Lake Simcoe Waterfront Cottages

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House for sale: 33 LAKE DRIVE E, Georgina

27 photos

$2,199,000

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

4 beds
2 baths
73 days

Cross Streets: Woodbine & Lake Drive East. ** Directions: Woodbine North to Lake Drive East. 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,

House for sale: 48 LAKE AVENUE, Ramara

25 photos

$1,199,000

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

4 beds
2 baths
62 days

Cross Streets: Laguna Ave & Simcoe Rd. ** Directions: As Per Google Maps. Welcome To This Beautiful Lakefront Cottage In Lagoon City, Offering Private, Direct Access To Lake Simcoe With A Coveted Western Exposure And Breathtaking Sunsets. Filled With Natural Light, The Home Features Expansive

Daniel Anthony Oliveira,Century 21 Atria Realty Inc.
Listed by: Daniel Anthony Oliveira ,Century 21 Atria Realty Inc. (416) 203-8838
House for sale: 678 LAKE DRIVE E, Georgina

50 photos

$5,999,000

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

14 beds
8 baths
47 days

Lake Dr E & Lyons Lane 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

House for sale: 145 LAKE DRIVE N, Georgina

48 photos

$1,498,000

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

3 beds
2 baths
12 days

Lake Dr N & Old Homestead Rd 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

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
5 days

Brule Lake Way/Lake Dr E 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

House for sale: 607 CEDARVALE DRIVE, Innisfil

42 photos

$2,150,000

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

6 beds
3 baths
97 days

Cross Streets: St Johns Rd. ** Directions: In the cul de sac at Big Cedar Point. 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

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 115 LAKESHORE ROAD W, Oro-Medonte

25 photos

$899,000

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

1 beds
1 baths
74 days

Cross Streets: Line 7 South/Lakeshore Rd. W. ** Directions: Oro-Medonte 5th Line S/Lakeshore Rd. W. 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

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 2289 LAKESHORE ROAD E, Oro-Medonte

48 photos

$1,690,000

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

3 beds
3 baths
25 days

Cross Streets: Hwy 11/Line 11. ** Directions: HWY 11 to S Line 11 to Lake. 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

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 24690 THORAH PARK BOULEVARD, Brock

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$739,000

24690 Thorah Park Boulevard, Brock (Beaverton), Ontario L0K 1A0

3 beds
1 baths
6 days

Thorah Concession 2 & Durham Reg Rd 23 Enjoy beautiful sunsets from this whimsical 3-bedroom seasonal cottage filled with wonderful memories. Situated on a private waterfront lot, this home features spectacular west-facing views highlighting Lake Simcoe's famous sunsets. The cottage has been

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

50 photos

$1,329,000

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

4 beds
2 baths
25 days

Hedge Rd & Lake Dr E Situated on a well-manicured and hedged lot alongside the first fairway of the renowned Briars Golf Club, with deeded lake access a few doors down (shared with only a few neighbours), this property is the quintessential cottage where location really is everything! Enjoy

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

50 photos

$349,000

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

3 beds
1 baths
191 days

Cross Streets: North End Chief Joseph Snake. ** Directions: Ferry to Chief Joseph Snake Rd. 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

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

37 photos

$350,000

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

2 beds
1 baths
71 days

Cross Streets: CHIEF JOSEPH SNAKE RD. ** Directions: FERRY TO GEORGINA ISLAND / STRAIGHT TO 1623 CHIEF JOSEPH SNAKE RD. 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

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

30 photos

$379,000

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

3 beds
2 baths
58 days

BEAVERTON HARBOUR TO THORAH ISLAND 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

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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$898,000

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

3 beds
2 baths
51 days

Cross Streets: HWY 12/ Lagoon City. ** Directions: HWY 12/Brechin/West at Lagoon City entrance/right on Laguna Pkwy/2nd complex on right/Woodland Shores 1. The Ultimate Cottage or Home Package! Absolutely everything you see is included!! Even the Boat! Desired Lagoon City on a Cul de Sac location.

