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Detached Houses for Sale in Simcoe Under $500K

Showing results 1 - 30 of 41

Square Yards Canada can assist you in finding the ideal detached homes in Simcoe. Browse the options of several detached homes for sale Under $500K in Simcoe comprising 1 to 5 beds. The detached houses for sale Under $500K in Simcoe are listed by owners and brokers offering first-rate amenities and services in upscale neighbourhoods in Simcoe.

Last Updated: December 18, 2025

25 Photos

81 Corner Brook Trail, Simcoe, ON , MLS #N12585902 , Image - 1

81 Corner Brook Trail Alcona, Innisfil, Simcoe, ON MLS® N12585902

Residential Freehold (Detached)

$440000.0

2 Beds
2 Baths
1100-1500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Located in an Adult Lifestyle community of Sandycove Acres this home offers thoughtfully selected upgrades t

24 Photos

86 Sixth Street, Simcoe, ON , MLS #S12638064 , Image - 1

86 Sixth Street Midland, Simcoe, ON MLS® S12638064

Residential Freehold (Detached)

$375000.0

3 Beds
1 Baths
1500-2000 sq-ft

CHARACTER-FILLED HOME WITH GEORGIAN BAY VIEWS, A 200 FT DEEP LOT, & READY TO BECOME YOUR PINTEREST DREAM HOME! Start your day on the enclosed front po

25 Photos

19 Wakunda Crescent, Simcoe, ON , MLS #S12505180 , Image - 1

19 Wakunda Crescent Rural Tiny, Tiny, Simcoe, ON MLS® S12505180

Residential Freehold (Detached)

$499900.0

3 Beds
1 Baths
700-1100 sq-ft

Top 5 Reasons You Will Love This Home: 1) Placed on a quiet crescent just off Awenda Park, this home is perfectly located for outdoor lovers, just ste

32 Photos

3 Courtland Street, Simcoe, ON , MLS #S12514032 , Image - 1

3 Courtland Street Orillia, Simcoe, ON MLS® S12514032

Residential Freehold (Detached)

$389000.0

2 Beds
1 Baths
1500-2000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Zoned Village Commercial, this unique property offers endless flexibility to live comfortably, run a busines

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

29 Photos

1981 TINY BEACHES Road S, Simcoe, ON , MLS #S12245692 , Image - 1

1981 TINY BEACHES Road S Rural Tiny, Tiny, Simcoe, ON MLS® S12245692

Residential Freehold (Detached)

$469000.0

Price drop by 2.1%

3 Beds
1 Baths
700-1100 sq-ft

Welcome to this meticulously maintained 2-bedroom, 1-bathroom three-season cottage, perfectly tucked away in one of the best pockets of Tiny Beaches.

23 Photos

1 GRAY Street, Simcoe, ON , MLS #S12185393 , Image - 1

1 GRAY Street Coldwater, Severn, Simcoe, ON MLS® S12185393

Residential Freehold (Detached)

$479900.0

Price drop by 8.6%

3 Beds
1 Baths
700-1100 sq-ft

Check out this very affordable and well maintained home. Three bedrooms on the main floor, attached garage, and a full, mostly finished basement with

10 Photos

17 Private Drive, Simcoe, ON , MLS #N12626674 , Image - 1

17 Private Drive Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N12626674

Residential Freehold (Detached)

$288000.0

< 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

22 Photos

119 Elizabeth Street, Simcoe, ON , MLS #N12626634 , Image - 1

119 Elizabeth Street Angus, Essa, Simcoe, ON MLS® N12626634

Residential Freehold (Detached)

$479000.0

2 Beds
1 Baths
700-1100 sq-ft

Discover this charming and well-maintained bungalow in the heart of Angus, featuring 2 bedrooms plus a versatile den/utility room and 1 full bathroom.

