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Houses for Sale in Orangeville ON Under $5 Million

Showing results 1 - 30 of 148

Are you looking for houses under $5m for sale in Orangeville ON? Square Yards Canada offers a wide selection of properties that cater to various budgets in Orangeville. Browse through detailed listings with HD images and guides to find the ideal property that fits your budget and preferences in Orangeville. Whether you’re looking to buy houses under under $5m in Orangeville 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 Orangeville houses for sale under under $5m, including freehold homes, condos, and commercial properties.

Last Updated: September 27, 2026

42 Photos

27 Winterton Court, Dufferin, ON , MLS #W13832164 , Image - 1

27 Winterton Court Orangeville, Dufferin, ON MLS® W13832164

Residential Freehold (Att/Row/Townhouse)

$699900.0

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

Welcome to 27 Winterton Court, a gorgeous 3 bedroom freehold townhome with a big rec room and full bathroom in the basement, located in one of Orangev

38 Photos

124 Jordan Drive, Dufferin, ON , MLS #W13580804 , Image - 1

124 Jordan Drive Orangeville, Dufferin, ON MLS® W13580804

Residential Freehold (Detached)

$999000.0

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

Beautiful Home Is Located On Quiet Street, Close To Parks & Amenities. Great for Commuters! Meticulously Maintained & Professionally Landscaped Front

37 Photos

22 Winterton Court, Dufferin, ON , MLS #W13797912 , Image - 1

22 Winterton Court Orangeville, Dufferin, ON MLS® W13797912

Residential Freehold (Att/Row/Townhouse)

$699500.0

3 Beds
3 Baths
1100-1500 sq-ft

The kind of home that makes starting your next chapter feel easy...Warm, thoughtfully updated and filled with personality, this 3-bedroom, 3-bathroom

31 Photos

27 Rustic Crescent, Dufferin, ON , MLS #W13719760 , Image - 1

27 Rustic Crescent Orangeville, Dufferin, ON MLS® W13719760

Residential Freehold (Detached)

$629900.0

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

Spacious. Versatile. Connected. Welcome to 27 Rustic Street in the heart of Orangeville-a beautifully maintained 3-level side split offering exception

50 Photos

333 Lisa Marie Drive, Dufferin, ON , MLS #W13803010 , Image - 1

333 Lisa Marie Drive Orangeville, Dufferin, ON MLS® W13803010

Residential Freehold (Detached)

$889900.0

3 Beds
3 Baths
1500-2000 sq-ft

Welcome to this beautifully maintained 3-bedroom, 3-bathroom home in a welcoming, family-friendly Orangeville neighbourhood. Set on a corner lot with

36 Photos

68 First Street, Dufferin, ON , MLS #W13632570 , Image - 1

Unit-24, 68 First Street Orangeville, Dufferin, ON MLS® W13632570

Residential Freehold (Att/Row/Townhouse)

$619900.0

3 Beds
3 Baths
1500-2000 sq-ft

End-Unit Freehold Townhome | 3-Storey | Walkable Orangeville Location. Welcome to 68 First Street, Unit 24, a 2023-built, 3-bed, 3-bath end-unit freeh

Open House : Sun Sep 27, 11:00 AM to 01:00 PM

43 Photos

7 Third Avenue, Dufferin, ON , MLS #W13798324 , Image - 1

7 Third Avenue Orangeville, Dufferin, ON MLS® W13798324

Residential Freehold (Detached)

$875000.0

2 Beds
2 Baths
1500-2000 sq-ft

Enjoy exceptional in-town living, timeless character and thoughtful updates in this charming century bungalow. Located on a beautiful, mature tree-lin

44 Photos

70 Hunter Road, Dufferin, ON , MLS #W13814722 , Image - 1

70 Hunter Road Orangeville, Dufferin, ON MLS® W13814722

Residential Freehold (Detached)

$929000.0

4 +2 Beds
4 Baths
2000-2500 sq-ft

WELCOME TO THIS WELL-MAINTAINED DETACHED HOME nestled in a quiet, family-friendly neighbourhood in ORANGEVILLE. Offering approximately 2,001 SQ FT ABO

50 Photos

77 Zina Street, Dufferin, ON , MLS #W13207758 , Image - 1

77 Zina Street Orangeville, Dufferin, ON MLS® W13207758

Residential Freehold (Detached)

$749900.0

Price drop by 10.7%

3 Beds
1 Baths
1100-1500 sq-ft

Welcome to 77 Zina Street, a charming bungalow located on one of Orangeville's most sought-after streets, just steps from downtown shops, restaurants,

49 Photos

108 Glengarry Road, Dufferin, ON , MLS #W13828208 , Image - 1

108 Glengarry Road Orangeville, Dufferin, ON MLS® W13828208

Residential Freehold (Detached)

