Simcoe, ON Luxury Homes For Sale | SquareYards

44 Photos

1 Windrose Valley Boulevard, Simcoe, ON , MLS #S13065468 , Image - 1

1 Windrose Valley Boulevard Rural Clearview, Clearview, Simcoe, ON MLS® S13065468

Residential Freehold (Detached)

$2999000.0

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

Highly desirable location at the base of the escarpment, moments from Osler Bluff Ski Club and just minutes to downtown Collingwood, this extraordinar

50 Photos

2314 Concession 8 South Nottawasaga N/A, Simcoe, ON , MLS #S13804094 , Image - 1

2314 Concession 8 South Nottawasaga N/A Rural Clearview, Clearview, Simcoe, ON MLS® S13804094

Residential Freehold (Rural Residential)

$5400000.0

4 +1 Beds
5 Baths
3500-5000 sq-ft

Springhill Farm is a remarkable architectural country retreat set on approximately 50 private acres in the hills of Clearview. Designed by Jim Campbel

41 Photos

1359 Old Barrie Road E, Simcoe, ON , MLS #S13710136 , Image - 1

1359 Old Barrie Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13710136

Residential Freehold (Detached)

$2099900.0

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

50 Photos

2280 Simcoe County Road 27 N/A, Simcoe, ON , MLS #N13479332 , Image - 1

2280 Simcoe County Road 27 N/A Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13479332

Residential Freehold (Detached)

$3899999.0

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

44 Photos

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

48 Photos

1942 Ingram Road, Simcoe, ON , MLS #S13799822 , Image - 1

1942 Ingram Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13799822

Residential Freehold (Detached)

$2695000.0

4 Beds
5 Baths
3500-5000 sq-ft

This grand two story home has a walkout basement and 3 oversized garages. On 20 Acres Across From Copepland Forest. 2000Sq Ft Indoor Pool Room, with h

50 Photos

4229 Wilson Point Road N, Simcoe, ON , MLS #S13466754 , Image - 1

4229 Wilson Point Road N Rural Severn, Severn, Simcoe, ON MLS® S13466754

Residential Freehold (Detached)

$2499000.0

4 Beds
6 Baths
3500-5000 sq-ft

Commanding one of the finest lots on Lake Couchiching, this exceptional waterfront estate is positioned at the end of a quiet dead-end street, offerin

50 Photos

3219 Hampshire Mills Line, Simcoe, ON , MLS #S13786308 , Image - 1

3219 Hampshire Mills Line Rural Severn, Severn, Simcoe, ON MLS® S13786308

Residential Freehold (Detached)

$2600000.0

5 Beds
5 Baths
3000-3500 sq-ft

Set on 1.4 acres, this exceptional five-bedroom estate offers over 6,400 sq. ft. of finished living space, thoughtfully expanded and renovated with a

50 Photos

8429 Poplar Side Road, Simcoe, ON , MLS #S13796118 , Image - 1

8429 Poplar Side Road Rural Clearview, Clearview, Simcoe, ON MLS® S13796118

Residential Freehold (Detached)

$2999900.0

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

Welcome to The Great Totem House, a stunning reclaimed timber frame chalet set on a private 1.3-acre forested lot, just minutes from OslerBluff Ski Cl

50 Photos

3316 Point Bush Court, Simcoe, ON , MLS #S13082362 , Image - 1

3316 Point Bush Court Port Severn, Severn, Simcoe, ON MLS® S13082362

Residential Freehold (Detached)

$2699000.0

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

Where waterfront living meets everyday comfort, this custom-built four-season retreat sits on a picturesque point of land on Little Lake, offering sou

7 Photos

3125 14th Line, Simcoe, ON , MLS #N13675204 , Image - 1

3125 14th Line Rural Innisfil, Innisfil, Simcoe, ON MLS® N13675204

Residential Freehold (Vacant Land)

$6999000.0

Price drop by 22.2%

236 acre, irregular shaped property - 2,300 linear ft direct frontage on Hwy 400 just south of Hwy 89 (Tanger Outlet Mall), Great Location for future

