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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.

209 Bay Street, Oro-Medonte
1450 Line 3 N/A N, Oro-Medonte
$3,699,999
6 Beds ⋅ 5 Baths ⋅ S13566402 MLS
Top 5 Reasons You Will Love This Home: 1) Set on 48 breathtaking acres in the highly sought-after Oro-Medonte, this exceptional custom-built ICF home offers unmatched privacy and a true lifestyle escape, where peaceful country living meets the convenience of being just a short drive to Barrie, Lake Simcoe, golf courses, ski hills, and everyday amenities 2) Dream setting for hobbyists or entrepreneurs, the property features an impressive 40'x80' detached workshop alongside an oversized triple-car garage, creating endless possibilities for storing vehicles, recreational toys, or operating a home-based business with ease 3) Inside, the stunning open-concept main level welcomes you with soaring cathedral ceilings, rich cherry hardwood flooring underfoot, and a striking floor-to-ceiling stone wood-burning fireplace that anchors the great room, complemented by three spacious bedrooms designed for comfort and style 4) The fully finished basement delivers incredible versatility with in-floor heating powered by a newer boiler, complete with a self-contained in-law suite featuring a separate entrance, two bedrooms, a full kitchen, generous living space, and its own laundry, making it ideal for extended or multi-generational living 5) Surrounded by beautifully landscaped grounds with inground sprinklers, the outdoor space is equally impressive with a composite deck and sleek glass railings, a charming clay oval pizza oven, natural gas service for added convenience, and numerous exterior upgrades, including new fascia, soffits, and downspouts, creating the perfect backdrop for both relaxing and entertaining. 3,020 above grade sq.ft. plus a finished basement. *Please note some images have been virtually staged to show the potential of the home.

1450 Line 3 N/A N, Oro-Medonte
49 Red Oak Crescent, Oro-Medonte
$1,349,000
8 Beds ⋅ 4 Baths ⋅ S13607350 MLS
Rarely offered in the highly sought-after Shanty Bay community, this exceptional residence at 49 Red Oak Crescent presents a rare opportunity to own a beautifully maintained family home offering outstanding privacy, complete with an impressive gated entrance and an expansive lot just minutes from the lake. Offering over 4,600 sq. ft. of sun-filled living space, this impressive home seamlessly blends comfort, functionality, and thoughtful upgrades throughout. Designed with large families and multi-generational living in mind, the home features an ideal layout with two bedrooms on the main floor, two spacious bedrooms on the upper level, and four additional bedrooms in the fully finished basement featuring high ceilings and upgraded vinyl flooring. The spacious primary suite includes a large walk-in closet and a beautifully updated ensuite with double vanities. Expansive principal rooms and abundant natural light create a warm and inviting atmosphere perfect for both everyday living and entertaining. The professionally landscaped backyard, with over $50,000 invested in outdoor improvements, provides a stunning outdoor setting ideal for relaxing or hosting gatherings, while a premium pool table valued at approximately $25,000 is included with the home. Additional upgrades include a new furnace and hot water tank (2025) and roof replacement (2022), offering peace of mind for years to come. This special property has also been professionally reviewed by a Feng Shui master and comes with certification, adding a unique and meaningful touch to the home's already exceptional appeal. Surrounded by serene natural beauty and located just a 4-minute drive to the lake, this remarkable property offers the perfect balance of luxury, privacy, and convenience in one of Oro-Medonte's most peaceful and family-friendly neighbourhoods. Motivated Seller.

49 Red Oak Crescent, Oro-Medonte
11 Basswood Circle, Oro-Medonte
$1,299,999
5 Beds ⋅ 4 Baths ⋅ S13759884 MLS
Tucked away in the serene landscape of Oro-Medonte, 11 Basswood Circle is a one-of-a-kind 3+2 bedroom, 4-bathroom bungaloft that captures the essence of a modern mountain retreat while offering refined everyday living. Set on a picturesque property with a spacious three-car garage, this home blends organic textures with striking architectural design, creating a warm yet sophisticated atmosphere. Expansive windows flood the home with natural light, highlighting soaring ceilings and a stunning open-concept layout.The heart of the home features a beautifully designed kitchen and living space that seamlessly connects for entertaining, while rich natural materials give the home its signature cabin-inspired feel. The main floor primary suite offers a private retreat with a luxurious 5-piece ensuite. Above, the lofted second level overlooks the main floor, adding architectural drama and an airy sense of space.The fully finished basement expands the living area with two additional bedrooms and versatile space ideal for guests, recreation, or a home gym.Over $200,000 has been invested in thoughtful upgrades, ensuring both style and long-term quality. The exterior was extensively renovated in 2025 with new stucco, new windows, and a new roof, enhancing both curb appeal and energy efficiency. Additional features include a permanent backup generator and connection for a secondary backup generator, providing added peace of mind year-round. The home is further backed by a 50-year roof warranty, lifetime window warranty, and pest-proof warranty. As an added bonus, the property is being offered partially furnished, including a pool table, dining table, backyard furniture, yard tools, and a boat.Surrounded by nature yet designed for modern living, this home is ideal for families, with access to highly rated schools including Shanty Bay Public School and nearby Montessori schools. A rare offering where lifestyle, design, and tranquility meet.

11 Basswood Circle, Oro-Medonte
13 Windfield Drive W, Oro-Medonte
$848,000
S13721208 MLS
A Rare Opportunity To Build Your Dream Home In One Of Shanty Bay's Most Exclusive Enclaves. Nestled On Coveted Windfields Drive at the end of a Cul-De-Sac, This Exceptional Building Lot (approx. 2.29 acres) Offers The Opportunity To Create A Beautiful Custom Residence In An Established Neighbourhood Surrounded By Impressive Estate Homes. One of the Last Remaining Lots Available on the Street! Just Steps From The Shores Of Lake Simcoe, The Property Offers An Enviable Four-Season Lifestyle With Easy Access To Boating, Beaches, Trails, Golf And Skiing. Architectural Plans Are Available For A Thoughtfully Designed Residence, Offering Buyers A Head Start On Bringing Their Vision To Life. Enjoy The Tranquility And Privacy Of Oro-Medonte Living While Remaining Just Minutes From Barrie, Highway 400 And Everyday Amenities. A Truly Special Setting For Those Looking To Build A Custom Home In A Quiet, Established And Highly Sought-After Community.

13 Windfield Drive W, Oro-Medonte