Oregon Homes under $500,000

Oregon Homes under $500,000

Welcome to Oregon, Wisconsin – a charming village nestled in the heart of Dane County, where small-town charm meets modern convenience. With its picturesque landscapes, vibrant community spirit, and a rich tapestry of local culture, Oregon is a hidden gem waiting to be discovered.

Oregon boasts a variety of recreational opportunities, from the scenic trails of the Badger State Trail to the serene waters of the nearby lakes. Families will appreciate the excellent school system and the numerous parks that provide ample space for outdoor activities and gatherings. The village is also home to a thriving downtown area filled with delightful shops, cozy cafes, and local eateries, making it a perfect place to unwind and enjoy the community’s hospitality.

For those looking to call Oregon home, the real estate market offers an array of options, particularly for homes under $500,000. Whether you’re a first-time buyer or seeking a cozy family residence, you’ll find charming single-family homes, townhouses, and even new constructions that fit your budget. These properties often feature modern amenities, spacious yards, and access to the village’s beautiful parks and recreational facilities.

Living in Oregon means embracing a lifestyle that balances tranquility with the conveniences of nearby urban centers like Madison, just a short drive away. With its welcoming community, beautiful surroundings, and affordable housing options, Oregon, Wisconsin, is truly a wonderful place to plant your roots and create lasting memories. Come explore the possibilities and discover your dream home in this delightful village!

Newest Oregon Homes under $500,000

163 Prairie Grass Road Unit 8, Oregon
$315,000
3 Beds ⋅ 2.5 Baths ⋅ ACTIVE Status
Welcome to this updated townhouse-style condo featuring three bedrooms and two and a half baths. The spacious, open-concept kitchen offers stainless steel appliances, abundant counter space, and a large dining area with sliding glass doors leading to a private patio? for relaxing or entertaining. LVP flooring flows throughout the main level, while the inviting living room features a cozy gas fireplace. Additional highlights include convenient main-level laundry and a partially finished basement with an egress window offering flexible space for an additional bedroom, recreation room, home office, or workout space. Enjoy a convenient location close to schools, parks with scenic walking trails, the public library, and downtown Oregon. This home combines comfortable living, functional space, and a great location! Finished space in the lower level has concrete floors. LVP Flooring(2024), Water Heater(2025), Washer(2025), Dryer(2022)

163 Prairie Grass Road Unit 8, Oregon

Listing courtesy of First Weber Inc.

712 Dunn Avenue, Oregon
$279,900
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status
Step into this bright and inviting condo where modern updates and comfort come together beautifully. The open-concept layout seamlessly connects the living, dining, and kitchen areas, creating a warm and welcoming space perfect for everyday living or entertaining guests. You?ll love the updated luxury plank flooring, newer carpet, and refreshed appliances that give the home a fresh, contemporary feel throughout. Stay comfortable year-round with a newer furnace, air conditioning, water heater, and roof?major systems already taken care of so you can enjoy peace of mind from day one. Step outside to the updated deck, a relaxing retreat with nice views where you can enjoy your morning coffee or unwind in the evening. This well-maintained condo offers the perfect blend of style, functionality, and easy living in a comfortable setting. Don?t miss the opportunity to make this charming home your own!

712 Dunn Avenue, Oregon

Listing courtesy of RE/MAX Preferred.

372 E Lincoln Street, Oregon
$419,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status
Welcome home to this beautiful ranch in Oregon set on a prime 1/3 acre lot backing to green space offering a private outdoor oasis. The home offers comfortable one-level living with a great mix of indoor and outdoor space. The main level features a bright eat-in kitchen with skylight, large living room, addition of formal dining room or flex space, three bedrooms, and a full bath. Step outside to enjoy the screened porch and deck overlooking the backyard - perfect for relaxing or entertaining. The partially finished lower level adds even more living space with a large rec room, game room, full bath, and wood-burning stove. Recent updates include a 2025 furnace and A/C, 2022 windows, and a 2024 deck.

372 E Lincoln Street, Oregon

Listing courtesy of MHB Real Estate.

