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Simcoe, ON Luxury Homes

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With Square Yards Canada, you can find your dream luxury homes for sale in Simcoe. Explore your options from condo apartments, condo townhouses, detached houses, semi detached homes posted by agencies/owners who provide spacious and luxurious amenities in luxury houses for sale in Simcoe

Last Updated: November 10, 2026

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9 Windrose Valley Boulevard, Simcoe, ON , MLS #S14107974 , Image - 1

9 Windrose Valley Boulevard Rural Clearview, Clearview, Simcoe, ON MLS® S14107974

Residential Freehold (Detached)

$2899000.0

7 +1 Beds
5 Baths
5000 + sq-ft

Spectacular executive home in the exclusive WINDROSE VALLEY ESTATES only minutes from Historic Downtown Collingwood yet has that rural feeling. Large

Open House : Sun Nov 15, 01:00 PM to 03:00 PM

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21 Buckingham Boulevard, Simcoe, ON , MLS #S14080264 , Image - 1

21 Buckingham Boulevard Rural Clearview, Clearview, Simcoe, ON MLS® S14080264

Residential Freehold (Detached)

$2095000.0

4 Beds
3 Baths
2500-3000 sq-ft

Welcome to Buckingham Woodlands-a rarely offered property close to private ski clubs, Blue Mountain Village, and downtown Collingwood. Set on approxim

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5 Buckingham Boulevard, Simcoe, ON , MLS #S14167506 , Image - 1

5 Buckingham Boulevard Rural Clearview, Clearview, Simcoe, ON MLS® S14167506

Residential Freehold (Detached)

$3495000.0

4 Beds
4 Baths
3500-5000 sq-ft

Architecture takes centre stage at this award-winning Scandinavian-inspired home by Crothers & Associates Architects. Set on a private one-acre lot al

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11 Georgian Manor Drive, Simcoe, ON , MLS #S14088822 , Image - 1

11 Georgian Manor Drive Collingwood, Simcoe, ON MLS® S14088822

Residential Freehold (Detached)

$2899000.0

4 Beds
5 Baths
2500-3000 sq-ft

A RARE WATERFRONT OFFERING WITH STYLE, SPACE & SOPHISTICATION. Rare find with double garage attached on the water. This striking home at 11 Georgian

Pre-Construction

Rosehaven Simcoe Woods

Innisfil Beach Road & Webster Boulevard

From $879,990 - $1,339,990

Project Info

Units
Townhouses

Property Mix

Floorplans coming soon

Developer:Rosehaven Homes

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2920 Concession 10 N Nottawasaga N/A, Simcoe, ON , MLS #S14165552 , Image - 1

2920 Concession 10 N Nottawasaga N/A Rural Clearview, Clearview, Simcoe, ON MLS® S14165552

Residential Freehold (Detached)

$2200000.0

3 +2 Beds
4 Baths
2500-3000 sq-ft

EXCEPTIONAL COUNTRY LIVING WITH ESCARPMENT VIEWS. A sweeping circular driveway welcomes you to this extraordinary custom-built stone bungalow, set on

Open House : Sat Nov 14, 12:00 PM to 02:00 PM

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4 Walter James Parkway, Simcoe, ON , MLS #S14167102 , Image - 1

4 Walter James Parkway Snow Valley, Springwater, Simcoe, ON MLS® S14167102

Residential Freehold (Detached)

$2499900.0

4 +1 Beds
6 Baths
2500-3000 sq-ft

Welcome to 4 Walter James Parkway. Located in the sought after Cameron Estates pocket of Snow Valley, this custom executive bungalow with loft sits on

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159 Creighton Street, Simcoe, ON , MLS #S14164894 , Image - 1

159 Creighton Street Atherley, Ramara, Simcoe, ON MLS® S14164894

Residential Freehold (Detached)

$2399900.0

3 Beds
3 Baths
3000-3500 sq-ft

Welcome to a truly special stretch of Lake Simcoe waterfront, where over an acre of privacy, beautiful sunsets and 100 feet of shoreline set the stage

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222 Oak Street, Simcoe, ON , MLS #S13701580 , Image - 1

222 Oak Street Collingwood, Simcoe, ON MLS® S13701580

Residential Freehold (Detached)

$2850000.0

Price drop by 3.4%

5 Beds
4 Baths
3500-5000 sq-ft

Welcome to 222 Oak Street, where timeless elegance meets modern luxury in this custom-built North Oak home. Set on a fenced full town lot in downtown

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339 Champlain Road, Simcoe, ON , MLS #S13732230 , Image - 1

339 Champlain Road Penetanguishene, Simcoe, ON MLS® S13732230

Residential Freehold (Detached)

$2900000.0

Price drop by 15.9%

3 Beds
4 Baths
3500-5000 sq-ft

This is one of a kind! Some properties simply exist in a category of their own. This extraordinary waterfront estate along the shores of Georgian Ba