$799900.0

3 Beds
3 Baths
1100-1500 sq-ft

Welcome to 108 Glengarry Road - this beautiful home is situated in an desirable location, just steps away from the recreation centre, vibrant shops, l

49 Photos

267 Montgomery Boulevard, Dufferin, ON , MLS #W13817980 , Image - 1

267 Montgomery Boulevard Orangeville, Dufferin, ON MLS® W13817980

Residential Freehold (Detached)

$775000.0

3 Beds
2 Baths
1100-1500 sq-ft

Fantastic 4-Level Backsplit on a 37.99 x 95 Feet Premium Corner Lot located in the highly desirable Montgomery Village neighbourhood.This beautiful &

34 Photos

68 First Street, Dufferin, ON , MLS #W13813304 , Image - 1

Unit-35, 68 First Street Orangeville, Dufferin, ON MLS® W13813304

Residential Freehold (Att/Row/Townhouse)

$669000.0

3 Beds
3 Baths
1500-2000 sq-ft

Built in 2023 and immaculately kept, Unit 35 at First Street Towns is a bright, upgraded 3-bedroom, 3-bathroom corner unit townhome, that feels like

Open House : Sun Sep 27, 12:30 PM to 02:30 PM

45 Photos

7 Henry Street, Dufferin, ON , MLS #W13824932 , Image - 1

7 Henry Street Orangeville, Dufferin, ON MLS® W13824932

Residential Freehold (Detached)

$1077000.0

3 Beds
3 Baths
1500-2000 sq-ft

Welcome to 7 Henry Street, a beautifully crafted newly built, two storey home blending refined design with thoughtful everyday functionality. Built wi

12 Photos

63 First Street, Dufferin, ON , MLS #W13825606 , Image - 1

Unit-A2, 63 First Street Orangeville, Dufferin, ON MLS® W13825606

Residential Condo & Other (Condo Apartment)

$229000.0

1 Beds
1 Baths
0-499 sq-ft

REDUCED PRICE: Welcome to this charming 1-bedroom condo that combines character with great potential. Featuring laminate floors and large windows that

42 Photos

68 First Street, Dufferin, ON , MLS #W13671628 , Image - 1

Unit-33, 68 First Street Orangeville, Dufferin, ON MLS® W13671628

Residential Freehold (Att/Row/Townhouse)

$499000.0

3 Beds
3 Baths
1500-2000 sq-ft

Beautiful 3-bedroom townhouse located in desirable area of Orangeville. This well maintained home features impressive 9 ft ceilings on the main floor,

39 Photos

72 Victor Large Way, Dufferin, ON , MLS #W13753770 , Image - 1

72 Victor Large Way Orangeville, Dufferin, ON MLS® W13753770

Residential Freehold (Att/Row/Townhouse)

$599999.0

3 Beds
3 Baths
1100-1500 sq-ft

Absolutely immaculate and truly move-in ready, this beautifully maintained 3-bedroom, 3-bathroom home showcases quality and attention to detail throug

Open House : Sun Sep 27, 01:00 PM to 03:00 PM

13 Photos

105 Spencer Avenue, Dufferin, ON , MLS #W13482610 , Image - 1

Unit-304, 105 Spencer Avenue Orangeville, Dufferin, ON MLS® W13482610

Residential Condo & Other (Condo Apartment)

$513130.0

Price drop by 14.3%

1 Beds
1 Baths
600-699 sq-ft

Location, Location, Location! Welcome to Westview Condos in a highly sought-after location. This spacious 1-bedroom, 1-bathroom condo includes 1 parki

50 Photos

119 Oak Ridge Drive, Dufferin, ON , MLS #W13778264 , Image - 1

119 Oak Ridge Drive Orangeville, Dufferin, ON MLS® W13778264

Residential Freehold (Detached)

$1175000.0

4 Beds
3 Baths
2000-2500 sq-ft

*Open House this Sunday, Sept 27th from 12-2pm* This Is The One You've Been Waiting For! Welcome To A Home That Truly Checks All The Boxes, Space, Sty

Open House : Sun Sep 27, 11:00 AM to 01:00 PM

27 Photos

139 Town Line, Dufferin, ON , MLS #W13821384 , Image - 1

139 Town Line Orangeville, Dufferin, ON MLS® W13821384

Residential Freehold (Semi-Detached )

$749000.0

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

Offered for the very first time. Homes like this don't come up often on Town line, and this one never has - until now. It started out in 1966 and has

Open House : Sun Sep 27, 12:00 PM to 02:00 PM

24 Photos

12 Maude Court, Dufferin, ON , MLS #W13817252 , Image - 1

12 Maude Court Orangeville, Dufferin, ON MLS® W13817252

Residential Freehold (Detached)

