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Detached Houses for Sale in Simcoe Under $5M

Showing results 1 - 30 of 737

Square Yards Canada can assist you in finding the ideal detached homes in Simcoe. Browse the options of several detached homes for sale Under $5M in Simcoe comprising 1 to 5 beds. The detached houses for sale Under $5M in Simcoe are listed by owners and brokers offering first-rate amenities and services in upscale neighbourhoods in Simcoe.

Last Updated: December 18, 2025

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

50 Photos

118 Highland Drive, Simcoe, ON , MLS #S12508372 , Image - 1

118 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S12508372

Residential Freehold (Detached)

$1150000.0

2 +1 Beds
4 Baths
2500-3000 sq-ft

Welcome to 118 Highland Drive, Oro-Medonte. Discover the charm and craftsmanship of this stunning log home in the heart of Horseshoe Valley. Featured

27 Photos

24 Parr Boulevard, Simcoe, ON , MLS #S12629482 , Image - 1

24 Parr Boulevard Rural Springwater, Springwater, Simcoe, ON MLS® S12629482

Residential Freehold (Detached)

$999950.0

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

Top 5 Reasons You Will Love This Home: 1) Set on a sprawling property, this home delivers space, privacy, and tranquility, creating a setting where fa

44 Photos

41 Treetops Boulevard, Simcoe, ON , MLS #N12417984 , Image - 1

41 Treetops Boulevard Alliston, New Tecumseth, Simcoe, ON MLS® N12417984

Residential Freehold (Detached)

$1099000.0

Price drop by 6.9%

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

Across the street from the park this 2410 sq ft ( per MPAC ) spacious 3 + 1 bedroom vs 4 smaller bedroom optional floorplan comes with over 600 sq ft

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

104 Knox Road E, Simcoe, ON , MLS #S12640498 , Image - 1

104 Knox Road E Wasaga Beach, Simcoe, ON MLS® S12640498

Residential Freehold (Detached)

$920000.0

3 +1 Beds
3 Baths
1500-2000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Enjoy a generous 50'x230' lot with over 50' of waterfront, spacious backyard areas perfect for entertaining,

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968 Green Street, Simcoe, ON , MLS #N12445132 , Image - 1

968 Green Street Lefroy, Innisfil, Simcoe, ON MLS® N12445132

Residential Freehold (Detached)

$979000.0

Price drop by 17.0%

4 Beds
4 Baths
2500-3000 sq-ft

For Sale by Owner. Step up to luxury with a spacious 50' lot, twice the space of typical homes in the neighborhood, offering room to grow, play, and e

49 Photos

1 Mariposa Drive, Simcoe, ON , MLS #S12237649 , Image - 1

1 Mariposa Drive Orillia, Simcoe, ON MLS® S12237649

Residential Freehold (Detached)

$774900.0

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

Amazing Investment!! Completely renovated 5 Bedroom LEGAL DUPLEX in Orillia close to all amenities, walking trails and easy access from Hwy 11!! Thi

34 Photos

16 Mundy Avenue, Simcoe, ON , MLS #S12518184 , Image - 1

16 Mundy Avenue Rural Tiny, Tiny, Simcoe, ON MLS® S12518184

Residential Freehold (Detached)

$739900.0

3 Beds
2 Baths
1100-1500 sq-ft

You will love this warm and inviting turn key bungalow with approximately 2000sq ft of living space, situated close to Farlain Lake, an idyllic inland

22 Photos

6509 13th Line N/A, Simcoe, ON , MLS #N12275858 , Image - 1

6509 13th Line N/A Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N12275858

Residential Freehold (Detached)

$1695000.0

9 Beds
7 Baths
1500-2000 sq-ft

Welcome to your Private Countryside Estate overlooking Alliston !Scenic Ranch style home on 10 acres with river frontage & bonus beach area including

30 Photos

591 Oak Street, Simcoe, ON , MLS #S12528110 , Image - 1

591 Oak Street Collingwood, Simcoe, ON MLS® S12528110

Residential Freehold (Detached)

$599999.0

2 Beds
2 Baths
700-1100 sq-ft

Welcome Home to one of the nicest neighbourhoods in Collingwood! This lovely bungalow is located in the beautiful Tree Streets community. This 2 bedro