50 Photos

2166 10th Side Road, Simcoe, ON , MLS #N13791364 , Image - 1

2166 10th Side Road Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13791364

Residential Freehold (Detached)

$3248800.0

6 +1 Beds
9 Baths
5000 + sq-ft

Generational Living at it's finest in Bradford's exclusive area. 2min to HWY 400. Feel the magnificence of this one of a kind property the second you

45 Photos

846 Sixth Street, Simcoe, ON , MLS #S13563542 , Image - 1

846 Sixth Street Rural Clearview, Clearview, Simcoe, ON MLS® S13563542

Residential Freehold (Detached)

$2499000.0

4 +4 Beds
7 Baths
3500-5000 sq-ft

Luxury Custom Home with Income Suite - Over 6,000 Sq Ft of Finished Living SpaceDiscover this stunning, one-of-a-kind luxury custom home, perfectly si

44 Photos

2710 Nottawasaga 10 Concession N, Simcoe, ON , MLS #S13593190 , Image - 1

2710 Nottawasaga 10 Concession N Rural Clearview, Clearview, Simcoe, ON MLS® S13593190

Residential Freehold (Detached)

$3975000.0

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

Introducing Winterbrook, a luxurious custom estate home masterfully crafted by Dalton Beachli. Nestled on just under two acres of beautifully landscap

29 Photos

5512 3rd Line, Simcoe, ON , MLS #N13786040 , Image - 1

5512 3rd Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13786040

Residential Freehold (Detached)

$2895000.0

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

Just north of Schomberg and east of Tottenham sits this 50+ acre parcel that is ideal for those wanting to add land to their real estate portfolio or

49 Photos

1409 CONCESSION ROAD 7 N/A, Simcoe, ON , MLS #N13783058 , Image - 1

1409 CONCESSION ROAD 7 N/A Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13783058

Residential Freehold (Rural Residential)

$3900000.0

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

EQUESTRIAN AND THOROUGHBRED HORSE FARM. This 24.979-acre farm is an Equestrian dream! Less than 15mins from Caledon Equestrian Park & 30mins from Wood

48 Photos

51 Kempenfelt Drive, Simcoe, ON , MLS #S13781022 , Image - 1

51 Kempenfelt Drive North Shore, Barrie, Simcoe, ON MLS® S13781022

Residential Freehold (Detached)

$2398000.0

2 +1 Beds
4 Baths
3000-3500 sq-ft

A striking architectural presence in one of Barrie's most beautiful waterfront settings, this contemporary residence enjoys unobstructed views over Ke

40 Photos

10 Lundy Lane, Simcoe, ON , MLS #S13697056 , Image - 1

10 Lundy Lane Rural Tiny, Tiny, Simcoe, ON MLS® S13697056

Residential Freehold (Detached)

$2450000.0

3 Beds
3 Baths
2000-2500 sq-ft

Welcome to Georgian Blue! Experience refined beachfront living in this exceptional Cape Cod waterfront retreat with over 3000 sf of finished living sp

32 Photos

678 13th Line, Simcoe, ON , MLS #N13780734 , Image - 1

678 13th Line Rural Innisfil, Innisfil, Simcoe, ON MLS® N13780734

Residential Freehold (Detached)

$4800000.0

2 Beds
2 Baths
2000-2500 sq-ft

RARE 2.26-ACRE CORNER PROPERTY ALONG FRIDAY HARBOUR GOLF GREENS. Prime 2.265-acre residential holding with dual frontage on 13th Line and Friday Drive

11 Photos

3568 4 Line, Simcoe, ON , MLS #N12641382 , Image - 1

3568 4 Line Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N12641382

Residential Freehold (Vacant Land)

$3500000.0

Are you ready to turn your real estate dreams into reality? Presenting a golden opportunity for savvy investors - a sprawling piece of vacant land nes

49 Photos

3674 Ferretti Court, Simcoe, ON , MLS #N13747854 , Image - 1

3674 Ferretti Court Rural Innisfil, Innisfil, Simcoe, ON MLS® N13747854

Residential Freehold (Att/Row/Townhouse)

$2499900.0

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

Exceptional end unit with almost 3,600 sq ft of above-grade living space, this expansive Ferretti waterfront townhome is one of the largest footprint

