Neighborhood Guide · Dane County
Oregon sits just south of Madison and Fitchburg, where the suburbs give way to farm fields and rolling hills. It has a Main Street with a brewery, a coffeehouse, and a breakfast spot that serves breakfast all day, a summer festival with a carnival and fireworks, and the Badger State Trail running just west of town.
Our team has helped buyers, sellers, and relocating families across Dane County since 2012, and our founder, Cait Berry, is a sixth-generation Madisonian. Many of our Oregon buyers come here after realizing they want more space and a small-town pace without being far from Madison. This guide is what we walk our own clients through: where each part of town sits, what drives home values, what it costs to own here, and how the year actually feels. If you only have a minute, jump to the section you need.
11,179
Residents (2020 Census)
40
Miles of Badger State Trail
$515,000
Median single-family sale
7
Median days on market
Market figures: Village of Oregon single-family sales, September 2026, South Central Wisconsin MLS.
The honest version
We would rather you find the right town than the wrong house. Here is how we talk about Oregon with our own clients.
Getting around
US Highway 14 runs along the north and east sides of the village toward Fitchburg and the Beltline, and Wisconsin Highway 138 heads southeast toward Stoughton. Here is what typical drives look like outside of rush hour.
One thing we always mention: Highway 14 between Oregon and the Beltline gets busy at rush hour, and your side of the village changes how quickly you can get onto it. If you will be commuting at peak times, we are happy to map your actual route from any home you are considering.
The market
You will find older homes near downtown, established neighborhoods from the 1970s through the 2000s, newer construction on the edges of the village, golf course homes in Bergamont, and acreage in the surrounding towns. In our experience, home values here are shaped most by:
In other words, two homes with the same square footage can sell for very different prices a mile apart. When we price a home or write an offer here, we pull the sales from that specific part of town, not the village-wide median.
Most sales landed between $400,000 and $699,999.
The 2026 median so far is about 12% higher than 2025's.
In other words, one month's median can bounce around with only a dozen sales, but the bigger picture is clear: Oregon prices are up for the year, and well-priced homes are still selling in about a week. Year-over-year changes compare September 2026 with September 2025.
Source: South Central Wisconsin MLS, Village of Oregon, report pulled October 20, 2026.
Compare the areas
Oregon gets talked about by location and feel more than subdivision names. Start with what matters most to you, then read the notes below.
Downtown Oregon
The Netherwood Knoll and Prairie View areas
Bergamont
The edges of the village and the surrounding towns
The ways buyers usually describe where an Oregon home sits.
The walkable heart of the village, close to local restaurants, the library, Kiser Firemen's Park, and community events.
If someone says they live near Main Street or the library, this is usually what they mean.
Neighborhoods around Netherwood Knoll Elementary, with Keller Alpine Meadows Park, the Highlands of Netherwood Park, and the Oregon Rotary Bike Trail nearby.
Quieter and more residential, with newer homes and wider streets, near Prairie View Elementary.
A golf course neighborhood with more open space and larger homes, and a slower pace.
Homes on the edges of the village and acreage in the Towns of Oregon, Dunn, and Rutland, for buyers who want Oregon but not right in town.
Town properties have different taxes and services, and many use private wells and septic.
Do your research
Oregon is served by the Oregon School District, which includes Netherwood Knoll, Prairie View, Brooklyn, and Forest Edge elementary schools, Rome Corners Intermediate School, Oregon Middle School, and Oregon High School, along with a 4K program. The district also runs the community pool and splash pad.
School assignments can change. Always confirm by address.
Schools are a big reason many families choose Oregon, and locals tend to think about them in terms of daily routines: walkability, drop-off, and how the school day fits into family life. What makes a school the right fit is personal, so we encourage every buyer to do their own research. The district's school information, the Wisconsin DPI school report cards, and an in-person visit are great places to start. When you are serious about a home, we will confirm the school assignment for that exact address before you write an offer.
Beyond the price
Purchase price is only part of the picture. These are the numbers we walk through with buyers before they fall in love with a house.
When the village adopted its 2026 budget, the Oregon Observer reported a village rate of $4.67 per $1,000 of assessed value, down 12.6% from the year before. The school district, Dane County, and Madison College are added on top, and town properties are taxed differently, so we pull the actual tax bill for every home you consider.
Alliant Energy lists Oregon in its electric and gas service area. Homes in the surrounding towns may have a different provider, so check the listing details or ask us.
Many homes in the towns around Oregon use private wells and septic systems, so we build those inspections into the timeline.
Some newer neighborhoods have an HOA or covenants, and many older ones do not. Dues and rules vary, so we request the documents early.
