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

23 Photos

1654 Viking Marina Road, Simcoe, ON , MLS #S13582598 , Image - 1

1654 Viking Marina Road Fesserton, Severn, Simcoe, ON MLS® S13582598

Residential Freehold (Detached)

$399999.0

Price drop by 11.1%

2 Beds
1 Baths
< 700 sq-ft

Enjoy this fully finished 2-bedroom, 1-bathroom home on the shores of beautiful Matchedash Bay. Inside, you'll find a comfortable, inviting home with

41 Photos

972 Gilmore Avenue, Simcoe, ON , MLS #N13430354 , Image - 1

972 Gilmore Avenue Lefroy, Innisfil, Simcoe, ON MLS® N13430354

Residential Freehold (Detached)

$430000.0

Price drop by 17.1%

2 Beds
1 Baths
700-1100 sq-ft

Welcome to this charming 2-bedroom, 1-bath home offering approximately 900 sq. ft. of living space on a quiet dead-end street in the desirable hamlet

5 Photos

134 Sunnidale Road, Simcoe, ON , MLS #S13773138 , Image - 1

134 Sunnidale Road Wasaga Beach, Simcoe, ON MLS® S13773138

Residential Freehold (Detached)

$399900.0

1 Beds
1 Baths
700-1100 sq-ft

Charming Cottage-Style Getaway with Development Potential! This delightful cottage-style retreat is ideally located within walking distance to the sou

2 Photos

127 Ardagh Road, Simcoe, ON , MLS #S13764072 , Image - 1

127 Ardagh Road Ardagh, Barrie, Simcoe, ON MLS® S13764072

Residential Freehold (Detached)

Price On Request

1 Beds
1 Baths
1100-1500 sq-ft

An exceptional opportunity for builders, developers, and investors to acquire 127 & 131 Ardagh Road, a combined development site with an approved Zoni

2 Photos

131 Ardagh Road, Simcoe, ON , MLS #S13764066 , Image - 1

131 Ardagh Road Ardagh, Barrie, Simcoe, ON MLS® S13764066

Residential Freehold (Detached)

Price On Request

1 Beds
1 Baths
700-1100 sq-ft

An exceptional opportunity for builders, developers, and investors to acquire 127 & 131 Ardagh Road, a combined development site with an approved Zoni

31 Photos

85 THEME PARK Drive, Simcoe, ON , MLS #S13740378 , Image - 1

Unit-168, 85 THEME PARK Drive Wasaga Beach, Simcoe, ON MLS® S13740378

Residential Freehold (Detached)

$110000.0

2 Beds
1 Baths
< 700 sq-ft

Nestled on a quiet dead-end street within Wasaga CountryLife Resort, Unit 168 offers exceptional privacy and a rare waterfront lot perfect for relaxed

28 Photos

8 Kenora Trail, Simcoe, ON , MLS #S13714298 , Image - 1

8 Kenora Trail Wasaga Beach, Simcoe, ON MLS® S13714298

Residential Freehold (Detached)

$199900.0

2 Beds
1 Baths
< 700 sq-ft

This immaculate Northlander Cottager Reflection at 8 Kenora Trail in Wasaga CountryLife Resort offers a beautifully maintained 3-bedroom, 1-bath layou

47 Photos

794097 124 Grey Road, Simcoe, ON , MLS #S13715586 , Image - 1

794097 124 Grey Road Singhampton, Clearview, Simcoe, ON MLS® S13715586

Residential Freehold (Detached)

$499000.0

3 Beds
2 Baths
700-1100 sq-ft

Welcome to this beautifully upgraded home in the heart of Singhampton, where convenience meets four-season outdoor adventure. This 3-bedroom, 2-bathro

36 Photos

38 Linden Lane, Simcoe, ON , MLS #N13721782 , Image - 1

38 Linden Lane Rural Innisfil, Innisfil, Simcoe, ON MLS® N13721782

Residential Freehold (Detached)

$449900.0

2 Beds
2 Baths
1100-1500 sq-ft

Are you looking to downsize and start living easy and stress-free? This move-in-ready 2-bedroom, 2-bathroom home in Sandy Cove Acres offers comfortabl

27 Photos

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

31 Photos

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

39 Photos

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

32 Photos

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

37 Photos

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

37 Photos

23 Maria Street, Simcoe, ON , MLS #S13251390 , Image - 1

23 Maria Street Penetanguishene, Simcoe, ON MLS® S13251390

Residential Freehold (Detached)

$389000.0

Price drop by 7.2%

3 Beds
1 Baths
1100-1500 sq-ft

Endless Potential Meets Small-Town Charm On A Large Lot At 23 Maria Street In The Heart Of Penetanguishene. This 3-Bedroom, 1-Bathroom Home Presents A

43 Photos

132 Park Road, Simcoe, ON , MLS #S13662464 , Image - 1

132 Park Road Rural Tiny, Tiny, Simcoe, ON MLS® S13662464

Residential Freehold (Detached)

$499900.0

2 Beds
2 Baths
1100-1500 sq-ft

Perfectly positioned between the sandy shores of Allenwood Beach in Tiny Township and Woodland Beach in Wasaga Beach, this charming chalet offers an e

46 Photos

4294 Canal Road, Simcoe, ON , MLS #S13658286 , Image - 1

4294 Canal Road Washago, Severn, Simcoe, ON MLS® S13658286

Residential Freehold (Detached)

$375000.0

3 Beds
2 Baths
700-1100 sq-ft

Discover this fully renovated 3-season waterfront cottage, offering a large lot, beautiful water views, and ample parking. Enjoy boating and swimming

