01Victorian Main Street
Broadway
A genuinely intact Victorian commercial street with independent shops, the Tree Sculpture Tour carved from standing stumps, and a farmers' market that runs from spring through autumn.
✦ Dufferin County · Community Guide
ORANGEVILLEthe headwaters town.
Broadway & the Orangeville main street
Orangeville sits at the top of the Credit River watershed, high enough that it gets real winters and real snow. A Victorian main street lined with tree sculptures, a theatre company with a national reputation, and detached family housing at a price the rest of the GTA stopped offering years ago.
- Average price
- $750K
- Typical range
- $450K – $2.5M+
- Region
- Dufferin County, Ontario
750K
Average price
All property types
30K
Residents
Dufferin County seat
45min
To Pearson
Via Highway 10
425m
Elevation
Snowbelt country
The case for Orangeville
Why live here.
Five things that keep bringing buyers back to Orangeville.
02Professional Company
Theatre Orangeville
A professional theatre company producing a full season of Canadian work in the old town hall opera house — a cultural anchor most towns of thirty thousand simply do not have.
03Credit · Grand · Nottawasaga
Headwaters Country
Three major river systems begin in these hills. Island Lake, the Bruce Trail, Hockley Valley and Mono Cliffs are all within fifteen minutes of the town limits.
04Family Housing Stock
Detached, Attainably
Orangeville is where GTA families go when they want a detached house with a real yard and a garage without borrowing at the very edge of what they can carry.
05Snowbelt Elevation
Four Real Seasons
At 425 metres, Orangeville gets more snow than anywhere else in commuting distance — which means Hockley Valley and Mansfield are skiing while the lakeshore is raining.
Local knowledge
Orangeville pocket by pocket.
Every neighbourhood trades differently. Open any one to see what is on the market there right now.
01Downtown & Broadway
Century homes & apartments
02Montgomery Village
Detached & freehold towns
03Rolling Hills
Detached & bungalows
04West End
Detached, semis & towns
05North Orangeville
New detached & towns
06Hockley Valley & Mono
Country estates & acreage
07Mono Cliffs & the Escarpment
Rural properties & hobby farms
08Amaranth & Rural Dufferin
Farmland & country homes
Live Orangeville market
On the market now.
For Sale
$1,840,000
5 BD4 BA
18805 WILLOGHBY ROAD, Caledon, Ontario, L7K1V7
MLS® W12422743
For Sale
$1,311,990
4 BD4 BA
LOT 46 - 52 MEYER DRIVE, Orangeville, Ontario, L9W4S2
MLS® W12490892
For Sale
$5,995,000
94 SQFT
21120 KENNEDY ROAD, Caledon, Ontario, L7K1Y5
MLS® W12661642
For Sale
$899,900
3 BD2 BA
2901 CHARLESTON SIDE ROAD, Caledon (Caledon Village), Ontario, L0N1C0
MLS® W12679666
For Sale
$1,499,000
5 BD5 BA
8 MITCHELL CRESCENT, Mono, Ontario, L9W6W6
MLS® X12721692
For Sale
$557,513
3 BD3 BA
8 FAULKNER COURT, Kawartha Lakes (Lindsay), Ontario, K9V0P8
MLS® X12812434
Culture, sport & the outdoors
Life in Orangeville.
What a weekend looks like once the paperwork is done and the keys are yours.
01Main street & town life
Broadway, the Tree Sculptures & the Market
An intact Victorian commercial street with independent retail, a self-guided tour of chainsaw-carved tree sculptures, and a market that runs from May into autumn.
02Lake, trails & paddling
Island Lake Conservation Area
A reservoir at the town's edge with an eight-kilometre loop trail, a floating boardwalk, canoe rentals and fishing minutes from downtown.
03Skiing, golf & hiking
Hockley Valley & Mono Cliffs
A resort valley with skiing, golf and a spa fifteen minutes east, and a provincial park of escarpment cliffs and crevices just north.
04Culture & performance
Theatre Orangeville & the Arts
A professional theatre company in the restored opera house, plus the Dufferin County Museum and a well-established studio tour each autumn.
05Dining & cafés
Broadway's Independent Kitchens
A Victorian main street where the restaurants, cafés and bakeries are still independently owned, plus a farmers' market that runs from May into autumn and resort dining fifteen minutes east at Hockley Valley.
06Transit & commute
Highway 10 & No Rail Line
Highway 10 runs south to Brampton in about half an hour and Pearson in about forty-five minutes. There is no GO rail station — which is exactly why the housing costs what it does, and why hybrid schedules suit this town best.
Everyday essentials
What's around the corner.
The Orangeville amenities that decide how a street actually lives — not just how it shows.
01·
Dining & cafés
A main street where the kitchens are still independently owned.
Broadway
independent restaurants, cafés and bakeries through the Victorian core
Orangeville Farmers' Market
Saturday market running from May into the autumn
Hockley Valley Resort
resort dining, spa and a working kitchen garden fifteen minutes east
First Street & Riddell corridors
the everyday casual dining and grocery-anchored plazas
02·
Shopping & retail
A heritage main street backed by full-service retail on the edges.