23 Photos

382 West Street N, Simcoe, ON , MLS #S12397748 , Image - 1

382 West Street N Orillia, Simcoe, ON MLS® S12397748

Residential Freehold (Detached)

$385000.0

2 Beds
1 Baths
700-1100 sq-ft

Attention Builders/Developers/Investors. This may be the development/investment property you've been looking for. Property is being sold primarily as

39 Photos

7692 Birch Drive, Simcoe, ON , MLS #S12248142 , Image - 1

7692 Birch Drive Rural Ramara, Ramara, Simcoe, ON MLS® S12248142

Residential Freehold (Detached)

$499800.0

2 Beds
1 Baths
< 700 sq-ft

Escape the City and Embrace Nature with This Charming Chalet-Style Retreat on the Black River. Tucked away among mature trees, this unique property of

4 Photos

2766 Ireton Street, Simcoe, ON , MLS #N12325788 , Image - 1

2766 Ireton Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N12325788

Residential Freehold (Detached)

$475000.0

3 Beds
1 Baths
700-1100 sq-ft

Incredible opportunity to build your dream home or cottage retreat on a premium lot just steps from one of Innisfil's most beautiful beaches. This exp

12 Photos

26 George Avenue, Simcoe, ON , MLS #S12397906 , Image - 1

26 George Avenue Wasaga Beach, Simcoe, ON MLS® S12397906

Residential Freehold (Detached)

$449900.0

3 Beds
1 Baths
700-1100 sq-ft

Opportunity Knocks! Attention Renovators, Contractors, Investors, Builders And First Time Buyers. 3 Bedroom Bungalow Located On A Quiet Cul-De Sac. K

39 Photos

11 Talsi Road, Simcoe, ON , MLS #N12467084 , Image - 1

11 Talsi Road Rural Essa, Essa, Simcoe, ON MLS® N12467084

Residential Freehold (Detached)

$285000.0

3 Beds
1 Baths
700-1100 sq-ft

Welcome to 11 Talsi Rd! As seen in the CBC Gem series Something Undone, this fully furnished 3-bedroom, 1-bathroom Viceroy Cedar Cottage offers the ul

35 Photos

2 WHITE PINES Trail, Simcoe, ON , MLS #S12596254 , Image - 1

2 WHITE PINES Trail Wasaga Beach, Simcoe, ON MLS® S12596254

Residential Freehold (Detached)

$134999.0

2 Beds
1 Baths
< 700 sq-ft

Enjoy your Seasonal Getaway at Wasaga Countrylife Resort! Now is the time to secure your seasonal cottage retreat! This immaculate 2009 Northlander Co

5 Photos

3763 Agnew Road, Simcoe, ON , MLS #S12591876 , Image - 1

3763 Agnew Road Washago, Severn, Simcoe, ON MLS® S12591876

Residential Freehold (Detached)

$299000.0

700-1100 sq-ft

Exceptional 1.58 acre lot just minutes to all amenities offered in Orillia. Marvelous opportunity to build your dream home and save on development cha

16 Photos

685 Reid Street, Simcoe, ON , MLS #N12590868 , Image - 1

685 Reid Street Alcona, Innisfil, Simcoe, ON MLS® N12590868

Residential Freehold (Detached)

$499900.0

1 Beds
1 Baths
< 700 sq-ft

* Permits are ready to build a second floor and a garage * This beautiful bungalow is located on a peaceful, low-traffic street with the added benefit

28 Photos

147 Dufferin Street, Simcoe, ON , MLS #S12172960 , Image - 1

147 Dufferin Street Orillia, Simcoe, ON MLS® S12172960

Residential Freehold (Detached)

$359000.0

Price drop by 5.5%

1 Beds
2 Baths
< 700 sq-ft

Welcome to this cute and cozy home located in Orillia's West Ward neighbourhood. This home has lots of natural light and plenty of potential for any f

23 Photos

132 Dunedin Street, Simcoe, ON , MLS #S12406088 , Image - 1

132 Dunedin Street Orillia, Simcoe, ON MLS® S12406088

Residential Freehold (Detached)

$299900.0

Price drop by 11.8%

2 Beds
1 Baths
< 700 sq-ft

Earn sweat equity. Perfect for a handyman. Steps to hospital, park, restaurants. Terrific starter for young ambitious couple. There is a garage but us

48 Photos

36 Tecumseth Pines Drive, Simcoe, ON , MLS #N12426310 , Image - 1

36 Tecumseth Pines Drive Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N12426310

Residential Freehold (Detached)

$499000.0

Price drop by 1.2%

3 Beds
2 Baths
1100-1500 sq-ft

Welcome to Tecumseth Pines, where peaceful country surroundings meet an active and welcoming 55+ lifestyle! Nestled in a beautiful community just minu