32 Photos

76 Tecumseth Pines Drive, Simcoe, ON , MLS #N13640924 , Image - 1

76 Tecumseth Pines Drive Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13640924

Residential Freehold (Detached)

$479900.0

3 Beds
2 Baths
1100-1500 sq-ft

Upgrade to luxury in the premier adult community of Tecumseth Pines. This immaculate and upgraded home at 76 Tecumseth Pines is a 3 bedroom bungalow w

34 Photos

50 CABIN Crescent, Simcoe, ON , MLS #S13574550 , Image - 1

50 CABIN Crescent Wasaga Beach, Simcoe, ON MLS® S13574550

Residential Freehold (Detached)

$395000.0

Price drop by 7.1%

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

Welcome to resort-style living! A 4-season cottage right in town. 3 bedrooms, with a loft. Turn key and equipped with a gas forced-air furnace and A/C

8 Photos

418 Dominion Avenue, Simcoe, ON , MLS #S13445334 , Image - 1

418 Dominion Avenue Midland, Simcoe, ON MLS® S13445334

Residential Freehold (Detached)

$499990.0

Price drop by 15.3%

7 +1 Beds
3 Baths
2500-3000 sq-ft

Rare opportunity to own a spacious Victorian-style home in the heart of Midland with views of beautiful Georgian Bay. Offering approximately 3,000 sq.

9 Photos

354 Midland Avenue, Simcoe, ON , MLS #S13436614 , Image - 1

354 Midland Avenue Midland, Simcoe, ON MLS® S13436614

Residential Freehold (Detached)

$399990.0

Price drop by 16.7%

5 Beds
2 Baths
1500-2000 sq-ft

Perfect investment live in and run your business from this property, many of the commercial elements done, perfect for any type of office, Insurance,

30 Photos

2135 Champlain Road, Simcoe, ON , MLS #S13604942 , Image - 1

2135 Champlain Road Rural Tiny, Tiny, Simcoe, ON MLS® S13604942

Residential Freehold (Detached)

$449000.0

2 Beds
1 Baths
700-1100 sq-ft

Visit the REALTOR website for further information about this Listing. Year-round home or cottage in a natural setting, near Sawlog Point in Tiny. 2 B

27 Photos

2678 25th Side Road, Simcoe, ON , MLS #N13074692 , Image - 1

2678 25th Side Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N13074692

Residential Freehold (Detached)

$425000.0

Price drop by 9.6%

1 Beds
1 Baths
700-1100 sq-ft

A rare opportunity to live and build in beautiful Innisfil Beach. This oversized lot of 50 X 200 feet with and approximate 700 sq ft bungalow frame fe

21 Photos

30 Illinois Crescent, Simcoe, ON , MLS #S13558966 , Image - 1

30 Illinois Crescent Wasaga Beach, Simcoe, ON MLS® S13558966

Residential Freehold (Detached)

$479000.0

2 +0 Beds
2 Baths
1500-2000 sq-ft

Welcome to 30 Illinois Crescent, nestled in the heart of Park Place Estates. Wasaga Beach's premier 55+ gated community, where comfort, connection, an

14 Photos

117 Fox Street, Simcoe, ON , MLS #S13577448 , Image - 1

117 Fox Street Penetanguishene, Simcoe, ON MLS® S13577448

Residential Freehold (Detached)

$323000.0

4 Beds
1 Baths
1500-2000 sq-ft

Prime Investment in Penetanguishene Attention investors and flippers! This solid 4-bedroom home sits on an impressive 0.54-acre lot (89 ft x 264 ft),

18 Photos

48 Mcarthur Drive, Simcoe, ON , MLS #S13455582 , Image - 1

48 Mcarthur Drive Penetanguishene, Simcoe, ON MLS® S13455582

Residential Freehold (Detached)

$398000.0

Price drop by 6.3%

1 Beds
1 Baths
< 700 sq-ft

Location, location! This Charming turn key, open concept cottage, located in prestigious waterfront community, is within minutes walk to nearby beac

45 Photos

13 WHITE PINES Trail, Simcoe, ON , MLS #S13492930 , Image - 1

13 WHITE PINES Trail Wasaga Beach, Simcoe, ON MLS® S13492930

Residential Freehold (Detached)

$179900.0

1 Beds
2 Baths
700-1100 sq-ft

Welcome to 13 White Pines Trail in the highly sought-after Wasaga CountryLife Resort, offering an exceptional blend of craftsmanship, comfort, and wat

45 Photos

1 WHITE PINES Trail, Simcoe, ON , MLS #S13436258 , Image - 1

1 WHITE PINES Trail Wasaga Beach, Simcoe, ON MLS® S13436258

Residential Freehold (Detached)

$169900.0

2 Beds
1 Baths
700-1100 sq-ft

Nestled within the sought-after Wasaga CountryLife Resort, this charming woodland Park Muskoka at 1 White Pines Trail offers a rare blend of privacy,

4 Photos

2766 Ireton Street, Simcoe, ON , MLS #N13412556 , Image - 1

2766 Ireton Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N13412556

Residential Freehold (Detached)

$444900.0

3 Beds
1 Baths
700-1100 sq-ft

Reduced Price!! Incredible opportunity to build your dream home or cottage retreat on a premium lot just steps from one of Innisfil's most beautiful b

10 Photos

17 Private Drive, Simcoe, ON , MLS #N13173370 , Image - 1

17 Private Drive Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13173370

Residential Freehold (Detached)

$248000.0

< 700 sq-ft

Rare Waterfront Opportunity On The Holland River! This 50 X 100 Ft Property Is Accessed Via A Private Road With Direct Access To Yonge St Offering A P

Detached Houses for Sale in Simcoe Under $500K - P8

Rosehaven Simcoe Woods