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

42 photos

$4,490,000

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

5 beds
5 baths
46 days

Cross Streets: Ridge/Line 2. ** Directions: Ridge Road to Line 2 South To Bay. 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

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

24 photos

$630,000

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

5 beds
1 baths
11 days

Cross Streets: Victoria/Forest. ** Directions: Grape Island. 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,

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

21 photos

$499,000

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

3 beds
1 baths
11 days

Cross Streets: Maple/Ewart/Claver. ** Directions: South of Ewart. 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

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 2644 LAKESHORE DRIVE, Ramara

50 photos

$899,000

2644 Lakeshore Drive, Ramara (Rural Ramara), Ontario L0K 1B0

3 beds
1 baths
166 days

Hwy 12 to Ramara Rd. 47 Turn West to Lakeshore Dr. To The Sign Your Direct Lakefront Cottage With Spectacular West Exposure, Sunsets Are Waiting and Crystal Clear Water! With Sand Bottom Incredible For Those Likes Long Days In The Sun. Close To Shopping & Amenities.Metal Roof, Vinyl Siding,

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

49 photos

$1,498,000

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

5 beds
4 baths
51 days

Cross Streets: Lakeshore Dr & Concession Rd 1. ** Directions: GPS it!. 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

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

19 photos

$1,399,900

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

5 beds
3 baths
85 days

Cross Streets: hwy 12 and Concession 7, Brechin. ** Directions: Hwy 12 north of Brechin, w on conc 7, right on sideroad 20, left on Bonnie Beach Road, left on edgehill Road, Right on Harrys Lane to 3778. PRICE REDUCTION -Lake Simcoe! This charming four-season home/cottage sits on a desirable

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

21 photos

$599,900

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

2 beds
1 baths
61 days

Cross Streets: west of Hwy 12 Btw Conc 9 & Conc A. ** Directions: Apple or Google Maps. 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,

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 579 DUCLOS POINT ROAD, Georgina

23 photos

$1,399,999

579 Duclos Point Road, Georgina (Virginia), Ontario L0E 1N0

3 beds
1 baths
22 days

Moores Beach Rd/Duclos Point POWER OF SALE - Direct Private 70+ Feet of Waterfront Access and Docking In Highly Desirable and Private Duclos Point Community. The Duclos Point Community offers a 5 Acre Park With Tennis Courts, Basketball Courts, Boat Launch and Waterfront Accesses for a $300.00

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

35 photos

$1,750,000

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

5 beds
4 baths
124 days

Cross Streets: Muley Point Rd. & Bonnie Beach Rd. ** Directions: Hwy 12 to Muley Point Rd. Follow To End. Turn Right to Bonnie Beach Rd. to Edgehill to Tuppy Drive. Welcome to your dream lakeside retreat! Nestled on the serene shores of Lake Simcoe, this charming 4-season cottage offers the

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

38 photos

$1,999,900

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

3 beds
2 baths
60 days

Cross Streets: Big Bay Point and 25th Sideroad. ** Directions: Big Bay Point to the end. Right on Minnetonka Road. 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

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

50 photos

$799,000

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

4 beds
4 baths
100 days

Cross Streets: LOON/BEAR. ** Directions: STRAIGHT FROM FERRY, RIGHT ON BEAR RD, LEFT ON LOON RD. 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

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

34 photos

$548,800

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

3 beds
1 baths
102 days

Cross Streets: Off Ferry turn right on Bear Road to 344 Loon Road. ** Directions: 404 North to, Woodbine Ave North to Sutton, East Take Ferry from Virginia Beach/ Boondocks restaurant (7751 Black River Rd). Once off the Ferry turn right on to Bear Road to 344 Loon Road. Experience the magic

