$534,310Average Value$247Average Price per Sq Ft33Homes For Sale
Suburban comforts with a small-town feel
Surrounded by miles of farmland and featuring a charming historic Main Street, Oregon provides a small-town atmosphere with the amenities and conveniences of modern suburbia. Located 11 miles south of downtown Madison, Oregon was originally settled in the 1840s and continues to expand outward towards the surrounding farmland. “All of Dane County has been growing, but Oregon is a great location because people can commute into Madison in 20 minutes and it’s also close to Stoughton,” says Ruth Wangerin, a broker associate with Stark Company Realtors who has sold homes across the Madison area. “It’s where people who work in the city can go to get away.” With a handful of restaurants and a grocery store, Oregon is mainly comprised of an array new and established homes that fan out from its quaint town center.
Welcome to Oregon, where residents like to stay active year-round.
Downtown Oregon is full of historic charm, including in its retail district.
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Established homes near Main Street, with new subdivisions growing
Due to the area’s continued expansion, homes in Oregon encompass a wide range of build years and styles. Near the town’s historic Main Street, ranch-style homes and large Foursquares line the streets in tidy rows, surrounded by trees and framed by sidewalks. Further out, new subdivisions have cropped up with contemporary one- and two-story homes that sit on spacious half-acre lots with attached two-car garages. Some of these homes can cost upwards of $800,000, though there are also two-bedroom houses available in the lower $200,000s range, and the median for the area is close to $400,000. Homebuyers who can’t find a house that catches their eye can also build the custom home of their dreams, with plenty of available lots to choose from.
19th century Victorian homes can be found in on Main Street in Oregon, Wisconsin.
The Bergamot development in Oregon is one of the higher-end areas, with access to a golf course.
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Excellent public education in the Oregon School District
Families can send their children to public schools in the Oregon School District. Kids might start out at Prairie View Elementary through the fourth grade before heading over to Rome Corners Intermediate for grades five and six; both schools receive an A-minus rating from Niche. Oregon Middle, which scores a B, prepares seventh and eighth graders to attend Oregon High. The high school also earns an A-minus and boasts a plethora of extracurriculars to boost its students’ resumes, from model U.N. and mock trial to bowling club and ski club.
Local teenaged students can attend Oregon Middle School.
Parents in Oregon can send their little ones to Prairie View Elementary School.
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Commute into Downtown Madison in 20 minutes
Bordered to the east by US Highway 14 towards Highway 18, Oregon is just over 10 miles or a roughly 20-minute drive from Downtown Madison. With limited biking infrastructure and walkability, residents of Oregon are largely car dependent, but can get to their daily needs easily within town and commute into Madison for everything else, be it big-box shopping or UW Health’s University Hospital. When faraway destinations beckon, residents can take to the skies from Dane County Regional Airport, located approximately 30 minutes to the north.
Travel to the state capitol from Oregon is a breeze when you use Highway 18.
Oregon rates low on walkability, so most residents rely on cars.
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Grab a bite at local restaurants along historic Main Street
Strolling down Main Street towards the heart of town, historic brick buildings with ornate facades spring up alongside the area’s 19th-century water tower, nicknamed “the tin man” by locals. This charming town center is populated by local businesses where owners know their patrons by name. Firefly Coffeehouse is the place to go to grab a quick coffee or relax in a comfortable lounge chair with a freshly baked pastry. There are plenty of spots to have a bite, such as Sonny’s Kitchen, a homestyle diner with a friendly feel. For after-dinner drinks, the Wine Reserve offers a chic spot to catch up over wine and a cheeseboard. For groceries and other daily goods, folks head north to the local Hy-Vee grocery store and Walgreens, open seven days a week.
Sonny's Kitchen is always busy on Sunday mornings, serving breakfast with a smile.
The Pizza Pit in Oregon has been around for over 30 years.
