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Houses for Sale in Penetanguishene ON Under $500K

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Are you looking for houses under $500k for sale in Penetanguishene ON? Square Yards Canada offers a wide selection of properties that cater to various budgets in Penetanguishene. Browse through detailed listings with HD images and guides to find the ideal property that fits your budget and preferences in Penetanguishene. Whether you’re looking to buy houses under under $500k in Penetanguishene ON for residential living or as investment opportunities, our listings allow you to filter by amenities, property age, number of bedrooms and much more. Explore a diverse range of Penetanguishene houses for sale under under $500k, including freehold homes, condos, and commercial properties.

Last Updated: August 12, 2026

26 Photos

27 Peel Street, Simcoe, ON , MLS #S13664216 , Image - 1

27 Peel Street Penetanguishene, Simcoe, ON MLS® S13664216

Residential Freehold (Detached)

$449000.0

3 Beds
1 Baths
1100-1500 sq-ft

Renovated Bungalow on an Oversized Lot in Downtown Penetanguishene! Welcome to this beautifully updated 3-bedroom bungalow, ideally located in the hea

31 Photos

15 Jennings Drive, Simcoe, ON , MLS #S13063960 , Image - 1

15 Jennings Drive Penetanguishene, Simcoe, ON MLS® S13063960

Residential Freehold (Semi-Detached )

$479900.0

Price drop by 5.7%

3 Beds
1 Baths
1100-1500 sq-ft

Lovely 3 bedroom, 1 bathroom semi detached home (only attached by the oversized garage) and sitting on a fully fenced large yard, backing onto the qui

1 Photos

59 Therrien Court Penetanguishene, Simcoe, ON MLS® S13647856

Residential Freehold (Semi-Detached )

$399900.0

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

Calling all first-time buyers or savvy investors! This handyman special offers a fantastic opportunity to create your dream home. With 4 Bedrooms, 2 b

42 Photos

3 Chamberlain Crescent, Simcoe, ON , MLS #S13639660 , Image - 1

3 Chamberlain Crescent Penetanguishene, Simcoe, ON MLS® S13639660

Residential Freehold (Att/Row/Townhouse)

$440000.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to easy, elegant living in the sought-after Bay Moorings land lease community by the shores of Penetanguishene Bay. This beautifully finished

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

19 Photos

73 Therrien Court, Simcoe, ON , MLS #S13543584 , Image - 1

73 Therrien Court Penetanguishene, Simcoe, ON MLS® S13543584

Residential Freehold (Semi-Detached )

$479900.0

2 Beds
2 Baths
700-1100 sq-ft

Welcome to 73 Therrien Court in Penetanguishene. This well-maintained, semi-detached turnkey home offers 2 bedrooms plus a versatile basement bonus ro

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

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

29 Photos

60 Church Street, Simcoe, ON , MLS #S13571092 , Image - 1

60 Church Street Penetanguishene, Simcoe, ON MLS® S13571092

Residential Freehold (Detached)

$349000.0

2 Beds
2 Baths
1500-2000 sq-ft

Warm, Inviting & Opportunity-Focused. Full of history and potential, this century-old 2-bedroom storey-and-a-half home is ready for someone with crea

25 Photos

178 Church Street, Simcoe, ON , MLS #S13446382 , Image - 1

178 Church Street Penetanguishene, Simcoe, ON MLS® S13446382

Residential Freehold (Detached)

$499900.0

Price drop by 5.7%

3 Beds
2 Baths
700-1100 sq-ft

Welcome to this charming and versatile home nestled on a quiet street in Penetanguishene. Offering two bedrooms and a full bathroom on the second leve

3 Photos

136 Fox Street, Simcoe, ON , MLS #S13077550 , Image - 1

136 Fox Street Penetanguishene, Simcoe, ON MLS® S13077550

Residential Freehold (Vacant Land)

$390000.0

Amazing views of Georgian Bay await on this expansive in-town lot measuring 161 ft by 197 ft, offering exceptional space to build your dream home with

34 Photos

11 Beck Boulevard, Simcoe, ON , MLS #S13454104 , Image - 1

Unit-108, 11 Beck Boulevard Penetanguishene, Simcoe, ON MLS® S13454104

Residential Condo & Other (Condo Apartment)

$429000.0

Price drop by 4.6%

2 Beds
2 Baths
900-999 sq-ft

Attention all boaters, water sport enthusiasts, retirees, first time buyers or those justlooking for the ease of condo living! Welcome to 11 Beck Blvd

28 Photos

39 Chamberlain Crescent, Simcoe, ON , MLS #S12956852 , Image - 1

39 Chamberlain Crescent Penetanguishene, Simcoe, ON MLS® S12956852

Residential Freehold (Att/Row/Townhouse)

$495000.0

Price drop by 5.7%

2 Beds
2 Baths
1100-1500 sq-ft

Live the lifestyle you've earned in this beautifully maintained, low-maintenance end unit bungalow just steps from Georgian Bay in the 55+ community o

11 Photos

71 Wozniak Road, Simcoe, ON , MLS #S13605380 , Image - 1

71 Wozniak Road Penetanguishene, Simcoe, ON MLS® S13605380

Residential Freehold (Vacant Land)

$119900.0

Imagine building the home or cottage you've always dreamed of in a peaceful Georgian Bay community where nature, recreation, and convenience come toge

