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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: March 31, 2026

40 Photos

6 Pinehurst Lane, Simcoe, ON , MLS #S12937482 , Image - 1

6 Pinehurst Lane Anten Mills, Springwater, Simcoe, ON MLS® S12937482

Residential Freehold (Detached)

$2988000.0

6 +3 Beds
6 Baths
5000 + sq-ft

Experience the ultimate retreat in this stunning custom-built estate, perfectly positioned on a private 1.64-acre lot just minutes from Barrie. Design

41 Photos

3965 Algoma Avenue, Simcoe, ON , MLS #N12937336 , Image - 1

3965 Algoma Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N12937336

Residential Freehold (Detached)

$2699000.0

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

Luxury Custom Bungaloft on Shoreline Road - Steps to Lake Simcoe! ****Welcome to this newly upgraded, move-in-ready custom bungaloft situated on a rar

48 Photos

130 Dale Crescent, Simcoe, ON , MLS #N12867548 , Image - 1

130 Dale Crescent Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N12867548

Residential Freehold (Detached)

$2716345.0

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

25 Photos

8747 10th Line, Simcoe, ON , MLS #N12935984 , Image - 1

8747 10th Line Rural Essa, Essa, Simcoe, ON MLS® N12935984

Residential Freehold (Detached)

$2195000.0

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

OVER 3,000 SQ FT BUNGALOW FEATURING IN-LAW POTENTIAL NESTLED ON 83.47 ACRES WITH WORKABLE LAND & MINUTES TO BARRIE! Nestled on an expansive 83.47 acre

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

37 Photos

750 Tiny Beaches Road S, Simcoe, ON , MLS #S12935366 , Image - 1

750 Tiny Beaches Road S Rural Tiny, Tiny, Simcoe, ON MLS® S12935366

Residential Freehold (Detached)

$2600000.0

3 +0 Beds
1 Baths
700-1100 sq-ft

75 feet frontage on a truly spectacular beach. This all season cottage is situated in a prime location on coveted Wymbolwood Beach - highly regarded

21 Photos

1114 Goshen Road E, Simcoe, ON , MLS #N12915688 , Image - 1

1114 Goshen Road E Alcona, Innisfil, Simcoe, ON MLS® N12915688

Residential Freehold (Detached)

$9800000.0

4 Beds
3 Baths
1500-2000 sq-ft

1114 Goshen RD - 4.7 acres of land with income-generating apartments ripe and ready for zoning amendment and development. Zoned FD - Future Developmen

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)

$2750000.0

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

Set behind gates on 21.62 pristine acres, this private country estate offers the rare combination of usable land, impressive outbuildings, and a beaut

35 Photos

3476 Garden Of Eden Road, Simcoe, ON , MLS #S12660608 , Image - 1

3476 Garden Of Eden Road Rural Clearview, Clearview, Simcoe, ON MLS® S12660608

Residential Freehold (Farm)

$3999999.0

7 Beds
7 Baths
5000 + sq-ft

Set on an extraordinary 50-acre parcel just minutes from the heart of Creemore, this exceptional executive home offers refined living surrounded by a

35 Photos

1614 Ridge Road E, Simcoe, ON , MLS #S6142920 , Image - 1

1614 Ridge Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S6142920

Residential Freehold (Multiplex)

$3299000.0

Price drop by 1.8%

6 Beds
5 Baths
5000 + sq-ft

Welcome To 'Hawkstone Manor' In Old Charm Historical Hawkestone, Oro-Medonte. First Time Offer For Sale After Completing A Full Preservation Of This U

40 Photos

1918 Concession Rd 2 N/A, Simcoe, ON , MLS #N12412220 , Image - 1

1918 Concession Rd 2 N/A Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N12412220

Residential Freehold (Detached)

$2750000.0

6 Beds
3 Baths
2500-3000 sq-ft

Exceptional opportunity to own 100 acres of prime countryside in the heart of South Adjala, just minutes to Caledon and surrounded by prestigious esta

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

46 Photos

58 White Oaks Road, Simcoe, ON , MLS #S12564712 , Image - 1

58 White Oaks Road South Shore, Barrie, Simcoe, ON MLS® S12564712

Residential Freehold (Detached)

$2149000.0

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

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

40 Photos

190 MELISSA Lane, Simcoe, ON , MLS #S12899946 , Image - 1

190 MELISSA Lane Rural Tiny, Tiny, Simcoe, ON MLS® S12899946

Residential Freehold (Detached)

$3280000.0

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

Welcome to 190 Melissa Lane, a charming custom built French Inspired waterfront retreat nestled in the prestigious community of Cedar Ridge, Tiny, Ont

41 Photos

1359 Old Barrie Road E, Simcoe, ON , MLS #S12684820 , Image - 1

1359 Old Barrie Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S12684820

Residential Freehold (Detached)

$2299900.0

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

Highest Quality From Top To Bottom Over 5000SqFt Of Available Living Space, South Western Exposure Backyard. One Of A Kind It Factor Family Home on 37

50 Photos

53 Dock Lane, Simcoe, ON , MLS #S12676364 , Image - 1

Unit-27, 53 Dock Lane Port McNicoll, Tay, Simcoe, ON MLS® S12676364

Residential Freehold (Detached)

$2199900.0

Price drop by 4.3%

4 Beds
3 Baths
3000-3500 sq-ft

Welcome to Port McNicoll's best - kept secret, Exclusive community, serene peninsula on Georgian Bay, offering an unparallel waterfront living. This s

