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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: May 07, 2026

40 Photos

2705 14th Line, Simcoe, ON , MLS #N12495028 , Image - 1

2705 14th Line Gilford, Innisfil, Simcoe, ON MLS® N12495028

Residential Freehold (Detached)

$2290000.0

Price drop by 9.7%

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

Welcome to an extraordinary custom-built estate designed for true multi-generational living or potential rental income. Set on a private 3.25-acre tre

40 Photos

24 Finley Drive, Simcoe, ON , MLS #S13091062 , Image - 1

24 Finley Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13091062

Residential Freehold (Detached)

$2625000.0

2 +3 Beds
4 Baths
3500-5000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Custom waterfront home featuring 4,066 square feet above ground and 5,899 total, while being nestled on a do

40 Photos

3298 Seydel Lane, Simcoe, ON , MLS #S13068632 , Image - 1

3298 Seydel Lane Rural Severn, Severn, Simcoe, ON MLS® S13068632

Residential Freehold (Detached)

$3498000.0

5 Beds
4 Baths
3000-3500 sq-ft

Executive Waterfront Retreat on Gloucester Pool. Located on the Trent Severn Waterway, one Lock to Georgian Bay. Escape to luxury with this stunning 5

50 Photos

74 Lakeside Drive, Simcoe, ON , MLS #N13077204 , Image - 1

74 Lakeside Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N13077204

Residential Freehold (Detached)

$2199000.0

4 Beds
3 Baths
1500-2000 sq-ft

Own a Timeless Waterfront Retreat in Prime Big Bay Point. Just one hour from the energy of Toronto, The Lake House offers a rare opportunity to own a

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

40 Photos

6 Pinehurst Lane, Simcoe, ON , MLS #S13050494 , Image - 1

6 Pinehurst Lane Anten Mills, Springwater, Simcoe, ON MLS® S13050494

Residential Freehold (Detached)

$2749900.0

6 +3 Beds
6 Baths
5000 + sq-ft

Experience the ultimate retreat in this stunning custom-built estate, perfectly positioned on a private 1.62-acre lot just minutes from Barrie. Design

39 Photos

5834 Second Line, Simcoe, ON , MLS #N13059550 , Image - 1

5834 Second Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13059550

Residential Freehold (Detached)

$2250000.0

5 +1 Beds
6 Baths
3500-5000 sq-ft

Set on 5 private acres just 10 minutes north of Nobleton, this custom stone-and-brick estate is the kind of property that gives you more than just a b

49 Photos

8058 20th Side Road, Simcoe, ON , MLS #N12876938 , Image - 1

8058 20th Side Road Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N12876938

Residential Freehold (Detached)

$2650000.0

Price drop by 3.6%

3 +2 Beds
3 Baths
2000-2500 sq-ft

A property where space, privacy, and lifestyle come together in one remarkable setting. Set behind gates on 21.62 pristine acres, this private country

50 Photos

214 Hickory Lane, Simcoe, ON , MLS #S12769920 , Image - 1

214 Hickory Lane Bayshore, Barrie, Simcoe, ON MLS® S12769920

Residential Freehold (Detached)

$2499900.0

3 +1 Beds
4 Baths
2500-3000 sq-ft

One of a kind luxury private estate nestled in the heart of Barrie on just under 3 acres backing onto Environmental Protected land & Hewitt's creek! C

41 Photos

1359 Old Barrie Road E, Simcoe, ON , MLS #S13021978 , Image - 1

1359 Old Barrie Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13021978

Residential Freehold (Detached)

$2199900.0

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

Highest Quality From Top To Bottom Over 5000 SqFt Of Available Living Space, South Western Exposure Backyard For Beautiful Sunsets. One Of A Kind It F

32 Photos

158 Dale Crescent, Simcoe, ON , MLS #N13076898 , Image - 1

158 Dale Crescent Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13076898

Residential Freehold (Detached)

$2500000.0

4 Beds
4 Baths
3500-5000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Executive, custom-built bungaloft in an exclusive estate neighbourhood, perfectly positioned and backing ont

