251+ Detached Houses for Sale in Simcoe Under $500K

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8 Belle Isle Arm N/A, Simcoe, ON , MLS #N13164136 , Image - 1

8 Belle Isle Arm N/A Rural Innisfil, Innisfil, Simcoe, ON MLS® N13164136

Residential Freehold (Detached)

$299900.0

Price drop by 11.8%

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to this lovingly maintained and updated 2 bedroom home located in the desirable adult community of Sandy Cove acres. The new buyers may have t

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10 Simcoe Road, Simcoe, ON , MLS #S13547460 , Image - 1

10 Simcoe Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13547460

Residential Freehold (Detached)

$499000.0

Price drop by 5.7%

2 +0 Beds
1 Baths
< 700 sq-ft

Nestled on a quiet cul-de-sac in a peaceful waterfront community, this cozy 1-bedroom cottage offers the perfect summer escape. Whether you're looking

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137 Dufferin Street, Simcoe, ON , MLS #S13654852 , Image - 1

137 Dufferin Street Orillia, Simcoe, ON MLS® S13654852

Residential Freehold (Detached)

$274900.0

Price drop by 3.5%

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

WOW! Check out this updated price! OPEN HOUSE Saturday, August 29th 1-3pm. Seller is motivated! Seller says, bring any reasonable Offer. Ideal

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365 Robins Point Road, Simcoe, ON , MLS #S13719356 , Image - 1

365 Robins Point Road Victoria Harbour, Tay, Simcoe, ON MLS® S13719356

Residential Freehold (Detached)

$469900.0

3 Beds
1 Baths
700-1100 sq-ft

Top 5 Reasons You Will Love This Property: Unlock the incredible potential of this expansive 146'x170' lot in the heart of Victoria Harbour. This uniq

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47 68th Street, Simcoe, ON , MLS #S13698266 , Image - 1

47 68th Street Wasaga Beach, Simcoe, ON MLS® S13698266

Residential Freehold (Detached)

$499000.0

1 Beds
1 Baths
700-1100 sq-ft

Bright, airy and surrounded by nature, this beautifully updated home sits on a private, treed lot just steps from the beach-perfect for morning walks,

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22 Balsam Street, Simcoe, ON , MLS #S13715652 , Image - 1

22 Balsam Street Rural Tiny, Tiny, Simcoe, ON MLS® S13715652

Residential Freehold (Detached)

$466000.0

3 Beds
1 Baths
700-1100 sq-ft

Tucked away on a quiet street steps from Georgian Bay, 22 Balsam Street is a rare gem for cottage seekers, first-time buyers or retirees seeking acces

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19 White Pines Trail, Simcoe, ON , MLS #S13629300 , Image - 1

19 White Pines Trail Wasaga Beach, Simcoe, ON MLS® S13629300

Residential Freehold (Detached)

$149900.0

Price drop by 9.1%

2 Beds
1 Baths
700-1100 sq-ft

MOTIVATED SELLERS HAVE INCLUDED PARK FEES FOR 2026 - Move in and enjoy! Welcome to your perfect seasonal getaway in the highly sought-after Countrylif

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10 Brookside Drive, Simcoe, ON , MLS #S13596848 , Image - 1

10 Brookside Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13596848

Residential Freehold (Detached)

$449990.0

Price drop by 10.0%

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

Welcome to 10 Brookside Drive, where the best of Georgian Bay's beach lifestyle is right at your doorstep. A two-minute walk to the stunning sandy sho

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246 Mary Street, Simcoe, ON , MLS #S13652024 , Image - 1

246 Mary Street Orillia, Simcoe, ON MLS® S13652024

Residential Freehold (Detached)

$499900.0

5 Beds
2 Baths
2000-2500 sq-ft

VERSATILE 2-STOREY HOME WITH TWO SELF-CONTAINED LIVING SPACES ON AN EXTRA-DEEP LOT IN THE HEART OF ORILLIA! Rarely offered and full of opportunity, th

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8 Conc 5 Road W, Simcoe, ON , MLS #S13615484 , Image - 1

8 Conc 5 Road W Wyevale, Tiny, Simcoe, ON MLS® S13615484

Residential Freehold (Detached)

