Lake Simcoe Waterfront Cottages

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House for sale: 913 LAKE DRIVE N, Georgina

44 photos

$1,169,000

913 Lake Drive N, Georgina (Historic Lakeshore Communities), Ontario L4P 3E9

2 beds
1 baths
21 days

Traditional charm meets modern comfort in this exceptional year-round, indirect lakefront cottage in the highly sought-after historic lakefront community of Eastbourne. Backing onto the members-only Eastbourne Golf Club and overlooking Snake Island, this rare offering is one of the community's

House for sale: 33 LAKE DRIVE E, Georgina

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$2,199,000

33 Lake Drive E, Georgina (Historic Lakeshore Communities), Ontario L4P 3E9

4 beds
2 baths
119 days

Experience exceptional lakeside living on the shores of Lake Simcoe. Set on a private oversized lot with 72 ft of indirect waterfront, this distinctive Lindal cedar residence offers architectural character, privacy, and lifestyle flexibility. Ideal for full-time living, a seasonal retreat,

House for sale: 678 LAKE DRIVE E, Georgina

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$5,999,000

678 Lake Drive E, Georgina (Historic Lakeshore Communities), Ontario L0E 1S0

14 beds
8 baths
93 days

THREE COTTAGES ON ONE PROPERTY. There Are Lakefront Properties & Then There Is Sunset Shores. Set On Approximately 1.7 Acres Of Direct Lake Simcoe Waterfront, This Extraordinary Family Compound Is A Place Where Generations Gather, Lifelong Traditions Begin & Every Evening Ends With Spectacular

House for sale: 145 LAKE DRIVE N, Georgina

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$1,448,000

145 Lake Drive N, Georgina (Keswick North), Ontario L4P 3C8

3 beds
2 baths
36 days

A Rare Blend Of Storybook Cottage Charm And Modern Urban Comfort, This Beautiful Home In Georgina Invites You To Slow Down, Breathe Deeply, And Savour Life By The Lake. Set On An Impressive Indirect Waterfront Lot With A 2nd Rear Lane Way Access, This Property Offers Room For All Your Toys

House for sale: 48 LAKE AVENUE, Ramara

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$1,199,000

48 Lake Avenue, Ramara (Rural Ramara), Ontario L0K 1B0

4 beds
2 baths
14 days

Welcome To This Beautiful Lakefront Cottage In Lagoon City, Offering Private, Direct Access ToLake Simcoe With A Coveted Western Exposure And Breathtaking Sunsets. Filled With Natural Light, The Home Features Expansive Windows And Multiple Rooms With Picturesque Water Views And Bright Light

Daniel Anthony Oliveira,Century 21 Atria Realty Inc.
Listed by: Daniel Anthony Oliveira ,Century 21 Atria Realty Inc. (416) 203-8838
House for sale: 525 LAKE DRIVE E, Georgina

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$1,299,900

525 Lake Drive E, Georgina (Historic Lakeshore Communities), Ontario L0E 1S0

2 beds
1 baths
8 days

Situated on the shores of Lake Simcoe in sought-after Willow Beach, this lovely indirect lakefront property is less than an hour from Toronto and offers a relaxed lakeside lifestyle, panoramic views and spectacular sunsets. Set on a beautiful private lot surrounded by cedar hedges, enjoy a

House for sale: 813 LAKE DRIVE E, Georgina

50 photos

$1,388,900

813 Lake Drive E, Georgina (Sutton & Jackson's Point), Ontario L0E 1L0

3 beds
3 baths
51 days

Welcome To Luxury Lakefront Living On Lake Simcoe! Nestled In The Heart Of Jackson's Point, This Stunning Custom-Built Waterfront Home Offers The Perfect Blend Of Modern Design, Comfort, And Breathtaking Views. Featuring 3 Spacious Bedrooms And 3 Bathrooms. The Main Floor Showcases Heated Floors

House for sale: 115 LAKESHORE ROAD W, Oro-Medonte

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$899,000

115 Lakeshore Road W, Oro-Medonte (Rural Oro-Medonte), Ontario L0L 2E0

1 beds
1 baths
120 days

Waterfront Escape on Lake Simcoe. Set on a 50 Ft. by 202 Ft. waterfront lot located in desirable Oro-Medonte, this winterized cottage combines rustic charm with great potential. The open-concept interior welcomes natural light and features a natural gas fireplace. Outside, a spacious deck invites