27 Photos

11 Beck Boulevard, Simcoe, ON , MLS #S13597618 , Image - 1

Unit-402, 11 Beck Boulevard Penetanguishene, Simcoe, ON MLS® S13597618

Residential Condo & Other (Condo Apartment)

$457900.0

1 Beds
1 Baths
800-899 sq-ft

Live Above It All with an Unbeatable View! Welcome to this top-floor White Sands Condo, where every window frames stunning westerly vistas of Georgian

37 Photos

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

23 Maria Street Penetanguishene, Simcoe, ON MLS® S13251390

Residential Freehold (Detached)

$399000.0

Price drop by 4.8%

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

34 Photos

4 Beck Boulevard, Simcoe, ON , MLS #S13595046 , Image - 1

Unit-302, 4 Beck Boulevard Penetanguishene, Simcoe, ON MLS® S13595046

Residential Condo & Other (Condo Apartment)

$429900.0

1 +1 Beds
2 Baths
900-999 sq-ft

Boat. Relax. Explore. Where waterfront living meets carefree condominium ownership. This unit includes a boat slip with water & hydro, secure undergro

15 Photos

9 Wolfe Street, Simcoe, ON , MLS #S13571870 , Image - 1

9 Wolfe Street Penetanguishene, Simcoe, ON MLS® S13571870

Residential Freehold (Detached)

$399900.0

4 Beds
1 Baths
1100-1500 sq-ft

Welcome to 9 Wolfe Street in the heart of Penetanguishene! This spacious bungalow offers exceptional potential for first-time buyers, families, or inv

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),

22 Photos

28 Harriet Street, Simcoe, ON , MLS #S13576262 , Image - 1

28 Harriet Street Penetanguishene, Simcoe, ON MLS® S13576262

Residential Freehold (Detached)

$399900.0

3 Beds
1 Baths
1100-1500 sq-ft

Welcome to this charming 3-bedroom bungalow nestled on a generous 49' x 165' lot in the heart of Penetanguishene. This home is an excellent opportunit

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

14 Photos

570 Curry Road, Simcoe, ON , MLS #S12702470 , Image - 1

570 Curry Road Penetanguishene, Simcoe, ON MLS® S12702470

Residential Freehold (Vacant Land)

$399900.0

Top 5 Reasons You Will Love This Property: 1) Discover 2.64-acres of fully cleared, level land, an ideal canvas for bringing your dream home to life w

12 Photos

584 Curry Road, Simcoe, ON , MLS #S12702620 , Image - 1

584 Curry Road Penetanguishene, Simcoe, ON MLS® S12702620

Residential Freehold (Vacant Land)

$375000.0

Top 5 Reasons You Will Love This Property: 1) This generous 2-acre corner estate lot is fully cleared and ready to build, offering an exceptional oppo

13 Photos

1499 Tay Point Road, Simcoe, ON , MLS #S12702214 , Image - 1

1499 Tay Point Road Penetanguishene, Simcoe, ON MLS® S12702214

Residential Freehold (Vacant Land)

$244900.0

Top 5 Reasons You Will Love This Property: 1) This premium 1.78-acre lot is part of an exclusive release of newly created estate parcels, offering the

2 Photos

34 Forestdale Drive, Simcoe, ON , MLS #S13512250 , Image - 1

34 Forestdale Drive Penetanguishene, Simcoe, ON MLS® S13512250

Residential Freehold (Vacant Land)

$229900.0

Great 1.527 acre lot in beautiful estate subdivision. Opportunity to build a home with a walk out basement. Surround yourself with beautiful homes and

36 Photos

13 Centre Street, Simcoe, ON , MLS #S13127502 , Image - 1

13 Centre Street Penetanguishene, Simcoe, ON MLS® S13127502

Residential Freehold (Detached)

$464900.0

Price drop by 2.1%

2 Beds
1 Baths
1100-1500 sq-ft

HERE'S WHY 13 CENTRE STREET COULD BE YOUR NEXT MOVE ***QUIET STREET, GREAT LOCATION*** Tucked away on a dead-end street just steps from Georgian Bay w

36 Photos

5 Scott Street, Simcoe, ON , MLS #S13239696 , Image - 1

5 Scott Street Penetanguishene, Simcoe, ON MLS® S13239696

Residential Freehold (Detached)

$399900.0

2 Beds
1 Baths
1100-1500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Wake up every morning to sweeping views over Penetang Harbour and Georgian Bay, then unwind each evening fro

10 Photos

226 Church Street, Simcoe, ON , MLS #S12353549 , Image - 1

226 Church Street Penetanguishene, Simcoe, ON MLS® S12353549

Residential Freehold (Vacant Land)

$228000.0

< 700 sq-ft

**Municipal Water at property line**Prime location to build your dream house. Services At The Lot Line. massive 65 frontage with 150' Deep Lot Present

14 Photos

224 Church Street, Simcoe, ON , MLS #S13088942 , Image - 1

224 Church Street Penetanguishene, Simcoe, ON MLS® S13088942

Residential Freehold (Vacant Land)

$349900.0

Tucked away on a quiet street in the charming town of Penetanguishene, this just-under-two-acre parcel offers the perfect setting to bring your dream

5 Photos

81 Polish Avenue, Simcoe, ON , MLS #S13043332 , Image - 1

81 Polish Avenue Penetanguishene, Simcoe, ON MLS® S13043332

Residential Freehold (Vacant Land)

$129900.0

Welcome to Polish Avenue in Penetanguishene. An exceptional opportunity to build your dream home on this vacant lot! Located in a desirable and establ

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