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 182 BAYSHORE DRIVE, Ramara

37 photos

$1,288,000

182 Bayshore Drive, Ramara (Rural Ramara), Ontario L0K 1B0

3 beds
3 baths
61 days

Barnstable Dr (Sideroad 20) and Bayshore Dr Welcome to 182 Bayshore Dr, a stunning waterfront retreat in sought-after Bayshore Village on Lake Simcoe. This approximate 3000 ft home/cottage offers 3 bedrooms, 3 bathrooms, and breathtaking lake views with multiple walkouts for seamless indoor/outdoor

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

50 photos

$8,499,900

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

9 beds
7 baths
54 days

Concession Rd 4/Highway 23 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,

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

33 photos

$829,000

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

2 beds
1 baths
73 days

Woodland Dr & Moon Point Dr Prime Lake Simcoe waterfront on a sought-after stretch of shoreline, offering 100 feet of pristine frontage with crystal-clear water, natural rocky shoreline, and a hard sandy/rock bottom ideal for swimming, boating, and enjoying lake life. Whether you choose to

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 3934 LAKEVIEW ROAD, Innisfil

42 photos

$799,000

3934 Lakeview Road, Innisfil (Rural Innisfil), Ontario L9S 2V5

3 beds
2 baths
55 days

Cross Streets: Big Bay Point Rd/Lakeview Rd. ** Directions: Big Bay Point Road to Lakeview Road. DEEDED WATER ACCESS ON LAKE SIMCOE! Whether you're searching for a year-round home or the perfect cottage retreat, this charming bungalow offers the ideal blend of comfort, convenience, and waterfront

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 20 CANAL STREET W, Georgina

31 photos

$1,429,000

20 Canal Street W, Georgina (Keswick South), Ontario L4P 1K5

4 beds
3 baths
67 days

Cross Streets: Ravenshoe and The Queensway's. ** Directions: Ravenshoe And Canal. Rare Opportunity To Own A Beautifully Renovated 4-Bedroom Waterfront Home On A Quiet Dead-End Street! Enjoy Direct Access To Deep Water With Brand Steel Posts-Perfect For Boating And Cottage-Style Living. Bright

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

18 photos

$549,900

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

3 beds
1 baths
70 days

Cross Streets: Byers lane and Whitney. ** Directions: Courtland to Whitney to Byers lane. 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

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 10 SNAKE ISLAND ROAD, Georgina Islands

48 photos

$249,000

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

2 beds
1 baths
69 days

Lake Drive at East Point Marina 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

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
45 days

Cross Streets: Muley Point Rd & Mcrae Park Rd. ** Directions: Muley Point R & Mcrae Park Rd. 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

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 61 IRVING DRIVE, Georgina

50 photos

$1,288,000

61 Irving Drive, Georgina (Pefferlaw), Ontario L0E 1N0

3 beds
2 baths
56 days

Hwy 48 & Riverview Beach Rd Custom-built 2,000+ sq ft raised bungalow on a quiet street. Extra-deep lot backing onto a canal w/ direct access to Pefferlaw River & Lake Simcoe. Features a bright, open-concept living/dining layout, large windows, pot lights, 9' ceilings & elegant crown moulding

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: LOT 238 SNAKE ISLAND, Georgina Islands

50 photos

$350,000

Lot 238 Snake Island, Georgina Islands (Snake Island), Ontario L4P 3E9

4 beds
1 baths
34 days

Cross Streets: WOODBINE & LAKE DR N. ** Directions: GO TO EAST POINT MARINA 967 LAKE DR N - PARK THERE - TAKE WATER TAXI TO LOT 238 SNAKE ISLAND. WATERFRONT COTTAGE WITH 94' WATERFRONT & SANDY BOTTOM BEACH AREA & A GREAT VIEW ~ SNAKE ISLAND OFFERS COMMUNITY ~ ONLY ONE HOUR FROM DOWNTOWN TORONTO

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

45 photos

$1,450,000

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

5 beds
1 baths
54 days

Cross Streets: Concession Rd 3 & Lakeshore Rd. ** Directions: Concession Rd 3 to Lakeshore Rd. 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