32 Photos

7 Meadowlark Way, Simcoe, ON , MLS #S12891620 , Image - 1

7 Meadowlark Way Collingwood, Simcoe, ON MLS® S12891620

Residential Freehold (Detached)

$3500000.0

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

MODERN, ORGANIC & TIMELESS CUSTOM-BUILT BUNGALOW FEATURING OVER 5,500 SQFT OF COMFORT-DRIVEN LIVING SPACE! A rare modern estate minutes from downtown

18 Photos

767 Cedarvale Drive, Simcoe, ON , MLS #N12890686 , Image - 1

767 Cedarvale Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N12890686

Residential Freehold (Detached)

$2399999.0

4 Beds
4 Baths
3500-5000 sq-ft

Fabulous sun filled layout with a spectacular gourmet kitchen, with Thermador appliances. Family room with 32ft soaring cathedral ceilings. Custom lar

50 Photos

2230 Spring Street, Simcoe, ON , MLS #N12804174 , Image - 1

2230 Spring Street Alcona, Innisfil, Simcoe, ON MLS® N12804174

Residential Freehold (Detached)

$3399000.0

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

40 Photos

3298 Seydel Lane, Simcoe, ON , MLS #S12843540 , Image - 1

3298 Seydel Lane Rural Severn, Severn, Simcoe, ON MLS® S12843540

Residential Freehold (Detached)

$3798000.0

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

20 Photos

1536 Tiny Beaches Road N, Simcoe, ON , MLS #S11896365 , Image - 1

1536 Tiny Beaches Road N Rural Tiny, Tiny, Simcoe, ON MLS® S11896365

Residential Freehold (Detached)

$3399000.0

4 Beds
1 Baths
700-1100 sq-ft

*** Visit the REALTOR website for further information about this Listing *** Your opportunity to own an awesome four season waterfront beach house wit

50 Photos

19 Reid's Ridge, Simcoe, ON , MLS #S12849496 , Image - 1

19 Reid's Ridge Moonstone, Oro-Medonte, Simcoe, ON MLS® S12849496

Residential Freehold (Detached)

$2199900.0

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

This extraordinary estate, set on 8.6 acres, offers a thoughtfully designed layout that blends luxury, privacy, and functionality. Originally built as

50 Photos

215 Dock Road, Simcoe, ON , MLS #S12857956 , Image - 1

215 Dock Road South Shore, Barrie, Simcoe, ON MLS® S12857956

Residential Freehold (Detached)

$2995000.0

4 +1 Beds
5 Baths
5000 + sq-ft

Welcome to your dream home, just steps from Kempenfelt Bay! This exceptional 4+1 bedroom detached home is nestled in one of Barrie's most exclusive ar

50 Photos

113 Minnetonka Road, Simcoe, ON , MLS #N12857748 , Image - 1

113 Minnetonka Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N12857748

Residential Freehold (Detached)

$2495000.0

3 Beds
1 Baths
1100-1500 sq-ft

MOVE IN TOMORROW FULLY FURNISHED! Beautiful Waterfront Property in Big Bay Point! Over 1/2 acre with unobstructed views of Lake Simcoe from almost eve

40 Photos

8870 County 93 Road, Simcoe, ON , MLS #S12350615 , Image - 1

8870 County 93 Road Midland, Simcoe, ON MLS® S12350615

Residential Freehold (Farm)

$4990000.0

Price drop by 15.4%

3 Beds
2 Baths
2500-3000 sq-ft

Great development opportunity on HWY 93 in Midland. Sewers and water are going to be coming across this property in the near future. Potential for com

33 Photos

331 Tornado Drive, Simcoe, ON , MLS #N12106179 , Image - 1

331 Tornado Drive Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12106179

Residential Freehold (Farm)

$2900000.0

Price drop by 3.3%

3 +1 Beds
1 Baths
1100-1500 sq-ft

Welcome to 331 Tornado Dr, Nestled in the Quiet Farming Community of Bradford West Gwillimbury. This residential farmland is a terrific opportunity fo

50 Photos

8429 Poplar Side Road, Simcoe, ON , MLS #S12840642 , Image - 1

8429 Poplar Side Road Rural Clearview, Clearview, Simcoe, ON MLS® S12840642

Residential Freehold (Detached)

$3299000.0

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 Osler Bluff Ski C

11 Photos

4065 15th Line, Simcoe, ON , MLS #N12822184 , Image - 1

4065 15th Line Rural Innisfil, Innisfil, Simcoe, ON MLS® N12822184

Residential Freehold (Farm)

$5499000.0

< 700 sq-ft

Top 5 Reasons You Will Love This Property: 1) Exceptional land banking and future development opportunity with 137.5-acres of prime land adjacent to d

21 Photos

8464 6th Line, Simcoe, ON , MLS #N12638712 , Image - 1

8464 6th Line Rural Essa, Essa, Simcoe, ON MLS® N12638712

Residential Freehold (Detached)

$2500000.0

4 Beds
3 Baths
3500-5000 sq-ft

TIMBER-FRAME ESTATE ON 10 ACRES WITH INGROUND POOL, EXPANSIVE BARN, VERSATILE OUTBUILDINGS, & A 4,544 SQ FT HOME BUILT TO IMPRESS! Call it a farmhouse

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

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