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Detached Houses for Sale in Simcoe Under $5M

Showing results 1 - 30 of 548

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: February 05, 2026

1 Photos

7 Wakefield Boulevard Angus, Essa, Simcoe, ON MLS® N12760280

Residential Freehold (Detached)

$888000.0

4 Beds
3 Baths
2000-2500 sq-ft

Welcome to 7 Wakefield Blvd in Angus, a well-maintained, thoughtfully designed detached home that offers comfort, space, and functionality for growing

43 Photos

28 Casserley Crescent, Simcoe, ON , MLS #N12760226 , Image - 1

28 Casserley Crescent Tottenham, New Tecumseth, Simcoe, ON MLS® N12760226

Residential Freehold (Detached)

$799000.0

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

Welcome to this stunning, modern detached home in the heart of Tottenham, Ontario! This chic, move-in-ready residence offers contemporary living at it

30 Photos

139 Trout Lane, Simcoe, ON , MLS #S12743234 , Image - 1

139 Trout Lane Rural Tiny, Tiny, Simcoe, ON MLS® S12743234

Residential Freehold (Detached)

$659000.0

4 +0 Beds
3 Baths
1500-2000 sq-ft

THE BEST DESTINATION TO LIVE YOUR DREAMS! ESCAPE TO YOUR OWN PARADISE! Minutes to the water's edge of Sand Castle Beach and breathtaking sunsets overl

13 Photos

1277 Sunnidale Road, Simcoe, ON , MLS #S12759654 , Image - 1

1277 Sunnidale Road Rural Springwater, Springwater, Simcoe, ON MLS® S12759654

Residential Freehold (Detached)

$1450000.0

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

Welcome to this one-of-a-kind custom-built side split home, perfectly situated on a spacious 120x193ft lot. Designed with versatility in mind, this pr

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

45 Photos

31 Lakeview Crescent, Simcoe, ON , MLS #S12665680 , Image - 1

31 Lakeview Crescent Rural Tiny, Tiny, Simcoe, ON MLS® S12665680

Residential Freehold (Detached)

$650000.0

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

Luxury real estate is far more than a transaction - it's about elevating your lifestyle. Nestled in a sought-after 4-season location with serene views

32 Photos

10 Sinclair Crescent, Simcoe, ON , MLS #S12757040 , Image - 1

10 Sinclair Crescent Atherley, Ramara, Simcoe, ON MLS® S12757040

Residential Freehold (Detached)

$626000.0

3 Beds
2 Baths
1500-2000 sq-ft

Experience Refined Adult Living At Lakepoint Village. Discover The Perfect Harmony Of Rural Serenity And Urban Convenience In This Premier Adult Lifes

43 Photos

9 Byers Street, Simcoe, ON , MLS #S12759346 , Image - 1

9 Byers Street Snow Valley, Springwater, Simcoe, ON MLS® S12759346

Residential Freehold (Detached)

$1759900.0

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

Top 5 Reasons You Will Love This Home: 1) Perfectly placed in one of Springwater's most prestigious and sought-after neighbourhoods, this stunning hom

41 Photos

3678 Kimberley Street, Simcoe, ON , MLS #N12759330 , Image - 1

3678 Kimberley Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N12759330

Residential Freehold (Detached)

$1199900.0

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

STUNNING 3,700+ SQ FT FAMILY RETREAT STEPS TO LAKE SIMCOE & FRIDAY HARBOUR, SHOWCASING MODERN UPGRADES, SUNLIT OPEN-CONCEPT LIVING, & A RESORT-INSPIRE

21 Photos

92 Wesley Avenue, Simcoe, ON , MLS #S12758518 , Image - 1

92 Wesley Avenue Wasaga Beach, Simcoe, ON MLS® S12758518

Residential Freehold (Detached)

$689000.0

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

Top 5 Reasons You Will Love This Home: 1) Tastefully updated raised bungalow situated in a quiet and well-maintained neighbourhood in the heart of Was

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

26 Photos

125 Gardiner Drive N, Simcoe, ON , MLS #N12754170 , Image - 1

125 Gardiner Drive N Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12754170

Residential Freehold (Detached)