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Parks for nature lovers, sports enthusiasts and four-legged friends
Oregon offers plenty of ways to get outdoors between its numerous outdoor parks. For a leisurely stroll past blooming wildflowers and around tranquil ponds, residents walk the 2-mile paved path at Lerner Conservation Park. Sports enthusiasts can be found at Kiser Fireman’s Park using its baseball diamonds, tennis courts, soccer fields or skate park. Golfers can book a tee time at the Legend at Bergamont, an 18-hole golf course designed by US Open Champion Andy North. Additionally, Oregon residents can bring their furry friends to Jon Blanchard Dog Park, where they can enjoy some off-leash exercise in the open air.
Jon Blanchard Dog Park in Oregon has two main fenced-in areas for pet owners to enjoy.
For birders in Oregon, Lerner Conservation Park has geese, sandhill cranes and more.
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Written By
Tina Davis
Video By
Patrick Johnson
Interested in learning more about homes in this area?
Reach out to
Lena Oberwetter,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
On average, homes in Oregon, WI sell after 45 days on the market compared to the national average of 55 days. The median sale price for homes in Oregon, WI over the last 12 months is $494,900, up 5% from the median home sale price over the previous 12 months.
Move-in ready and waiting for you! This beautifully maintained 4-bedroom, 3.5-bath home has been freshly painted and is ready to enjoy from day one. The bright, inviting main level offers comfortable living spaces and easy access to the deck—perfect for grilling, entertaining, or relaxing outdoors. Upstairs, you’ll find four spacious bedrooms, including a private primary suite with its own bath
Rare opportunity with approximately 12 acres in Dane County! 2 tax parcels for sale 0510-191-9500-6 - 9.736 acres and 0510-202-9230-9 - 2.10 acres - both parcels to be sold together. The property includes eligibility for one potential land division/development right, which may be used on the property or transferred to another qualifying property, subject to all town and Dane County requirements
This beautifully updated home offers a fully remodeled main level with a modern kitchen featuring custom granite countertops, hickory cabinets, a stylish full bath with tiled shower, and a welcoming entry porch with cathedral ceiling. A expansive 33'6"x22'6" garage fully insulated and sheet rocked and painted. The garage and second floor were added in 2015, 2016 and includes two bedrooms and a
Opportunity awaits on this 5 acre property just south of Madison in the Town of Oregon. Several outbuildings on the property including the original barn, 3 car detached garage and two pole sheds provide multiple possibilities for storage, hobbies or animals. Includes a Foursquare farm house. House and some outbuildings are in need of some TLC. Property is also listed as Single Family. Seller is
Thoughtfully updated condo that truly lives like a single-family home in a welcoming Oregon community! Condo Fees are $200/month. Enjoy a private entry and convenient 2-car attached garage, along with vaulted ceilings and abundant natural light throughout the inviting main living space. Upgraded lighting, new flooring, and an enhanced kitchen with added pantry cabinetry and butcher block counter
Better than new, this 2023 Oregon ranch has been thoughtfully finished and upgraded since the day it was built. Step inside to an open, airy main level with wood floors that flow throughout and a great room made for gathering. The kitchen is a standout, featuring a large island, pantry, and quartz countertops, all opening naturally into the living and dining spaces. The primary suite is a true
Beautiful ranch home offering the perfect blend of comfort, convenience, and outdoor enjoyment. Stunning hardwood floors welcome you inside, while the remodeled kitchen is ready for everyday living and entertaining alike. Unwind in the spa-like bathroom, designed to feel like your own private retreat. Outside, enjoy a generous lot featuring cherry trees, apple trees, plum tree, raspberry bush,
Tucked away in Autumn Ridge, this two-story home exudes elegance and charm. The open main level flows from a chef-ready kitchen with granite counters and an island into a stunning dining room crowned by a three-tier French vintage chandelier, all set in a five-window, cathedral-ceiling sunroom that spills onto the patio and into the fully fenced backyard. Cozy up by the brick gas fireplace, pour
A rare opportunity to secure 37.5 acres of productive tillable ground just outside Oregon, WI in the Town of Rutland. This high, rolling acreage offers excellent drainage, strong yield potential and easy access off County Rd A with quick connection to HWY 14. Its proximity to town makes it an exceptional piece of income-producing farmland. Ideal for operators looking to expand their tillable
Under Construction. Get ready to fall in love with your brand-new home on Autumn Blaze Court. Arriving in December 2026 is a stunning new construction by Alterra Design Homes. It offers the perfect balance of peace and proximity. Nestled on a scenic hill overlooking the Village of Oregon, you're just 15 minutes from the heart of Madison but worlds away from the noise.
