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Detached Houses for Sale in Simcoe Under $500K

Showing results 1 - 30 of 232

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: August 05, 2026

16 Photos

20 Regalia Way, Simcoe, ON , MLS #S13636334 , Image - 1

20 Regalia Way Innis-Shore, Barrie, Simcoe, ON MLS® S13636334

Residential Freehold (Detached)

$499000.0

4 Beds
3 Baths
3000-3500 sq-ft

Welcome to this stunning 4 Bedroom, 3 Washroom home offering over 3,000 sq.ft. of living space on a PREMIUM DEEP LOT of 39.66 x 189.19 ft backing onto

20 Photos

307 Tiny Beaches Road W, Simcoe, ON , MLS #S13632634 , Image - 1

307 Tiny Beaches Road W Rural Tiny, Tiny, Simcoe, ON MLS® S13632634

Residential Freehold (Detached)

$333000.0

3 Beds
1 Baths
< 700 sq-ft

Opportunity knocks! This charming four-season cottage is bursting with potential and ready for its next chapter. Owned by the same family for the past

33 Photos

16 Peel Street, Simcoe, ON , MLS #S13639434 , Image - 1

16 Peel Street Penetanguishene, Simcoe, ON MLS® S13639434

Residential Freehold (Detached)

$429900.0

3 Beds
1 Baths
1100-1500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Full of timeless charm and character, this beautifully restored gem delivers classic finishes and thoughtful

7 Photos

3282 OGDENS BEACH Road, Simcoe, ON , MLS #S13067678 , Image - 1

Unit-64, 3282 OGDENS BEACH Road Rural Tay, Tay, Simcoe, ON MLS® S13067678

Residential Freehold (Detached)

$169900.0

Price drop by 10.5%

2 Beds
2 Baths
< 700 sq-ft

Summer Sale-featured Cottage-save $40,935 compared to ordering new today! This brand-new 2-bedroom, 1-bathroom Cognashene Cottage offers 540 sq ft of

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

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

26 Photos

3322 Pleasant Road, Simcoe, ON , MLS #S13111484 , Image - 1

3322 Pleasant Road Rural Severn, Severn, Simcoe, ON MLS® S13111484

Residential Freehold (Detached)

$394900.0

Price drop by 1.3%

2 Beds
1 Baths
< 700 sq-ft

Exceptional Location Near Lake Couchiching; Just 200 yards from Lake Couchiching with convenient public access, this beautifully updated home offers t

24 Photos

21 Hawthorne Drive, Simcoe, ON , MLS #N13638464 , Image - 1

21 Hawthorne Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N13638464

Residential Freehold (Detached)

$239999.0

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

15 Photos

34 River Drive, Simcoe, ON , MLS #N13246682 , Image - 1

34 River Drive Angus, Essa, Simcoe, ON MLS® N13246682

Residential Freehold (Detached)

$469999.0

Price drop by 26.6%

4 Beds
2 Baths
1500-2000 sq-ft

Move into a community with possibilities to grow. This Detached 1 1/2 storey house on a lot of 70 ft X 230 ft offers a lot of potentials and is waiti

40 Photos

1987 Champlain Road, Simcoe, ON , MLS #S13562300 , Image - 1

1987 Champlain Road Rural Tiny, Tiny, Simcoe, ON MLS® S13562300

Residential Freehold (Detached)

$499900.0

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

Discover the perfect Georgian Bay getaway in the heart of Tiny Township. Located just one property back from the sparkling waters of Georgian Bay, thi

Open House : Sun Aug 09, 12:00 PM to 02:00 PM

48 Photos

7 Victory Crescent, Simcoe, ON , MLS #S13568862 , Image - 1

7 Victory Crescent Penetanguishene, Simcoe, ON MLS® S13568862

Residential Freehold (Detached)

$479900.0

Price drop by 4.0%

3 Beds
1 Baths
1100-1500 sq-ft

Welcome to 7 Victory Crescent in beautiful Penetanguishene! This bright, cozy, newly renovated 1.5-storey detached home offers 3 bedrooms and is fille