40 Photos

7833 Poplar Side Road, Simcoe, ON , MLS #S12758960 , Image - 1

7833 Poplar Side Road Rural Clearview, Clearview, Simcoe, ON MLS® S12758960

Residential Freehold (Detached)

$2999000.0

4 +3 Beds
8 Baths
3000-3500 sq-ft

Welcome to an extraordinary 14.95-acre country estate that defines luxury living in the heart of Collingwood. Just minutes from downtown yet surrounde

23 Photos

10 White Oaks Road, Simcoe, ON , MLS #S13070218 , Image - 1

10 White Oaks Road South Shore, Barrie, Simcoe, ON MLS® S13070218

Residential Freehold (Detached)

$3350000.0

5 Beds
4 Baths
3000-3500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Experience true waterfront living with over 91 feet of pristine sandy shoreline, enhanced by a steel retaini

9 Photos

3869 7th Line, Simcoe, ON , MLS #N13067006 , Image - 1

3869 7th Line Rural Innisfil, Innisfil, Simcoe, ON MLS® N13067006

Residential Freehold (Farm)

$3500000.0

4 Beds
3 Baths
2500-3000 sq-ft

Prime 78.8-acre agricultural property on paved 7th Line, Innisfil, ideally located between the Village of Thornton and the rapidly growing Innisfil Be

46 Photos

58 White Oaks Road, Simcoe, ON , MLS #S13063796 , Image - 1

58 White Oaks Road South Shore, Barrie, Simcoe, ON MLS® S13063796

Residential Freehold (Detached)

$2125000.0

4 Beds
3 Baths
3000-3500 sq-ft

Welcome to a truly one of a kind opportunity to own a prime piece of waterfront real estate nestled along the sandy shores of Kempenfelt Bay. This lar

40 Photos

130 Concession 15 N/A W, Simcoe, ON , MLS #S12984964 , Image - 1

130 Concession 15 N/A W Rural Tiny, Tiny, Simcoe, ON MLS® S12984964

Residential Freehold (Detached)

$2499900.0

4 Beds
3 Baths
3500-5000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Escape the limitations of the city with this 40-acre private compound in Tiny, offering a scale of infrastru

50 Photos

28 Alana Drive, Simcoe, ON , MLS #S12791854 , Image - 1

28 Alana Drive Centre Vespra, Springwater, Simcoe, ON MLS® S12791854

Residential Freehold (Detached)

$2099900.0

4 Beds
3 Baths
3500-5000 sq-ft

A private backyard retreat with a heated saltwater pool, multiple seating areas, and mature landscaping - ideal for relaxing, hosting friends, or spen

13 Photos

2781 Sixth Line, Simcoe, ON , MLS #N12681098 , Image - 1

2781 Sixth Line Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N12681098

Residential Freehold (Detached)

$2699000.0

5 Beds
2 Baths
2000-2500 sq-ft

A prime investment opportunity to acquire 1.631 acres of land located at the main entrance of Bradford's largest upcoming residential subdivision with

40 Photos

3935 3rd Line, Simcoe, ON , MLS #N13048378 , Image - 1

3935 3rd Line Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13048378

Residential Freehold (Detached)

$4800000.0

4 Beds
3 Baths
3500-5000 sq-ft

Nestled on 99 acres of countryside, this extraordinary estate offers a perfect blend of functionality, and natural beauty. Designed with the horse ent

1 Photos

00000 George Avenue Wasaga Beach, Simcoe, ON MLS® S13042710

Residential Freehold (Vacant Land)

$2350000.0

< 700 sq-ft

Attention Developers - 10.3 Acres Development Land. Zoned D for development (can include Residential and Commercial development). The World's Longest

47 Photos

15 Palm Beach Road, Simcoe, ON , MLS #S13035232 , Image - 1

15 Palm Beach Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13035232

Residential Freehold (Detached)

$2399999.0

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

Set along the pristine shores of Lake Simcoe, this exceptional waterfront estate offers a rare blend of privacy, prestige, and resort style living, pe

