$510,215Average Value$248Average Price per Sq Ft29Homes 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
Jason Iverson,
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 44 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 $481,031, up 2% from the median home sale price over the previous 12 months.
Showings start 3/27/2026. 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
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
Showings start 3/27/2026. 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
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
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
5 bedroom home for under 400,000?! Opportunities like this do not come around often. This move in ready home offers space, functionality, and updates throughout. The main level is filled with natural light, warm wood tones, and multiple living areas including a cozy living room with gas fireplace. The kitchen flows into the dining space, making everyday living and entertaining easy. Downstairs
Photos to follow. 3 bedroom 3 bath ranch condo featuring a vaulted ceiling great room with a gas fireplace. Open floor plan, awesome kitchen with island and stainless steal appliances. First floor laundry. Lower level has a 38-16 family room and 3rd bedroom and full bathroom. Extra large garage.
Lovely 3 bedroom, 2.5 bath ranch style/half duplex condo with 2 car garage just minutes from downtown Oregon Village! Enjoy the spaciousness of vaulted ceilings, primary bedroom and laundry on main level, gas fireplace, kitchen that looks out onto deck and scenic back yard. Exposed lower level has 2 bedrooms, family room and 1 full bathroom. Condo needs painting, carpet & miscellaneous updating.
Beautifully designed two-story home featuring an open main level with exceptional finishes and thoughtful details throughout. The gourmet kitchen showcases stunning Brazilian walnut flooring, rich cherry cabinetry, stainless steel appliances and walk-in pantry. The elegant dining room features a tray ceiling & French doors and offers flexibility as a formal dining or private home office. Main
Rarely does a property of this magnitude come to market. Five Bridges Farm is 80 pristine acres just outside Madison — a self-contained world of spring-fed creeks, ancient hardwood canopy, open prairie, and miles of private trails. Three landmark structures anchor the land: The Manor, a four-bedroom residence with a chef's kitchen, wraparound porch, vaulted boardroom, and multi-level patio with
Commuters, take note! Located just steps from Hwy 14 E, this 2-bedroom, 2-bath condo offers seamless access to downtown Madison while enjoying the charm of Oregon. Efficient floor plan, easy living, and an unbeatable location make this one a must-see.
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
One of a kind, custom built 5263 sqft home on 3 acre wooded lot w/new outbuilding offering living space & car lift. Under 10 mins south of Madison & backing to DNR & Ag land. Private 4 bed/4.5 bath house perfect for hobbyist or entertainer. Maple flrs throughout main level & into living rm w/20' vaulted clgs & custom blue magma quartz flr to clg frplc. Natural light throughout! Large 2nd living
Exceptional owner-occupy opportunity with serious income potential! This well maintained 3 unit property (with potential to convert to 5 units, buyer to verify) offers the perfect blend of personal residence and investment. Live comfortably in one unit while the other units help cover your mortgage - or maximize cash flow with additional rental configuration options. The property features
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
This upper floor 2 bed, 1 bath unit is in a great location close to vibrant downtown Oregon and walkable to Oregon School District schools. Enjoy nearby restaurants and shopping, while also being conveniently located near the highway for easy commuting to Madison. The well-maintained brick building features units with a massive kitchen, beautiful hardwood floors throughout most of the unit, and 2
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 townhomes located in Oregon WI. Easy access to the HWY, yet in a quiet area. All units come with attached 1.5 car (Shotgun Style) garage.No pets.**The appearance of the unit may vary slightly. We strongly encourage viewing the unit in person before signing any lease agreement. Opting to skip a showing is entirely at the renter's discretion.**
Discover the perfect balance of space and style in this well-maintained 2,150 sq. ft. home. Featuring a functional 3-bedroom, 2.5-bathroom layout, this property offers plenty of room for both relaxation and entertaining. The open-concept living areas flow seamlessly, providing a bright and airy atmosphere throughout.Located in a desirable Oregon neighborhood, this home is ready for
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
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