Listed by: Lily Cadeau ,Coldwell Banker The Real Estate Centre (705) 722-8191
House for sale: 10 SNAKE ISLAND ROAD, Georgina Islands

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$249,000

10 Snake Island Road, Georgina Islands (Snake Island), Ontario L4P 3E9

2 beds
1 baths
115 days

Welcome to your private waterfront escape on Snake Island. Set along a sandy shoreline with a private dock and unobstructed views of Lake Simcoe, this beautifully updated 2025/2026 cottage offers a turnkey opportunity to enjoy island life. The bright, carpet-free interior features a modern

House for sale: 2289 LAKESHORE ROAD E, Oro-Medonte

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$1,690,000

2289 Lakeshore Road E, Oro-Medonte (Rural Oro-Medonte), Ontario L0L 1T0

3 beds
3 baths
71 days

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

House for sale: 607 CEDARVALE DRIVE, Innisfil

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$1,950,000

607 Cedarvale Drive, Innisfil (Rural Innisfil), Ontario L9S 4L1

6 beds
3 baths
36 days

Big Cedar Point, Innisfil - Exceptional Lakefront Opportunity on Lake Simcoe. A rare offering at the very tip of sought-after Big Cedar Point. This premium 102 x 170 ft waterfront property presents an exceptional opportunity to own in one of Lake Simcoe's most desirable lakefront communities.

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 101 HEDGE ROAD, Georgina

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$1,299,000

101 Hedge Road, Georgina (Sutton & Jackson's Point), Ontario L0E 1L0

4 beds
2 baths
29 days

If You Have Been Waiting For An Exceptional Opportunity Along Historic Hedge Road, Your Wait Is Over! Situated On A Well-Manicured And Hedged Lot Alongside The First Fairway Of The Renowned Briars Resort, With Rare Deeded Lake Access Across The Street, This Property Is The Quintessential Cottage

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 1689 CHIEF JOSEPH SNAKE ROAD, Georgina Islands

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$349,000

1689 Chief Joseph Snake Road, Georgina Islands (Georgina Island), Ontario L0E 1R0

3 beds
1 baths
237 days

Gorgeous log cabin waterfront on Lake Simcoe on leased land within 1 hour from Toronto and the GTA. Your dream getaway awaits you. This cottage has been extremely well maintained and improved with newer underpinning, a metal roof, new water pump, an enclosed front porch for your enjoyment overlooking

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 1623 CHIEF JOSEPH SNAKE ROAD, Georgina Islands

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$350,000

1623 Chief Joseph Snake Road, Georgina Islands (Georgina Island), Ontario L0E 1R0

2 beds
1 baths
117 days

Lakeside Retreat on Georgina Island Under 1 Hour from the GTA! Escape the hustle and bustle to your own serene getaway on beautiful Georgina Island. Just under an hour from the GTA, this cozy 2-bedroom, 1-bathroom cottage offers the perfect blend of rustic charm of a cabin and modern comfort.

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 21 BEAVER TRAIL, Ramara

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$850,000

21 Beaver Trail, Ramara (Rural Ramara), Ontario L0K 1B0

3 beds
2 baths
97 days

The Ultimate Cottage or Home Package! Absolutely everything you see is included!! Even the Boat! Desired Lagoon City on a Cul de Sac location. Boasts 146' of shoreline with docking for 3 boats. Just start to vacation! Fully winterized. Municipal services. Inside this cosy home the vaulted ceiling

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 209 BAY STREET, Oro-Medonte

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$4,490,000

209 Bay Street, Oro-Medonte (Shanty Bay), Ontario L0L 2L0

5 beds
5 baths
92 days

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

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 70 IVY LANE, Orillia

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$630,000

70 Ivy Lane, Orillia (Orillia), Ontario L3V 6H1

5 beds
1 baths
57 days

Welcome to Grape Island on the north edge of Lake Simcoe, in Orillia! This little piece of heaven is located on an island, only a 2 min boat ride from mainland, and limited to 52 lots and approx. 45 cottages. 1.5h away from Toronto, Grape Island is a small community of friendly owners. Facing