883 Park Street Unit 102, Oregon
$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.

381 Cherry Wood Drive, Oregon
$449,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status
Now Available to See. Welcome home to this beautiful 3-bedroom, 2-bath property in the desirable Hickory Estates Neighborhood. The spacious kitchen and dinette area offer plenty of room for everyday living and features a walkout to a deck, perfect for outdoor dining. Enjoy the large fenced backyard with ample space for recreation and gardening. The living room provides plenty of natural light and a second walkout to a smaller deck overlooking the back yard. There is a family room with a wood-burning fireplace, creating the perfect gathering space. The spacious primary bedroom offers double closets. There is a bonus room in the lower level perfect for a home office, workout room or additional living space. Ideally located across from a park and just minutes from downtown Oregon. Combining comfort, space, and a fantastic location, this home is ready for its next owner to enjoy. New Roof & Siding 2025, A/C 2026, Washer, Freshly Painted and New Carpet. Move-in Ready.

381 Cherry Wood Drive, Oregon

Listing courtesy of Bunbury & Assoc, REALTORS.

118 Elliott Lane, Oregon
$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.

607 Hillcrest Drive, Oregon
$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.

1232 Tivoli Circle, Oregon
$434,900
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status
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 large park. Open-concept, ranch style homes have spacious living rms w/ direct deck access. Basements can be finished for extra living space & 3rd bed & bath. The majority of lots have half or full exposure in the basement. Multiple finish options & upgrades available. Builder is offering lots 1-30, see association docs.

1232 Tivoli Circle, Oregon

Listing courtesy of Keller Williams Realty Signature.

749 County Road Mm, Oregon
$475,000
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status
Inviting home on just under 4 acres within the top-rated Oregon School District, just 20 minutes from downtown Madison. The fantastic open layout creates an easy flow for entertaining, gathering with friends, and everyday living. You?ll love the character throughout, with original accents, exposed brick, gorgeous hardwood floors, and stylish finishes. Spend warm weather days on the patio taking in peaceful views of the surrounding landscape, then make the most of your 3.92 acres with a vegetable garden, apple orchard, chickens, or even your own hobby farm. The possibilities are wide open, whether you want room to roam, space for outdoor projects, or a place to create something all your own. The spacious 30x40? heated 4+ car garage offers plenty of room for vehicles, equipment, a boat, or your own workshop. A rare opportunity to enjoy country living with Madison just minutes away.

749 County Road Mm, Oregon

Listing courtesy of Real Broker LLC.

145 Dewey Street, Oregon
$425,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status
The best deal in Oregon School District! Don't let the age fool you - this home has modern, professional updates & upgrades in nearly every room, while gorgeous woodwork, stained glass, exposed brick & hardwood floors keep the charm of yesteryear. The kitchen is the true heart of the home and is as functional as it is inviting - with room to gather, tons of counter space & storage (don't miss the huge pantry!). Two large living spaces offer a flexible floor plan and room for everyone to find their favorite spot in the home. Upstairs, a truly spectacular primary bedroom addition shines with vaulted ceilings, incredible natural light & and a large walk-in closet. If you love outdoor spaces, there are so many great options - a welcoming, lemonade-sipping front porch; a large, sunny deck; and a beautifully landscaped, fully fenced yard. Newer windows, roof, HVAC, & garage + updated electrical & plumbing. Incredible location - walking distance to parks, schools, and downtown Oregon.

145 Dewey Street, Oregon

Listing courtesy of Relish Realty.

329 Soden Drive, Oregon
$304,900
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status
YOUR SPACE. YOUR PLACE. YOUR NEXT CHAPTER! Ready to trade rent payments for a place to call your own? This 2-bedroom, 1-bath ranch-style duplex at 329 Soden Dr offers approximately 1,100 sq ft of easy, single-level living! The open layout and vaulted ceiling create an airy, welcoming atmosphere, while a walk-in closet provides extra storage. The attached 2-car garage offers room for vehicles, tools and weekend projects. Step outside to your private fenced yard and patio, perfect for summer cookouts, four-legged friends or simply enjoying some fresh air. With a manageable layout, outdoor space and everyday conveniences, this home is a great opportunity to take the next step toward homeownership. Why keep renting when you could make this place your own? Schedule your private showing today and see it for yourself!

329 Soden Drive, Oregon

Listing courtesy of Stark Company, REALTORS.

377 Concord Drive, Oregon
$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.

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