Oregon Homes under $400,000

Welcome to Oregon, Wisconsin—a charming village nestled in the scenic Dane County, where small-town charm meets modern living. Just a short drive from the bustling city of Madison, Oregon offers residents a perfect blend of tranquility and convenience. With its picturesque landscapes, friendly community, and vibrant local culture, it's no wonder that Oregon is a sought-after destination for homebuyers.

One of the standout features of Oregon is its commitment to preserving its natural beauty. Residents can enjoy an array of outdoor activities, including hiking, biking, and fishing, thanks to the numerous parks and trails that dot the area. The village also boasts a lively downtown, filled with locally-owned shops, cafes, and restaurants, making it a delightful place to spend weekends with family and friends.

For those looking to settle down in this idyllic setting, Oregon offers a variety of homes priced under $400,000. Whether you're a first-time homebuyer, a growing family, or someone looking to downsize, you'll find a diverse selection of properties that cater to your needs. From charming single-family homes with spacious yards to cozy townhouses with modern amenities, there’s something for everyone in this welcoming community.

Oregon's strong sense of community is evident through its excellent schools, active local organizations, and numerous community events throughout the year. With a low cost of living and a high quality of life, Oregon, WI, is an ideal place to call home. Discover your dream home today and experience all that this enchanting village has to offer!

Newest Oregon Homes under $400,000

$250,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status

This 2-bed/2-bath condo is the best deal on the market in the Village of Oregon! 1st floor, zero-step entry from the garage and main entrance makes this condo accessibility-friendly. Laminate floors throughout most of the condo. New flooring in the bathrooms. Spacious primary bedroom features a walk-in closet and a walk-in shower in the attached bathroom. Huge pantry off the kitchen. Patio that backs up to a lovely, private green space. Move-in ready, yet room for your touches, if you're looking to put your personal stamp on your new home. 1-car attached garage. Hot water and water/sewer is included in the condo fee! Great location right off Highway 14 makes access to Madison so easy. Important amenities like schools, the senior center, a dog park, and Kwik Trip and Culver's are within walking distance. Homeownership is in reach with this great condo!

883 Park Street Unit 102, Oregon

Listing courtesy of Realty Executives Cooper Spransy.

$269,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Bright and spacious end unit condo offering the perfect balance of warmth and style! Private entry sets the tone for the feeling of home as you step into the open concept living/dining/kitchen areas that flow seamlessly together. 9-ft. ceilings and many windows for an abundance of natural light. Freshly painted and new carpet throughout. Kitchen features island with breakfast bar and has been thoughtfully updated with new countertops, sink and stainless appliances. Living area with cozy fireplace and walkout to private patio facing a backdrop of trees. Primary bedroom features en suite full bath and walk in closet. Additional bedroom and full bath. Convenient in-unit laundry. Attached 1-car garage that has direct entrance into condo. (New garage door-2026). Well-managed condo association, low monthly condo fees and healthy reserve fund. UHP home warranty for added peace of mind. Located in the sought-after Village of Oregon, move-in ready and waiting for you!

748 Dunn Avenue, Oregon

Listing courtesy of Stark Company, REALTORS.

$297,500

3 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status

Welcome home to this well-maintained condo in the desirable community of Oregon! This inviting property offers comfortable living with the convenience of an attached one-car garage and a practical layout with plenty of natural light and comfortable everyday living areas. Enjoy the ease of condo living while still having the benefits of your own private garage and additional basement space. Conveniently located in Oregon with easy access to local shopping, dining, parks, schools, and nearby Madison. A great opportunity for anyone looking for a move-in-ready home with room to make it their own!

118 Elliott Lane, Oregon

Listing courtesy of EXIT Realty HGM.

$385,000

3 Beds ⋅ 1.5 Baths ⋅ ACTIVE Status

Well-maintained multi-story home in the Village of Oregon offering 3 bedrooms, 1.5 baths, and plenty of flexible living space. The inviting sunroom is a great place to relax, enjoy your morning coffee, or take in the changing seasons. A finished basement provides additional room for a rec area, home office, workout space, or hobbies. Numerous updates throughout the home add comfort and convenience while still leaving room to make it your own. Conveniently located near Oregon schools, parks, and community amenities, with easy access to downtown Oregon and the surrounding Madison area. A comfortable and functional home in a great village location.

607 Hillcrest Drive, Oregon

Listing courtesy of RE/MAX Preferred.

