minPriceVal

maxPriceVal

minSize

maxSize

Simcoe, ON Luxury Homes

Showing results 1 - 30 of 236

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: October 11, 2026

50 Photos

5385 8 Line N, Simcoe, ON , MLS #S13628286 , Image - 1

5385 8 Line N Moonstone, Oro-Medonte, Simcoe, ON MLS® S13628286

Residential Freehold (Detached)

$3399000.0

5 +2 Beds
6 Baths
5000 + sq-ft

FAMILY COMPOUND | Built in 2022, this expansive 9,000 sqft estate on 100 acres is ideal for multi-generational living, family compound use, or rental

50 Photos

404 Cox Mill Road, Simcoe, ON , MLS #S13673290 , Image - 1

404 Cox Mill Road South Shore, Barrie, Simcoe, ON MLS® S13673290

Residential Freehold (Detached)

$2048000.0

3 +1 Beds
4 Baths
3000-3500 sq-ft

Golden Sunsets And Expansive Lake Views Define This Custom-Built Modern Residence In Barrie's Sought-After South Shore. Designed With Intention, This

44 Photos

290 Tollendal Mill Road, Simcoe, ON , MLS #S13801320 , Image - 1

290 Tollendal Mill Road South Shore, Barrie, Simcoe, ON MLS® S13801320

Residential Freehold (Detached)

$4700000.0

6 +0 Beds
7 Baths
5000 + sq-ft

One-of-a-kindArriscrate clad stone mansion showcasing classic design,old-world craftsmanship approx 12,000sqft of luxurious living space.Private 150x3

46 Photos

11 Byers Street, Simcoe, ON , MLS #S13756856 , Image - 1

11 Byers Street Snow Valley, Springwater, Simcoe, ON MLS® S13756856

Residential Freehold (Detached)

$2399900.0

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 and resort-inspire

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

50 Photos

2230 Spring Street, Simcoe, ON , MLS #N13694042 , Image - 1

2230 Spring Street Alcona, Innisfil, Simcoe, ON MLS® N13694042

Residential Freehold (Detached)

$2449000.0

4 Beds
2 Baths
2000-2500 sq-ft

Tucked away at the end of a quiet cul-de-sac just off Innisfil Beach Road, just under 2 Acres, this property offers a rare level of privacy and the pe

37 Photos

1814 Quantz Crescent, Simcoe, ON , MLS #N13881400 , Image - 1

1814 Quantz Crescent Rural Innisfil, Innisfil, Simcoe, ON MLS® N13881400

Residential Freehold (Detached)

$2098000.0

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

OVER 4,600 FINISHED SQ FT ON 2.2+ TREED ACRES WITH AN IN-GROUND POOL, WALKOUT LOWER LEVEL & TRIPLE GARAGE! More than 4,600 finished sq ft unfolds acro

50 Photos

95 Spruce Street, Simcoe, ON , MLS #S13880226 , Image - 1

95 Spruce Street Rural Tiny, Tiny, Simcoe, ON MLS® S13880226

Residential Freehold (Detached)

$2899900.0

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

Set on a beautifully private one-acre estate surrounded by mature forest, this exceptional custom-built 2023 residence offers a rare combination of mo

43 Photos

156 Bartlett Boulevard, Simcoe, ON , MLS #S13838906 , Image - 1

156 Bartlett Boulevard Collingwood, Simcoe, ON MLS® S13838906

Residential Freehold (Detached)

$3950000.0

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

Client RemarksWelcome to your dream waterfront oasis in Collingwood, Ontario. This stunning home offers the rare luxury of docking your boat right at

38 Photos

21 Trails End, Simcoe, ON , MLS #S13875828 , Image - 1

21 Trails End Collingwood, Simcoe, ON MLS® S13875828

Residential Freehold (Detached)

$2149000.0

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

A rare opportunity where the value of the land, setting and outdoor environment is immediately apparent. Set on a nearly one-acre double lot in presti

49 Photos

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

1174 10 Nottawasaga Concession 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

50 Photos

8672 County Rd 91 Road, Simcoe, ON , MLS #S13736848 , Image - 1

8672 County Rd 91 Road Rural Clearview, Clearview, Simcoe, ON MLS® S13736848

Residential Freehold (Detached)

$2875000.0

5 Beds
4 Baths
2000-2500 sq-ft

Luxury Estate where timeless craftsmanship meets modern elegance. Nestled on over 4 acres of picturesque countryside, this custom-built 5-bedroom, 4-b

32 Photos

7 Meadowlark Way, Simcoe, ON , MLS #S13726820 , Image - 1

7 Meadowlark Way Collingwood, Simcoe, ON MLS® S13726820

Residential Freehold (Detached)

$3500000.0

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

A CONTEMPORARY ESTATE DESIGNED FOR ELEVATED FOUR-SEASON LIVING! Set on 1.21 acres in Windrose Estates, an estate enclave of custom homes on large prop

43 Photos

31 Loftus Road, Simcoe, ON , MLS #S13871874 , Image - 1

31 Loftus Road Rural Springwater, Springwater, Simcoe, ON MLS® S13871874

Residential Freehold (Detached)

$4200000.0

6 Beds
5 Baths
5000 + sq-ft

REFINED ESTATE LIVING IN ONE OF SPRINGWATER'S PREMIER ENCLAVES! Past the gated stone entrance, 31 Loftus Road unfolds across 2.85 private acres in pre

48 Photos

5376 County 15 Road, Simcoe, ON , MLS #N13117684 , Image - 1

5376 County 15 Road Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13117684

Residential Freehold (Detached)