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

42 photos

$1,049,000

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

5 beds
2 baths
54 days

Cross Streets: Hwy 48 & Duclos Point. ** Directions: Take 48 to Duclos follow along to Moores Beach. Sign on Property. Looking for the perfect waterfront home or cottage on Lake Simcoe? Here are 5 reasons you'll love 128 Moores Beach Road: 1. Exceptional Lake Simcoe Waterfront SettingNestled

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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$1,200,000

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

2 beds
1 baths
54 days

Cross Streets: Roberts/Crystal Beach. ** Directions: 25 Sideroad North to Roberts, go East to Crystal Beach Road. 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

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

42 photos

$1,539,900

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

3 beds
3 baths
52 days

Line 13 S/Shoreline Dr 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

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: B40548 SHORE ROAD, Brock

42 photos

$359,000

B40548 Shore Road, Brock (Rural Brock), Ontario L0K 1A0

4 beds
2 baths
37 days

Cross Streets: Thorah Island/ Shore Rd. ** Directions: Beaverton Harbour/Thorah Island. Beautiful Thorah Island, Lake Simcoe. This exceptional freehold waterfront cottage offers the privacy, natural beauty, and relaxed pace of island living, all just a short boat ride from Beaverton Harbour.

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

50 photos

$5,590,000

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

8 beds
9 baths
36 days

Cross Streets: Mapleview Drive and Fleming Blvd. ** Directions: Mapleview Dr to Fleming Blvd to Summer Place. 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

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

50 photos

$1,298,000

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

6 beds
3 baths
33 days

HWY12 & PLUM POINT RD 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

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

38 photos

$1,995,000

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

4 beds
3 baths
30 days

Cross Streets: Lake Dr. East and Hedge Rd. ** Directions: Ask Google :). 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,

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

8 photos

$699,900

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

2 beds
1 baths
30 days

Cross Streets: Lakeshore Dr. / Conc. Rd 2. ** Directions: Hwy 12 N,Turn left onto Concession Road, Turn right onto Ramara Road 47, Turn left onto Concession Rd 2, Turn right onto Lakeshore Dr. Escape to the shores of beautiful Lake Simcoe with this charming 3-season waterfront cottage offering

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

38 photos

$649,900

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

5 beds
2 baths
27 days

Georgina Island 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

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: LOT 50, Georgina Islands

44 photos

$289,900

Lot 50, Georgina Islands (Fox Island), Ontario L4P 3E9

3 beds
1 baths
27 days

Cross Streets: NA. ** Directions: Island Grove (East Point) Marina, Water Taxi to Lot 50 Fox Island. Escape to your own slice of paradise on the highly sought-after south shore of Fox Island! This charming direct waterfront family cottage on Lake Simcoe is situated on a land lease lot with

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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$649,000

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

3 beds
3 baths
25 days

Cross Streets: CHIEF JOSEPH SNAKE RD. ** Directions: STRAIGHT OFF FERRY FOLLOW CHIEF JOSEPH SNAKE RD. 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+

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

40 photos

$2,195,000

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

9 beds
5 baths
24 days

Balfour Beach Road and Metro Road North 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

Darya StrilyanaSutton Group Innovative Realty Inc.Agent: Darya Strilyana Sutton Group Innovative Realty Inc. 647-896-7668
House for sale: 126 MOORE'S BEACH ROAD, Georgina

50 photos

$1,299,000

126 Moore's Beach Road, Georgina (Virginia), Ontario L0E 1N0

4 beds
2 baths
22 days

Cross Streets: Duclos Point Road/Hwy 48. ** Directions: Hwy 48 to Duclos Point to Moore's Beach. Welcome to your own piece of paradise on the highly sought-after south shore of Lake Simcoe in the prestigious Duclos Point community. This beautifully updated year-round waterfront home offers

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.