welcome to 16 Highland Drive in the sought-after Horseshoe Highlands of Oro-Medonte. This is a rare opportunity on the Highland Drive ridge, one of just nine properties with clear, panoramic views across Horseshoe Valley and Georgian Bay to Meaford-approximately 80 kilometres. Only one other of these view properties has come to market in the past five years. Fully renovated to showcase the spectacular setting, this exceptional walkout bungalow offers seamless open-concept living designed for both everyday comfort and entertaining. The home features four bedrooms and three full bathrooms, with a bright, airy layout throughout. The main level is finished with rich hardwood floors and includes a dedicated, spacious home office-ideal for remote work in a peaceful setting. The updated kitchen is the heart of the home, complete with granite countertops, a large island for gathering, and generous prep space for hosting family and friends. The main floor principal suite enjoys sweeping views, an exceptionally spacious ensuite, and a large walk-in closet. The lower level is as light-filled as the main floor, thanks to glass walkout doors leading to the rear yard. Here you'll find additional bedrooms, a full bathroom with tub and shower, and a small service area that adds flexibility for entertaining or multi-generational living. Set in the heart of Horseshoe Valley, the home offers convenient access to outdoor recreation, including skiing, hiking, biking trails, golf, and the local resort and spa. The community is approximately 15 minutes to Barrie and about one hour to Toronto Pearson International Airport. Nearby amenities include two ski areas within two kilometers, 43 kilometers of cross-country and mountain bike trails, and a new elementary school and community centre just one kilometer away. Opportunities like this are few and far between on this coveted ridge. Experience comfort, space, and exceptional views in one remarkable home. (id:5764)

16 Highland Drive, Oro-Medonte

Listing courtesy of RE/MAX HALLMARK CHAY REALTY.

$1,599,999
4 Beds ⋅ 4 Baths ⋅ S13412322 MLS® #
REDUCED FOR QUICK SALE! STUNNING 4 BEDROOM & 4 BATH WALKOUT BUNGALOW WITH GREAT FEATURES ON A 1.36 ACRE PRIVATE LOT! 100 PERCENT RUG FREE & HANDICAP FRIENDLY WITH A GREAT MAIN LEVEL ACCESSORY APARTMENT WITH PRIVATE ENTRANCE, OPEN CONCEPT WITH A DREAM KITCHEN/ISLAND/KITCHEN AID APPLIANCES/UPGRADED CABINETS ++ , 9' CEILINGS, QUALITY HARDWOOD FLOORS, 3 FIREPLACES, LED POT LIGHTS THROUGHOUT, MAIN FLOOR PRIMARY BEDROOM WITH WALK IN CLOSET & ENSUITE WITH HEATED FLOORS & JACUZZI OVERSIZED BATH, LOWER LEVEL BEDROOM CAN BE EASILY USED AS A OFFICE WITH ITS OWN PRIVATE ENTRANCE & 4 PIECE BATH, HUGE 70' WIDE DECK, DREAM TRIPLE CAR "2011 SQUARE FEET GARAGE " 12' 3'' HIGH/ 4 OVERSIZED DOORS 2- 10 X9'/ 2- 10 X10'/ 50 AMP OUTLET FOR MOTOR HOME OR ELECTRIC CAR/ 4 HIGH END GARAGE DOOR OPENERS/PAVED DRIVEWAY TO PARK ALL THE TOYS, CUSTOM PRECAST ON ALL OPENINGS, IN GROUND SPRINKLERS, EXTERIOR/INTERIOR POT LIGHTS, HUGE LOT GOES ALL THE WAY BACK TO METAL FENCE +++ QUICK CLOSING AVAILABLE (id:5764)

15 Caldwell Drive, Oro-Medonte

Listing courtesy of SUTTON GROUP INCENTIVE REALTY INC..

