2274+ Houses for Sale in Simcoe Under $5 Million

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204 Dyer Drive, Simcoe, ON , MLS #S12456188 , Image - 1

204 Dyer Drive Wasaga Beach, Simcoe, ON MLS® S12456188

Residential Freehold (Detached)

$634900.0

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

This beautifully maintained raised bungalow offers charm, functionality, and plenty of space for the whole family. The main level features a bright ea

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8429 Poplar Side Road, Simcoe, ON , MLS #S12537646 , Image - 1

8429 Poplar Side Road Rural Clearview, Clearview, Simcoe, ON MLS® S12537646

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

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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

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2705 14th Line, Simcoe, ON , MLS #N12495028 , Image - 1

2705 14th Line Gilford, Innisfil, Simcoe, ON MLS® N12495028

Residential Freehold (Detached)

$2430000.0

Price drop by 4.1%

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

Welcome to this exceptional 3+2 bedroom, 5 bathroom custom-built estate home set on a private 3.25-acre treed property, offering luxury country living

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48 Madawaska Trail, Simcoe, ON , MLS #S12538492 , Image - 1

48 Madawaska Trail Wasaga Beach, Simcoe, ON MLS® S12538492

Residential Freehold (Detached)

$419000.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to your new home in Wasaga! This land lease home is the perfect option for 4-season living without the high purchase price. We're located in t

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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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126 Bell Farm Road, Simcoe, ON , MLS #S12538046 , Image - 1

Unit-113, 126 Bell Farm Road Alliance, Barrie, Simcoe, ON MLS® S12538046

Residential Condo & Other (Condo Apartment)

$379000.0

2 Beds
2 Baths
900-999 sq-ft

Bright and accessible garden-level condo ideal location! - Very accessible 2-bedroom, 2-bath end-unit condo located just steps from the buildings side

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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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147 Julia Crescent, Simcoe, ON , MLS #S12537062 , Image - 1

147 Julia Crescent Orillia, Simcoe, ON MLS® S12537062

Residential Freehold (Link)

$599999.0

3 Beds
3 Baths
1100-1500 sq-ft

Welcome to this charming 2-storey home located in the sought-after Westridge neighbourhood, just minutes from big box stores, restaurants, and all maj

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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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241 Sea Ray Avenue, Simcoe, ON , MLS #N12537114 , Image - 1

Unit-A101, 241 Sea Ray Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N12537114

Residential Condo & Other (Condo Apartment)

$538888.0

2 Beds
2 Baths
800-899 sq-ft

This is your chance to own a slice of luxury vacation living, just one hour from the GTA. Whether you're looking for a full-time home, weekend escape,

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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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553 Tenth Street, Simcoe, ON , MLS #S12501448 , Image - 1

553 Tenth Street Collingwood, Simcoe, ON MLS® S12501448

Residential Condo & Other (Condo Townhouse)

$372500.0

Price drop by 1.3%

3 +1 Beds
3 Baths
1200-1399 sq-ft

Attention first time home buyers!! This 4-bedroom (3+1) townhouse condo is priced to sell. With a few little cosmetic upgrades, you could transform th

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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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67 Wozniak Road, Simcoe, ON , MLS #S12533804 , Image - 1

67 Wozniak Road Penetanguishene, Simcoe, ON MLS® S12533804

Residential Freehold (Vacant Land)

$99000.0

< 700 sq-ft

OPPORTUNITY KNOCKS! 50 X 149 FT CLEARED VACANT LOT STEPS FROM GEORGIAN BAY! Discover the perfect canvas for your dream home on this spacious parcel of

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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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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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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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39 Mary Street, Simcoe, ON , MLS #S12438962 , Image - 1

Unit-2104, 39 Mary Street City Centre, Barrie, Simcoe, ON MLS® S12438962

Residential Condo & Other (Condo Apartment)

$545000.0

Price drop by 2.5%

1 +1 Beds
2 Baths
500-599 sq-ft

Luxurious 1-Bedroom + Den With 585 Sqft Interior in Debut Waterfront Residences! This premium unit offers a spacious open concept layout with modern d

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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

Houses for Sale in Simcoe Under $5 Million - P21

Rosehaven Simcoe Woods