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 9 - 1139 CLAVER AVENUE, Innisfil

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$439,000

9 - 1139 Claver Avenue, Innisfil (Rural Innisfil), Ontario L0L 1C0

3 beds
1 baths
57 days

1139 Claver Avenue, Cottage #9 is the largest of 12 cottages on a unique Lake Simcoe waterfront property in Belle Ewart. With three bedrooms and one newly renovated semi-ensuite 3-piece washroom this charming three-season residence features a kitchen with side-door entrance + fridge, stove/oven,

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 40630 SHORE ROAD, Brock

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$319,900

40630 Shore Road, Brock (Beaverton), Ontario L0K 1A0

3 beds
2 baths
36 days

Freehold & Mortgageable Waterfront Retreat Featuring Two Cottages And 3 separate parcels of land. Discover A Rare Island Escape Just A 3-Minute Boat Ride From Beaverton Harbour, Offering The Perfect Blend Of Privacy, Charm, And Accessibility. This Exceptional Waterfront Property Spans Over

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 3778 HARRYS LANE W, Ramara

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$1,399,900

3778 Harrys Lane W, Ramara (Rural Ramara), Ontario L3V 0L1

5 beds
3 baths
131 days

PRICE REDUCTION -Lake Simcoe! This charming four-season home/cottage sits on a desirable western exposure, offering stunning evening views you'll never tire of. Tucked along a paved road in a peaceful, close-knit community-with only 7 properties sharing the waterfront-you'll enjoy both privacy

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 2032 LAKESHORE DRIVE, Ramara

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$1,498,000

2032 Lakeshore Drive, Ramara (Rural Ramara), Ontario L0K 1B0

5 beds
4 baths
97 days

Spectacular Family Cottage with 78ft of Perfect West Facing Lake Simcoe Shoreline. Just a One Hour Drive From the Eastern End of the GTA. The Cottage Includes a 1/11 Ownership in Parcel 2023 Lakeshore Dr.(yearly maintenance fee ~$600) You'll Never Have Backlot Neighbors! Three Outbuildings

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 131 MINNETONKA ROAD, Innisfil

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$1,999,900

131 Minnetonka Road, Innisfil (Rural Innisfil), Ontario L9S 2V8

3 beds
2 baths
106 days

Imagine waking each morning to breathtaking sunrises dancing across the sparkling waters of Lake Simcoe. Set on 75 feet of pristine waterfront, this picture-perfect retreat is truly cute as a button-yet finished to a level that feels brand new. Completely renovated over the years with impeccable

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 1082 LOON ROAD, Georgina Islands

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$799,000

1082 Loon Road, Georgina Islands (Georgina Island), Ontario L0E 1R0

4 beds
4 baths
146 days

Waterfront on Lake Simcoe | 100 Ft of Shoreline & Private Guest Suite !Escape to 1082 Loon Rd and experience the perfect blend of comfort and lakeside living on the shores of Lake Simcoe. This charming bungalow-style cottage offers 100 feet of pristine eastern-facing waterfront, ideal for enjoying

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 344 LOON ROAD E, Georgina Islands

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$520,000

344 Loon Road E, Georgina Islands (Georgina Island), Ontario L0E 1R0

3 beds
1 baths
148 days

Experience the magic of this Lake Simcoe Direct Waterfront Family Cottage on the highly sought-after east side of Georgina Island. This charming winterized 3-season retreat is perfectly situated directly on your private shoreline, this 3-bedroom, 1-bath cottage is designed for making memories.

