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749 County Road Mm, Oregon
$475,000
3 Beds ⋅ 1 Baths ⋅ 2032332 MLS ⋅ 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

899 County Rd, Oregon
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 2032803 MLS ⋅ ACTIVE UNDER CONTRACT Status
A rare opportunity to own a luxury retreat on +/-13ac just outside Oregon, WI. This secluded estate is surrounded by mature forest and abundant wildlife, offering a peaceful country feel minutes from town. The home features a chef's kitchen with Wolf and Sub-Zero appliances, a grand entry, and refined living spaces with uninterrupted views of nature. The finished lower level includes its own kitchen, full bath, and walkout to a paver patio. This property is perfect for entertaining or escaping the hustle of daily life. Two impressive outbuildings, a 56x40 and a 30x24, provide exceptional versatility, including a batting cage and indoor basketball court. A one-of-a-kind property blending privacy, recreation and luxury. Schedule your private showing today. Open House - Sat and Sun!

899 County Rd, Oregon

145 Dewey St, Oregon
$429,900
4 Beds ⋅ 2 Baths ⋅ 2032685 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

255-259 Park St, Oregon
$575,000
2032203 MLS ⋅ ACTIVE UNDER CONTRACT Status
Calling all investors and owner occupants! Great opportunity to own a ranch-style side-by-side duplex in the heart of downtown Oregon. The 259 side has been gutted and completely redone, featuring new flooring and carpet, fresh paint, new doors and trim, new appliances and more—move-in ready for a new tenant or the perfect opportunity to live in one side while renting out the other! Major update with a new roof in 2024, plus one unit features a private, fenced-in backyard. Fantastic location just steps from schools, parks, pickleball courts, coffee shops, restaurants and everything downtown Oregon has to offer. Whether you're looking to add to your investment portfolio or offset your mortgage with rental income, this one is ready to go!

255-259 Park St, Oregon

541 Union Rd, Oregon
$799,900
3 Beds ⋅ 2 Baths ⋅ 2030248 MLS ⋅ ACTIVE UNDER CONTRACT Status
A country property unlike the rest! Set on 22.08 acres, this unique 3-bedroom, 2-bath home offers an open multi-level design with vaulted ceilings, exposed wood accents and a distinctive sunken sound/living room. Relax in the spacious four-season room surrounded by windows and overlooking the beautiful backyard and countryside. Approximately 15 acres are tillable and currently rented for corn/soybeans. This awesome property has an attached 2-car garage, a 47x34 shop with concrete floor/insulated walls/heated/built in compressed air/ventilation system, with room for 2+ additional vehicles. Plus 2 additional equipment/storage buildings—ideal for hobbies, equipment, animals or projects. RM-16 Zoning offers agricultural and other rural uses, with additional possibilities subject to zoning/CUP approval. Horses allowed. Updates include furnace/AC 2024, windows 2025, water heater 2021. Mature trees even apple, plenty of room to make this property your own! Ultimate UHP Warranty Included

541 Union Rd, Oregon

4802 Country Meadows Rd, Oregon
$949,000
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

270 Brook St, 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.