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5689 County Road D, Oregon
$574,900
4 Beds ⋅ 1 Baths ⋅ 2034689 MLS ⋅ ACTIVE Status
A rare opportunity to own 5.27 acres just outside Oregon! This unique property offers open pasture, mature trees, a traditional farmhouse, and a versatile outbuilding with office space. Enjoy the privacy and flexibility of country living while remaining conveniently located near Oregon, Madison, and surrounding communities. Whether you're looking for room for animals, hobbies, storage, or simply more space to spread out, this property offers plenty of possibilities. Bring your ideas and make this one your own!

5689 County Road D, Oregon
749 County Road Mm, Oregon
$450,000
3 Beds ⋅ 1 Baths ⋅ 2032332 MLS ⋅ ACTIVE UNDER CONTRACT 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
$425,000
4 Beds ⋅ 2 Baths ⋅ 2032685 MLS ⋅ 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 St, Oregon
270 Brook St, Oregon
$749,900
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.

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