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 27440 CEDARHURST BEACH ROAD, Brock

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$8,499,900

27440 Cedarhurst Beach Road, Brock (Rural Brock), Ontario L0K 1A0

9 beds
7 baths
100 days

Award-Winning Confederation Luxury Log Home Masterpiece (Living Magazine's 2022 Log Home Of The Year) Custom Built In 2020 With 300Ft Of Direct Sandy Bottom Exclusive Waterfront Situated On A Very Private & Commanding 3.5+ Acres. Offering 9 Bedrooms & 7 Bathrooms, Complete W/10,000+ Finished

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 4787 BYERS LANE, Ramara

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$549,900

4787 Byers Lane, Ramara (Rural Ramara), Ontario L3V 0S1

3 beds
1 baths
116 days

Watch the gorgeous sunset from the deeded waterfront just seconds away across the lane. Large 80 X 191' lot. Ramara 3 br Cottage 1 hr 20 mins from Toronto. Just a 2 min walk to another clear sandy beach on Lake Simcoe. Clear water great for swimming. Next to Mara Provincial Park to explore

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 4099 GLEN CEDAR DRIVE, Ramara

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$838,000

4099 Glen Cedar Drive, Ramara (Rural Ramara), Ontario L3V 6H7

4 beds
1 baths
91 days

FULLY RENOVATED, FULLY FURNISHED, WATERFRONT, AND MOVE-IN READY! This exceptional four-season cottage offers 80 feet of direct waterfront and the perfect blend of cottage charm and modern comfort. Thoughtfully updated and meticulously maintained, the property features a newer forced-air furnace

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 2636+ LAKESHORE DRIVE, Ramara

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$1,450,000

2636+ Lakeshore Drive, Ramara (Rural Ramara), Ontario L0K 1B0

5 beds
1 baths
100 days

A rare opportunity to own a four-PIN Lake Simcoe property package in the sought-after community of Brechin - offered together as one exceptional waterfront assembly. The offering includes three separate waterfront parcels (PINs 587150104, 587150105 & 587150106) boasting approximately 151 feet

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 2389 CRYSTAL BEACH ROAD, Innisfil

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$999,999

2389 Crystal Beach Road, Innisfil (Alcona), Ontario L9S 3W8

2 beds
1 baths
100 days

Charming partially winterized Lake Simcoe cottage lovingly owned by the same family for nearly 60 years, ready for its next chapter of memories. Escape to the lake at 2389 Crystal Beach Road, a classic 1938 waterfront cottage with postcard views over Lake Simcoe and a warm, nostalgic feel throughout.

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 127 SHORELINE DRIVE, Oro-Medonte

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$1,539,900

127 Shoreline Drive, Oro-Medonte (Hawkestone), Ontario L3V 0K2

3 beds
3 baths
98 days

Peaceful. Waterfront. Timeless. Where peaceful mornings on the lake and easy access to city amenities come together. Perfectly positioned between Barrie and Orillia, this Lake Simcoe waterfront home offers the ideal balance of year-round living and cottage-style escape.Set on a quiet, year-round

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 3209 SUMMER PLACE, Innisfil

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$5,590,000

3209 Summer Place, Innisfil (Rural Innisfil), Ontario L9S 3B8

8 beds
9 baths
82 days

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

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 4298 PLUM POINT ROAD W, Ramara

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$1,198,000

4298 Plum Point Road W, Ramara (Rural Ramara), Ontario L3V 0P8

6 beds
3 baths
79 days

WELCOME TO YOUR PRIVATE LAKE SIMCOE RETREAT! Set on approx.100 feet of beautifully rebuilt granite-boulder shoreline, this extensively renovated waterfront home offers approximately 3,500 sq. ft. of bright, open-concept living space with breathtaking lake views and exceptional flexibility for

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 104 HEDGE ROAD, Georgina

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$1,995,000

104 Hedge Road, Georgina (Sutton & Jackson's Point), Ontario L0E 1R0

4 beds
3 baths
76 days

Winter Wind Cottage sits on an extra-wide waterfront lot on Hedge Road, one of Jacksons Point's most sought-after streets. Private and green, the property offers flat, usable table land that opens the door to sitting areas, family gatherings, and room for kids to play. A newly built stairway

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 2356 LAKESHORE DRIVE, Ramara

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$699,900

2356 Lakeshore Drive, Ramara (Brechin), Ontario L0K 1B0

2 beds
1 baths
76 days

Escape to the shores of beautiful Lake Simcoe with this charming 3-season waterfront cottage offering spectacular western exposure and unforgettable sunsets. Set on an impressive 75' x 204' lot with approximately 75 feet of pristine shoreline (as per GeoWarehouse), this cozy 2-bedroom retreat

