855+ Detached Houses for Sale in Simcoe Under $5M

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54 Hearthstone Drive, Simcoe, ON , MLS #S12538364 , Image - 1

54 Hearthstone Drive Rural Tay, Tay, Simcoe, ON MLS® S12538364

Residential Freehold (Detached)

$549000.0

3 Beds
2 Baths
2000-2500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Recreation and entertainers dream being on the Sturgeon River, offering excellent fishing and easy access to

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1398 Old Second Road N, Simcoe, ON , MLS #S12490196 , Image - 1

1398 Old Second Road N Phelpston, Springwater, Simcoe, ON MLS® S12490196

Residential Freehold (Detached)

$2699900.0

3 +0 Beds
2 Baths
2000-2500 sq-ft

Welcome to your private country retreat nestled on 78 sprawling acres in the heart of Springwater, this extraordinary property offers the perfect blen

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1238 Benson Street, Simcoe, ON , MLS #N12421827 , Image - 1

1238 Benson Street Alcona, Innisfil, Simcoe, ON MLS® N12421827

Residential Freehold (Detached)

$659900.0

Price drop by 2.9%

3 Beds
2 Baths
1100-1500 sq-ft

Welcome to this wonderful 3 bedroom, 2 bathroom home located in a family-friendly neighbourhood, just a short walk to a local elementary school. This

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84 Atlantis Drive W, Simcoe, ON , MLS #S12456892 , Image - 1

84 Atlantis Drive W Orillia, Simcoe, ON MLS® S12456892

Residential Freehold (Detached)

$789900.0

4 Beds
3 Baths
2000-2500 sq-ft

**NO CARPET IN HOUSE** New Flooring Installed in July 2025. Welcome To 84 Atlantis Dr. A Home That Truly Checks All The Right Boxes. This Elegant, Mod

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4927 25 Side Road, Simcoe, ON , MLS #N12537812 , Image - 1

4927 25 Side Road Rural Essa, Essa, Simcoe, ON MLS® N12537812

Residential Freehold (Detached)

$1149900.0

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

Custom-Built Walk-Out Bungalow on 2.3 Acres of Ultimate Privacy! Experience serene country living in this beautifully crafted custom walk-out bungalow

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5 Park Lane, Simcoe, ON , MLS #S12532412 , Image - 1

5 Park Lane Brechin, Ramara, Simcoe, ON MLS® S12532412

Residential Freehold (Detached)

$1700000.0

3 Beds
2 Baths
2000-2500 sq-ft

Welcome to the wonderful community of Bayshore Village! This 3 bedroom bungalow is set on a south facing lot with direct frontage on beautiful Lake Si

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54 Chamberlain Crescent, Simcoe, ON , MLS #S12529420 , Image - 1

54 Chamberlain Crescent Collingwood, Simcoe, ON MLS® S12529420

Residential Freehold (Detached)

$889000.0

3 Beds
3 Baths
2000-2500 sq-ft

Welcome to this charming 3-bedroom, 3-bath brick home perfectly situated on a spacious corner lot in the desirable community of Creek Side in Collingw

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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 100-acre farm in South Adjala, surrounded by estate properties and just minutes from Caledon. Features gently rolling farmland with approx

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17 Sugarbush Road, Simcoe, ON , MLS #S12329321 , Image - 1

17 Sugarbush Road Sugarbush, Oro-Medonte, Simcoe, ON MLS® S12329321

Residential Freehold (Detached)

$799900.0

Price drop by 5.9%

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

Welcome to 17 Sugarbush Road, Oro-Medonte - where community, comfort & outdoor living come together. Whether you're seeking an escape from city life,

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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

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6222 Bluebird Street, Simcoe, ON , MLS #S12534978 , Image - 1

6222 Bluebird Street Rural Ramara, Ramara, Simcoe, ON MLS® S12534978

Residential Freehold (Detached)

$579999.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to your affordable lakefront escape on the peaceful shores of Lake St. John! This cozy 2-bedroom, 1-bathroom four-season home is the perfect e

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3588 13 Line N, Simcoe, ON , MLS #S12534786 , Image - 1

3588 13 Line N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S12534786

Residential Freehold (Detached)

$1999999.0

6 Beds
4 Baths
5000 + sq-ft

MUST BE SEEN: Exquisite 5500+ square foot custom-built luxury modern farmhouse home with panoramic country views. This home is filled with thoughtful

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117 Professor Day Drive, Simcoe, ON , MLS #N12533602 , Image - 1

117 Professor Day Drive Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12533602

Residential Freehold (Detached)

$1018000.0

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

Step Into This Beautiful 4 + 1 Bedroom Home Located In The Heart Of Bradford. Open-Concept Layout Featuring A Family Room & A Dining Area, Kitchen Wit

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160 letitia Street, Simcoe, ON , MLS #S12533568 , Image - 1

160 letitia Street Letitia Heights, Barrie, Simcoe, ON MLS® S12533568

Residential Freehold (Detached)

$738000.0

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

Welcome to 160 Letitia Street, nestled in the prestigious Letitia Heights community of Barrie a home that redefines modern living. This brand new full

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13 Del Ray Crescent Wasaga Beach, Simcoe, ON MLS® S12277664

Residential Freehold (Detached)

$999900.0

5 Beds
4 Baths
3000-3500 sq-ft

Never lived in, Large 3157 sqft house, One of the biggest house in the area. Close to Wasaga beach. Premium lot, Paid $130K in Upgrades to builder. op

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5 Bailey Crescent, Simcoe, ON , MLS #S12533484 , Image - 1