$1499000.0

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

Stunning 2-Storey Detached 5-Bedroom Home on a Premium Lot Backing Onto a Park. Beautifully upgraded from top to bottom, this residence features a go

37 Photos

11 Saint Avenue, Simcoe, ON , MLS #N12723354 , Image - 1

11 Saint Avenue Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12723354

Residential Freehold (Detached)

$1199000.0

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

Exquisite Bradford Home with Resort-Style Backyard and Legal Finished Basement* This stunning home is a true gem situated on a premium 49.21x124.67 ft

40 Photos

112 Tecumseth Pines Drive, Simcoe, ON , MLS #N12722946 , Image - 1

112 Tecumseth Pines Drive Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N12722946

Residential Freehold (Detached)

$549000.0

2 +1 Beds
3 Baths
1500-2000 sq-ft

Thinking of resizing and enjoying a more stress-free lifestyle? This Friendly Adult Lifestyle Community might just be what you are looking for! Tecums

22 Photos

6509 13th Line N/A, Simcoe, ON , MLS #N12748140 , Image - 1

6509 13th Line N/A Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N12748140

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

29 Photos

63 Bailey Crescent, Simcoe, ON , MLS #S12758428 , Image - 1

63 Bailey Crescent Wyevale, Tiny, Simcoe, ON MLS® S12758428

Residential Freehold (Detached)

$799000.0

4 Beds
2 Baths
1100-1500 sq-ft

IN-LAW OR INCOME POTENTIAL | NEW SEPTIC 2024 | FULLY FENCED YARD | DOUBLE GARAGE WITH LARGE PAVED DRIVEWAY. Move-in ready and packed with flexibility,

48 Photos

1 Spencer Street, Simcoe, ON , MLS #S12758314 , Image - 1

1 Spencer Street Collingwood, Simcoe, ON MLS® S12758314

Residential Freehold (Detached)

$1229000.0

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

Stunning Middleton Model by Devonleigh Homes. Prime Corner Lot with Blue Mountain Views.This exquisite 4-year-old Middleton model by the highly regard

50 Photos

148 MARSELLUS Drive, Simcoe, ON , MLS #S12754908 , Image - 1

148 MARSELLUS Drive Holly, Barrie, Simcoe, ON MLS® S12754908

Residential Freehold (Detached)

$789900.0

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

Designed with a fully self-contained in-law suite, this raised bungalow is set on a premium lot in Barrie's highly desirable Holly community, offering

Open House : Sun Feb 08, 12:00 PM to 02:00 PM

49 Photos

120 Jewel House Lane, Simcoe, ON , MLS #S12757400 , Image - 1

120 Jewel House Lane Innis-Shore, Barrie, Simcoe, ON MLS® S12757400

Residential Freehold (Detached)

$1070000.0

4 Beds
3 Baths
2500-3000 sq-ft

Situated on a low-traffic street in one of Barrie's most established family neighbourhoods, this warm and welcoming home offers a thoughtful layout, a

43 Photos

54 Cityview Circle, Simcoe, ON , MLS #S12757392 , Image - 1

54 Cityview Circle Holly, Barrie, Simcoe, ON MLS® S12757392

Residential Freehold (Detached)

$999999.0

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

Welcome To 54 Cityview Circle In Barrie, A Home Nestled In One of Ardagh's Sought After Neighbourhoods! The Home Greets You Offering Extensive landsca

49 Photos

27 Heyden Avenue, Simcoe, ON , MLS #S12223834 , Image - 1

27 Heyden Avenue Orillia, Simcoe, ON MLS® S12223834

Residential Freehold (Detached)

$1875000.0

Price drop by 14.8%

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

27 Heyden Avenue, a magnificent 2460 sq ft Viceroy-style bungalow perfectly situated on a generous 77-foot stretch of Lake Simcoe waterfront in a prim

40 Photos

130 Melissa Lane, Simcoe, ON , MLS #S12747348 , Image - 1

130 Melissa Lane Rural Tiny, Tiny, Simcoe, ON MLS® S12747348

Residential Freehold (Detached)