Downtown Orangeville BIA
independent shops, galleries and services along Broadway and Mill
Orangeville Mall & First Street
grocery, pharmacy and everyday retail
Riddell Road retail
big-box, home improvement and warehouse retail on the south edge
Dufferin County studio tour
an annual autumn tour of working artists' studios across the hills
03·
Transit & commute
Highway 10 south. No GO rail — that trade-off is priced into the housing.
Highway 10
the main route south; Brampton in about thirty minutes
Toronto Pearson
roughly forty-five minutes down Highway 10 and the 410
Orangeville Transit
local bus network covering the town and connecting to GO bus service
Highway 9 & Airport Road
east–west routes toward Highway 400 and the Caledon hills
04·
Sport & recreation
Arenas and pools in town, skiing and golf fifteen minutes out.
Alder Street Recreation Centre
twin-pad arena, pool and fitness facility
Tony Rose Memorial Sports Centre
the town's second arena and community sport hub
Hockley Valley Resort
downhill skiing, golf and spa in the valley east of town
Mono Cliffs & Mansfield
hiking, mountain biking and Nordic skiing in the hills north
05·
Parks & trails
Headwaters country — three river systems begin within a short drive.
Island Lake Conservation Area
an 8 km loop trail, floating boardwalk, canoe rentals and fishing
Mono Cliffs Provincial Park
escarpment cliffs, crevices and lookouts just north of town
Bruce Trail — Dufferin Hi-Land section
escarpment hiking through the hardwood ridges
Tree Sculpture Tour
a self-guided walk of chainsaw-carved sculptures through the town
06·
Health & essentials
The county's hospital, library and OPP headquarters are all in town.
Headwaters Health Care Centre
the county hospital, with a full emergency department
Orangeville Public Library
main branch on Mill Street with community programming
Dufferin County administration
county seat services, land registry and social services in town
Grocery & pharmacy corridors
full-service grocers along First Street, Broadway and Riddell Road
Want to know what sits within a five-minute walk of a specific address? Ask us — we run that check on every property before our clients see it.
Browse Orangeville homesEducation
Schools & catchments.
In Orangeville, catchment moves price as much as square footage does. Boundaries are reviewed periodically — confirm the current one before you firm up.
01
Public Schools
Upper Grand District School Board
Orangeville District Secondary School
The Town's Original
A long-established secondary school with strong music and athletics traditions and a full academic course list.
Westside Secondary School
Modern West-End Campus
The town's newer secondary school, with modern facilities, French Immersion and specialist high skills major pathways.
Island Lake & Montgomery Village PS
Neighbourhood Elementary
Walkable elementary schools anchoring the north and east family neighbourhoods, both with trail and park access.
02
Catholic Schools
Dufferin-Peel Catholic District School Board
Robert F. Hall Catholic Secondary School
Regional Catholic Secondary
Serving Orangeville and Caledon families from a campus in Caledon East, with established arts, athletics and co-op programming.
St. Peter & St. Andrew Catholic Elementary
In-Town Elementary
Orangeville's Catholic elementary schools, feeding into the regional secondary pathway.
03
Post-Secondary Access
Commutable campuses
University of Guelph
45 Minutes Southwest
A leading agricultural, veterinary and life sciences university, close enough that Orangeville students routinely commute.
Humber & Sheridan Colleges
South Along Highway 10
Humber's North Campus and Sheridan's Davis Campus in Brampton are both reachable in under an hour down Highway 10.
Straight answers
Orangeville, asked & answered.
The questions that come up on almost every first call.
It depends on your week. Pearson is about forty-five minutes down Highway 10 and Brampton about half an hour, but there is no GO rail station — so a daily downtown commute is a real commitment. For hybrid schedules it works well, and the price difference is substantial.
The town averages around $750K, which in practice buys a detached family home with a garage and a yard in most neighbourhoods — the kind of stock that costs well over a million an hour southeast.
Genuine. At 425 metres of elevation the town sits in a snowbelt and gets considerably more snow than the lakeshore. That is a downside on the driveway and an upside fifteen minutes east at Hockley Valley.
More than the size suggests — a professional theatre company, a Victorian main street with independent retail, the Tree Sculpture Tour, Island Lake Conservation Area, and skiing, golf and hiking all within fifteen minutes.
Montgomery Village and the north end near Island Lake are the two we point families toward most — both pair walkable schools with parks and direct trail access. The west end carries the most attainable entry pricing.
The People
Your Orangeville team.
Markjensen.
Broker of Record
With over 15 years in the Oakville and Burlington markets, Mark has built his reputation on honest guidance and exceptional results. He specialises in move-up buyers, luxury properties, and seller strategy — personally closing 400+ transactions across Halton Region.
TEL(289) 815-2822MAILmark@thejensenteam.ca
Leahjensen.
Realtor®
Leah brings warmth and market depth to every buyer journey. Known for her patience and deep neighbourhood knowledge across Oakville, Mississauga and Burlington, she ensures her clients find not just a house — but the right home.
TEL(647) 424-3576MAILleah@thejensenteam.ca✦ Buying in Orangeville
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