$1039900.0

4 Beds
3 Baths
2000-2500 sq-ft

Welcome to 12 Maude Court, an exceptional Karleton model on a quiet cul de sac in Orangeville's popular Settlers Creek neighbourhood. This spacious 4-

Open House : Sun Sep 27, 01:00 PM to 03:00 PM

50 Photos

16 Brenda Boulevard, Dufferin, ON , MLS #W13590678 , Image - 1

16 Brenda Boulevard Orangeville, Dufferin, ON MLS® W13590678

Residential Freehold (Detached)

$724000.0

Price drop by 3.3%

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

Welcome to 16 Brenda Boulevard - a beautifully maintained bungalow that checks every box for first-time buyers and savvy investors alike. This move-in

44 Photos

105 Spencer Avenue, Dufferin, ON , MLS #W13822598 , Image - 1

Unit-210, 105 Spencer Avenue Orangeville, Dufferin, ON MLS® W13822598

Residential Condo & Other (Condo Apartment)

$779900.0

2 Beds
2 Baths
1000-1199 sq-ft

Nestled alongside a spectacular hardwood forest is this pristine, corner condominium unit that offers you a tranquil sanctuary with expansive views an

39 Photos

309 Marshall Crescent, Dufferin, ON , MLS #W13822258 , Image - 1

309 Marshall Crescent Orangeville, Dufferin, ON MLS® W13822258

Residential Freehold (Detached)

$825500.0

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

Welcome to this beautifully appointed all-brick detached home, ideally situated in a desirable family friendly neighborhood and offering a thoughtfull

Open House : Sun Oct 04, 01:00 PM to 03:00 PM

38 Photos

30 Dawson Road, Dufferin, ON , MLS #W13821230 , Image - 1

30 Dawson Road Orangeville, Dufferin, ON MLS® W13821230

Residential Freehold (Att/Row/Townhouse)

$609000.0

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

Welcome to 30 Dawson Road - a 3+2 - bed, 3-bath FREEHOLD NO FEES AT ALL townhome in the heart of Orangeville! Gleaming hardwood floors, spacious princ

Open House : Sat Oct 03, 01:00 PM to 03:00 PM

50 Photos

12 York Street, Dufferin, ON , MLS #W13715960 , Image - 1

12 York Street Orangeville, Dufferin, ON MLS® W13715960

Residential Freehold (Detached)

$2350000.0

3 +1 Beds
3 Baths
2500-3000 sq-ft

Set on one of the most coveted streets in Orangeville, this rarely offered 3+1 bedroom Victorian residence combines timeless charm w modern luxury. Fu

35 Photos

50 Margaret Street, Dufferin, ON , MLS #W13820860 , Image - 1

50 Margaret Street Orangeville, Dufferin, ON MLS® W13820860

Residential Freehold (Detached)

$699000.0

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

Welcome to 50 Margaret Street, a surprisingly spacious 3 +1 bedroom, 4 bath detached home tucked into a mature, tree-lined neighbourhood just minutes

40 Photos

117 Oak Ridge Drive, Dufferin, ON , MLS #W13805938 , Image - 1

117 Oak Ridge Drive Orangeville, Dufferin, ON MLS® W13805938

Residential Freehold (Detached)

$1059900.0

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

Welcome to this 4+1 bedroom, fully finished home designed for practical family living. Featuring bright, open-to-above ceilings and great layout flow,

Open House : Sun Sep 27, 01:00 PM to 03:00 PM

44 Photos

260 Lisa Marie Drive, Dufferin, ON , MLS #W13649724 , Image - 1

260 Lisa Marie Drive Orangeville, Dufferin, ON MLS® W13649724

Residential Freehold (Detached)

$959999.0

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

Gorgeous Family Home that Backs onto Greenbelt in Established Orangeville Neighbourhood. Numerous Upgrades including Lower Level In Law Suite with Ful

49 Photos

39 Amelia Street, Dufferin, ON , MLS #W13701492 , Image - 1

39 Amelia Street Orangeville, Dufferin, ON MLS® W13701492

Residential Freehold (Detached)

$875000.0

4 Beds
4 Baths
1500-2000 sq-ft

Spacious and beautifully updated 4-bed, 4-bath two-storey home on a desirable corner lot in Orangeville. A charming covered front porch and double-doo

47 Photos

35 Cameron Court, Dufferin, ON , MLS #W13766354 , Image - 1

35 Cameron Court Orangeville, Dufferin, ON MLS® W13766354

Residential Freehold (Detached)

$829999.0

4 Beds
4 Baths
1500-2000 sq-ft

Exceptionally Maintained 4-Bed, 3-Bath Home Offering Approx. 2,500 sq. ft. of Thoughtfully Designed Living Space in One of Orangeville's Most Desirabl

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