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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: June 21, 2026

22 Photos

101 Linden Lane, Simcoe, ON , MLS #N13096834 , Image - 1

101 Linden Lane Rural Innisfil, Innisfil, Simcoe, ON MLS® N13096834

Residential Freehold (Detached)

$249900.0

2 Beds
1 Baths
1100-1500 sq-ft

Welcome to the sought-after Sandy Cove retirement community, an adult lifestyle neighborhood for residents 55+! This charming 2-bedroom, 1-bath Sandal

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)

$124999.0

Price drop by 7.4%

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

35 Photos

18 Cherrywood Lane, Simcoe, ON , MLS #N13235880 , Image - 1

18 Cherrywood Lane Rural Innisfil, Innisfil, Simcoe, ON MLS® N13235880

Residential Freehold (Detached)

$389900.0

2 Beds
1 Baths
1100-1500 sq-ft

Welcome to this stunning Ranch Style Bungalow, renovated top to bottom home, Located in the vibrant adult community of Sandy Cove Acres. This 2 bedroo

21 Photos

249 Harvey Street, Simcoe, ON , MLS #S13460470 , Image - 1

249 Harvey Street Orillia, Simcoe, ON MLS® S13460470

Residential Freehold (Detached)

$499888.0

4 Beds
3 Baths
1500-2000 sq-ft

Step Into A Piece Of Orillia's History, Updated For Modern Living. This Full Brick, Century Home Is Nestled On A Quiet Street, Offering The Perfect Bl

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

27 Photos

66 Linden Lane, Simcoe, ON , MLS #N13259408 , Image - 1

66 Linden Lane Rural Innisfil, Innisfil, Simcoe, ON MLS® N13259408

Residential Freehold (Detached)

$248000.0

2 Beds
1 Baths
700-1100 sq-ft

**EXCELLENT VALUE!** This upgraded 2-bedroom, 1-bath 'Sandalwood' model in *Sandycove Acres* offers turnkey retirement living with all the comforts yo

25 Photos

7262 County Road 13 N/A, Simcoe, ON , MLS #N13142136 , Image - 1

7262 County Road 13 N/A Lisle, Adjala-Tosorontio, Simcoe, ON MLS® N13142136

Residential Freehold (Detached)

$479000.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to 7262 County Rd 13 - a great starter home located in a quiet rural location that is close to shopping and other amenities. This bungalow has

20 Photos

54 Homewood Avenue, Simcoe, ON , MLS #S13451232 , Image - 1

54 Homewood Avenue Wasaga Beach, Simcoe, ON MLS® S13451232

Residential Freehold (Detached)

$423000.0

3 Beds
1 Baths
700-1100 sq-ft

Cottage Life on Georgian Bay-what does it mean to you? Is it an easy stroll to New Wasaga Beach or cozy nights by the fire with sand between your toes

38 Photos

1207 Tiny Beaches Road S, Simcoe, ON , MLS #S13138420 , Image - 1

1207 Tiny Beaches Road S Rural Tiny, Tiny, Simcoe, ON MLS® S13138420

Residential Freehold (Detached)

$499000.0

Price drop by 7.6%

3 Beds
1 Baths
700-1100 sq-ft

Welcome to this charming cottage retreat nestled in the heart of Tiny Beaches Road, just a short stroll from the stunning blue waters of Georgian Bay.

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

8 Photos

50 DUNEDIN Street, Simcoe, ON , MLS #S13440270 , Image - 1

50 DUNEDIN Street Orillia, Simcoe, ON MLS® S13440270

Residential Freehold (Detached)

$399000.0

3 Beds
1 Baths
700-1100 sq-ft

The property includes an approximately 1,100 sq. ft. house currently rented for $950 per month plus utilities and is in poor condition. The house has

4 Photos

339 Gill Street, Simcoe, ON , MLS #S13185992 , Image - 1

339 Gill Street Orillia, Simcoe, ON MLS® S13185992

Residential Freehold (Detached)

$499990.0

< 700 sq-ft

Welcome To 339 Gill Street! This Corner Property Is One Of A Kind! Suitable For Many Uses Including An Apartment Building Or A Townhouse Project. R2 Z

16 Photos

126 Woodward Drive, Simcoe, ON , MLS #S13061820 , Image - 1

126 Woodward Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13061820

Residential Freehold (Detached)

$439000.0

Price drop by 15.6%

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

Year round 3 bedroom raised bungalow with a fully finished basement in a prime location just south of Balm Beach. Enjoy 4 season living just a short d

24 Photos

1 Gidley Court, Simcoe, ON , MLS #S13121418 , Image - 1

1 Gidley Court Penetanguishene, Simcoe, ON MLS® S13121418

Residential Freehold (Detached)

$479900.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to 1 Gidley Court in Penetanguishene, located in the desirable 55+ community of the Village of Bay Moorings just a short walk to Georgian Bay

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

37 Photos

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

23 Maria Street Penetanguishene, Simcoe, ON MLS® S13251390

Residential Freehold (Detached)

$419000.0

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

20 Photos

439 Sundial Drive, Simcoe, ON , MLS #S12491190 , Image - 1

439 Sundial Drive Orillia, Simcoe, ON MLS® S12491190

Residential Freehold (Detached)