Open House : Sat Aug 08, 10:00 AM to 12:00 PM

30 Photos

24 Ridge Avenue, Simcoe, ON , MLS #S13607354 , Image - 1

24 Ridge Avenue Rural Ramara, Ramara, Simcoe, ON MLS® S13607354

Residential Freehold (Detached)

$450000.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to this charming bungalow in Lagoon City, just steps from the sandy shores of Lake Simcoe. Perfect for first-time buyers or those looking to d

37 Photos

33 Yarwood Road, Simcoe, ON , MLS #S13589840 , Image - 1

33 Yarwood Road Rural Tiny, Tiny, Simcoe, ON MLS® S13589840

Residential Freehold (Detached)

$449000.0

Price drop by 6.3%

3 Beds
1 Baths
700-1100 sq-ft

Your affordable Georgian Bay escape-move-in ready! Discover teh perfect blend of comfort and convenience at 33 Yarwood, located in the highly desirabl

6 Photos

5160 County Rd 13 N/A, Simcoe, ON , MLS #N13636242 , Image - 1

5160 County Rd 13 N/A Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13636242

Residential Freehold (Detached)

$300000.0

4 +1 Beds
3 Baths
1500-2000 sq-ft

Bring your vision and creativity to this classic 1.5 storey home, full of character and waiting for its next chapter. Offered AS IS, this property pre

33 Photos

55 Elgin Street, Simcoe, ON , MLS #S13568470 , Image - 1

55 Elgin Street Orillia, Simcoe, ON MLS® S13568470

Residential Freehold (Detached)

$369900.0

4 +0 Beds
2 Baths
1100-1500 sq-ft

Would you live here? This 4-bedroom home offers space, flexibility, and value in a growing Orillia neighbourhood just minutes from downtown and beauti

24 Photos

3 Illinois Crescent, Simcoe, ON , MLS #S13635778 , Image - 1

3 Illinois Crescent Wasaga Beach, Simcoe, ON MLS® S13635778

Residential Freehold (Detached)

$298000.0

2 Beds
2 Baths
700-1100 sq-ft

Welcome to 3 Illinois Crescent, a charming and affordable home in the sought-after Park Place community by Parkbridge! Just minutes from the beach, sh

27 Photos

678 Pinegrove Avenue, Simcoe, ON , MLS #N13593092 , Image - 1

678 Pinegrove Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13593092

Residential Freehold (Detached)

$449900.0

Price drop by 2.2%

2 Beds
1 Baths
< 700 sq-ft

Welcome to 678 Pinegrove Avenue! An excellent opportunity for first-time buyers, downsizers, or investors looking to get into the market. Ideally loca

38 Photos

5 Tecumseth Pines Drive, Simcoe, ON , MLS #N13635248 , Image - 1

5 Tecumseth Pines Drive Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13635248

Residential Freehold (Detached)

$399200.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to Tecumseth Pines - a sought-after active adult landlease community known for its welcoming atmosphere and like-minded residents, where neigh

35 Photos

477 Murray Road, Simcoe, ON , MLS #S13577436 , Image - 1

477 Murray Road Penetanguishene, Simcoe, ON MLS® S13577436

Residential Freehold (Detached)

$474900.0

Price drop by 4.1%

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

This well-maintained family home in Penetanguishene offers 3+1 bedrooms, 2+1 bathrooms, and beautiful views overlooking Martin's Valley. Ideally locat

27 Photos

1558 Champlain Road, Simcoe, ON , MLS #S13557406 , Image - 1

1558 Champlain Road Rural Tiny, Tiny, Simcoe, ON MLS® S13557406

Residential Freehold (Detached)

$424500.0

Price drop by 3.5%

3 Beds
1 Baths
700-1100 sq-ft

Looking for a true summer cottage escape? This three bedroom seasonal, full insulated cottage presents a fantastic opportunity to own an affordable re

27 Photos

66 Linden Lane, Simcoe, ON , MLS #N13593718 , Image - 1

66 Linden Lane Rural Innisfil, Innisfil, Simcoe, ON MLS® N13593718

Residential Freehold (Detached)

$229900.0

2 Beds
1 Baths
700-1100 sq-ft

Priced to SELL! Fast Closing Available! This upgraded 2-bedroom, 1-bath 'Sandalwood' model in *Sandycove Acres* offers turnkey retirement living with

