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Simcoe Duplex Houses for Sale

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Last Updated: June 20, 2025

30 Photos

361 Third Street, Simcoe, ON , MLS #S12165267 , Image - 1

361 Third Street Midland, Simcoe, ON MLS® S12165267

Residential Freehold (Duplex)

$559900.0

4 Beds
2 Baths
1500-2000 sq-ft

ATTENTION! Assumable Mortgage available with this property - 6 years left at 2.5%! Looking for a solid investment opportunity with great potential? Th

39 Photos

452 Hannah Street, Simcoe, ON , MLS #S12232438 , Image - 1

452 Hannah Street Midland, Simcoe, ON MLS® S12232438

Residential Freehold (Duplex)

$724000.0

4 Beds
3 Baths
2000-2500 sq-ft

Welcome to 452 Hannah St, Midland! A fully renovated legal duplex offering 4 bedrooms and 2.5 bathrooms across a spacious and functional layout. This

23 Photos

36 Porritt Street, Simcoe, ON , MLS #S11946408 , Image - 1

36 Porritt Street Ardagh, Barrie, Simcoe, ON MLS® S11946408

Residential Freehold (Duplex)

$759900.0

Price drop by 0.7%

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

Turnkey investment opportunity! Very clean and well-maintained legal duplex in quiet southwest end neighborhood. Current upstairs tenant paying 2300.

38 Photos

18 Eugenia Street, Simcoe, ON , MLS #S12180740 , Image - 1

18 Eugenia Street Codrington, Barrie, Simcoe, ON MLS® S12180740

Residential Freehold (Duplex)

$649500.0

Price drop by 7.1%

4 Beds
3 Baths
1500-2000 sq-ft

Amazing opportunity for generational living or to live in one unit & rent 2nd. Located on a quiet street in an area of executive homes within walking

37 Photos

679 Montreal Street, Simcoe, ON , MLS #S12028300 , Image - 1

679 Montreal Street Midland, Simcoe, ON MLS® S12028300

Residential Freehold (Duplex)

$725000.0

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

Well maintained maintenance free duplex located on Midland's west side offering a 3 Bdrm Unit and a 2 Bdrm unit with each their own driveways, separa

36 Photos

15 Valleybrook Road, Simcoe, ON , MLS #S12222907 , Image - 1

15 Valleybrook Road Rural Barrie Southeast, Barrie, Simcoe, ON MLS® S12222907

Residential Freehold (Duplex)

$999888.0

5 Beds
4 Baths
2500-3000 sq-ft

Attention investors & first time home buyers! 5% return! Duplexed or live in one and rent the other out $2300/mo. Bright and Open Concept Legal Duplex

26 Photos

8 Summerset Place, Simcoe, ON , MLS #N11945884 , Image - 1

8 Summerset Place Angus, Essa, Simcoe, ON MLS® N11945884

Residential Freehold (Duplex)

$624900.0

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

2 Unit home (Duplex) on a massive in town property 82.30 ft x 164.99 ft/ 0.31 acres in a very nice Angus neighborhood across from retail. Each unit ha

15 Photos

2 Christine Place, Simcoe, ON , MLS #S12083993 , Image - 1

2 Christine Place Orillia, Simcoe, ON MLS® S12083993

Residential Freehold (Duplex)

$630000.0

Price drop by 9.9%

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

Bright & cozy legal duplex in the heart of Orillia with 2 self-contained units, each approx. 1,025 sq ft. Upper unit features 3 bedrooms, laminate flo

37 Photos

43 Charlbrook Avenue, Simcoe, ON , MLS #S12038620 , Image - 1

43 Charlbrook Avenue Cundles East, Barrie, Simcoe, ON MLS® S12038620

Residential Freehold (Duplex)

$725000.0

Price drop by 3.3%

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

Discover the exceptional opportunity at 43 Charlbrook Ave in Barrie a newly renovated legal duplex that perfectly combines comfort and versatility. Th

50 Photos

285 Maple Street, Simcoe, ON , MLS #S12204621 , Image - 1

285 Maple Street Collingwood, Simcoe, ON MLS® S12204621

Residential Freehold (Duplex)

$1850000.0

5 Beds
4 Baths
3500-5000 sq-ft

Charming Century Home on Coveted Tree Street in Central Collingwood. Nestled on one of Collingwood's most sought-after tree-lined streets, this beauti