19 Photos

359-363 Duckworth Street, Simcoe, ON , MLS #S13032490 , Image - 1

359-363 Duckworth Street Grove East, Barrie, Simcoe, ON MLS® S13032490

Residential Freehold (Other)

$13850000.0

99 +45 Beds
64 Baths
5000 + sq-ft

Rare student housing investment opportunity in Barrie, offering immediate cash flow. This offering includes two well-maintained, purpose-built apartme

48 Photos

1220 Shoreview Drive, Simcoe, ON , MLS #N13039442 , Image - 1

1220 Shoreview Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N13039442

Residential Freehold (Detached)

$7250000.0

4 +2 Beds
5 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

50 Photos

2280 Highway 27 N/A, Simcoe, ON , MLS #N13003894 , Image - 1

2280 Highway 27 N/A Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13003894

Residential Freehold (Detached)

$4190000.0

4 +2 Beds
5 Baths
5000 + sq-ft

Welcome To 2280 Hwy 27 Bradford. A Private Luxury Retreat On 10 Acre Land With 7500 Sqft Of Living Space. Detached 6 Bedroom House, 5 Washrooms, Finis

30 Photos

47 Glen Road, Simcoe, ON , MLS #S12905046 , Image - 1

47 Glen Road Collingwood, Simcoe, ON MLS® S12905046

Residential Freehold (Detached)

$2150000.0

3 Beds
3 Baths
3000-3500 sq-ft

Outstanding waterfront residence in Collingwood! Spectacular panoramic waterfront views from this custom-built home close to the finest amenities thi

50 Photos

3531 Crescent Harbour Road, Simcoe, ON , MLS #N13026976 , Image - 1

3531 Crescent Harbour Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N13026976

Residential Freehold (Detached)

$3599000.0

3 +2 Beds
4 Baths
1500-2000 sq-ft

This exceptional 2011 custom-built home with over 3,000 sq ft of finished living space offers the perfect blend of modern luxury and classic cottage c

40 Photos

376 Brewery Lane, Simcoe, ON , MLS #S13026480 , Image - 1

376 Brewery Lane Orillia, Simcoe, ON MLS® S13026480

Residential Freehold (Detached)

$4799000.0

3 +2 Beds
5 Baths
3500-5000 sq-ft

Welcome to 376 Brewery Lane, a stunning luxury waterfront home situated on one of Orillias finest streets. This exceptional property offers 104 feet o

7 Photos

7528 County Road, Simcoe, ON , MLS #N12024509 , Image - 1

Unit-14, 7528 County Road Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N12024509

Residential Freehold (Detached)

$2400000.0

3 Beds
2 Baths
1100-1500 sq-ft

Charming Raised Bungalow Sitting On 25 Acres, 7 Acres Trees & Meadows, 18 Acres Workable Farmland, Trout Stream (Bailey Creek), Walking & Riding Trail

47 Photos

202 Kempenfelt Drive, Simcoe, ON , MLS #S13018404 , Image - 1

202 Kempenfelt Drive North Shore, Barrie, Simcoe, ON MLS® S13018404

Residential Freehold (Detached)

$2290000.0

4 Beds
4 Baths
3000-3500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Welcome to 202 Kempenfelt Drive, an extraordinary custom-built residence completed in 2020, ideally located

48 Photos

130 Dale Crescent, Simcoe, ON , MLS #N13014780 , Image - 1

130 Dale Crescent Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13014780

Residential Freehold (Detached)

$2499000.0

3 +1 Beds
5 Baths
2500-3000 sq-ft

Welcome to 130 Dale Crescent, a modern bungalow set on a private 1.5-acre lot backing onto a protected forest. Large floor-to-ceiling windows, vaulted

40 Photos

6643 3rd Line, Simcoe, ON , MLS #N12562584 , Image - 1

6643 3rd Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N12562584

Residential Freehold (Detached)

$2999000.0

5 +1 Beds
6 Baths
3500-5000 sq-ft

This stunning 6-bedroom, 6-bathroom bungalow on 10 acres just north of King offers luxurious living with the convenience of nearby amenities. The prop

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