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 1283 CHIEF JOSEPH SNAKE ROAD, Georgina Islands

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$649,900

1283 Chief Joseph Snake Road, Georgina Islands (Georgina Island), Ontario L0E 1R0

5 beds
2 baths
73 days

Welcome to your perfect Lake Simcoe escape. Set on over 70+feet of pristine waterfront, this cherished family cottage has been thoughtfully renovated from top to bottom in 2025, blending timeless cottage charm with modern comfort.Designed for effortless entertaining and family gatherings, the

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 9 TIKVAH CIRCLE, Georgina

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$2,195,000

9 Tikvah Circle, Georgina (Historic Lakeshore Communities), Ontario L4P 3C8

9 beds
5 baths
70 days

Welcome to a rare opportunity to own one of Balfour Beach's Iconic waterfront properties. Set on an impressive 100 feet of prime, south facing Lake Simcoe shoreline, this cherished three-season family compound has been the backdrop for generations of unforgettable summers and lifelong family

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: B40440 SHORE ROAD, Brock

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$569,000

B40440 Shore Road, Brock (Rural Brock), Ontario L0K 1A0

3 beds
1 baths
61 days

Thorah Island Retreat 81 Acres of Private Waterfront on Lake Simcoe. Escape to your own secluded paradise with this exceptional island retreat, located just a short 10-minute boat ride (approx. 3 miles) from Beaverton Harbour on beautiful Lake Simcoe. This rare offering features a pristine,

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 1125 WOODLAND DRIVE, Oro-Medonte

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$1,349,900

1125 Woodland Drive, Oro-Medonte (Rural Oro-Medonte), Ontario L3V 6H1

3 beds
2 baths
61 days

Welcome to your own private waterfront paradise, where 72 feet of pristine shoreline and crystal-clear, hard-bottom water create the perfect setting for swimming, boating, fishing, and breathtaking sunrises. This fully winterized 3-bedroom, 2-bathroom bungalow is nestled among mature trees,

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: B40854 SOUTH HARBOUR LANE, Brock

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$310,000

B40854 South Harbour Lane, Brock (Rural Brock), Ontario L0K 1A0

3 beds
1 baths
58 days

Welcome to this charming 3-bedroom seasonal Thorah Island retreat, offering the perfect blend of rustic character, cedar logs and wood accents. and thoughtful updates. Nestled on a generous 145 x 150 lot with mature trees and natural beauty, this cottage is accessible only by boat, making it

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 2674 LONE BIRCH TRAIL, Ramara

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$799,999

2674 Lone Birch Trail, Ramara (Brechin), Ontario L0K 1B0

3 beds
1 baths
52 days

A rare opportunity to own premium west-facing waterfront on Lake Simcoe, held by the same family for over 75 years. Set on a private point at the end of a quiet cul-de-sac, this pie-shaped lot offers 103 ft of clear shoreline, beautiful sunset views, and direct access to the lake for boating

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 1061 2ND LINE, Innisfil

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$499,000

1061 2nd Line, Innisfil (Rural Innisfil), Ontario L0L 1R0

2 beds
1 baths
45 days

Welcome to this charming detached cottage-style bungalow offering comfortable, easy-maintenance living in a desirable lakeside community. This 2 bedroom, 1 bathroom home features a cozy gas fireplace that efficiently heats the entire home, creating a warm and inviting atmosphere throughout

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 47 MOON POINT DRIVE, Oro-Medonte

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$749,000

47 Moon Point Drive, Oro-Medonte (Rural Oro-Medonte), Ontario L3V 0R8

2 beds
1 baths
43 days

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

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 386 BEAR ROAD, Georgina Islands

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$699,000

386 Bear Road, Georgina Islands (Georgina Island), Ontario L0E 1R0

6 beds
4 baths
43 days

Exceptional Georgina Island waterfront living on Lake Simcoe! Meticulously maintained & move-in ready! This approximately 3200 sq. ft. two storey cottage offers quiet privacy, luxurious living &, with 6 bedrooms, 4 bathrooms & two huge great rooms, space for family & friends. Accessible by

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 128 MOORES BEACH ROAD, Georgina