Prime 3.2-acre development opportunity in the Village of Oregon, WI! This PD (Planned Development) zoned parcel offers flexibility with approved site plans that have included multifamily, duplex condos and a wide range of permitted uses. Ideal for developers and investors seeking a ready-to-advance project in a growing community. Utilities are available at the lot lines, providing a strong head
WORK FROM HOME? NO PROBLEM HERE. With its spacious flex room, The Costello offers up the sanctuary you need to balance business with pleasure. Skip the fast food and prep your own gourmet lunch, because why wouldn’t you when you have a lovely kitchen pantry to hold all your meticulously organized spices and grains. When you’re ready to call it a day, retreat and recharge in your private oasis
Townhomes with an open floor plan in scenic Oregon, WI. With a world-class golf course, exclusive clubhouse and swimming pool right down the road, you're just minutes from a lifestyle of luxury.
Nestled in the Village of Oregon, the Prairie Brook Apartments are in a great location for families, young professionals, retirees and more! There are many local parks nearby and the Jon Blanchard Dog Park is just minutes from your door. This new construction complex features many desirable amenities including on-site office, fitness center, community room, gazebo, grilling area and more. Each
Available now! These thoughtfully designed apartments have a lot to offer including key fob entry, full kitchens with stove, refrigerator, dishwasher, and microwave, private balcony, full bathrooms, and in-unit washer and dryer. No need to worry about parking, as off-street parking is available for your convenience.
The Commons of Foxboro – Thoughtful Living in OregonWelcome to The Commons of Foxboro, a well-appointed apartment community in Oregon offering comfortable, connected living just minutes from Madison. Known for its family-friendly atmosphere, quiet neighborhoods, and strong sense of community, Oregon provides an ideal balance of small-town charm and convenient access to big-city
Fall in love with home again at Main Street Townhomes, Oregon, WI’s newest workforce housing community where charm meets convenience. Nestled in the heart of downtown, these spacious 3-bedroom townhomes offer a thoughtfully designed floorplan with high-end finishes, an attached garage, and generous storage — all tailored for households at 30–80% AMI. Opening in November 2025, it’s where
Property Id: 2768228 Garden style end unit upper condo in Oregon available now. Unit has been updated with new carpet and fresh paint. New garbage disposal and dishwasher. Newer windows and HVAC. Unit features a vaulted ceiling with skylight over a galley kitchen with large walk-in pantry. Large primary bedroom has en-suite bath and walk-in closet. Patio overlooks small wooded lot. Washer
Luxury 3-bedroom, 2 1/2 bath townhomes for rent. 1,400 sq. ft. of living space, a two car garage, laundry hookups and storage on ground floor. Main floor has 9 foot ceilings, a huge living-dining room with gas fireplace, balcony, and fully appointed kitchen with breakfast bar, and a half bath. The second floor has a master suite with full bath and walk-in closet, and two more bedrooms with a
Rent this well maintained four bedroom farmhouse just outside of Oregon!Enjoy peaceful countryside views from the front porch of this charming 1907 farmhouse. Step inside to a welcoming formal dining room featuring beautiful hardwood floors, with a formal living room to the right and a cozy office to the left. The main floor also includes a bedroom and full bathroom. At the back of the
SUBLEASE available starting September 8, 2026! This sublease has an end date of 6/30/27 with the possibility to renew.APPLICATION PROCESS1.Go to and click on “Wisconsin” pull down tab in the upper right-hand corner. Click on “Available Rentals” in middle. Scroll down to find a unit of interest. Click on “Apply now” under unit description. Each roommate needs to fill out and
SUBLEASE available starting September 8, 2026! This sublease has an end date of 6/30/27 with the possibility to renew.APPLICATION PROCESS1.Go to and click on “Wisconsin” pull down tab in the upper right-hand corner. Click on “Available Rentals” in middle. Scroll down to find a unit of interest. Click on “Apply now” under unit description. Each roommate needs to fill out and
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