19 Photos

10 Grew Crescent, Simcoe, ON , MLS #S12563104 , Image - 1

10 Grew Crescent Penetanguishene, Simcoe, ON MLS® S12563104

Residential Freehold (Detached)

$499900.0

2 Beds
2 Baths
1500-2000 sq-ft

WALK TO THE WATER, ENJOY ONE-LEVEL LIVING & MAKE TIME FOR WHAT MATTERS MOST! Live the lifestyle you've earned in this beautifully maintained, low-main

25 Photos

1654 Viking Marina Road, Simcoe, ON , MLS #S12346817 , Image - 1

1654 Viking Marina Road Rural Severn, Severn, Simcoe, ON MLS® S12346817

Residential Freehold (Detached)

$485000.0

2 Beds
1 Baths
< 700 sq-ft

Cozy Waterfront Property w/ 50' X 450' Deep Lot. **Front on Matchedash Bay ** Bright & Spacious 2 Bedroom Detached Bungalow Backing onto Trail. Direct

36 Photos

7 60th Street S, Simcoe, ON , MLS #S12461340 , Image - 1

7 60th Street S Wasaga Beach, Simcoe, ON MLS® S12461340

Residential Freehold (Detached)

$399999.0

Price drop by 8.5%

1 Beds
1 Baths
700-1100 sq-ft

Nestled in the heart of Wasaga Beach, this property offers a unique opportunity to own a pieceof this vibrant community. This detached single-family h

27 Photos

2678 25th Side Road, Simcoe, ON , MLS #N12171168 , Image - 1

2678 25th Side Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N12171168

Residential Freehold (Detached)

$479999.0

Price drop by 6.8%

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

16 Photos

3520 Bennett Avenue, Simcoe, ON , MLS #S12546060 , Image - 1

3520 Bennett Avenue Rural Severn, Severn, Simcoe, ON MLS® S12546060

Residential Freehold (Detached)

$350000.0

1 Baths
700-1100 sq-ft

Small Home & a Beautiful Spot. Possibly this 350k value investment could be turned into 700-800k in a few short months. This property features lots (

50 Photos

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

40 Photos

4 Linden Lane, Simcoe, ON , MLS #N12477581 , Image - 1

4 Linden Lane Rural Innisfil, Innisfil, Simcoe, ON MLS® N12477581

Residential Freehold (Detached)

$329900.0

Price drop by 5.7%

2 Beds
2 Baths
1100-1500 sq-ft

Welcome Home! This Beautiful Monaco Style One Level Land Lease Home in the Adult Lifestyle Community of Sandy Cove Acres is Almost 1400 sq ft and is B

38 Photos

309 Manly Street, Simcoe, ON , MLS #S12509724 , Image - 1

309 Manly Street Midland, Simcoe, ON MLS® S12509724

Residential Freehold (Detached)

$424900.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to 309 Manly Street in Midland. Whether you are looking for an investment or just starting out this property has upside potential. Featuring

17 Photos

2763 Maple Trail, Simcoe, ON , MLS #S12488968 , Image - 1

2763 Maple Trail Rural Ramara, Ramara, Simcoe, ON MLS® S12488968

Residential Freehold (Detached)

$498000.0

3 Beds
1 Baths
700-1100 sq-ft

Spacious backyard with an impressive 44 ft x 452.27 ft lot, offering access to a crystal-clear lake. This updated bungalow is perfect for large famili

35 Photos

10 Allen Drive N, Simcoe, ON , MLS #S12472711 , Image - 1

10 Allen Drive N Wasaga Beach, Simcoe, ON MLS® S12472711

Residential Freehold (Detached)

$439900.0

2 Beds
2 Baths
700-1100 sq-ft

Stylishly Updated Bungalow in 55+ Parkbridge Community - Wasaga Beach Welcome to 10 Allen Dr N in Hometown, a sought-after 55+ Parkbridge land-lease c

13 Photos

2781 Sixth Line, Simcoe, ON , MLS #N12468474 , Image - 1

2781 Sixth Line Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N12468474

Residential Freehold (Detached)

Price On Request

5 Beds
2 Baths
2000-2500 sq-ft

A prime investment opportunity to acquire 1.631 acres of land located at the main entrance of Bradford's largest upcoming residential subdivision with

Shortlisted Properties

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