$378000.0

Price drop by 9.8%

3 Beds
1 Baths
700-1100 sq-ft

Welcome home to 8 Concession Road 5 West, perfectly situated right in the heart of the welcoming community of Wyevale! This 3-bedroom residence offers

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1085 River Road E, Simcoe, ON , MLS #S13711820 , Image - 1

1085 River Road E Wasaga Beach, Simcoe, ON MLS® S13711820

Residential Freehold (Detached)

$479900.0

3 Beds
1 Baths
700-1100 sq-ft

Welcome to 1085 River Road E, Wasaga Beach! Discover the opportunity to own a home in one of Ontario's most popular four-season destinations. Ideally

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246 Weir Street, Simcoe, ON , MLS #S13588512 , Image - 1

246 Weir Street Stayner, Clearview, Simcoe, ON MLS® S13588512

Residential Freehold (Detached)

$469000.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to this charming bungalow in the heart of Clearview! Situated on a beautiful lot and just walking distance to downtown, shops, restaurants, an

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817 Birchwood Drive, Simcoe, ON , MLS #S13536666 , Image - 1

817 Birchwood Drive Midland, Simcoe, ON MLS® S13536666

Residential Freehold (Detached)

$489000.0

Price drop by 2.0%

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

This 3+1 bedroom, 2 bath bungalow offers the perfect combination of comfort, functionality, and versatility in a desirable Midland neighbourhood. The

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5594 Upper Big Chute Road, Simcoe, ON , MLS #S13706080 , Image - 1

5594 Upper Big Chute Road Rural Severn, Severn, Simcoe, ON MLS® S13706080

Residential Freehold (Detached)

$449900.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to 5594 Upper Big Chute Rd, a move-in ready, 1,020 sq. ft. home offering seamless, one-level living with zero stairs. This peaceful 2-bed, 1-b

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681 Mkade Kegwin Miikan Road, Simcoe, ON , MLS #S13696018 , Image - 1

681 Mkade Kegwin Miikan Road Beausoleil First Nation, Christian Island 30, Simcoe, ON MLS® S13696018

Residential Freehold (Detached)

$269900.0

Price drop by 1.7%

3 Beds
1 Baths
1100-1500 sq-ft

Welcome to your own slice of paradise on the crystal-clear fresh waters of Georgian Bay. This exceptional waterfront property offers 107 feet of prist

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300 Albin Road, Simcoe, ON , MLS #S13703364 , Image - 1

300 Albin Road Rural Tay, Tay, Simcoe, ON MLS® S13703364

Residential Freehold (Detached)

$449900.0

2 Beds
1 Baths
700-1100 sq-ft

Nestled less than a minute's walk from the southern shores of Georgian Bay, this quaint bungalow offers the perfect blend of cottage charm and year-ro

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250 Kingfisher Avenue, Simcoe, ON , MLS #S13702308 , Image - 1

250 Kingfisher Avenue Port McNicoll, Tay, Simcoe, ON MLS® S13702308

Residential Freehold (Detached)

$269950.0

700-1100 sq-ft

You've just arrived in Paradise Point! This Seasonal cottage sits on a 60' x 146' lot in the heart of this beloved community. Potential !!! Project to

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3 Pineview Court, Simcoe, ON , MLS #N13246030 , Image - 1

3 Pineview Court Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13246030

Residential Freehold (Detached)

$434000.0

Price drop by 3.3%

2 Beds
2 Baths
1100-1500 sq-ft

Tecumseth Pines is a Welcoming Adult Community that caters to individuals considering a resize move and want to remain active and join a community of

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575 Simcoe Avenue, Simcoe, ON , MLS #S13701246 , Image - 1

575 Simcoe Avenue Port McNicoll, Tay, Simcoe, ON MLS® S13701246

Residential Freehold (Detached)

$499900.0

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

Check out this three bedroom bungalow backing onto greenspace in Port McNicoll. This home features gas heat w/ central air, a spacious living room din

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239 Front Street S, Simcoe, ON , MLS #S13619760 , Image - 1

239 Front Street S Orillia, Simcoe, ON MLS® S13619760

Residential Freehold (Detached)

