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$499,900
4 Beds ⋅ 2 Baths ⋅ 2028272 MLS ⋅ ACTIVE Status
Opportunity awaits on this 5 acre property just south of Madison in the Town of Oregon. This classic foursquare farm house features spacious kitchen and dining room, four bedrooms and main level laundry. 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. House and some outbuildings are in need of TLC. Property is also listed as vacant land. Seller is selling AS-IS.

5794 Lincoln Rd, Oregon
$435,000
4 Beds ⋅ 2 Baths ⋅ 2027678 MLS ⋅ ACTIVE Status
If you're looking for a beautiful blend of yesteryear charm & modern updates, don't miss this Oregon charmer! Gorgeous woodwork, stained glass, exposed brick and hardwood floors create a warm, memorable space. An updated 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. Numerous updates, including windows, HVAC, and a newer garage! Incredible location - walking distance to parks, schools, and downtown Oregon.

145 Dewey St, Oregon
$375,000
3 Beds ⋅ 2 Baths ⋅ 2027080 MLS ⋅ ACTIVE UNDER CONTRACT Status
Affordable homes w/ this much character, space, & outdoor potential don't come along often! This authentic Craftsman offers 3 beds, 2 baths, & over 1,500 sq. ft. of inviting living space filled w/ timeless character, original woodwork, hardwood floors, & abundant natural light. Gather in the spacious kitchen, let the conversation flow into the formal dining room or out to the back deck. A first-floor bedroom & full bath provide flexible space for guests, a home office, or main-level living. Upstairs, you'll find two additional bedrooms, a bonus room, & a primary suite w/ a sitting room or dressing area & ensuite bath. Start your mornings w/ coffee on the deck overlooking two parcels totaling a rare .26-acre lot w/ exceptional sunshine & endless garden potential. The heated pass-through garage is perfect for your next project, while the mostly fenced backyard offers room to play, entertain, & unwind. Walk to schools, parks, downtown shops, & an easy commute to Madison. UHP Warranty too!

135 Johnson St, Oregon
$300,000
2 Beds ⋅ 1 Baths ⋅ 2025491 MLS ⋅ ACTIVE UNDER CONTRACT Status
Just 1½ blocks from downtown Oregon, this character-filled bungalow offers a walkable lifestyle with easy access to local restaurants, coffee shops, parks, the library, and community events. Refinished hardwood floors, an enclosed front porch, and an open floor plan create inviting living spaces filled with timeless charm. The lower-level bonus room offers flexibility for a home office, workout area, hobby space, or recreation room. Enjoy outdoor living with a private deck, fire pit area, and raised garden beds. Practical updates, including central air and a durable metal roof, add peace of mind. Detached garage and additional off-street parking. Whether you're purchasing your first home, looking to simplify, or searching for a property with personality and convenience, this home delivers both.

224 S Main St, Oregon
$168,000
3 Beds ⋅ 1 Baths ⋅ 2025028 MLS ⋅ ACTIVE Status
Ideally located within walking distance of schools and downtown Oregon, this move-in ready 3-bedroom, 1-bath home blends affordability with thoughtful updates throughout. The main floor features a spacious primary bedroom, a warm and welcoming living room, and a convenient main-floor laundry room. The remodeled kitchen impresses with ample cabinetry, generous counter space, and an eat-in dining area. Brand-new luxury vinyl plank flooring and carpet flow seamlessly throughout. Step into the charming enclosed 3-season room at the front of the home; it's an ideal spot to unwind and enjoy the outdoors in comfort. Upstairs, two additional bedrooms. Outside, the fully fenced double lot provides exceptional privacy. Two garages offer abundant space for vehicles, a workshop, or extra storage; a rare find at this price point. A newer roof completes the package, giving buyers added confidence and peace of mind. Opportunities like this don't last long. Schedule your private showing today!

304 N 3rd St, Oregon
$990,000
4 Beds ⋅ 3 Baths ⋅ 2022796 MLS ⋅ ACTIVE Status
No showings until 5/13. Nestled in a serene, park-like setting, this 4,000+ sf rustic European-inspired cottage offers exceptional privacy surrounded by mature hardwood forest, perennial gardens, and spring wildflowers. Beautiful nature views of the landscaped terminal moraine can be enjoyed from nearly every window. The home showcases outstanding craftsmanship with custom cabinetry and millwork crafted from wood milled directly from the property, including red oak laundry cabinetry, a cherry primary bath vanity, quarter-sawn oak office shelving, oak kitchen bow window trim, a cherry built-in bookcase, and a walnut window seat. Modern conveniences include high-speed internet, a dedicated home office, and an easy commute—just 10 minutes to Oregon, 25 minutes to Madison. Additional 24’x40’ shop - basement features 220 volt outlets, equipped with 4" fine dust collection exhaust system for the artisan. The flagship property of this cul-de-sac. This is not just a home, this is a lifestyle.

4802 Country Meadows Rd, Oregon
$799,000
2016589 MLS ⋅ ACTIVE Status
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 spacious layouts, strong natural light and a solid rental appeal, making it attractive for long term tenants or short term rental possibilities (subject to local regulations). Outside enjoy a standout amenity rarely found in multifamily homes - a private pool, creating added lifestyle value for an owner occupant and premium rental appeal. Ample parking, Flexible use potential and a layout that supports both privacy and income make this a smart buy for investors and house hackers alike. This one checks all the boxes!

270 Brook St, Oregon

This information, provided by seller, listing broker, and other parties, may not have been verified. Copyright 2026 South Central Wisconsin MLS Corporation. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify perspective properties consumers may be interested in purchasing.