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63 Georgian Manor Drive, Simcoe, ON , MLS #S13658890 , Image - 1

63 Georgian Manor Drive Collingwood, Simcoe, ON MLS® S13658890

Residential Freehold (Detached)

$2399000.0

Price drop by 12.8%

5 Beds
3 Baths
3000-3500 sq-ft

Wake up to spectacular sunrises, unwind with unforgettable sunsets, and enjoy panoramic 180-degree views across Nottawasaga Bay from this exceptional

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40 South Island Trail, Simcoe, ON , MLS #S14090970 , Image - 1

40 South Island Trail Rural Ramara, Ramara, Simcoe, ON MLS® S14090970

Residential Freehold (Detached)

$2290000.0

4 Beds
5 Baths
3500-5000 sq-ft

Experience Extraordinary Waterfront Living in this One-Of-A-Kind Custom Estate, Where Timeless Craftsmanship meets Today's Luxury Lifestyle. Designed

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11 Byers Street, Simcoe, ON , MLS #S14162330 , Image - 1

11 Byers Street Snow Valley, Springwater, Simcoe, ON MLS® S14162330

Residential Freehold (Detached)

$2299900.0

3 +2 Beds
4 Baths
2500-3000 sq-ft

Nestled on a PREMIUM LOT in prestigious CAMERON ESTATES, this exceptional executive bungalow offers a rare blend of LUXURY, PRIVACY, RESORT INSPIRED L

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2726 10 Nottawasaga Concession S, Simcoe, ON , MLS #S13536500 , Image - 1

2726 10 Nottawasaga Concession S Rural Clearview, Clearview, Simcoe, ON MLS® S13536500

Residential Freehold (Detached)

$3295000.0

3 Beds
3 Baths
2500-3000 sq-ft

Set on 98.6 acres of rolling fields and mature woods, Wishing Tree Farm is a private country retreat near Creemore where a beautifully renovated bunga

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1015 Lakeshore Road E, Simcoe, ON , MLS #S14161792 , Image - 1

1015 Lakeshore Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S14161792

Residential Freehold (Detached)

$2699000.0

4 Beds
4 Baths
3000-3500 sq-ft

Timeless post-and-beam architecture meets exceptional Lake Simcoe waterfront on sought-after Lakeshore Road in Hawkestone. Privately nestled among mat

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29 Mariners Haven N/A, Simcoe, ON , MLS #S14154478 , Image - 1

Unit-17, 29 Mariners Haven N/A Collingwood, Simcoe, ON MLS® S14154478

Residential Condo & Other (Condo Townhouse)

$2500000.0

3 +2 Beds
5 Baths
2500-2749 sq-ft

Experience exceptional waterfront living at 29 Mariners Haven, an extensively renovated 5-bedroom, 5-bathroom residence in one of Collingwood's most d

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2 Tessier Drive, Simcoe, ON , MLS #S14154198 , Image - 1

2 Tessier Drive Penetanguishene, Simcoe, ON MLS® S14154198

Residential Freehold (Multiplex)

$2850000.0

13 Beds
12 Baths
5000 + sq-ft

If you are looking for an absolutely turn key 12-unit apartment building, this is it. Priced at a 6.2 cap rate. This building has had extensive renova

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7272 36/37 Nottawasaga Side Road E, Simcoe, ON , MLS #S14103684 , Image - 1

7272 36/37 Nottawasaga Side Road E Rural Clearview, Clearview, Simcoe, ON MLS® S14103684

Residential Freehold (Detached)

$2399000.0

4 Beds
3 Baths
3500-5000 sq-ft

Set on 2.2 beautifully landscaped acres along the highly coveted 36/37 Side Road East, this charming country property is a rare blend of character, wa

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4767 14th Line, Simcoe, ON , MLS #N13819412 , Image - 1

4767 14th Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13819412

Residential Freehold (Detached)

$2100000.0

3 +1 Beds
3 Baths
2000-2500 sq-ft

Discover total privacy on 1.57 acres backing onto a tree-lined stream, 10 minutes to Highway 400. 4,300+ sq ft of finished living space, 8 walkouts an

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1174 Concession 10 N Nottawasaga Road, Simcoe, ON , MLS #S13862250 , Image - 1

1174 Concession 10 N Nottawasaga Road Rural Clearview, Clearview, Simcoe, ON MLS® S13862250

Residential Freehold (Detached)

$2600000.0

3 Beds
3 Baths
2500-3000 sq-ft

In 1890, a Scottish stonemason gathered limestone and fieldstone from these hills and raised a schoolhouse. Generations of children learned here, spli

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2804 9th Line, Simcoe, ON , MLS #N14151092 , Image - 1

2804 9th Line Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N14151092

Residential Freehold (Detached)