39 Photos

398 Mary Street, Simcoe, ON , MLS #S12202791 , Image - 1

398 Mary Street Orillia, Simcoe, ON MLS® S12202791

Residential Freehold (Duplex)

$699900.0

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

Get ready to fall in love with this family friendly duplex! Tucked away on a lovely street in the heart of Orillia, this legal duplex is more than jus

20 Photos

266 Galloway Boulevard, Simcoe, ON , MLS #S12032293 , Image - 1

266 Galloway Boulevard Midland, Simcoe, ON MLS® S12032293

Residential Freehold (Duplex)

$569900.0

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

DUPLEX - DETACHED RAISED BUNGALOW with 2 LEGAL SUITES - Attention All Investors - Looking to add to your existing real estate portfolio? Looking to be

33 Photos

10 Clarence Avenue, Simcoe, ON , MLS #S12217738 , Image - 1

10 Clarence Avenue Penetanguishene, Simcoe, ON MLS® S12217738

Residential Freehold (Duplex)

$769900.0

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

Beautifully updated home with sunset water views over Georgian Bay, located on a quiet street in Penetanguishene! Legal duplex with a VACANT walk-out

40 Photos

66 Matchedash Street S, Simcoe, ON , MLS #S12214099 , Image - 1

66 Matchedash Street S Orillia, Simcoe, ON MLS® S12214099

Residential Freehold (Duplex)

$549000.0

3 Beds
2 Baths
1500-2000 sq-ft

Investors Opportunity! Interior updated and vacant - ready for you to set the rents and choose your own tenants. 66 Matchedash St S is located in the

47 Photos

274 Mississaga Street W, Simcoe, ON , MLS #S12173953 , Image - 1

274 Mississaga Street W Orillia, Simcoe, ON MLS® S12173953

Residential Freehold (Duplex)

$724900.0

Price drop by 3.3%

3 Beds
4 Baths
1500-2000 sq-ft

CHARMING LEGAL NON-CONFORMING DUPLEX. This beautifully renovated legal non-conforming duplex in the West Ward offers a unique opportunity for investor

21 Photos

135 Gunn Street, Simcoe, ON , MLS #S12206522 , Image - 1

135 Gunn Street Wellington, Barrie, Simcoe, ON MLS® S12206522

Residential Freehold (Duplex)

$699900.0

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

Top 5 Reasons You Will Love This Home: 1) Exceptional investment renovated in 2020 2) Two units, featuring a two bedroom unit and a one bedroom unit,

25 Photos

42 Westminster Circle, Simcoe, ON , MLS #S12206260 , Image - 1

42 Westminster Circle Innis-Shore, Barrie, Simcoe, ON MLS® S12206260

Residential Freehold (Duplex)

$1149000.0

4 +2 Beds
6 Baths
2500-3000 sq-ft

Legal Duplex in Family Friendly Circle. Main unit features Large Master with walk in Closet, 5 pc Ensuite with Soaker Tub and Glass Shower. Jack an

40 Photos

44 St Peter Street, Simcoe, ON , MLS #S11996758 , Image - 1

44 St Peter Street Collingwood, Simcoe, ON MLS® S11996758

Residential Freehold (Duplex)

$845500.0

Price drop by 10.8%

4 +1 Beds
3 Baths
2000-2500 sq-ft

This beautiful legal duplex offers an excellent opportunity for both homeowners and investors, with the flexibility to live in one unit while renting

25 Photos

3081 Hogback Road, Simcoe, ON , MLS #S12167485 , Image - 1

3081 Hogback Road New Lowell, Clearview, Simcoe, ON MLS® S12167485

Residential Freehold (Duplex)

$999999.0

Price drop by 6.5%

5 Beds
4 Baths
3500-5000 sq-ft

Welcome to this exceptional large family home offering space, comfort, and versatility, both inside and out. Set on a picturesque 2.74-acre corner lot

41 Photos

12 Dufferin Street, Simcoe, ON , MLS #S12203720 , Image - 1

Unit-1, 2, C, 12 Dufferin Street Sanford, Barrie, Simcoe, ON MLS® S12203720

Residential Freehold (Duplex)

$799900.0

4 +1 Beds
3 Baths
700-1100 sq-ft

Investors!!! Fabulous Opportunity To Own Your Own Investment Property! This Fabulous All Brick, Legal 2 Unit Bungalow + Newly Built Coach House Unit I