50 Photos

7314 Summerland Road, Simcoe, ON , MLS #S13726014 , Image - 1

7314 Summerland Road Rural Ramara, Ramara, Simcoe, ON MLS® S13726014

Residential Freehold (Detached)

$4200000.0

6 Beds
4 Baths
3500-5000 sq-ft

***95 FT OF LAKE COUCHICHING WATERFRONT LUXURY CUSTOM BUNGALOW*** Experience exceptional four-season waterfront living in this stunning custom-built b

1 Photos

3525 Tenth Line Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13770818

Residential Freehold (Detached)

$3880000.0

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

Discover an exceptional opportunity to acquire up to 20 acres of prime land in the highly sought-after Bradford West Gwillimbury area**. Ideally posit

50 Photos

1301 County Road 50 Road, Simcoe, ON , MLS #N13760460 , Image - 1

1301 County Road 50 Road Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13760460

Residential Freehold (Detached)

$3499000.0

7 +3 Beds
9 Baths
5000 + sq-ft

Welcome to a rare offering where luxury meets privacy, nestled on approximately 2.5 acres of fully gated land just minutes from Caledon. This exceptio

44 Photos

8562/8587 6th Line, Simcoe, ON , MLS #N13529158 , Image - 1

8562/8587 6th Line Rural Essa, Essa, Simcoe, ON MLS® N13529158

Residential Freehold (Farm)

$2900000.0

4 Beds
2 Baths
1500-2000 sq-ft

Discover an exceptional opportunity to own 99 acres of prime agricultural land in the heart of Essa Township, offered as two separately deeded parcels

37 Photos

4 Raintree Court, Simcoe, ON , MLS #S13594758 , Image - 1

4 Raintree Court Rural Clearview, Clearview, Simcoe, ON MLS® S13594758

Residential Freehold (Detached)

$4995000.0

4 +1 Beds
7 Baths
5000 + sq-ft

Welcome to the extraordinary, four season resort experience offered by 4 Raintree Court, nestled in the heart of Ontario's ski country. This luxurious

50 Photos

250 Gordon Drive, Simcoe, ON , MLS #S13568450 , Image - 1

250 Gordon Drive Penetanguishene, Simcoe, ON MLS® S13568450

Residential Freehold (Detached)

$4750000.0

Price drop by 4.9%

2 +3 Beds
5 Baths
5000 + sq-ft

Perched along pristine waters, this property is one of south-east Georgian Bay's most iconic waterfront estates. Built in 2007, the breathtaking 9,000

40 Photos

2292 Shore Lane, Simcoe, ON , MLS #S13747030 , Image - 1

2292 Shore Lane Wasaga Beach, Simcoe, ON MLS® S13747030

Residential Freehold (Detached)

$3200000.0

4 Beds
5 Baths
3500-5000 sq-ft

Imagine stepping outside your back door and finding yourself on 57 feet of Georgian Bay shoreline. This isn't just a house with a water view, it's a r

45 Photos

12 WHEELHOUSE Crescent, Simcoe, ON , MLS #S13735694 , Image - 1

12 WHEELHOUSE Crescent Collingwood, Simcoe, ON MLS® S13735694

Residential Condo & Other (Condo Townhouse)

$2300000.0

4 +0 Beds
4 Baths
2750-2999 sq-ft

This spectacular waterfront condo in The Shipyards offers 3,591 square feet of finished living space across three storeys of luxury construction, with

26 Photos

5 17th Street N, Simcoe, ON , MLS #S13744486 , Image - 1

5 17th Street N Wasaga Beach, Simcoe, ON MLS® S13744486

Residential Freehold (Detached)

$2600000.0

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

A MASTERPIECE OF COASTAL PRESTIGE DIRECTLY ON GEORGIAN BAY! Pull through the gated entry and Georgian Bay unfolds before you, creating a waterfront es

Simcoe, ON Luxury Homes - P5

Rosehaven Simcoe Woods

Property Types Available in Simcoe

Bedroom Types Available in Simcoe

Properties By Budget in Simcoe

Top Neighbourhood in Simcoe