$511,775Average Value$251Average Price per Sq Ft40Homes 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
Fred Van Buren,
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 56 days. The median sale price for homes in Oregon, WI over the last 12 months is $486,782, up 2% from the median home sale price over the previous 12 months.
Amazing Oregon condo propertunity with park-like setting and all the kitchen updates you are looking for. Enjoy meals outside watching nature on the deck or the bump-out dining area. This 2-bed has exposed lower windows if you need to add more. The open floor plan makes it easy to entertain from the updated kitchen with maple cabinets and quartz counters breakfast bar to dining and into the
No Showings until 5/1/2026. This is the kind of home that feels right the moment you walk in. Set on a private 0.60-acre wooded lot, this 3-bedroom, 2.5-bath home offers a great mix of space, comfort, and style. Vaulted ceilings and skylights bring in natural light and create an open feel. The kitchen features granite countertops, stainless steel appliances, and opens to a small deck, perfect for
This impressive property combines modern design, thoughtful upgrades, and a premier golf course setting-truly a place to call home! Designed for both everyday comfort & exceptional entertaining. This backyard oasis features a 20x40 saltwater pool with sun deck, tranquil water features, electric cover, and multiple upper and lower patio areas. Inside, the home welcomes you with an open-concept
Prime 18.5-acre development land opportunity in Oregon, WI located minutes from Madison in the path of growth between Oregon and the Bergamont area. This acreage offers outstanding future development opportunity for builders and investors seeking land with residential subdivision, multi-family, townhome, duplex, or estate-lot development potential. Positioned across from holes 13 & 14 of The
Better than new and built in 2025, this thoughtfully designed home blends modern finishes with functional living. Featuring solar panels for added efficiency, this home offers a bright, open layout centered around a stunning kitchen with quartz countertops, a large island with breakfast bar, and an oversized walk-in pantry. The spacious primary suite includes a private en-suite with double vanity
Amazing Oregon condo propertunity with park-like setting and all the kitchen updates you are looking for. Enjoy meals outside watching nature on the deck or the bump-out dining area. This 2-bed has exposed lower windows if you need to add more. The open floor plan makes it easy to entertain from the updated kitchen with maple cabinets and quartz counters breakfast bar to dining and into the
Thoughtfully updated condo in a welcoming Oregon community! Vaulted ceilings and abundant natural light create an inviting main living space, complemented by upgraded lighting, new flooring, and a beautifully enhanced kitchen with added pantry cabinetry and butcher block counter. The main level offers easy everyday living, while the unfinished lower level is already prepped for future expansion
This stunning new construction home features an exceptional blend of modern design and contemporary finishes. This spacious 5-bed, 3.5-bath residence boasts an open-concept layout, ideal for both entertaining and everyday living. Thoughtfully crafted with clean lines and sleek finishes, the home offers a warm and inviting atmosphere. The kitchen is a chef’s dream, equipped with a large center
This new construction ranch-style home is in its final stages and ready to welcome you home. The main level offers a floorplan that flows seamlessly with an open concept design. Featuring vaulted ceilings, spacious living room, and a screened porch for indoor/outdoor enjoyment. The owner suite is complete with a walk-in closet, private bathroom with double vanity and a tiled shower. The finished
Under Construction. Get ready to fall in love with your brand-new home on Autumn Blaze Court. Arriving in September 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.
No Showings until 5/1/2026. This is the kind of home that feels right the moment you walk in. Set on a private 0.60-acre wooded lot, this 3-bedroom, 2.5-bath home offers a great mix of space, comfort, and style. Vaulted ceilings and skylights bring in natural light and create an open feel. The kitchen features granite countertops, stainless steel appliances, and opens to a small deck, perfect for
The Lavender is a thoughtfully designed ranch plan that combines efficiency with charm. Upon entering through the front foyer, you'll immediately notice a dedicated hallway leading to two well-sized secondary bedrooms, offering privacy and comfort. The Lavender's main living area boasts an L-shaped design that's perfect for family time and hosting friends. The kitchen is a standout feature,
Show 5/1. Beautifully maintained zero-lot-line 1⁄2 duplex with no monthly fees and over 3,000 sq ft of quality living space. Updates completed in 2014 include hardwood floors, fresh paint, and stainless steel appliances. The main level features a spacious great room with a gas fireplace, a bright dinette, and a chef’s kitchen, along with convenient main-floor laundry. You’ll also find two
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
The Villas are the ultimate in peace of mind living. Located within the Highlands of Netherwood, this unique neighborhood of Single Family homes brings all the conveniences of condo living (Fee: $200/mo) right to your door. Never mow your lawn or shovel your driveway again. Ideal for people that frequently travel or are in the area for part of the year. Walking path connects the neighborhood to a
Welcome Home Bonus!Secure your new home by signing your lease within 24 hours of your showing and beginning your lease by April 1 to receive one month of rent complimentary with a 12-month lease.Your next chapter starts here — let us make your move effortless.Terms and conditions apply. Offer valid on new leases only.Brand new one and two bedroom apartments located in Oregon.
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
Listing Write-up: 298 Prairie View StFamily-Friendly Living: Steps from Oregon Schools with Heat & Water Included!2 Bed | 1 Bath | 750 Sq. Ft. | Heat & Water IncludedThe Perfect Location for Your Growing FamilySimplify your life in this cozy, well-maintained 2-bedroom apartment situated in the heart of Oregon. Located directly next to the highly-rated Oregon Schools, this
Beautiful townhouse located on the West edge of Oregon overlooking green space. Private entry, two car garage, and storage on ground level, huge living room, kitchen, half bath and deck on 1st floor, and three bedrooms, and two full baths on 2nd floor. Includes water/sewer, trash/recycling. We should have a few units coming, starting in May and throughout summer.
Charming Colonial with Vibrant Victorian Interiors Nestled in Historic Housing District of Oregon, WI 18 Minute Drive to Epic Systems / 20 Minute Drive to Downtown Madison. 3 block walk to elementary school/playground & downtown Oregon. 5 Bedroom / 2 Bath. 2400 Square Feet (above ground level). Historic and Restored built-ins and fixtures. Stained glass
This spacious two story duplex in Oregon offers a comfortable and functional layout. The main level opens to a dining area that flows into a fully equipped kitchen. Just off the kitchen and dining area is a generous living room with access to a private deck and backyard. A convenient half bathroom and in unit laundry are also located on this level.Upstairs, you’ll find three bedrooms
Welcome home to this beautiful 4 bedroom, 2 bathroom single family home in Oregon. It includes an attached garage, fenced in yard, and an open floorplan. You will enjoy the large deck and concrete patio in the back yard, upgraded countertops in the large kitchen, hard surface flooring, and stainless steel appliances. The basement is finished and includes a washer and dryer.Pets
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