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$1,049,000

128 Moores Beach Road, Georgina (Virginia), Ontario L0E 1N0

5 beds
2 baths
35 days

Priced to Move with a newly cleaned waterfront! Welcome to 128 Moores Beach Road, a beautifully renovated Lake Simcoe waterfront home on a quiet private cul-de-sac. Enjoy calm waters, excellent boating and fishing, privacy, and stunning lake views. This 5-bedroom home features a custom kitchen

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 1253 RAMARA ROAD, Ramara

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$579,900

1253 Ramara Road, Ramara (Rural Ramara), Ontario L0K 1B0

2 beds
1 baths
30 days

Cozy and inviting, this charming 2-bedroom, 1-bathroom lakeside cottage offers an exceptional opportunity to enjoy life on the shores of Lake Simcoe. Perfect as a weekend retreat or a year-round residence, the home provides a warm cottage atmosphere and a fantastic entry point for first-time

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 3784 TUPPY DRIVE, Ramara

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$1,520,000

3784 Tuppy Drive, Ramara (Rural Ramara), Ontario L3V 6H7

5 beds
4 baths
22 days

Welcome to your dream lakeside retreat! Nestled on the serene shores of Lake Simcoe, this charming 4-season cottage offers the perfect blend of relaxation and modern comfort, just 90 minutes from the GTA and 20 minutes to Orillia.As you enter the open-concept main level, you are welcomed by

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 47 SHANTY BAY ROAD, Barrie

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$2,349,000

47 Shanty Bay Road, Barrie (North Shore), Ontario L4M 1C9

5 beds
3 baths
21 days

Welcome to this breathtaking waterfront property, where luxury meets location on the shores of Kempenfelt Bay. Fully renovated in 2020, this 3,000+ sq. ft. bungalow was designed to maximize spectacular lake views year-round. Blending the comfort of a home with the lifestyle of a cottage, it

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 20 SNAKE ISLAND E, Georgina Islands

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$299,900

20 Snake Island E, Georgina Islands (Snake Island), Ontario L4P 0M2

3 beds
1 baths
20 days

Well built and well maintained cottage on desirable East side of Snake Island. Very private location with incredible views from family room. Quality finishing with oak paneling and cedar strip ceilings. Wood burning wood stove with backup electric heat. Cottage is in excellent condition with

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 3458 AMILIA DRIVE, Ramara

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$998,000

3458 Amilia Drive, Ramara (Rural Ramara), Ontario L0K 1B0

4 beds
3 baths
18 days

Opportunity knocks on the beautiful shores of Lake Simcoe! Welcome to 3458 Amilia Drive, a charming lakeside retreat offering 4 bedrooms, 3 bathrooms, a spacious yard perfect for BBQs and bonfires, a fully equipped kitchen, and a comfortable living space designed for family gatherings. Located

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 1699 CHIEF JOSEPH SNAKE ROAD, Georgina Islands

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$599,000

1699 Chief Joseph Snake Road, Georgina Islands (Georgina Island), Ontario L0E 1R0

3 beds
3 baths
17 days

Welcome to turnkey waterfront living on beautiful Georgina Island! This stunning 3-bedroom, 3-bathroom bungalow offers over 1,800 sq. ft. of thoughtfully designed living space and boasts 100+ feet of direct Lake Simcoe waterfront, perfectly positioned to capture breathtaking lake views and

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668

Buying a cottage Lake Simcoe waterfront property: what informed buyers should know

For many Ontario buyers, a cottage Lake Simcoe waterfront purchase blends four-season family use with strong long-term demand. Lake Simcoe sits an easy drive from the GTA via Highways 400 and 404, offers established communities with services, and connects into the Trent–Severn system via the Atherley Narrows. Whether you're scanning cottages for sale on Lake Simcoe for personal use or evaluating income potential, success comes from understanding zoning, shoreline rules, septic and water systems, and the seasonal rhythm that shapes pricing and availability.