$2499900.0

5 Beds
4 Baths
3500-5000 sq-ft

Spectacular 175-year-old, 5 bedroom, 4 bathroom century home situated on a private, stunning10 acre lot featuring a picturesque pond & stream. Every a

48 Photos

1220 Shoreview Drive, Simcoe, ON , MLS #N13810126 , Image - 1

1220 Shoreview Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N13810126

Residential Freehold (Detached)

$6999900.0

4 +2 Beds
6 Baths
3500-5000 sq-ft

Welcome to this stunning luxury waterfront estate, a blend of elegant design, modern amenities, and breathtaking natural beauty. The exterior showcase

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960 Lawson Road, Simcoe, ON , MLS #S13628036 , Image - 1

960 Lawson Road Rural Tiny, Tiny, Simcoe, ON MLS® S13628036

Residential Freehold (Rural Residential)

$3890000.0

5 +2 Beds
5 Baths
3000-3500 sq-ft

THE LAWSON ESTATE. An exceptional opportunity to secure 86.99 acres in one of Southern Georgian Bay's most desirable four-season destinations, just ov

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7665 36/37 NOTTAWASAGA Side Road W, Simcoe, ON , MLS #S13496572 , Image - 1

7665 36/37 NOTTAWASAGA Side Road W Nottawa, Clearview, Simcoe, ON MLS® S13496572

Residential Freehold (Detached)

$2999000.0

Price drop by 14.3%

5 Beds
3 Baths
5000 + sq-ft

Prepare to be captivated. Set on 18 private acres overlooking the breathtaking Pretty River, this extraordinary custom-built log home is a masterpiece

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209 Bay Street, Simcoe, ON , MLS #S13508726 , Image - 1

209 Bay Street Shanty Bay, Oro-Medonte, Simcoe, ON MLS® S13508726

Residential Freehold (Detached)

$4490000.0

5 Beds
5 Baths
3000-3500 sq-ft

Rare Waterfront Estate in Prestigious Shanty BayA rare opportunity to own an exceptional waterfront retreat in the heart of Shanty Bay. Tucked away on

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291 Third Street, Simcoe, ON , MLS #S13811550 , Image - 1

291 Third Street Collingwood, Simcoe, ON MLS® S13811550

Residential Freehold (Detached)

$2375000.0

Price drop by 5.0%

5 Beds
3 Baths
3000-3500 sq-ft

**A Rare Collingwood Masterpiece - Historic Character, Modern Luxury & Unparalleled Potential!** This extraordinary 1894 red brick estate is set on a

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6 Pinehurst Lane, Simcoe, ON , MLS #S13523312 , Image - 1

6 Pinehurst Lane Anten Mills, Springwater, Simcoe, ON MLS® S13523312

Residential Freehold (Detached)

$2299900.0

Price drop by 13.2%

6 +3 Beds
6 Baths
5000 + sq-ft

A PRIVATE ESTATE. AN EXCEPTIONAL LIFESTYLE. Tucked away on a quiet cul-de-sac in desirable Springwater, just minutes from Barrie, this custom-built re

47 Photos

230 Kempview Lane, Simcoe, ON , MLS #S13636622 , Image - 1

230 Kempview Lane South Shore, Barrie, Simcoe, ON MLS® S13636622

Residential Freehold (Detached)

$2499999.0

4 Beds
4 Baths
3500-5000 sq-ft

Welcome To 230 Kempview Lane - A Stunning Custom-Built Waterfront Estate On The Prestigious Shores Of Kempenfelt Bay In Barrie. Set On A Rare Level Wa

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13 Georgina Drive S, Simcoe, ON , MLS #S14145888 , Image - 1

13 Georgina Drive S Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S14145888

Residential Freehold (Detached)

$2995000.0

3 Beds
4 Baths
2000-2500 sq-ft

Rare waterfront opportunity on Kempenfelt Bay with immediate occupancy available! Discover an exceptional opportunity to own 120 feet of beautiful wat

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1335 Flos Rd Road W, Simcoe, ON , MLS #S14141318 , Image - 1

1335 Flos Rd Road W Rural Springwater, Springwater, Simcoe, ON MLS® S14141318

Residential Freehold (Farm)

$2398000.0

3 Beds
1 Baths
2000-2500 sq-ft

Exceptional 100-Acre Property & Business Opportunity. Discover the possibilities with this unique share purchase opportunity of Smith Brothers Farm In

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9417 91 County Road, Simcoe, ON , MLS #S14087392 , Image - 1

9417 91 County Road Rural Clearview, Clearview, Simcoe, ON MLS® S14087392

Residential Freehold (Detached)

$2999000.0

4 +1 Beds
5 Baths
3000-3500 sq-ft

Set on just over three acres close to Devil's Glen and Duntroon Highlands, this custom built two storey, 6 bedroom home has quality finishes throughou

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