$382000.0

Price drop by 4.3%

2 +0 Beds
1 Baths
700-1100 sq-ft

Owner relocating overseas: nice home priced for a fast sale. This 2 bedroom 1 bathroom home has undergone a complete renovation (2022). Features and U

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11 Tamarack Court, Simcoe, ON , MLS #N13700120 , Image - 1

11 Tamarack Court Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13700120

Residential Freehold (Detached)

$434900.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to Tecumseth Pines, a welcoming 55+ land-lease community known for its peaceful setting and active lifestyle. This Cypress-model bungalow sits

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110 24TH Street N, Simcoe, ON , MLS #S13600934 , Image - 1

110 24TH Street N Wasaga Beach, Simcoe, ON MLS® S13600934

Residential Freehold (Detached)

$439000.0

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

This three-bedroom home or cottage is ideally situated north of Mosley Street in highly sought-after Area 4, just a five-minute walk to the sandy shor

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706 Chestnut Street, Simcoe, ON , MLS #N13649946 , Image - 1

706 Chestnut Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N13649946

Residential Freehold (Detached)

$389000.0

2 Beds
1 Baths
< 700 sq-ft

Welcome to 706 Chestnut St in Innisfil - a charming 2-bedroom, 1-bathroom bungalow packed with opportunity and perfectly positioned just a short walk

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4174 Fountain Drive, Simcoe, ON , MLS #S13566116 , Image - 1

4174 Fountain Drive Atherley, Ramara, Simcoe, ON MLS® S13566116

Residential Freehold (Detached)

$498900.0

Price drop by 9.1%

2 Beds
1 Baths
700-1100 sq-ft

Ramara Beauty - this turn-key bungalow in sought after SIMCOE county, modern designer finishes throughout. Situated on a mature lot in a beautiful ru

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153 Lumber Road, Simcoe, ON , MLS #S13696374 , Image - 1

153 Lumber Road Victoria Harbour, Tay, Simcoe, ON MLS® S13696374

Residential Freehold (Detached)

$275000.0

1 Beds
1 Baths
700-1100 sq-ft

Ready to stop renting and start building equity? This affordable handyman special offers an exciting opportunity to step into homeownership and create

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48 Madawaska Trail, Simcoe, ON , MLS #S13689238 , Image - 1

48 Madawaska Trail Wasaga Beach, Simcoe, ON MLS® S13689238

Residential Freehold (Detached)

$395900.0

2 Beds
1 Baths
700-1100 sq-ft

Resort living at fraction of the cost! This land lease home is the perfect option for 4-season living without the high purchase price. We're located i

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2344 12 Highway, Simcoe, ON , MLS #S13532072 , Image - 1

2344 12 Highway Brechin, Ramara, Simcoe, ON MLS® S13532072

Residential Freehold (Detached)

$399999.0

2 Beds
1 Baths
700-1100 sq-ft

This is the kind of backyard you don't expect to find in town.Welcome to this well-maintained 2-bedroom, 1-bathroom bungalow in Brechin. Featuring har

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172 William Street, Simcoe, ON , MLS #S13686130 , Image - 1

172 William Street Victoria Harbour, Tay, Simcoe, ON MLS® S13686130

Residential Freehold (Detached)

$489900.0

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

Welcome to this beautifully maintained and thoughtfully updated home in the heart of Victoria Harbour! Offering year-round living in a desirable water

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179 Seventh Street, Simcoe, ON , MLS #S13671900 , Image - 1

179 Seventh Street Midland, Simcoe, ON MLS® S13671900

Residential Freehold (Detached)

$389900.0

3 Beds
1 Baths
700-1100 sq-ft

Enjoy quiet mornings on the welcoming front porch or relaxing evenings on the private rear deck. With three bedrooms and 1 bath this century home is i

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137 Fourth Street, Simcoe, ON , MLS #S13672094 , Image - 1

137 Fourth Street Midland, Simcoe, ON MLS® S13672094

Residential Freehold (Detached)

$389900.0

3 Beds
2 Baths
1500-2000 sq-ft

Set on an impressive 200-foot-deep lot, the property provides plenty of outdoor space to enjoy and tons of potential, along with parking for up to fiv

Detached Houses for Sale in Simcoe Under $500K - P6

Rosehaven Simcoe Woods