Why Lake Simcoe appeals: everyday convenience meets cottage life

Lake Simcoe's draw is twofold: real cottage amenities—sandy stretches, boating, and winter ice fishing—plus proximity to groceries, healthcare, and trades. Areas like Innisfil, Oro-Medonte, Georgina (Sutton, Keswick), Ramara, and Beaverton offer a range of waterfront settings from open-water exposure to quiet bays and canal networks. For example, Ramara's canal-based waterfront at Lagoon City on Lake Simcoe gives protected docking and quick lake access—useful when buyers want both boating and lower wave exposure.

From an advisory standpoint, the “everyday convenience” factor supports resale. Four-season roads, nearby marinas, and reasonable commute times tend to sustain buyer interest in all market cycles.

Cottage Lake Simcoe Waterfront: zoning, shoreline works, and permits

Lake Simcoe spans multiple municipalities and the Lake Simcoe Region Conservation Authority (LSRCA) watershed, with additional oversight by the Ministry of Natural Resources and Forestry (MNRF) and federal agencies for in-water works. Local zoning typically falls under shoreline residential/rural designations with environmental protection overlays. Setbacks and lot coverage rules can be strict near the high-water mark, and many properties are under Site Plan Control.

Boathouses and docks are heavily regulated. Some municipalities allow dry boathouses but prohibit living space, second stories, or new structures over water. In-water works may require LSRCA permits and other approvals depending on fish habitat timing windows and navigation. See a practical example of permissible improvements in a Lake Simcoe waterfront property with a boathouse; then verify the rules for your exact lot, as approvals are site-specific and can change.

Site constraints that commonly affect approvals

  • Environmental and hazard lands: floodplain mapping and erosion setbacks can limit expansions.
  • Shoreline road allowances: some waterfronts include unopened allowances your lawyer may advise you to buy or enter into agreements for, affecting where you can build.
  • Tree and shoreline alteration bylaws: vegetation removal, retaining walls, and beach creation are often restricted to protect water quality.

Buyer takeaway: Always confirm zoning, conservation authority requirements, and building permits with the local municipality and LSRCA before waiving conditions. Regulations vary by township and even by shoreline segment.

Septic, water supply, winterization, and road access

Most Lake Simcoe cottages use septic systems. Ontario Building Code governs tank and bed sizing; many municipalities require inspection on transfer or when adding bedrooms. Budget for a septic inspection, pump-out, and potential upgrades if you plan to expand. Water is often drawn from the lake with filtration/UV treatment or from a drilled well on deeper lots—both are insurable but require maintenance and seasonalization plans.

Insulation level and heat source determine whether a property is truly four-season. Look for frost-protected water lines, a heated crawlspace, and reliable heat (e.g., electric baseboards, propane furnace, or heat pump). Private roads may have winter maintenance agreements and annual fees; your lender and insurer will ask for details.

Financing, insurance, and ownership structures

Financing depends on property type. Lenders generally classify “Type A” (four-season, year-round road, potable water, permanent foundation) and “Type B” (seasonal or limited services). Type A can often be financed similar to a primary home, sometimes with mortgage default insurance through non-CMHC providers. Type B or water-access-only may require 20–35% down, shorter amortizations, and stricter insurer criteria. Rental income typically isn't considered for high-ratio second-home insurance, but conventional lenders may underwrite long-term lease income case-by-case.

Example: a winterized Innisfil bungalow on a year-round road may qualify for mainstream terms; a Ramara island cottage or three-season structure likely needs higher down payment and specialized insurance. If you're weighing different configurations—including turnkey small-lake properties like the Lucky Lake cottage example—discuss details early with your broker and lawyer. KeyHomes.ca regularly publishes financing notes and can connect buyers with lenders equipped for cottage underwriting nuances.

Short‑term rental (STR) rules and community impact

STR bylaws on Lake Simcoe are municipal, not lake-wide. The Town of Georgina, Township of Innisfil, and Township of Ramara have licensing programs with caps, compliance checks, and fees; zones and dwelling types may be restricted, noise and parking are monitored, and some communities have moratoriums or pilot programs that can change year to year. Verify with the municipality and, if applicable, your condo/canal community rules. Insurers often require explicit STR coverage and may limit occupancy.

Investors considering “lake simcoe cottages for sale waterfront” for STR income should underwrite conservative nightly rates, off-season occupancy, and compliance costs. Your neighbors' tolerance matters: canal settings differ from open-water lots for noise transmission and parking.