$1,299,999
4 Beds ⋅ 3 Baths ⋅ S13232422 MLS® #
Welcome to this stunning log-style chalet nestled in the heart of Horseshoe Valley, Oro-Medonte - one of Ontario's most sought-after four-season communities. This beautifully crafted 4-bedroom, 3-bathroom home seamlessly blends rustic charm with modern smart home technology, offering comfort and convenience at every turn. The open-concept main floor features soaring ceilings, a gas fireplace, brand new flooring throughout, and a spacious master suite with ensuite - all designed with entertaining in mind. The upper level offers three additional bedrooms and a full bath. The fully finished walkout basement provides additional living space perfect for a rec room or family retreat. Step outside to a massive back deck and fully fenced lot overlooking a private 0.377-acre property surrounded by mature trees and breathtaking natural surroundings. Additional features include forced air natural gas heating, central air conditioning, a durable metal roof, whole-home HEPA air filtration, 2-car built-in garage, and a paved driveway accommodating up to 12 vehicles. Multiple upgrades throughout. Located minutes from the renowned Vetta Nordic Spa, Horseshoe Valley Resort, incredible golf courses, skiing, hiking and biking trails, and the brand new local elementary school - all within an incredible family-friendly neighbourhood. With easy access to Highways 11 and 400, you're just 50 minutes from the GTA. A truly rare opportunity. (id:5764)

17 Bridle Path, Oro-Medonte

Listing courtesy of SUTTON GROUP INCENTIVE REALTY INC..

$1,399,900
4 Beds ⋅ 3 Baths ⋅ S13223608 MLS® #
Welcome To Your Private Hillside Retreat In The Heart Of Horseshoe Valley. Set On Over 6 Acres And Perched Beautifully Above The Surrounding Landscape, This 4 Bedroom, 3 Full Bathroom Home Offers Stunning Elevated Views, Exceptional Privacy & A Peaceful Natural Setting Surrounded By Forest & Trails. Offering Approximately 2,000 Sq Ft Of Bright Main Floor Living Space Plus A Fully Finished Walk-Out Basement, This Home Provides Nearly 4,000 Sq Ft Of Total Living Space Ideal For Families, Multi-Generational Living Or Those Seeking Space & Flexibility. Inside, The Home Showcases A Bright Open-Concept Layout Flooded With Natural Light, Along With 2 Full Kitchens & A Fully Self-Contained In-Law Suite Perfect For Extended Family, Guests Or Potential Income Opportunities. The Lower Level Layout Also Offers Flexibility For Future Owners, As The In-Law Suite Could Easily Be Converted Back Into One Large Open Recreational Living Space If Desired. A Standout Feature Of This Property Is The Rare Two-Level Garage Setup Including An Attached Double-Car Garage Plus A Lower Third Bay Ideal For A Workshop, Recreational Vehicle Storage Or The Perfect Hobby Space. Designed For Outdoor Living, The Property Features Over 6 Acres Of Land, Private Trails, A Fenced Area Ideal For Children & Pets, Plus Additional Landscaping Including Perennial Gardens, Cedar Trees & Lilac Bushes Creating A Beautiful & Private Outdoor Setting. Relax & Unwind In The Brand New Jacuzzi Hot Tub Perfectly Positioned To Enjoy Peaceful Country Nights & The Surrounding Nature. Recent Updates Include A/C (2022), Fencing (2022), Lifestyle Garage Screen (2022), Main Floor Fridge (2023), Stove (2026) & Brand New Jacuzzi Hot Tub (2026). Located Just Minutes To Horseshoe Resort, Vettä Nordic Spa, The New Horseshoe Valley Public School, Golf Courses, Trails, Barrie & Orillia, This Property Offers The Perfect Balance Of Privacy, Nature, Space & Convenience Within One Of Oro-Medonte's Most Desirable Communities. (id:5764)

2700 Line 4 North, Oro-Medonte

Listing courtesy of CENTURY 21 B.J. ROTH REALTY 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. (id:5764)

2533 Ridge Road West, Oro-Medonte

Listing courtesy of Sotheby's International Realty Canada.

$1,599,000
4 Beds ⋅ 4 Baths ⋅ S13086090 MLS® #
Welcome to a refined expression of modern luxury, where design-forward interiors meet a serene, lifestyle-driven setting. Situated on an expansive 0.25 acre lot, this newly built residence has been thoughtfully customized with elevated finishes and future-ready enhancements throughout. At the heart of the home, a chef-inspired kitchen awaits your personal finishing touch-featuring an oversized quartz island, sophisticated two-tone cabinetry, and rough-ins for a pot filler, gas range, and stacked microwave/convection wall oven. The space flows seamlessly into the impressive GREAT room, where soaring double-height ceilings, a sleek electric fireplace, and an abundance of natural light from over 16 oversized windows create a striking yet inviting atmosphere. The upper level offers four generously sized bedrooms and three well-appointed bathrooms, perfectly suited for growing families. The primary suite is a private retreat, complete with a spacious walk-in closet and a luxurious five-piece ensuite featuring an upgraded 6-foot freestanding soaker tub. Each additional bedroom enjoys convenient access to its own bathroom, while a thoughtfully designed second-floor laundry room with added cabinetry enhances everyday functionality. The lower level presents over 2,000 square feet of untapped potential-ideal for future living space, recreation, or customization to suit your needs. Perfectly positioned to offer both accessibility and tranquility, this exceptional home is just minutes to Barrie (10 minutes), Orillia (15 minutes), and nearby ski hills (7 minutes), as well as within close proximity to the brand-new Horseshoe Heights Public School and the Simcoe Woods Community Centre. No Appliances & No A/C. (id:5764)