25 Photos

7262 County Road 13 N/A, Simcoe, ON , MLS #N13633034 , Image - 1

7262 County Road 13 N/A Lisle, Adjala-Tosorontio, Simcoe, ON MLS® N13633034

Residential Freehold (Detached)

$444000.0

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 still close to shopping and other amenities. This bungal

22 Photos

350 McNicoll Street, Simcoe, ON , MLS #S13598820 , Image - 1

350 McNicoll Street Port McNicoll, Tay, Simcoe, ON MLS® S13598820

Residential Freehold (Detached)

$354900.0

2 Beds
1 Baths
< 700 sq-ft

Welcome to 350 McNicoll Street! Whether you're stepping into homeownership or looking to simplify your lifestyle, you'll appreciate the extensive impr

28 Photos

3 Awenda Avenue, Simcoe, ON , MLS #S13615820 , Image - 1

3 Awenda Avenue Wasaga Beach, Simcoe, ON MLS® S13615820

Residential Freehold (Detached)

$399000.0

2 Beds
1 Baths
700-1100 sq-ft

Top 5 Reasons You Will Love This Home: 1) Experience resort-style living in the secure, gated community of CountryLife Resort, where every day feels l

26 Photos

922 Elizabeth Avenue, Simcoe, ON , MLS #N13632452 , Image - 1

922 Elizabeth Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13632452

Residential Freehold (Detached)

$499000.0

2 Beds
1 Baths
700-1100 sq-ft

A Must See! Great Starter, Retirement Or Cottage Four Season home Within Commuting Distance To The GTA. Quiet, Dead End street In Great Family Communi

46 Photos

4274 Canal Road, Simcoe, ON , MLS #S13423908 , Image - 1

4274 Canal Road Rural Severn, Severn, Simcoe, ON MLS® S13423908

Residential Freehold (Detached)

$340000.0

Price drop by 14.8%

3 Beds
1 Baths
700-1100 sq-ft

Welcome to 4274 Canal Road, your waterfront escape on the renowned Trent-Severn Waterway. Situated on a private leased lot with 75 feet of unobstructe

25 Photos

168 Anne Street S, Simcoe, ON , MLS #S13631262 , Image - 1

168 Anne Street S Allandale, Barrie, Simcoe, ON MLS® S13631262

Residential Freehold (Detached)

$498000.0

2 Beds
1 Baths
700-1100 sq-ft

Opportunity knocks in Barrie. This RM1 / RM1(SP-528-HC) zoned property offers more than a typical residential purchase, with an approximately 66 ft. x

29 Photos

281 Elizabeth Street, Simcoe, ON , MLS #S13542080 , Image - 1

281 Elizabeth Street Midland, Simcoe, ON MLS® S13542080

Residential Freehold (Detached)

$489900.0

2 Beds
2 Baths
700-1100 sq-ft

Beautifully renovated and move-in ready, this charming 2-bedroom home is a wonderful opportunity in a desirable Midland neighbourhood. Thoughtfully up

29 Photos

26 South Street S, Simcoe, ON , MLS #S13606072 , Image - 1

26 South Street S Orillia, Simcoe, ON MLS® S13606072

Residential Freehold (Detached)

$460000.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to 26 South Street, a move-in ready home located in Orillia's desirable North Ward. Situated on an oversized, fenced lot, this property offers

37 Photos

469 Robert Street, Simcoe, ON , MLS #S13630326 , Image - 1

469 Robert Street Midland, Simcoe, ON MLS® S13630326

Residential Freehold (Detached)

$220000.0

3 Beds
1 Baths
1100-1500 sq-ft

Welcome to your next great opportunity in central Midland! Whether you're looking to restore the existing structure or start anew, the possibilities a

24 Photos

3184 Mosley Street, Simcoe, ON , MLS #S13530924 , Image - 1

3184 Mosley Street Wasaga Beach, Simcoe, ON MLS® S13530924

Residential Freehold (Detached)

$499900.0

Price drop by 16.3%

3 Beds
1 Baths
700-1100 sq-ft

Welcome to 3184 Mosley Street in beautiful Wasaga Beach! Ideally located on the beach side of Mosley Street, this charming bungalow offers easy access

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