Figures are a starting point, not a quote. Tax rates change every year and depend on the exact parcel.
A year in oregon
The best way to understand a town is to know what everyone is doing each season. Here is how a year in Oregon tends to go.
Winter
The walking path at Keller Alpine Meadows Park and the trails at Lerner Conservation Park stay busy on clear days, and the Oregon Public Library is a favorite stop on cold afternoons.
Spring
The Badger State Trail fills back up with cyclists, and the ball diamonds and pickleball courts at Jaycee Community Park get busy again.
Summer
Oregon Summer Fest takes over Kiser Firemen's Park in June with a carnival, a parade, sports tournaments, and fireworks, and families spend afternoons at the community pool and splash pad.
Fall
Friday nights belong to high school football, Badger fans catch a game day shuttle from Headquarters, and the farm fields around town turn gold.
Where locals go
These are the places we send clients when they ask what they would actually do on a Saturday here.
A 40-mile trail from Madison to the Illinois border that passes just west of Oregon.
The home of Oregon Summer Fest.
More than 100 acres with a two-mile walking path along Alpine Parkway.
Sixty-five acres of conservancy land and trails.
Pickleball, ball diamonds, and a concession stand.
A Dane County park with a dog park.
A bike path from Netherwood Road to Fish Hatchery Road Park.
Story times, events, and a good book on Alpine Parkway.
A craft brewery with Mesoamerican food, brunch, and live music.
Breakfast all day on Main Street, plus a Friday fish fry.
The Main Street coffee stop.
A sports bar with 32 taps, golf simulators, and sand volleyball.
Pizza and pasta on Main Street, for dine-in or carryout.
A Main Street tavern with burgers and lunch specials.
Relocating to Oregon
A lot of our Oregon buyers are moving to the Madison area for work and want a small town with good schools and more space. You don't know what you don't know about a new town, and that is exactly where a local team earns its keep. Here is how we usually do it.
01
We start with your commute, your budget, your must-haves, and your timeline, and talk about how Oregon compares to Fitchburg, Verona, and Stoughton.
02
We narrow the area down to two or three neighborhoods that fit and tell you why, including the tradeoffs.
03
If you cannot be here, we tour homes live on video, drive the street at night and on a weekday morning, and confirm the school assignment for the exact address.
04
When you do fly in, the weekend is mapped out so you see the right homes and the neighborhoods around them.
05
We handle inspection, appraisal, and the local details from here, and keep you updated every step of the way.
Already in Oregon?
If you love the village but have outgrown the house, the biggest question is usually whether to buy first or sell first. The answer depends on your equity, your financing, and how much inventory is available in the neighborhood you want next. We will lay out both paths with real numbers for your home, then help you decide which order makes sense.
Read our seller's guideRead our buyer's guide
Questions we hear
For a lot of buyers, yes. Oregon has a small-town Main Street, its own school district, parks and trails, a busy summer festival, and an easy drive to Fitchburg, Verona, and Madison. It is growing, so expect new construction on the edges and traffic on Highway 14 at rush hour.
Oregon is just south of Madison and Fitchburg along Highway 14. Downtown Madison is about 20 to 25 minutes away outside of rush hour, Fitchburg is about 10 to 15 minutes, and Epic is about 20 minutes.
Oregon is in the Oregon School District, with Netherwood Knoll, Prairie View, Brooklyn, and Forest Edge elementary schools, Rome Corners Intermediate, Oregon Middle School, and Oregon High School. Always confirm the school assignment by address.
The village's 2026 budget set a village rate of $4.67 per $1,000 of assessed value, down 12.6% from the year before, according to the Oregon Observer. School, county, and Madison College taxes are added on top, so we pull the actual bill for every home you consider.
In September 2026, the median single-family sale in the Village of Oregon was $515,000, and homes sold in a median of 7 days. The 2026 median so far is $549,900, about 12% higher than 2025's.
Summer Fest is held each June at Kiser Firemen's Park, with a carnival, a parade, sports tournaments, and fireworks.
Yes. The Badger State Trail runs about 40 miles from Madison to the Illinois border and passes just west of Oregon, with a trailhead near Purcell Road. A state trail pass is required for cyclists 16 and older.
Talk to the Insiders Realty team
Whether you are moving from across the country or across town, we will help you narrow down the neighborhoods, understand the real costs, and make a plan. Grab 15 minutes with us this week.
Schedule coffee or a Zoom chatGet the relocation guide
11,547 people live in Oregon, WI, where the median age is 39.6 and the average individual income is $49,569. Data provided by the U.S. Census Bureau.
Total Population
Median Age
Population Density Population Density This is the number of people per square mile in a neighborhood.
Average individual Income