$449999.0

Price drop by 14.3%

3 Beds
1 Baths
700-1100 sq-ft

Situated on a generous 0.49-acre lot (approximately 60' x 330'), this raised bungalow offers a perfect blend of space and location. The home features

19 Photos

10 Grew Crescent, Simcoe, ON , MLS #S13083172 , Image - 1

10 Grew Crescent Penetanguishene, Simcoe, ON MLS® S13083172

Residential Freehold (Detached)

$489900.0

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

29 Photos

1981 Tiny Beaches Road S, Simcoe, ON , MLS #S13236488 , Image - 1

1981 Tiny Beaches Road S Rural Tiny, Tiny, Simcoe, ON MLS® S13236488

Residential Freehold (Detached)

$399900.0

3 Beds
1 Baths
< 700 sq-ft

SPOTLESS AND WELL MAINTAINED 3 SEASON COTTAGE IN TINY BEACHES, SHORT DISTANCE TO WOODLAND BEACH AND EASY ACCESS TO CONVENIENCE STORE AND SHORT DISTAN

32 Photos

173 Barrie Road, Simcoe, ON , MLS #S13227952 , Image - 1

173 Barrie Road Orillia, Simcoe, ON MLS® S13227952

Residential Freehold (Detached)

$399999.0

Price drop by 14.9%

3 Beds
2 Baths
700-1100 sq-ft

Welcome to 173 Barrie Road, a wonderful 2 storey detached house on 50ft lot perfect for first-timebuyers or investors, located in the heart of Orillia

28 Photos

147 Dufferin Street, Simcoe, ON , MLS #S13049438 , Image - 1

147 Dufferin Street Orillia, Simcoe, ON MLS® S13049438

Residential Freehold (Detached)

$359000.0

1 Beds
2 Baths
< 700 sq-ft

Welcome to your very own small but mighty gem in Orillia's sought-after West Ward! This cute and cozy home is bursting with charm, natural light, and

47 Photos

2233 North Orr Lake Road, Simcoe, ON , MLS #S13230420 , Image - 1

2233 North Orr Lake Road Rural Springwater, Springwater, Simcoe, ON MLS® S13230420

Residential Freehold (Detached)

$498000.0

2 Beds
1 Baths
< 700 sq-ft

Welcome to your turnkey waterfront escape on spring fed Orr Lake, just one hour north of Toronto. This tastefully renovated 2 Bedroom cottage is where

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

35 Photos

10 Allen Drive N, Simcoe, ON , MLS #S12916764 , Image - 1

10 Allen Drive N Wasaga Beach, Simcoe, ON MLS® S12916764

Residential Freehold (Detached)

$399900.0

2 Beds
2 Baths
700-1100 sq-ft

Stylishly Updated Bungalow in Sought-After 55+ Parkbridge Community - Wasaga Beach. Welcome to 10 Allen Dr N in Hometown, a desirable 55+ Parkbridge l

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

24 Photos

21 Hawthorne Drive, Simcoe, ON , MLS #N13155562 , Image - 1

21 Hawthorne Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N13155562

Residential Freehold (Detached)

$275000.0

3 Beds
1 Baths
700-1100 sq-ft

Top 5 Reasons You Will Love This Home: 1) An upgrade packed home that delivers exceptional value at every turn, even before stepping inside you'll not

44 Photos

330 Third Street, Simcoe, ON , MLS #S13044912 , Image - 1

330 Third Street Midland, Simcoe, ON MLS® S13044912

Residential Freehold (Detached)

$459000.0

Price drop by 4.2%

2 Beds
2 Baths
700-1100 sq-ft

Timeless Charm & Modern Comfort in the Heart of Midland! Welcome to a home that instantly feels just right. This beautifully updated 2-storey century

12 Photos

26 George Avenue, Simcoe, ON , MLS #S13157944 , Image - 1

26 George Avenue Wasaga Beach, Simcoe, ON MLS® S13157944

Residential Freehold (Detached)

$399900.0

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

40 Photos

326 Lafontaine Road W, Simcoe, ON , MLS #S12920684 , Image - 1

326 Lafontaine Road W Lafontaine, Tiny, Simcoe, ON MLS® S12920684

Residential Freehold (Detached)

$499900.0

Price drop by 4.8%

5 Beds
2 Baths
2000-2500 sq-ft

Spacious five-bedroom family home with a versatile layout, premium features, and C5 zoning for added usage possibilities. This bright and welcoming re

5 Photos

134 Sunnidale Road, Simcoe, ON , MLS #S13150982 , Image - 1

134 Sunnidale Road Wasaga Beach, Simcoe, ON MLS® S13150982

Residential Freehold (Detached)

$428000.0

1 Beds
1 Baths
700-1100 sq-ft

Nestled on a beautifully treed lot in the heart of Wasaga Beach, this charming 1+ bedroom property offers an incredible opportunity for year-round liv

50 Photos

48 Madawaska Trail, Simcoe, ON , MLS #S13150930 , Image - 1

48 Madawaska Trail Wasaga Beach, Simcoe, ON MLS® S13150930

Residential Freehold (Detached)

$405900.0

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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