$2299000.0

Price drop by 20.0%

4 Beds
2 Baths
2000-2500 sq-ft

52.9 Acres with a lovely farmhouse and drive shed located in Adjala-Tosorontio township, but adjacent to New Tecumseth with beautiful panoramic views

50 Photos

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

Open House - Saturday October 3 - 1-3pm. Set on 98.6 acres of rolling fields and mature woods, Wishing Tree Farm is a private country retreat near Cre

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

50 Photos

40 South Island Trail, Simcoe, ON , MLS #S13564130 , Image - 1

40 South Island Trail Rural Ramara, Ramara, Simcoe, ON MLS® S13564130

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

40 Photos

2464 15th Side Road, Simcoe, ON , MLS #N13847280 , Image - 1

2464 15th Side Road Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13847280

Residential Freehold (Detached)

$4499000.0

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

Spectacular Private Gated Country Estate. Designed & Completed in 2021 This Fortress Encompasses The Tranquility Of The Natural Beauty Of This 9 Acre

13 Photos

8971 McKinnon Road, Simcoe, ON , MLS #N13737126 , Image - 1

8971 McKinnon Road Angus, Essa, Simcoe, ON MLS® N13737126

Residential Freehold (Vacant Land)

$2999900.0

Top 5 Reasons You Will Love This Property: 1) Encompassing just under 200-acres of mature forest across two distinct parcels in Essa Township, this ra

50 Photos

442 Silver Birch Drive, Simcoe, ON , MLS #S13100612 , Image - 1

442 Silver Birch Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13100612

Residential Freehold (Detached)

$2100000.0

Price drop by 8.7%

2 +2 Beds
3 Baths
1100-1500 sq-ft

Welcome to The Cove-a place where relaxed waterfront living meets refined comfort. Built in 2013 and meticulously maintained, this inviting bungalow o

50 Photos

60 River Avenue Crescent, Simcoe, ON , MLS #S13628334 , Image - 1

60 River Avenue Crescent Wasaga Beach, Simcoe, ON MLS® S13628334

Residential Freehold (Detached)

$2299999.0

6 +1 Beds
5 Baths
3000-3500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Exceptional riverfront property featuring four self-contained units, ideally located just minutes from the m

41 Photos

1619 Houston Avenue, Simcoe, ON , MLS #N13707880 , Image - 1

1619 Houston Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13707880

Residential Freehold (Detached)

$3999999.0

Price drop by 2.4%

3 Beds
4 Baths
3500-5000 sq-ft

For the discerning buyer seeking something beyond the ordinary, this is Lake Simcoe living without compromise. Set along the coveted shoreline of Hous

40 Photos

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

Open House : Sun Oct 11, 11:00 AM to 01:00 PM

50 Photos

4761 9th Line, Simcoe, ON , MLS #N13873768 , Image - 1

4761 9th Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13873768

Residential Freehold (Detached)

$2750000.0

4 Beds
3 Baths
3000-3500 sq-ft

Custom Bauhaus style Red Steel + Concrete constructed mansion tucked away on 6.07 tree-lined acres offering gorgeous panoramic conservation views from

26 Photos

3194 Simcoe County Road 89 N/A, Simcoe, ON , MLS #N13869718 , Image - 1

3194 Simcoe County Road 89 N/A Rural Innisfil, Innisfil, Simcoe, ON MLS® N13869718

Residential Freehold (Farm)

$3500000.0

4 Beds
1 Baths
1500-2000 sq-ft

Discover a rare 58.8-acre farm opportunity in progressive Innisfil Township, ideally positioned along County Road 89 and extending back to Innisfil Co

50 Photos

3964 Guest Road, Simcoe, ON , MLS #N13845598 , Image - 1

3964 Guest Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N13845598

Residential Freehold (Detached)

$5750000.0

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

Top 5 Reasons You Will Love This Home: 1) Experience an extraordinary Lake Simcoe lifestyle with 124' of pristine waterfront, a private dock and boat

40 Photos

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

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

Residential Freehold (Detached)

$2599000.0

Price drop by 1.9%

6 +3 Beds
6 Baths
5000 + sq-ft

Experience the ultimate retreat in this stunning custom-built estate on a private 1.62-acre lot minutes from Barrie. Designed for discerning buyers se

2 Photos

6863a Fifth Line, Simcoe, ON , MLS #N13588156 , Image - 1

6863a Fifth Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13588156

Residential Freehold (Farm)

$2500000.0

< 700 sq-ft

Exceptional Power of Sale / Receivership opportunity to acquire a combined - (6863a 10.16 and 6863 89.46) and Adjacent 99.62 acres of contiguous, larg

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

15 Photos

0 Simcoe County Road 89 N/A, Simcoe, ON , MLS #N13869714 , Image - 1

0 Simcoe County Road 89 N/A Rural Innisfil, Innisfil, Simcoe, ON MLS® N13869714

Residential Freehold (Vacant Land)

$2200000.0

3000-3500 sq-ft

RARE 28.8-ACRE AGRICULTURAL & INVESTMENT OPPORTUNITY - COUNTY ROAD 89. Exceptional opportunity featuring 28.8 acres of productive, tiled black loam fa

Shortlisted Properties

Error

Maximum 4 project can be compared at one go.

Simcoe, ON Luxury Homes

Rosehaven Simcoe Woods

Property Types Available in Simcoe

Bedroom Types Available in Simcoe

Properties By Budget in Simcoe

Top Neighbourhood in Simcoe