30 Photos

3410 Reservoir Road, Simcoe, ON , MLS #S12383376 , Image - 1

3410 Reservoir Road Rural Severn, Severn, Simcoe, ON MLS® S12383376

Residential Freehold (Detached)

$899000.0

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

Top 5 Reasons You Will Love This Home: 1) Enjoy the perfect blend of convenience and country charm in this ideally located property, just minutes from

31 Photos

5716 County Road 56 N/A, Simcoe, ON , MLS #N12538626 , Image - 1

5716 County Road 56 N/A Rural Essa, Essa, Simcoe, ON MLS® N12538626

Residential Freehold (Detached)

$999000.0

3 Beds
2 Baths
2000-2500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Venture into a piece of history with this timeless century home, originally built in 1883, featuring beautif

26 Photos

648 10th Line, Simcoe, ON , MLS #N12513678 , Image - 1

648 10th Line Rural Innisfil, Innisfil, Simcoe, ON MLS® N12513678

Residential Freehold (Detached)

$729000.0

4 Beds
2 Baths
1500-2000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Just steps to the sandy shores of Lake Simcoe and Leonard Beach, this beautifully updated home provides a ch

24 Photos

122 Mitchells Beach Road, Simcoe, ON , MLS #S12449403 , Image - 1

122 Mitchells Beach Road Victoria Harbour, Tay, Simcoe, ON MLS® S12449403

Residential Freehold (Detached)

$1088888.0

1 +1 Beds
4 Baths
700-1100 sq-ft

Top 5 Reasons You Will Love This Home: 1) Stunning panoramic views of peaceful Hogg Bay await a fishing enthusiast and those seeking direct access to

25 Photos

81 Corner Brook Trail, Simcoe, ON , MLS #N12585902 , Image - 1

81 Corner Brook Trail Alcona, Innisfil, Simcoe, ON MLS® N12585902

Residential Freehold (Detached)

$440000.0

2 Beds
2 Baths
1100-1500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Located in an Adult Lifestyle community of Sandycove Acres this home offers thoughtfully selected upgrades t

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39 Vanderpost Crescent, Simcoe, ON , MLS #N12469883 , Image - 1

39 Vanderpost Crescent Thornton, Essa, Simcoe, ON MLS® N12469883

Residential Freehold (Detached)

$1749900.0

4 +2 Beds
3 Baths
2000-2500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Beautifully crafted custom home offering an impressive 4,746 square feet of living space, nestled in the cha

31 Photos

6 Alana Drive, Simcoe, ON , MLS #S12630890 , Image - 1

6 Alana Drive Centre Vespra, Springwater, Simcoe, ON MLS® S12630890

Residential Freehold (Detached)

$1499000.0

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

Top 5 Reasons You Will Love This Home: 1) If you're dreaming of a spacious lot surrounded by mature trees but still want to be less than 10 minutes fr

32 Photos

7 Meadowlark Way, Simcoe, ON , MLS #S12639170 , Image - 1

7 Meadowlark Way Collingwood, Simcoe, ON MLS® S12639170

Residential Freehold (Detached)

$3590000.0

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! Located in the equally coveted and conveni

25 Photos

1941 Vespra Valley Road, Simcoe, ON , MLS #S12472491 , Image - 1

1941 Vespra Valley Road Rural Springwater, Springwater, Simcoe, ON MLS® S12472491

Residential Freehold (Detached)

$889900.0

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

Top 5 Reasons You Will Love This Home: 1) This ranch bungalow showcases attractive curb appeal and sits on over half an acre, combining peaceful rural

24 Photos

83 King Road, Simcoe, ON , MLS #S12572592 , Image - 1

83 King Road Waubaushene, Tay, Simcoe, ON MLS® S12572592

Residential Freehold (Detached)

$824900.0

3 Beds
3 Baths
2000-2500 sq-ft

Top 5 Reasons You Will Love This Home: 1) This incredibly versatile turn-key property offers endless possibilities with a spacious two-storey layout p

21 Photos

2645 ST AMANT Road, Simcoe, ON , MLS #S12638792 , Image - 1

2645 ST AMANT Road Rural Severn, Severn, Simcoe, ON MLS® S12638792

Residential Freehold (Detached)