26 Photos

258 Ruby Street, Simcoe, ON , MLS #S12195102 , Image - 1

258 Ruby Street Midland, Simcoe, ON MLS® S12195102

Residential Freehold (Duplex)

$575000.0

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

ATTENTION! Assumable Mortgage available with this property - 6 years left at 2.5%! Turnkey duplex offers strong rental potential with two fully separ

25 Photos

311 James Street E, Simcoe, ON , MLS #S12010012 , Image - 1

311 James Street E Orillia, Simcoe, ON MLS® S12010012

Residential Freehold (Duplex)

$639900.0

Price drop by 4.5%

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

Charming Bungalow with Income Potential! This adorable & well-maintained 3-bedroom bungalow, Close to Highway 11 and 12 for easy commuting. Whether yo

34 Photos

210 Southview Road, Simcoe, ON , MLS #S12195694 , Image - 1

210 Southview Road South Shore, Barrie, Simcoe, ON MLS® S12195694

Residential Freehold (Duplex)

$749000.0

4 Beds
3 Baths
2000-2500 sq-ft

SPACIOUS HOME WITH A REGISTERED SECOND SUITE IN A PRIME INNISHORE NEIGHBOURHOOD! Welcome to 210 Southview Road, a standout opportunity in Barries soug

50 Photos

6903 36/37 Nottawasaga Side Road E, Simcoe, ON , MLS #S12184235 , Image - 1

6903 36/37 Nottawasaga Side Road E Rural Clearview, Clearview, Simcoe, ON MLS® S12184235

Residential Freehold (Duplex)

$2250000.0

4 Beds
4 Baths
3500-5000 sq-ft

Located on the prestigious 36/37 Nottawasaga Side Road affectionately known by locals as Millionaires Row this one-of-a-kind, custom-built estate offe

21 Photos

127 Burton Ave Avenue, Simcoe, ON , MLS #S12193586 , Image - 1

127 Burton Ave Avenue Allandale, Barrie, Simcoe, ON MLS® S12193586

Residential Freehold (Duplex)

$699000.0

3 Beds
2 Baths
1500-2000 sq-ft

Legal Duplex in Prime Allandale Location Steps to the Water & GO Station!A rare opportunity to own a legal duplex in the heart of Allandale, just a s

21 Photos

319 Oxford Street, Simcoe, ON , MLS #S11983507 , Image - 1

319 Oxford Street Orillia, Simcoe, ON MLS® S11983507

Residential Freehold (Duplex)

$699000.0

Price drop by 4.1%

6 Beds
4 Baths
1100-1500 sq-ft

LEGAL DUPLEX - Completely Renovated From Top To Bottom Including New Roof, Furnace And A/C. This Duplex Has To Much To List And Is A Must See. Highlig

31 Photos

105 Monique Crescent, Simcoe, ON , MLS #S12189959 , Image - 1

105 Monique Crescent East Bayfield, Barrie, Simcoe, ON MLS® S12189959

Residential Freehold (Duplex)

$799500.0

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

Fully Renovated Legal 2 Unit Bungalow in turn key condition. Perfect for investors or savy home owners that want to live in one unit and offset expens

38 Photos

1923 10th Line, Simcoe, ON , MLS #N11993217 , Image - 1

1923 10th Line Rural Innisfil, Innisfil, Simcoe, ON MLS® N11993217

Residential Freehold (Duplex)

$2724900.0

Price drop by 6.0%

7 Beds
6 Baths
5000 + sq-ft

MULTI-GENERATIONAL LIVING ON 1.3 ACRES WITH A FULL SECONDARY DWELLING! This exceptional property, located just outside the charming community of Strou

41 Photos

46 Eugenia Street, Simcoe, ON , MLS #S12183375 , Image - 1

46 Eugenia Street Codrington, Barrie, Simcoe, ON MLS® S12183375

Residential Freehold (Duplex)

$1399999.0

8 Beds
2 Baths
1500-2000 sq-ft

Legal Duplex! Two 4 bedroom apartments side-by-side. Upgraded with many new stainless steel appliances, including washer and dryers. Two kitchens, 2 l

8 Photos

12 Bronte Crescent, Simcoe, ON , MLS #S12162450 , Image - 1

12 Bronte Crescent Letitia Heights, Barrie, Simcoe, ON MLS® S12162450

Residential Freehold (Duplex)

$699999.0

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

Looking for a great investment opportunity or your first home? This updated legal duplex in Barrie is the perfect choice! Featuring an updated 3-bedro

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