26 Pearsall Place, Oro-Medonte

Listing courtesy of PSR.

$799,900
3 Beds ⋅ 2 Baths ⋅ S13060286 MLS® #
Charming country home and workshop, for sale in sought after Shanty Bay, Ontario. Minutes from Barrie, Hwy 11 and 400, this location can't be beat. Recently upgraded and renovated home with breathtaking deck overlooking terraced gardens and magnificent trees offering privacy and a sense of nature. The workshop has street level exposure for commercial pursuits or not, (this has been an art studio and gallery for several years.) The new Shanty Bay public school is due to open in Sept. 2027, Lake Simcoe very close for swimming and boating, many hiking trails and the rail trail very close by. The workshop (350 sq. ft.) features wide planked very old wooden floors, electrical panel, many windows. The basement of that building, also 350 sq. feet can be used for storage. The exterior stucco has been painted, new deck, stairs and railings, upgraded eaves trough with leaf guard, cedar rail fence, new retaining wall. Major renovation includes wall insulation replacements, chimney restoration and new plumbing for gas inserts, nearly all windows and doors replaced. The kitchen cupboards have been modified. Repainted, and added a dishwasher, new countertop. Cherry hardwood floors have been installed throughout most of the main floor, angel stone fireplace in the flagstone wall, beamed ceiling matches floors, main floor bath completely renovated. 2nd floor master bedroom with gas insert fireplace, new maple hardwood flooring, and a renovated 4 piece ensuite bathroom. Do whatever you'd like in the unfinished basement, with 8' ceiling and a walk out to the backyard, large windows flood that space with light. Energy efficiency has been improved with new attic insulation, 2 upgraded electrical panels, and many electrical upgrades throughout, like replacing the ceiling and adding pot lights in the dining/kitchen area. Consider this unbeatable location, in a home full of charm, while enjoying the access to every modern convenience. Click brochure link for more details. (id:5764)

2015 Ridge Road West, Oro-Medonte

Listing courtesy of .

$875,000
4 Beds ⋅ 3 Baths ⋅ S12821766 MLS® #
Welcome to 31 Tanglewood Crescent in Oro-Medonte, a beautifully maintained home offering comfort, quality updates, and a true sense of community. Set in a sought after neighbourhood known for its welcoming atmosphere and strong neighbourly connections, this is a place where families put down roots and stay. Inside, the home blends warmth and functionality with a modern layout designed for everyday living and entertaining. The open concept main level is anchored by a gas fireplace and a modern kitchen featuring updated appliances, including a refrigerator replaced in 2024 and a stove and dishwasher approximately seven years old. The walkout basement impresses with high ceilings that make the space feel bright and expansive, complete with a second gas fireplace, creating an ideal setting for a recreation room, media space, or extended family living. Heated floors in the primary bathroom and basement hallway add an elevated level of comfort, while fibre optic internet ensures seamless connectivity for work and lifestyle needs. Storage is abundant throughout the home, and the deck spanning the entire rear façade provides exceptional outdoor living space with mature trees offering privacy. Key mechanical updates include a roof completed in 2019, a high efficiency furnace installed in 2024, and several windows replaced approximately three years ago. This is a home that has provided space to grow, room to gather, and the peace that comes with living just outside the hustle while remaining connected to amenities and recreation. 31 Tanglewood Crescent delivers both lifestyle and long term value in a setting that truly feels like home. (id:5764)

31 Tanglewood Crescent, Oro-Medonte

Listing courtesy of EXP REALTY.

$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. (id:5764)

1775 Ridge Road West, Oro-Medonte

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