Resale drivers and value traps

On Lake Simcoe, buyers consistently pay premiums for: south or west exposure (sunsets), swimmable sandy or firm-bottom frontage, protected but navigable docking depth, privacy, and proximity to the 400/404. Functional septic, modern windows/insulation, and legally permitted shoreline structures help value hold in softer markets.

Factors that can suppress value: shallow weedy bays without a clear swim area, severe erosion, properties within hazard zones limiting expansion, and non-compliant additions. Canal properties (e.g., Lagoon City) trade differently than open-water frontage; they appeal to boaters and families who prioritize calm water and lower maintenance over big-lake vistas. Reviewing comparable sales via a data source like KeyHomes.ca often clarifies the right pricing lane for “lake simcoe cottages for sale,” “waterfront cottages for sale lake simcoe,” and the luxury cohort.

Market timing and seasonal patterns

Inventory builds from late winter through spring as ice-out approaches, then normalizes by mid-summer. A second wave appears late August to October as families reassess plans post-summer. Winter can bring motivated sellers, but showings are tougher and waterfront utility is harder to gauge. Expect competitive bidding on well-priced “lake simcoe luxury cottages for sale” in May–June, while shoulder-season conditions may benefit buyers seeking due diligence windows.

Search behavior reflects this cycle: phrases like “cottage for sale Lake Simcoe,” “cottages for sale Lake Simcoe,” and “cottage for sale Lake Simcoe waterfront Ontario” surge in spring. Buyers should be paperwork-ready (ID, proof of funds, lender pre‑review) ahead of peak weekends.

For‑sale‑by‑owner (FSBO) considerations

“Lake Simcoe cottages for sale by owner” appear each season. FSBO can work, but ensure: full representation in the Agreement of Purchase and Sale, verified permits for additions, septic and water potability documentation, accurate frontage measurements, and disclosure of any conservation authority notices. A boundary sketch or survey is essential around older shoreline fences or docks. Experienced representation can mitigate post‑closing surprises.

Regional comparisons and where Lake Simcoe fits

Buyers often compare Lake Simcoe to nearby and further‑afield options based on price, travel time, and water character. For big-water boating but a quieter feel, maclean lake ontario near Port Severn connects to the Trent–Severn and offers lock access and classic Canadian Shield shorelines. In Haliburton, deep, clean headwater lakes like Kennisis Lake trade at strong $/front‑foot for privacy and clarity; Kawartha favourites such as Buckhorn Lake balance lock access with family-friendly bays.

If you are exploring value pockets, Kashwakamak Lake in the Land O'Lakes region can offer larger lots at lower entry points than Lake Simcoe. Northern buyers sometimes consider options like this Lake Timmins cottage example where taxes and carrying costs differ, though access and services are more limited. Closer to the GTA but on the Great Lakes, see South Coast shorelines such as Lake Erie cottages for sandy beaches and extended shoulder seasons.

For those torn between wine-country charm and water access, Niagara's heritage setting provides a different lifestyle profile than Lake Simcoe—illustrated by a Niagara‑on‑the‑Lake cottage listing where walkability often competes with boating on the wish list. In Muskoka and surrounding districts, compact, swimmable lakes like Gull Lake deliver clarity and quick town access, while Lake Simcoe maintains the GTA‑commuter edge and broader service base.

Investor lens: income, luxury tiers, and exit strategy

Lake Simcoe supports a spectrum—from entry waterfront to “lake simcoe luxury cottages for sale” with estate footprints, boathouses, and multi‑generational layouts. For investors, durable drivers include all‑season access, strong local trades, and a broad buyer pool on exit. Underwrite conservatively: property taxes, insurance for waterfront/STR, septic maintenance, shoreline compliance, and utilities can offset summer rents. When modeling, separate personal‑use value from financial returns to avoid overpaying.

KeyHomes.ca is useful for cross‑lake comparisons—tracking “lake simcoe waterfront cottages for sale” alongside peers lets you gauge relative value and liquidity. Comparing a Simcoe canal property to an open‑water frontage, or to an inland option like the earlier small-lake turnkey example, clarifies which mix of exposure, dockage, and services aligns with your long‑term plan.