5 Bailey Crescent Wyevale, Tiny, Simcoe, ON MLS® S12533484

Residential Freehold (Detached)

$1015000.0

3 Beds
3 Baths
2000-2500 sq-ft

Gorgeous 2,246 square foot home on a mature private lot with heated inground swimming pool in the fully fenced backyard. Very inviting living/dining c

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2266 FOXMEAD Road, Simcoe, ON , MLS #S12427020 , Image - 1

2266 FOXMEAD Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S12427020

Residential Freehold (Detached)

$975000.0

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

Farm-Shop-Home-Country Retreat- The perfect blend of county living for all in the Family. 2266 Foxmead Road, This Property Boasts, New Roof Completed

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93 Bayshore Drive, Simcoe, ON , MLS #S12087968 , Image - 1

93 Bayshore Drive Rural Ramara, Ramara, Simcoe, ON MLS® S12087968

Residential Freehold (Detached)

$948000.0

Price drop by 11.8%

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

Welcome home to this wonderful 4-bedroom, 3-bath home in the prestigious Bayshore Village waterfront community. Backing onto a tranquil pond, this pro

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9 Monica Road, Simcoe, ON , MLS #S12532648 , Image - 1

9 Monica Road Rural Tiny, Tiny, Simcoe, ON MLS® S12532648

Residential Freehold (Detached)

$3999000.0

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

A rare opportunity to own over 300 feet of private Georgian Bay waterfront in one of Tinys most coveted enclaves. Set on 2+ acres with unobstructed vi

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635 Wayne Crescent, Simcoe, ON , MLS #S12246987 , Image - 1

635 Wayne Crescent Midland, Simcoe, ON MLS® S12246987

Residential Freehold (Detached)

$699000.0

Price drop by 2.8%

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

Welcome Home to 635 Wayne Cres Midland Ontario, This wonderful all brick raised bungalow is Available Now for you and your family. This Home offers 2

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3 Earldom Boulevard, Simcoe, ON , MLS #S12337867 , Image - 1

3 Earldom Boulevard Port McNicoll, Tay, Simcoe, ON MLS® S12337867

Residential Freehold (Detached)

$699999.0

3 Beds
2 Baths
1500-2000 sq-ft

Welcome to 3 Earldom Boulevard located in the quiet community of Port McNicoll, walking distance to the lake! This tastefully appointed 3-bedroom, 2-b

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15 Recreation Drive, Simcoe, ON , MLS #N12532122 , Image - 1

15 Recreation Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N12532122

Residential Freehold (Detached)

$559000.0

2 Beds
2 Baths
1100-1500 sq-ft

Get the golf cart ready! Are you looking for an active lifestyle? Ready to downsize? Come check out Sandycove Acres! A fabulous community located just

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97 Tracey Lane, Simcoe, ON , MLS #S12531664 , Image - 1

97 Tracey Lane Collingwood, Simcoe, ON MLS® S12531664

Residential Freehold (Detached)

$819000.0

3 Beds
3 Baths
1500-2000 sq-ft

This Marigold model has everything you need and more! With 3 bedrooms and 2 full bathrooms, it's perfect for families, couples, or anyone looking to

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4 Trillium Crescent, Simcoe, ON , MLS #S12521140 , Image - 1

4 Trillium Crescent Allandale Heights, Barrie, Simcoe, ON MLS® S12521140

Residential Freehold (Detached)

$855000.0

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

Beautifully maintained 2-storey all-brick home nestled in Barrie's sought-after Allandale Heights community. This spacious residence offers the perfec

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96 Redmond Crescent, Simcoe, ON , MLS #S12487962 , Image - 1

96 Redmond Crescent Centre Vespra, Springwater, Simcoe, ON MLS® S12487962

Residential Freehold (Detached)

$999000.0

Price drop by 9.2%

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

Experience Refined Living in This Exquisite Primrose Model, Thoughtfully Upgraded with Designer Touches Throughout! Nestled on a premium 150-foot deep

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4 Bronze Bird Crescent, Simcoe, ON , MLS #S12471839 , Image - 1

4 Bronze Bird Crescent New Lowell, Clearview, Simcoe, ON MLS® S12471839

Residential Freehold (Detached)

$1299000.0

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

Your Search Just Ended! This stunning custom-built bungalow combines the serenity of nature with modern architecture and technology. Nestled on a 1.47

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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

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38 Camelot Square, Simcoe, ON , MLS #S12529442 , Image - 1

38 Camelot Square Innis-Shore, Barrie, Simcoe, ON MLS® S12529442

Residential Freehold (Detached)

$1499900.0

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

Welcome to refined living in one of South Barrie's most sought-after neighbourhoods, just steps from Wilkins Beach. Set on a private, tree-lined corne

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4304 Plum Point Road, Simcoe, ON , MLS #S12521150 , Image - 1

4304 Plum Point Road Rural Ramara, Ramara, Simcoe, ON MLS® S12521150

Residential Freehold (Detached)

$840000.0

3 Beds
1 Baths
700-1100 sq-ft

Enjoy year-round living in this fully winterized waterfront home, nestled on a private lot in a sheltered bay with 93 feet of shoreline. Featuring stu

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527 Big Bay Point Road, Simcoe, ON , MLS #N12528598 , Image - 1

527 Big Bay Point Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N12528598

Residential Freehold (Detached)

$1480000.0

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

Set within Innisfil's prestigious Big Bay Point community-just 90 minutes from Toronto-this nearly ten-acre private retreat offers an extraordinary bl

Detached Houses for Sale in Simcoe Under $5M - P13

Rosehaven Simcoe Woods