$299,900

2 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status

This inviting townhome offers spacious bedrooms, a generously sized primary suite, and the comfort of a full primary bath. The home has recently been refreshed with all-new flooring, giving the interior a clean, updated feel.The two oversized bedrooms provide plenty of room for furniture, guests, a home office, or additional living space, while the large primary suite offers a comfortable retreat with its own full bath. With its combination of generous room sizes, low price point and recent updates, this property offers a wonderful opportunity for buyers looking for space and move-in-ready appeal in Oregon.

326 Alpine Meadows Circle, Oregon

Listing courtesy of Barnes & Associates Realty Group.

$312,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Homeownership Looks Good on You! Your first home should feel like a place you?re excited to call your own. Welcome to 329 Soden Dr, a 2-bedroom, 1-bath ranch-style duplex with approximately 1,100 sq ft of comfortable, single-level living. The open floor plan and vaulted ceiling give the home a bright, spacious feel, while the walk-in closet adds storage where you need it most. An attached 2-car garage is a major bonus for Wisconsin winters, weekend projects and all your extra gear. Outside, the private fenced yard and patio give you your own space for grilling, gardening, pets or relaxing with friends. Easy to maintain and easy to enjoy, this home offers a great opportunity to leave renting behind, put down roots and start making a space truly your own.

329 Soden Drive, Oregon

Listing courtesy of Stark Company, REALTORS.

$365,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Well maintained sun-lit 2-bed/2-bath condo in the highly-rated Oregon School District featuring great space, wonderful views, and offers the perfect balance of comfort and convenience. The main living area boasts vaulted ceilings, oversized windows, a cozy gas fireplace, and walkout to the balcony deck overlooking the property. The kitchen has abundant cabinetry, a spacious island, and an adjoining dining area surrounded by a bay of windows. The generous primary suite features a large walk-in closet and private bath. A sizeable 2nd bedroom, full bath, six-panel doors, office nook & convenient main-floor laundry round out the main level. The unit offers private entry and large 2-car attached garage! Close to restaurants, coffee shops, shopping, schools, & multiple nearby parks. Easy commute to Madison, Epic, and everything the area has to offer.

377 Concord Drive, Oregon

Listing courtesy of RE/MAX Preferred.

$394,900

3 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status

This Emerson home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 3 bedrooms, 2.5 baths, and a 2-car garage, this home showcases locally made, custom Auburn Ridge cabinetry, doors, and trim crafted to last. The stylish kitchen includes a center island, quartz countertops, and quality finishes from trusted brands like Kohler, Moen, and Shaw. Durable luxury vinyl plank flooring enhances main living areas, while painted solid-core doors provide superior sound control. Designer lighting curated from Kichler and Visual Comfort & Co. adds a polished touch. Smart Home+technology with integrated lighting control brings everyday convenience. Enjoy added peace of mind with a one-year warranty.

1043 Merri-Hill Drive, Oregon

Listing courtesy of Stark Company, REALTORS.

$384,000

4 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status

Must-see 3BR Ranch-style condo with updates and flexible living space! Main level features newer granite counters, appliances & flooring, gas fireplace, primary suite, laundry & 1/2 bath. Exposed lower level offers 2 bedrooms, full bath, spacious family room that could serve as a 4th bedroom, plus ample storage. New roof & siding in 2026. Newer deck off dining area. Ideally located close to parks, schools, shopping, restaurants, and everyday conveniences. This home offers a great combination of comfort, flexibility, and location. Condo is located adjacent to the Highway 14 corridor.

828 Dunn Avenue, Oregon

Listing courtesy of Century 21 Affiliated Roessler.

$399,900

3 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status

This Davis home features a thoughtfully designed, open-concept layout ideal for modern living. Offering 3 bedrooms, 2.5 baths, and a 2-car garage, this home showcases locally made, custom Auburn Ridge cabinetry, doors, and trim crafted to last. The stylish kitchen includes a center island, quartz countertops, and quality finishes from trusted brands like Kohler, Moen, and Shaw. Durable luxury vinyl plank flooring enhances main living areas, while painted solid-core doors provide superior sound control. Designer lighting curated from Kichler and Visual Comfort & Co. adds a polished touch. Smart Home+ technology with integrated lighting control brings everyday convenience. Enjoy added peace of mind with a one-year warranty.

1087 Tundra Avenue, Oregon

Listing courtesy of Stark Company, REALTORS.

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