$990000.0

3 +0 Beds
1 Baths
1100-1500 sq-ft

Escape to the tranquility of this 3-bedroom home nestled on a sprawling 110-acre property. This is a rare opportunity to own your own piece of paradis

50 Photos

13 Couples Court, Simcoe, ON , MLS #S12377790 , Image - 1

13 Couples Court East Bayfield, Barrie, Simcoe, ON MLS® S12377790

Residential Freehold (Detached)

$878800.0

Price drop by 2.3%

3 +1 Beds
3 Baths
1500-2000 sq-ft

Welcome to this inviting 4-bedroom bungalow tucked on a quiet, private cul-de-sac in Barrie's convenient north end. Thoughtfully updated for comfort a

40 Photos

130 Concession 15 N/A W, Simcoe, ON , MLS #S12424833 , Image - 1

130 Concession 15 N/A W Rural Tiny, Tiny, Simcoe, ON MLS® S12424833

Residential Freehold (Detached)

$2599000.0

4 Beds
3 Baths
3500-5000 sq-ft

Your Dream Country Retreat! Experience the perfect blend of luxury, functionality, and self-sufficiency on this breathtaking 40-acre estate. Thoughtfu

50 Photos

326 BLUEBERRY MARSH Road, Simcoe, ON , MLS #S12437711 , Image - 1

326 BLUEBERRY MARSH Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S12437711

Residential Freehold (Detached)

$1699900.0

3 +0 Beds
3 Baths
3000-3500 sq-ft

Stunning estate property situated on 28 acres in central Oro-Medonte location with a custom built home by Gilkon Construction, who are builders of hig

46 Photos

29 Quinn Avenue, Simcoe, ON , MLS #S12571198 , Image - 1

29 Quinn Avenue Orillia, Simcoe, ON MLS® S12571198

Residential Freehold (Detached)

$549900.0

2 +1 Beds
2 Baths
700-1100 sq-ft

Welcome to this well-maintained two-bedroom bungalow located in a mature West Orillia neighbourhood. Situated on a fully fenced 70' x 189' lot, this p

38 Photos

971 Mosley Street, Simcoe, ON , MLS #S12417068 , Image - 1

971 Mosley Street Wasaga Beach, Simcoe, ON MLS® S12417068

Residential Freehold (Detached)

$799000.0

Price drop by 5.9%

5 Beds
2 Baths
700-1100 sq-ft

Welcome to your own private retreat on the river! This 5-bedroom, 2-bathroom home in beautiful Wasaga Beach offers year round living. Walk in to this

24 Photos

86 Sixth Street, Simcoe, ON , MLS #S12638064 , Image - 1

86 Sixth Street Midland, Simcoe, ON MLS® S12638064

Residential Freehold (Detached)

$375000.0

3 Beds
1 Baths
1500-2000 sq-ft

CHARACTER-FILLED HOME WITH GEORGIAN BAY VIEWS, A 200 FT DEEP LOT, & READY TO BECOME YOUR PINTEREST DREAM HOME! Start your day on the enclosed front po

39 Photos

14 Wilson Street, Simcoe, ON , MLS #N12636832 , Image - 1

14 Wilson Street Tottenham, New Tecumseth, Simcoe, ON MLS® N12636832

Residential Freehold (Detached)

$849900.0

3 Beds
2 Baths
2000-2500 sq-ft

Welcome to this beautifully restored Century home, ideally located on one of the area's most sought-after streets, where timeless character meets mode

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169 Second Street, Simcoe, ON , MLS #S12226359 , Image - 1

169 Second Street Collingwood, Simcoe, ON MLS® S12226359

Residential Freehold (Detached)

$1950000.0

4 Beds
4 Baths
2000-2500 sq-ft

Welcome to Charming Collingwood Living. Where Luxury Meets Location! Discover the perfect blend of elegance, comfort, and convenience in this stunning

40 Photos

1372 Division Road E, Simcoe, ON , MLS #S12517032 , Image - 1

1372 Division Road E Rural Severn, Severn, Simcoe, ON MLS® S12517032

Residential Freehold (Detached)

$2199000.0

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

INDULGE IN LUXURY ON 2.1 ACRES WITH BREATHTAKING VIEWS, SHARED OWNERSHIP OF AN ADDITIONAL 32 ACRES, & A MAN-MADE LAKE!! Enter a realm of unrivalled el

Shortlisted Properties

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