$3390000.0

3 +2 Beds
4 Baths
3000-3500 sq-ft

Nestled within the exclusive Cedar Ridge community in Tiny Township, this architect-designed retreat offers a rare opportunity to own a custom waterfr

38 Photos

93 Edward Street, Simcoe, ON , MLS #S12756554 , Image - 1

93 Edward Street Penetanguishene, Simcoe, ON MLS® S12756554

Residential Freehold (Detached)

$729777.0

0 +4 Beds
3 Baths
700-1100 sq-ft

Custom All-Brick Beauty in a Prime Penetang Location! This impressive 2,000+ sq ft finished home offers 3+ bedrooms and 3 bathrooms, ideal for a growi

30 Photos

467 Irwin Street, Simcoe, ON , MLS #S12675618 , Image - 1

467 Irwin Street Midland, Simcoe, ON MLS® S12675618

Residential Freehold (Detached)

$579900.0

3 Beds
2 Baths
700-1100 sq-ft

Welcome to this beautifully updated family home located on a quiet, tree-lined street in a sought-after neighborhood. This inviting residence offers t

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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)

$879000.0

Price drop by 25.4%

4 Beds
4 Baths
2500-3000 sq-ft

For Sale by Owner. Click on More Information Link Below. Step up to luxury with a spacious 50' lot, twice the space of typical homes in the neighborho

30 Photos

14 Gold Park Gate, Simcoe, ON , MLS #N12591070 , Image - 1

14 Gold Park Gate Angus, Essa, Simcoe, ON MLS® N12591070

Residential Freehold (Detached)

$799888.0

Price drop by 1.2%

4 Beds
3 Baths
2000-2500 sq-ft

Welcome to 14 Gold Park Gate in the sought after 5th Line subdivision of Angus. Conveniently located, it is only minutes from local amenities and CFB

11 Photos

52 Elmbrook Drive, Simcoe, ON , MLS #S12755788 , Image - 1

52 Elmbrook Drive 400 West, Barrie, Simcoe, ON MLS® S12755788

Residential Freehold (Detached)

$834900.0

4 Beds
3 Baths
1500-2000 sq-ft

Fantastic two storey home in a terrific family neighbourhood in the newer part of Holly in Barrie's south end. The ensuite has been recently renovated

21 Photos

28 Union Boulevard, Simcoe, ON , MLS #S12755712 , Image - 1

28 Union Boulevard Wasaga Beach, Simcoe, ON MLS® S12755712

Residential Freehold (Detached)

$799900.0

4 Beds
3 Baths
1500-2000 sq-ft

Welcome to 28 Union Blvd. A stunning 4-bedroom, 2.5-bathroom home is located in the desirable Sunnidale community by Redberry Homes, a master-planned

37 Photos

16 Basswood Drive, Simcoe, ON , MLS #S12755474 , Image - 1

16 Basswood Drive Wasaga Beach, Simcoe, ON MLS® S12755474

Residential Freehold (Detached)

$1199990.0

4 Beds
3 Baths
2500-3000 sq-ft

Step into this impressive raised bungalow in Wasaga Beach's prestigious Wasaga Sands Estates, set on a rare ravine lot surrounded by expansive estate

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130 Concession 15 N/A W, Simcoe, ON , MLS #S12754704 , Image - 1

130 Concession 15 N/A W Rural Tiny, Tiny, Simcoe, ON MLS® S12754704

Residential Freehold (Detached)

$2599000.0

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

23 Photos

2132 14th Line, Simcoe, ON , MLS #N12755054 , Image - 1

2132 14th Line Gilford, Innisfil, Simcoe, ON MLS® N12755054

Residential Freehold (Detached)

$1195000.0

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

The Perfect All Brick 4 Bedroom Bungalow * Premium Lot W/ 150 Ft Frontage * 0.7 Acre Featuring 2,245 Sq Ft On Main Level * Ultimate Privacy Surrounded

Shortlisted Properties

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